AI Communication Coach

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.

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.

Use cases

Most of your work happens in conversation. Get better at it.

How it works

You have the hard talk. Naomi handles the rest.

Coaching, notes, the follow-up, and your commitments, waiting for you minutes after you hang up.

In the background

2:00 PM · Call ends
Connect

Nothing joins your call.

Sync Zoom, Granola, or Google Meet, or paste a transcript. No bots, no “recording has started.”

2:01 PM
Analyze

Scored on 15 dimensions.

Not sentiment, not keywords. Every call is assessed against a research-backed model across four skill clusters.

What comes back

2:14 PM
Coach

Your review, texted to you.

The one moment that mattered and the exact words to try next, while the call is still fresh.

2:14 PM
Notes

Decisions and to-dos, captured.

What was decided, what’s still open, and every to-do you agreed to.

2:14 PM
Follow-up

A recap email, drafted for you.

A recap email drafted from the call, with owners and next steps. Edit, copy, done.

Every call after
Remember

People and promises, linked across calls.

People, companies, and commitments, linked across all your calls. Nothing you promised gets lost.

Communication Coaching

What Naomi assesses in your difficult conversations.

Professional Discipline

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.

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.

Your overall score
76+6 vs benchmark
Last 30 days · 18 assessed calls
7d30d90dAll
100806040Benchmark · 7082Apr 1Apr 8Apr 15Apr 22Apr 29Today
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.

Built for every role

Built for everyone who has to have the hard talk.

Join waitlist
Coaching moments

The moment that mattered, and what to say next time.

ExampleCaught

You spent four minutes on the product before saying why now.

Naomi
Try

“Let me start with why now. The market shifted last year.”

Founder · Investor pitchStructure
ExampleCaught

You asked three yes/no questions in a row, and the buyer never told you what’s broken.

Naomi
Try

“Walk me through the last time this went wrong. What happened?”

Sales · Discovery callQuestioning quality
ExampleCaught

They raised workload twice. Both times, you moved to the next agenda item.

Naomi
Try

“You’ve mentioned workload twice. Let’s stay on that before we move on.”

Manager · 1:1Active listening
ExampleCaught

The number that mattered came eleven minutes in, after the full timeline.

Naomi
Try

“Bottom line first: we’re behind on Q3, and here’s the plan to recover.”

Senior operator · Board updateConciseness
ExampleCaught

They said “that’s more than we budgeted.” You dropped the price before asking what the budget covered.

Naomi
Try

“Help me understand what the budget was built around.”

Sales · Pricing callObjection handling
ExampleCaught

You opened your proposal with “I might be wrong, but maybe…” and the hedge undercut a strong idea.

Naomi
Try

“I’d recommend we test this with one team first.”

Early career · Team meetingFiller language
ExampleCaught

You did most of the talking. Their one real complaint got thirty seconds.

Naomi
Try

“Before I go further, what would make this worth it for you?”

Founder · Customer callConversation balance
ExampleCaught

When the CFO pushed back, your answers got longer and faster.

Naomi
Try

“Fair challenge. Let me answer it with a single number.”

Senior operator · Exec readoutEmotional regulation
ExampleCaught

The call ended on “let’s circle back.” No owner, no date.

Naomi
Try

“Can we hold 20 minutes Thursday to walk your team through the proposal?”

Sales · Follow-up callNext steps

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.