The Leadership Playbook: Asking How Can We

Some leaders have conditioned themselves to play the Devil’s advocate. Whenever a new idea, new opportunity, or something that may be difficult to execute is put in front of them, they point out all the reasons “why we can’t.”

These leaders can perfectly describe all of the reasons why you can’t do something.

• The idea has been tried before and they failed.
• The idea isn’t aligned with the strategic initiatives of the company right now.
• The idea would be too expensive to try even if it could succeed.
• Other people are already doing it. We are too late

They can tell you the new opportunity is too complicated.

• The customer is too high maintenance.
• We don’t presently have the staff to be able to serve the customer you are working on.
• The opportunity isn’t the kind of opportunity we normally pursue, so we are not prepared to handle it.

They can tell you why it’s going to be too difficult to execute.

• It’s going to take more time.
• It’s going to take too much money.
• It’s going to take more resources.
• We can’t afford to fail.

A lot of leaders wire themselves this way by believing it is their role to play Devil’s Advocate. They believe that being realistic makes them a good leader. Maybe it does. But great leaders are unrealistic. Their visions are so big that they frighten other people with their audacity.

Great leaders ask a different question. They ask is “How can we?” They also ask:

• “How can we succeed whether people have failed before?”
• “How would this benefit our current strategic initiatives?”
• “How could we find the money to pursue this initiative?”

When something is complicated, the great leader asks:

• “How can we simplify this and make it work?”
• Or, “Where can we find the people we need to pursue this?”
• And, they ask a really important question, “Even though this isn’t something we normally do, what could this new competency due for other clients?”

It is easier to play the role of Devil’s advocate than it is to play Angel’s advocate. It’s easy to pick apart ideas and run down the people who propose them. The status quo has many defenders, but a leader shouldn’t be one of them.

Not every idea is worth pursuing. And there are many opportunities with prospects that are not worth your time and that you should avoid. But not because something will stretch your capabilities, and not because they will force you to grow.

The next time you reflexively want to explain why you can’t do something, ask yourself instead, “How can we?”