How I Stopped Being a ‘Know-It-All’ Entrepreneur

networking entrepreneur

Eighteen months ago when I first started my company, guesterly, everything felt brand spankin’ new. And while I also felt like an absolute novice, a friend told me something that stuck: “You are the number one expert in your business. No one in the whole world will know more than you do about your business.” It was exactly the confidence boost I needed…and words I may have taken a little too literally.

As an entrepreneur, I talk to people about my business and product a lot — from my seatmate on a flight to meetings with potential partners, investors and advisors. In fact, it’s the core of my role in the company: I sell people on guesterly and share our mission and purpose. But after the first few dozen times I shared our story or software, I found that I could almost predict the feedback I would receive. The more I started to hear the same exact ideas, the more I started to say things like:

  • “We’ve thought of that.”
  • “I get asked that a lot.”
  • “That’s the number one thing people tell us.”

These responses — all variations of “I already know that" — slipped out unbidden, like silk. Why was that my knee-jerk reaction? Was I trying to prove that I was “smart”? Show I was on top of it? Say their idea or question wasn’t original? 

The answer, of course, is all of the above and more. But here’s the thing: When I responded like a know-it-all, the excited smiles of friendly acquaintances dimmed. Investors and advisors raised their eyebrows. At pitch nights and discussion groups, the flood of ideas and feedback would slow to a trickle.

No matter how I looked at it, my responses didn’t bring anything valuable to the conversation: they were defensive and dismissive.


It turns out that “know-it-all syndrome” is a common phenomenon and one I needed to fix, fast. So I turned to Deborah Grayson Riegel, CEO and Chief Communication Coach for TalkSupport, where she and her team offer “emergency coaching” for big presentations and important conversations. She’s coached hundreds of top executives and shared her five-step plan for breaking this knee-jerk speech habit:

  • Step 1: Pick one (only one) habit to fix at a time — and create a Zero-Tolerance Policy for it
  • Step 2: Be curious in conversation
  • Step 3: Practice listening. Really listening.
  • Step 4: Align your words, tone and body language 
  • Step 5: Remind yourself visually

I had two big events coming up so I was ready to test out Riegel’s steps to change my reactions immediately. First, I banned the whole concept of telling people their thought wasn’t original. I asked my husband and team to stop me (in private conversations) if I started to be dismissive while talking with them. That was how I would enforce Riegel’s “Zero Tolerance Policy.”

Then I came up with a set of good, open-ended questions and conversation prompts to use rather than offering my typical contributions. The one thing they all had in common was curiosity:

  • “That’s interesting. Can you give me some examples?”
  • “What else do you think?”
  • “What do you think could be possible if we did that?”
  • “What are you picturing?”
  • “Tell me more…”
  • “What sparked that for you?”
  • “Who do you know who’s doing something like that?”
  • “If you were me, where would you start?”
  • “What else do you see that I might not be seeing?”

Next, I asked a few friends to let me roleplay out the scenarios I commonly found myself in, especially since I had to practice both asking the questions and then really listening to the answers. Riegel says that a common pitfall is asking questions and then using the other person’s response time to prepare our own comeback. Instead, I practiced staying open to the other person’s ideas, being curious about their perspective and experience and even asking follow-up questions.

Riegel shared a surprising fact with me: people may pay attention to your vocal tone and body language even more than the actual words you say. So I tried to connect my new verbal responses with an “I’m listening” tone of voice and nodding along in agreement. 

Finally, I put written reminders right in front of me. For a roundtable discussion where 300 software experts previewed and discussed our product, it was discreet post-it notes in my notebook. For my pitch, it was the top line on the notecard I reviewed right before I took the stage. “Don’t know it all. BE CURIOUS” became my new mantra as I tried to ingrain the new habit. 

A few months later, it’s made a world of difference in my conversations. Now people get more excited about helping out and spreading the word. And I’m ready to tackle a few other bad speech habits of mine: the “uh,” the too-fast speaking and the question mark that can sneak in at the end of the sentences. But with my handy five steps, I’m ready to conquer — and, to quote Riegel, “say anything better.”

You Might Also Like:
Why I Didn’t Tell My Clients I Was Taking Maternity Leave
How to Start a Business With Your Friend — and Stay Friends
Why is it So Easy for Some to Succeed While Others Fail Miserably?