The Grit Interview: How to Hire Salespeople “Hell Bent” on Success

The Grit Interview: How to Hire Salespeople “Hell Bent” on Success

Sales Hiring
Chris Orlob
July 24, 2022

Are you looking to hire salespeople with GRIT?

Reps that will run through walls to achieve success?

Grit is the most prized sales rep attribute.

It’s also the easiest to bullsh*t. And the hardest to hire for.

You’re about to learn a 20-minute technique that screens for grit with accuracy.

But first… a WARNING.

This technique is ONLY for those who prize grit above all else.

Grit must be your number one trait for this to work.


Because I’m asking you to dedicate a 20-30 minute interview for grit.

There are two situations where this works

The first one? You START your hiring process screening for grit with this interview.

You care about grit SO MUCH, that if people don’t have it, they’re out.

Regardless of their other assets.

The second situation: You do this interview toward the END your hiring process.

I call this a Targeted Interview.

I teach how to do these, step by step, in my Sales Hiring Masterclass.

In that case, you’re sold on the candidate in all areas.

But want to TRIPLE CHECK that they have what it takes in the grit department.

Either one of those works.

Now let’s talk about how to do it.

Follow these steps exactly. Do not veer from them until you’ve done this at least 30 times.

Only then can you break the rules.

P.S. At the end of this post, I have three free bonus tips.

Sign up for the free interview cheat sheet, and you’ll get the three tips delivered:

Step 1: Outbound Email Sniff Test (5 min)

It is important to START with this step.

If you do this out of order, this step becomes “tainted.”

You’ll see why later.

Here’s how it goes.

Explain to your candidate that you hire people with the tenacity to keep up an outbound habit.

Even if they have SDRs.

This talk track works great. Feel free to swipe it:

The rep will nod her head.

Then ask:

“With that in mind, how much time do you spend sourcing your own pipeline these days?”

There are three buckets of answers:

“Not at all.”


This is going to sound unfair…

Gritty people are always hunting for new opportunities. Period.

The only exception is if they’re “checked out” of their job.

I’m yet to meet a gritty salesperson who sits back and waits for someone else to feed them.

Even if that someone feeds them well.

“Not as much as I used to.”

This answer sounds bad.

But actually, lots of top producers answer this way.

If your rep answers this way, keep probing.

Ask for their most recent example, even from a month ago.

Keep interviewing them.

But keep them on “probation” for the rest of the interview.

Guilty until proven innocent.

“All the time.”

If the rep answers with this, now you test them.

Here’s what you do next:

“Great to hear. Can you show me an example right now of an outbound message you’ve recently sent that helped you get a meeting?”

I’m shocked at how many people can’t.

Pass on them.

If they CAN show you something impressive, you may have a star on your hands.


Step 2: Ask the “drive” question (to save for later)

ONLY after you’ve started with the outbound test do you go here.

Fair warning:

This step, by itself, predicts self-awareness. Not grit.

But used in combination with the rest of the steps in this post, it will play its part in helping you assess grit.

Here’s how to do it.

Ask the candidate:

“What drives you? Why? How has that shown up in your life in the last week?”

Get answers to all three parts.

There are two keys to probing after this question that help surface grit

(or lack of it):

First, peel back the onion on WHY.

If they say “I’m driven by money!”... why?

So you can collect pieces of paper and digits on a screen?

Get to the WHY.

Second… and this is the key… you are looking for recent behavior.

It’s easy for someone to give an inspiring answer to “what drives you?”

“Change the world, boss!”

It’s harder for someone to show behavior of that drive in the last week.

Here’s a (good) example

I asked this in an interview last month.

The rep answered with:

“I grew up poor. Watched my mom cry over money. I want to create generational wealth for my family.”

So far so good.

Pretty inspiring.

He answered the “what” and “why” in the same breath.

Then I asked:

“How has that drive influenced your behavior recently? Show me an example of behavior you’re doing that proves to me that drives you in a big way.”

Here's how he answered:

“Well. Three things come to mind:
I work 10-11 hours a day. Sure, it’s not 80 hours a week. But it’s a lot. And it’s productive.
I spend my nights and weekends learning. I won’t go to bed unless I’ve read 10 pages of a book or 30 minutes of an audiobook.
I invest 40% of my net income in index funds and real estate”

GOOD answer.

Few people can SHOW commitment to what drives them like that.

Gritty people ACT on their drive.

Other people have inspiring drives. But do not honor them.

Recent behavior is the key.

Here’s what to do with the answer

Take their answer.

Put it in your back pocket.

And use it as a lens through which you assess the rest of the interview.

You should have about 20 minutes left.

Their answer to “what drives you and why” is now an ongoing congruency test.

You’re going to spend the rest of the interview asking questions designed to draw out their behavior.

And you’ll compare their behavior to their answer to their “drive” question.

If they’re incongruent, pass.

If they match up, let ‘em keep going.

Step 3: Ask predictive questions that break down the “ingredients” of grit


You’ve done the outbound test.

And you’ve probed the rep’s drive.

Now here’s the meat of the interview.

You’re going to ask a series of predictive questions do two things:

  1. Identify patterns of grit behavior
  2. Compare the patterns to what the rep said drives them

Here’s a summary of what makes an interview question “predictive”:

Now, to do this well, you have to recognize a simple fact:

Grit isn’t a single trait.

It’s a combination of several, including:

  • Passion
  • Perseverance
  • Ambition
  • A habit of “getting shit done”
  • Work ethic

Let’s get to the questions.

After we get through them, I’ll help you put the pieces together.

Tell me about the areas in your life where you’ve achieved excellence. Or, tell me about your proudest achievements.

I’m yet to meet a gritty person who has not become REALLY GOOD at something.

Grit FUELS the drive to get better at a skill.

Great answers include:

  • Sales - becoming one of the best
  • Athletic achievements
  • Mastering a musical instrument
  • Building something
  • Academic achievements
  • Anything that requires disciplined practice

If they can’t tell you something impressive, pass.

What makes you think they'll be excellent here if they haven’t been excellent elsewhere?


Tell me about the top one or two stories of perseverance from your life or career.

Gritty people always have at least one good one.

Not because gritty people always come from hardship.

But because gritty people put themselves in situations where hard things come up!

It’s part of the territory!

Gritty people, regardless of background, pursue things that CREATE “hardship.”

Not hardship in the socio-economic sense.

But a daunting situation they had to surmount.

That most people would shrink from.

What kind of sacrifices have you had to make to get to where you are?

I’m not encouraging you to hire workaholics (though I do think we’ve taken this demand for work/life balance too far).

I’ve personally never worked an 80+ hour week (maybe once or twice).

But I consistently work 50-65 hours.

Over years.

Gritty people can rattle off similar sacrifices very fast.

“I wake at 6 am every day to prospect.”
“I sent follow up emails to my deals at 9pm after I put my kids to sleep.”
“I’ve spent thousands of dollars on personal development.”

These are answers from the best salespeople I’ve hired.

Gritty salespeople’s eyes will light up when you ask this. And they’ll be able to answer it.

Not because they wear “hustle culture” as a badge of honor.

But because they’re proud of what they’ve accomplished. And it took a lot to get there.

It wasn’t for nothing. THAT’S why they light up.

I’m waiting for the critics on this one.

My response:

If you want to hire sellers who don’t know sacrifice, go for it. You do you.

What are your career goals over the next one, three, and five years?

This is where you test for the right ambition.

Not too

Too much ambition can be a bad sign!!

If an ambition of building a multi-billion dollar company consumes them…

And they want to do that within five years…

And you’re interviewing them to be an account executive…


It’s not an immediate DQ.

But their ambitions might be too much for this job to satisfy.

But, if they “want to make enough to not stress about money and spend more time surfing…”

That might not be a powerful enough reason for them to run through walls.

Look for intermediate-range goals that are in between.

That align with what your role can deliver.

Long-range boundless ambition is fine. If they want to be a billionaire ten years from now, great!

But they have to see the IMMEDIATE path in your role for this to work.

Step 4: How would past bosses describe you?

As you come to a close, there’s one more thing you ask.

Let the candidate know you’ll want to talk to a few past bosses at some point.

When you do this well, it increases the odds of a truthful response for what comes next

It might sound like this:

“One of the things I’d like to do before we decide to work together is talk to a couple of your past bosses. Are you okay with that? Great.
Now you mentioned Jordan Robins was a previous boss. What are the top three words she’d use to describe you?”

Repeat this process with two more bosses.

Here’s the deal:

Gritty people always personify grit as their most dominant trait.

People know them for their grit (or a close cousin of “grit”).

So if their past bosses do not describe them as:

  • Gritty
  • Passionate
  • Determined
  • Relentless
  • Persistent
  • Resilient

…or anything like that, then they don’t personify grit.

It’s an accurate acid test and I’m yet to see it fail.

Step 5: Targeted reference check

Finally, you actually do reference calls to test for grit.

Get a couple of their previous bosses on the phone (ideally ones you select).

“What are their top 3-5 strengths, and what are their top 3-5 weaker points?”
“How would you describe her personality?”

Same thing as before.

If grit - or a close cousin of grit - does not come up…

They don’t personify it.

And if they don’t personify it… they don’t have it.

You can learn how to do reference checks that aren’t a waste of time in the Sales Hiring Masterclass.

Debrief the interview: How to assess their grit

There’s one word that will help you assess whether they have grit or not:


During this process, did you find that their previous behavior demonstrated grit?

It’s easy to talk a big game about how gritty you are.

Far harder to fake previous behavior that puts your money where your mouth is.

Here are a few questions:

  • How long have they stuck with things throughout their life?

It’s okay to hop around now and then.

But do they have a record of sticking with SOMETHING for a long time?

Gritty people do that.

  • How closely does their past behavior match what they say drives them?

Is it a bizarre mismatch?

Or are they congruent?

  • Did they have a concrete history of achieving excellence somewhere in life?

If not, pass. Simple.

  • Were you inspired by their stories of perseverance?

You already know why this is important.

Gritty people “run toward danger.” As such, they should have a few war stories.

  • Do they work hard and make sacrifices to reach their goals?

Being in sales is easy.

Succeeding in sales is very hard.

Do they do what it takes?

  • Duration of sticking with things for a while

Delay judgment until the end.

Once you have, score their “grit ingredients” on a scale of 1 to 5.

Don't skip this (I KNOW you want to).

Daniel Kahneman wrote about this in his book Noise.

This simple discipline “forces” you into objectivity.

Here are the traits to scale. One to five. Do it!

  • Passion
  • Perseverance
  • Ambition
  • A habit of “getting shit done”
  • Work ethic

Things should be clear for you by now.

Nail your interviews: FREE cheat sheet

Grit is one of the main traits that predict sales success.

But without others, reps can fail.




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