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!

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