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Salespeople: These 22 Questions Guarantee You'll Pick Winning Companies to Sell For

Chris Orlob
August 26, 2022

Seth's text read in the glow of the night.

"Hey, can we talk?"

It was 11 pm.

Seth was a successful, high-income SaaS AE I tried to recruit three months earlier.

But my recruiting efforts failed. He chose another company.

At first, he was excited by the new opportunity.  I wished him well.

But as the months passed, it became clear it was a mistake.

The culture didn't respect salespeople.

The comp plan seemed great on the surface. But no one was hitting quota. So the OTE was a mirage in the desert.

Seth was oversold, and he felt stuck.

"I think I chose wrong. I dread starting work every morning. Would love to revisit our conversation if you've got a spot open."

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Have You Ever Been Here Before?

Have you ever joined a company, only to wake up months later miserable and drained?

Have you ever been "oversold" by a hiring manager?

Have you ever dreaded going to work because you picked the wrong company?

Happens every day.

You Can Avoid This By Asking Great Questions

You'll know exactly what you're getting when you learn to ask the right questions.

A hiring manager's job is to SELL.

They are under enormous pressure to fill headcount.

Especially when their company is growing fast.

If they don't have enough reps, they don't make their numbers.

When you learn to ask questions that get to the heart of their sales situation, you'll PREDICTABLY join companies that have an environment where you'll CRUSH it.

So here are 22 questions that will reveal everything you need to know about the companies you're interviewing with.

Market Dynamics & Sales Process Questions

Start with these questions. For two reasons.

First, your success is TIED to the market dynamics!

Great sales execution with poor market dynamics is like trying to chop down a tree with a dull axe.

Great sales execution with HOT market dynamics is like cutting into butter with a hot knife.

Second, these questions will impress the hell out of the hiring manager.

What kind of market type are you in?

  • Are creating a new market, entering an existing market, or reinventing an existing market?

Each of those three market types offer VERY different experiences as a sales professional.

In new markets, you usually have to EDUCATE and EVANGELIZE your problem and solution.

This is an incredibly difficult skill.

Plus, if the company is light on funding, they've got a long (losing) road ahead of them (unless they have heavy fundraising plans).

New categories are created with financial war chests.

On the flip side, if you're entering an existing market with existing incumbents, the product BETTER have a powerful unique advantage.

Otherwise, you'll be beating your head against the wall.

What's unique about selling to your market and buyer personas?

Selling to a Head of Sales and a Head of IT demand different skills.

Do they match with yours?

You're also looking at the quality of their answer.

Well-led sales organizations have clear answers about this kind of stuff.

They aren't generic.

On a scale of 1-10, how would you rate your product/market fit? How do you know? What's missing?

No need to run for the hills if they don't have perfect product/market fit yet.

But avoid those who give you a "10/10" answer without any evidence to back it up.

How would you rate your company, product, and go-to-market against your competition? Why do you say that?

Here's something I'm SURE is going to get me in trouble for saying one day:

Every company's job is to win at all cost against the competition.

Great wealth only goes to the leaders in the space.

This question will give you a sense of how strong the horse is in the horse race.

A much better question than "Who's better? You or your competition?"

The more concrete the answers, the better.

How do you win against your competition?

Straight forward enough.

Weak answers will mean weak competitive abilities. Plain and simple.

If you were your competitor, what would you do to win against your company?

And now you know both sides of the competitive equation:

How are they winning?

And where are they vulnerable?

You'll have so much insight after asking both of the last two questions.

Who are the blend of buyer personas you sell to? How do you best navigate them to win deals?

Every B2B sale has multiple buyer types within a single deal.

Great sales teams think critically about HOW you blend these people together to get a deal done.

Who do you start with?

Who do you develop into a champion?

Who do you try to box out of the decision process?

What are the three top reasons you lose deals?

The value of this question is self-evident.

You'll learn a tremendous amount by this one alone.

Leadership, Culture, & Development

What function does your CEO favor the most, and can you give me an example?

You don't always have to work for a hard-charging, sales-driven CEO.

But you definitely don't want to work for a CEO who doesn't get sales. Doesn't like it. Doesn't respect it.

Culture cascades down from the top.

If I talked to the most recent 2-3 people that left, what would they tell me about why they left?

Notice the question isn't phrased as "what's the most common reason people leave?"

That's because you'll be getting the hiring manager's opinion.

Instead, you want the perspective of the people who actually left. That's what matters.

Notice this question has an assumption built into it: That you plan on talking to a few people who left recently.

That forces the hiring manager to give an honest take.

How many reps have you promoted from within in the last year?

Again, notice the phrasing.

It's not "Do you believe in promoting from within?"

Of course. Everyone is going to say YES to that!

So instead, you ask for evidence: How many have you promoted recently? What's their story?

How many people have you hired that were referrals from your existing team?

The more the better.

It speaks to a few things:

One, people love it there and encourage their friends to come along.

Two, they have a team-oriented culture.

What's the most recent negative feedback your boss has given you? What about one of your reps?

Self-aware, humble managers have great answers to this question.

And self-aware, humble managers are a joy to work for.

If they haven't received any recent feedback, are they coachable?

If they aren't coachable as a leader, what does that say about their culture?

What kind of coaching will you get?

Probably not much.

Can you walk me through how you onboarded your most recent hire during their first 90 days?

Unless you're talking to an early stage (Series A or earlier) startup, hiring managers should have very strong, detailed answers here.

If they do, you'll be set up for success.

If they don't, you'll be thrown into the deep end and expected to figure it out on your own.

That's fine if that's what you want. But know what you're getting.

Can you walk me through your most recent successful coaching engagement with one of your reps?

Do you see a trend here?

I'm encouraging you to ask questions that ask for RECENT examples.


THAT is how you get the truth. Not by asking hypothetical questions like "Do you coach your people?"

If they can't answer with recent examples, they probably don't coach much.

Performance, Quota, and Comp Questions

Ah... What you've been waiting for...

Questions about MONEY and SUCCESS!

Before we get into these question, I have two rules for asking these:

  1. Do NOT lead with these questions. They say the wrong thing about you as a candidate.
  2. Do NOT join the company until these questions have been asked!

Now that I've fried your brain with two conflicting rules, have at 'em:

How has your team performed over the last 12 months? How are you trending?

A rising tide lifts all ships.

Join teams that are trending in the right direction.

If they've been missing their numbers, it's not a deal killer.

In fact, it may be an opportunity.

But the TREND of how they are progressing (or declining), matters greatly.

What percentage of your team exceeds quota?

A big OTE is great... until you realize no one's hitting quota.

You're looking for betwee 50-80% of the team.

If it's less than 50%, then you have a "losing locker room," where most people aren't making their numbers. Bad news for culture.

If it's more than 80%... that's great. But expect a quota increase in the future.

What's the "math" that gets someone to quota?

This one has a few follow up questions to it:

  • What is quarterly/annual quota?
  • What's your average deal size?
  • What's your win rate?
  • What percentage of new opportunities are marketing or SDR-sourced vs. AE self-sourced?

You're looking for math that works.

If you've got a $1M quota, but a $5k average deal size, that's 200 deals! Over 16 transactions per month! Probably not attainable.

How is quota structured?

Get clear on what kind of revenue "counts" toward quota.

Example: If you have an $800k quota, does new business AND upsell count? Or is that purely a new business quota?

Know what you're getting going in.

What does ramping quota look like? How have your new hires performed against that?

There's nothing worse than having an unattainable ramp time.

Starting off "in a hole" is a horrible experience.

Of course, you're not looking for an "easy win" with ramp.

But if you've got six months to start producing full quota, and the sales cycle itself is six months.... Red flag.

What separates your highest quota attaining reps from everyone else?

This question helps you assess the quality of the manager.

If they have a weak point of view here... they probably can't replicate success across their team.

And that's a manager's job.

What are the top three root causes of why reps miss quota?

This, again, helps you assess the quality of manager.

If they have no point of view here, consider this one a yellow flag.

Not a deal-breaker by itself. But come on... you should know these things!

Can you tell me the details of the comp plan?

Simple enough.

Don't join companies without knowing how you get paid first.

Especially if you've asked all of the above quota attainment-related questions, this one puts the cherry on top of the cake.

What were the last few changes you made to the comp plan?

Some sales organizations are MOVING TOWARD paying their salespeople even more!

And some... are moving toward paying their salespeople less and less.

If the last 2-3 changes to the comp plan were effectively pay cuts, then it better be a damn good opportunity to justify the tightening anaconda squeeze.

On the other hand, a comp plan that's progressively getting BETTER doesn't ALWAYS mean it's a good thing!

WHY are they continually paying out more?

Businesses make business decisions. They don't do these things for fun.

Maybe they're just an awesome, sales-centric culture and want to attract the best of the best.

But maybe they have a turnover problem.

Worth digging in.

Can you please share this post on LinkedIn?

If you enjoyed this...

If you found it helpful...

Someone else might too.

Can you pay it forward and spread the word?

Share it out on LinkedIn so other salespeople can join great companies.

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