Maybes are Killing Your Startup

The path to success is paved with clear outcomes, good or bad. Most startups fail not because of their failures but because they are stuck in the middle, in what I call the maybe zone.

It's not hard to come up with new ideas, experiments, features for products, or other means of distribution. What's hard is moving through them with enough velocity to learn your lessons and achieve sustainable growth.


Most people think that a "maybe" is better than a "no," but that's seldom the case for startups.

The Maybe Zone

That's the place where you didn't create an evident success or an apparent failure. It's a dangerous predicament that slows your momentum and silently exhausts your energy. A yes and a no are both excellent—get them fast.

What's killing you are the maybes.

  • "Maybe we're going to do it."
  • "Maybe this was not that bad..."
  • "Maybe when we continue, it might be a good thing..."

In the "maybe" zone, decisions are often made based on irrational emotions, strong opinions, and questionable interpretations of data.

Hopeless Optimism

Entrepreneurs, startup team members, and salespeople are all hopeless optimists. We always look at the potential; we always see the possibilities.

Let's say you've embarked on a new marketing initiative. You've invested much work into preparing and executing it, but the results are disappointing. They're not moving the needle as much as you hoped.

What do you do?

Most of us tend to think that the needle has moved a little bit (even though much less than expected); we tell ourselves: "Maybe we just need to push a little harder to turn this into a success!"

But rather than pouring more resources into the initiative, we should often cut our losses and move on to something else.

What's Your Plan B?

Don't just go into it blindly when you embark on a new project, start a new initiative, or run a new experiment. Don't just say: "We'll try it out and see if it works!"

Determine these three things in advance:

  • What will success look like? (What results/numbers/specific outcomes)
  • What will failure look like?
  • What will you do if the outcome you create is somewhat in the middle?

It's important to make these decisions before starting the project so that you know what to do once it is concluded.

Before you embark on a new project or initiative, define how you'll determine success or failure. That's when you're in the best position to make a good judgment call—not after you've already invested a considerable amount of resources into the project.

It's a way of protecting yourself against the sunk cost fallacy (and yes, this cognitive bias is just as strong in smart startup folks as it is in Wall Street hotshots).

Maybe Kills Sales Team Performance

In sales, your job is to create outcomes: yes or no. You win and lose deals, and both are good.

Optimize first and foremost for speed and clarity.

Don't try to optimize for the maximum possible conversions. It's not about getting everyone to buy, everyone to agree, every deal to close.

Because if you try to optimize for the best conversion rate possible, you'll waste too much time and energy waiting for certain deals to close... maybe! You're going to wait around and let the prospect "think about it," let them extend their trial again, let them delay the decision to next quarter... and the next... and the next—all to avoid a no, because that would be a lost deal).

Their indecision will take over all your mind space, your pipeline, and the mindshare of your team. Like a slow poison, it will slow down and finally kill your momentum. It's a waste of resources.

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