• Colin Mobey

Is it fair when we all win?

This is going to be a tough one.

I’m assessing a phrase I use all the time. A phrase I love. 

I suspect a lot of you reading this do too.

In fact, it inspired the writing of these articles. I wanted to help aspiring and established leaders think more purposefully about the words and phrases they use in the hope that they’d be able to influence how they went into conversations and the outcomes they got. I also knew I’d get a lot out of writing them in challenging my own perceptions as well as (hopefully) creating some interesting and useful discussion on LinkedIn and expanding my network.

You’d win.

I’d win.

Everybody would win.

A win:win situation.

Love that phrase.


If we are going to really challenge ourselves as leaders it means looking at things that are precious to us as well. Challenging our comfortableness. Seeing if we’ve become complacent. Looking at whether we can add even more value with a different choice.

So, I started to think about win:win.

Now, it’s clearly a very positive phrase. An absolute triumph over lose:lose, win:meh, or win:see-you-in-hell.

There’s some debate over where the phrase came from, but it’s clear it came from a certain scenario: the negotiation.

A negotiation it starts by one side wanting something. They then try to persuade the other that they should give it to them, or help them achieve it.

So, win:win comes into play as a negotiating tactic. “You give me what I want, and you’ll get something out of it too.”

Absolutely nothing wrong with that. Especially in a relationship that’s established, trusted, and respected. It’s a shorthand that clearly states “we’ll both benefit from this arrangement, so we’ll both be motivated to make it work.”

I’ve used it more times than I can count, and it’s been used with me, and I’ve rarely taken offence. 

Occasionally though, I've found myself nodding along. Wondering what's truly in it for me. Especially when I’ve not come up with the proposal.

See, when you use the phrase win:win it puts the emphasis on you being successful.

Then there’s a colon (or a hyphen or a slash, but something that indicates there is a separation between you and the person(s) you’re talking to).

Then the other party.

Win (you first): Win (then them)

I’m being pedantic I know, but this plays into the intent you have, maybe subconsciously when using the phrase.

How many times have you been in a room with someone trying to sell you something and they pop out the phrase win:win? Do you immediately go “oh, great. This sounds amazing,”, or do you think “okay, I can see how you get something out of this, but let’s keep talking and see where it goes.”?

It's sets the intention that for this to be successful you must both win.

Winning means you keep going until you cross the finish line. 

Losing is failure.

So, here’s the rub.

Sometime I don’t think we mean, or should mean, a win:win scenario.

Sometimes what we should aspire to is simply a fair scenario.

If we push for a fair scenario then you are prioritising the outcome—not for any particular party, but for the overall outcome. That may mean one side benefits more. It may mean one side doesn’t actually win and is prepared to step back—but here’s the critical point:

No one loses.

If the other party wins big, but you’ve invested a sensible amount and discussed with them it’s not worth you going any further—then you’ve still had a fair outcome. Expectations were set from the beginning.

I suspect you’ll have learnt a lot, not overly spent time and money, and most importantly made a fantastic connection based on trust.

You've not 'won' but you've not lost either.

Fair means no one loses. 

I don’t think leaders should stop saying win:win. I still love it; it still has a place in our vocabulary. It’s powerful and meaningful when used purposefully.

Every now and then though, when I'm looking to build trust rather than rely on established trust, I’m going to propose we work together for a fair outcome instead. 

Feels fair.

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©2019 by Colin Mobey