Are you a winner? Your answer matters.

I started this blog on Tuesday November 8 2016 when it seemed the world held its breath.  Who would win the U.S. election and be the 45th President?  After all, the winner’s personality, values and beliefs – in short their leadership – would profoundly affect us all.

Throughout the previous few months, I had found the theme of winning emerging repeatedly through media coverage of elections and other world events as well as in my own life.

Winning is not something I would have identified with for most of my life.  Indeed I would have shied away from it, till it was pointed out to me how deeply embedded winning is into our first world culture. We are all affected by our relationship to winning whether we are aware of it or not. In particular it affects our relationships to others as leader, mentor and role model.

As with all such matters, it is our underlying beliefs which are in the driver’s seat. You may tell your spouse or friend that coming midfield with a personal best was great.  However, if deep down you believe that second place is for first loser, that is the message which will come through loud and clear in your tone, energy and even in the things you don’t say.  Becoming aware of our underlying beliefs means we can evaluate them and change them if they no longer serve us.

Let’s consider four versions of our relationship to winning and then come back to the implications of this for how we lead.

First there’s the Donald Trump version which to me seems to be summed up in his statements “I’ll accept the election result so long as I win” and “I won the popular vote if you deduct the millions of people who voted illegally”.

It’s the version of winning where we need the external result to validate our internal sense of self-worth so much that we rework what happens into stories that reassure us[1].

I suggest we all have our Trump moments when we re-run an argument in our mind till we convince ourselves ‘I did the right thing’ a.k.a. ‘I won’.   I know only too well the appeal of applying this type of balm to my wounded pride.  The dangerous thing is that our need to ‘win’ in this version is insatiable.

This isn’t purely personal.  It’s something we have taught our children with every test and competition.  There’s only one first prize and that’s for the best. People treat you differently (better) when you win it.  This struck me forcibly the first time I won a major competition.  It felt weird… and seductive. Winning must mean you’re a better person, right?  The act of winning (or losing) and being a winner (or loser) are conflated.

Before dismissing this as ‘not you’, note that Marshall Goldsmith[2] identifies ‘winning too much’ as the number one unhelpful leadership behaviour of the most successful people, closely followed by ‘adding too much value’- or needing to contribute your ‘right’ opinion even when it is not wanted or relevant.

Yes I am suggesting that there’s a little bit of Trump in each of us.  The question is whether we are self-aware? If we are, we can change tack.

Still unsure?  Try this question:   How easy is it for people to tell you that you are wrong?

Going back to Marshall Goldsmith: if someone hasn’t given you tough feedback in the last 60 days, you can guarantee people are inhibited from doing so.

Here’s another: Do you endure ‘feedback’ at work or home with gritted teeth or even directly ‘correcting’ their perceptions?  Perhaps, as I used to, you avoid such discussions as being too painful, which is a different version of needing the external result to match my internal story.

Here is a second version of winning which draws on our internal, self-validation.  Some years ago a friend shared with me a profound insight that was essential to him becoming world champion in an Olympic sailing class.

“I used to aim to beat the competition” he said.  “Then I realised this meant all my focus was on them.  Now I simply sail the very best I can.  I find I end up ahead of them anyway by the first mark.  The rest of the race I sail for myself.”

He has shifted from “winning to beat the competition” to trusting his own judgment and skill, based on years of coaching and direct experience.  He shifted from reacting to what others were doing to primarily sailing his own race.  This enabled a significant step up in performance and achievement.

While this is a great example of self-leadership I suggest that it is only appropriate for leading others in arenas where the rules of engagement and desired outcome are known and agreed.[3] The biggest challenges faced by leaders today generally do not fit that description.

I observe that people in the Western World are currently in the middle of exploring a third version of  winning as self-realisation.  How can I be the best version of myself, the best leader, the best shaper of my life?  On one level, it is still about achievement.  How can I live up to my fullest potential as evidenced by external accolades or even internal experiences such as feelings of calmness, clarity, personal power?  It’s still ‘all about me’.

However, as soon as we start considering what it means to be ‘the best version of myself’ we are naturally led to consider our interdependencies on other people.  This is reflected in the old saying that it’s better to have a ‘winning team’ rather than ‘a team of winners’.

When we understand our interdependencies we shift the definition of ‘winning’ from a personal outcome to a shared one.  This is the fourth version of Winning I want to consider.

This is more profound than simply negotiating a win-win outcome.  It involves letting go your need to achieve and trusting in a deeper sense of personal value which comes from giving your worth to something that is larger than you.  It’s the shift to true servant leadership.

Recently I was privileged to hear Mark Bilton[4] describe how he faced the vitriol of franchise owners of Gloria Jeans when the company was facing bankruptcy.  His humility, determination and personal involvement as CEO were essential ingredients in these same franchisees helping to create a turnaround success story.  The company was sold after 18 months for over US$160m.  He was able to bring hope that there was a future worth working for if they all pooled their efforts.  In this story everybody won: the franchisees, the employees, the suppliers, the banks and the customers…. Not to mention the business owners.

Let’s bring all of this back to leadership and how we grow and develop as people leaders.

Our relationship to winning seems to me to reflect stages on a personal journey.  My friend Karyn exemplifies this beautifully.  A 3 time Olympian and world champion she has done something even more impressive (at least to me).  In service of giving back to the sport she loves, she has made the mental shift from competing at the elite level to club level – and enjoying it.  She also generously contributes her time, energy and expertise to complete beginners and works hard in forums at the pointy end of setting strategy for the sport for the benefit of all people, not just the elite.  Her definition of winning has clearly morphed from personal excellence to team excellence to an appreciation of the win a whole community can have through shared passion and engagement.  The world is blessed to have people like Karyn.

The next decade will require all senior leaders to expand how they think about winning and their roles in creating winning outcomes.  Challenges are becoming more obviously complex which means shifting our thinking from seeking a win for a particular interest group to seeking a collective win for all involved.  This is something that President Obama as ‘Leader of the free world’ has been grappling with for the last 8 years in the face of a resurgent Russia, an increasingly powerful China and an ever-complex web of Middle Eastern affiliations[5] – not to mention the social effects of concentrating wealth in the hands of a very few and accelerating concerns around climate change.[6] In simplistic terms the solution has to be built on the insights of all stakeholders.  Therefore no one stakeholder can define what that solution is.

Leadership becomes less a factor of having the right answer and more one of holding the space within which ‘warring’ or competing parties can find common ground, see their role in the current problems and define a new way forward which has wins for everyone.

This involves stripping away ego as it is no longer about me, rather it is about something far bigger than me which I find meaningful.  Think of the movement to end apartheid lead by Nelson Mandela but which came to fruition only with the eventual engagement of P.W. Botha and then F.W. De Klerk.  Or the amazing achievement of all parties involved in creating the Good Friday Agreement for Ireland, which ended decades, indeed, centuries, of violence.

There is an intensely personal, I would say spiritual, journey involved in leading in this way.  It’s not for everyone.  Yet if you seek to be a relevant leader for the future, I believe this last version of winning is one you urgently need to explore.

As 2017 begins and Lunar New Year approaches, I invite you to dedicate time now to an honest appraisal of your relationship to winning and to consider whether this serves the intention you hold for your life, your relationships and the future you seek.  The more people who are prepared to do this, the more we can hope for a resilient future which we actually want – because we can trust that, in all our diversity and quirkiness, each one of us will find ourselves to be a winner.



[1] There’s nothing wrong with seeking external validation, indeed it’s vital to keep us intellectually and emotionally grounded. However, there’s a big difference between confirming whether we are on the right track and seeking public accolades to reinforce our sense of value as a person.  The former comes from a place of open-mindedness where both confirming and dissenting information are equally appreciated.  The latter is part of a fixed and limited mindset, as described by Carol S. Dweck, which inhibits innovation and embeds divisive and even aggressive behaviours.

[2] For a fuller description read Goldsmith’s article  His full list of the top 20 unhelpful habits is at


[3] I would link this to the qualities inherent in Technical Leadership as described by Heifetz, Linksy et al for example here


[4] Humanity in Business conference ‘Authentic Leadership’ Sydney November 30 2016

[5] See for example the Iranian Foreign Minister’s insistence that Saudi Arabia, Iraq, Syria and Iran all need to work together to find a way to peace


[6]  Last year it was reported 62 people held the same wealth as the bottom 50% of our worlds population.  This year Oxfam say it is down to 8 individuals.

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