How Great Sales Managers Hire Great Salespeople (6 Step Interview Process)

How Great Sales Managers Hire Great Salespeople (6 Step Interview Process)

Sales Hiring
Chris Orlob
July 5, 2022

Are you hiring sellers but TERRIFIED of making a bad hire?

Most sales managers are.

You start by hiring from your network:

The rolodex of great salespeople you know.

But at some point…

Your network becomes tapped out.

What do you do next?

You promote from within.

You hire that up-and-coming SDR. Or Junior AE.

But if you’ve exhausted that option, eventually you have to hire from the outside.

And that’s a terrifying crapshoot.

You don’t know what you’re really getting.

Fun fact:

Did you know that 40% of sales hires are MIS-HIRES?


They are terminated or leave for performance reasons… within 12 months(!)

That leads me to good news and bad news.

Here’s the BAD NEWS:

NOTHING hurts your credibility more as a sales leader than a bad hire.


If you’re hiring sellers, but you’re terrified of hiring a bad one, you’re not alone.

Here’s the good news…

There’s a dead-simple hiring “technique” that DOUBLES your odds of hiring A-Player salespeople.

It helps you reveal exactly WHO you’re hiring by using pattern recognition.

I used this exact technique to build the highest-attaining sales segment at Gong.

Once I started using this, my team went from 85% of our annual number… to 141%.

And the best part? We had a ton of FUN.

Having a team of A-Players is a blast.

In fact, we were so successful, that HALF of my team auto-qualified for President’s Club.

It was practically a “Team Orlob” offsite!

That success came from great sales hiring techniques. Including my master list of interview questions (you can download that for free).

We hired A-Players among A-Players.

And the most important aspect of my sales hiring process was…

The 6-Step Chronological Sales Interview

This 6-step interview is the most predictive sales hiring technique on the planet.

It’s where you ask a consistent handful of questions about each of a candidate’s past roles, starting with their earliest roles, and repeating the process as you move toward their most recent roles.

Sounds simple enough, right?

It is.

The reason this is such a powerful technique is it automatically reveals patterns.

As you ask the same questions about each role they’ve held, unmistakable patterns emerge.

Patterns about their work habits.

Patterns about their successes and failures.

Patterns about what drives them.

Patterns about “red flags” that would otherwise go undetected.

In this post, I’m going to teach you this powerful sales hiring technique, step by step.

You’re going to learn:

  • Word-for-word interview questions to ask
  • How to structure the interview for maximum success
  • At what stage of the hiring process you use this technique
  • How to identify PATTERNS that usually fly under the radar
  • How to double your rate of hiring A-Players by analyzing the answers


Here are the six steps.

P.S. before you move on, download our free interview questions cheat sheet. You'll use it later.

Step 1: Schedule 60 minutes with your candidate

I can already hear you hemming and hawing.

60 minutes?! I don’t have time for that!”

But remember what I said earlier?

Nothing hurts your credibility more as a sales manager than a poor hire.

And... A-Players cure-all.

So spend the time.

Still with me?


Now, keep in mind:

This is NOT the FIRST step of the hiring process. This is the second or third.

Candidates who haven’t passed your screens do not deserve this time yet.

After the initial screens and discovery call role play (if you do one), schedule a 60-minute “deep dive.”

This is where you’ll do your chronological sales interview.

Step 2: Tee up the interview

All scheduled?


You are going to spend 60 minutes with your candidate doing a career history deep dive.

You’re going to ask them repeated, consistent questions about each of their previous sales roles.

It’s okay to skip some roles if they have a long career history.

There’s no magic in asking about “every single role.” Asking about most of the roles will do.

Now, to make this work, you need your candidate to loosen up and feel safe.

So here’s how you tee up the conversation:

This talk track seems simple.

Even innocent.

But it’s POWERFUL.

This will loosen them up like cold butter in a microwave.

Most candidates end up enjoying this interview once they know what to expect.

Go figure.

Step 3: Ask “pattern revealing” questions about each role

Alright, here’s where the magic starts.

You’re going to ask (roughly) the same questions about each role they’ve had, starting with their earliest roles, and working your way through each role chronologically to PRESENT DAY.

When you do this well, patterns emerge that you would have missed.

Good patterns.

Bad patterns.

Ugly patterns.

All of it.

You’ll know exactly WHO and WHAT you’re getting.

So let’s get into…

The EXACT questions to ask about each role

Naturally, you’re not going to be able to “deep dive” into every single role they’ve had.

You “only” have 60 minutes.

So let me start by showing you the FULL LIST of questions to ask for each role.

But here’s an important warning…

Are you listening?

Great. Because this is the KEY to doing this right:

You will “cut down” this list of questions dramatically for their earlier roles, and “layer on” more questions for each role as you progress toward present day.

In other words, you’ll spend a LIGHT amount of time on their early days…

And you’ll go DEEPER on their most recent roles.

With that warning out of the way, here’s the full list of questions.

Read them carefully. Do not skip this part!

Now, let me address the two “concerns” you might be having right now.


You may have noticed… there’s nothing special about these questions!

WTF, Chris?!

I spent all this time reading and that’s all you’ve got?!

Write this down on a sticky note:

The magic is NOT in the questions.

The magic is in REPEATING the questions across roles to identify PATTERNS.

Now let me off the plank so I can address your second concern:

“You want me to ask ALL of those questions… for EACH role?!?”

Glad you asked…


Remember when I said…”You will cut down this list of questions dramatically for their earlier roles, and layer on more questions for each role as you progress toward present-day”?

Well, that above list is the expanded list of questions you’d ask about each of their two most recent roles.

So, for earlier roles, you’ll cut down the questions.

Let me give you an example…

Let’s say you have a candidate that has SIX previous sales roles.

That’s a lot to ask about in 60 minutes!

So as you start the interview, you’ll ask a FEW of the KEY questions about their earliest roles.

The cut-down version looks like this:

See how it's much shorter than the expanded list?


So now you move on to their “middle two” roles.

You’ll layer on just a few more questions.

Like this:

See where I’m going with this?

Start with a few questions. And expand more as you go.

Finally, as you move on to their most recent roles, you’ll ask the full, expanded version.

Like I said:

Spend a little time on early roles. Just enough to pick up basic patterns.

And MORE time on recent roles.

The time you spend on each role as you move through the interview should look like this.


Is it critical that you ask all of these questions? Exactly how I have them laid out?


In fact, it’s RARE that you’ll get through an interview in the exact way I described.

As you gain experience, you’ll make judgment calls about which questions to include and exclude based on the time you have.

But what you just learned is a fundamental framework for interviews that help you predict sales success.

Before you start analyzing the answers, there’s one more step.

Step 5: Turn to the future

You’ve just spent the last 50 minutes talking about the PAST.

Now turn to the future.

Ask your candidate:

  • “Tell me about your career aspirations moving forward. What do you want in your next career move that you’re not currently getting? What about long-term?

Your candidate will LOVE being asked this. So few hiring managers ask it.

Plus, it does a few things for you:

FIRST, it’s a congruency test.

You get to see how congruent their PAST actions are with their desired future.

Bizarre mismatches are a yellow flag.

Not a deal-breaker. But something to be aware of.

SECOND, it gives you the ammo you need to SELL.

If you’ve got a great seller on your hands, you’re going to need to convince them to work with you.

If you know their goals, now you can sell.

Step 6: How to analyze the patterns


You just spent 60 minutes with a candidate.

Time to debrief and analyze.

If you followed this framework, it was probably the most revealing interview you've ever done.

In fact, you might not even need this entire section. The patterns are probably clear to you.

But in case you need some help, here are a few tips to unpack the interview:

  • What was the most common reason they left prior jobs?

There are good answers and bad answers.

Good answers are they outgrew the job and wanted their next growth challenge.

Bad answers… performance reasons. And an inability to get along with people.

Remember to look for PATTERNS!

If someone was let go once… give ‘em a break.

That’s just a “dot.”

But two or three dots form a line.

  • Do they have a track record of success and excellence in their life and career?

Is this a common theme for them?

Were you impressed by what they’ve accomplished?

Or did you run into mediocrity with plenty of justifications?

  • HOW did they achieve their key accomplishments?

This is where you'll separate fool’s gold from the real stuff.

The HOW matters.

Can they explain it? Do they have a system?

If not, their success isn't repeatable.

  • What story does their quota attainment track record tell?

At some companies, “average” reps are hitting 120%.

At other companies, hitting 100% might be a herculean feat.

In fact…

The best rep I ever hired "only" hit 96% at her last job.

Yet she was #2 on a team of 50.

That tells a bit of a different story than "just 96%," doesn't it?

  • How often did they repeat previous mistakes?

If you handled these interviews right, you asked about mistakes they’ve made in their roles.

You want to see if they REPEATED those mistakes in subsequent roles.

If they did, “eyes wide open” is the best advice I can offer.

  • What ACTUALLY drives them (and is it different than what they SAY)?

This is why you ask why they took certain jobs. And why they moved on from others.

It helps you get a sense of what truly motivates them over the long term.

  • What was their relationship like with past bosses?

Most A-Players have strong relationships with their past bosses.

Not always. But most of the time.

  • What did they like and dislike about previous roles?

How well does that align with the role you’re hiring for?

Here’s what to do next (PLUS bonus questions)


By now, you’ve got a powerful sales hiring technique at your disposal.

One that’s responsible for repeatedly hiring President’s Club-grade sellers.

You’re now better than 99% of sales managers at hiring.

I wish I were kidding.

But… I have a confession to make:

I left out a few CRITICAL questions

That’s right.

There are 1-2 more questions you want to layer in per role.

They are questions that assess soft traits. Things like:

  • Grit
  • Coachability
  • Self-awareness
  • And more

Why didn’t I include them here?

Because those traits are unique to YOUR hiring profile.

Different sales roles hire for different traits.

So instead, I created a MASTER list of interview questions, free.

It’s organized by traits.

You simply click the trait you’re hiring for and BOOM:

You get a list of proven questions that help you screen for that trait.

So here’s what I want you to do.

First, download the master list of interview questions.

It’s free.


Select no more than 1-2 “mission-critical” traits you want to screen for.

Click on those traits in the cheat sheet.

And add those questions to your chronological sales interviews.

Repeat for each role.

THAT will help you see patterns like you wouldn’t believe.

Download the free cheat sheet here.

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