A difficult conversation goes well when it is prepared rather than improvised. The structure is five steps: name what you have observed in factual terms, state the impact it is having, ask a question and listen to the answer, agree specifically what changes and by when, then confirm it in writing the same day. Before any of that, do the arithmetic — work out what the situation is costing over a year — because facts are what stop the conversation becoming about feelings.
The conversation might be with a client whose work has doubled while the fee stayed still, someone on the team who is not performing, or a co-director whose behaviour is affecting everyone. Putting it off brings resentment, inconsistent standards and a business that is harder to run.
Why do owners avoid these conversations?
Owners avoid them because they do not know how the other person will react, do not want to damage a relationship that matters commercially, have no structure to follow, or hope it might sort itself out.
Delay tends to make it harder, because by the time you raise it you are also explaining why you did not raise it six months ago. Treat it as naming something that is not working and agreeing what to do about it.
What is the situation costing you?
Do the arithmetic first, because it changes what you ask for.
An invented illustration of the shape — not a client, and not a claimed result. A client is on a £2,400 a month retainer agreed on the basis of about 16 hours of work a month. Twelve months in, logged time is averaging 27 hours. At a £95 charge-out rate the 11 extra hours are worth £1,045 a month, so £12,540 of work has been delivered and not billed over the year. The effective rate on the account has fallen from £150 an hour to £89. Those 11 hours a month are also unavailable for anything else — roughly 132 hours a year, or most of a month of delivery capacity.
Writing that down makes the conversation about facts: scope changed, here is by how much, here is what we do next. It also lets you decide what you want: a fee increase, a scope reset back to the original hours, or a deliberate decision to keep absorbing it because the account leads somewhere.
What should you decide beforehand?
Know the outcome you want, such as a correction, an agreement, a payment, a change in behaviour or an ending, and the minimum you will accept. That stops you softening the message until it means nothing.
Then pick the setting deliberately: in person or on a call, never by email, never in front of other people, and never at the end of a long day when both of you are tired.
What is the structure?
- Name what you have observed. Be specific and factual, and describe behaviour rather than character. "The last three updates arrived after the agreed date" rather than "you are disorganised". "We have logged 27 hours a month against a 16-hour scope" rather than "I feel taken advantage of".
- State the impact. Say what it costs the business, the team or the client, because the other person may not see the consequence.
- Ask a question. "What is happening from your side?" You may be missing context.
- Agree what changes. What is different, by when, what support is available, and what happens if it does not change.
- Confirm in writing. A short factual email the same day. It records what was agreed.
Which words help, and which start arguments?
Stay specific and stay calm. Avoid "always" and "never" — they are almost never accurate and they invite an argument about the exception rather than the issue. Say what you need rather than what they have done wrong: "I would like to agree a way forward on the scope" lands considerably better than "this needs sorting out".
Once you have stated the issue, stop talking, rather than filling the gap with qualifications and apologies.
What if the answer is to end the relationship?
Some clients are unprofitable at any workable price, some behaviour will not change, and some people are in the wrong business rather than the wrong role.
Give proper notice, help with the handover, be clear about why, and do not soften it into something ambiguous. Before you get there, check whether you are ending a relationship or avoiding a conversation. Leadership coaching spends much of its time on this.
How do you make it stick?
- Write the facts down first: dates, amounts, hours, specific instances. If you cannot list three, you are not ready.
- Decide the outcome you want, and the minimum you will accept, before the meeting.
- Open with the observation. Two sentences of context at most.
- Ask, then listen properly. Do not prepare your response while they are talking.
- Agree specifics and a date.
- Send the written summary within 24 hours.
- Diarise the follow-up.
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Frequently asked questions
What if they react badly?
Some will. A calm, factual, well-prepared conversation reduces the odds considerably, because strong reactions often come from feeling ambushed or judged rather than from the content itself. If it does happen, do not match the temperature. Acknowledge the reaction, restate the observation in the same words you used the first time, and offer to continue the conversation the following day if that would help. The underlying problem is still there, so do not go back to saying nothing. Write down what was said once the meeting ends.
What if the client walks away?
Price that risk before you go in, because it changes what you ask for. If the account is unprofitable at its current scope, losing it is not the worst outcome available and the capacity it frees has a value you can calculate. If it is profitable and strategically important, that shapes how you open and what you are willing to accept, but it does not mean saying nothing and absorbing the drift indefinitely. Write down the lowest outcome you will accept before the meeting, and the date you would end the arrangement if it is not met.
Should I put a price increase in writing first?
Send a short note saying you would like to review the scope and arrange a time, then have the conversation live. Landing a number cold by email removes your ability to explain the reasoning and theirs to respond to it, and it turns a discussion into an ultimatum they will answer in writing. Have the conversation, agree the principle, then confirm the specifics in writing the same day. If the relationship is remote and email is the only realistic channel, keep it factual, show the arithmetic that led to the number, and offer a call. Never lead with the number alone.
How long should I leave it before following up?
Agree the review date inside the conversation itself rather than deciding afterwards. For behaviour, allow two to four weeks: long enough to show a change, short enough that drifting back gets noticed. For commercial terms, one billing cycle. Put it in the diary before you leave the room and say that you are doing so, because a review point is what turns an agreement into a commitment. Leaving it open means the next conversation starts from nothing and you carry the whole history again. If the change has happened, say so at the review.
What if I am partly at fault, because I let the scope drift for a year without saying anything?
Own it once, briefly, and then move on to the facts. One sentence is enough: we should have raised this at six months, we did not, and that is on us. Do not repeat it. What your share of the fault does change is the ask. Billing retrospectively for work you accepted without complaint is hard to win and it damages the relationship, so set the new terms from a defined future date instead, normally the next renewal or the start of the next month. Your part in the drift does not stop you raising it; it moves the conversation to how things work from now on.