Asking the right question at the right time is an art. As my good friend Melissa Rosenthal says, it takes practice and when you get it right, it pays off in spades.

Over the years I have learned that the ‘right’ questions often have three dimensions;

  • They are open (cannot be answered by a simple Yes or No);
  • They require thought and are delivered with context; and
  • They contain an element of reflection (they require the person answering to explain their logic).

I have also become reliant on asking these questions for two reasons, both of which have to do with self-awareness.

The first relates to pursuing a problem.

Like most people I have biases and like most entrepreneurs, I come with high levels of built-in conviction for the problems I want to solve.

The problem is that bias multiplied by conviction creates a potent combination that narrows the aperture to how one considers the history and future possibilities for the business model they are building.

First-time founders often suffer from this. The few that don’t have a habit of continually asking questions. They and their more seasoned colleagues know that their rate of learning is driven by thoughtful disagreement which in turn is driven by regularly asking ‘why?’ and other well-considered questions.

Building mission-driven teams is the second reason I strive to ask the ‘right’ questions.

I believe that a culture of radical transparency is one of the most important preconditions for creating a place that attracts the best people to do career-defining work. It also helps determine those who may not be a fit. In any case, this can only be achieved if every team member feels like they can ask well-considered questions to anyone in the organisation.

If this principle appeals to you, I recommend adding Kim Scott’s audiobook called Radical Candour to your listening lineup.

The Question I Ask Twice A Year

Here it is and I love asking it:

What could I do or stop doing that would make it easier for you to work with me?

This is the one question I ask co-founders, teammates, partners, customers and investors twice a year. The answers are always useful and if you listen, learn and evolve as a consequence, the answers change over time. And that’s what you want.

Expect people to have this ponder the answer before delivering their response.

One Last Thing …

There are two keys to receiving thoughtful answers to this question.

First, explain that you expect radical candour and no sugar coating but that if you were answering the same question, your objective would be to deliver the message in a way that shows you care personally while challenging directly.

Second, ask your team to ask you the same question.

I have benefited significantly from asking this question and I hope it helps you too.