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!)

Let’s Dissect This: Smiling, Happy People Pt. 1

  Ever been involved in a meeting that makes you want to get up and leave the room?  I got that feeling when I heard these words:

‘Never hire people who left a company because they were unhappy, they will just be unhappy working for you.  It may be eight or nine months down the road, but they will be unhappy’.

Really?  Never?  I’ve heard the statement that “no opinion is wrong”?  Well, the person who first said that statement is probably the one who also determined that every player gets a trophy because “there are no losers”.  My belief?  Somebody has to lose (I just don’t want it to be me) and there aren’t just wrong opinions, there are stupid opinions.  The opinion above is a generalization about something that is way too complex to be generalized.  It’s hard for me to sit still in the face of individuals who make these kinds of remarks and believe them!  I guess I should give credit to anyone that is so confident in their understanding of the world but I have a hard time quietly dealing with narrow perspectives, so let’s dissect it a little…shall we?

Qualifier: Unhappy people exist.  Employees are people.  Therefore there will be employees that are just unhappy people.  Most people aren’t unhappy by nature.  Call me an optimist but unhappy people are so easy to point out because they are the exception not the rule.  I say this because it explains my belief that if you work with unhappy people or morale is low there is usually a reason for this.  And no, the reason isn’t that they are just all Debbie Downer’s.  Going back to the qualifier, I’m sure that there are a few Sad Sally’s (I promise no more alliteration) but that would be minimal. Okay, now that we got that out of the way, let’s move on.

I have objections to the idea that when someone is unhappy at Y Company and chooses to leave they will be unhappy with Z Company and eventually do the same.   Unfortunately, there are many corporate leaders and managers that have this frame of mind, especially during an employer’s market (when there are more people in the job market than available jobs).  A wealth of thoughts, some in the form of questions and others retorts, came to mind, none of which would be perceived as positive by someone living that reality so I’ll share them here:

Thought:  A “leader” who believes this statement can’t possibly have the ability to see the full needs of their employees.  When you decide that people are unhappy without good reason you’ve thrown away valuable opportunities.  The behaviors that encourage a dissatisfied employee to come to the table with their concerns or issues are the same ones that motivate a satisfied employee to share their successes.  Both are teachable moments.  A manager that conditions himself to believe that grumbles of disapproval are the sounds of the generally unappreciative, is making a foolish error.  When someone decides that people are whiners and would be whiners anywhere he is choosing, consciously or otherwise, to ignore the needs of his people–that’s dismissive.  It’s impossible to have anything other than a shallow relationship with a dismissive individual.  If I don’t trust that you have my best interest at heart, how can I trust your opinion on my career value to your company?

Thought:  Aren’t generals responsible for the morale of their troops?  You can substitute coaches/players in to this analogy and it all boils down to the same thing, the leader has great impact on the emotions, behaviors and perspective of those who must follow.  Not a great leader, but any leader.  Every General portrays an external belief that the war can be won, how else can you get the troops to pick up their guns and march?  He leads by example because he understands the sway that he has over his soldiers.  Additionally, when the battle is won he is lauded for his bravery and leadership, shouldn’t he be held accountable if the war is lost?  Bottom line, if your people are unhappy you bear some of the responsibility.

Thought:  This is a level of denial that could destroy or hinder a company.  Acceptance is the first action step in taking responsibility, denial has no place in that process.  Acknowledging and accepting issues at hand allows you to address and resolve.  That’s right….Acknowledge, Accept, Address and Resolve.

What do you get from denial?  Repetition of detrimental behaviors.  If being on time is important for a project oriented workplace, the employee that’s consistently late has to be addressed or the behavior will continue and the work will be impacted, right?  So, why not openly discuss employee concerns that are hindering internal success.   When someone feels undervalued or overlooked the best option is to speak about it.

Thought:  Holy Generation Gap, Batman!  Woe to the man who seeks the resume with one job!  You’ll be searching a long time.  The days of the gold watch and retirement are gone–employees know that, some employers want to ignore it.   Today’s corporate structures, financial economies and behaviors don’t provide as much access to the 25 year pin that many would welcome.  Sure, there are people who are proverbial “job hoppers” but they aren’t included in the masses that are seeking the best opportunity for their success and a place to call home.  Staying and working through the pain, year after year without a commitment to change is no longer the way of the world.  I believe that great employees have a sense of expectation based on their work and poor employees have a sense of entitlement.  Identify the two and take care of your people.

Thought: Says the Rich Man to the Poor Man.  No need to bring out the socialist banner and slap it on me, I’m just acknowledging that it’s very easy for the rich man to call the poor man ungrateful when he has full control of his destiny.  Employees that choose to look are often doing it because the environment isn’t theirs to change and they are aware that they can do better.  How ironic that we hold people accountable for their lack of wealth and positions in the world but call them unappreciative when they attempt to change it by seeking new opportunity!

The interesting thing is that I have heard this mindset expressed in other ways throughout my professional career in other ways, from people who have believed themselves to be visionary managers.  Statements like: “If you’re not happy, there’s the door”,  “This trains leaving the station and if you’re not on it, oh well”…lots of quipped, little expressions of power from small minded perspectives.  If you have said something like this or think this way, today would be a good day to reevaluate your standard of leadership.  Is it possible for those words to come from a good place?  Are they actually motivating? If this is your modus operandi, should you be managing?


Mad Journey #2: Understanding that People Leave People Not Companies (Pt. 2)

(Most people read Pt. 1 before they read Pt. 2 but just in case you didn’t:  I left a solid position as the number one Sales Exec at a company.   After doing so, I took time to review the impact that my manager had on my decision).


Marshall–the CSO–wasn’t a fan of salespeople and where they were concerned he lacked vision.  Long term perspective would have allowed him to nurture his team, treating them as commodities to be nurtured and developed over time.  For him, support team members weren’t individuals with great potential for contribution so he couldn’t acknowledge any idea that wasn’t his own as one that could be successful.  If this isn’t enough for you to get that people leave people not companies, read on.  You understand?  Read on, anyway.  Humor me.

I left him because he was like living with a drunken parent.  I know, it sounds harsh, but imagine coming home from school and not being sure of just what will set mommy or daddy off (ironically he referred to himself as a “step dad”).  I left him because he called others liars while lying himself.  Not lying just through direct verbiage but through manipulation and this for me is professionally unacceptable.

I left him because he couldn’t give anyone credit for being knowledgeable in their role except in a backhanded manner.  When I accomplished a major sales goal, he pointedly ignored any celebration of it.  Why?  I have a few thoughts about that.  Marshall would never congratulate someone on something that he perceived as their responsibility but placed very little value in.  The value was the dollars that I drove, not me, and showing any appreciation would be recognizing an individual and perhaps inflating her confidence unnecessarily.  Little did he know that confidence is like a sales warrior’s genetic marker and attempts to damage it are futile (this is where my partner would have inserted an evil laugh).

I left him because he consistently ran off mentors, successful people in sales management that could lift production and career value of my colleagues and me, because he wasn’t comfortable being challenged and his selfish nature led him to believe that they didn’t bring HIM value.  He once referred to a prove industry leader as being lazy as a way to dismiss the fact that he didn’t like this gentleman and knew that his C-level pedigree was greater than his own.

I left him because he assumed that being smart in SOME areas made him above challenge in ANY areas.

I left him because he considered salespeople as plug-n-play options, necessary but expendable.  An example was that when his #1 producer put in her notice (yes, me) he reassigned my territory without acknowledging my resignation.  A “we don’t really need you” gesture that made me laugh and one that he tried to refute when he asked me to stay two days later.

I didn’t want to be begged, it wasn’t my intention, and truthfully I have a rule about counteroffers, and accepting one from someone I don’t trust would definitely go against that rule.  However, a true sales leader or visionary would not let their ego get ahead of the success of the company.  Salespeople with documented success are hard to come by, you don’t let them walk without discussing the whys or being open to seeing your part in it.

I left him because insecurity is not a trait that I value.  My best mentors have all been men, including my current leader.  I’ve gravitated to the amount of leverage that men are able to drive in companies without appearing overly emotional, since many of us women get a bad wrap and unfortunately I haven’t had great success with female bosses.  I say that because my male mentors were all very confident.  Their belief in their own backgrounds allowed them to push me to grow and focus on my career without feeling as though it would diminish their ability.

Marshall’s insecurity was consistently exhibited.  Whether it was bad mouthing previous/current employees and leaders or confronting me for having a recorded conversation in which he felt a colleague and I were “talking about him”.  That day felt like a high school lunch room conversation with the petulant teachers pet and stuck out in my mind as behavior unbecoming a true leader.  It was additional confirmation that I needed to seek another environment.

I left Marshall because his ambition was eclipsing his aptitude.  Sure, he was smart but he wasn’t smart enough to realize that you can’t do everything yourself and that surrounding yourself with people who are afraid to challenge you doesn’t mean you are creating a collaborative environment.  Rigid ambition motivated purely by the need for power is damaging to everyone and everything it touches.

The above paragraphs all include “I left him” because at the end of the day my clients, success, and paycheck were not enough to trump the fact that working for Marshall was teaching me more negative than positive.  I COULD work for him but I WOULDN’T.  I would not give him the satisfaction of claiming my success as a result of his leadership.  I had no interest in confirming his management style as relevant to someone with my level of talent and self-directed abilities.   Additionally, I didn’t respect his lack of first hand sales knowledge and unwillingness to admit it.

For those who may think so, I’m not sour grapes over the situation.  My feet landed on solid ground and I walked away on my terms but, more than that, I’m grateful to Marshall.  He confirmed that my career and personal growth should be my greatest priority (as was his) and that WHO I work for/with is just as important as where I work and what I’m doing.  I made a mature decision and in doing so proved that while money is important it isn’t my sole motivation and that the risk I was willing to take would be the type of thing that will make me a great entrepreneur in the future.

Without changing the title of this piece, I’ll admit that I could be wrong in throwing out the old cliché.  Maybe people do leave companies but only because of the environment created by the people who lead them.

The Mad Journey #1: I Now Understand that People Leave People Not Companies (Pt.1)

I quit

Resigning isn’t an easy thing to do when you like your job.  While salespeople are often though of as easily bought for a dollar, it’s not true.  When you’ve built a strong book of business that recurs, have contacts and relationships in your industry and know that you have reliable commission coming your way because you’ve done the heavy lifting, walking away to something less “sure” is a tough thing to do.  Trust me, I did it!

I walked away from being the top dog.  You don’t go into sales without wanting to be number one or you can’t last, so giving it up when you get there is uncomfortable.  I left, certain only that I was going to have to develop a new book of business in a nearly 100% cold prospecting environment and work without the benefit of immediate commission on a longer sales cycle.  I had a Tina Turner moment, you can keep the money and the territory but I’m walking away with my name!  Crazy? Only if you don’t believe in yourself.

Before leaving I spent time reviewing the why’s, how’s and where’s of it all.  Sales is my career, it’s not a job so I had to be smart.  I reached out to experienced mentors whose opinions I trusted and I weighed their advice.  My long-term plan is to move into the realm of sales consultation and run a major firm but being fully self-employed at this time in my life doesn’t make sense so change had to be good for my current lifestyle and support my future mission.

Needless to say, I did what I needed to do and walked away knowing that I wasn’t running from something but to opportunity.  At least that’s how I kept it initially.  Notice that above I didn’t mention the word “who” in any of my review on why I was leaving.  At the time, it was relevant, not powerful, so I kept it out of my decision making  process.  Today, it’s relevant AND powerful.

Who you leave behind at a job is significant, yet often ignored.  I left a role that I was passionate about because I didn’t trust management with my career.  It had been clearly and repeatedly demonstrated to me that development, encouragement, stimulus and growth were at the bottom of the list of priorities for the people who wanted to be attached to my success.  What I could do for them was paramount.  This could be said for any company in a capitalistic society.  I’m sure some of you are reading and saying, “What’s she complaining about if she was getting paid?”  That could be seen as a reasonable response, if you weren’t speaking to a responsible career woman.   Let’s assume for the sake of this piece that you are.

Every day corporate executives renegotiate their salaries or leave companies to pursue the opportunities that allow them to expand their knowledge base and further their careers as well as make more money while salespeople or support team employees that do the same are thought of as money hungry, disloyal and sometimes irresponsible.

I view myself as the CEO of my career.  My office space within the company is my “practice” and my role is a “contractor”, even if I am   The terminology keeps me on task and helps me to treat my job like a small business so that I focus on driving my success and avoid the pitfalls of being an employee.  I worked for someone who underestimated the importance of this behavior and disregarded the value that I place on my responsibility within a company as mere egotism.

This particular manager, we’ll call him Marshall, had a poor perspective of salespeople.  His best idea was that we all should be non-commissioned, clock punchers and treated like telemarketers (while he purported to understand sales).  Overpaid divas with over inflated expectations, that’s what we were.  To the company’s credit they understood that you couldn’t remove commission structure from current salespeople but I’m sure that any hiring in the future by this “manager” would be under a bonus structure rather than a commission plan.  By nature Marshall was a tactical number cruncher yearning to be a strategic visionary so, of course, true creatives—a  natural trait of successful salespeople–were in his mind “Un’s”….unstructured, unruly and unproductive unless they kept their heads down all day and functioned like robo-dialers.

Long story short, I left him.  Spending months observing Marshall and his behaviors were enough to confirm that people do leave people. I broke this post into two parts to give you time to grab a drink, Marshall’s an interesting character, you’ll need one.

Internal Rapport…Yeah, It’s Necessary

Dear Fearless Leader:
I appreciate the impression that you want to give during your first week on the job, I really do! As a salesperson I’m well aware of the need for your boss to be impressed by your ability to produce, so I want to be respectful of your desire to ‘hit the ground running’. It’s great, actually, that you are demonstrating what is required of most wide-eyed new hires….interest, desire to achieve objectives, the usual; but, and I really hate to follow-up with a “but”, so I’ll begin with a “however”; However, there are some pieces of key advice that could be helpful that your new bosses may not be aware of:
1) Before heading into battle it’s important to assess the situation–for yourself. Of course there will be those who have been in the battle longer than you that will give you their perception of the war and how it has played out, but a good 30 day “quiet period” to review the situation independently, won’t hurt. Sure, you have an initial understanding of what corporate wants but rather than lose yourself in this, don’t forget to determine what’s important to you and what available tools you have to play to your strengths–a necessity for you to conquer corporate goals and provide true achievement.

A good place to start: How many troops are in your platoon? Who is the enemy? What’s the objective of the battle? Was the last platoon leader/commandant killed in the field of battle due to lack of preparation or was he/she improperly armed? Where do your previous successes offer immediate opportunities to be relevant to your troops?

2) After you have assessed what the mission is, it’s important to identify which of your troops are actual Platoon leaders worthy of higher rank (sergeants, etc) and which are going to remain your rank and file foot-soldiers. Once you have identified this, it will be in your best interest to create trustworthy relationships with your leaders and make them your right hand “men”, which will in turn give you assistance as you reach into your lower ranking soldiers and prepare them for the baseline of hand to hand combat. This will ultimately, help you win the easy battles and move your platoon toward “capturing the flag”.
3) Remember that the Commander-In-Chief and all of those that report directly to him in the war room have a goal: WIN THE BATTLE! I am sure that they will provide directives and occasionally respect you enough to offer suggestion; but at the end of the day they want you to give them the nod of “Mission Accomplished”. This central focus provides you with plenty of “forgiveness vs. permission” opportunities. As long as you are moving closer to the battle objective, you can actually make decisions and assessments on your own. If you have done well enough with objective 2 (See above), there won’t be a lot of obvious errors because your field troops and sergeants will keep you aware of which paths have been previously tread and what landmines to avoid!