Have the difficult conversation without losing the relationship.
Naomi assesses your calls and coaches you on the moment the message blurred or your footing slipped.
SOC 2 infrastructure Encrypted end-to-end No meeting bots Never trained on calls
After every call
Coaching, notes, follow-ups, and commitments from every call.
01Coaching
Feedback you can use on your very next call.
02Notes
The notes you meant to take, already done.
03Email drafts
The follow-up, drafted and waiting for you.
04Intelligence
A second brain for every commitment.
01Empathy & acknowledgement
Acknowledge the cost before you defend the plan.
— On the call
When the ops lead said the new strategy would double her team's workload, you jumped straight to the ROI slide. She stayed quiet for the rest of the meeting.
↓ Next time
"Name it first: 'You're right, this lands hardest on your team, and I don't want to gloss over that.' Then ask what support would make it workable."
Why it matters
People can't hear the upside until they feel heard. Acknowledging the cost turns a skeptic into a co-owner of the plan.
Before the next call
Open with the ask, then the data.
Lead with the decision, back it with one number, and move the rest to the appendix.
StructuredEmail draft
Copy notes
2027 strategy review — Partner-led growth
Oct 1, 2026 · Daniel Reyes, Elena Marsh, Ana Ortiz, Marcus Lee
Discussed
Elena's three conditions
Payback under 18 months, no new headcount in H1, and one pilot region before any national rollout.
Impact on operations
Ana flagged the partner onboarding load on her team. Daniel to scope partner-side support before launch.
Pilot in the northern region
Agreed in principle. Marcus wants a go/no-go at the November board meeting.
Your to-dos
You committed to these on the call
3 open
Send Elena the revised payback model
By Fri, Oct 9
Draft the ops support plan with Ana
Wed, Oct 7
Book the pilot kickoff with the northern team
Next week
StructuredEmail draft
Copy email✓ Copied
SubjectStrategy review next steps — pilot, payback, ops support
Hi all,
Thanks for the honest pushback today. We aligned on piloting partner-led growth in the northern region first, measured against Elena's three conditions.
Still open:
• Ops support model for Ana's team• Pilot success metric (payback vs. pipeline)
Next steps:
• Daniel: Send the revised payback model (by Fri)• Daniel: Draft the ops support plan with Ana• Marcus: Add the go/no-go to the board agenda
Talk soon, Daniel
Drafted from the call · edit before sendingReady to send
EM
Elena Marsh
CFO · Corvane
4 calls3 open asks
CommitmentDue Fri
Send the revised payback model
Promised to Elena · mentioned in 3 calls
Feedback you can use on your very next call.
The notes you meant to take, already done.
The follow-up, drafted and waiting for you.
A second brain for every commitment.
Empathy & acknowledgement
Acknowledge the cost before you defend the plan.
— On the call
When the ops lead said the strategy would double her team's workload, you jumped straight to the ROI slide.
↓ Next time
"Name it first: 'You're right, this lands hardest on your team.' Then ask what support would make it workable."
Before the next call
Open with the ask, then the data.
Lead with the decision, back it with one number.
StructuredEmail draft
2027 strategy review
Oct 1 · Daniel, Elena, Ana, Marcus
Discussed
Elena's three conditions
Payback under 18 months, no new H1 headcount, one pilot region first.
Impact on operations
Ana flagged the onboarding load on her team.
Northern pilot
Go/no-go at the November board meeting.
Your to-dos2 open
Send Elena the payback model
By Fri, Oct 9
Draft the ops plan with Ana
Wed, Oct 7
StructuredEmail draft
Copy✓ Copied
SubjectStrategy review next steps — pilot, payback, ops
Hi all,
Thanks for the honest pushback today. We aligned on piloting partner-led growth in the northern region first, measured against Elena's three conditions.
Next steps:
• Daniel: Revised payback model (Fri)• Daniel: Ops support plan with Ana• Marcus: Go/no-go on board agenda
Talk soon, Daniel
Drafted from the call · edit before sending
EM
Elena Marsh
CFO · Corvane
4 calls3 open asks
CommitmentDue Fri
Send the revised payback model
Promised to Elena · 3 calls
Use cases
Most of your work happens in conversation. Get better at it.
Did the conversation end with a clear way forward, or just tension and no plan?
Next Steps & AccountabilityAdaptabilityFiller LanguageJargon Management
15 dimensions scored on every call.
Say the hard thing without the fight.
Deliver it, then stop and let them respond.
When they push back, get curious, not louder.
Executive Presence 4710
When they pushed back, your “I feel” turned into “you always.” The conversation stopped being about the problem.
Try this on your next call
“Here’s the specific thing that isn’t working, and here’s what I need to change.”
Why it works
Under pressure the instinct is to generalize and assign blame, and the other person hears an attack instead of a problem. Staying steady in a hard conversation is mostly word choice: name the specific behavior, keep it to this one instance, and say what you need. Absolutes like “always” and “never” are where a fixable issue turns into a fight.
Relationship Building 525
You delivered the news, then filled the silence yourself. They never got to respond.
Try this on your next call
“That’s the hard part. I want to hear how it lands for you before we go further.”
Why it works
A difficult conversation is an exchange, not a delivery. When you rush to fill the silence after bad news, you protect yourself and shut them out, and they leave feeling handled instead of heard. Say the hard thing, then stop talking and let them in.
Persuasion & Influence 556
They got defensive and you matched it, point for point. Ten minutes later you were arguing about something else.
Try this on your next call
“I don’t want to argue this. Help me understand what feels off to you.”
Why it works
Defensiveness is self-protection, and meeting it head-on just raises the temperature. When they push back, get curious instead of loading your counterargument. One real question lowers the guard faster than three good points.
Your overall score
76+6 vs benchmark
Last 30 days · 18 assessed calls
7d30d90dAll
YouSenior-AE benchmark
Question depth+9
Discovery quality+6
Executive presence+4
Empathy+2
Pacing−1
Confirming next steps−9
Longitudinal intelligence
Watch your hardest conversations get easier.
Naomi tracks how you handle difficult conversations over time: whether you named the issue clearly, kept your footing when it landed, and left the other person a way forward. You see the trend, not one hard talk, so you know the next one will go better than the last.
The moment that mattered, and what to say next time.
ExampleCaught
You spent four minutes on the product before saying why now.
Try
“Let me start with why now. The market shifted last year.”
ExampleCaught
You asked three yes/no questions in a row, and the buyer never told you what’s broken.
Try
“Walk me through the last time this went wrong. What happened?”
ExampleCaught
They raised workload twice. Both times, you moved to the next agenda item.
Try
“You’ve mentioned workload twice. Let’s stay on that before we move on.”
ExampleCaught
You spent four minutes on the product before saying why now.
Try
“Let me start with why now. The market shifted last year.”
ExampleCaught
You asked three yes/no questions in a row, and the buyer never told you what’s broken.
Try
“Walk me through the last time this went wrong. What happened?”
ExampleCaught
They raised workload twice. Both times, you moved to the next agenda item.
Try
“You’ve mentioned workload twice. Let’s stay on that before we move on.”
ExampleCaught
The number that mattered came eleven minutes in, after the full timeline.
Try
“Bottom line first: we’re behind on Q3, and here’s the plan to recover.”
ExampleCaught
They said “that’s more than we budgeted.” You dropped the price before asking what the budget covered.
Try
“Help me understand what the budget was built around.”
ExampleCaught
You opened your proposal with “I might be wrong, but maybe…” and the hedge undercut a strong idea.
Try
“I’d recommend we test this with one team first.”
ExampleCaught
The number that mattered came eleven minutes in, after the full timeline.
Try
“Bottom line first: we’re behind on Q3, and here’s the plan to recover.”
ExampleCaught
They said “that’s more than we budgeted.” You dropped the price before asking what the budget covered.
Try
“Help me understand what the budget was built around.”
ExampleCaught
You opened your proposal with “I might be wrong, but maybe…” and the hedge undercut a strong idea.
Try
“I’d recommend we test this with one team first.”
ExampleCaught
You did most of the talking. Their one real complaint got thirty seconds.
Try
“Before I go further, what would make this worth it for you?”
ExampleCaught
When the CFO pushed back, your answers got longer and faster.
Try
“Fair challenge. Let me answer it with a single number.”
ExampleCaught
The call ended on “let’s circle back.” No owner, no date.
Try
“Can we hold 20 minutes Thursday to walk your team through the proposal?”
ExampleCaught
You did most of the talking. Their one real complaint got thirty seconds.
Try
“Before I go further, what would make this worth it for you?”
ExampleCaught
When the CFO pushed back, your answers got longer and faster.
Try
“Fair challenge. Let me answer it with a single number.”
ExampleCaught
The call ended on “let’s circle back.” No owner, no date.
Try
“Can we hold 20 minutes Thursday to walk your team through the proposal?”
Difficult conversation questions, answered.
How do you have a difficult conversation at work?
Name the issue plainly and early, keep it to specific behavior instead of character, make real room for the other person to respond, and end with a clear way forward. The hard part is not the script; it is staying steady while you are in it. Naomi reviews your recorded difficult conversations and scores whether you were clear, whether you stayed measured when it landed, and whether they got heard, then gives you one specific change for next time.
How do you start a difficult conversation?
Open with the actual issue, not ten minutes of cushioning that leaves them braced for worse. A sentence of warm context is fine; a paragraph of it reads as dread. Say what the conversation is about, then get specific. Naomi flags when you buried the point so deep the other person heard the worry before they heard the facts.
How do you stay calm during a difficult conversation?
Calm is mostly word choice under pressure. Drop the absolutes (“you always,” “you never”), name one specific instance instead of a pattern, and ask a question before you react to pushback. Naomi measures the language that escalates a conversation, so you can see the exact moment it turned from a problem into a fight.
How do you give difficult feedback to an employee?
Lead with the specific behavior and its impact, keep it to this instance, say what you need to change, then stop and listen. Vague, softened feedback feels kinder and helps no one, because they leave unsure what was actually wrong. Naomi scores your real feedback conversations on clarity and on whether you left space for their side.
Can you practice difficult conversations with AI?
You can rehearse an imagined one with a roleplay bot, but that is not what Naomi does. Naomi assesses the difficult conversation you actually had, on the recording, and coaches the specific moments that went sideways: where you buried the message, matched their defensiveness, or talked over the silence. Rehearsal guesses at the conversation; Naomi works from the real one.
What do you do when the other person gets defensive?
Get curious instead of matching it. Defensiveness is self-protection, and countering it point for point just raises the temperature. One genuine question (“help me understand what feels off”) lowers the guard faster than the best-argued rebuttal. Naomi catches the moments you met pushback with more push, so you can trade escalation for a question.
How do you have a difficult conversation with your boss?
Lead with the impact and the ask, stay concrete, and resist apologizing your way into it. Managers can only act on a clear request, not a hedged hint. Naomi shows you whether you actually said the thing or softened it until the point disappeared.
What is the difference between a difficult conversation and a confrontation?
The goal. A confrontation is about winning or venting; a difficult conversation is about resolving something while keeping the relationship intact. The same words can go either way depending on whether you stayed curious or went to war. Naomi measures which one your conversation actually was.
Is there a tool to help with difficult conversations?
Most “tools” are scripts, templates, or roleplay bots that rehearse a conversation you have not had yet. Naomi is different: it analyzes how you actually handled a real difficult conversation: whether you were clear, stayed steady, listened, and closed with a path, then gives you one specific thing to improve next time. It works on the conversations you are already having.
Can Naomi analyze difficult conversations on Zoom?
Yes. Naomi works with your recorded Zoom conversations: you connect Zoom, and Naomi assesses each one and returns coaching afterward. No bot sits in the meeting; the analysis happens privately on the recording, for you. It works the same for a feedback talk, a conflict, or a hard decision delivered to the team.
Does Naomi share my feedback with anyone?
No. Your coaching is private to you. It is built to make you better at the hard conversations, not to grade you for anyone else. You see your own trends and recommendations; nobody else does.
Can you get better at difficult conversations?
Yes. Handling them well is a set of repeatable habits: name the issue clearly, stay measured when it lands, listen after you deliver, and close with a path forward. What is usually missing is honest feedback, because no one is in the room to tell you how you came across. Naomi is that feedback loop, one hard conversation at a time.
Your next hard conversation could be the one that goes right.
Join the waitlist and turn every difficult conversation into coaching.