Great Boss: A Chance to Fail

This notion – that employees need an opportunity to fail – is undoubtedly counter-intuitive for many people.  Over time I have come to realize it was one of the key things that made my best boss great.

I’m not talking about the practice of casting someone out into deep water without a life-ring and hoping they’ll learn to swim.  Structured chances to fail were carefully managed by my boss to stretch and test me and generally excluded potential for career-ending failure.  As a result of meeting and (mostly) succeeding with these challenges, I advanced my management skills and insights much more rapidly under his tutelage than under any other boss.

And you know, it was actually enjoyable.

What most managers do

I’ve experienced managers on both ends of the spectrum – either they send you out to slay dragons, while both underequipped and overmatched, or they micromanage you every step along the way.  Getting the touch right with an employee that is ready to grow and develop can be tough.  But it can be done, no matter where the subordinate is along the developmental horizon – neophyte to journeyman, and everywhere between.

I can’t even label the “hands off “approach as “benign neglect” because there is often an element of devious politicking involved.  Hands-off managers tend to leave subordinates to their own devices, knowing full well that if things go wrong the subordinate can easily be blamed and, if necessary, subsequently discarded.  Some managers, in fact, are so adept at this that they line up a scapegoat for every challenging assignment or edgy project.  Even the most generous excuse for this behavior – that the manager is “too busy” to be involved to the degree needed to develop the subordinate – is hardly a sterling example of how to be an effective boss.

One of my bosses fell squarely into this category.  When things went wrong, he invariably shoved a scapegoat-subordinate into the breach, often one that was eventually fired for not turning the proverbial “sow’s ear” into a “silk purse.”  He called this “going up” when there was a problem as opposed to “diving down” into the details in an attempt to render assistance.  Eventually, it was my turn to be the hapless victim of this Machiavellian management method, although I freely admit I helped nominate myself for corporate martyrdom by making a series of high risk calls at what turned out to be the exact wrong time.

Most of the lessons I leaned from this boss involved how to effectively politic and blame others – hardly the stuff that helps a person develop into a great boss.

Deliverables is the prequel to Heir Apparent

Deliverables is the prequel to Heir Apparent

At the other extreme is the micromanager.  These bosses, for whatever reason, seem to find it impossible to give their subordinates leeway to make decisions or try pretty much anything of their own devising.  I suspect that the reason for this “style” of management has its roots in either a feeling of insecurity (a manager sure if she will make it in her job,) inadequacy (a manager that subconsciously isn’t sure that he deserves the success he’s already experienced,) or, at the other extreme, a supreme confidence that their way is always the right way.  Regardless of the motivation driving micromanagement behavior, the effect is pretty much the same – oppressive, suffocating oversight, and endless second guessing.

I had one boss that nominally fell into this category, although he was far from the worst micromanager I’ve ever seen.  Because I was pretty far along in my career at that time, I found his constant need to drive every aspect of every decision to be beyond annoying.  I eventually left that position, and at least part of the motivation for the move was feeling that “this town wasn’t big enough for the both of us.”

My Great Boss

Maybe I was at the perfect point in my career (near the midpoint,) but my best boss seemed to have an instinct about when to give me a chance to show my stuff, and just how far to let me go without a check-in and a check-up.  I saw him manage his more senior people with a slightly different approach, giving them more freedom to act, but still not just turning them loose when they ventured into unfamiliar territory.  I suspect that a newbie employee would have found him providing more (but still wholly appropriate) guidance.

Part of what made this work was his “touch.”  When we reviewed progress on my projects his method was Socratic -- he asked me leading questions that ultimately brought me to conclusions that were better than I would have arrived at on my own.  Key to this was that the “ah-ha’s” were mine to experience.  And I was free to argue and even reject his advice, which I did on occasion.  The point of this exercise was to make sure I owned both the decisions and the outcome while learning in the process.  My Great Boss wanted me fully aware of all the implications of the direction I was proposing, but ultimately to take full responsibility for it.

I loved this environment.

One project I headed, a small, bolt-on acquisition, taught me 90% of what I know about doing deals – knowledge I’ve put to use repeatedly in subsequent years.  I remember many meeting with my boss to discuss elements of the valuation, direction of the negotiation, and how to present the opportunity for the CEO’s approval.  But he never told me “do it like this.”  That was my responsibility to determine.

The acquisition ultimately went through and was integrated into the business unit with minimal issues.  I owed much of the success to my boss’s guidance, but I could still claim the victory as my own.

In the later years of my career I attempted to emulate his technique with my subordinates.  While I know I often failed to stay true to the lesson (I have a tendency to be a bit of a micromanager at times,) I thought that by and large I succeeded with most of my direct reports – hopefully to their long-term benefit.  And as a side benefit to me, I’ve had numerous experiences when the solution proposed by my subordinate was better than anything I would have dreamed up.


Subordinates develop more quickly with skin in the game, but there is no substitute for the knowledge of an experienced hand – the trick is bringing both to a job or project.  Getting the formula for this correct can be difficult, but when you are successful, you unlock hidden potential in your subordinates.  Give your people guidance, but also provide them with a chance to fail based on their own merits and abilities, and preferably in situations where failure doesn’t spell the end of their careers.

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

To the right is the cover for HEIR APPARENT.  Someone is killing corporate leaders in Kansas City.  But who?  The police and FBI pursue a "serial killer" theory, leaving Joel Smith and Evangelina Sikes to examine other motives.  As the pair zero in on the perpetrator, they put their own lives at risk.  There are multiple suspects and enough clues for the reader to identify the killer in this classic whodunnit set in a corporate crucible.

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