Note from Art: more than half of my time on emerging and senior leader coaching calls is invested in the topic of challenging conversations. I’m kicking off this weekly Sound Bytes series (of less than 500 words) to share tips and approaches to help you create value from these important moments when you engage others on tough topics. Use the ideas in challenging conversation health! 

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Those striving for success as managers and leaders understand the importance of engaging in challenging conversations. They know in their guts the costs associated with delaying them. After all, tough conversations are where problems are solved, relationships mended or formed, and ideas and innovations are born of creative tension. 

During my coaching calls with leaders at all levels, much of our time is invested in how to engage and structure the conversations to uncover value for all parties. Here are some tips to help you pre-think and design your discussions to achieve successful outcomes for all parties.

Design Your Challenging Conversations for Success

One of the areas many get into trouble is diving into tough conversations without a plan. While spontaneity is suitable for many situations, a bit of pre-planning is ideal for challenging conversations. Ask and answer the following before you engage:

  • What did I observe (behavior), and what was the impact of what I observed?
  • What is the ideal outcome of this conversation?
  • What are my assumptions about the other party’s perspective on this topic?
  • What’s my framing on this issue?
  • How will I open the discussion and frame it without triggering the Lion-Effect (fight or flight) in the other party?
  • How much autonomy on the approach or solution am I willing to defer to the other party?
  • What question will I use to engage them and gain their insights and ideas on the situation (see below).

Use Questions Skillfully to Prompt Solution Development (and Don’t Make Excuses for Them)

I encounter excuse-making with well-intended managers all the time. To reduce the tension, the managers rationalize why the individual did something that merits strengthening or changing. Worse yet, they often blame themselves.

Instead of throwing yourself under the bus or hemming and hawing as you rationalize out loud why someone did something that didn’t work, try asking these four questions:

  • Did you achieve the outcome you were after with this situation?
  • What would have been your ideal outcome here?
  • What might you do differently the next time you encounter a similar situation?
  • What do you need from me to help you in future situations like this?

The Bottom-Line for Now:

Quality conversations of every form are a dialog. Please don’t make the all-too-common mistake of turning the situation into a rambling monologue and expecting the other party to understand your intent or what they need to do differently. Spend time pre-planning the conversation and pay particular attention to identifying the questions essential for promoting a dialog. And then create solutions together! 

Art's Signature