Are You Making These 7 ‘Terrifying’ Sales Hiring Mistakes?

Are You Making These 7 ‘Terrifying’ Sales Hiring Mistakes?

Sales Hiring
Chris Orlob
October 30, 2022

These sales hiring mistakes are just that: terrifying!

How many of these sales hiring mistakes are YOU making?

If you stop doing these, you’ll hire better sellers and attrit less.


Once you learn what NOT to do, I have a bonus for you at the end of this post:

How to hire SaaS reps that sell like crazy.

ONE: Hiring too far outside of your ‘sales motion’

How long is your sales cycle?

How big are your deals?

And what’s involved in closing those deals (buyers, pilots, etc.)?

Hire people who have as close to that experience as you can.

Success with a similar sales motion is one of the best predictors of AE success.

If you’re selling $250,000 deals with a 6 month sales cycle, then avoid hiring a rep who closes $40,000 deals in a 30 day sales cycle.

They may succeed. I’m a big believer in human potential.

But odds are, they won’t.

TWO: Hiring a rep JUST because they match your ‘sales motion’

This is the corollary of number one.

Yes, you want to hire people that have experience with your deal velocity and sales motion.

But that’s not an automatic ticket to win.

Really, it’s more of a ticket to play the game.

I see this all the time. It’s the ‘Halo Effect’ in full play:

Sales leaders overlooking red flags that would otherwise be deal-killers.

Because ‘industry experience’ seduces them.


What if they SUCKED at those previous jobs?

Ever think of that?!

That’s why the BEST ‘ideal rep profiles’ have three sections:

All of them matter.

So hire for all of them.

THREE: Taking a candidate’s past achievements at face value

A friend of mine is VP Mid Market Sales at a company you’d recognize.

He called me to backchannel a rep he was about to hire…

One that I hired in a previous role.

Him: “We’re about to move forward with her… any red flags?”

Me: “uhhh… yeah. She was one of the worst hires I’ve made.”

Him:What?! You’re kidding me? She said she hit 170% of her number in the 15 months she worked at your company and auto-qualified for President’s Club. So what’s the problem? I’ll take those achievements if the con is she’s just hard to manage or something…”

Me: “So would I. Problem is, none of what she said is true. She was PIP’d twice and eventually let go. The only time she made her number was on ramp. And that’s because she inherited existing customer accounts that bought more regardless of who managed them.”

I can’t make this stuff up.

People lie. Get used to it.

When you see crazy achievement numbers… that’s great!

But be sure to dig in. Don’t immediately accept them.

They’re easy to spin a story out of.

FOUR: Take a candidate’s attainment numbers at face value

Mediocre sales people tell ‘white lies’ in interviews (and on resumes).

Here are a few examples:


Resume: “I achieved 300% of quota.”

Reality: “That quarter was a ramp quota and I closed a bluebird.”


Resume: “Closed [huge enterprise logo, like Workday]”

Reality: “Closed a $10k startup owned by Workday”


Resume: “Closed the biggest deal in company history.”

Reality:Worked the biggest deal in company history… long enough for it to be mismanaged so poorly that upper management took over, while managing me out.”


Resume: “Consistently one of the top producers on the team.”

Reality: “I was #1 on a team of three for two of four quarters.”


Resume: “One of the top revenue producers in the company.”

Reality: “I’m counting renewal dollars in that number, which was most of it.”


Resume: “Consistently above quota.”

Reality: “Consistently above quota. But so was everyone. It was a HOT company, and average attainment was 110%. In reality, I was in the lower half.”


Resume: “Pacing for 150% this year.”

Reality: “Forecasting 150% this year.”

Learn how to cut through the clutter here:

FIVE: ‘Random acts of interviewing’

This is the #1 interviewing mistake that sales leaders make.

Random acts of interviewing.

This creates noise rather than signal.

Random acts of interviewing is where you:

  • Ask different questions to each candidate
  • Ask questions in different orders
  • Ask questions that don’t predict future behavior

On the other hand, predictive questions cut through the clutter.

There’s a lot of information you can get from candidates. Some of it relevant, some of it not:

Predictive interview questions help you zero in on the things that matter.

Much like a search engine.

There are three elements of predictive interview questions:

Need a few examples?

Read more about predictive interview questions here.

SIX: Asking ‘what would you do’ rather than ‘have done’?

Want to know a sales hiring secret some people hate?

Look, I get it.

People have potential that doesn’t always match their pasts.

Even lowly prison inmates can rise to great lives of character and achievement.

But your job as a sales leader is not to ‘take a chance on people.’

It’s to play the odds.

It’s to produce results for the business.

And in general (read: 98%+ of cases)...

Past behavior does predict future behavior.

2% of the population defies that rule.

Are you willing to take a chance with 2% odds?

In life… yes. Sometimes.

But in sales hiring… no thanks. Hard pass.

SEVEN: Form conclusions too early

Want a slam-dunk guaranteed way to make a STUPID hiring decision?

Form a strong conclusion about a candidate too early on (like mid interview).

A few weeks ago, I was interviewing an enterprise AE candidate.

He didn’t make a strong first impression. I didn’t really connect with the guy.

So I made a dumb mistake of intrepreting all of his successes as luck.

And I was EXTRA critical of his past mistakes.

Dumb move on my part. Turns out he’s a strong hire.

On the other side of the coin…

I was interviewing another enterprise AE candidate.

LOVED her. She had a magnetic personality!

Decided I wanted to hire her within the first few minutes of the interview.

Big mistake.

I ignored SO MANY red flags during the rest of the interview because I jumped to liking her too fast.

Luckily, I have smart colleagues who called me out about that, and we passed on her.

But lord, it’s easy to make dumb mistakes when you jump to conclusions about a person too fast.

Grow Your Sales Leadership Skills


So there are the mistakes to avoid.

What about what TO do?

Start by asking bullet-proof interview questions.

Here’s a (free) list of 91 interview questions that PREDICT sales success.

Swipe and steal them here.