5 Questions to Ask During Tough Conversations

The tipping point between prolonged disappointment and renewed vitality is a difficult conversation.

Many leadership frustrations are the result of conversations that didn’t happen.

The choice to avoid difficult conversations often masquerades as kindness.

the choice to avoid difficult conversations often masquerades as kindness

Are you worthy to lead tough conversations:

Any dullard can sling muck.

On a scale of 1 to 10 (1 being low and 10 being high)…

  1. How deeply committed are you to the best interests of your team members?
  2. How trusting are your relationships? Apart from trust, positional authority, threat, and pressure are all you have. An open heart hinges on trust.
  3. How forward facing are you as a leader? Dabble in the past. Dance in the future. Adapt in the present.
  4. How much do you believe in them?

Any response less than 7 indicates you have work to do before the conversation.

7 ways to prepare for tough conversations, if you’re worthy:

  1. Make a list of their top five contributions.
  2. Make a list of their top three strengths.
  3. Anticipate friction in the form of resistance, distraction, excuses, blaming, or self-condemnation. Resistance is the pivotal moment in transformative conversations.
  4. Wait for the moment of opportunity that begins with, “I don’t know.” If they knew, they’d be doing it.
  5. Prepare for multiple conversations. Tough issues aren’t resolved with one conversation.
  6. Narrow focus. How many problems do you plan to bring up? The answer is one.
  7. Sleep on it. Tired leaders lose perspective.

5 questions to ask during tough conversations:

  1. How might we move toward partnership? 
  2. What does success look like?
  3. Who is responsible for change?
  4. How will new behaviors be designed?
  5. How will we be accountable to each other?

Pierce the veil of disappointing behaviors and poor performance by practicing courageous transparency, kind candor, and forward-facing curiosity.

How might leaders prepare for tough conversations?

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