The Ultimate Guide to 1:1s for Sales Leaders Who Manage AEs

The Ultimate Guide to 1:1s for Sales Leaders Who Manage AEs

Chris Orlob
July 12, 2022

Tips for having sales 1:1s are all over the Internet.

Check it out. Google doesn't lie:

I bet this isn’t the first post you’ve read on 1:1s…

So what makes this one of the BEST posts on 1:1s you’ll read?

It teaches you a simple technique (that others don’t):

If you manage AEs, you should have different “types” of 1:1s as the quarter progresses!

You don’t have the same 1:1 each week.


You build a 12-week schedule of 1:1s throughout the quarter.

An "operating rhythm" with your reps.

In fact, there are about…

7 different types of sales 1:1s that drive AE success

In this post, you’ll learn how to do all seven.

Each one helps you move the needle on your number.

Let's start with the big picture:

I’m going to show you exactly how to schedule your quarterly rhythm of 1:1s.

As you learn the schedule, you’ll learn how to run each 1:1.

P.S. Before you keep reading…

Download my (free) 28 principles of successful 1:1s cheat sheet.

It is a force multiplier for everything you'll learn today:

Month 1 (Weeks 1 through 4)

The first month of the quarter is unique.

It’s a “level set” on the last quarter. Plus, a kick-off to the new one.

Here’s what your “weekly schedule” should look like:

Yes, some weeks have two 1:1s.

We’ll talk more about that later.

You start with a Quarterly Performance Review: A look back at the previous quarter. Plus, planning for the new one.

You’ll follow that with a schedule of coaching sessions and pipeline reviews.

These reinforce rigor like a screw in a two-by-four.

Here's how to run each of these.

Quarterly Performance Review

Your goal in the first 1:1 is to run a 45-minute session that helps your rep:

  • reflect on the previous quarter
  • create a “success plan” for the new quarter.

Before you do this, set expectations.

Reps need to know this is how you plan on spending your time together.

Otherwise, they might clam up. If they know what to expect, they won't.

Start the first day of the new quarter with this email:


Expectations: set.

Your reps should know what they’re getting into.

Step 1: Review results from last quarter

Start by pulling up last quarter’s dashboard.

Go over things like:

  • Closed-won
  • Attainment
  • Stack rank
  • Pipeline generated
  • Any other important KPIs

If your rep missed, this should feel like a “face the music” session.

A key function of this meeting is to drive accountability.

If your rep crushed it, they should look forward to the recognition.

Step 2:  Self-reflection to draw out learnings

After you level-set on the numbers, ask a few questions about last quarter.

Get your rep to self-reflect and draw lessons from their experience.

Things they can do moving forward to get better.

These questions work wonders:

Don't TELL them the answers to these questions.


It’s far better to ask than to tell.

A "secret" of great sales coaching is to get your REP to come up with the answers.

That way, they own it.

You teach them to think rather than feed them answers.

Step 3: Give your review of their performance

Let your rep know where they stand with you.

Are you amazed with their performance?





Be clear with your people on this.

And help them understand WHY.

Once you’ve done that, give them feedback that will help them improve.

Tell them the “HOW.”

If you’ve FIRST asked them questions to get THEM to come up with answers… now you can give them feedback.

Now that you’ve reviewed last quarter…

Step 4: Craft a “Success Plan” for this quarter

You’re 20-30 minutes into the one-on-one.

Spend the rest of the time creating a Quarterly Sales Success Plan.

This is not a PIP.

This is an action plan doc you do with everybody.

Here’s an example of what that looks like:

First, set a quarterly goal with your rep.

And spend time getting clear on the “math” to get there:

This might seem basic.

Even remedial.

But in my experience, only great reps get clear on this on their own.

And clarity on the numbers drives results.

Now, keep in mind…

This is a working doc you'll review each month.

It’s even worth a quick spot-check on a weekly basis.

Once you’re clear on the numbers, now create an action plan.

  • How are you going to hit the goal?
  • What are you going to DO?
  • What's the plan?

Brainstorm with your rep until you like the plan.

Here's a basic version:

I simplified this.

But you get the idea.

That wraps up the Quarterly Performance Review.

Now let’s move onto...

Bi-Weekly Coaching Sessions

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).

If I've convinced you to separate your coaching sessions, let me answer...

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.

How to run a great coaching session

The first coaching session should focus on defining 1-2 “focus areas.”

These are the skill gaps that you both agree to work on.

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.

If you have time left, spend it writing down 2-3 actions you both can take to start improving.

Things like:

  • Review a Gong call together
  • Read a book or article
  • Schedule a 1:1 teaching session
  • Listen to two calls from another seller


That’s how you do the first coaching session of the quarter.

Later, we’ll talk about how to do the follow-up coaching sessions.

Until then, let’s get into…

Weekly Pipeline Reviews & Deal Strategy

Here's something you might disagree with.

Yes, coaching is important.

But your FIRST job as a sales manager is to manage the pipeline and hit your numbers.

If you don’t do that, you won’t have the opportunity to coach!

You’ll be gone!

So let’s talk about how to run weekly pipeline reviews.

The kind that moves the ball forward.

Step 1: Review TOTAL pipeline… in CONTEXT

Start with the macro-view of their pipeline.

Don’t zero in on a single deal (yet).

Your goal is to understand the health of their quarter.

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

Slice it by:

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

It should look something like this:

Now, compare it to closed-won, goal, and the gap to make their number.

What does it tell you?


  • A rep has a $300,000 number.
  • $50,000 on the board so far.
  • $250,000 to go.
  • Total pipeline: $750,000.

Looking good.

But wait.

$600,000 of that pipeline is sitting in “Discovery” - the first stage of your sales process!

Either you’ve got a CRM hygiene problem...

Or that rep is in trouble.

Most of their pipeline might be too early to close this quarter.

When you start with the macro-view of their pipeline, it makes it clear where to spend your time.

In this example, you’d spend most of your time planning those early-stage deals.

Step 2: Review top deals: The “5 P’s” Framework

If you started with the macro-view of their pipeline, now you can zero in on deals.

But before you craft your deal strategy, you have to assess the situation.

Those are different things! But one leads to the other.

The way to do this is to ask the hard questions about your rep’s deals.

I use an incredibly effective framework for this.

It’s called the “5 P’s” deal review framework.

It helps you find deal risk better than any other method I’ve known.

It looks like this:

This framework is POWERFUL for deal reviews.

I’m going to ask you to do something with it:

Save the above image to your computer. Keep it somewhere you’ll view often.

And if you have a printer nearby, print it.

Keep it in sight.

If you master the 5 P's, you will “run your business” like clockwork.

Use it for six months, and I guarantee someone in your company will ask “what’s your secret?”

Step 3: Game plan one (or two) deals


You understand the health of the pipeline.

Now, help your rep move the ball forward!

After all, what good are you if you can’t do that?

Switch your 1:1 from review to brainstorming.

Don’t do more than 1-2 deals!

Otherwise, you’ll create surface-level, weak plans for several deals.

Instead of an airtight plan for one or two.

Plus, when you go DEEP on a deal, it will teach your rep how to do deal strategy.

They will start thinking that way for the rest of their deals!

Create an action plan with your rep on those top couple deals.

  • How do you get access to key people?
  • How do you drive urgency?
  • Can we get one of our leaders to reach out to theirs?
  • How do we box out the competition?

How, how, how.

And remember the key to great coaching:

Ask before you tell.

Get your rep to think before you give answers.

Step 4: Summarize action items

Here’s a simple, last step for great pipeline reviews.

One that most sales managers do not do:

Then, during your next weekly pipeline review…

Start the 1:1 by reviewing last week’s action items.

Do that enough weeks in a row, and you’ll have accountable reps who get sh*t done.

Summary of Month 1


You’ve learned the first four weeks of rep one-on-ones.

Here's that schedule again:

Want some good news?

The rest of this post is easy compared to what you've learned so far!


The rest of the one-on-ones build on top of what you’ve already learned.

You’ve got the foundations in place.

But, there are a few key differences in how to do the rest.

Month 2 (Weeks 5 through 8)

In month 2, you execute a rhythm.

One that drives rigor.

Most of your 1:1s this month are continuations of:

  • Success Plans (reviews and modifications)
  • Coaching sessions
  • Pipeline reviews

Here's the Month 2 schedule:

As you do these in the way I taught you earlier, you’ll gain a benefit:

The benefit of compounding.

Week over week consistency creates compounding benefits.

Now, these 1:1s, you already know how to do.

Except for one…

Follow-On Coaching Sessions


Didn’t we already cover coaching sessions in Month 1?

Kind of.

I taught how to do a KICK OFF coaching session.

The kind that defines the focus area you are going to coach to.

But once you’ve defined your focus area…

What do great coaching sessions look like to improve it?

Step 1: Do your pre-determined coaching activity

When you first designed the coaching plan, you crafted action items.

There’s a strong chance that you'll do one of those action items in a follow-on coaching session.


If you both agreed to review a call together, the scheduled coaching session is where you’d do that.

So that’s step 1.

If you had an action item designed for a coaching session, start with that.

  • Review a call
  • Talk through a situation
  • Give a training

Step 2: Follow the 4-Part Coaching Framework

If you had no scheduled action item, then spend your session asking questions.

The kinds that expand your reps' abilities.

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*


I get it.

Coaching is a BIG topic.

I'm sure you don’t feel like a master coach after reading that.

But I BET you do feel better equipped to coach than you did before.

You’re going to have to commit to coaching over a long period of time to become great at it.

The above framework will point you in the right direction.

But it's the beginning of your journey.

In the future, I'll go far deeper on coaching techniques.

So be sure to subscribe to get future issues.

Month 3 (Weeks 9 through 12)

As you enter the last month, your 1:1s should do two things:

  1. Laser-focus on winning this quarter
  2. Give you line-of-sight into the next quarter

Most sales managers only do the first.

Here’s what your Month 3 schedule of one-on-ones looks like:

First, notice that the first one-on-one of the month sets up NEXT quarter for success.

You’re creating next quarter's Success Plan.

Same as you did at the beginning of this quarter.

Since you already know how to do that 1:1, I’ll spare you.

But know this:

It is CRITICAL you do this in the first week of this month.


Because as you get closer to quarter-end, you and your rep will find excuses NOT to do this.

Quarter-end will consume you.





The last thing you will make time for is planning the next quarter if you wait until the last few weeks to do so.

Second, notice that you do the FINAL coaching session of the quarter a few weeks before the quarter ends.

You do this for the same reasons mentioned above.

Quarter-end is all-consuming.

Your reps need space to focus on closing the quarter during the last few weeks.

Give it to them. Punt on coaching for a few weeks.

Coaching sessions during the last two weeks of a quarter are ineffective.

Neither manager nor rep can focus on anything but quarter-end.

So, wrap up your coaching rhythm early in this month.

And start again in a few weeks.

Finally, notice that the last few one-on-ones include “EOQ therapy.”

Quarter-end is a stressful time for reps.

They are going to need to vent. Blow off steam.

So while you focus on helping them close...

Make sure you’re leaving plenty of time for them to “vent up.”

If you don’t, they’ll vent sideways. To their peers.

It's far better for reps to vent up to you than to their peers.

Since we're on the subject...

End of Quarter Closing 1:1s


You probably think you already know how to do this.

“Just focus on the last few deals, right Chris?”


This 1:1 is where true leadership comes into play.

Let me tell you a story that illustrates why

It was the last few days of June 2020.


One of my best reps had a $200,000 deal on the line.

We both forecasted it. Commit.

And they. Were. TOUGH.

The type of buyers who are too eager to show they’re willing to walk away from a deal.

That afternoon, we got an email from their SVP Sales.

“We only have budget for $100,000. If you can do that price, send over the contract. If you can’t, we understand and we’ll revisit next quarter.”

Heart drops.

Rage ensues.

There’s no way we’re cutting our price in half.

So my rep and I jump onto a Zoom 1:1.

“It’s over. It's going to slip to next quarter”

Those were the first words he said.

I decided to try something I’ve never done before.

“Bull shit.”

I said.

I wanted to rattle him out of his hopelessness.

“Look, I’m not going to give away the farm to get this deal. And I know you don’t want to do that either. But can I give you some tough feedback?”

“Yes,” my rep said.

“You’re being lazy.”

I don’t remember his next words, but I bet they weren’t far off from “Chris I want to f***ing kill you right now.”

“Let me explain,” I said.

“Giving up on this deal means you get to stop thinking. You’re letting yourself off the hook from doing the hard work of figuring this out.”

“Maybe this thing is dead,” I continued. “But we’ve got nothing else to do until quarter-end if we don’t close this. So let’s try this exercise...

“If you had to close this deal before quarter-end, at full-price - all $200,000 - what would you do?”

He took a deep breath.

His wheels started turning.

I could see it in his eyes. He was thinking.

That’s where things changed.

He started coming up with ANSWERS.

Good answers.

Bad answers.

Crazy answers.

But answers… rather than writing things off.

And guess what?

We closed that $200k deal at 10 pm. Last day of the quarter.

Don't misunderstand me.

I’m not taking credit for that deal.

My rep put 100 days of back-breaking work into that sales cycle.

But this story illustrates the leadership value of sales managers.

We all need a coach to look at our situations with a cool head, see what we can’t see, and challenge us.

That’s the function of the End of Quarter Strategy 1:1.

To lead.

Imagine if sales managers didn't exist.

And that rep was on his own.

Deal lost.

That's your value.

So... back to quarter-end 1:1s...

Step 1: Maniacally focus on winning

There are only two steps to this 1:1.

Lead. As I mentioned above.

And give your rep space to vent.

That is all your reps has emotional capacity for at this point (unless they are CRUSHING it!)

Spend your time planning how to get these last few deals across the line.

As I mentioned in my story, reps will give up hope.

They won’t be able to see things that are obvious to you.

Lead them.

Coach them.

Challenge them.

Don't let them stop thinking just because it's easy.

Thinking hurts.

Step 2: Give space for venting

There’s no more stressful time for a sales rep than quarter-end.

Particularly if they’re not at their number yet.

Be the person who gives them emotional oxygen.

Address the human. Ask them how they’re doing. And listen to what’s said (and what’s not).

Here’s What To Do Next

My hat goes off to you if you’ve read this far.

For those that have, I have a special (free) offer for you:

Do you want to DOUBLE the success of your sales one-on-ones?

Download my (FREE) “28 Principles of Successful Sales 1:1s” cheat sheet.

It summarizes 28 tips for having GREAT 1:1s with your AEs.

Get it for free here.

But there's something you need to know about this cheat sheet…

These are 28 BONUS tips...

I didn't include them in this post.

They act as a “force multiplier” to everything you’ve learned so far.

If they don’t overwhelm you with value, I’ll live the rest of my life in shock and awe.

So why didn’t I include them in this post?

I want to keep them a “secret” (sort of…)

If too many people know about these, they’ll become overused.

They'll soon come across as a "management technique."

And I want them to come across as genuine.

So, “inner circle” members only.

I’ll keep this cheat sheet up for a few weeks.

After that, it may be gone for good.

We'll see.

sign-up here, and get access to the AE 1:1 cheat sheet.

Download your own copy in case I take it down.

Here's my last ask of you:

I poured my heart into this post.

I hope it’s one of the best posts you’ve read.

If I halfway accomplished that, will you do me a favor?

Will you share this with other sales managers on LinkedIn?

That’d mean the world to me.

I hope it helps a lot of people.