Great Boss: Career Management

My apologies, for some reason I can't seem to enter more than one picture in this blog post -- technical site problems, I suppose.

Many supervisors claim they help their subordinates manage and develop their careers.  In most cases, this means that they examine educational background and experience, looking for “unchecked boxes” and then offer semi-generic advice about how those unchecked boxes are holding back the person.  Such advice is, in my personal experience, nearly useless at best and at times can be downright damaging.

A better boss helps you identify what is holding you back (I’ll talk about this a little later when I discuss “elevator speeches”) and offers practical ideas you can apply, not to mention providing frank recommendations on next steps when you are wasting your time.  A better boss will actually provide you observations you are unlikely to make on your own, and/or insights into how things work at the company of the type that would have taken you a long time to figure out on your own.

My best boss even went beyond this – having open discussions with me about where I wanted to go and how to position myself to get there, and THEN HE MADE IT HAPPEN.  My best boss was completely open and honest with me about where I stood in the pecking order, what was holding me back, and was willing to take some personal risks on my behalf to change the trajectory of my career.

The weak ones

“You need to finish your degree.”

“You need experience in product management”

“You need an MBA.”

“You need experience working in division X.”

This is the kind of “shoot from the hip” career advice you’ll get from a less-than-stellar boss.  It is typically offered with little contemplation of your current career position, and mainly covers what might be seen as “holes” in your resume.  Never mind the fact that getting that MBA or working in product management will often provide absolutely zero practical help in getting you to your next promotion on the way to your ultimate career goal.

Superficial advice of this type is all about “removing paper objections” things that a theoretical hiring manager can use to screen out an “undesirable” candidate.  The theory seems to go that if you eliminate all the objections, the hypothesized hiring manager will no longer have the ability to turn you down for the position.  It seems silly when you think about it, but I’ve seen employees waste enormous amounts of time and effort trying to satisfy such recommendations, only to find that there is always another barrier to overcome.

Part of this is because, as I’ve previously discussed, employees are often relatively clueless when it comes to their own performance (or lack, thereof) and the related management perceptions – for more on this subject, see: Classic: Behaviors Managers Hate, Performance Cluelessness.

I suspect that part of the employee’s problem is simply wishful thinking, which makes them susceptible to this “paint by numbers” approach to creating a career masterpiece.

On the boss’s side, stopping at this level of career advice is most likely a combination of laziness, limited perception, and a desire to avoid difficult conversations (usually about what is really holding back the employee).  I’ve seen all three factors in play in varying proportions during my career.

Possibly the most common action taken under this kind of “advice” is pursuing educational objectives (most often an MBA).  In most cases, when the boss offers this as her advice, I think it is just a way of “kicking the can down the road” and thus avoiding an uncomfortable confrontation with the employee.  Following such advice, employees make substantial personal (and often financial) sacrifices, only to be shocked when they discover – degree in hand – that management at the company views them exactly the same way they did before they got their sheepskin.

Not to say that an MBA is useless.  I personally decided to go to school full time to earn my MBA – at least in part because I was finding myself stuck in technical roles when my interests were running in the direction of impacting the overall business in a meaningful way.  Interestingly, I came to this conclusion on my own, rather than having it “presented” to me by a lazy boss.

Middle of the pack

Most people have something they do (or don’t do) that holds back the progression of their career.  I did.  You probably do, too.  Maybe there are several things.  The problem is, if you take superficial career advice from a weak boss, you’ll likely never figure out what you really need to work on to get ahead.

As human beings, we seem extraordinarily adept at self-deception.  We can quickly find the “fatal flaw” in a peer – the thing that is preventing him from being promoted – but we rarely see our own.  In fact, even when someone hints around at our biggest weaknesses, most of us find a way to rationalize away the feedback.  It seems that only through direct confrontation do we really get a glimpse at our biggest shortcomings.

This thought is what inspired a change in the way I wrote performance reviews for my people, converting a couple of pages of check boxes into what I called the “elevator review.”  An elevator review is easier for the boss to prepare, and much more impactful than the typical, hated annual review.

Here’s how it works:

I make a list of two, possibly three strengths the employee has, and balance that against one or two of their biggest shortcomings.  All of the items I identify are the kind of thing I would mention to my boss if he asked about the employee and I had 2-3 minutes to respond – especially, the most important items that limit or hold back the person.

Then the employee and I have a frank conversation about “the good, the bad, and the ugly” and how the future can be changed/improved.

The “elevator review” came about as a result of two things.  First was the realization that the traditional review forms never correctly portray the picture of the employee.  It is far too easy to mark lots of things as “above average” and then soft-pedal the one or two big problem areas.  Employees are usually left with the impression that their “pros” massively outweighed their “cons” and probably they then conclude they are one of their boss’s best performers.

The second reason was reflecting on the most meaningful review I ever received.  It was one I had been given years earlier – a traditional form review, but one that ended with a poignant summary.  I recall exactly what my boss wrote in that box:  “Gets a lot done, but sometimes pisses people off.”  That was my first “elevator review” and it had more impact on me than a career of check box forms.

Taking it up to “11”

My best boss went beyond the “elevator review” style of discussion – which we had numerous times, not just as an annual event – and actually took positive actions on my behalf to move my career along.  Together, we identified my target position, and then he created an interim position for me that would help me gain experience and credibility in a functional area I with which I was unfamiliar (sales).  He then sold his boss on the job move, and made sure I was properly taken care of financially.  I actually got a shot at the target position early, the result of hard work on my part and plenty of help from my boss.

When the target job opened up, he again advocated for me, allowing me to win the job despite being the youngest employee in company history to ever move into a division President’s job.

While I know he didn’t go this far for all his employees, everyone that directly reported to him (and was a loyal, committed, solid contributor) got at least a portion of my best boss’s valuable career management package.


It is one thing to offer low risk, off-the-cuff advice about career management to a subordinate, and quite another to take the time and potential political risk to dig deep and help the employee make their dreams a reality.  Weak supervisors rarely go to the effort of actually helping their employees.  Better bosses will be more insightful, but will often stop short of putting themselves at risk by aggressively advocating for a subordinate.  The best managers, however, will do almost anything to help a valued direct report advance and grow – that’s one of the key things that make them great bosses.

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

Posts in the “On the Way Out” Series (in Chronological Order):

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Shown here is the cover of NAVIGATING CORPORATE POLITICS my non-fiction primer on the nature of politics in large corporations, and the management of your career in such an environment.  This is my best-selling book.  Chocked full of practical advice, I've had many managers and executives say they wished they'd read it early in their career.

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