Difficult Conversations

There is almost always a conversation you have not had. With a client whose work has quietly doubled without the fee moving. With someone on the team who is not performing. With a co-director whose behaviour is affecting everyone. Sometimes with yourself, about a decision you have been circling for months.

The cost of not having them is real and it compounds. It shows up as resentment, inconsistent standards, work you have stopped enjoying and a business that is harder to run than it needs to be.

Why owners avoid them

It is rarely cowardice. It is usually some combination of not knowing how the other person will react, not wanting to damage a relationship that matters commercially, not having a 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 mindset that makes it easier

Most difficult conversations feel adversarial before they have started. The owner has already imagined the defensiveness, the conflict and the fallout, and that imagined version shapes how they approach it — tentatively, apologetically, or not at all.

The useful reframe is that you are not confronting someone. 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.

A worked example: the retainer that quietly grew

Illustrative figures. A client is on a £2,400 a month retainer, agreed on the basis of about 16 hours a month of work. Twelve months in, the logged time is averaging 27 hours.

• Charge-out rate for that work is £95 an hour. The 11 extra hours are worth £1,045 a month.
• Over a year that is £12,540 of work delivered and not billed.
• Effective rate on the account has fallen from £150 an hour to £89.
• The 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 it down. First, the conversation stops being about feelings and becomes about facts: scope changed, here is by how much, here is what we do next. Second, you can now decide what you actually want — a fee increase to £3,600, a scope reset back to 16 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.

Most owners have at least one account like this and have never done the arithmetic. Doing it is usually what makes the conversation happen.

Prepare before you speak

Know what outcome you want before you open your mouth. 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 mode and the one that requires you to have the conversation again in three months.

The structure

• Name what you have observed. Specific and factual, behaviour not 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 — making the consequence visible, because the other person usually cannot see it.
• 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.

Language that works

Stay specific and stay calm. Avoid "always" and "never" — they are almost never true 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. After you have stated the issue, stop talking. Owners fill the gap with qualifications and apologies, and dilute the whole thing in the process.

When the answer is to end it

Not every relationship should be repaired. Some clients are unprofitable at any workable price. Some behaviour will not change. Some team members are in the wrong business rather than the wrong role, and everyone involved 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 return. A clean ending protects your reputation, and people talk. A messy one costs you more than the account was worth.

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.

The checklist

• Write the facts down first. Dates, amounts, hours, specific instances. If you cannot list three, you are not ready.
• Do the arithmetic. What is this actually costing, in money or capacity, over a year?
• Decide the outcome you want before the meeting, and the minimum you will accept.
• Pick the setting. In person or on a call, never by email, never in front of others, never at the end of a long day.
• Open with the observation, not the preamble. Two sentences of context maximum.
• 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 summary within 24 hours.
• Diarise the follow-up. A conversation with no review point is a conversation you will repeat.

The questions to sit with

• Which conversation have you been putting off longest, and what has that delay cost so far?
• Out of 10, how confident are you that the other person knows there is a problem at all?
• What are you afraid will happen — and how likely is it, honestly?
• If a client or team member had been avoiding a conversation with you for six months, how would you want them to handle it?

Common questions

What if they react badly? Some will. A calm, factual, well-prepared conversation reduces the odds considerably, and a strong reaction usually tells you something useful about the relationship. What it almost never justifies is going back to saying nothing.

What if the client walks? That is a commercial risk worth pricing before you go in. If an account is unprofitable at current scope, losing it is not the worst outcome available. If it is profitable and strategically important, that shapes what you ask for — but it does not mean saying nothing.

Should I put a price increase in writing first? Send a short note flagging that you would like to review the scope, then have the conversation. Landing a number cold by email removes your ability to explain it and theirs to respond to it.

How long should I leave it after the first conversation? Agree the review date in the conversation itself — usually two to four weeks for behaviour, one billing cycle for commercial terms. Leaving it open means the next conversation starts from nothing.

Owners who handle these well are not people who enjoy confrontation. They are people who decided their standards matter more than their discomfort, and who prepared properly before they walked in.