Difficult conversations
For: Anyone who has hard things to say at work
Every manager has the conversations they're avoiding. The pattern of avoidance is more visible from the outside than from the inside. A 10-question check on whether you actually raise hard things, stay in them, and follow through.
- 10 questions
- 3 dimensions
- ~3-4 min
- Self · Peer · Both
Difficult conversations come in three phases — raising the hard thing, staying in the conversation when it gets uncomfortable, and following through after the air is back to normal. Most managers fail at one specific phase consistently. From the inside, the failure is invisible (you tell yourself the conversation went fine, or that the topic wasn't really that important). From the outside, the pattern is obvious and accumulating. This template surfaces which phase you skip — and what your team has learned to expect from you in tense moments.
How it works
Run it on yourself first — be specific about a recent hard conversation (or one you avoided). Then send it to the people closest to those moments — direct reports, peers, your manager. The gap between your view and theirs almost always points to the phase you're skipping.
What's inside — 10 questions across 3 dimensions
Raising hard things
whether you bring up uncomfortable topics or let them stew
Staying in the conversation
whether you stay curious and open when challenged, or shut down / get defensive
After the conversation
whether you follow through, and whether the relationship survives intact
The questions, in full
Every question is included below. You answer them yourself first, then send the same set to the people who've seen you work.
Raising hard things
- Q1Rating (1-5)
When something is bothering this person, they raise it — they don't let it stew or come out sideways.
- Q2Rating (1-5)
This person doesn't postpone hard conversations until they explode.
- Q3Open answer
What's a conversation this person has been avoiding for a while? What do you think is making it hard for them to start?
Staying in the conversation
- Q4Rating (1-5)
In a hard conversation, this person stays curious — they don't shut down or get defensive.
- Q5Rating (1-5)
When I push back, this person actually considers it — they don't just wait for me to finish.
- Q6Rating (1-5)
This person can hear hard feedback without making me feel like I shouldn't have brought it up.
- Q7Multiple choice
In a tense moment, this person typically...
- — Stays present and steady — the conversation can keep going
- — Gets quiet but stays in it
- — Shifts to defending or explaining
- — Tries to redirect to a softer topic
- — Lets the moment dissolve without resolution
After the conversation
- Q8Rating (1-5)
After a hard conversation, this person follows through — what they said they'd do, they do.
- Q9Rating (1-5)
After a difficult exchange, this person preserves the relationship — there's no chill or distance afterward.
- Q10Open answer
After a hard conversation with this person, what tends to happen — do things actually shift, or do they go back to the same pattern?
The research behind these questions
Drawn from Kerry Patterson and colleagues' Crucial Conversations on the mechanics of high-stakes dialogue, Susan Scott's Fierce Conversations on directness without aggression, Heen and Stone's work at the Harvard Negotiation Project (Difficult Conversations) on receiving feedback well, Daniel Goleman on emotional regulation under stress (HBR), and CCL research on derailment under pressure. Each question targets an observable behavior — not vague 'handles conflict well' rating.
References
- — Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler — Crucial Conversations
- — Susan Scott — Fierce Conversations
- — Douglas Stone & Sheila Heen — Difficult Conversations (Harvard Negotiation Project)
- — Daniel Goleman — Emotional Intelligence framework (HBR)
- — Center for Creative Leadership — derailment research
Ready to run this round on yourself?
Sign up, pick this template, answer it about yourself, and send the same questions to the people who've been in the room with you. The gap between your view and theirs is where the actual learning lives.