Free · 6 minutes · 15 situations

Am I ready for a difficult conversation?

You know you need to have it. You’ve put it off for two weeks and it’s getting worse. Find out which part of the conversation you get wrong.

Difficult Conversation Readiness Assessment

15 everyday conversations from a supervisor’s or manager’s week.

Pick what you’d actually say or do. About six minutes.

  • A score out of 10 for each of the five parts of a hard conversation
  • Next steps and a line to say from our AI coach (your first one free)
  • The part you avoid, and a Practice Room conversation to try it in

For the conversation you’re putting off. Lateness? A meets expectations review? A complaint about a colleague? A no to a holiday request? A standard that’s slipped?

A self-assessment for reflection, not a formal qualification check, a hiring tool or HR advice.

The conversation you keep putting off

You know you need to have it. Someone’s late again, a review is lower than they’ll expect, a colleague has complained about a colleague, or you have to say no to a holiday. You’ve rehearsed it in the car. You’ve put it off for two weeks, and it’s getting worse, because the team has noticed you haven’t had it.

Nobody is taught this part of the job. CMI research found that 82% of people who enter management have had no formal management and leadership training, and the hard conversation is the part they feel least ready for. Most people don’t get the whole conversation wrong. They get one part of it wrong, every time, and never find out which.

It takes about six minutes: 15 everyday conversations from a supervisor’s or manager’s week, four honest answers each. You get a score for each of the five parts below, the part you avoid, and the Practice Room conversation that matches it.

Written by Nelson Fernandes, CMI Level 5 in Management and Leadership.

The five parts of a difficult conversation with an employee

Every hard conversation has the same shape, whether it’s about lateness, a slipped standard or a no. The five areas follow that shape. This is a self-assessment, not a mapping to a professional standard.

Preparing
Knowing what you saw, why it matters and what you’re asking for, before you walk in.
Opening
The first line: in private, soon, and about the thing you saw.
Listening
Hearing what’s behind the pushback or the silence before you answer it.
Holding your line
Staying with the point when they push back, go quiet, cry or get angry, without hardening.
Agreeing the next step
Leaving with one change agreed, who does it, and a date to check.

Most people are fine at two or three of these. The gap is usually the opening, because that’s the part you can put off, or the next step, because by then you’re relieved it’s over.

Signs you’re ready for difficult conversations at work, and signs you’re not yet

Ready

  • You can say what you saw, with dates, in two sentences.
  • You ask for five minutes in private, the same day or the next.
  • When they push back, you ask a question before you answer.
  • You leave with one thing agreed and a date to look at it again.

Not yet

  • You’ve told the whole team something that was really for one person.
  • You’ve sent a message instead of having the conversation.
  • A good reason, tears or a raised voice makes the point disappear.
  • The conversation ends on a nod and happens again in a month.

None of the “not yet” signs means you can’t have the conversation. They’re the list of what to practise first.

Using your result: pick the Practice Room conversation that matches

Your headline names the part of the conversation you get wrong most often. That’s the one to practise before Thursday, not all five.

  • Preparing is your gap. Try the performance talk you’ve been avoiding. Write your three lines first, then see if they survive the character’s first reply.
  • Opening is your gap. Try the team member who used to be your mate. The first sentence is the whole exercise.
  • Listening is your gap. Try the one-to-one where everything is fine every week. Your job is to ask, then wait.
  • Holding your line is your gap. Try the meets expectations review. Decide your one sentence before you start, and see how many times you need it.
  • Agreeing the next step is your gap. Try setting goals with someone who doesn’t want any. Don’t end it until something is agreed and dated.

Each Practice Room conversation puts you in front of an AI character who answers the way people do, and gives you feedback on what you said and what to say instead. Your first go at each conversation is free. If the conversation you’re facing sounds like bullying, harassment, discrimination, a health matter or a grievance, it isn’t one to practise. It’s one to take to your manager or HR, with the person who told you.

Your result also gives you one thing to try before the conversation, and two things to read for the part you’re working on. If you’re interviewing for a step up, “Tell me about a difficult conversation you handled” is a question you’ll get. Your result gives you an honest answer: the part you’re good at, with an example, and the part you’re working on.

Questions people ask

Is the assessment free?

Yes. Your scores are free every time, with nothing to pay and no email or sign-up needed to see your result. You also get one free personal read from our AI coach, on whichever assessment you do first. After that, each new read uses one credit (packs from 10 for £3 to 100 for £20), and one code works for your whole team.

How long does it take?

About six minutes. There are 15 conversations, one per screen, and you can go back and change an answer before you move on.

Is this mapped to a standard or qualification?

No. It’s a self-assessment for reflection. The five areas follow the shape of a hard conversation, not a published standard, and it isn’t a hiring tool or HR advice.

What happens to my answers?

Nothing you answer is stored. Your answers are scored in one go and dropped, and your scores live only in the page’s web address. To write your personal read, our AI coach gets your five scores and the habit behind each answer (for example "softening the message"), never the answer text, and it does not keep them. To know you’ve had your free read without an account, your browser keeps a random number (no name, no email), and we keep a scrambled marker of it and your connection for a year.

What do Strong, Good, Mixed and Gap mean?

Each area is scored out of 10. Strong is 8 to 10, Good is 6 to 7, Mixed is 4 to 5 and Gap is 0 to 3. Your headline names the lowest area, because that is the part of the conversation to work on first.

What if my conversation is an HR matter?

Then this isn’t the tool for it. If what you’ve been told sounds like bullying, harassment, discrimination, a health matter or a grievance, the right move is to know it’s one and take it to your manager or HR, with the person who told you. The assessment includes that moment, because knowing when a conversation isn’t yours to have is part of being ready.

I’ve already had the conversation and it went badly. Is this for me?

Yes. Most conversations that go badly go wrong at one of the five parts, not all of them. Your result names the part, and the Practice Room has a conversation you can try again with an AI character before the real follow-up.

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