If there’s one constant in leading people, it’s difficult conversations. Whether you’re providing feedback, conducting performance reviews, differing in leadership style, or trying to come to a consensus on the next steps for a major project, these conversations can often feel more frustrating than helpful.

You’re likely making these conversations more difficult than they have to be, in ways that might surprise you. I’ll coach you on this good news – bad news insight, with practical tips that make high-stakes conversations more productive and help you approach difficult discussions from a place of inquiry.

“The single most important thing [you can do] is to shift [your] internal stance from ‘I understand’ to ‘Help me understand’. Everything else follows from that.” – Douglas Stone, author of “Difficult Conversations”

Coaching: You are the reason conversations become difficult.

Before you begin to turn your difficult conversations into productive ones, get curious about why these conversations become challenging in the first place. The foundation of this conflict stems from the realization that we are all sense-makers.

I coached you on the idea of sense-making in the March edition of Free Coaching. In every moment, you are interpreting the words and actions of others, independent of them. You are also predicting the outcome of a conversation based on your opinions, your observations, and your past experiences. And the other person? They are doing the same thing. To put it bluntly, our different, individual interpretations are the fundamental reason conversations become difficult.

To overcome this complex challenge, consider approaching the difficult conversation from a place of inquiry. Practice moving from a unilateral, “I” stance – “To maintain my authority overall, I need to stay ‘right,’ so I can’t give up any ground on this” – to a more mutual, “we” stance – “We need a fuller picture of the real issues at stake here.”

You’ll end up frustrated if you’re trying to use conversations as an opportunity to prove that your interpretation of a situation is “right.” As the leader, you have the opportunity to create a conversation where it’s safe to explore your different, individual understandings, to ask questions without interrogating, and to present different perspectives for a fuller solution. This requires authentic curiosity, a truly inquiring attitude.

Practice: What can I try?

While popular strategies to create more productive conversations vary, most of them have a common foundation: seeking more information, even if it challenges your personal stance.

I coach my clients often on one of the most common types of difficult conversations – a “What Happened?” discussion, exploring how and why the results of a project or situation veered significantly from our expectations.

In this type of conversation try approaching it like detectives, effectively and objectively gathering as much information as possible.


Point fingers at who was responsible (“Just own up to it and let’s move on…”) dfc6686b-9a7f-49ec-b72e-7f00870dd0cc.png
Interrogate each other (“How could you think that made sense?…”) 0bfdcdeb-5977-479a-b5da-67a23735b9df.png
Use threats (“If this happens again…I’m sure you’ll do it better next time…”) or dfc6686b-9a7f-49ec-b72e-7f00870dd0cc.png
Indirectly discourage (“If you needed help you should’ve asked for it…”) 0bfdcdeb-5977-479a-b5da-67a23735b9df.png
Recreate the path of decision-making (“Are there weak spots in our process, what did we miss?”)
Identify the assumptions that weren’t shared (“I assumed it would…”) and
Uncover unspoken expectations (“You should’ve known, you ought to have, every other time…”)
Identify ways to reinforce each other (“Where could we have been more useful to each other?)

During your exploration, aim to:

  • Look for process glitches you can iterate on, or hand-offs where responsibility or follow-up was unclear,
  • Ask questions aimed at an exploration of people’s reasoning (Remember, we’re all sense-makers, so there’s always an interpretation driving our behavior.),
  • Avoid questions that can be answered yes or no, or that invite excuses.
  • Resist responding with some form of “that’s ok” or “I’m sure it won’t happen again” if someone is courageous enough to take responsibility. Instead, hold your inquiring stance and respond, “thank you for acknowledging your part, I think we found a way to improve our process together.”

Once you’ve reviewed what happened objectively, you can ask:

  • How did you attempt to address the problem?
  • What guided your decision-making on this challenge? How are you thinking about it now?
  • Where were things more difficult than they needed to be? What dilemmas presented themselves?
  • What assumptions contributed to this difficulty? How did you contribute? How did I contribute?
  • What expectation can we go back to? How could it have been clearer or better shared?
  • What new or revised policy or process could help us in the future?
  • How could you/we smooth this out going forward?

The key with these questions is to remain in a place of inquiry, rather than defaulting to blame or interrogation. When others feel they are an active part of the conversation, not just the subject, and are able to take responsibility rather than just take the blame, even our most difficult conversations can become truly productive.

Developmental Challenge:

No matter what kind of difficult conversation you’re facing, focus on staying curious instead of staying “right.” Use the template below to share more productive feedback that reflects on the impact of own behavior on the dynamics of a particular situation and that helps you move from a unilateral stance to a mutual one.

Behavior > Dynamic > Role > Opportunity


  • Behavior: When we [behavior/observation],
  • Dynamic: The work overall is [result/impact].
  • Role: This matters in my role because [importance].
  • Benefit: An improvement in this will [provide opportunity/benefit].
  • Improvement: Let’s figure out how to get better at [improvement].

Example: When we interrupt each other, the work overall slows down. This matters in my role because I need to hear all the perspectives and to move decisions forward. An improvement in this will make us less frustrated and get us to decisions faster. Let’s figure out how to get better at focusing our thoughts and listening to each other.”

Digging Deeper:

Learn more about expanding your leadership capacity with this additional resources:


  • Power Athlete Radio: Luke Summers and Tex McQuilkin of Power Athlete, take me through my paces with their banter and deep diving questions. They invite me to discuss how to explore your own limiting beliefs that are inhibiting your leadership development. They are highly interested in how leaders can get better at leading people toward a common goal. If your leadership style is to seek obedient people, the growth of your project or goal will only suffer. In this episode, I also take the hosts to task, using a series of exercises to push their working partnership – exercises you can use in your own leadership roles and partnerships. As Power Athlete fans would say, this listen is for “savages only.”

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