Tips for Interviewing Sales Candidates and Scaling Your Organization

Scaling the sales team is one of the most exciting parts of working at a startup, but if done incorrectly it can be truly counterproductive for your organization. Scaling a sales team at Bizzabo has taught me a lot about how to scale the right way.

Here are my top tips for interviewing and scaling successfully:

1. Use silence strategically during the interview process.

Interviewing can really bring out the buzzwords in people, but that doesn’t really tell you very much about the person you’re interviewing. To get beyond this tendency, I have a somewhat idiosyncratic method for interviewing. There are some things you can’t really learn about a candidate unless you’re able to get them off their interview game and stop delivering rehearsed bits. I love silence as way to do this.

Silence makes people uncomfortable, so as an interviewer you really get to see how well the candidate handles that discomfort. So I’m typically a little more silent in an interview than I am in other situations.

For sales positions, I want people who can effectively end the silence and lead the conversation. Someone who can do that can handle the challenges of selling.

2. Gauge how well candidates deal with being put off-guard.

At the end of the interview, I’ll really take candidates off guard by asking rapid-fire questions that they probably haven’t prepared for. They’re really weird, random questions. For example, I’ll quickly ask about favorite movies, books, and sitcoms. I’ll ask, “if you had to erase one state off the U.S. map, which would it be and why?”

My assessment of their response has nothing to do with their actual answers. What I care about is how well they handle the unpredictable situation. I look for someone who takes ownership of the weird questions and is able to go with the flow. I figure that if they’re adaptable, they’ll be able to work effectively on a team.

3. Don’t overlook the importance of humility.

There’s so much to be said for humility in sales, and I think a lot of people overlook it. Even if you’ve had success as a salesperson for ten years, when you start at a new company you still have to learn things over again.

By nature, sales people are confident—whether that confidence is real or faked. We know how to carry our Type A-ness and be assertive, but the lack of humility can be a real problem. I look to hire people who can be quiet and just soak up new information.

Some great interview questions that reveal humility and empathy:

  • Tell me about someone you admire and why you admire them.
  • What’s one thing you’ve accomplished that you’re really proud of and why?
  • If you ran your own company, what kinds of people would you hire and why?
  • What skill do you need to improve on?

These kinds of questions can help you to gauge candidates’ values and willingness to learn.

As you interview candidates to grow your team, here are my top two learnings from scaling sales orgs:

4. Avoid scaling too fast.

Scaling too fast is a problem. I caution companies against trying to scale too quickly. As a general rule, if your last three hires aren’t independent, you’re not ready to be making new hires. You should always be interviewing potential candidates, but don’t pull the trigger on a hire until your company is ready.

The onboarding cycle is a helpful gauge. If you still have quite a few people who are being onboarded, hold off on new hires until they complete the onboarding process.

5. Understand the KPIs behind scaling and work with people who have already done it.

KPIs are critical to the scaling process. By working backwards from your data on revenue and conversion opportunities, you can draw a rough game plan for what the scaling process should look like. However, keep in mind that the processes that worked for you before may not be fully scalable. Be realistic about what’s possible.

I recommend working closely with other teams within the organizations who have already scaled. By doing this, they can fix your errors before you fully commit to them.

Scaling is an art as well as a science. By drawing on both KPIs and input from other teams, you can ensure a smooth scaling process.

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Becky Kuperhand is a Managing Partner at Apex Assembly where they unite F2000 decision makers to solve critical business challenges at IT and IT Security executive forums. During her 9 years as a sales and partnership leader, she was known for finding and developing talent, creating and implementing business processes, and always pushing her limits to improve herself, her team and her relationships. With a background in advertising and publishing, startups and software sales along with executive events, Becky has diversified her network and her knowledge. “Always deliver more than expected!