117 Sales Leadership Tips & Techniques That Work Like an Absolute Charm

117 Sales Leadership Tips & Techniques That Work Like an Absolute Charm

Chris Orlob
August 31, 2022

Looking for a rich list of sales leadership tips and techniques?

The kind that will skyrocket your sales leadership success?

Look no further.

36 months ago, I opened a Google Doc.

And titled it:

"Sales Leadership - Lessons Learned."

Every week, I'd reflect. And write things I learned.

From mentors. From mistakes. From success. From books.

The doc has almost 200 entries.

I included 117 of them in this post.

And I broke the tips into sections:

  • First principles: general sales leadership
  • Deal strategy & pipeline management
  • Forecasting
  • People leadership
  • Hiring
  • Coaching & training
  • Quotas, comp, & territories
  • Performance management
  • How to crush your first 90 days

Let’s get started.

Subscribe (free) to future sales leadership tips here.

First Principles: General Sales Leadership Tips & Techniques

Let’s start with the BASICS.

These are your “First Principles” of sales leadership.

Get your blocking and tackling down first.

1. Success rises and falls on frontline managers.


You’re a VP Sales.

Which team would you rather have?

  • Great reps, mediocre manager
  • Great manager, mediocre reps



The quality of the manager is the biggest factor in long-term success.

What happens to the first team? The great reps with a mediocre manager?

Eventually, some of the great reps leave:

  • They get promoted
  • Leave for other opportunities
  • Turnover because they work for a weak manager

And what does the mediocre manager do?

Backfills them with mediocre reps.

18 months from now, here’s what that team looks like:

  • Mediocre reps, mediocre manager


What about the second team?

The GREAT manager up levels her team

  • Replaces bad reps with great ones
  • Coaches up the rest

Over time, now her team looks like this:

  • Great manager. Great reps.

"It’s the manager," as they say.


The success of strategic initiatives rise and fall on managers.

As a frontline manager, you’re the “bridge” between strategy and execution.

Upper management creates strategies.

Reps execute.

You build a bridge between the two:

2. Your job is to get things done through other people.

Not do things yourself.

This is the essence of sales leadership.


Moving from “doer” to “leader” is difficult.

What made you successful as a rep is counterproductive as a leader.

Here are a few examples:

Here's your #1 role as a sales leader:

To get things done through other people.

Write that down on a sticky note.

It’ll take a while for you to “get” that if you’re new to the job.

The only way to achieve beyond the limits of your own hands is to leverage the contributions of others.

Your reps.

Your peers.

Your partners.

Even your boss.

3. Get out into the field with your people. A lot.

Powerful benefits go to sales leaders who spend a lot of time in the field.

Now, here’s a warning that comes with this tip:

Play a support role on calls, not a leading role!

Your job isn’t to be a super seller.

Some managers dominate and take over calls.

That’s bad for these reasons:

Instead, follow these guidelines.

You’ll get all the benefits with none of the blowback.

3. If you don’t have a sales process, that’s your #1 priority.

If there is no sales process, putting one in place should be your top priority.

No sales process, no repeatability.

Your reps should be able to write down your sales process in a unanimous agreement.

They should all know the stages.

Why they matter.

How they align with “buying stages.”

And what happens in each stage (exit criteria).

Don’t have any of that?

Get to work!

4. Manage inputs more than outputs.

Want a sure-fire secret to feeling like you’re on a hamster wheel?

Focus only on deals that are about to close.

Click refresh on your revenue dashboard.

Now, want a sure-fire secret to crushing this quarter and next?

Spend most of your time managing inputs.

Things like rep KPIs that lead to success, finding new pipeline, and fixing bottlenecks in your sales process.

Think like a factory manager.

You don’t just inspect everything coming out of the production line.

You expect things at several points throughout the production line.

Now, approach your job the same way.

5. Prioritize people over tasks

I take my to-do list seriously.

I plan my day from beginning to end.

Here’s what today looks like for me:

But, I don’t let this define me.

I’m willing to throw it out at any minute.

ESPECIALLY when I was leading sales organizations.

When you’re a sales rep, you prioritize tasks over people.

Your CSM wants to chat?

Not before your prospecting is done.

When you’re a sales leader, you prioritize your people over your tasks.

That means filling your time with coaching and helping your reps create their personal development plans.

It means figuring out what motivates and demotivates each of your reps.

It means making sure your team has the training and support they need to get better.

6. Set standards that define greatness

One of your jobs is to set standards for your team.

What’s acceptable, what’s not, and what you expect.

Here’s where most sales leaders get that wrong:

They set standards that are their minimum expectations!

In other words, “do all of this to NOT get fired.”

Instead, set standards of excellence.

7. Your lowest producer is the de factor minimum acceptable standard

Think of the worst rep on your team right now.

By NOT addressing that person’s performance issues, you communicate to the rest of your team that their performance is acceptable.

Is that okay with you?

Maybe your worst producer is actually doing pretty well.

I doubt it.

Address weak performance swiftly.

It sends the right message to your team about what you’ll accept.

And that creates a culture of accountability.

8. Be the thermostat, not the thermometer

Your job as a sales leader is to be a thermostat. Not a thermometer.


  • adjust to their environment
  • respond and react
  • look to others


  • create their environment
  • initiate and proact
  • are looked to by others

Set the tone. Bring presence. Your people need that. That's leadership.

When a great sales leader enters a room, people adjust to her presence.

You must have a positive and enthusiastic attitude and bring your people up to your level.

Rather than go down to theirs.

9. You should probably terminate someone by day 90.

Your first 90 days are critical.

That's why we created a full course on how great sales managers crush their first 90 days:

If you’re just starting a new sales leadership role:

During your first ~45-60 days, you’re on a mission to identify which person on your team needs to be let go.

And then pull the trigger by day 90.

I know. No one likes this advice.

But guess what?

There are five big reasons to do this.

Here they are:

Ignore this at your peril.

11. Arm your team with what they need to win


Isn’t this product marketing’s job?

Or sales enablement?

You’re a sales leader! Your job isn’t tools and materials!

Actually, it is. If that’s what generates results.

Because that’s your job: win.

If it takes you putting together a slide deck every now and then, so be it.

12. Don’t roll anything out unless you’re committed to it (and stay the course when you do).

Reps revert back to old habits, VERY quickly without reinforcement.

Check this out.

Sales training is a great example.

This is true with any initiative that involves behavior change.

  • New product rollouts
  • New messaging
  • New sales processes, tactics, and playbooks

When you roll something out to your team…

The REAL work begins AFTER the rollout.

Stay the course.

Otherwise, they’ll chalk it up as “flavor the month.”

And you train them to stop paying attention.

13. Become the person at the company who knows the customer better than anyone.

Hit the road.

Get on calls.

Talk to customers.

Become the person who has spoken to more customers than anyone.

This is how you earn the right to be an expert on the company’s external environment.

. . .

Now that you’ve got those under your belt… Make sure you know how to crush your first 90 days on the job.

Download our FREE 30-60-90 day training deck.

It’s the training deck we used to create our paid online course on how great sales managers crush their first 90 days.


Download it here.

Deal Strategy & Pipeline Management Tips & Techniques

General sales leadership tips… DONE!

Now it’s time to manage the pipeline!

Pipeline management is both an art and a science.

And so many sales leaders overlook the TACTICS involved.

They just waltz in and try to close business alongside their reps.

But as you’ll see, there are pipeline management and deal review tips, tactics, and techniques that make your success FAR more repeatable than that.

Here they are.

14. The deal review process is one of your most powerful tools

Here’s something you might disagree with:


Your deal review program kills three birds with one stone:

First, you manage your pipeline.

Reviewing deals with your reps is your top tool for keeping tight pipeline management.

That’s your “business” objective.

Second, deal reviews are a GREAT vehicle to insert coaching into.

Instead of JUST managing the pipeline, now you’ve got a  platform for coaching.

You’ll see coaching opportunities in your deal reviews all the time as soon as you start looking for them.

Third, learnings from great deal reviews “scale” to the rest of a rep’s deals.

Learnings like this compound over time.

The magic here?

You don’t have to review every single deal to get the benefits of deal reviews.

Because of this scale-out effect, you only have to review a fraction of deals to change your rep’s behavior across MANY of their deals.

Solve once. Scale hundreds of times.

15. Before reviewing a deal, review the total pipeline

Start your deal review sessions with a macro-view of the rep’s pipeline.

Don’t zero in on a single deal (yet).

First understand the health of the rep’s quarter by looking at total pipeline.

Pull a CRM pipeline report (or Gong Deal Board).

Slice it by:

  • Stage
  • Forecast (commit, best case, pipeline)
  • Summarize the amounts

Should look something like this:

Now, compare that to what they’ve closed so far, their quota, and the resulting gap to make their number.

What does it tell you?

Here’s an example:

A rep has a $300,000 quota.

$50,000 closed so far.

$250,000 to go.

And a nice, $750,000 quarterly pipeline.

Looking good.


What if $600,000 of that $750k pipeline is in Stage 1 – Discovery?

Not looking so hot now.

Those deals might be too early-stage to reel in this quarter.

When you start with the macro-view of your pipeline, it helps you know where to spend your time.

15. Review deals with the “5 P’s” framework

When you’re ready to zero in on one or two deals, here’s what to do.

Start by assessing the situation of a given deal.

The “health.”

I created an incredibly effective framework for this.

It’s called the “5 P’s” framework.

It helps you find deal risk like a metal detector.

Here’s what it looks like:

Save that image to your computer.

Better yet, print it out and tape it to your wall.

Keep it somewhere you’ll view often.

You’ll use it all the time,

If you use this consistently, you’ll run your team’s pipeline like clockwork.

People will ask “what’s your secret.”

I won’t tell if you don’t.

16. Go deep on just 1-2 deals at a time

Most sales managers try to cover too much ground in pipeline reviews.

They try to “get through” every deal they can.

But remember the tip from earlier:

What a rep learns in one deal review can scale-out to the rest of their deals.

Don’t go shallow. Go deep.

After you’ve reviewed the total pipeline, pick a couple high priority deals strategize on.

And help your rep move the ball forward on those.

Instead of a surface level plan for a bunch of deals, you’ll create an airtight plan for 1-2.

17. Never end a deal review without action items

Here’s a simple, final step for great deal review sessions.

It’s one that most sales leaders (surprisingly) don’t do.

Then, next week in your NEXT pipeline review…

You can START the session by reviewing those action items.

Did they get done?

Do that enough weeks in a row, and you’ll have ultra-accountable reps who get things done.

Don’t end deal reviews with a whimper. Get the action items down.

If reps leave the meeting without documenting the agreed-upon next steps, they will move on to the next thing, completely forgetting the next steps.

18. A consistent sales process is the key to great pipeline reviews

Remember earlier?

I told you: if there’s no sales process in place, that’s now your #1 priority.

This is one reason why.

How the hell are you supposed to review pipeline, and deals, without a sales process?

Without one, you have no idea where you are with a particular deal.

And your pipeline is just a meaningless number.

Instead of a number sliced into stages that you can verify.

19. The sales process stage will dictate the questions you ask in a deal review

Let’s say you’ve got sales stages that look like this:

  • Discovery
  • Demo
  • Pre-Pilot Alignment
  • Pilot
  • Negotiate & Close

If you have a strong sales process, the stage will dictate your review questions.

For example, if a deal is in demo stage:

That means you've completed Discovery. As a result, I’d ask my rep questions like this:

  • What is the business pain you uncovered?
  • How is it quantified?
  • Who does it impact most?
  • Who are you working with? What’s their role?

Fast forward a week or two.

Let’s say the rep keeps advancing the deal.

We’re now in Pre-Pilot Alignment, which means she’s completed the Demo stage.

These would be my questions:

  • How strongly did they agree our product solves their business problem?
  • Are they willing to get the economic buyer aligned with us before we do a pilot?
  • Do you have a champion yet? How do you know?

Finally, let’s keep advancing on this one.

We’re now in the “Pilot” stage.

Which means we’ve completed the “Pre-Pilot Alignment” – a kickoff meeting for launching the pilot.

Now these are my questions:

  • Was the economic buyer in the room? How do you know she was the economic buyer?
  • Does she agree our product solves their problem?
  • Is the problem a top 5 priority for her?
  • What were the pilot success criteria you agreed on?
  • If we achieve that criteria, what additional steps do they need to take before purchasing?


20. The most common deal strategy mistake is pre-mature prescriptions

Your salesperson has probably been working this deal for weeks.

Maybe months.

And you have all the answers in minutes?

Think again.

Spend most of your time asking questions and brainstorming.

Rather than tritely jumping to “here’s what to do…”

Your salespeople just LOVE that...

Forecasting Tips & Techniques


Didn’t we just cover pipeline management and deal strategy?

Isn’t that the same thing as forecasting?


Deal strategy is about closing business.

Forecasting is about predicting it.

BIG difference.

What is forecasting?

There are a few negative ramifications of getting forecasting wrong.

These include:

21. Great sales leaders take forecasting seriously

Companies live and die on the accuracy of their forecasts.

It took me a while to “get” this.

When I was a new sales manager, I never understood why we forecasted.

I almost turned my nose up at it as a pointless exercise.

But here’s what it comes down to:

Your company’s decisions revolve around the forecast!

It helps leaders understand:

  • How much to spend on marketing
  • How much to staff up (or heaven forbid, staff down)
  • The general health of a revenue line

Here’s an example:

Let’s say the VP of Enterprise Sales predicts 20 new enterprise logos this quarter.

Well, the VP of Customer Success has to make sure her organization is staffed to onboard and support those 20 customers!

So she staffs up accordingly.

Now, let’s say the VP Enterprise Sales underdelivers.

Only closes 10 logos instead of the predicted 20.

Now the CS org has a bunch of CSMs with nothing to do!

On the contrary…

What if the VP Sales overdelivers on the forecast?

Closes 30 logos instead of 20.


There are a bunch of customers without the support they need.

The VP CS was expecting 20 logos. And staffed accordingly.

Now she’s overwhelmed with 30.

That’s a big deal.

Forecast well, and you’ll sleep well at night.

22. Don’t “delegate” forecasting to your reps!

Yes, reps should call their own number.

But delegating that to them without review?

Big mistake.

Most sales reps are too close to the action, and their judgment is clouded by wishful thinking.

So they don’t ask the tough questions that challenge their strategy for fear that they will spoil a good forecast.

This is your job as a sales leader!

It’s too important to delegate or trust your reps’ word without question.

You should be “clicking in” and drilling down on the decision-making process, politics, stakeholders, source of urgency, action items, and value proposition to see what your true chances are of winning.

Only then should you be able to sleep soundly at night.

23. Base deal-by-deal forecast on customer actions

Big forecasting mistake:

Forecasting a deal because of “boxes we’ve checked” in our sales process.

Rather than measurable actions customers take.

Forget that your reps sent a proposal. That makes a deal no more predictable than any other.

What did the customer do?

That’s the predictor.

That’s what indicates buying behavior.

24. Use a combination of “bottoms up” and “tops down”

There are two “types” of forecasting:

Tops-down and bottoms-up.

What’s bottoms-up forecasting?

It’s when you “bubble” up forecasts from the lowest levels of the company, to the highest:

  • Reps call a number to their manager
  • Manager calls a number to their director
  • Director calls a number to the VP
  • VP calls a number to the CRO

Bottoms-up forecasts come from what’s going on in the field.

  • What’s going on with deals?
  • Are there forces in the market giving you headwinds or tailwinds?
  • Do you have turnover, leaving a territory open, and creating a forecast “hit”?

By contrast, tops down is all about data and macro trends.

It has little regard for what’s going on in the frontlines.

It looks at things like:

  • How much you closed this time last year
  • How many leads you’ve been generating
  • Your sales cycle, win rates, and deal sizes

A good “tops down” process predicts a number based on these things.

Now, here’s the key:

Great forecasting “marries” both approaches.

Typically, you have revenue operations running the tops-down forecast.

And the sales leadership organization calling the bottoms-up.

Compare the two.

Argue over the delta between them.

That’s how great sales organizations predict and deliver.

25. Hold your reps accountable with a forecast reconciliation process

Many times, you’ll have reps forecast under their number.

You might even have multiple reps forecasting below their number all at once.

What happens in that case?

The manager (you) creates an action plan to make up for the gap!

And they create that plan themselves.

But that’s totally backward and unscalable.

You’re one person. You can’t solve for all 7-8 reps.

A forecast reconciliation “pushes” the burden of under-forecasting down to the rep-level so you’re not the bottleneck.


Let me teach you how to do this:

People Leadership Tips & Techniques


GREAT deal strategy techniques… Check!

FLAWLESS forecasting tips… Check!

Nice work.

But… we’re not done yet. Not even close.

It’s time to get nitty-gritty on people management.

The hardest (and most rewarding) aspect of sales leadership.

Let’s get to it.

26. Great people leadership involves personalizing and treating each rep differently.

You can’t lead people if you don’t know them really well.

Their work style.

Their motivations.

Their hopes, dreams, and aspirations.

Their fears and frustrations.

How they communicate.

Their personal life situation.

A blunt, firm style may work with one person. But may totally backfire with another.

27. Have a career conversation with each new rep on your team.

I stole this from Kim Scott in her book Radical Candor.

And I credit much of my success to doing it.

Here’s how it works.

Each time a new rep joins your team, schedule a 60 min meeting with them.

Ideally, it’s a walk-and-talk.

But if you’re remote, stick with Zoom.

Your goal is to get to know them at a DEEP level. What makes them tick?

Split the meeting into two halves:

First, dig into their past.

Start your conversation with (as Kim Scott suggests):

“Tell me about your life, starting with kindergarten.”

As you progress toward the present-day, look for life transitions they’ve made:

  • Did they change sports in high school?
  • Did they switch from sports to something else?
  • How did their passions change throughout life? Why?
  • What drew them to sales?

Here’s why you’re looking for transitions:

They tell you what TRULY drives a person!

What a person SAYS drives them and what ACTUALLY drives them?

Two different things.

Now, switch to the future:

What are their goals? Their hopes, dreams, and aspirations?

How do they see this job helping them get there?

Have these conversations, and you’ll have the “raw material” you need to lead your people.

28. Make few promises. Keep them all.

I learned this the hard way.

Eager to impress my new team, I made all kinds of promises.

I delivered on 10% of them. Total egg on my face. And had to rebuild my trust with the team.

Here’s the deal:

You never know what senior leadership is going to spring on your next!

So if you make a bunch of promises to your team, but then your senior leaders make new demands…

You literally won’t have time to deliver what you promised to everyone.

Simple math.

If you fail to follow through on enough promises to your team?

You’ll erode trust.

Make few promises. And keep them all.

Give yourself the buffer, slack, and space to be able to do that.

28. As a leader, remember you’re on stage every day.

Your people are watching you.

Everything you do, say, write, and the way you carry yourself sends signals to your reps.

These signals affect their performance.

If your heart is in it...

If you’re enthusiastic…

If you’re confident and optimistic…


Those things are contagious.

So are their opposites.

29. Get buy-in on new initiatives

I used to run my team with an iron fist.

Rep feedback?

Not needed!

My ideas were the best ones.

Wrong move. I made it really hard for myself to get people doing what I wanted them to do.

Once I wised up, I realized there’s a framework for rolling out new initiatives to your team.

Things like:

  • New messaging
  • New demo flow
  • New playbook

Here’s how the framework works:

First, plan to launch your new initiative in your weekly team meeting.

There are things you do before the meeting, during the meeting, and after the meeting to maximize buy-in.

Realize there will be three “buckets” of people:

  1. Reps who welcome the change
  2. Reps who are neutral
  3. Reps who resist the change

You will influence how many are in each “bucket” with your MESSAGING and PREP WORK.

Indeed, treat this team meeting like a sales conversation.

Your job is to persuade (without cajoling).

Here are three things to do BEFORE the meeting to make that happen:

Got it?


Use your sales skills.

A huge part of your job as a sales leader:

Internal messaging.

Yeah, yeah, I know.

That part of the job feels boring compared to being out with customers.

But alas, you chose management.

Own it.

Here are the 4 “Acts” to making this meeting go well.

You’ll notice it feels like a sales presentation.

Because it is.

Now, there are a couple of other rules of thumb for this meeting:

  1. Over-index on explaining the “why.”

    When you introduce a new priority without context, you invite resistance.

    When you explain the “why” in detail, you’re more likely to meet acceptance.

  2. Roll out the new initiative with conviction.

    Don’t be overbearing.

    But the “rollout” moment is not the time for wavering, uncertainty, forming your thoughts, or looking to your reps for approval.

    They will sense those things.

    Do that, and the priorities will lose “staying power." Reps will sense your lack of conviction.

    People follow people who are certain of what they’re doing.

Fortune is in the follow-up.

You rolled out the new initiative.

That was the easy part.

The hard work is ahead of you.

Reinforce, reinforce, reinforce.

Here’s how I’ve gone about it in the past:

30. When reps bring you problems, help them figure out a way to solve it without you.

Solve it for them every time?

You breed dependence.

Empower them to solve it for themselves?

That’s how you scale yourself.

Don’t neglect them. Coach them through self-solving.

Ask these two questions to start:

  1. What have you tried so far?
  2. What do you think you should do next?

The wheels of independent thinking will start to turn.

31. Don’t confuse your role. It is to extract performance.

Yes, you want to grow and develop your people.

Yes, it is to provide an environment where people feel appreciated.

But consider the purpose of your organization:

It’s performance.

You can measure that in several ways. Usually dictated by external and internal customers.

If that’s the goal of the organization…

And you serve the organization…

Then you have a purpose as a people leader:

Get your people to perform to their highest capabilities in service of the company.

It just so happens: coaching, developing, and recognizing help you do that.

32. Dictate outcomes. Not selling styles.

Define the right outcomes before anything.

And let each rep find his or her own route toward achieving them. Within reason.

When you standardize on outcomes, you avoid what’s counterproductive (and impossible anyway):

Forcing everyone to follow the same path you would to achieve them.

When you are religious about the ends, that prevents you from having to micro-manage the means.

Now you can avoid the all-too-common temptation of sales managers trying to “fix” each person’s selling style to fit her mold.

If one rep closes deals through great relationship building and another through challenging customers, then you don’t have to interfere…

As long as they achieve the outcome.

This approach has the enormous side benefit of encouraging reps to be accountable.

Dictate their style and path?

Now they’re not accountable. Only you are.

Bad news.

33. The hardest thing about being a leader is realizing that your people will not do things the way you would.

When I became a director of sales, here’s the first piece of feedback our CRO gave me:

You have to be okay with a) people doing things differently than you would and b) the quality of work being about 80% of what you’d deliver.

Trying to force reps to sell the way you would harbors resentment.

Not compliance.

Trust me when I say this:

Reps will not comply if they don’t want to.

In your attempts to get people to perform, don’t try to “perfect” them.

That’s not your role.

That temptation is always there and strong.

Resist it.

Don’t try to mold people to your image.

Set outcomes.

Give guard rails.

Train and develop.

But let their own path and selling style flourish.

Plus, this approach is FAR more fun.

Your job is not to correct people.

It’s to find their strengths. And help them capitalize on them.

34. The sign of a great people leader is being able to articulate the unique strengths of each of her people.

What drives each person?

How does each person think?

How do they best communicate?

What are their superpowers?

Great leaders don’t generalize their people.

They find out what’s unique and strong about each rep.

And they use that to bring out the best in their people.

35. Double down on strengths. Not weaknesses.

You want to grow your people.

The best way to do that?

Take their strengths. And make them stronger.

Turn your relationship builders into SUPER relationship builders.

Turn your challengers into SUPER challengers.

When you double down on strengths, you’re taking something positive, and making it even more so.

You’re going “from 1 to 2.”

When you correct a weakness?

All you do is get to average.

You’re going from -1 to 0.

At best.

36. Managing people by exception, is the only way to manage.

What does it mean to “manage by exception?”

It means you’re managing people as individuals.

Which is the only “right” way to manage people.

Some reps want you to leave them the hell alone as much as possible.

Others feel neglected if you aren’t regularly checking in.

Some reps are motivated by gain.

Others by pain.

Some crave private praise.

Others, public.

The best way to find all of this out?


Capture all of this. And keep track.

36. Spend MOST of your time with your BEST people

Here’s a common mistake of sales managers:

They spend most of their time with their weakest people.

Fixing. Repairing. Fire-fighting.

The best sales leaders invest in their best.

Spending time with a rep does not mean you’re fixing or correcting that person.

Remember your job? Extract performance.

When you spend time with a rep, you’re wracking your brain on how to get more performance out of that person.

Doing that with a GREAT rep is a FAR higher ROI activity than a weak rep.

The more you invest in great talent, the better the return.

Top producers actually have the MOST potential for growth and improvement.



But true.

If you invest in your best, you can expect a 10x return on your time.

37. Judge your people against excellence, not average performance

Great sales leaders don’t use average performance as the measure against which each rep is judged.

They use greatness.

Average is irrelevant. That’s not where you make the big money.

If “average” is your bar, that’s what you’ll get.

Hold your people to excellence.

Let them know and FEEL that’s what you expect on your team.

The mediocre ones may trickle out.

The great ones?

They’ll KNOW they’re in the right spot.

38. Time away leads to decay

No, I’m not talking about time-off or PTO.

You should take that.

I’m talking about leaving your best reps alone.

They have specific behaviors that made them superstar sellers.

If you take too much away from them…

Because you’re focused on “fixing” your worst reps…

Your best reps will decay.

Think of your best reps as thriving plants.

They need watering. Nurturing. Constant care.

In its simplest form, the sales manager’s job is to encourage reps to do MORE of successful selling behaviors and LESS of unsuccessful ones.

Don’t forget that your reactions can dramatically affect which selling behaviors are multiplied and which decay and die out.

The less attention you give to winning behaviors of your best reps, the less those behaviors will perpetuate.

Human beings are wired to need attention of some kind.

If they don’t get it, they’ll change their behavior until they do.

Don’t lose your stars.

Invest in them.

39. Eliminate talent roadblocks

Hate to say it.

But a big part of your job as a sales leader?

Eliminating administrative headaches.

But doing so serves a worthy purpose:

It frees up your people to use their talents.

You know… the talents that generate REVENUE.

In some sense, this means your reps don’t JUST work for you.

You also work for your reps.

40. Don’t assume your best people know their value

Every now and then:

Go back and tell your best reps WHY they are so good.

Explain to them the contribution they make to the team. The company. To you.

Sure, you want to avoid the conversation slipping into promises of promotion or pay increase.

That’s not what you’re doing here.

Just simply tell them why they are so valuable.

Don’t assume they know it.

Many stars… work hard to escape fear of failure.

They probably worry a lot.

Make sure they know.

In that sense, you’re constantly “re-hiring” them.

And reinvigorating them.

If you’ve ever been on the receiving end of this… you know its power.

You’ll run through walls.

Go inspire your best reps to run through some walls this week.

41. Balance accountability with teaching

If your reps KNOW how to do something… your job in that context is to hold them accountable to do it.

If they DON’T know how…

Then teach them.

Once you’ve taught them?

Go back to the beginning of the circle.

Back off and hold them accountable.

Repeat with each selling behavior or task you need them to do.

This “loop” is how you strike the balance between helping your people and staying away from making them dependent on you.

42. Should you become “friends” with your reps?

There’s nothing wrong with becoming friends with your reps.

On one condition.

You can continue to hold them accountable.

And evaluate them on achieving outcomes.

If you can do that with a friend, then sure. Become friends.

If you can’t, then don’t.


43. Discover each rep’s greatest talent

There’s a simple way to do that.

Ask reps what gives them the most joy on the job.

Some will answer with building connections with customers.

Guess what?

That rep’s greatest talent… is probably relationship building.

Others get a kick out of turning “no’s” into “yes’s.”

Well… that rep will probably make an incredible HUNTER.

And still… others love to understand and solve problems.

They’re probably amazing at discovery.

Double down on those strengths accordingly.

44. Be each rep’s “PR” scorekeeper

PR stands for “personal record.”

Each rep has their own personal records in a sales context:

  • Best month ever
  • Best quarter ever
  • Most pipeline generated in a week
  • Etc.

Keep track of these things. Each rep.

And push your reps to beat their own PRs.

A growing number of broken PRs means a growing, thriving sales organization.

Push your people to compete with themselves.

45. Your people will “starve” if you don’t give recognition

It took me pain and time to appreciate the importance of positive feedback.

If you give little or no recognition and praise, your reps are left to “survive” on their own emotional reserves.

And if they’re doing that… what good are you?

Yes… you’ll have some super self-starter types that can survive for a while on their own.

Most reps though will feel a drain on their energy.

Not everyone is you.

Not everyone is an ultra-disciplined person who doesn’t need positive feedback to keep pushing.

Make that a “note to self.”

I have to often.

Hiring Tips & Techniques


We should have started here.

There’s no single skill that corerlates more with your career (and financial) success as a sales leader than world-class sales hiring.

It’s one of the reasons over 1,000 sales leaders have joined the Sales Hiring Masterclass:

The top sales leaders in the world agree:

Let’s get into it.

46. Realize hiring is the magic pill (not really, but close)

If you were mediocre at coaching.

Mediocre at pipeline management.

Mediocre at operational rigor.

But GREAT at hiring… team of total A-Players.

You’d still probably be successful.

The opposite is also true.

Realize this:

And hiring is HARD.

Indeed. The current state of B2B sales hiring:

  • 40% of hires are mis-hires
  • Each mis-hire cost about $563k (on average)

It’s easy to see why:

So, let’s talk about how to do it well.

47. Create unmistakable clarity in your hiring

This is by far the most powerful thing you can do to improve your hiring.

Get crystal clear on three things:

Most sales leaders don’t define what they want - in detail - before they hire.

Or if they do, it’s in a sophomoric way, such as a job description.

Go further on these three areas:

  1. Role outcomes - You must define nuanced outcomes to achieve for your sales roles. "Close more deals" doesn't cut it.
  2. Ideal rep profile - The ideal traits, experiences, and skills, based on your role outcomes. And the sales environment in which you're selling.
  3. Evaluation methods - The pre-defined methods you'll use to assess attributes. Many sales leaders have an ideal rep profile defined. But without consistent evaluation methods, you're rendering an ideal rep profile useless. Inconsistent evaluation methods lead to inconsistent patterns and results.

I’ll unpack all three for you.

But if you’d prefer to take in the next three tips via video instead of writing, here you go:

48. Define Role Outcomes for each sales role under your purview

Here’s what Role Outcomes are not:

Job descriptions are a list of day-to-day activities.

They are not "desired outcomes" a role intends to achieve.

What's what a Role Outcome is: What are the nuanced desired outcomes the role must achieve?

"Close more deals" or "sell our product" doesn't cut it.

Let me give you a few examples.

This is the best way to learn what I mean by "Role Outcomes."

You'll notice we have three (very) similar-looking roles.

At least on the surface.

But when you dig into the outcomes, it's clear you're hiring for different hiring profiles for each.

Take a look at the first role:

Account Executive (1)

You can see we've defined  three Role Outcomes:

  1. close $800k in new business (across 20 logos)
  2. Maintain at least $1,000 price per seat
  3. Self-source three $40k+ opps per month

What does that tell you about this role?

A few things:

First, this role is focused on new business revenue.

But, not JUST that.

New logos.

In other words, it's not enough for this role to sell $800k by any means necessary.

Quantity of new logos matters. Two $400k deals doesn't make the grade. In this case, the hiring company has a strategic imperative to fill the install base with new logos.

Account Executive (2)

Once again, here's an overview of the three roles:

Let's compare AE(1) with AE(2).

Same job title.

Very different roles.

Very different traits, experiences, and skills needed.

Here are the Role Outcomes:

  1. Close $800,000 in net new ARR (across both new business and upsell)
  2. Close at least 12 new logos per year
  3. Expand top three customer accounts by 100%

This is a far different role than the first role.

Even though there's a focus on new logos, there's also an equal focus on upsell and customer expansion.

It's a hybrid role.

Now let's look at the last one.

Account Manager

  1. Close $900k out of a $1M renewal book.
  2. Sell at least $600k in gross upsell.
  3. Expand into at least six new customer success departments within your book.

That tells you a lot about the strategic imperatives of the company.

Write this down:

If you define generic outcomes, you'll hire generic reps. Who get generic results.

How could it be any other way?

49. Define a (3-part) Ideal Rep Profile

Most sales leaders have an ideal rep profile.

But they simply jot down what they think they should hire for based on their experience.

Rather than thinking: What do your Role Outcomes and selling situation demand?

There are traits. Soft personality traits such as grit and coachability.

There are experiences. What kind of sales experiences would a candidate need to be set up for success?

And then there are skills. What kind of selling skills do reps need to be successful?

50. Write a definition for each rep profile attribute

Once you've written the attributes of your ideal rep profile, write a definition for each.

Too many sales attributes are nebulous.

If you have nebulous attributes, two bad things happen:

  1. Misalignment on the hiring team (what are you hiring for?)
  2. You're not clear on what you're hiring for (even if it's just YOU).

"Coachability" is a great example.

Let's say coachability is a make-or-break hiring attribute you're hiring for.

What does that mean?

In fact, here's an exercise: Write down your own definition of that word.

Before moving on with this post.

Let's compare notes.

I'll wait.

Write it down now.



This will be a GREAT way to show how EASY it is to lack unmistakable clarity.

Now let's compare.

Here's what my definition looks like:

Here's what a lot of people might write down instead:

"The ability to take feedback. The ability to not resist coaching feedback."

That's fine if that's what you're looking for.

But notice my definition is different. I want to give someone feedback and see their behavior change.

If you don't have "coachability" defined in this case, you're not going to have a consistent way to assess it. Because now you're evaluating different traits.

You'll use different methods to assess the trait.

That leads to very different hiring outcomes.

51. Define Evaluation Methods for each attribute

Here’s the third part of Unmistakable Clarity.

Define HOW you’ll evaluate each attribute.

Write this down...

If you have inconsistent ways to assess the profile, you'll have inconsistent results.

How will you consistent assess each trait, skill, and experience in your hiring profile?

You must have a consistent evaluation method for each one.

If you VARY how you assess each attribute, you'll get noise instead of signal.

Most sales leaders only do the first one.

Before you move on, I created a free cheat sheet of 91 interview questions.

These are STRONG evaluation methods.

Look through the list. Swipe those that apply to you.

It's free.

52. Design a “predictive” hiring process.

And repeat it like clockwork.

You know how you have a repeatable sales process?

One with consistent stages and exit criteria?

Do the same for your sales hiring process.

Start by defining your STAGES.

You’ll repeat these EXACTLY for each candidate.

It could look something like this:

If you want your hiring process to PREDICT, then the steps must be repetitious!

Otherwise, you’ll get noise instead of signal.

Next define the objective for each step.

What are you trying to achieve with each?

Finally, assign “exit criteria” to each stage.

Based on the objectives you just set, what are the required hiring criteria that must be true in order to advance a candidate to the next step?

Could look something like this:

With all these in place, your hiring process should feel very RHYTHMIC by now.

Same stages. Same steps.

THAT is how you design a predictive hiring process.

It should feel boring.

Like you’re repeating the same thing over and over.

And that’s the point.

53. Ask behavioral interview questions

Got your ideal rep attributes defined?


Here’s the next mistake sales leaders make:

Again, this creates noise rather than signal.

Don’t ask what a rep WOULD do.

Ask what they HAVE done.

As much as this pains me to say:

Past behavior is the best predictor of future behavior.


What’s a “behavioral interview question?”

Let’s back up for a second.

There are actually three elements of predictive interview questions.

“Behavioral” is the first element.

Behavioral questions get the rep to talk about recent behavior, examples, and evidence of the attribute you’re screening for.

Need an example?

I’ve got a few for you…

Let’s say you’re hiring for “coachability.”

Here’s what a GOOD (behavioral) question looks like (on the left). Alongside a BAD (non predictive) question (on the right):

Notice the question on the left.

It asks about recent behavior. Evidence. Examples.

It’s EASY for a rep to fake their way through a “what would you do” question.

It’s VERY hard for someone to fake their way through a “recent example” question.

Ask about recent and past behavior. Forget about hypotheticals.

54. Ask CONSISTENT interview questions

What do I mean by “consistent”?

It means you ask the same set of questions to all candidates!

Why is that valuable?

Two words:

Pattern recognition.

If you ask different questions to various candidates…

You’re again creating noise, not signal.

You won’t be able to compare candidates because you’ve varied your process so much.

Keep your questions consistent from candidate to candidate.

That helps you tap into pattern recognition.

That helps you inject more objectivity into the process.

And, it’s fair.

55. Ask STRUCTURED interview questions

This is the THIRD element of “predictive” interview questions:

Remember the three elements?

Here’s a reminder:

We started with BEHAVIORAL.

Then we went to CONSISTENT:

Asking the same questions to all candidates.

The third element: STRUCTURE.

Asking the same questions in the same order.

You do that for the same reason we already talked about:

It creates objectivity. Not subjectivity.

And objectivity is your best friend when making quality hiring decisions.

56. Rate each attribute on a scale of 1 to 5

Done interviewing?

Here’s what to do next.

Take your ideal rep profile. The one with your ideal attributes.

And now, score your candidate against each attribute on a scale of 1 to 5.

Like this:

Doing this may sound simple.

Even remedial.

But here’s the key:

This practice comes from behavioral science.

It forces you into “objectivity.”

Have you ever heard of the Halo Effect?

Scoring on a scale of 1 to 5 eliminates it

Here’s the formal definition:

Here’s an example of The Halo Effect in sales hiring…

Let’s say you have a candidate that had top quartile quota attainment for four years in a row (!)

A track record of quota attainment is something you’re hiring for!

Great news!

But… it’s also imperative that the candidate be gritty, coachable, intelligent…. And a team player.

Well… the halo effect suggests that you may get TOO ATTACHED to the candidate because of her track record.

Even though she falls short on every other attribute.

But when you rate her on a scale of 1 to 5 across ALL attributes…

Now you see the forest instead of just the trees.

See how that works?

Your three best friends in making great hiring decisions:

  • Structure
  • Consistency
  • Objectivity

Scoring each candidate against your hiring criteria helps you have all three.

It eliminates natural human bias.

57. Run a chronological interview

I’m not going to spend a lot of time here.

Because I’ve written about this extensively elsewhere (and it deserves LENGTH).

Instead, I’m going to teach you WHAT this is…

And why it’s the single most predictive hiring technique on the planet.

Then, I’ll show you where to learn more.

Here’s the definition of a chronological interview:

This technique automatically reveals patterns.

Want to learn how to do this step by step?

Read how to do chronological interviews here.

And, check out the sales hiring masterclass.

58. Have a colleague run a “targeted interview”

Here’s what that means:

The goal is to drill in like a magnifying glass.

One last look at your candidate with heightened granularity on between 1 and 3 remaining hiring criteria.

Ideally, just one or two.

So you can FOCUS.

Here are the questions to coach your colleague to ask:

Have a colleague do this rather than you.

You need multiple, independent views on the candidate to maximize your odds of making a great hiring decision.

And here’s a WARNING:

Before your colleague talks to you about how the interview went, have them rate the candidate on a scale of 1 to 5 against each of the selected criteria you chose.

Don’t influence their thinking before doing this.

59. Run a “targeted reference call”

You’re ready to hire the candidate.

Take these last few steps before you do.

The first one: A targeted reference call.

A reference call constructed specifically to extract unbiased information.

Here are three things to keep in mind before the call:

  • Keep in mind that people do not like to give bad references. It damages their relationships. You’ll have to navigate these in a very nuanced way.
  • Talk to the references the candidate provides. But also ask for 1-2 more based on WHO you want to talk to (from their chronological interview)
  • Look at the non-verbal communication during your reference call. What does their passion (or lack of it) say about the candidate?

Now, once you get the reference on the line…

Here’s what to say during the call:

Don’t stray from that line of questioning.

It works like magic.

You’ll see what I mean. Go try it on your next soon-to-be-hired candidate.

60. Write a “hiring memo” to crystallize your hiring decision

Now it’s time to factor everything in.

You’re going to STEAL a technique from the venture capital world.

Before a VC makes an investment decision, they write a “deal memo” to their colleagues.

It’s a simple email that highlights the investment:

  • The overview of the deal
  • Company strengths
  • Management team
  • Risks and weaknesses
  • Competitive landscape
  • Outlook on the market
  • Final decision and recommendation

This is a simple tool that codifies the decision.

When you force yourself to put thoughts on paper, key insights emerge.

And the quality of your decisions rises.

Do this exact same thing for hiring decisions.

Write a “hiring memo.” Even if it’s just sent to yourself.

Here’s how I structure them:

Discipline yourself to write between two and five sentences per section.

No need to spend more than 15 or 20 minutes on this.

There are three powerful benefits of writing a hiring memo:

Make this part of your sales hiring process going forward.

Free cheat sheet: 91 interview questions that predict sales success:

61. A-Players only

When hiring, good is the enemy of great.

Not having a reason to NOT hire someone… is NOT a good reason to hire them.

Don’t buy into that saying:

“You can’t have ALL A-Players. Especially when you scale!”

Why not?

You CAN do that.

I’ve had that. Twice. Even through hypergrowth at Gong.

Championship teams have no weak links.

What would it cost you to settle for an “okay” rep if it means missing out on the superstar who would have joined you a month later and would have hit 200% of quota for the next three years?

Hold out for the best.

Even if you miss your hiring goals. Favor the long-term.

Free cheat sheet: 91 interview questions that predict sales success:

62. Get context on previous quota attainment

There are three better questions than JUST previous quota attainment to ask about:

  1. How did you compare to your peers?
  2. What percentile among your peers did you fall each year?
  3. What percentage of reps at your past company made quota?

Compare those answers to their previous attainment, and you’ll have a far better picture of the candidate’s previous success (or lack thereof).

Free cheat sheet: 91 interview questions that predict sales success:


63. What are they not getting at their current gig?

Ask candidates what they are looking for in their next career move that they aren’t getting in their current (or previous) job.

That question has a way of revealing what’s at the root of their current frustration.

Hire people who are moving toward something rather than moving away from something.

Free cheat sheet: 91 interview questions that predict sales success:

64. Include a writing exercise in your hiring process

Your reps represent your company.

A lot of that representation is done through email. Most of it, in fact.

You’d be shocked at how often well-spoken people come across as complete morons via the written word.

Harsh, I know. But true.

Ask candidates to craft email responses to sticky writing scenarios.


You’ll be shocked.

Free cheat sheet: 91 interview questions that predict sales success:

65. Don’t gloss over red flags

You’ll always regret it.

The most common form of glossing over a red flag?

Staying surface-level with your questions when it comes to the red flag area.

Easing up.

You’ll be tempted to do this if you have an urgency to fill the headcount.

The best sales leaders dig into red flags relentlessly until they’re completely satisfied.

65. Always be recruiting. Even when you’re not hiring.

Always be adding to your hiring bench, even when you’re not hiring.

There is nothing worse than an uncovered sales territory. And the temptation to fill it with a mediocre rep… because that’s all you have in your bench.

The quota clock is ticking and the sales leader with an uncovered territory creates a revenue gap that the rest of the team will have to make up.

This is your fault.

Failing to have a ready pool of candidates to recruit from means you are shirking a key responsibility as a sales leader.

Recruiting is the sales leader’s equivalent to prospecting.

Free cheat sheet: 91 interview questions that predict sales success:

66. Build a strong brand so the best reps seek you out.

Employer branding is not your job.

But some of the best sales leaders make it so.

All great software engineers will take a call from Google or Apple.

Be that place for great salespeople.

67. One-year stints in enterprise sales is a red flag

That’s not always the case in SMB sales.

In SMB sales… reps probably ramp in 2-3 months.

Crush it for a year.

And get bored and move on.

Say what you will about job hopping.

But moving on after a year in SMB doesn’t always indicate performance issues.

But it does in enterprise sales.

It takes about a year to “judge” an enterprise rep.

The sales cycles are long.

Ramp times are longer.

If your candidate had a one-year stint… give ‘em a break.

A bunch of them?

Red flag.

Free cheat sheet: 91 interview questions that predict sales success:

Coaching and Training Tips & Techniques

Next to hiring great people…

Coaching is the highest ROI activity sales leaders can do.

Regardless of how well you know how to coach.

Regardless of how skilled you are in coaching.

Regardless of how well you execute the mechanics of coaching.

One great coaching session could lead to hundreds of thousands in additional annual revenue.

That’s a high dollar-per-hour thing to do!

68. Realize that coaching is more about self-discovery than instructing.

Great coaching is about asking questions, guiding self-discovery, and creating new possibilities with your reps.

If your coaching starts with “Here’s what you should do…” you are probably not coaching.

If you’re too directive or prescriptive, by default, you’re no longer coaching but telling people what to do!

The most effective coaching focuses on helping your people think, analyze, and figure things out for themselves.

When you tell people what to do, you make them dependent on you.

Bad news.

69. Separate your coaching sessions from other 1:1s

First rule of coaching sessions:

Separate them from other 1:1s.

Do not try to “squeeze them into” your pipeline reviews.

Coaching sessions need their own space: Context switching kills coaching session success.

Don't buy it?

As a test, try this:

Do a pipeline review with your rep.

Then, in the same 1:1, switch to a skills coaching session.

See how effective it is (it won’t be).

70. Schedule bi-weekly sessions dedicated to coaching with each rep

Is there anything magic about bi-weekly?


But I’ve tried everything else. Bi-weekly works best.

Weekly is too much. You’ve got other 1:1s to do.

And monthly is not enough to build skills.

If you can stick to a bi-weekly schedule, you’ll win.

71. Define 1-2 focus areas at a time. No more.

These should be skill gaps that both you and your rep agree to work on together.

Here are some examples:

  • Asking better pain questions
  • Telling customer stories
  • Tailored value messaging
  • Outbound prospecting
  • Influencing the buying process
  • Driving timeline
  • Objection handling
  • Negotiation

Do you want to become a great sales manager?

Develop your own “skills matrix.”

A list of sales skills that are specific to what it takes YOUR reps to be successful.

Here’s a (sample) of one I used to use:

This is is a combination of:

  • Universal selling skills
  • Selling skills unique to YOUR sales environment

A skills matrix is a “menu” that helps you select concrete focus areas.

Now, how do you LAND on the right skill gap?

Step 1: Analyze data (if you have it)

Look at the metrics. Some of them highlight skill gaps.

  • Conversion rates drop-offs
  • Low price per user
  • Long time-in-stage
  • Small deals
  • Gong data

If you know how to pull these reports yourself, great.

If you don’t, ask your sales ops partner to help you.

Combine that data with your own observations.

(you did spend plenty of time observing them in action, right?)

Build your own point of view on your rep's skill gaps.

But don’t share it yet.

Step 2: Guided self-discovery

Here's a pattern of great sales one-on-ones:

Asking your rep GREAT questions that guide their own self-discovery.

As you start your coaching session, set the stage.

Let them know the goal is to agree on a focus area, plus a short list of actions to improve it.

Then ask these questions.

“I’d love to start by hearing your thoughts…”

Spend 10 minutes on this.

Get them to think about their skills.

Their strengths.

Their weaker points.

What it would take to get to the next level.

Step 3: Share your point of view

Remember when I said to build a point of view of your rep's skill gaps?

Well… you might TRASH it based on what your rep shared.

I've done this many times.

But if you still hold strong… share it.

Let them know the skills gaps (and strengths) you see in them.

And WHY.

Share the data if you have it.

Step 4: “Negotiate” the focus area

Now that you’ve both got your view on the table, land on something you both buy into.

One that your rep OWNS and that YOU feel will move the needle.

Once you land on the skill gap, document it.

Put it in a Google Doc.

72. Co-create a coaching plan together

You just spend time defining your focus area.

Now… with your rep, brainstorm action items you can both take to help the rep improve in that area.

Document them.

Assign ownership.

And deadlines.

Then, in your next coaching session…

Review them.

Did they get done?

73. Spend coaching sessions expanding your reps’ abilities

The first coaching session of the quarter… you spend defining a focus area.

What about those follow-on sessions?

Sometimes, you’ll do action items from the coaching plan:

  • Review a call
  • Run a training
  • Etc.

But often, you’ll spend these 1:1s doing the coaching itself.

Spend your session asking your reps questions that expand their thinking around the focus area.

Here's a four-part framework you can steal for doing skill coaching sessions:

  1. Current state of the skill
  2. Future state of the skill
  3. Obstacles
  4. Overcome

When you ask questions in this framework, you will “unlock” your reps' thinking.

Let me take you through a (real) example.

The rep and I focused his coaching on asking deeper questions during discovery.

Current state of the skill

  • Me: Ok. So we’re focused on “peeling back the onion.” What’s your take on where you stand with that skill?
  • Rep: I’m good at finding the initial business pain. But I stop there. I don’t dig.
  • Me: How’s that showing up in a way that affects your outcomes?
  • Rep: I keep getting deals that I THINK are going to close. But end up slipping due to lack of urgency.
  • Me: Yeah. That’s my take on the situation too.

Future state of the skill:

  • Me: So what do you think DOUBLING your effectiveness in this area would look like?
  • Rep: I’d be more comfortable asking “WHY” several times to get to the core of the issue. I’d be able to ask “why does that matter,” in more tactful language, enough times to surface more pain. The kind that creates urgency.
  • Me: What else would you be doing if you were excellent at this?
  • Rep: I’d be asking follow-on questions in a way that doesn’t feel interrogative. It would feel conversational. So I’d ask questions. Summarize. Offer my own insight. Ask another question. Rather than pummel them with questions.
  • Me: We're onto something here.


  • Me: You said something earlier I want to dig into. “I’d be more comfortable asking WHY.” What did you mean by that?
  • Rep: Well. It’s not that I don’t know what to ask. It’s that I’m worried I’m going to piss off the customer. I’m worried they’re going to get annoyed, thinking I’m asking to find pain I can later “use against them.”
  • Me: That makes SO much sense. We’re breaking through here. Before we dig deeper… what ELSE would stand in your way of mastering discovery in the way you described?
  • Rep: I can’t think of anything.
  • Me: Okay, let’s go back to comfort. Have you ever been in a position where the customer was GRATEFUL you asked certain questions?
  • Rep: Definitely.
  • Me: What was the situation?
  • Rep: They didn’t realize how BIG of an issue they had. Until I “held up a mirror” to them with questions.
  • Rep: Holy sh*t.
  • Me: You see where I’m going with this? If you come from a place of wanting to help, then your questions provide more value to your customer than they do to you.
  • Rep: Yeah. I haven’t thought about it that way but it makes so much sense.


  • Me: So what’s it going to take for you to act on this epiphany?
  • Rep: I need to prepare for five minutes before every call. I need to make sure I have questions ready that provide value.

*End session*

74. The behaviors you recognize, repeat.

You will see the behaviors you recognize repeated more often.

Reinforce best practices by recognizing your people when they do them.

When you recognize a specific behavior, the person will know what to do next time.

75. One coaching session will not do the trick.

A common mistake sales managers make is that one coaching session will “hit home.”

Most new behaviors and skills need heavy reinforcement.

Usually, at least four to six times before they stick.

That’s why you define no more than 1-2 focus areas per quarter. And stick with it the entire quarter.

Coming up with a skill gap is easy.

Closing one is hard.

76. Do not split your coaching time across reps evenly.

You don’t get paid for splitting your time evenly across your reps.

In fact, you get penalized.

When it comes to coachability, bucket your reps into three groups:

  • A - Strong desire to grow. Changes their behavior. Gets new results.
  • B - Changes behavior. But takes more effort.
  • C - Little to no openness for new behavior.

Spend 50% of your coaching time on the A’s.

Another 40% on the B’s.

And only 10% on the C’s. There’s not enough to gain here to do any more than that.

Sorry, C’s.

76. People “own” what they create.

The best coaching sessions have well-crafted questions that get reps to create (and own) their own solutions.

How much success have you had cajoling your reps into doing something?

Probably not much. Though there is a time and place for that.

Empower your reps to self-reflect and arrive at their own insights 75% of the time.

Be prescriptive the other 25%. When they’re just not getting it.

77. Ask Keith Rosen’s billion-dollar coaching question

A rep comes to you with a problem.

They want a solution.

When in doubt, say this:

“I’m happy to share my opinion with you. However, you’re much closer to this situation than I am, and I trust you and your judgment. So, what’s your opinion on how to handle this?”

That sends a very powerful message to your reps.

And, it forces them to exercise their critical thinking skills.

Which is what you want.

This isn’t a magic bullet. It’s just the start.

78. Spend a lot of time on call planning with your reps

Hugely underrated coaching hack:

Spend more time planning reps’ calls with them.

Not only will the call go better as a result of you helping…

But you’ll find coaching opportunities you never would have seen without doing this.

79. Coach the wins. Not just the losses.

Emphasizing wins, and the things that led to them, creates more wins.

Focus more on what your reps are doing right than just on what they’re doing wrong.

Here are a few questions you can try:

  • How did you turn that deal around?
  • What did you do differently on that call than what you usually do?
  • What did you do well that you’re proud of?
  • How did you respond when [x] happened?
  • What sales techniques did you use that led to this success?
  • What best practices did you use that you can use moving forward?

And finally…

What are you going to do to celebrate?

80. Always start feedback with self-assessment first

It’s counterintuitive.

But when giving feedback, instead of sharing what a rep did right or wrong, get their assessment first.

Sure, give your feedback.

But the rule to follow?

Only give feedback after self-assessment.

Here are a few questions you can use:

81. Every rep gets coached. Even the best ones.

Too many sales leaders position coaching as a remedial approach meant only for poor performers.

Avoid creating a culture that says:

“I’m coaching you because you’re broken and need to be prepared.”

Position coaching as something you do with everyone to make them even more successful.

Rather than something you do to “solve a problem” or “fix someone.”

82. Painful failures can create powerful coaching opportunities.

Sometimes, you have to let your reps suffer through their own mistakes and the agony of defeat rather than taking over and "rescuing" the sales call.

After a painful flop, people tend to be more open to good coaching.

Don’t rob them of that.

82. Try to ask 5 questions in a row before giving answers.

You might think I’m “anti giving answers” to reps.

I’m not.

I’m just in favor of trying to get THEM to come up with answers before you finally step in.

By the end of the fifth question, the rep you’re coaching usually has figured out how to solve their problem without you telling them what to do.

As mentioned, since the rep come up with their own answers and action plans, they are more motivated to implement them.

People rarely resist acting on their own ideas.

83. Vary your coaching style between A and B Players

When you’re coaching A Players, challenge them.

They are usually big thinkers.

Push them even further.

“How can you shrink your sales cycle?”
“How can you close even bigger deals?”
“If you had to double your income, how would you do it.”

Take a different approach with B Players.

Focus on improving their consistency.

That’s usually the challenge B-Players face.

Consistency of execution.

The more consistent they get, the more they improve.

A Players: Challenge.

B Players: Consistency.

84. Use softening statements before giving tough feedback

Allow your reps to emotionally prepare for what you’re about to say.

This phrase works great. Give it a try:

“Can I tell you something that might sting a little but will make you more successful over the long term?”

85. Most reps won’t develop themselves

That’s the reason your job exists.

According to Chet Holmes, only 10% of people have a learning mindset.

The other 90 percent will only pursue skill development if it's part of a job requirement.

So make learning and skill development part of their job requirement.

They build comfort zones involving habits and patterns that hold their success hostage.

This is why sales leaders must coach.

Quotas, Comp, & Territory Tips & Techniques

Time to talk about MONEY and ACCOUNTS!

Isn’t that exciting?

Say yes…

If there’s one thing that’s true about sales leadership, it’s this:

You can get a lot wrong and still be fine. Comp is not one of them.

86. Never talk about comp, quota, or account assignments in team meetings

Save these topics for 1:1s.

You’ll have to break this rule every now and then.

But make it rare.

Talking about these topics in team meetings has a weird effect on morale and rep attitude.

I’m not sure why.

It just does.

I wouldn't be surprised if you've experienced the same.

87. Always expect data errors in quota & comp plan assumptions when sales ops takes their first stab.

This is almost a law of nature with how accurate it is.

When you are creating next year’s annual plan… part of that process is comp planning and quota setting.

Sales ops usually owns that process.

And they’ll use PLENTY of data to try to set things right.

Your job is to find the error in their data.

It’s always there.

You’ll save yourself headaches months down the road when you realize quotas, comp, accounts, whatever were not set right because of some spreadsheet flaw.

Don't let the error go undetected.

88. Account continuity has a compounding effect.

When a company grows, account reassignments naturally happen.

Just realize: you’re interrupting compound interest when you do that.

Especially for customer (post-sale) accounts.

Shuffling accounts carries a major reset cost.

The longer a rep gets embedded into an account, the more compounding benefits they’ll accrue.

Even though account managers are always asking for new accounts…

Long-term account continuity beats the novelty of new accounts.

I’m sure there’s data that proves this.

But I don’t have it.

89. Be a pessimist when setting revenue targets and an optimist when carrying them out.


Nothing more to be said there.

Just plain good advice I received from my former CRO.

90. There are two types of comp: strategic and tactical.

Strategic compensation is annual compensation plans and long-term monetary decision.

Strategic comp helps the business achieve key business outcomes:

  • Revenue targets
  • New product goals
  • New market penetration

Tactical compensation takes the form of contests, SPIFFs, spot bonuses, etc.

These are meant to have a short-term impact and solve immediate problems.

Such as pipeline generation.

91. Keep strategic comp plans simple.

Can you communicate your comp plan in a single page?

That’s a good acid test for simplicity.

Any complexity should come from tactical comp.

If any.

91. Reps will underperform until they have their quotas, comp plans, and accounts.

Almost every company does this.

They delay getting their quotas, comp plans, and accounts out to the reps until several weeks into the new fiscal year.

The sooner these are out to the reps, the sooner they will sell.

If your fiscal year starts in January, get these out the first week of January.

Otherwise, you risk falling behind the revenue curve.

Without their quota and comp plans, they won’t hunt for new business. They’ll do only the bare minimum.

Reps will not give 100 percent effort until they receive and understand their objectives.

92. Not all sales dollars should be comp’d equally.

The goal of the comp plan is to achieve a business objective.

Is your company’s objective really just revenue at all costs?

Regardless of that type of revenue?

Probably not.

Some companies are focused on selling a new product.

Pay more for that.

Some companies prioritize new logos.

Comp accordingly.

Others want to see greater expansion and net dollar retention.

Don’t treat all dollars the same in the comp plan.

Pay more for strategic dollars. Pay less for opportunistic dollars.

93. Rep motivation is dictated by the quality of objectives.

Quota plays a huge role in the quality of a rep’s life.

Set quotas that are challenging yet attainable?

Recipe for motivation.

Set something that’s out of reach?

Morale killer.

Set something too small?


That just doesn't make sense for the business to do.

But I’m sure your reps would love it.

94. Comp plans should be a byproduct of this year’s strategy rather than last year’s goals.

Most companies set comp by building on what they did last year.

Big mistake.

Especially if the strategic focus of the company shifts.

Align comp with the current reality of your market by tying it to strategic objectives.

Selling is about today and tomorrow.

Not yesterday.

And not about how many reps did or did not make quota last year.

95. Comp plans are not a substitute for good management.

Some sales leaders take the lazy way out.

They use comp as their tool for everything;

  • To motivate
  • To penalize
  • To change behavior

Comp is just one tool in your tool belt.

Often, a dull one.

You can’t substitute good coaching, training, accountability, and performance management with comp plans.

You can’t manage people by spreadsheets and formulas.

Performance Management Tips & Techniques

No one likes performance management.

It’s the worst part of the job.

But the best sales leaders take it seriously.

Before we get too far into this one…

Let me start by defining “performance management”

It’s easily misunderstood.

It’s not just about dealing with underperformers.

It’s about improving them. Or removing them.

Many sales managers do performance management without an intention to improve.

If you don’t have that intention, terminate the rep.

No in-between.

96. Your job is to set performance expectations.

Across all dimensions of the job.

Not just quota.

If you don’t do this clearly, your reps don’t know what they should be doing.

And you have no basis for reviewing their performance.

Setting expectations is not just about handing out a quota and saying “good luck.”

Define the behaviors, attitudes, KPIs, and of course, results you expect.

And, be clear about the consequences of NOT meeting these expectations.

97. Performance management should start EARLY.

Imagine your low-performing rep is driving a car.

And they’re headed full speed toward the edge of a cliff.

Your job as a performance manager is to tell them they’re headed for a cliff as soon as that’s the case.

Ideally, 1,000+ yards out so they have time to turn it around.

But here’s what most sales managers do:

“Hey, you’re going 60 MPH and there’s a cliff in 10 feet!”

No one can turn that around. It's too late.

Instead, your performance management should look something like this:

  • 1,000 yards: “Hey, just so you know you’re headed for a cliff about 1,000 yards from now. Easy to turn around.”
  • 100 yards: “Yo… you’re still headed toward that cliff! And you’re getting closer… want to pump the brakes and head the other way?”
  • 50 yards: “You’re starting to run out of safe runway friend! Maybe press a little harder on the break and swerve a little…”
  • 10 yards: “Slam on the brakes now and turn the car around. This is the last chance before you go cliff-diving."

Give your people runway.

Summon the managerial courage to have these hard conversations as soon as you sense you should.

98. If you don’t address a poor performer, YOU ARE the poor performer.

Failing to swiftly address weak performance deteriorates the performance of your sales team.

If reps see that their peers aren’t held accountable, they’ll think:

“Maybe I don’t have to bust my ass. Maybe I should just coast, too.”

Reps learn from the cues of their leaders.

Performance issues are obvious to everyone on your team.

You’re expected to address those problems.

You’ll lose respect from your team (and organization) by not addressing it.

It’s easy to turn a blind eye to poor performers.

But that’s one of the worst things you can do as a sales leader.

99. Documenting PIP standards reduces fear.

This one is counterintuitive.

If you’ve ever been in a team meeting where you rolled out a new PIP process, you can practically SMELL the fear in the air.

It’s usually an unpleasant meeting.


The act of doing that actually REDUCES fear on your team over time.

Because now people know what to expect.

And they aren’t left ruminating:

“Am I about to be put on a PIP?”

They’ll know.

And if they know, the have no reason to worry or fester.

100.  The goal of a PIP is to achieve a positive result.

It’s not just a formality before you terminate someone.

If you’re going to do that, just skip the PIP and fire them.

Save everyone the heartache.

PIPs are not a tool to go through the motions.

If you don’t use a PIP with the intention of turning someone around…

Don’t use one.

101. Address performance issues swiftly.

Here’s a rule of thumb:

It always took you too long to address a performance issue.

If you sense it, act on it.


Address performance issues with great urgency.

Think about the precedent you set and the message you send when you tolerate less.

These situations don’t get better on their own.

If you aren’t sure if it’s time to put someone on a PIP, then it’s time. Go do it.

Early is better than late.

Nothing good comes from allowing weak performance to linger longer than it should.

103. It takes three people for a PIP to turn someone around.

  • You.
  • The rep.
  • Your boss.

If all three of you are not committed to achieving a positive result…

And if all three of you don’t believe...

Just fire the rep and pay them three months' severance.

Without commitment and belief from all three, PIPs end poorly every time.

104. Allow your reps to co-author their PIP.

No, I’m not saying you let them make easy rules.

But you have to collaborate on the plan.

If you create it all with an iron fist, they won’t have ownership.

And it will fail.

105. Define clear, written PIP criteria.

Make sure everyone knows what triggers a PIP.

Here’s one I used to use.

Change things to address your situation:

Feel free to steal what applies to you.

106. Don’t be seduced by potential. Judge only on results.

Most sales leaders get attached to a rep’s “potential.”

As a group, we're obsessed with potential.

But really, that’s only because we're attached to the outcome.

If someone is wrong for the job, “potential” won’t turn it around.

Lots of people have potential.

Few people tap into it.

Think about that.

As much as I believe in the unlimited potential of the human spirit...

I don't make my hiring decisions with that in mind.

You shouldn't either.

Because even though potential is a beautiful thing, few people do anything with theirs.

Hire and manage based on true, measurable achievement.

It’s very easy to get seduced into avoiding performance management because you’ll judge people on other qualities: their skills, their loyalty, their passion, etc.

All of these things are great, but if they’re not translating to sales numbers, they aren’t enough.

Cold hard facts.

Hope you like working in sales.

Tips for Your First 90 Days

If you're a sales manager starting a new job...

This is is the most important tip you'll read all day.

Here's why:

Your First 90 Days Will Make Or Break You

I wish it weren't that way.

But it is.

Think of the first 90 days as "wet clay."

You have an opportunity to shape your new role while you still can.

But once it's dry... it's like cement.

Not easily changed.

Download the free First 90 Days Guide:

107. Avoid “random acts of execution”

New sales managers are desperate to make an impact.

Which is great!

But it drives you to act chaotically.

Desperate to make a quick impact, new sales managers jump to random acts of execution.

Instead of building a focused plan.

So what do you do instead?

Build well-defined priorities and a focused plan of attack.

That's the right way to start your new role.

108. Avoid making changes too fast.

Imagine you're a rep again.

And you get a new boss.

And she immediately starts upending a bunch of things.

Q: Are you on her side?

A: Probably not.

Here's some GREAT advice I got during my first 90 days in one of my sales leadership roles:

Morbid, sure.

But useful.

There is a "yin yang balance" to driving the right amount of change early on.

Striking that balance is tough.

Here's the best "roadmap" for driving change I've ever known.

It served me well.

And it will help you understand "how much" change to drive, and when:

109. Avoid inadvertently undermining your reps

You should join customer calls when you start.

A lot of them.

But the role you play matters.

Talking over your rep, dominating, and leading the conversation?

Classic new manager mistake.

Play a support role instead.

Too many new sales managers take over and dominate their reps sales calls.

That comes from one of these five (misplaced) mindsets:

  • A desire to impress
  • A desire for quick revenue
  • A desire for control
  • An inability to allow you reps to make mistakes
  • A lack of trust in your reps.

These all lead to the same road:

You becoming domineering instead of an inspiring leader.

There are the five bad things that happen when you do this:

Not good.

So what do you do instead?

There are four key principles to joint sales calls with your reps.

Act accordingly:

110. Avoid trying to impact short-term revenue too fast

Nothing wrong with revenue.

That's your job, after all.

But trying to deliver a sharp increase fast?

That focuses you on the short term at the expense of the long term.

You'll become a super-salesperson instead of a true sales leader.

An unhealthy desire for delivering quick revenue will drive you into that hole.


Plus, it gives your boss the wrong expectations.

It can take "a while" to get the drumbeat going.

If you telegraph to your boss that they can expect a big uptick fast...


I pray for you.

Download the FREE Crush Your First 90 Days Guide:

111. Don’t under-communicate with your cross-functional partners.

Let me tell you a story.

We hired a new leader to run a segment of our org at Gong.

We'll call him "Loren."

He was smart and ambitious.

He spent his first 90 days building a kick-ass new playbook for that segment.

It was truly bulletproof.

He rolled it out to his team.

And they adopted it! It was a masterclass in change management!

At least... within his own team.

Here's where things went south:

He didn't communicate with his peers

Total silo.

None of his partners knew he was doing this.

It was extra bad because he was running a post-acquisition sales group.

So his team worked closely with other teams, like customer success and professional services.

So, his reps "let 'er rip" with the new playbook.

Their account teammates?

They had no idea this was going on. And it created an uproar.

A total mess.

Everyone complained that this team was doing something new, with no heads up.

Loren handled the damage control well. But he dug himself into a deep hole.

He left before his first year anniversary.

Spent that year trying to climb out of the hole.

I can't help but think his career would be different if he communicated.

The moral?

Schedule weekly 1:1s with your cross-functional peers.

Make them aware of what’s going on in your world, and changes your driving.

And become aware of theirs.

Download the FREE Crush Your First 90 Days Guide:


112. Don’t under-communicate with your new boss

Write this on a sticky note:

Boss's hate surprises.

Good and bad.

Yes, even the good.

Surprises of any kind make them feel out of control of their world.

And that means bad news for their relationship with their own boss.

When I first became director of sales at Gong, I was guilty of this.

The first 90 days are critical for expectation management.

They will shape your relationship with your boss.

When in doubt, over-communicate.

  • Weekly 1:1s
  • Daily Slack updates
  • Talk constantly

"No news is good news" does not apply here.

Download the FREE Crush Your First 90 Days Guide:

113. Use this 3-part framework for your first 90 days.

Crushing your first 90 days is a three-part framework:

In your first 30 days, you LEARN (in a very specific way).

Done that?

Once you've got enough under your belt, in days 31-60 your battle-cry is to "define."

Define your observations. Your priorities. Your plan.

And days 61 through 90?


Put it all in motion.

Now, here's the warning:

Misalignment with your boss is one of the top six mistakes new sales managers make.

Get on the same page with your boss.

And stay there.

114. Assess your team-type situation

Step one:

Assess the situation you're walking into.

There are three possible scenarios:

Why do this?

Because each of these demand different actions.


If you take over a team that's crushing it, and you're the new manager...

I dare you to come in and change a bunch of stuff immediately.

Your team will hate you.

Your job is to sustain (and build on) existing success.

On the other hand, if you're walking into a losing team...

You have an obligation to act fast.

You're doing a turnaround job. You have to. You may even have to fire people.

Here are your action items by situation:

115. Have a “kick-off” meeting with your new boss.

Step two:

Have a "kick-off" meeting with your new boss.

I've spent my career in SaaS.

In SaaS, when a new customer signs up, a customer success manager has a "kick-off" meeting with them.

They define success, metrics, an action plan, and expectations.

You should do the same thing with your new boss.

Critical in your first 90 days.

Imagine a skyscraper.

A great kick-off meeting pours a DEEP foundation in your relationship with your boss.

When you do that, now you can build a towering skyscraper on top of it.

Here's what to do, and what to ask to crush a great kick-off meeting with your new boss.

116. Have “career conversations” with each rep.

You can't lead your people if you don't know them.

Their hopes, dreams, aspirations.

And what drives them.

So, your next step is to have "career conversations" with each rep on your team.

I stole this from the book Radical Candor.

And it works like magic.

Here's how it works.

Schedule a 60-minute one-on-one with each rep.

Ideally, this is an in-person walk-in-talk.

But since everyone is remote these days, Zoom works too.

All scheduled?


Here's what to say:

Forget business.

Your goal is to get to know them as a human.

There are two "phases" of this meeting:

First, their past.

Go deep on their life to date.

That will help you understand what drives them.

Second, their future.

What are their hopes, dreams, and aspirations?

Here's the first question you ask. Stolen from Radical Candor:

"Tell me about your life, starting with kindergarten."

As you probe into their past, look for transitions.

Did they switch sports in high school?

Or switch from sports to something else?

What about career changes?

Why are you looking for transitions like this?

Because it gives you a clue to what drives them.

Not what they "say" drives them.

But what actually drives them.

Sometimes those are different.

Here's an example:

Once I did this with a rep who shared with me that he quit Lacrosse in 9th grade to join the swim team.

After a few more probing questions, here's what I learned:

He's competitive and likes to work alone.

It's not that he's a bad team player.

It's that he enjoys controlling his own destiny.

That insight paid dividends in our relationship.

Once you've spent 3o or 4o minutes on the past, now look to the future.

Define their dreams with them.

Jot these things down in a Google Doc. Keep files of your people.

You'll use this as quarterly career conversation "fodder."

Download the FREE Crush Your First 90 Days Guide:

117. Join as many sales calls as you can.

Powerful benefits go to those who spend a lot of time in the field.

That's where market intelligence lives.

That's where you learn what's working and what's not.

That's where you learn your people's selling styles, strengths, and weaknesses.

Here are five benefits of joining as many sales calls as you can:

118. Build deep relationships with cross-functional partners.

Build relationships (and over-communicate) with cross-functional peers.

Do this early and often.

Not doing this ruins careers.

It almost ruined mine.

Find your 3-5 key partners across the company.

Then make them aware of every move you're making.

Ignore this advice?

You're guaranteed to lose.

Like, 100% guaranteed.

Here's what a great model for this looks like:

Your goal in your first 30 days is to learn as much as you can from these people and to build relationships.

The topics will come later.

The value of this post is not the theory.

It's the execution.

So go schedule those meetings before you move on.

Download the FREE Crush Your First 90 Days Guide:


Grow Your Sales Leadership Skills

I have a confession to make.

I have MANY more tips.

If I waited to get them all down before publishing this post...

It would never see the light of day.

So here's what to do next:

Subscribe to the QuotaSignal Newsletter.

It's free. And more than 5,000 sales leaders are subscribed.

Do that here , and I'll do my best to keep sharing new tips: