“Yes, You Do Want to Go There” Why Leaders Should (but often don’t) Ask the Hard Questions

black-white-jetty-lightning

You don’t want to go there.

And you really need to go there.

Organizations are full of dark currents.

Words left unsaid in the moment they were needed.

Now rising up unresolved from the corner conversations.

Hanging in the air like clouds full of lightning.

Until they burst on the scene unexpected.

Crashing through our best intentions.

Though you never see it coming.

You knew it was coming.


One of the most important tasks a leader must undertake is to liberate the thoughts, feelings, and beliefs of the people they lead. Yet, if we’re honest, this is also one of the challenges many leaders will avoid or shortcut if possible. Leaving the problem for someone else or some other time. That’s because it’s a lot easier to just move things along  than to deal with them. Think about how this happens every day.

  • The meeting comes to an abrupt end. There is some kind of resolution but not much has been resolved. Lots of head-nodding and agenda-pushing but half or more of the group left in disagreement with the outcome. The rest of the meeting occurs in small groups expressing their discontent for the next two hours.
  • During a staff meeting, the leader delivers the plan for a coming change that will affect the team. The depth of inquiry begins and ends with, “any questions or concerns?”, but this means very little when things don’t go as planned. The leader wonders why they didn’t speak up.
  • The team comes to an agreement on the goals for the next quarter but deep down the leader can sense they don’t really buy it; they just want to be done. No one ever follows through on these things anyway. Rather than push for the truth the leader accepts the outcome and goes through the motions of putting the goals into a nice package for senior management.
  • An employee comes by to express concerns about how a project is going. The leader can sense there is more going on than the explanations being offered. Yet she/he ignores their intuition and delivers sound bites of advice based on past experience. Later, when the project fails or the employee resigns, they wonder what was really going on.

One more question.

One more layer.

Just past the point

of uncomfortable.

And then a little further.

The point where change happens.

The point where the real story is told.

We need leaders who will push the boundary when it would be easier to let it go.


Find the courage to ask the next question. The one that scares you a little. Or maybe a lot. The one that might get a response you really didn’t want to hear but you know you need to hear.

Don’t settle for affirmation when what you really need is engagement.

Don’t stop with compliance when what you really seek is a connection.  

“Does everyone here really agree with this outcome? Do you support the plan?”

“I’m sure this change is uncomfortable. Talk about it. What are you thinking?”

“Does anyone else feel there is a lot of tension and doubt in the room?”

“Do you really believe in these goals? Are they worth doing?”

“Now, please tell me what you are really thinking.”

“What’s really going on? Are you ok?”

“Why is this important to you?”

“What are you feeling?

“What am I missing?”

Don’t leave things hanging.  Get in there. In the muck. Tackle the hard stuff.

Even the emotional stuff.

Beneath the surface is where the real work begins.

Be a leader that goes there.

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