There’s a particular kind of conversation that most people will recognise at work, and those working in law particularly. 

It’s the one where you think, “I should probably speak to them about this…” and then… don’t. 

These are often labelled “difficult conversations”. 

I’m not sure that’s helpful. 

What makes them feel difficult is usually the same thing that makes them valuable. 

There’s something at stake. 

Reputation. Relationships. Future opportunities. 

And often, the person you need to speak to has more power than you do. 

The minute I label a conversation as "difficult" I create an additional mental hurdle for myself. Thinking in terms of "useful", "valuable", "necessary" or "exploratory" takes the fear-factor down a notch.  

A typical situation

Here’s a situation I’ve seen more than once. 

Someone junior is given a steer by someone more senior. They start working but the steer feels like it's taking things in the wrong direction, so they flag it: 

“I’m not sure this is the right approach.” “You’ve got what you need — just get on with it.” 

They do. The outcome isn’t great, because they weren’t set up to succeed. 

When that becomes clear, the message changes: “You should have checked.” 

Now they have two things to consider: The original issue — and the working relationship. 

This is where things become complicated. 

Life in theory and life in practice

In theory, you should be able to put your perspective without fear. In theory, the response should be fair, objective and proportionate. A lot of advice on this topic comes from that world. 

In practice, people are human. They can feel exposed. They can be defensive. They can protect their position. They can take a dislike to you because you made them feel uncomfortable or less than perfect. Your past experiences can surface in ways that no longer serve you well. 

If that person has influence over your work, your progression or your reputation saying the wrong thing can be career limiting. 

A way through the woods

I have scripted thousands of important conversations over the last thirty years. When I think about how to approach situations like this now, I don’t think in terms of scripts or phrasing. 

It’s more a short internal process guided by four questions. 

1) Is it worth raising?

This is about judgement, not being brave. 

• Is there a realistic chance this will improve something? 

• What evidence is there that this person will engage constructively? 

• What’s the cost of staying quiet? 

Sometimes the answer is: not directly. 

That doesn’t mean ignoring it. It means choosing your approach carefully. 

The best decision is not to have a conversation that you will regret.

2) What is your objective — and how important is it?

“Clear the air” isn’t an objective. 

Try: “By the end of this conversation, I want…” 

For example: 

• clarity on how to handle this next time 

• alignment on what good delegation looks like 

• a shared understanding of what happened 

Then ask: how important is this? 

If it’s a risk issue, or something that is going to cause lasting damage to your prospects, it may be worth addressing even if it’s uncomfortable. 

If you want to be happy at work, never ignore a serious issue. But make sure that it is genuinely serious. 

3) What story are you telling yourself?

If the internal narrative is: 

• “They won’t take this well”  

• “This could damage the relationship”  

• “I’m not senior enough to raise it” 

…then of course the conversation feels high-risk. 

But check whether these are facts or assumptions. Often, they are assumptions. Talking it through with someone who can offer another perspective is a good idea, so...  

4) What support can you use?

This is often the difference between reacting and responding. 

When something feels high stakes, fear and doubt can limit our thinking. 

If that’s happening, the right support is essential. 

That might be: 

• a quick sense-check with someone you trust 

• the perspective of a more senior colleague or mentor 

• HR advice if there’s a serious issue 

• practising until you feel prepared 

Whoever you turn to, pick wisely. They need to be trustworthy, competent and kind. Even one good question from someone like that can change your approach. 

A simple structure

If you do decide to raise it, a simple structure helps: 

Request → Need → Future

For example: 

“Can we revisit [the matter]? I’m unclear what you’d like me to do when I spot an issue. In future, how would you like me to handle that?” 

That doesn’t remove the risk. But it gives you the best chance of handling the situation positively and professionally. 

What to take from the situation — whatever you decide

Not every situation needs a conversation. 

But every situation has something to teach you. 

About the work. About yourself. About the person. And about the environment you’re operating in. 

You might learn: 

• how this individual responds when things go awry 

• what this situation brings out in you, and what matters to you 

• what you can rely on from this person, and what you can’t 

• what is rewarded, and what isn’t 

• where you have influence, and where you don’t 

There’s also a judgement to make about how much it matters to be “right”. 

Changing someone’s mind is not always straightforward. A well-handled conversation can strengthen a relationship. Handled badly, or at the wrong moment, it can have the opposite effect. 

Being right is not always the same as being effective. 

That doesn’t mean avoiding the issue. But it does mean being thoughtful about timing, framing, and what outcome you can realistically aim for. 

In some situations, the right step is to address it directly. In others, it’s to create clarity in other ways — making a note and sense-checking with the right people. 

If something doesn’t feel right, it’s usually worth paying attention to that signal. 

Not every issue needs escalation. But very few offer no learnings. 

Practical takeaways

For individuals

• Be deliberate about whether and how you engage. Not every issue needs to be raised, but those that carry real risk do. Make that decision consciously. 

• Get clear on your objective before you act. Know what you want to be different as a result — clarity, mutual understanding, a change to how things are working — and shape your approach around that. 

• Don’t handle something major in isolation. Sense-check your thinking, prepare your approach, and make sure you’re not carrying the risk alone where it matters. 

For firms

• Recognise that these moments are where culture is experienced. How people respond to challenge shapes relationships more than any value statement. 

• Equip supervisors for their responsibilities. Technical expertise does not automatically translate into skilled handling of people situations. These skills need to be developed. 

• Make it safe to raise concerns early in every team. Most issues are preventable if they are surfaced and handled well at the outset. That depends on how people respond when they are first raised. Most leaders understand this: the risk lies in the pockets where it isn’t the day-to-day reality. 

Final thoughts

We often think about these conversations as something to “get through”. 

In practice, they’re golden opportunities for things to get better — or at least to become clearer.