Are You Trying To Win? Or Just Not Lose?

I used to run a yearly innovation conference

Years ago I worked for a company where, every year, we invited the top 20-30 employees (from about 120 folks) to a conference center for an innovation conference. I would spend months planning the conference, from the talks we gave to the team challenges.

Every year we had a final competition. One year I gave each team a set of materials to build catapults. We would see who could launch an object the farthest.

One year I gave each team a set of Lego pieces and they each had to build a vehicle that would compete against another team's vehicle. The competition was a bit like Robot Wars but with less blades.

The vehicle with the most pieces broken off by their opponent would lose. It was a single elimination competition and we started noticing something partway into the ordeal.

As teams progressed closer to the finals, their vehicles had less and less pieces. The final two competitors basically built the same cars – the engine block and four wheels.

They figured out that with less pieces, there was less of a chance for their pieces to fall off, and therefore, they wouldn't lose.

You can see why I titled this post, “Are you trying to win? Or just not to lose?”

Have you ever seen this diagram?

One of the hardest lessons I had to learn in product development and strategy was that using data to optimize my product didn't mean that I was creating the best thing ever.

Have you ever seen an image like this?

When you use data to optimize products, it's easy to create a new version that is 5 or 10% better. And you tell yourself you're on the right track. But it's just as likely that you're nowhere near where you need to be.

The problem is that you will never get in trouble for optimizing for the local maxima. It's slightly better, but everyone feels good.

It's what it looks like, “not to lose.”

But if you're trying to win, you have to risk leaving the hill you're on to find a completely different hill, right?

Are you trying to win?

If you're trying to win, you have to be willing to lose.

If you're trying to win, you have to take risks.

And taking risks means opening yourself up to being wrong or failing.

Three quick examples

  • As of right now, Zeek is re-working their brand. There's risk there.
  • As of right now, Modula is re-working their pricing page. There's risk there.
  • As of right now, Credo is re-working the features of one plan. There's risk there.

You can't win if you don't take risks.

You can just keep doing what you've always done. And that may help you not lose. But it's not the same.

Another example: GiveWP

The GiveWP team recently changed their pricing. They went from a model that sold each extension separately to a model where you could buy different bundles. Of course it was nerve-racking. Would they lose customers? Would they lose revenue?

In the end, without giving you details, I can tell you that GiveWP's move worked.

But the risk was there regardless of the outcome.

How to take good risks

If you're trying to win, and you've decided it's worth taking risks, here are 4 tips for taking risks in your product business.

First, make sure to evaluate your risk

I've told you before that good ideas are only “good” in the context and timing that you make them. No idea is intrinsically good. You need to evaluate the consequences to your particular context. And determine if this is the right time. Don't copy someone else, hoping you'll get the same results. Their context is different.

Second, recognize that failure will happen

I wrote about this on my leadership blog. The difference between people who hit their goals and those that don't isn't tied to skill or intelligence. It's often tied to who planned ahead with contingency plans (plans B, C and D).

Third, make your decisions with a clear head

Remember when I asked you that super important question? Are your emotions serving you? It's a really important question. Because the last thing you want, when taking a risk, is to be fueled by your emotions (and only your emotions).

Fourth, challenge your assumptions

The game is always changing. So that means you have to challenge your assumptions – even if something was true before, it doesn't mean it's true now. If you want to win, you have to make everything available to change. And you have to know yourself, to understand your own bias in the process.

Don't worry about losing. Try to win.

We tell ourselves that we're trying to win. All of us do. Because what else would we tell ourselves.

But it's not always the truth. Sometimes we're just trying to make sure we don't lose.

And that's why I'm writing this to you today. Because you need someone in your life, not necessarily me, who keeps pushing you to face the reality of your situation and suggest that maybe you're holding back.

And that's fine. But let's just acknowledge it.

I've been there. In a holding pattern. Not wanting to mess anything up. But also knowing this wasn't my best life. And eventually a couple friends asked the hard question.

Are you trying to win? Or just trying not to lose?

I'm asking you that today in the chance that you're ready to stop worrying about losing and are ready to go for the win. If so, I'm here to tell you, you got this.

Go for the win!