Prepare for a difficult conversation.
Answer five short questions. You'll get a structured prep sheet to read before you walk in the room — or before you send that message.
Prep Sheet
Conversation with —
The Situation
What this is really about
Your Intent
What you want them to know before you start
Suggested Opening
A way to begin
The Goal
What success looks like
What to Watch
Your worry, named and ready
A note before you go in
Take it further
Generate a script you can use
Turn this prep into actual words for the conversation. A draft you can read aloud, edit, and walk in with.
Resources
Checklists, frameworks, language scripts, and a record for each conversation. Open what you need.
Before any difficult conversation. The preparation you do in the ten minutes before is often worth more than the thinking you've done for weeks.
Three structures that work. Use them as skeletons, not scripts — the point is to stay anchored to what's observable and curious about what you don't know.
SBI — Situation, Behavior, Impact
For giving specific feedback clearly
Name the context (when, where), describe the observable behavior (not the interpretation), then state the real impact. Keeps feedback factual and separates what happened from what you think it means.
"In Monday's team meeting [S], you spoke over Priya three times before she finished [B]. It's leaving her reluctant to speak up, and the team is noticing [I]."
DESC — Describe, Express, Specify, Consequences
For conversations where a behavior needs to change
Describe the specific situation. Express how it affects you or the work. Specify what you need to be different. State what happens if things change (or don't). Works well when the ask is concrete.
"When reports arrive after 6pm [D], the team can't prep for the morning [E]. I need them by noon on Fridays going forward [S]. If that works, we can plan the week properly — if it doesn't, I need to understand what's blocking it [C]."
Curious Before Certain
For conversations where you don't have the full picture
Start with what you observed, then ask before you conclude. Even when your read is accurate, hearing them out first changes what’s possible in the room. This framework helps you hold your interpretation lightly — so you can be right and still genuinely curious.
"I've noticed [X] over the last few weeks. I want to understand what's going on from your side before I share my read on it. What's been happening?"
Ready phrases for the moments that usually come out wrong. Edit to fit your voice — the goal is directness without cruelty, and clarity without coldness.
Opening with intent
"Before we get into this, I want to say something. I'm having this conversation because I care about how things go for you here — not because I want to catch you out or make this hard. Hold that, even if what I say next is uncomfortable."
When they get defensive
"I hear you, and I'm not trying to dismiss that. Can you say more? I want to make sure I understand your side before we go further — I may be missing something."
When the room goes quiet
"Take your time. I'm not in a rush, and this conversation matters. [Pause.] What's coming up for you right now?"
When they say "this is the first I'm hearing of this"
"That's on me — I should have said this sooner and more directly. I've been signalling it, but I haven't named it clearly. I'm naming it clearly now."
Closing with clarity
"Before we finish — I want us both to leave clear on what we've agreed. From my side: [what you committed to]. From yours: [what was agreed]. Does that match what you heard?"
The conversation is not the end. What happens in the 48 hours after often determines whether it landed — and this is where the care you’ve put in gets to show.
Immediately after
Write it down while it’s fresh
In the ten minutes after, note what was said, what was agreed, and how they seemed. Not a formal record — just enough to be accurate when you follow up. Memory is unreliable and selective, especially after an emotionally charged conversation.
What did they commit to? What did you commit to? What was left unresolved? Write it now, not tomorrow.
24–48 hours later
A brief, human check-in
A short message — not a formal follow-up, just a human one. "Wanted to check in after our conversation yesterday. How are you sitting with it?" This closes the loop, signals you care about the person not just the outcome, and often surfaces things they didn’t say in the room.
"I’ve been thinking about what we talked about. I want to make sure I held up my side of it. Is there anything else you needed from me that you didn’t get to say?"
When repair is needed
If the conversation went badly
If you said something you wish you hadn’t, or the conversation escalated in a way you didn’t intend — name it. "I want to come back to what we talked about. I don’t think I handled part of it well, and I want to acknowledge that." This takes courage, but it’s what separates managers people trust from managers they tolerate.
You don’t have to recant the substance to acknowledge the delivery. "What I said was right. How I said it wasn’t. I’m sorry for that."
If you’ve had the same conversation more than twice and haven’t seen change, something in the approach may need to shift — not just the message.
First: check yourself
Is the ask specific enough to act on?
When a conversation keeps recurring, it’s worth asking whether the ask was specific enough to act on. "I need you to be more proactive" points in a direction. "I need you to flag blockers to me before they become delays" gives someone something to do. If the message was specific and clear — and they still haven’t moved — that’s useful information too.
"If I asked them right now to repeat back what I need them to do differently, would they get it right?"
Second: name the pattern
Say that this is a recurring conversation
"I want to come back to something we’ve talked about before. I’ve raised this a couple of times now, and I’m still not seeing the shift I was hoping for. I want to understand together what’s getting in the way." Naming the pattern honestly moves the conversation from feedback to problem-solving.
"This is the third time we’ve talked about this. That tells me something isn’t working in how we’re approaching it — and I want to figure out what."
Third: change the frame
If talking isn’t working, something structural needs to shift
A recurring conversation that produces no change is a signal that the conversation alone isn’t the intervention. Consider: does the role need to be redefined? Does the person need different support? Is this a motivation issue or a capability issue? If it’s capability, coaching may help. If it’s motivation, the conversation needs to get more honest about consequences.
"We’ve tried this conversation a few times. I want to be honest: if this doesn’t shift, I’ll need to start thinking about this more formally. I don’t want to get there — but I want you to know where we are."
These conversations are harder because the power dynamic is real. The principles are the same as any difficult conversation — but the stakes feel higher, and the courage it takes deserves to be named.
Before you go in
Know what you’re asking for
"I’m frustrated about X" lands differently than "I’m frustrated about X — and here’s what I think would help." Coming in with a proposed solution or a specific question — not just a problem — makes the conversation easier for everyone and more likely to go somewhere.
"I wanted to raise something and also share what I think might help — is now a good time?" is better than "I need to talk to you about a problem."
On direction or decisions you disagree with
Disagree with the decision, commit to the direction
You can push back on a decision before it’s made without undermining it after. The window for disagreement is in the discussion, not the execution. "I want to share some concerns before we go further — can I do that?" is legitimate. Quietly not following through is not.
"I’ll support this fully — but I want to make sure I’ve said out loud that I have some reservations about [X]. Can I share them briefly?"
On feedback about your manager’s behavior
Specific, private, forward-looking
Give feedback about impact, not character. "When you override my decisions in front of the team, it makes it very hard for me to lead them" is specific and actionable. "You don’t respect my leadership" is not. Keep it private, pick a calm moment, and have one thing you’re asking them to do differently.
"There’s something I’ve been wanting to raise with you. I’ve been hesitating because it feels awkward — but I think it matters enough to say. Can I share it?"
Per conversation
Conversation Notes
One record per difficult conversation — what happened, how they responded, what was agreed, and what follow-up you owe. Tracked in your Sessions. Shareable with HR if needed.