Addressing tricky topics with staff - whether it’s about their performance, conduct or compliance - is an unavoidable part of the job of a middle leader (however much you might wish that wasn’t the case).

So when it comes to talking to your team about the tough stuff, how can you ensure conversations are productive, sensitive and effective?

The lowdown
There are countless elements to bear in mind when considering how to have difficult conversations, from the practical considerations of where and when to do it (probably not in the middle of the office at lunchtime, for example), to the specifics of how you’re going to approach the process interpersonally.

Should you highlight the issue in advance so staff don’t feel blindsided? How will you ensure that they feel their side of the matter is appropriately heard?

Should you be aiming for a collaborative approach to the solution, and if so, how will you get there?

What we know about what works
If you are unsure about whether to bring up a difficult issue, it’s worth considering whether you really need to, advises Dr Helen Hughes, associate professor and director of the Behaviour Lab at Leeds University Business School.

“Difficult conversations in the workplace can range from slight annoyances to the much more serious kind, such as an allegation of some kind of malpractice,” she says.

“In these more extreme cases, it is usually fairly obvious that the difficult conversation needs to happen, and there are usually legal and HR protocols to help you manage them.

“For the less serious kind, it is important to think at the outset about what can be changed.

“If the issue is behavioural - for instance, you’d just like your colleague to do something a bit differently - this might be worth raising as there is a tangible goal or purpose to the conversation.

“However, if the issue relates to matters of personality, integrity or character, this is far more difficult to address and can be perceived as a more personal attack.”

In short, think about whether an individual formal conversation is needed for some more minor matters or whether there are more subtle ways of addressing the issue, such as a general re-emphasis of conduct or behaviour guidance, or increased role-modelling of those aspects.

If a conversation does need to be had, Hughes says it can help to remember that tolerance for difficult conversations varies from person to person.

This may determine your approach, but it should not determine whether you have the discussion at all.

“It is important to know your colleagues and think about how they are likely to respond.

“That doesn’t mean shying away from a conversation because they may take it badly. If there has been some kind of negative feedback about them, for instance, it is not always helpful in the longer term to shy away from discussing it with them.

“If the issue subsequently escalates, they are likely to feel aggrieved that they weren’t informed earlier.”

In terms of how you tackle the conversation, it is worth first considering any potential legal implications and consulting an HR or union representative, as appropriate, as “there may be protocols that stipulate what needs to be disclosed, and how formal a conversation needs to be”.

“In other cases, this is less clear cut,” she continues.

Either way, she says that giving some form of outline ahead of the meeting is crucial.

“It can help to provide a high-level overview along with your request for a conversation. If you have done that, try to schedule the meeting quickly to avoid prolonged worry.”

This doesn’t mean you schedule a meeting for half an hour after you send the email, but it does mean you should not leave someone hanging for days.

Most difficult conversations are better in person where the social cues are richer, Hughes says, but video conferencing is a reasonable alternative if needed.

And it’s important to bear in mind that your approach to the meeting will provide signals.

“If you go for an informal conversation over coffee, you shouldn’t then surprise them with a serious allegation that they were not expecting.

“But if you want to have a difficult conversation about personal style, for instance, a less formal situation can help diffuse tension, although you may run the risk of them not taking the issue as seriously as you want them to.”

Preparation for the meeting is crucial. You need to know what you want to say and have the evidence to back it up.

You also need to have clear boundaries so that the conversation doesn’t escalate, or creep into other issues and become an all-out attack or loses the message in an attempt to sugar coat it with positives.

The core aim is a change that needs to be made, so think about what you want to be changed as a result of that meeting.

“Set a goal for the conversation so the purpose is clear, and focus on behaviours rather than personal characteristics where possible.

“It can be tempting to assure complete confidentiality, but be careful that you can truly assure your colleague of this.

“It may be that you later need to report things that have been said.”

Humility is crucial. It is tempting to try to detach yourself from the conversation to enable you to be firm and because of your own discomfort, but it is important that you are genuine throughout and that you are sensitive to the person you are talking to, reacting to their signals and adapting the pace of the conversation accordingly, while ensuring the message is still getting across.

The experienced leader view

Jon Hutchinson is director of curriculum and teacher development at the Reach Foundation. He writes:

Sooner or later, you’re going to have a difficult conversation with a member of staff or a parent. It doesn’t make you a bad leader or a bad person.

But it does get easier with time. The first few will probably keep you up the night before, but eventually it will just be item four on your to-do list.

Advice on difficult conversations tends to consist of stock phrases that you can use, or some sort of checklist that you work through.

Although these can be helpful, they rarely assuage the flight of butterflies in the pit of your stomach. And that’s because they remove all of the context that actually matters.

In my experience, the “best” difficult conversations that I’ve had shared the following features:

1. I knew the person really well.
2. I knew the domain really well.
3. I practised it beforehand.

Let’s take each in turn.

First, know who it is you’re talking to. There is obviously no real shortcut to this, but if you’re familiar with someone’s values, beliefs and practice over time, it tends to be much easier to start a conversation from a place of shared understanding.

I still remember when a senior leader told me, “I know that you really care about rigour, so I’m a bit surprised that the task in your Year 4 history lesson was so easy”.

They showed that they knew what I cared about and revealed to me where my practice wasn’t in line with that. Enough said.

Second, and this is the most important thing - knowing the domain.

If you’re about to have a difficult conversation with someone in your department about a lesson observation, you need to understand the content itself.

Teasing apart exactly what the flaws were, and crucially how to address them, is simply not possible without a deep understanding of the content.

You will lean on generalities or unravel under any pushback and lose credibility. If you don’t have that understanding, wait until you do before you have the conversation.

Finally, take some time to practise the conversation with a senior leader.

We all know how much better an explanation goes in a lesson when you’ve rehearsed and refined it beforehand.

The same goes here. Whether it’s a difficult conversation with a teacher or a parent, having the opportunity to rehearse what you’re going to say with someone familiar with the situation can improve your clarity and boost your confidence going in.

You’ll also get the valuable opportunity to receive feedback on an aspect of the job that is invariably undertaken privately.