Answering This Question Makes. I recently met with a client who was planning for a conversation with a senior leader. She was preparing to convey some of her ongoing concerns about the culture of their organization.
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What’s The Outcome You Want?
I asked her this question: What is outcome you want to see come out of this conversation?
She said that she wanted to help the organization correct its mistakes and have a better culture going forward.
I have no doubt that was part of her motivation.
But it wasn’t the full story.
Based on her tone of voice, body language, and facial expressions, I suggested that she really wanted to be heard and acknowledged for the pain she had been through. From what I knew of her situation, she certainly deserved that acknowledgment.
As we talked, it seemed unlikely she would get that from this leader. Based on her limited interactions with them and how they responded to situations like this before, probably nothing of substance would happen.
I offered that she might consider if the political capital she’d be expending was worth it for an outcome she wasn’t likely to get.
Examine Your Motivations
Ultimately, I couldn’t (and don’t) know the right answer for her. My goal was to help examine her motivations so she could craft her best strategy.
I find myself in admiration of people, like my client, who think to engage others at times like this to make better choices. What might seem apparent to others is often difficult or impossible for us to see in ourselves. Effective leaders get beyond themselves with input from trusted mentors, colleagues, or friends.
Bonni (my wife) has been a great teacher in this area. When I’ve struggled to prepare for a difficult conversation, she’ll ask me: What is outcome you want to see come out of this conversation?
This often helps me identify if my current strategy is likely to lead to the desired outcome.
Adjust Strategy To Get Results
Identifying the outcome you want does not mean avoiding tough dialogue. Rather, getting clear on the outcome either focuses the dialogue or helps us identify a different strategy all together.
If the existing strategy isn’t likely to work, variations on one or more of the below can help:
- Begin the conversation differently
- Set aside topics that won’t likely lead to the ultimate goal
- Elect to have the conversation with a different party
- Set the expectation for a lengthier, ongoing dialogue
- Forego the conversation all together
Who Helps You?
Identifying trusted people in your professional and personal life can offer you clarity when you most need it. Who’s a trusted party that helps you clarify your motivations? Respond below.
Identifying the outcome you want, examining your motivations, and adjusting your strategy can make difficult conversations easier. By taking the time to consider these questions, you can approach tough conversations with a clearer sense of direction and purpose.
Effective leaders know that difficult conversations are a necessary part of growth and improvement, but they also know that approaching these conversations in the right mindset is crucial for success. By considering the outcome you want, examining your motivations, and adjusting your strategy, you can make difficult conversations easier and more productive.
Remember, the goal of a difficult conversation is not to ‘win’ or ‘lose,’ but to find a solution that works for everyone involved. By approaching these conversations with clarity and purpose, you can achieve that goal and take your leadership to the next level.

