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Sales - 6 min READ

Hiring a Sales Manager? Here's What to Ask in an Interview

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Author photo: Kent Holland

Kent Holland

Vice President of Sales at Copper

Hiring a new sales manager is no small feat. The future of your sales team is at stake—literally. After all, this person won’t only be leading your current team of sales reps, but finding and overseeing all future hires as well. No pressure, right?

Here’s a tip: before you even start looking at sales manager candidates, make sure you have defined goals for the future of your sales team. Then use this vision as the benchmark you use to compare all your candidates.

For example, as the Senior Director of Sales at Copper, my goal is to build a sales program that empowers sales reps to develop into top-notch professionals. I want the sellers on my team to advance from sales development reps (SDRs) into closing roles, and to continually advance into more strategic and complex roles that drive the business even higher.

"Basically, my goals for the sales team revolve around growth and longevity. The sales manager I hire needs to be on the same page."
Kent Holland, Senior Director of Sales at Copper

Given the above, I need sales managers who are excited about the company and eager to build something special. I want them to be focused on building a team for the long-haul, not optimizing solely for short-term wins at the expense of team culture and camaraderie.

To find out if candidates align with my vision for the future of our team, here are six questions I always when I’m interviewing for a sales manager.

(Note: I like to delve into one or two related questions based on an interviewee’s answers to each of these before moving on to the next big topic/question—but these are my go-tos.)

1. “As a sales leader, what is your recipe for success?”

I view culture and leadership different than how I view management; to me personally, the first two are the most important ingredients for a successful manager.

The truth is, a lot of people can be great managers. I want to get a sense of the intangibles in this answer.

What do they do to keep folks motivated and excited? (Throwing parties and celebrating wins are great, but if the candidate can give me other, less-obvious examples, they get bonus points.)

How do they build a consistent, positive culture? Culture has to come through in the “recipe for success.” Plus, the way they answer open-ended questions like this one gives me a good insight into the things that matter most to them.

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2. “How would someone who works for you today rate you, and why? How would others describe your leadership style?”

I want to understand how a potential sales manager think on their feet, what their presence is like, and whether they can be self-reflective on their performance.

I'm looking for a real answer to how someone who works for this person would rate them. In other words, I’m not looking for a “10” but an “8” with a good sense of which areas they need to improve on. (I'll also ask what they're doing to build those developmental areas into strengths.)

With the second part of this question, I’m looking to learn if they’ve managed and grown a team successfully in the past. I'm especially interested in how others perceive their leadership style—are they seen as motivators, mentors, or leaders? Or are they looked at merely as someone who gets the job done? Or, do they drive great numbers, but have a team that only stays in-seat for 6-9 months and wants out?

3. “What's your approach for sales reps who aren't hitting their number?”

Yes, hitting quota is very important for sales reps.

But what I’m really interested in here is learning about a candidate’s leadership style.

I look for managers who care about mentorship, coaching, and career growth of the folks on their team. Someone who has the company and their team’s best interests in mind, and makes decisions accordingly—even the tough ones.

4. “What do you look for when you're hiring sales reps?”

Like I mentioned in the intro, when I’m hiring a sales manager, I’m essentially hiring an entire team of SDRs because I’ll be entrusting our existing reps (and future reps) to this person—and with them, our sales numbers.

So, it’s essential that a candidate’s hiring criteria align with what we look for in a sales rep (and to confirm they actually have an idea of how they would hire sales reps, which is kind of important).

5. “How do you pick and choose where to spend your time?”

There’s a reason why I ask open-ended questions over more generic sales interview questions, and that's because it gives the interviewee space to talk about their perspective and approach without me guiding them in any specific direction.

So for this question, for example, rather than ask them “what metrics are important to you,” I would instead pay attention to the way they answer the more general question: how do you spend your time?

From their answer, I can pick up on whether they’re analytical by how (or if) they talk about metrics as something they look at when they think about how they spend their time.

If they do start talking about metrics, I’d then push on which ones they measure and report on to the business.

Similarly, if they talk about spending X amount of time with reps who aren't hitting their number, I might ask how they weigh the time spent improving under-performers vs. time spent with over-performers, or ask how they deal with sales reps whose ego is bigger than their skill-set.

6. “Your team missed their number last month/quarter—now what?”

I try to understand the way the candidate responds to different challenging situations—like missing the number.

What are the steps they take to diagnose the challenges, and how do they handle it?

My aim here to figure out what they prioritize and how they balance the human aspects of the role with the numbers-based outcomes that the business is looking for them to drive.

For example, if they’re blaming missed numbers entirely on the team rather than themselves, this would be a red flag for me indicating this manager won’t take accountability for their team’s performance.

But if their language is inclusive “we” or even first-person “I,” that gives off much more of a leader vibe to me. It shows me they understand they’re actively leading a team, not just supervising one.

Because generic questions get generic answers.

The approach of asking open-ended questions forces sales manager candidates to really think before they answer, which tends to get me more authentic responses than generic or closed-ended questions would.

I look for thoughtful answers that dive into different aspects of the role which I think are important:

  • Coaching
  • Mentorship
  • Metrics and measurement
  • Exec presence and big deal support
  • Organization
  • Ability to look at the business at different levels (e.g., get deep into a deal cycle, and then pull back and have strategic conversations with the sales leadership team about the direction of the business or gaps in processes)

Thoughtful answers are the best answers.

Don’t just hire a manager; hire a leader. 

With sales managers, I focus a lot on their leadership and coaching abilities. I'm looking for folks who can create (and are prescriptive in creating) an environment conducive to growth and success. In other words, look for a good sales manager who plays for the name on the front of the jersey, not the name on the back.

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