Difficult Conversations For Leaders

Difficult Conversations for Leaders

When You Know a Conversation Needs to Happen — But You’re Not Sure How to Approach It

There’s probably a conversation you know you need to have.

Someone isn’t performing at the level you need.

A colleague’s behaviour is affecting other people.

An employee keeps making the same mistake.

Someone has crossed a boundary.

You need to give feedback you know they won’t want to hear.

Or perhaps you’ve already left the conversation longer than you should have, and now you’re wondering how to raise something you’ve previously allowed to continue.

You know avoiding the conversation isn’t going to solve the problem.

You’re just not sure how to have it without making things worse.

The Australasian Leadership Institute provides practical, confidential leadership coaching for managers who need help preparing for difficult workplace conversations.

Difficult Conversations Are Difficult for a Reason

Being uncomfortable about a difficult conversation doesn’t mean you’re a poor leader.

In many cases, the opposite is true.

You may be uncomfortable because you care about the person. You don’t want to damage the relationship. You don’t want someone leaving the conversation feeling humiliated or attacked.

You may be concerned they’ll become angry, defensive or upset.

Perhaps you don’t like conflict.

Maybe you’re questioning whether you’re being fair.

Or you simply don’t know what words to use.

These are legitimate concerns.

But avoiding the conversation doesn’t make the issue disappear.

It usually gives it more time to grow.

What Happens When You Say Nothing?

Silence communicates more than leaders sometimes realise.

If poor performance isn’t addressed, the person may reasonably assume their performance is acceptable.

If inappropriate behaviour isn’t challenged, the individual may believe there isn’t a problem.

If one member of your team repeatedly misses expectations without consequences, other members of the team notice.

And if you’re frustrated about something you’ve never clearly discussed with the person involved, they may have no idea there’s an issue.

People can’t change something they don’t know needs to change.

Leadership sometimes means having the conversation you’d rather avoid.

You Don’t Need a Script. You Need a Plan.

One of the most common questions leaders ask before a difficult conversation is:

“What should I say?”

It’s an understandable question, but it’s rarely the best place to start.

Real conversations don’t follow scripts.

The other person may disagree with you. They may introduce information you didn’t know. They may become emotional. They may ask a question you weren’t expecting.

Instead of memorising the perfect words, you need to understand what you’re trying to achieve.

What is the actual issue?

What evidence do you have?

What assumptions might you be making?

What does the other person need to understand?

What needs to change?

What questions do you need to ask?

And what will you do if the conversation doesn’t go as expected?

Good preparation doesn’t guarantee an easy conversation. It gives you a much better chance of having a useful one.

Get Help Before You Have the Conversation

Sometimes the most useful thing you can do before a difficult conversation is talk it through confidentially with someone who isn’t emotionally involved in the situation.

That’s where leadership coaching can help.

You can explain what’s happening, what you’re concerned about and what you’ve tried so far.

Together, we can examine the situation, challenge assumptions, identify what needs to be addressed and work through how you want to approach the conversation.

The objective isn’t for your coach to tell you exactly what to say.

It’s to make sure that when you walk into the conversation, you know why you’re having it, what needs to be communicated and how you intend to respond if things become difficult.

What Are You Dealing With?

Every difficult conversation is different.

You may need to address poor performance.

Perhaps you need to tell someone that their behaviour is affecting the rest of the team.

You may be dealing with someone who becomes defensive whenever they receive feedback.

Perhaps you need to challenge a colleague who doesn’t report to you.

You might be managing someone who was previously your peer or friend.

Maybe you’re dealing with conflict between members of your team.

You may need to reset expectations after allowing standards to slip.

Or perhaps the difficult conversation isn’t with someone who reports to you at all.

It could be with your own manager.

Whatever the situation, the starting point is the same:

What’s happening, and what would you like to be different?

Be Clear Without Becoming Confrontational

A difficult conversation doesn’t have to become an argument.

Being direct isn’t the same as being aggressive.

One of the most important leadership skills is learning how to combine clarity with respect.

You can tell someone that their performance isn’t meeting expectations without humiliating them.

You can challenge someone’s behaviour without attacking their character.

You can disagree without becoming disrespectful.

You can listen to someone’s perspective without automatically agreeing with it.

And you can show empathy while still holding someone accountable.

Respect and accountability can exist in the same conversation.

Good leaders need both.

Talk About Behaviour, Not Personality

Consider the difference between:

“You’re disrespectful.”

and:

“When you repeatedly interrupt colleagues during meetings, people stop contributing and we’re losing perspectives that we need.”

The first statement is a judgement about the person.

The second identifies behaviour and explains its impact.

That distinction matters.

When people feel their identity is being attacked, they’re much more likely to defend themselves.

When the conversation is about observable behaviour and its consequences, there’s something specific to discuss and potentially change.

The objective isn’t to prove that someone is a problem.

It’s to address the problem.

What If They Become Defensive?

You can’t control how another person responds.

Even a well-prepared, respectful conversation may trigger defensiveness.

The person may disagree with you.

They may blame someone else.

They may become angry.

They may become upset.

They may say very little.

This is one reason difficult conversations require emotional intelligence as much as communication technique.

Your responsibility isn’t to control their emotions.

Your responsibility is to manage your own response, remain curious about what they’re telling you and keep the conversation focused on the issue that needs to be addressed.

Sometimes you will learn something that changes your perspective.

Sometimes you won’t.

Either way, you need to be able to listen without allowing the purpose of the conversation to disappear.

What If You’ve Left It Too Long?

This is extremely common.

You noticed the problem weeks or even months ago.

You didn’t address it.

Then it happened again.

You became increasingly frustrated but felt that because you hadn’t said anything previously, raising it now would be unfair.

So you waited again.

The fact that you should have addressed something earlier doesn’t mean you can’t address it now.

You may simply need to acknowledge that.

You can take responsibility for not raising the issue sooner while still making clear that something now needs to change.

Leadership isn’t about handling every situation perfectly.

Sometimes leadership means recognising that you’ve allowed something to continue and deciding that it can’t continue any longer.

Poor Performance Needs Clarity

Before assuming someone has a performance problem, ask yourself a simple question:

Have I made my expectations clear?

Managers sometimes believe they’ve communicated an expectation when they’ve actually hinted at it.

The employee thinks they’re performing adequately.

The manager thinks the employee should know they’re not.

Frustration builds on both sides.

Effective performance conversations create clarity.

What was expected?

What actually happened?

Where is the gap?

Why does that gap matter?

What needs to happen next?

And what support, if any, does the person need?

Accountability becomes much easier when expectations are clear.

The Conversation Isn’t About Winning

Difficult conversations can easily become arguments about who is right.

That’s rarely useful.

Your objective isn’t to win.

It’s to understand the situation, communicate what needs to be communicated and determine what happens next.

That means entering the conversation prepared to speak and prepared to listen.

There may be information you don’t know.

Your interpretation may not be completely accurate.

The other person may have a legitimate perspective you haven’t considered.

Good leadership requires enough confidence to address the issue and enough humility to recognise that you may not have the complete picture.

What Should Happen After the Conversation?

A difficult conversation isn’t successful simply because you managed to get through it.

Something should be clearer afterwards.

Perhaps expectations have been reset.

A behaviour needs to change.

You’ve agreed on actions.

Additional support is required.

You need to review progress at a particular time.

Or perhaps the first conversation has revealed that another conversation is necessary.

The important thing is that both people understand what happens next.

Otherwise, you may find yourself having exactly the same difficult conversation again in six months.

Leadership Coaching for Difficult Conversations

You don’t necessarily need a lengthy leadership programme because you have one difficult situation.

Sometimes you simply need somewhere to think.

The Australasian Leadership Institute offers individual leadership coaching for managers who want confidential, practical support with real leadership challenges.

A coaching session can help you:

Clarify the real issue before the conversation.

Separate facts from assumptions.

Think through the other person’s likely perspective.

Identify what you need to communicate.

Prepare for different responses.

Consider questions that may help move the conversation forward.

Manage your own emotions.

Determine what a successful outcome would look like.

And leave with a clear approach for what you’re going to do next.

The conversation remains yours to have.

The coaching helps you prepare to have it well.

Leadership Advice When You Need It

Leadership challenges don’t conveniently appear according to a training calendar.

Sometimes something happens on Tuesday and you need to deal with it on Wednesday.

That’s one of the reasons individual leadership coaching can be so valuable.

You have somewhere confidential to take the situations you can’t necessarily discuss openly with your team.

Sometimes that will involve a difficult employee.

Sometimes your manager.

Sometimes a colleague.

And sometimes the person whose approach needs challenging is you.

The purpose of coaching isn’t simply to confirm that you’re right.

A good coach should challenge your thinking, offer another perspective and help you make a better leadership decision.

Why Work With Mark Wager?

Mark Wager is the Chief Leadership Coach at the Australasian Leadership Institute and has more than three decades of leadership experience.

He has worked with leaders from organisations including the New Zealand Defence Force, Ministry of Justice, Department of Internal Affairs, ACC, Fisher & Paykel, St John, Red Cross, Barnardos, Weta Workshop, UNICEF and Amnesty International.

His approach to coaching is:

Practical. Evidence-based. Personal. Confidential.

The focus isn’t on discussing leadership in the abstract.

It’s on helping you become more effective at dealing with the leadership situations you’re facing right now.

You Don’t Have to Work It Out Alone

If there’s a difficult conversation you’re currently avoiding, ask yourself:

What am I hoping will happen if I say nothing?

Sometimes waiting is appropriate.

Sometimes you need more information.

But if you’re simply waiting because you don’t know how to approach the conversation, waiting is unlikely to make it easier.

You don’t have to work out your approach alone.

Tell us what’s happening.

Tell us what you’re worried about.

Tell us what you would like to be different.

We’ll start there.

Get Help With a Difficult Conversation

The Australasian Leadership Institute

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