The Things We Should Know: Three Questions to Ask About Your Potential Boss

You’ll invariably have more than one interview in your life, unless you’re self-employed.  The days of getting your dream job on the first try or never being required to make a change are rare, so why not be prepared with the right questions.

While I promised some readers that as a former head hunter, career counselor and expert interviewer, I would put together a solid list of questions you should ask during an interview, I’ve had a few encounters that made me jump ahead and address this one:  “Who Will I Report To?, What’s His Professional Background? Who Does/Will He Report To?


Who Will I Report To?   It seems simple enough: You’re a salesperson, you’ll be working for a sales manager, right?  Not so fast.  Depending on the perspective or size of the company, this isn’t a home run.  Sales could be perceived as an arm of the Financial division or even more likely, Operations.   Truth be told, while everyone thinks that “they could be a salesperson”, not everyone could; and therefore, not everyone should be managing them.  Identify the traits that you want in a sales manager and be sure to ask the questions that help you understand whether you will learn from and grow under the direction of the person that will be your boss.

  • Has he ever been in a role where his pay was a direct correlation to his activity?  Is that the case now (does he make more if you make more?)
  • Has he been a quota based or “hard metric” managed individual during his career?
  • What traits did he have as a salesperson that he brought into his leadership role?
  • What’s his management style?  Coach?  Driver?
  • Has he managed a diverse team:  producers and non-producers?  Rookie and Experienced?  Are his techniques different for managing them?  If so, how?

What’s his Professional Background?  I alluded to this earlier but I’ve had the interesting experience of working at companies where: a Director of Operations had significant impact on the corporate perspective of the sales team, a Chief Financial Officer was the final authority in the sales process or a former corporate Trainer was the Sales Manager.  Which was worse?  You’re welcome to take your pick on this one, but I’ll go with the CFO.

The role of the CFO in an organization is defined with the same verbiage in most reputable financial or business dictionaries, all include, ‘responsibility for how a company manages its income and expenditures’.  Further, most CFO’s have risen through the ranks by exhibiting (at some point in their career), an ability to save money.  When I was a head hunter one of the best lines that you could use when presenting a resume of a Financial or Accounting candidate was, “he saved his company X dollars over X period of time by doing XXO“…yep, every company loves a phenomenal penny pincher in that role.  No one expected visionary CFO’s unless the vision demonstrated led to tightening the belt and leaving more coins in the coffers.  I don’t blame anyone that hires a CFO in that manner, kudos to them, everyone knows that the CEO is the visionary for the most part and the CFO will have an impact or perspective of whether the vision will move forward….BASED ON DOLLARS AND CENTS!

So, back to the original question.  Do you want the guy who was an awesome Accountant, phenomenal Controller, or Financial Analyst determining how you should and could make your money?  Only if he’s your direct financial advisor.  If you’re a salesperson you want to know how spending money makes an impact on the direct assessment of the job of the sales leader.  Sure, the sales manager should invest any budget dollars or resources wisely but a wise spend to a TRUE sales manager is different from what’s wise to a CFO–and closed-door discussions between the two can be rough because of these differences in opinion.

Additionally, the school of thought for a Chief Sales Officer is developed in a different environment than that of a CFO or Operations guy.  The way that they think about money is just the baseline measurement of their differences.  Temperament, personality and perspective are usually at opposite ends of the spectrum as well.  Have you ever seen an Accounting Manager jump out of his cube and have a “happy dance, pat myself on the back” publicity moment?  I’m sure you’re thinking hard or trying to make someone fit but you wouldn’t have to think hard to identify a Sales Manager that has run the aisles high fiving his troops!

The typical sales leader loves a rock star and doesn’t have a problem accommodating a high roller on the team.  I had a great Sales Manager that occasionally sprung for Starbucks as a show of appreciation (I loved that guy) while many CFO’s think that perks and incentives are feeding diva mentalities and your paycheck is your perk.  Remember that gift card would be the equivalent of $20 off the gross profit (yes, I’m wagging my finger here).  The CFO will apply the same spending mentality to how he structures your sales plan–that post is coming!

Ever been a “shushed” salesperson?  Walk through an Accounting Department using  your normal tone of voice and you may be!  Salespeople are notoriously social and talkative, you want a Sales Manager that will know the difference between wasting time and normal sales chatter.

Those are some of the basic reasons that you should be comfortable asking:

  • How did you get into sales?
  • What was the best sales job you ever had? (people often formulate their leadership style from early experience/exposure)
  • What were the steps of progression in your career?  (Does his experience allow him to identify salespeople that are ready for the next step?)
  • Tell me about one of the best salespeople you ever hired.  (Don’t you want to know what traits he likes in a salesperson and if you fit, outside of the usual buzz words?)
  • Is sales culture a myth or reality?  How do you define it? Who’s responsible for it?

Who Does/Will He Report To?:  To prevent repetition and insulting smart readers, I’ll just “say” this.  A great Sales Manager can be limited by his leader just like a great salesperson could.  When you have a phenomenal idea, have the occasional need to discuss your contract/comp plan, or want to discuss the plan of progression for your career, you want your direct supervisor to feel like it’s a worthy discussion.  If he’s working for a cost conscious CFO or process oriented Operations guy those discussions will require him “fighting on your behalf”, which ultimately will determine how long he is able to survive in that environment.  High turnover of Sales Managers that are salespeople at heart can often be linked to who they are managed by.  My experience:   A CFO’s impact on a sales team can be consistent changes in sales leadership as he searches for the person who will always say “yes” regardless of the impact on the emotional tenor of the sales team, i.e., changes in comp plan mid-stream, etc.

Ultimately, everyone  has a position to play.  I worked in an environment with a Harvard educated CFO, one of the best and I appreciated his worth, conversely, it was obvious that he appreciated the value of the productive Sales Unit and Leadership.  He was so confident in his role that he had very little interest in delving into murky sales waters although I’m quite sure he knew how every dollar was spent!

Bottom line, before you ever accept an offer be sure that you’ve taken the time to follow the salesperson’s rule on any deal:  QUALIFY, QUALIFY, And QUALIFY!

(If you enjoy this post, the “like” button is waiting for a click!  Have a great day!)

16 thoughts on “The Things We Should Know: Three Questions to Ask About Your Potential Boss

  1. This is such a good list. It not only helps you evaluate the position, it puts the employer on notice that you are serious about your career and understand that your management chain is part of that.

    • Thanks Carol! This list can be amended for ANY role within a corporation. I’ve noticed lately that people are so desperate to be employed that they are more concerned about impressing the employer than becoming educated about the opportunity and person they will be working for. If you don’t ask questions like this you could be without a job after the 90 day eval so why not do it up front and save yourself the headache?

    • I agree wholeheartedly, I actually said something similiar in response to Mary or Susan before I read this. Great minds think alike!

      Employers often complain that they can’t tell if the candidate was interested, etc. these questions will remove all doubt. Thanks for reading!

  2. If I ever decide to teach again, I will approach my interview so differently from when I was a newbie. Especially after sitting in on a couple of interview committees, my eyes have really been opened regarding what to ask and what not to ask during an interview.

  3. Boy howdy! When we are interviewing for a position, we forget that the fit needs to go both ways. So turning the tables and taking a deeper look at who is hiring (new boss or a company) can be a great way to determine if this the place for you.

    • Hey Susan! I agree. After you’ve been bit a few times or even hard enough once, you realize that these questions are in the best interest of the perspective employee and employer.

  4. I really like this idea of flipping the questions towards the boss and treating the interview as a two way interview to figure out if that boss is good enough for you. Of course you aren’t going to directly tell your boss this, but I agree it is important to evaluate what is a good boss for you and who you shouldn’t work under.

    • Thanks Mary! A great boss in any environment would appreciate the questions so that it is conversational rather than an interrogation. There are always creative ways to rephrase and work these questions into the “conversation”. A complaint that employers make frequently after interviews is that “they didn’t ask questions”, this will make you seem more interested in the position and responsible in your decision making as well as give you the info you need (assuming it’s an honest exchange).

  5. Every interview should absolutely be a two way interview. You should be interviewing your potential employer as much as he/she is interviewing you! Well said…

    • Thanks for the comment Angie! From a third party standpoint, I would wager that it would improve the investment of time for Executive Recruiters, etc. if the candidate asked these questions, the feedback would be invaluable to you both.

  6. As always a great and thoughtful blog. I think that employers expect a candidate to come with questions. Those questions often reveal more about you than the answers you provide in an interview. They also show that you’re engaged and have done your homework. Your comments about being in the right setting really hit home for me. I’m in the business of developing organizational relationships, I’m pretty gregarious and you can hear me laugh from across the street. Put me in a setting that values silence, and it might work for a week, but eventually everyone would be laughing with me or I wouldn’t be there. It’s not about not working, its about working happy. Knowing the culture in advance means you avoid discomfort for you, your colleagues and your employer.

    • Thanks Debra. I was working on a piece about culture and when I think about my career history I noticed that it has a common link in any situation that I’ve left and when I think of colleagues historically, I’ve seen many fail due to culture issues!

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