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 genuine 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.
There is almost always a conversation you have not had. With a client whose work has quietly doubled while the fee stayed still. With someone on the team who is not performing. With a co-director whose behaviour is affecting everyone. The cost of not having it is real and it compounds: resentment, inconsistent standards, work you no longer enjoy and a business that is harder to run than it needs to be. This guide is how to have it properly.
Why do owners avoid these conversations?
Rarely cowardice. Usually some mixture of not knowing how the other person will react, not wanting to damage a relationship that matters commercially, having no structure to follow, and a reasonable hope that it might sort itself out.
Occasionally it does. Far more often the delay makes it harder, because by the time you raise it you are also implicitly explaining why you did not raise it six months ago. The useful reframe is that you are not confronting anybody. You are naming something that is not working and opening a conversation about what to do about it. That is information-sharing and problem-solving, and it changes both your tone and the odds of a decent outcome.
What is the situation actually costing you?
Do the arithmetic before you do anything else. It changes what you ask for, and it changes how calmly you can ask.
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.
Two things fall out of writing that down. The conversation stops being about feelings and becomes about facts: scope changed, here is by how much, here is what we do next. And you can now decide what you actually want — a fee increase, a scope reset back to the original hours, or a considered decision to keep absorbing it because the account leads somewhere. All three are legitimate. Drifting into the third by default is not.
What do you decide before you open your mouth?
Know the outcome you want and the minimum you will accept. A correction, an agreement, a payment, a change in behaviour, or an ending. Clarity of purpose is what stops you softening the message until it means nothing, which is the most common failure and the one that makes you repeat the whole conversation in three months.
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. Specific, factual, 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. What it costs the business, the team or the client. Not blame — the consequence is usually invisible from where the other person is standing.
- Ask a genuine question. "What is happening from your side?" You may be missing context. Even when you are not, it turns a lecture into a conversation.
- 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 protects everyone, creates clarity and signals that you are serious, which by itself changes behaviour more often than owners expect.
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".
Silence is a tool. Once you have stated the issue, stop talking. Owners fill the gap with qualifications and apologies and dilute the whole thing in the process. The Feel, Felt, Found model is a useful way to acknowledge a reaction without retreating from the point, and Backbone and Heart is the balance you are aiming for: warm about the person, firm about the standard. If saying no is the harder part for you, our post on the art of saying no covers that side.
What if the answer is to end the relationship?
Not every relationship should be repaired. Some clients are unprofitable at any workable price. Some behaviour will not change. Some people are in the wrong business rather than the wrong role, and everyone involved usually knows it.
Ending it well matters commercially. Give proper notice, help with the handover, be straightforward about why, and resist the temptation to soften it into something ambiguous that leaves them expecting to come back. A clean ending protects your reputation, and people talk. Before you get there, be honest about whether you are ending a relationship or avoiding a conversation — walking away from a fixable problem is expensive, and it tends to become a habit. This is the ground leadership coaching spends most of its time on.
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, not the preamble. Two sentences of context at most.
- Ask, then listen properly. Do not prepare your response while they are talking.
- Agree specifics and a date. Vague agreement is the same as no agreement.
- Send the written summary within 24 hours.
- Diarise the follow-up. A conversation with no review point is a conversation you will be having again.
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Frequently asked questions
What if they react badly?
Some will, and that is worth expecting rather than fearing. A calm, factual, well-prepared conversation reduces the odds considerably, because most strong reactions 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. A strong reaction usually tells you something useful about the relationship and about how much was being left unsaid on both sides. What it almost never justifies is going back to saying nothing, because the underlying problem has not moved.
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. In practice, clients who are getting good work rarely leave over a properly explained scope conversation. The ones who do were usually going to become a problem in some other way before long.
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, usually badly. Have the conversation, agree the principle, then confirm the specifics in writing the same day. If the relationship is genuinely 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, two to four weeks is usually right: 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. Recognising it is what makes the standard stick.
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. Said once it builds credibility. Repeated, it becomes an apology that quietly withdraws the request you came to make. What your share of the fault does change is the ask. Billing retrospectively for work you accepted without complaint is a fight you will usually lose 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. Owners often think their own part in the drift disqualifies them from raising it. It does not. It just moves the conversation from what happened to how this works from now on.