Salespeople tend to get pretty good at interviewing. It makes sense. They spend their careers learning how to build rapport, understand an audience, present information clearly, and handle objections. The more experienced the salesperson, the more interviews they have probably been through, and by the time they are sitting across from you, they have usually answered the standard questions many times.
You still need those questions. At SalesFirst, we spend a lot of time on quota attainment, rankings, sales cycles, deal sizes, prospecting activity, pipeline creation, and the other measurable parts of somebody's sales history. A polished candidate can tell a good story about almost anything, so we want enough detail to understand what they actually did and how well they did it.
Once we understand that part, though, we like getting the candidate a little bit off script.
We don't mean trick questions. We've never understood what we're supposed to learn by asking somebody how many golf balls fit inside a school bus or what kind of animal they would be. We mean reasonable questions that the candidate probably hasn't rehearsed. Good ones usually make somebody stop for a second, think, and then have a normal conversation with us.
Here are 15 that we like.
1. Who had a big influence on the way you work, and what did you pick up from them?
This can go in a lot of directions, which is part of why we like it. Somebody might talk about a parent, coach, teacher, first manager, grandparent, colleague, or anybody else who mattered to them.
Usually the qualities they choose are more interesting than the person. Work ethic, patience, competitiveness, discipline, humor, ambition, generosity. From there we'll normally ask which of those qualities they think they picked up themselves.
It's a much more natural conversation about character than asking somebody to tell us their three greatest strengths.
2. Tell us about the best salesperson you've ever worked beside. What could they do that you couldn't?
Most good salespeople have worked around somebody who raised their standards. We want to hear what made that person unusually good.
Then we want the harder part. Can the candidate identify something another salesperson genuinely did better than they did? Some people are very comfortable admitting that. Others will give an answer and immediately start explaining why they were actually just as good.
That tells us something too.
3. What part of your sales process would your last manager say you occasionally tried to skip?
Asking somebody if they're coachable doesn't get you very far. Almost everybody says yes.
Experienced salespeople develop preferences, and those preferences eventually create blind spots. Somebody loves discovery but hates call preparation. Somebody prospects all day but lets the CRM become a disaster. Another rep develops fantastic customer relationships but procrastinates on administrative work.
We don't expect somebody to tell us they have no bad habits. We'd rather hear that they know exactly where theirs tend to show up and what they've learned to do about them.
4. When was the last time another salesperson made you jealous?
We don't think a little professional jealousy is necessarily unhealthy in sales.
Another rep lands the account you wanted. They make more money. They get promoted. They handle a call better than you would have. They make something difficult look annoyingly easy.
What somebody does with that feeling can lead to an interesting conversation. Do they study the other rep? Ask questions? Work harder? Sulk for three days?
That usually tells us more about competitiveness than asking, "Are you competitive?"
5. Tell us about a customer you probably should have walked away from sooner.
Salespeople spend a lot of their careers being told to persist. Eventually, the good ones also learn when persistence has stopped making sense.
Maybe the customer was never qualified. Maybe the salesperson ignored obvious warning signs because the deal was big. Maybe they spent months talking to somebody who couldn't actually make a decision. Maybe they closed the account and later wished they hadn't.
A salesperson who has been doing this for a while should have some scar tissue here. We want to hear what they missed and whether they would recognize it sooner today.
6. What's some common sales advice you disagree with?
We particularly like this one with experienced candidates because, at some point, you should develop opinions about your profession.
Maybe they disagree with a prospecting technique, a closing strategy, a management philosophy, or something they learned during formal sales training. We don't care whether we agree with their answer.
We do care whether they can explain why they believe it.
There's a difference between somebody who has practiced sales long enough to develop judgment and somebody who has simply accumulated a large vocabulary of sales concepts.
7. If we called the person who sat next to you at your last company, what would they tell us you were unusually good at?
Candidates have rehearsed answers about their strengths. They usually haven't spent much time preparing an answer about how the person in the next cubicle experienced working with them.
Sometimes the answer is directly related to selling. They were great at prospecting, knew how to rescue a difficult deal, or always had an unusually clean pipeline.
Sometimes it isn't. They were the person everybody asked for CRM help. They kept the team loose when things were going badly. They reviewed important proposals. They helped new reps.
Quota tells us a lot about a salesperson. It doesn't tell us all of that.
8. What's something your last sales manager repeatedly coached you on that you still haven't completely fixed?
Adults are complicated. Sometimes you can understand feedback perfectly well and still spend years trying to change the habit behind it.
We like candidates who can acknowledge that.
The conversation usually becomes more useful when we ask what they've actually done about the problem. Maybe they've improved quite a bit. Maybe certain situations still bring the old habit back. Either answer can be perfectly reasonable.
A person doesn't have to present a weakness that has been conveniently solved just in time for the interview.
9. Tell us about a deal you lost that you still think about.
Wins are easy to talk about. Lost deals tend to require a little more reconstruction.
We usually follow this one pretty aggressively. When did you first suspect you might lose it? Who was actually making the decision? What did you misunderstand? Was there a point where you could have changed the outcome? What would you do differently now?
Experienced salespeople usually have a few losses they can still replay in their heads. We're less interested in whether their diagnosis is perfect than whether they've actually thought seriously about what happened.
10. What would have to happen for you to miss quota here?
This is partly a sales question and partly a job-fit question.
The candidate has to think about the conditions they need in order to perform. Territory matters. Ramp time matters. Product training, lead flow, sales leadership, pricing, marketing support, and the existing reputation of the company can all matter.
Some expectations will be completely reasonable. Others may tell us that the environment where this person has historically succeeded is quite different from the one we're hiring them into.
We'd rather discover that during the interview than six months later.
11. What's the most boring part of being good at sales?
A lot of professional selling is repetitive. Prospecting, follow-up, CRM work, account research, preparing for calls, updating the pipeline, and doing the important thing again even though you did it yesterday and nobody is going to congratulate you for it are all part of the job.
People who have actually become good at sales normally know which part bores them. The useful conversation is how they make themselves do it anyway.
12. Tell us about a time you thought your manager was wrong but followed their direction anyway.
Disagreeing with your manager isn't particularly unusual. Knowing what to do after the disagreement can be harder.
Sometimes you should push back. Sometimes you make your case, lose the argument, and execute the decision anyway. Occasionally the issue is important enough that you shouldn't simply go along with it.
We want to hear how the candidate made that distinction in a real situation. It usually opens up a good conversation about judgment, hierarchy, ego, and how somebody behaves when they don't get their way.
13. What kind of customer brings out the worst salesperson in you?
Everybody has buyers they naturally connect with and buyers who require more work.
An analytical rep may get frustrated with an owner who wants everything reduced to a two-minute conversation. A very relationship-oriented salesperson may dislike a formal procurement process. Somebody who loves complicated discovery might lose energy in a highly transactional sale.
None of those automatically make the salesperson wrong for the job. But if the customers they struggle with happen to describe most of your customer base, you probably have something worth talking about.
14. If you weren't allowed to tell us your quota attainment, how would you prove you're good at sales?
We ask about quota constantly. We should. But we still like temporarily taking the obvious scoreboard away.
Now the candidate has to decide what other evidence counts.
Maybe customers followed them to another company. Maybe they were promoted repeatedly, given the hardest accounts, asked to train new reps, trusted with larger territories, or expected to create most of their own pipeline. Maybe there's something else entirely.
The evidence somebody chooses can tell us quite a bit about how they define being good at the profession.
15. If we hire you and we're sitting here a year from now talking about why it didn't work, what do you think happened?
This one usually creates a pause.
The candidate has to think about the job, think about themselves, and imagine where the two might fail to line up. That can uncover concerns that haven't appeared anywhere else in the interview.
We don't hold legitimate risks against somebody. We'd actually be more skeptical of a candidate who couldn't imagine any circumstances under which the job might not work. Experienced people usually understand that hiring has too many variables for that.
What We Do With the Answers
We wouldn't ask all 15 of these in one interview, and we wouldn't turn them into a personality test where there's secretly one answer we're hoping to hear. We'd pick a few that seem appropriate for the candidate and the position and leave enough time to follow the conversation.
The follow-up questions are usually where we learn the most. Ask why. Ask for an example. Ask what happened next. If the first answer sounds unusually polished, stay with it for a while. Salespeople are professional communicators, so an interviewer has to get past presentation eventually.
That's also why we wouldn't replace the normal sales questions with these. We still want quota, rankings, KPIs, activity, sales cycle, deal size, pipeline generation, and actual results. Those give us evidence that the person has done the work. Our own sales interview process is deliberately structured around those details because they give us something concrete to evaluate.
These unusual questions serve a different purpose. They give us a chance to understand how somebody thinks, where they're self-aware, what they've learned from other people, how they respond to failure, and what working with them might actually be like.
Used together with the measurable questions, they tend to leave us with a much better understanding of the person we're considering hiring.
