The jump from salesperson to sales manager is extremely challenging. Salespeople tend to act like entrepreneurs, running their own businesses and maintaining a book of clients. A manager has an entirely different job: Leading, inspiring, coaching, and training a team.
While the first role is self-directed and autonomous, the second role involves collaboration and working closely with others.
Whether you’re a salesperson trying to move up or an executive interviewing a candidate, it’s key to assess leadership potential.
Salespeople, prepare for these. Interviewers, ask these.
Leadership Interview Questions
1) “Tell me about a time you lacked the skills or knowledge to successfully hit a goal.”
This prompt encourages an honest, unrehearsed answer -- unlike leading questions such as, “Discuss a conflict with a coworker and how you resolved it” or “Give me an example of an obstacle you overcame.”
A good response will cover:
- The situation or task
- Why the goal was unattainable
- Lessons learned or results
Here’s an example:
“When I first moved into a closing role, I didn’t hit quota four months in a row. My activity was there -- but honestly, I needed more time as a BDR to get the fundamentals down. I actually asked to move back. It was pretty hard to admit I wasn’t ready. Yet after another four months, my confidence was way up and when I became an AE again, I actually hit or beat my quota every single month for three years.”
2) “How would you describe your leadership style?”
Some managers are hands off. Others like to be in the weeds with their reps. Some are prescriptive about every aspect of the sales process, from prospecting methods and soundbites to objection-handling techniques. Others don’t care how you do your job, as long as you’re meeting your number.
Every style has its place. This question helps determine whether the individual’s leadership style matches company culture and the demands of the role. If the team needs a “tough love” manager to whip them into shape, someone who’s relatively laid back and wants to be her reps’ peer probably isn’t the best fit. But if the team is functioning well, an authoritarian manager will breed resentment and probably damage its performance.
3) “Are there any team members you’ve enjoyed working with in the past?”
As a follow-up: “How would they describe your working relationship?”
A sales manager cannot act as a lone wolf, so it’s a huge red flag if the interviewee can’t think of a coworker. The more important answer, however, is actually the second. Describing herself from her peer’s perspective reveals a few things:
- Is the candidate self-aware?
- Is she empathetic enough to place herself in her team member’s shoes?
- What is her collaboration style like?
To illustrate, here’s a strong response. It’s detailed, authentic, and foreshadows how she’d act as a manager.
“Yes, I really like working with August, another salesperson on the Enterprise team.”
“August would probably say I’m good at giving feedback -- we spend two or so hours every week reviewing calls with each other -- and love celebrating others’ wins and boosting them up when their confidence is down. She’d also probably say I’m a little too easily frustrated. When I can’t immediately fix an issue in my sales process or approach, I’m angry with myself.”
4) “Imagine the CFO assigns a new team quota you know is undeliverable. It turns out, it was calculated based on revenue need -- not opportunities and resources. How would you handle this situation?”
A good leader acts an advocate for his team. He must speak up on their behalf when management is making a bad call and promote their interests. This question delves into a thorny yet unfortunately common issue: What would a manager do when he’s caught in between his team and his boss?
The optimal response would sound something along the lines of:
“First, I’d analyze the data: Average rep performance, territory penetration, stage by stage conversion rates, time to hire, time to ramp, sales velocity, and so forth. Then I’d present my findings to the executives, explaining what I thought was possible given our current headcount and historical performance. I’d propose an aggressive but realistic quota.
If the target wasn’t adjusted, I would come up with a plan to get as close as possible. I’d use sales contests, incentives, and other creative strategies to keep team morale high and hopefully boost results.”
5) “How will you earn the respect of your team?”
Salespeople need to respect their manager to follow her recommendations and prescribed sales techniques. But reps are notoriously independent thinkers -- and earning their trust isn’t quick or easy. Has this candidate thought about how she’ll win over her team?
While potential answers to this are infinite, here are several good ideas:
- Be the first one to arrive and the last one to leave: Reps admire hard work.
- Act as their internal advocate: They need to know you’ll look out for them when pricing is too high, they’re not getting enough tech support, the comp plan needs adjusting, etc.
- Eliminate administrative tasks: Freeing up their time to sell will get you lots of points.
- Give them autonomy: Resisting the urge to micromanage or poach deals will help salespeople improve and ensure they don’t resent you.
- Keep feedback specific and actionable: Nothing is more frustrating (or less helpful) than vague, non-specific suggestions like, “Ask better questions.”
6) “What motivates you in your current role?”
Work changes dramatically when a salesperson becomes a manager. They’re no longer riding the constant high of closing deals or cashing in hefty commission checks. As a result, someone who’s primarily motivated by making money might struggle after the promotion. Most managers actually make less than their reps at the end of the day, which can be a disconcerting experience.
This question gauges how prepared and well-suited the candidate is for the shift. If they reply, “I love winning business,” or “I’m saving up for a house, so that keeps me raring to go every morning,” you may need to delve deeper into their motivations.
A convincing response touches on motivators that’ll be relevant to a manager’s life as well, such as:
“I love the opportunities to help customers,” which would translate into chances to help their reps.
“I’m motivated by the fear I’ll let down my teammates,” which would translate into a desire to lead the team and contribute to the business.
“I’m highly competitive,” which would translate into beating the team’s previous record or outselling another team.
7) “What’s a big risk you’ve taken?”
Once they’ve answered, follow up with, “Did you take any steps to reduce that risk?”
As a leader, this person will have to take plenty of risks. And unlike when they were a rep, they’ll have the fate of many people riding on the results. You need to assess whether they’re A), comfortable with risk, and B) wise enough to prepare.
Take a look at this sample answer:
“When I was 26, I decided to leave my job and start a company with my college roommate. We were selling a new type of phone charger that was three times quicker. While the tech was great, we just couldn’t get costs down low enough to make each unit economical. Fortunately, I’d saved a lot of money so I could try to make this company work. It wasn’t an issue to close shop and find a new job. Plus, I discovered I was great at selling -- which led me into sales.”
Finding a great leader among salespeople isn’t guaranteed. The necessary skills and personality traits are extremely different. To find the best fit, use these seven questions.