Entrepreneurs like to have all the answers. We love to be seen as smart, as in the know, as super savvy. Answers help us get clients, and partnerships, and funding. All sorts of goodies.

Having the answers is great.


Acting like we have the answers when we don’t isn’t helpful at all. , The Million Dollar Question: “Is it working for you?”

Here’s an example:

In an earlier chapter of my professional life, I coached women to better health. More times than I can count, in our first session, a new client would sit across from me and tell me about all the vegetables she ate every day and the protein shakes she drank and the 30 miles a week she ran and the 8 hours of sleep she got every single night. Her opening remarks made her sound like a textbook example of healthy living, but this was coming from a woman who was hiring a health coach because she wanted to see changes in her health.

It just didn’t add up.

As I wondered what else she could possibly do…I discovered the missing link. The new client was telling me what she knew she should be doing rather than what she actually was doing.

So here’s what I learned to do as her coach. When she’d finished outlining all the virtuous habits she was ostensibly practicing, I would gently ask her a single question:

“It sounds like you know just what to do. So how is it working for you?” , The Million Dollar Question: “Is it working for you?”

She’d fall silent. A moment would pass. And then she would often burst out laughing. “Oh my goodness, It’s not! I’m not at all where I want to be!”

, The Million Dollar Question: “Is it working for you?”

We’d take a deep breath together…and then our real work would begin. She could drop the pretense of having it all figured out and get honest with me about what wasn’t working for her so I could help. That one question changed everything.

Being honest about what’s not working isn’t easy. It makes us feel vulnerable. We’re ashamed that we’re not where we want to be. And on top of that,

We’ve trained ourselves to have the answers rather than to sit with the questions. , The Million Dollar Question: “Is it working for you?”

As entrepreneurs, it’s especially important to admit it when…

Read the rest of this post on Best Kept Self, where I am a featured contributor.

1 Comment

  1. […] about why it’s so important to admit it to ourselves when something isn’t working. (Here’s that post in case you missed it.) The post struck a chord, and lots of you asked….but what […]

Leave a Comment