Five Scary Good Questions

In a career spanning 30 years (so far), I’ve learned, sometimes painfully, how to ask better questions.

Most of that learning has come from questions directed at me that I had no good answers for at the time. Depending upon the circumstances and who’s asking them, these types of questions can be scary.

These five are among my favorites to ask yourself and others, depending on your particular circumstances. If you fancy yourself a leader now, or hope to be one day, add them to your toolkit.

1. “What’s our objective here?” Oftentimes people lose sight of the goal in the heat of battle. This is always a good way to re-focus and re-center everyone, including yourself, on the main thing.

2. “What is it that we have that people want that our competitors can’t match?” If you’re in marketing and this one is news to you, ask for an immediate transfer to operations before anyone finds out. If you’re the CEO, you should be asking this question at least once a month.

3. “Why?” This is a cousin to the first question, above. Use this one when trying to get to thinking one level deeper than the obvious. Use this five times in a row if you want to get to the root cause of any problem.

4. “What did you hear?” I’ve learned this one from Chet and the Band at BUILT TO LEAD. Since we all see and hear the world not as IT is, but as WE are, this is a great reality-checking question to make sure everyone is on the same page.

And last of this list, one of the rarest questions in all business:

5. “What did we learn from that failure?” This is one of the least-asked AND most powerful questions on earth. Few are brave enough to ask it because, as John Kennedy once remarked, “success has a thousand fathers, but failure is an orphan.” The truth is, most people scatter when any kind of failure occurs. But healthy, CORE-centered people and organizations make lots of controlled-risk experiments expecting lots of “failures,” and view them as rich learning opportunities. Lead your teams to stick around after failures and ask this question, and many others. You’ll learn a lot.

Do you have any favorite scary good questions to add?

Done so.

Leave a comment