Why is it that we expect ourselves to have all the answers? When I was younger and starting my first business, if someone asked, I assumed I should know the answer right off the bat. If I walked away from a client meeting unclear on exactly what was expected from me, I usually assumed that there must have been something that I ‘missed’. I looked to myself to know all, be all, provide all… without disappointing anyone and without exception.

Sheesh… as I write this, I realize how ridiculous that sounds. But it was the truth… then. Through the years, I learned to get more comfortable with ‘not knowing.’ In fact, the phrase ‘can I find out and get back to you on that?’ became not only a useful tool but also a real growing edge for me. I learned that the honesty of saying ‘I don’t know’ or ‘I’m not sure’ was (almost) always well received. And the few times that it was not? Well, those people were the usually the never-to-be-satisfied-no-matter-what, and not ones I wanted to work with.

After three decades in business, I can tell you that I’m a major proponent of asking questions… many and often. If I’m in a meeting – or even a social situation – where there seem to be a few too many loose ends – I’ll be the first to ask: ‘Just to be clear, could you …’ ‘Will you tell me a bit more about…’ ‘Would you please share…’ ‘What do you expect from…’

This is particularly helpful when you’re being asked to take action. Like making a proposal. Committing to a project. Being in charge of (insert whatever here.)  I know you have questions in your head, but if you don’t ask them out loud, you’ll go away wondering and often unclear.

If your repertoire of questions needs expanding, try writing out a few. And while it may sound silly, practice injecting them into your daily conversations until they flow easily from your mouth. Then you’ll be ready to stop trying to read minds and start asking when clarification is needed!

Let’s just borrow from conventional wisdom and put it this way. Don’t be afraid of ‘not knowing.’ Because before you agree to jump, you need to ask ‘how high?’ Then you can choose whether to take the leap… or not.


Have there been times when you realized too late that you didn’t ask enough questions up front? How did you handle it? I’d love to hear so we can all learn from each other’s experience.