Love-to-Win or Hate-to-Lose? An Analysis of CEO Motivation


I have been asking my successful CEO candidates this question for years – what motivates you more, do you love to win or the hate to lose?    This question was meant to satisfy my own intellectual curiosity since I didn’t necessarily have a preference for which option a CEO candidate would select.

However, I have become more interested in this concept in light of contemplating the similarities between an elite CEO and an elite competitive athlete.  Like sports, private equity is a high-stakes game filled with winners and losers.  And similar to elite athletes, private equity-backed CEOs are under the highest levels of scrutiny and pressure to perform.

In this post I’ll share several discoveries and provide my opinion on which of the two motivators might be more powerful.


  1. INTENSITY MATTERS MORE THAN BIAS. As you would guess, every CEO candidate I have ever interviewed has self-identified as highly competitive.  They love to cite examples such as the need to beat their children in a game of H.O.R.S.E.  Cute but not helpful to understand true competitiveness. The reality is that every CEO is competitive but the question is – at what level of intensity? Competitiveness, like all traits is not binary…it exists along a continuum. Whether they love-to-win or hate-to-lose, the best CEOs are border-line pathological about how they feel about winning and/or losing.  On a scale of 1-10 with 10 being the highest, private equity Boards should steer clear of any candidate who is an 8 or less on either measure.
  2. THE BETTER CANDIDATES KNOW.  In my experience, the better candidates have an instant, authoritative and thoughtful answer to this question.  The lesser candidates often reply with “Hmm, good question.  I guess I’m both” or “if i had to choose…”  As always, self awareness and intellectual honesty are keys to great leadership.
  3. WINNERS LIVE ON BOTH SIDES.  I have interviewed and placed many dominant CEOs in both categories.  However, as mentioned in #1 above, all of the star performers were outliers on the competitive continuum regardless of which category they called home.
  4. I’M OFTEN SURPRISED. 80% of the time I can guess a candidate’s answer by the end of the interview.  However, I’m surprised 20% of the time.  This suggests that Boards should spend more time delving into the concept of competitiveness with CEO candidates to gain a deeper understanding. It also begs the eternal CEO recruiting question — how well does each individual CEO know herself/himself.
  5. CAVEAT TO LOSING.   The best CEOs in the hate-to-lose camp define 2nd place as simply this – the first loser.  Anything other than winning creates an angst-ridden response in these outstanding CEOs.  The finest hate-to-lose CEOs define losing as anything other than winning.  How candidates define losing and winning in their own minds matters…a lot.


You might think that winning is the same thing as beating second place.  It’s not.  The difference is in the emotional response illicited within the CEO.  World class CEOs who miss budget by even the narrowest of margins will feel sheer agony, and therefore drive as hard as humanly possible to avoid that feeling in the future.  When these CEOs win, they do celebrate but the emotion of winning is modest compared to the agony of missing a target.

Similarly, CEOs who love-to-win experience angst when they fall short but the emotion is much less intense than the joy they experience over winning.


Leadership comes in many forms and, as mentioned, there are successful leaders in both camps.  However, if pressed, I will admit a bias for hate-to-lose CEOs based on my own anecdotal experience.

If nothing else, private equity Boards should carefully evaluate a CEOs competitiveness and avoid candidates whose fires burn below a 9 out of 10.

Of course, this level of competitiveness must be mitigated by effective levels of empathy, restraint and judgment…otherwise, Boards will have a completely different sort of failure on their hands.

Execution, Performance Pscyhology

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