When the Questions Matter More Than the Answers

First-time entrepreneurs think their job is to have the right answers.


Your job as the boss is to ask the right questions.

Your job is to start the conversations that produce answers and solve problems.

Unfortunately, the usual time when it is our natural human impulse to ask questions is when something goes wrong -- usually along the lines of "whose fault is this?" But then, the purpose is less to really explore or understand than it is to blame.

A great boss will reorient the conversation and focus on moving forward, simply by asking a better question:

"What does a solution look like?"

"What is your recommendation?"

My personal favorite is to give the person confidence to think about the future ...."Fast forward, a year from now, what will the company look like once this crisis or conflict has passed and what did you do to get us there?"

The key is to start with the end, and work backwards.

The "rear-view" perspective is hard, but very useful. When HighTower was a young startup, we challenged ourselves to approach strategy and decision-making through the lens of an established, successful firm many years in the future looking backwards.

We forced our minds to jump ahead and then imagine following the execution plan back to today. Rather than to think linearly forward, we envisioned our business in the vacuum of uncertainty and forced ourselves to consider: "if we want THAT future, what MUST we do today to get there?"

So, boss, take a minute to make peace with today's difficulties and think about where you'd like to be one, two, three, or 10 years from now. Push your mind into the future, think about what it looks like, then follow the path backward.

And ask yourself this question:

"What do I have to do tomorrow to get there?"