The Bravest Phrase

Enjoy The Work blog post. The Bravest Phase.

I met a founder recently who quickly won me over. We had a conversation about his business. We bounced around why he started the company, his vision for the future, how his product uniquely works, and the team he’s assembled.

I asked a predictable set of questions. Why did you start the business? With whom? What’s the problem you solve in the world? Why does that problem matter? How do you uniquely solve it? How do you identify prospects? And so on… The discussion hit an interesting point when in response to one of my questions, the founder paused, thought for a moment, looked at me squarely, and simply said, “I don’t know.”

If there was a phrase I wished I would hear more often from entrepreneurs, it’s “I don’t know.”

Those three words have become exceedingly rare. Our culture has conditioned an entire generation of founders to be uncomfortable with the vulnerability required for such an admission.

We are told that we have to know the answers, and we have to share our knowledge with unwavering confidence. That any sign of weakness might put us at a disadvantage. Potential hires will walk away. Competitors will pull away. Investors will ghost. Customers will balk.

It’s crap.

“I don’t know” is brave. It’s real. And it’s an invitation for a discussion from which learning might occur. The moment the founder in front of me said, “I don’t know,” my desire to work with him rose immeasurably.

When someone answers every query with not only a specific answer but (worse) unassailable confidence, my reaction is the opposite of what they likely intended. I only become more cautious, more skeptical. My inner dialogue is always the same:

  1. Do you ever not know something?
  2. Are you allowed to be wrong?
  3. What are you not seeing?
  4. Are others’ opinions valued?
  5. Are you intellectually curious?
  6. Do you have humility?
  7. What skeletons might exist in this business?

However, when I meet an entrepreneur who expresses confidence in some areas but not in others, my mind fills with affirmations instead of questions:

  1. You know what you don’t know.
  2. You listen.
  3. You’re curious.
  4. You’re reflective.
  5. You’re open to others’ inquiries.
  6. You’re someone people can trust.
  7. You’re humble.

Life in a startup moves so fast. You have to act upon incomplete data or risk delay. And delay means death when operating on limited financial and emotional runway.

The earliest stages of startup life are far more filled with questions than hard truths. Yet I meet founder after founder unwilling or unable to simply acknowledge that there are aspects of their business of which they are sure and others of which they cannot possibly be.

Own it. Sing it proudly. That’s when the entrepreneur has a chance to shine. Demonstrate the resourcefulness, deductive reasoning and humility required to jump into the unknown and try and discover something new for themselves.

In fact let me share the full transcription of what the founder in front of me had asked. It was glorious.

“I don’t know yet; how might we figure it out?”

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