Great Boss: Acting Boldly

Some people are visionaries, while others are followers.  Some are risk takers while others are risk averse in the extreme.  The best boss I ever worked for combined his visionary strategic abilities with a willingness to take (reasonable) risks in a behavior pattern I have always described as “a bias for bold action.”

Perhaps these aren’t the ideal employee characteristics from the company’s perspective, but they sure helped propel my best boss’s career.  He could readily define a path to a better future and wasn’t afraid of immediately heading down that path even if he had to drag everyone along behind him.  At times his “bold action” upset existing strategies, relationships, and career trajectories.  He made enemies.

And although he was usually right, he sometimes made mistakes.

His bold actions often angered his peers.  His bosses were undoubtedly sometimes frustrated by him.  But everyone recognized his abilities and most put up with the inherent disruptions because he was driving us to somewhere better than where we had been.

As a subordinate, I was inspired.  At times, even in awe.

A talent for strategy, or a skill

I’ve often heard people debate whether we can become better at seeing potential futures and building plans to take us there, or if strategy development is something that is part of our DNA.  Is skill in strategy nature or nurture.

After three decades in business, I have to conclude it is a bit of both.

For a long time one of my employer’s was in the thrall of the Gallup Corporation and several of their leadership consulting paradigms.  One of Gallup’s theories at the time was that people are born with certain, innate strengths (they label these “talents”) and weaknesses.  They further assert that these can only be changed by a small amounts through education, training, experience, and personal development efforts.

In the Gallup world, the ability to effectively see potential futures and devise strategy falls into this category of innate talents.  If you’ve got it, great.  If not, don’t waste your time trying to improve in this area because you’ll just become frustrated and will be lucky to make any noticeable progress.

At the company level, this means that you shouldn’t waste time trying to put into an employee what “God left out.”  If a particular salesperson lacks a critical ability (such as a talent for quickly developing close, trusting relationships) then she needs to be moved to a different job where the talents she actually possesses will be utilized, and those she lacks won’t undermine her success.

Or maybe you should just fire her and move on to someone with stronger “relationship talent.”  Yeah, that would probably be easier.

I found this entire concept to be deflating in the extreme – specifically the notion that if you weren’t born with it, you aren’t ever going to have it.  Nowhere did this theory seem to be more true (at least in the Gallup viewpoint) than in the area of strategy.

Unfortunately, for many of us a talent for strategy is critical to succeeding in the most senior roles in the company.  If you don’t have a talent for strategy (actually, they told me mine was middling), you don’t belong in the company’s most senior roles.

End of story.

But I’m afraid I just don’t buy this.

I took a course in strategy in graduate school.  Prior to that course, I would have been hard pressed to define “strategy.”  I didn’t really know what people were talking about when the subject came up (neither did many of them.)  I struggled with how to think about it.  How to classify it.  The course gave me a framework for the subject, and plenty of examples (case studies) to illustrate how to apply that framework.  As a result, my ability to recognize and devise strategy improved dramatically.

When I went to work for my best boss, he taught me much more.  He explained his thinking on the development and application of strategy in the real world.  And, of course, I had plenty of opportunities to observe his thinking in action.  Some plans didn’t work, but most did (truthfully, sometimes a mix of success and failure can be the best teacher).

Today, I consider myself a pretty good strategist – my apologies to Gallup and the entire hour they spent with me to assess all of my talents, but you guys were just wrong.  And while I might not rise to the level of my best boss, he was an exceptionally talented person when it came to this subject.

You can’t be a shrinking violet

The best strategic abilities will be largely wasted if you lack the nerve to implement.  A lack of action makes even the best strategies little more than interesting, paper exercises.

My best boss was adept at applying his strategies, a process he often described as “placing bets.”  From his perspective, adding value was all about trying new things and making improvements to the business, but he also knew that not everything would work.  In most cases, even a perfect strategy requires a cooperative, predictable environment.

He dealt with this by having multiple strategies and projects running in parallel.  In fact, I saw him set a number of initiatives in motion on the fly.  My best boss had a bias toward taking action as opposed to endless intellectualizing on the subject.

Certainly, not every one of his initiatives was perfectly crafted.  In fact, some of them weren’t even fully thought through.  He repeatedly reminded me, however, that steering the ship is easier with a little momentum.

And the portfolio of risks he chose to carry was completely deliberate.  In my best boss’s mind, this was all about stacking the deck so he would always have more victories than defeats.

Because some defeats are inevitable.

I benefited by watching how he orchestrated the balancing act.  I’d never been reluctant to launch into a project if I thought it held great promise – but I would have been much more impetuous, and much more inclined to put all my eggs in one basket.  My best boss taught me how to think about strategies and their implementation on a grander scale, and also how important it was to get the ball rolling quickly.

This is the original cover for LEVERAGE.

This is the original cover for LEVERAGE.

Pulling it together

Gallup was right about one thing – learning how to take bold action can’t be learned in a classroom.  While you can develop frameworks and ways of thinking in that environment, the core learning is experiential – the kind of stuff you need to be in the middle of to really understand.  Strategy and its implementation is full of subtleties and nuances.

Skill in strategy development and an understanding of its implementation, combined with a bias toward action and the perceptiveness to balance a portfolio of risks – these are the skills it takes to succeed as a high level executive.  Unfortunately for most, these aren’t easy abilities to acquire.  I was able to absorb many of them from my best boss because he was an exceptional person – both with respect to his own skills and in his willingness to take the time to instruct a neophyte.

Arguably, it is the most important reason he was my greatest boss.

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

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To the right is the cover of LEVERAGE.  This novel explores the theft of sensitive DOD designs from a Minneapolis Tech Company, and the dangers associated with digging too deeply into the surrounding mystery.  The tale features first level manager, Mark Carson, and the struggle he experiences as he finds the resources of the corporation aligned against him.  Its sequel, PURSUING OTHER OPPORTUNITIES, was released in May of 2014.  A third book in the series, OUTSOURCED, is in the works.

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