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How To Explore The Tough Questions

How are you at asking the tough questions?

As a leader, much of your job is in asking the tough questions. This differentiates leaders in a big way. By ducking the big questions, conflicts remain unresolved. Hidden agendas remain hidden. Team coherence suffers when too much is kept secret. People start acting in ways that are counter-productive and misguided because the lack of clarity has taken away the guidance they seek.


Sometimes we need to ask the tough questions.

Who should a leader ask the tough questions?

- Team members
- Peers
- Leaders above
- Constituents all around you
- Customers
- Regulators
- Even the competition

What are the tough questions?

The tough questions are those you probably already know but may feel uncomfortable asking:

- What's going on?
- How are you in that big project?
- Where are you in achieving those goals?
- What will you do if your resources come up short?
- Where will next year's customers come from?

... and many, many more. The tough questions have no easy answers and usually involve more work. But the questions and the issues are there whether or not you know about it. Whether or not you know what they're thinking, they're still thinking what they're thinking.

Centered leaders don't back away from the tough questions.

Centered leaders explore tough questions with courage and compassion -

  • the courage to raise a difficult issue and face it head on
  • the compassion to listen thoroughly to the views of others and delay reaching conclusions on their content or their character.
Look at your conversational partner with respect. Listen carefully to what they have to say. Hold off on judging them so that you can learn all of the relevant facts and feelings by asking every question you need to ask. See where they're at, and ask what they would do next.

It could possibly be the biggest and best thing you do as a leader this week. When will you start?

-- Douglas Brent Smith


Learn more in the workshop: Communicating for Results


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