Every Great Sales Interview Is Really Two Interviews

Most founders walk into an interview focused on one decision: Should I hire this person? They want to know whether the candidate can do the job, whether they can sell, whether they'll fit the team, and whether their past performance is real.

The best candidates walk into the same interview trying to make a decision of their own: Should I work here?

That changes the entire interview.

You're evaluating their experience, preparation, listening skills, numbers, and ability to sell. At the same time, they're evaluating the opportunity, the company, the role, your team, and you.

That's why every great interview is really two interviews. If you get good at evaluating candidates but never learn how to help great candidates evaluate you, you can run a great interview process and still lose the people you want to hire.

Why Great Candidates Are Interviewing You Too

This becomes especially important when you're trying to hire someone who's already performing. The best salespeople usually aren't sitting around waiting for someone to give them a job. They may be hitting quota, making good money, working for a leader they like, and building something somewhere else.

If you want them to leave, you're asking them to trade something they know for something they don't.

Founders sometimes forget that because the traditional interview process puts the company in the position of power. The company has the job. The candidate wants the job. The company asks the questions and eventually decides whether to make an offer.

That dynamic changes when you're recruiting great people.

Now the candidate has something you want too. They have performance, experience, relationships, and options. While you're trying to determine whether they're worth hiring, they're trying to determine whether your opportunity is worth leaving their current job for.

Neither side should be trying to win the interview. Both sides should be trying to get enough information to make the right decision.

Start With the Truth

One of the first things a good candidate should want to understand is why the position is open.

If you're hiring because the company is growing and you need more sales capacity, tell them. If this will be your first salesperson and you've been doing all the selling yourself, explain that. If you're replacing somebody who didn't work out, don't dance around it.

That last one is where founders sometimes get uncomfortable.

Maybe the previous rep couldn't build enough pipeline. Maybe they needed more structure than you could provide. Maybe the territory wasn't as strong as you thought it was. Maybe you hired the wrong profile.

Maybe you screwed up too.

Tell the truth.

Strong candidates don't expect every company to be perfect. They're trying to understand what they're walking into and whether they can be successful there.

There's also a practical reason to be direct. If something about the role could cause the candidate to turn it down, you want to know that before you've spent weeks interviewing them.

Don't hide something they'll eventually find out anyway. If you've had turnover on the sales team, be prepared to talk about it. If the territory has been difficult, explain why. If quota is aggressive, explain how you arrived at it. If the last salesperson failed, explain what happened and what you've changed.

You're not trying to get someone to accept an offer before they discover the truth.

You're trying to find someone who understands the truth and still wants the job.

That's a much better hire.

Pay Attention to How They Interview You

While the candidate is evaluating you, you should be paying close attention to how they're doing it.

One of the easiest things to notice early in a sales interview is what the candidate asks about the company.

How many employees do you have?

How long have you been in business?

Have you raised funding?

None of those questions automatically knock someone out. But most candidates can find those answers in about a minute before the interview.

For a salesperson, that matters.

If somebody is interviewing for a sales role and didn't spend a few minutes researching the company before the conversation, it's reasonable to wonder how they're going to prepare before an important prospect call.

There's also a big difference between asking, "Have you raised funding?" and saying, "I saw you raised $12 million last year. How has that changed the sales team?"

Both candidates are interested in the same thing.

One is asking you for information they could have found themselves. The other did the research and used what they learned to ask a better question.

That's what good salespeople do before talking to prospects. Research isn't valuable because you can prove you did it. It's valuable because it helps you have a better conversation.

I also pay attention to the questions candidates couldn't possibly have prepared before the interview.

Maybe you mention that you changed the comp plan this year. Fifteen minutes later, the candidate comes back to it:

"Earlier you said you changed the comp plan. What wasn't working with the old one?"

That's different.

They weren't just waiting for their turn to talk. They were listening, processing new information, and following up on something that mattered.

Those are all things I want a salesperson to do with a prospect.

Why Should They Pick You?

Founders spend a lot of time trying to answer one question during an interview: Why should I hire this person?

Spend some time on the opposite question too.

Why should this person pick us?

If you're recruiting somebody who's already successful, "We have a great culture" probably isn't enough. Neither is a job description full of words like fast-paced, innovative, disruptive, and unlimited earning potential.

What is actually compelling about the opportunity?

Maybe they'll get to build something instead of inheriting an established territory. Maybe they'll work directly with the founder. Maybe the product solves a problem they understand and believe in. Maybe there's a legitimate path into leadership. Maybe the economics are substantially better. Maybe they'll have more autonomy. Maybe the company is at a stage where one great salesperson can have an enormous impact.

Whatever it is, know it.

A founder should be able to explain why a successful person would leave a good job to join the company. If you can't articulate that clearly, it's going to be difficult for the candidate to figure it out for you.

But selling the opportunity doesn't mean pretending everything is amazing.

If pipeline is a challenge, say it. If the sales process still needs work, say it. If you're still heavily involved in closing deals, say it. If you're hiring someone partly because you need them to help build something that doesn't exist yet, they need to know that too.

Then explain the opportunity inside the problem.

There's a big difference between saying, "Our sales process is a mess," and saying, "We've proven customers will buy. I've been doing most of the selling myself, and now we need somebody who can help us turn what I've been doing into a repeatable sales motion."

You're not hiding the problem in the second version. You're explaining what has already been proven, what still needs to be built, and what the person you're hiring will actually own.

For the right salesperson, that may be exactly what makes the opportunity interesting.

For the wrong salesperson, it may be exactly why they decide not to take it.

Both outcomes are useful.

The Candidate Experience Is Part of the Interview

One of the strongest candidates I'd interviewed in months made this very clear to me.

The team loved her. I was ready to move her forward.

The next morning, she called me. Not to negotiate and not to ask about salary.

She wanted out.

When I asked why, she told me nobody in the room seemed excited to be there. Nobody sold her on anything.

I didn't have a great answer.

The company had spent the entire interview deciding whether they wanted her. They forgot she was deciding whether she wanted them.

By the time she called me, she'd already made the decision.

That's candidate experience.

It isn't just how quickly you schedule the interview or whether somebody sends a nice follow-up email. It's the experience a candidate has while they're trying to determine whether they want to spend the next several years of their career with you.

Every person they meet gives them information. How you describe the company matters. How your team talks about each other matters. How you talk about the person who previously held the role matters. Whether anyone seems genuinely excited about where the company is going matters.

You're giving the candidate evidence throughout the entire process.

They're paying attention to it.

One More Thing

You should absolutely pressure-test candidates.

Dig into their numbers. Ask why they won and why they lost. Understand how they build pipeline. Find out what they do when things go wrong. Pay attention to whether they prepared for the interview and whether they're actually listening once it starts.

Just remember that while you're doing all of that, there's another interview happening at the same time.

The candidate is evaluating the role. They're evaluating the company. They're evaluating your team. And they're evaluating you.

The stronger the candidate, the more likely they are to have options.

So lead with the truth. Be clear about the problems. Know why the opportunity is worth considering. Give them enough information to make the same informed decision you're trying to make.

You're deciding whether you want them.

They're deciding whether they want you.

Every great interview is really two interviews.

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