Great Boss: Key Insights

Most of us would probably consider ourselves to be “perceptive.”  After all, we depend on our perceptiveness to protect us from danger, to give us insights into how to steer our behavior, and to tip us off when there are opportunities to exploit.  Here’s a tip – you’re probably not as good at it as you think.  Many people seem to misperceive the motives and emotions behind the actions of others a good portion of the time.

Perceptiveness is one of those qualities that is a small part inborn talent (you’re born with a certain amount of it) and a bigger part learned (you can improve your game with effort and experience.)  As it turns out, I was granted less of the talent portion of this critical skill than many of my business peers and as a result urgently needed to develop my abilities in this area.

The question was:  How?

When the student is ready, the teacher will appear

There is no course on “perceptiveness” in the MBA program at Harvard.  No training session on it at GM or Emerson Electric (or probably anywhere else, for that matter).  It is, like many managerial skills, largely an experiential capability – one developed primarily through practice and use.

By the time I started working for my best boss, it was clear that simply relying upon my own experience to improve my perceptiveness was probably not going to work.  Not that I hadn’t made progress, but I was stepping on a lot of toes while learning my lessons by making mistakes.  Some of this was funny and forgivable, like when I would automatically (incorrectly) assign boss/subordinate roles when meeting people for the first time.  Other times it could be horribly embarrassing, like the time I loudly asked a superior about the new baby at home, only to discover that the child had recently passed away.

It was clear I wasn’t reading people well enough to prevent occasional catastrophic errors – something which I needed to be able to do if I was to function as an effective leader somedeay.

That’s when I went to work for my best boss.  He became my teacher in the art and science of perceptiveness, and I was his student, gobbling up every insight and bit of advice he had to offer on the subject.  To my great benefit, not only was he completely free with his insights into this world, he was also very skilled.

What most managers do

One of the pictures that helped inspire the cover of EMPOWERED

One of the pictures that helped inspire the cover of EMPOWERED

Perceptiveness skills vary all over the map within management ranks, ranging from excellent down to stunningly bad.  For your manager to even have a hope of helping you, she needs to be better at it than you are.

Your boss can be quite skillful in this area, however, and still not help you.  Not all bosses are willing to share insights, and the process they used to arrive at them, with their subordinates.  In fact, I’ve found the willingness to share to be a relatively rare predisposition on the part of a boss, and I suspect the main reason for this is that there is a degree of risk involved.  After all, the subordinate might be loyal to someone else in the organization.  Or perhaps, he is a hopeless gossip, and anything sensitive the boss passes along will quickly become public knowledge.

Beyond both skills and a willingness to share, the boss has to actually have an interest in helping you improve your perceptiveness skills.  The intersection of high skill, low apparent risk, and a willingness to help already tells you that getting this kind of instruction from your boss is going to be rare.

Throughout my years in large corporations, I had only one other boss that attempted to “take me under his wing” and provide me with insights about how the formal and informal power chain worked within in the company.  Unfortunately, he was only slightly more capable in this area than I, lending new meaning to the phrase “…the blind leading the blind.”

Another inspirational photo.

Another inspirational photo.

Most managers simply don’t offer to share key insights.  If asked, they might give you a taste, but they will often hold back when it comes to particularly sensitive information – fearing its revelation may somehow hurt them.  Even if you gain insight into how they are able to recognize certain truths and trends, you always need to temper that victory by understanding the possibility that you might not be learning it from a particularly insightful source.

My greatest boss

With my best boss, the dynamic was completely different from what I experienced with every other boss.  He not only regularly offered his insights to me, he was also ready to explain how he’d gained them including detailing his sources, how he interpreted subtle words and actions, and who he might approach when needing to verify uncertain conclusions.

For my part, I was a sponge, soaking up everything he said on the subject of perceptiveness, and often asking probing questions.  Eventually, I began to bring my own uncertainties and questions to the table, and ask for his insight.  Under those circumstances, he rarely just gave me an answer, but instead insisted on leading me there by asking a series of probing questions.

One such discussion involved my next job.

I don’t recall who brought up the subject, but I suspect he did.  The conversation went something like this…

Another inspirational photo used for the cover design of EMPOWERED.

Another inspirational photo used for the cover design of EMPOWERED.

Best Boss:  Where do you see yourself in five years?

Me:  I don’t know, maybe as a division president.

BB:  That might be too long a time for that to happen.  Let’s say for now that I agree with your goal but might want to speed things up a bit.  Ideally, how would you get there?

Me:  I suppose I’d move into management at one of the smaller divisions in a job reporting to the division president – preferably one where I was already the heir apparent.

BB:  And then you’d what?  Just wait for something to happen?

Me:  I suppose I could try to pick a division where the president is likely to retire soon or be promoted.

BB:  Good thinking.  What role would you want to move into?

Me:  I don’t know.  I’m probably strongest in operations.

BB:  And strategy.

Me:  If you say so.

BB:  What part of your background needs the most strengthening?

Me:  Probably sales and marketing.

The conversation continued along in this vein until it became clear to me exactly what the ideal assignment looked like.  We talked about the corporate perception of my next promotion, the overall timing (what would be too quick – less than a year – and what would be too long – more than three years).  We even discussed how to make a noticeable impact in the short term, and how that might improve my chances of ultimately succeeding to the job.

Notice he asked leading questions, but most of the discussion was him listening to what I wanted and getting me to think about the best path to reach my goal.  Maybe there was some subtle manipulation, but if so, I certainly didn’t feel it.

Ultimately, I ended up as VP of Sales, Marketing and Strategic Planning at a small division, one that reported directly to my boss.  The current division President was over sixty years old and was likely to retire in the next one to three years.  Nothing was guaranteed, but by working with my best boss, I was able to position myself for the most important promotion of my life – my first job as a general manager.


Most bosses won’t offer you the benefit of their insights, much less instruct you on how they gained them in the first place.  My best boss did all of that, and more.  Doing so took a willingness to take a chance on a person he didn’t know well, recognizing that by putting himself at moderate risk he would either earn my loyalty or quickly discover I wasn’t worth the effort.  That’s what leaders do – they go beyond the mechanical elements of day-to-day management to inspire and motivate those that work around and with them.  My best boss truly qualified as a great leader.

Other posts in the Greatest Boss Series (in Chronological Order):

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Here is the cover for my latest novel, EMPOWERED, which was released in ebook and paperback versions on October 12, 2014.  EMPOWERED is the story of newly hired division president Colin Jensen, and his investigation into unexplained performance problems in the shipping department of TruePhase Chemicals division.  The story is set in Indianapolis during a blizzard, and takes its inspiration from the television series Undercover Boss.  As always, there are a few plot twists that I hope will surprise and entertain the reader.

My novels are based on extensions of 27 years of personal experience as a senior manager in public corporations.