How Great Sales Managers Crush Their First 30 Days (In Six Easy Steps)

How Great Sales Managers Crush Their First 30 Days (In Six Easy Steps)

Chris Orlob
August 15, 2022

Great sales managers crush their first 90 days on the job.

Your first 90 days are a "black art." A well-kept secret of success.

Here's what I mean:

What "feels" like the right thing to do is usually counterproductive.


Most sales managers join a new job guns-a-blazin'.

They jump from thing to thing, desperate to make a quick impact.

Great sales managers?

They slow down in their first 30 days so they can turbocharge later.

Here are six things great sales managers do in their first 30 days.

P.S. Before you read on:

Download our FREE 30-60-90 day "cheat sheet."

It's the 140-slide deck we used to record our paid online course on crushing your first 90 days.

Giving it away, free-99 baby.

Do that now.

Before We Start, a Warning:

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.

With that warning...

Here's exactly what to do in your first 30 days.

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:

Don't move on until you've diagnosed this.

On to number 2.

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.

So let's talk about...

Exactly what to say in your "kickoff" meeting

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

Straight-forward enough.

So let's get to...

Number 3.

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."

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:


Here's a WARNING:

Your job is to play a support role. Not a leading role.

Your rep should lead. Not you.

You should be there to support, observe, chime in, and play a pre-planned part.

Only take over the call in code-red situations.

Which happens sometimes!

But most sales managers are too quick to chalk up a situation as "code red."

Let it play out. Watch what happens.

No one wants that.

So what do you do instead?

Here are four keys to running joint sales calls with your reps.

Ignore at your own peril.


Onto number 5.

One of my favorites.

Because of how bad at it I was years ago.

And how much it transformed my career once I mastered it.

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.



In your first 30 days, you want to show some momentum.

As I outlined, trying to make too big (or too many) changes early on is a career-limiting mistake.

But, you should start to get a little momentum going before day 30.

But don't disrupt. YET! It's a mistake to disrupt too early.

Here are a few examples of good and bad changes to make in your first 30 days:

The first group is fine.

The second group will create resistance if you do it too early.

You have learning and credibility-building to do before you tackle the second group.

Unless you're in a "bleeding from the neck" turnaround situation.

Then, all bets are off.

Here's what to do next

That's what to do in your first 30 days.

But here's the deal...

It's not your first 30 days that matter most.

It's your first 90.

I've taught you one-third of what you need to know.

Want to know what to do in days 31 thru 90?

Step by step, day by day?

Here's our 30-60-90-day cheat sheet.

It's free.

It's the 140-slides I used to record our paid online course:

How great sales managers crush their first 90 days.


Grab it here.

It will feel like stealing.

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