In our line of work, we’re very fortunate to meet a lot of very good leaders. Sometimes we meet early in their career, when we’re trying to define or predict their potential, and sometimes we meet when their proven track record means prediction is no longer required.

Alongside that, I read all the time. Everything from deep academic research (complete with all that formatting) on all sorts of things, from winning, to teamwork in winning, to resilience, to growth, to learning, to outright failure.

And alongside that, I watch documentaries – mostly sports – on how individuals and teams went about getting to elite.

From all that, I know there are definitely two types of winning. One we know and love and talk about all the time.

The other we love even more.

Traditional Winning

Everyone knows what it takes to win in the common and garden-type traditional manner. We know its rare, but we also recognise the pattern easily.

You set a goal.

Learn what you need to know or do.

Make a plan.

Work really really hard.

Climb the mountain.

Plant the flag.

Tell the story in well practiced way of how you did that, humbly mentioning some people who supported you from the sidelines.

This is traditional winning.

The other type of winning

This is winning we talk less about.

You set a goal.

Learn a fair bit, but maybe not quite enough.

Practice and trial a lot.

Fall on your arse.

Give up.

Dig deeper.

Swallow your pride and try again.

Get yourself into a real bunk.

Rely on family and friends who love you to stand by you while you struggle and disappoint yourself, falling short.

Ask complete strangers for advice and help to drag you out of the hole.

And eventually, you come out of the deep hole, climb a mountain, which may or may not be the one you were first aiming at.

And then you ask everyone who helped you get there, to jointly plant the flag with you, as you and they dissolve in happy tears together.
If and when you tell the story, it’s messy and disorganised – lots of highs and lows, and lots of people to thank. While you’re often still working out how it happened, you’re very sure that anyone could have done it.

Frankly, this second way of winning is my favourite.

We all admire winners.

They’re inspiring.

Don’t you love a person who’s blessed with some awesome raw (and/or genetic) materials,  sacrifices everything correctly to deliver their best, plays their career or game perfectly, makes no mistakes, knows exactly the people to surround themselves with to be better, and delivers the incredibly high standard exactly as planned!

People who knew them as kids, knew they’d do it, and they did.

We admire them, applaud them, reward them, and buy their book. We try to soak up a lesson or two, but deep down, we know we really needed to hear their story when we were five years old, not 35, or 45, or 55.

In reality, we all know very few of us are them.

And that’s why the other type of winning ought to get more air time.

What does it mean for leading teams

Look for both types.

It’s not so long ago that ‘Talent’ sheets in big corporations had an ‘Under 35’ page (hopefully, our systematic removal, means we looking at careers and potential now as much more complicated than a straight line from High School to the C-suite). Forbes still has “30 under 30” list, complete with the ongoing debate about its legitimacy, but hopefully, we’re looking more broadly and more interestingly at more interesting dimensions than a birthdate.

As you lead a team, by all means select a few with perfect trend lines, but if you want substance, and grit, and resilience and even prosilience (growth from adversity) select a few that zig-zagged their way to success, via or plus or minus a few deep holes en route.

These people have needed others, so they look out for others, lift others, know what grit looks like, and are happy to help someone who’s giving it a go. They pitch themselves as part of someone else’s success, not the judge of someone else’s success.

These people have had to dig deeper, swallow their pride, and accept their imperfections. They’ll do the same for others. They judge a little less and encourage a little more.

I really do think the best stories in a team are from the people who took longer to get there, have a few more battle scars, and understand the collective nature of success. They’re in it together, enjoying the journey, not just the destination, and enjoying every moment.

So, spot the stars early. Sure.

But leave space to believe in everyone. That everyone, or anyone, might just make it to be great with the right moment in time, context, support, and belief.

What does it mean for culture

Everyone loves an underdog. The messier the more intriguing.

They can see more possibilities, greater alignment to their own imperfect lives and choices. We’re inspired by people who achieve great things despite their human fallibility. We support them, because they need, rely on, and appreciate others. They bring out our best too.

So, culturally, both types of winners are good.

One sets the early standard and the straightforward path.

The other shows us that anything is possible. They are the walking definition of determination and hope coming together.

A final word from Seligman

The father of positive psychology, Martin Seligman, speaks a lot about hope, optimism, and possibility. There’s three quotes from him that I thought a lot about as I considered why we love the under-dog stories so much. They’re not his most famous quotes but they are really good.

“Optimism creates hope…hope releases dreams…dreams set goals…enthusiasm follows”.

“We’re not prisoners of our past”,

“Reaching beyond where you are is really important.”

As human beings we all need hope, and I think that’s why we really like the second type of winning. It’s the story of someone who broke the past to invent a better future. It’s a story we all want, not just for ourselves, but for those we love and those we meet every day. Most of us really do want everyone to win – whatever winning might mean to them.

If you want to think more deeply on this

Here are some things to read:

  • Hidden Potential – Adam Grant, 2023
    • Admiring different types of strengths, and acknowledging different types are important at different moments and different contexts
  • Noise – Daniel Kahneman, 2021
    • Looking at the challenge that we all make noisy, cluttered decisions, with plenty of mistakes, and how we can think about making better ones by acknowledging just that.
  • Antifragility – Nassim Taleb, 2013
    • The original idea that there is growth and positive outcomes in disrupted systems and from disrupted people.

And some things to watch:

  • Mark Cavendish – Never Enough – Netflix, 2023
    • Watch his wife and coach and psychologist believing him to success, long before he believed himself.
  • Zac Williams – any weekend for the Carlton Blues in the AFL
    • Especially his family and teammates, as he thanked them through tears on his 150th game

Love your thoughts.

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