Being direct can help clear the air with someone who trusts you. With someone who does not, the same approach can make a difficult conversation harder.
That was one of the distinctions Tim Duggan asked property managers to consider at PM/ONE 2026: understand the relationship before choosing how to handle the disagreement.
Drawing on the research for his new book, Clear in Tension, Tim gave delegates a five-step framework for working through conflict: clarify what matters, listen generously, explore what is underneath, align on a shared direction, and reset your story.
“When you learn how to handle conflict better, you learn how to live better,” Tim said.
Prepare for the conversation
Tim’s starting point was that many difficult conversations are foreseeable. Delivering bad news or meeting someone who is likely to disagree gives you an opportunity to prepare.
He asked delegates to think about a conflict in their own lives and consider two questions: how much trust existed in that relationship, and how closely their values aligned in that situation.
Those answers, he said, place a relationship in one of four “terrains”.
The summit combines high trust with similar values. The arena has high trust and different values, creating room for a contest of ideas.
The swamp describes low trust despite similar values, where people feel they should be aligned but struggle to make progress. The minefield combines low trust with different values, making interactions more volatile.
Tim took delegates through questions about reliability, honesty, confidentiality, and whether they could share bad news without fearing the other person’s reaction.
A second set explored their expectations of a good outcome and the standards they applied to themselves and others.
“The whole point of this is just a diagnostic tool,” he said.
Knowing where a relationship sits helps determine the behaviour to use – directness can be effective at the summit.
Arguing through competing ideas can be productive in the arena. Where trust is low but values are similar, Tim described the value of asking questions, making commitments, acknowledging the other person’s work, and explaining clearly.
For people who tend to avoid conflict, he also shared workplace expert’s Amy Gallo’s reverse risk assessment: consider what could happen if you do not speak up.
Listen until you can check your understanding
Tim’s second step was to listen generously, paying attention to what someone says, their emotions, the interests behind their position, and the values that matter to them.
He described two techniques delegates could practise in their next conversation.
Mirroring involves repeating the last few words someone has said, encouraging them to continue rather than jumping straight to a question or solution.
Looping goes further: you paraphrase what you have heard in your own words, then check whether you have understood correctly.
“Is that what you’re saying? Did I get that right?”
If the answer is no, keep listening and checking.
Tim also encouraged delegates to put their phones aside during face-to-face conversations and allow moments of silence so the other person could keep talking.
Put “how” into the question
Exploring what is underneath a conflict means looking beyond someone’s stated position to the interests driving it.
Tim offered a simple starting point: use “how” in your questions.
“How can we resolve this? How do we get to the bottom of this?”
He said this invites the other person to help work towards a solution; it shifts the conversation towards how something could happen, giving both people a practical problem to consider.
Find shared direction
Alignment begins with looking for something both people care about, even when their positions seem far apart.
Tim encouraged delegates to practise “steel manning”: understand and represent the strongest version of the other person’s argument, rather than attacking its weakest point.
He paired that with compassion and a willingness to reconsider their own position.
“So if you wanna change someone else’s mind, you have to be prepared for your own mind to change,” he said.
Choose how to move forward
The final step, resetting your story, recognises that some disagreements will remain unresolved.
Tim described three possible outcomes: resolve the conflict, repeat the CLEAR process to understand more, or release it emotionally or physically.
He also stressed that people do not need to engage in every conflict.
His invitation was to build the skills deliberately: prepare for a difficult conversation, listen beyond the first answer, and choose a question that helps both people think.
Actionable
- Assess trust and shared values before your next difficult conversation.
- Consider what could happen if you choose not to speak.
- Paraphrase what you hear and check that you understood.
- Use “how” questions to work towards a shared solution.
- Be prepared to reconsider your own position during disagreement.
Tim Duggan’s new book, Clear in Tension, is available to pre-order. Find out more and pre-order the book.