How to Make Big Career Decisions: Don't Tack to Cover

By Nathan Bennett and Stephen A. Miles

We recently heard from a young man who was choosing between summer internship opportunities.  He was in the enviable position of needing to select among offers from three well-regarded consulting firms.  There was no shortage of advice from his classmates; they were unanimous in support of one firm because “that’s where kids from our college go to intern.”  He knew our work on career strategies and wanted to see if we had a different take.  We do.

Over the course of your career, you will make dozens of career decisions like this one.  Since you only get to move through life once there is an understandable desire to try to make each career decision the “best one.”  The difficult thing is that maximizing returns on decisions like “which college is best for me” is impossible.  There are simply too many unknowns.  Which of the school’s outstanding professors will you actually get to have for a class?  What extracurricular activities will offer you great leadership development opportunities?  Where is the classmate who will become your co-founder in the biggest college-incubated business idea since Facebook most likely to be?

Because of these unknowns, employing a rational approach to the decision—like this young man was no doubt learning to do in school—is a fool’s errand.  In cases like these, such efforts only provide comfort to the degree you let yourself be fooled about your ability to know the unknowable risks associated with each choice. At the same time, leaving the decision to the flip of a coin is also not a winning strategy.   Fortunately, we think we have an approach to offer that beats a coin flip by focusing you on your situation, as well as your strengths and weaknesses.

Back to this young man. He wanted to know what he could do when faced with a decision like this.  How could he know which choice would offer him the best return?  We responded by first sharing one of our strong observations from years of research on successful careers: It’s not always the best career strategy to follow the crowd.  Sometimes getting ahead requires the courage to break away from the pack.  Because we knew the young man was an avid sailboat racer, we asked him if “tacking to cover” was always the best strategy when he raced.  He keyed in on our meaning immediately.

Whether or not to tack to cover is a strategic choice sailors make every time they race.  Since sailboats can’t sail directly in to the wind, boats racing to an upwind mark must work their way upwind by zigzagging—what sailors call tacking—back and forth.

In a race, several boats will be working in such a manner to be the first to reach the upwind mark.  Here is where strategy comes in to play.  At some point during this leg, the captain of one of the boats will decide it is time to tack.  Immediately, every other captain has to decide whether it is better to continue a bit farther on the current course or to tack to cover.

What drives this decision?  If the captain tacks to cover he expects to experience the same sailing conditions enjoyed by the lead boat—tide, wind, and current should be largely the same. Tacking to cover means the captain thinks the boat and crew have what it takes to out sail the other boats; taking to cover effectively holds other factors, such as weather conditions, constant.

On the other hand, by continuing on course a captain is betting the wind, tide, and current will be at least as favorable as, if not better than, those experienced by the tacking boats.  Staying on course provides an opportunity to make the most of not just the talent of the crew but hopefully unique and positive sailing conditions.

So it is clear to a sailor that tacking to cover is safe, but it does make it more difficult to create a separation from the other boats.  The strategy makes sense when you think your boat and crew are unequivocally better than the others—you should emerge as a winner with everything else held constant.  But if you are not sure your boat and crew are superior, sailing on alone may provide lift that the others won't experience.

In our study of career decisions, we see so much tacking to cover.  It begins very early in life, but perhaps for adults the first example is deciding to go straight from high school to college, like everyone else.  Some, though, opt for a “gap year” experience that might provide them lift to create separation from the competition as they move on in their career.

Tacking to cover happens when people take internships because “that’s where people at their school go.”  It continues when people with three to five years of experience begin to see their colleagues at work talk about returning to school for an MBA.  MBA brochures begin dotting the cubicle landscape, discussions of school rankings and tuition costs begin to become part of the daily conversation.

As you think about how to develop and deploy a career strategy that will help you get quickly to an upwind mark, this is the central question you must face.  It isn’t that getting an MBA or pursuing a popular internship are bad ideas.  It is just that they may not be very instrumental in your efforts to distinguish yourself from others. For your best move, what you have to decide is simple.  When you are confident that your boat and crew (or, outside of that metaphor, your résumé and talent) have what it takes to outsail the others, then career moves that represent tacking to cover make sense.  On the other hand, if you are not convinced you can win by copying the strategies of others, then tacking to cover is a bad move. In this instance, you are better off making career moves that head you in a different direction, where you can enjoy unique experiences that you can use to differentiate your résumé, and develop your talent, to win in the future.

We are quick to agree that properly understanding risk may be one of the skills that differentiate truly remarkable executives from merely successful ones. Remarkable executives are able to exploit risk to their advantage. They create wins by seeing the opportunity where others fear to tread. They know how to use opportunities to set off on their own course to tell stories that differentiate them in meaningful ways from competitors.  That is how they separate themselves from the competition.  Tacking to cover is safe—you likely won’t finish second by a larger distance than that you already trail by.  Setting a course on your own and making the most of what those conditions provide may be your best strategy for coming in first.

Nathan Bennett is the Wahlen Professor of Management at Georgia Tech. Stephen A. Miles is Vice Chairman at Heidrick & Struggles. The two are authors of the recent Stanford University Press title Your Career Game.