How to Dance with Tough Issues Long Enough to Do Some Real Good

The deadly sin of tough conversations is going halfway. Discomfort causes some leaders to cut them short.

Work up enough courage to dance with tough issues long enough to do some real good.


Halfway makes matters worse:

  1. Pointing out a problem is helpful, but doesn’t solve it.
  2. Bringing up an issue doesn’t mean others understand it.
  3. Telling someone what to do, doesn’t mean they share your vision. Compliance isn’t commitment.
  4. Ambiguity produces a false sense of success that results in collisions of expectation.

The only thing more important than bringing up tough issues is working them through to useful conclusions.

10 suggested questions to extend the dance:

Always step toward ambiguity and confusion, don’t ignore it.

  1. What talents, skills, or qualities are most important as we move forward? Explore key factors for success.
  2. How will we/you/I make this better? Talk helps. Action is better.
  3. How have we connected with the big picture?
  4. What do we expect from each other?
  5. What’s clear that was confusing?
    • Action trumps theory.
    • Simplicity trumps complexity.
    • Ease, at least in the beginning, trumps difficulty.
  6. What questions come to mind?
  7. What points of reluctance might you feel when you think about next steps?
  8. What has turned this into a positive experience?
  9. What will be different?
  10. When will we follow-up?

Bonus: Project yourself into the future. What are the reasons we succeeded?

The four purposes of follow-up:

  1. Accountability.
  2. Relationship building.
  3. Respect progress.
  4. Clarify next steps.

Feeling uncomfortable with tough conversations may cause leaders to short-circuit success by cutting them short.

Be brief and direct at the beginning of tough conversations. Agree on the reason for the conversation.

Slow down at the end. Pursue clarity with kindness.

How might leaders dance with tough issues long enough to do some real good?