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Episode 31 - Difficult Conversations

 Why are difficult conversations so difficult, even when you know what you need to say?

Perhaps you've prepared for a conversation with a member of your team, only to find yourself softening the message at the last minute.

Perhaps you've spent ages thinking about what you want to say, but when the opportunity comes, you don't quite say it.

Or perhaps you've been putting off a conversation because you're worried about how the other person might react.

If any of that sounds familiar, you're certainly not alone.

This week's episode of Management Matters was inspired by a coaching conversation about exactly this problem.

And I think there's much more going on here than the usual advice to "feel the fear and do it anyway" would suggest.

Why difficult conversations feel risky

When you're approaching a difficult conversation, there's often a psychological risk involved.

You might be worried about disappointing someone, upsetting them, being judged, creating conflict or damaging a working relationship.

And if you're a thoughtful, compassionate manager, you may be particularly conscious of what the other person is already dealing with.

That matters, especially in the current Higher Education environment, where financial pressures, restructures, changing expectations and uncertainty are affecting so many teams.

But there's something else we need to consider alongside the personal discomfort of having the conversation.

Balancing compassion with accountability

As a manager or leader, you're responsible for more than the individual conversation.

You also have responsibilities to your wider team, your service and the people who rely on that service.

If an issue isn't addressed, what happens next?

Could it affect colleagues, service delivery, student experience or the team's ability to do its work?

Sometimes we focus so much on the potential discomfort of saying something difficult that we overlook the consequences of not saying it.

And while kindness and compassion are important values, they can sometimes lead us towards holding back information or avoiding a message that someone genuinely needs to hear.

This connects with Episode 30: How to Find Your Leadership Style, where I explored how our values influence the way we manage and lead, including what happens when those values become overexpressed.

You don't have to manage everyone in exactly the same way

Another important part of this is situational flexibility.

Think about two people doing similar jobs.

One might be brand new, still learning the institution, understanding the team's processes and finding their feet.

The other might have been in the role for years and be highly experienced.

Your approach to managing those two people will naturally be different.

The same principle applies to difficult conversations.

You need to consider the individual, the context, the expectations and the risks involved, rather than relying on one standard approach to every situation.

Preparation and rehearsal make a difference

Once you've understood the situation, there are two practical things I think can make a real difference.

The first is preparation.

Not lying awake at three in the morning rehearsing the first two sentences over and over.

I mean getting clear about what kind of conversation you need to have, what actually needs to be said and what might happen if the issue isn't addressed.

The second is rehearsal.

I'm a big fan of mental rehearsal, but not simply imagining yourself delivering the opening line.

I mean rehearsing the whole experience, including how the other person might respond, how you want to respond, how you'll close the conversation and what happens afterwards.

The aim is to help you move beyond knowing what you should do and towards actually doing it.

Introducing the Brave Management Conversation Starter Pack

I've created a new resource to help you with exactly this.

The Brave Management Conversation Starter Pack includes:

  • A fillable PDF worksheet to help you prepare for the conversation, identify what needs to be said and think through the situation.

  • A guided audio visualisation to help you mentally rehearse the conversation, including the difficult moments, your response and the follow-up.

It's available in my new Tool Shed, which is a collection of practical resources for specific management and leadership challenges.

Everything in the Tool Shed is either free or pay what you like. You can choose to pay for a resource if you'd like to, or access it for free.

Get the Brave Management Conversation Starter Pack

Explore the Tool Shed

Moving the conversation forward

You don't necessarily need more information about how to manage people.

Sometimes you already know what needs to happen, but you need a better way to prepare yourself to follow through.

And that's what I want this episode, and the new starter pack, to help you with.

Because having a difficult conversation isn't just about getting through an uncomfortable moment.

It's about being able to move a situation forward in a way that takes care of you, the other person, your wider responsibilities and the kind of manager or leader you want to be.

If you give the starter pack a try, I'd love to hear how you get on.

And if there are other management challenges you'd like me to create practical tools for, do let me know.

You can email me at [email protected].