You need to challenge a colleague without damaging the relationship
Something needs saying to a colleague, and what is delaying it is the thought of what saying it will cost the working relationship.
There is a specific thing a colleague is doing, or not doing, that needs to change. You are not in doubt about the facts and you have been meaning to raise it for a while. What keeps stopping you is the relationship: they are a good colleague, or a friend, or somebody whose goodwill you rely on elsewhere, and you are weighing the cost of saying it against the cost of leaving it.
Presenting symptoms
- You have rehearsed the conversation more than once and not had it.
- You have raised it obliquely, in a joke or a general remark to a group, hoping it would land.
- Other people have begun to notice the thing you have not said anything about.
Possible causes
- You may not yet be clear what specifically needs to be different, only that something does.
- You may not know why they are doing it, and suspect there is a reason you have not heard.
- The relationship may carry something that makes it hard: they are a friend, they were your peer, or you rely on their goodwill elsewhere.
- You may be unsure whether this is a conversation or the beginning of something formal, and unsure which one you are allowed to have.
You are clear that something is wrong and not clear what right would look like.
Your most useful next step: Write one sentence naming the specific thing, and one naming what you need instead, with a date attached. Do not book the conversation until the second sentence exists; if it will not come, drafting it is this week’s work and the conversation can wait a week.
Lead behaviours
You do not know why they are doing it, and suspect there is a reason.
Your most useful next step: Book twenty minutes and spend the first half asking how they see it and what is making it difficult, before you say anything about what has to change. Go in prepared to find that what you ask for afterwards is not what you planned to ask for.
Lead behaviours
The relationship is what is stopping you.
Your most useful next step: Name the awkwardness at the start rather than working around it: that you value working with them, that this is uncomfortable, and that leaving it unsaid would cost more. Then reach the specific issue within the first few minutes rather than at the end.
Lead behaviours
You are unsure whether this is a conversation or the start of something formal.
Your most useful next step: Establish before you speak whether anything formal applies, by asking whoever advises your school or trust on these matters. Then tell the colleague at the outset which kind of conversation this is. A colleague who later discovers it was formal, or who wrongly believes it was, will remember that rather than anything else you said.
Lead behaviours
Core behaviours
Expressing concern and creating accountability are different acts, and only the second changes anything. A leader can voice worry sincerely, and more than once, without ever asking for a specific change by an agreed date. That omission, rather than any lack of courage, is what leaves most of these situations where they are.
Avoiding a necessary conversation is not neutral. Trust erodes quietly while the leader waits, and colleagues notice what goes unmentioned as readily as what is said. A challenge that is direct, fair and respectfully handled can leave the working relationship in better condition than it was, and how it is handled is the leader’s responsibility rather than a matter of luck.
You are going in with a theory about why this is happening, and it may be wrong. Asking before telling costs ten minutes and occasionally changes the entire conversation, which is a good return on ten minutes.
A request that arrives without its reason is heard as a preference, and preferences get weighed against the colleague’s own. Saying what the change is for is what makes it a professional matter rather than a personal one.
Your own discomfort is the variable you control. A leader who is tense delivers the message harder and faster than intended; one who is apologetic delivers it so softly that it is not heard as a request at all.
Secondary behaviours
Use this before you speak, in two ways: establish that what you believe is happening is actually happening, and establish whether anything formal applies. Both are far easier to check beforehand than to correct afterwards.
Use this where you suspect something else is going on. What you know about this colleague should shape how you open the conversation, though it should not change whether you have it.
Use this to close. A challenge conversation that ends in shared understanding and no named change produces relief on both sides and nothing else, and it is much harder to raise the same thing a second time.
Use this on the how rather than on the what. The change itself is not negotiable once you have decided it is needed, but the way it is achieved usually is, and a colleague who designs that part is considerably more likely to deliver it.
A useful first action
Write two sentences: the specific thing that is happening, and what you need instead, with a date. If the second sentence will not come, that is why the conversation has not happened yet, and writing it is the whole of this week’s task.
Suggested approach
- Write down the specific thing and what you need instead, with a date. Do not book the conversation until both sentences exist.
- Check that what you believe is happening is actually happening, and whether anything formal applies, before you speak.
- Open by asking how they see it, and leave room for an answer that changes what you go on to ask for.
- Name the change and its purpose plainly within the first few minutes, rather than arriving at it at the end.
- Agree with them how the change will be achieved, put a date on it, and say when you will next talk about it.