The 5 Hard Conversations Every Leader Must Have (And How to Nail Them!)

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I’ll never forget almost a decade ago when I had one of my first hard conversations as a leader.

I had to meet with one of my team members to talk about issues with their performance.

The worst part was that I really liked this person.

I had all these worst-case scenarios running through my head.

I was so anxious leading up to the meeting.

I couldn’t sleep the night before.

No one taught me how to have difficult conversations like this.

I had no idea what to say or how to say it.

I felt like I was just winging it.

In the early days of my leadership, I definitely made all the mistakes you can imagine.

But since then, I've had quite literally hundreds of really hard conversations.

And not just performance issues.

I’m talking about pretty much everything under the sun.

We’ll get into all of that in a minute because there are a lot of different kinds of conversations that are hard for different reasons.

Here’s the ultimate reality.

Every leader faces hard conversations that can make or break their team.

And quite frankly, if you don’t know what you’re doing, you can really screw things up and make a big mess.

But with the right principles and strategies, you can actually turn hard conversations into positive experiences that lead to a healthier culture and a stronger, faster-growing team.

By the end of this episode, you should have a rock-solid strategy to take on pretty much any hard conversation with confidence.

Here’s how we’re going to approach this.

First, I’m going to address five of the most common hard conversations you'll have in leadership roles.

Then I’m going to share five principles to help you navigate them.

Sound good?

Okay, let’s begin by looking at the five different conversations we need to prepare for.

CONVERSATION 1: CONFLICT

I know… We can all collectively groan.

But you know, the reality of leadership is that you have to deal with a lot of conflict.

If there are people involved, you can bet there will be conflict.

Feelings get hurt, frustrations can boil, and you can have different opinions on matters that can lead to conflict.

As the leader, you get to deal with all of it!

Here’s the second type of conversation you need to have.

CONVERSATION 2: PERFORMANCE ISSUES

It could be showing up late, missed deadlines, poor productivity, poor quality work, a bad attitude, policy violations, the list is endless.

When a team member is having work performance issues, you’re the one who has to sit down with them and get them back on track.

This is especially hard for non-confrontational type people.

It can be intimidating to deliver corrective feedback to team members.

CONVERSATION 3: FIRING

Ugh… Yes, the dreaded conversation.

Whether it’s mass layoffs or personal 1-on-1 layoffs, it all sucks.

I had a buddy recently who was told he had to lay off an entire department, and he was just a shell of himself.

How do you look someone in the eyes and fire them?

What if they have a family they’re supporting?

What if they’re a friend?

Do you know how to have that conversation?

CONVERSATION 4: TRAGEDY AND TRIALS

Over the years, I’ve had to show up for people who experience debilitating injuries, a cancer diagnosis, chronic depression and anxiety, people who have lost a loved one, parents who have a miscarriage…

Tragedies strike all the time.

It’s heartbreaking.

Are you prepared to handle that?

Do you know how to have those kinds of conversations?

A leader should know how to walk through that with people.

Here’s the last one.

CONVERSATION 5: CHANGE

This can be a really hard one for leaders to navigate.

Change can be good.

But oftentimes, change sparks fear, resentment, frustration, and stress in people.

What if your company gets bought out, and you know everyone is worrying about their job security?

What if the market is changing and you know it’s going to create a lot of stress on your team as you adapt?

What if someone’s role has to change, and you know they won’t like it?

Do you know how to have that kind of conversation?

Well, if I just raised your blood pressure a bit, you’re in the right place!

I know… These are really difficult conversations to have, but the principles we’ll look at next can help you navigate them.

Focusing on principles, in my opinion, is more powerful than focusing on practices.

As you know, every conversation is a little bit different.

You’re dealing with different situations, different problems, and different personalities.

The context is always changing and always unique.

These five principles are pretty much all you need to have every single type of conversation with confidence and success.

So, let’s turn to those now.

Here’s the first one.

PRINCIPLE 1: ASK AND LISTEN

This is such a simple yet powerful principle in hard conversations of all kinds.

First, knowing what to say in these conversations is often one of the biggest stress points for people.

The truth is, you shouldn’t be saying a lot of things; you just need to say the right things.

So…

Start with questions, shut up, and just listen.

And I mean REALLY listen.

Don’t formulate your response just yet, don’t interrupt, or get distracted.

Be an engaged listener.

Take in the information, the emotion, and the body language.

If there is a pause in the conversation, ask another question to encourage them to keep sharing as much as they can.

By letting them talk while you listen, you can gain a better understanding of the whole context.

This helps you avoid speaking out of ignorance, but it also does another important thing: It makes the person feel seen, heard, and understood.

That’s huge.

Hard conversations don’t go well if people feel misunderstood.

That’s why this is such an important principle for navigating hard conversations.

Okay, here’s principle number two.

PRINCIPLE 2: SHOW EMPATHY

Once you’ve listened thoroughly and developed an understanding of things, you have a great opportunity to show empathy.

This is critical.

I’m going to be 100% transparent that this is the hardest principle for me personally.

I have to work really hard at showing empathy because I’m not a naturally empathetic person.

I’m more of a “suck it up and move on” kind of person.

But you know, that’s just not how you handle most hard conversations.

99.9% of the time, you’ve got to show a certain degree of empathy.

And let’s be clear about what empathy really is, because a lot of people confuse it with sympathy.

There’s a difference.

The real meaning of empathy is the ability to understand, share, and feel another person's emotions and perspective by "stepping into their shoes."

If listening is the key to making people feel seen and understood, empathy is the key to making them feel connected to you.

To be clear, empathy has to go beyond merely recognizing feelings.

It’s about validating them.

It’s about fostering a supportive response.

Now, I’ve noticed this is intuitive to some people, and to others (like me), it can be really foreign and challenging.

In any case, you’ve got to show empathy.

Hard conversations aren’t quite as hard if you establish a strong connection.

Here’s the third principle.

PRINCIPLE 3: BE HONEST AND CLEAR

At this point, you’ve listened, and you’ve responded with empathy.

Now it’s time for some honesty.

This is where you’re really getting into what's making the conversation so difficult.

This is where you talk through the conflict, you communicate they’re being let go, you bring up the performance issue, you talk through the trials they’re going through, or you communicate the changes that are being made.

In other words, the honest and uncomfortable things.

Now, a common mistake many leaders make is to water down what needs to be said to avoid things feeling uncomfortable.

You can’t do that.

You’ve got to have the courage to say what needs to be said.

Don’t dance around the point or sugarcoat anything.

For some reason, people think it can be unkind or insensitive to be honest.

Do you know what the opposite of honesty is?

Dishonesty, deception, lying, hypocrisy…

Does that sound kind?

NO!

You’ve got to be honest.

And not only that, but you also have to be clear.

Clarity brings understanding and confidence.

A lack of clarity brings confusion and doubt.

So, be honest and clear.

Now, this could certainly lead to feelings of hurt, defensiveness, or discouragement, but that’s where the fourth principle comes in.

PRINCIPLE 4: ENCOURAGEMENT

So, we’ve listened, shown empathy, and been honest and clear.

This is a good time to share some encouragement.

Encouragement is recognizing the good in the situation or the good in the person.

In my mind, it’s unfair to only recognize the negative and ignore the positive.

Now, to be clear, this isn’t always the case.

For instance, if I’m with a family mourning the grief of a loved one.

It’s not always appropriate to look for something positive.

No, you need to let them grieve.

But you can still encourage in other ways.

You can hug them, you can hold their hand.

You can just sit in silence with them.

At the end of the day, encouragement just needs to be authentic and sincere both for the people involved and the context of the situation.

It can’t be contrived and forced.

Encouragement is such an important part of handling all the hard conversations we face in leadership.

Let’s hit the fifth principle.

PRINCIPLE 5: BE A SERVANT

This principle centers around demonstrating humility and love.

It’s a posture you have.

A great question to ask, and I usually say it at the end of a hard conversation, “How can I serve you?”

Do you see how disarming and loving that feels?

Now, you can’t just say it.

You need to actually mean it.

“How can I serve you?”

Even in the most intense moments of fear, frustration, grief, and confusion, that one question can cut through the noise and bring peace, unity, healing, and comfort.

“How can I serve you?”

It’s powerful.

Listen, if you apply these five principles, you will have everything you need to navigate even the most challenging circumstances.

Keep in mind that all of the principles are just that, principles.

Don’t turn this into a formula; that’ll feel insincere, and it won’t work.

But look, I get that some of you might have been fishing for some practical advice.

So, let me give you a bonus round of quick, practical tips you might find valuable.

This is stuff that I have found really helpful to me personally.

I’m just going to rapid fire them at you.

Ready?

TIP 1: CONFLICT IS CANCER (ADDRESS IT IMMEDIATELY)

Do not let conflict fester. It will continue to grow, and it will kill you and your organization.

Deal with it swiftly.

TIP 2: HIRE SLOWLY AND FIRE QUICKLY

I got this advice from my dad.

I don’t know what else to say.

It’s good advice, and it can save you from having to have a hard conversation in the first place.

TIP 3: DO NOT HAVE ANY OF THESE HARD CONVERSATIONS OVER TEXT OR EMAIL

No. No. No.

Do not do this.

There are almost no exceptions to this rule.

And I don’t even want to share the exceptions because I don’t want you trying to justify doing this.

I know it seems easier.

But that’s because it’s passive.

You don’t want to be passive about these things.

I would even advise you to avoid phone calls for hard conversations.

These methods are hard to read emotionally; there’s zero body language, and it’s almost impossible to build any kind of connection.

It doesn’t work.

Don’t do it.

TIP 4: SAY LESS, GOD BLESS.

Need I say more?

TIP 5: FIND A MENTOR

When it comes to hard conversations, it’s so much better to learn from a mentor than to learn through trial and error.

This is the main reason I launched my mentorship program not too long ago.

There are some things that are just difficult to navigate in a video or a book.

Sometimes you need hands-on mentoring to navigate the nuances of leadership.

Hard conversations are certainly at the top of the list of things I would recommend mentoring for.

I won’t say a whole lot more on that, but if you’re interested, you can find a next step at the bottom of this page.

I’d be happy to work with you in a 1-on-1 capacity, but just know that the mentoring slots are application-only, and I can only accept a handful of individuals.

TIP 6: LEAD WITH SERVICE (Principle 5)

If there is one principle I would advise you to lead with, it’s service.

In other words, lead with love.

At the end of the day, if you put this principle first, you can walk away from that hard conversation knowing you did the right thing.

You can walk away knowing that you did right by that person, you did right by that situation.

No matter the outcome, you can feel confident that you did the right thing.

And listen, I’ve had outcomes I don’t like, but I still leave the conversation feeling 100% at peace with how I handled it.

In many ways, that’s why these principles work.

FINAL TIP: PRAY

You may not be a person of faith, that’s fine, I’m still your friend.

But this is the best advice I can offer you for handling hard conversations.

As a Christian leader, this is my secret weapon.

I pray before, during, and after any hard conversation.

I’ll even be praying while I’m listening to the person talk.

Especially if they bring something up that I wasn’t prepared for.

I lead with prayer.

You partner prayer with all of these principles?

You kidding me?

Well, before you leave, I have a few book recommendations on this topic of hard conversations that you might want to look into.

These aren’t affiliate links, by the way, they're just honest recommendations that I personally found helpful.

The first one is “Boundaries” By Dr. Henry Cloud and Dr. John Townsend

The second one is “I Hear You” by Michael Sorensen (this one really helped me with listening and empathy).

If you want even more recommendations, I actually put together an entire leadership resource list with over 50 additional recommendations, broken down into Self-Leadership, Leading Others, Organizational Leadership, etc.

You can find that at the bottom of this page or on my website: zachwhite.com

As always, keep fighting the good fight!

I'll see you again real soon!