How Atlassian's Dom Price makes difficult conversations easier

Executive overview

Most people dread difficult conversations and over-prepare for them. The label itself creates the problem — calling something a "difficult conversation" raises the stakes before a word is spoken.

Reframe feedback as a gift, ask more than you tell, and never delay bad news.

Reframing the conversation

• Labelling a conversation "difficult" primes you for conflict before it starts
• Treat feedback as a gift: if intent is good, sharing an unseen truth genuinely helps
• Ask "what happens if I don't say this?" to shift from avoidance to purpose
• Charge in with questions, not answers

Preparing well

• Check your own biases — the halo effect distorts repeated observations
• Ask yourself what might be going on for the other person right now
• You know only a fraction of their situation; assume less, inquire more

Staying curious in the moment

• Open with their view first: "How did you think that went?"
• Genuine curiosity about their read reveals what signals they're taking in
• Trying to persuade someone they're wrong turns dialogue into a monologue
• "Tell me more about your situation" opens the conversation; "here's why I'm right" closes it

Handling fact-based hard conversations

• Facts remove opinion: "You didn't hit your target" is not "I think you fell short"
• After stating the fact, check in: "How does that make you feel?"
• Their response tells you which conversation to have next — reset or exit
• Offer a genuine choice: work toward thriving here, or plan a graceful exit

Timing is everything

• The gap between the event and the conversation makes it feel like an ambush
• Address a missed target close to when it happens, while context is fresh
• Bad news does not get better with time — delay removes the chance to course-correct