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7 Easy Ways to Tell a Good Sales Boss From a Bad One

At a sales rally at my first job, after a handful of PowerPoints and Kool-Aid drinking exercises, I bumped elbows with the VP of Sales during a 10-minute break. He looked me in the eye, put his hand on my shoulder, and said “Benjamin, you’re going to do great things here.”

My name is Dan, and I left that job two weeks later.

This man had the conviction of Christopher Walken and the speech skills of a president—he was a pro sales guy. But he was not a pro sales boss. He never learned two important things a sales leader should know about his team member: what I’m motivated by and my name.

A bad boss can stifle your productivity and deter you from pursuing your ambitions. But a great boss can gift you with every opportunity their network will offer and help you chisel your skill set. (And, in startup culture, bosses are often brilliantly talented, yet just a little inexperienced with management.)

So how do you tell if someone will be a great sales boss or not the right one for you? Try these strategies you can use pre- and post- job interview to determine if that person is the right one to manage you.

Before the interview:

  1. Know yourself. Ask yourself these questions: What am I looking for out of this job? (Maybe you want to find a mentor, or earn a management position.) How do I respond to criticism? Do I like to be challenged with positive or negative feedback? Am I competitive? Do I like to build personal relationships with my colleagues? What would I tell this boss about me if he asked me how I like to be coached?
  2. Look in your past. Think back on the authority figures in your life. What are some of the personality traits you respected? What did these people say or do that stuck out to you? Now flip it: what don’t you like about the way you’ve been coached before? Keep these things in mind as you head into your interview.
  3. Stalk your potential boss. Look online for small social hints that could give you insight into who he or she is. Do you notice any trends in his LinkedIn network? If he has a relatively insular network, he might not have as much self-awareness as a sales boss yet and could require some upward management. How does he carry himself on Twitter? If his feed references some of his personal interests and photos, he might be more laid back.
  4. Plan your interview questions carefully, especially when it comes to:
    1. Culture: When are team meetings? When does the team hang out? Are folks on the team friends outside of work? What are the hourly expectations?
    2. Process: Understanding the way they articulate process, and their reactions to these questions, could indicate how experienced they are in sales management or operations and how mature the sales culture is at this company.

Related: Don’t Make These 10 Mistakes In Your Sales Job Interview

After the interview:

  1. Ask follow-up process questions. Who makes the sales collateral? How much cold calling will you do? Pose questions like these to your potential boss and see how quickly he or she responds. The answers and the way they’re delivered can give you an idea of how questions will be handled on the job.
  2. Apply your past to your future. Revisit the answers to the questions you asked yourself about your past leaders. Did you notice any similarities between prior leadership figures in your life—good and bad—and your potential boss?
  3. And if you get an offer, is he or she using any pressure techniques to try to get you to accept?

At the end of the day, it’s safe to trust your gut when assessing your future boss. Use these tips, then ask yourself: knowing what I know now, can I see myself working for this person?

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Dan Gottlieb

Dan Gottlieb is Sales Development practice Analyst at TOPO Inc. He is just a guy living in a mobile world. When he’s not working or feeling all cool, he can be found playing bball, out by the school.