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Principles for Challenging Conversations - Main

When I deliver training to help people with challenging conversations, I notice something interesting.

It seems that many people are looking for the perfect thing to say.

The perfect opening to the conversation, for example. That opening line that won’t upset anyone or have them bursting into a fit of rage.

Or the perfect process. The ultimate challenging conversation model that will unlock everything and solve all our problems.

You Don’t Need a Perfect Process, You Just Need a Process

Unfortunately, a perfect model or phrase for challenging conversations does not exist.

There are lots of good ones out there, but they don’t provide the perfect solution. You’ll still feel uncomfortable, and the other person may still get upset.

So instead of looking for perfection, I think we should focus on principles instead.

In this post, I’ll outline the important principles that I believe are helpful for successfully undertaking a useful challenging conversation.

But before we get started, there are good resources out there to help you with a framework or two – here are some options:

So What Is a Useful Challenging Conversation?

A few paragraphs earlier, I mentioned that we want to have a useful challenging conversation.

So what does this mean?

Useful Challenging Conversations

For me, a useful challenging conversation results in:

  • Heightened awareness: The other person is aware that there is an issue, or a challenge to be overcome. And they also know that you are aware, too.
  • Greater understanding: Both sides have had the opportunity to raise their grievances or put across their point of view. Both parties understand the other side more than they did before.
  • An expectation has been set: By having the conversation, both parties are aware that the current situation or issue can’t continue as it is.
  • A plan is in place: There are actions or steps in place to make progress on the issue. This includes a follow-up to check on progress.

This doesn’t mean that the problem is perfectly resolved. There may still be differences of opinion that are hard to address.

But the issues are out in the open (between you and the other person, at least) and a path forward is being forged.

Why Focus on Principles for a Challenging Conversation?

The reason I like the idea of principles for a challenging conversation is that they can be quite simple.

Rather than trying to memorise your opening line, or exactly what you’ll do if a certain event happens, or to stick to a precise process, I find it better to focus on broader principles.

If we have, say, three or four simple principles that we keep in mind during a challenging conversation, we’re easily able to remember them. And we can more easily keep them at the front of our mind, even in the thick of a challenging conversation.


Mike Tyson famously said “Everyone has a plan until they get punched in the face”.

The plan, in this case, is the perfect process or opening line, or that sentence you’ll say to get your point across in just the right way.

And getting punched in the face in this context is that flood of emotions, the anxiety and potential emotional outburst that derails our finely laid plans.

Learn More:  Avoiding a Difficult Conversation? Ask Yourself These 3 Questions.

3 Simple Principles for a Challenging Conversation

OK, so let’s take a look at some simple principles that hopefully you can keep in mind, when you’re in the thick of a challenging conversation.

Principle #1: Realise It’s Not All About You

Going into any challenging conversation, it’s natural to focus on ourselves and our feelings.

Maybe your team member is behaving badly or underperforming. As leaders, this can have us thinking negative thoughts.

How dare they make me and the team look bad?

My boss thinks I’m a bad leader because of this stupid person!

We may take the situation as a personal slight against us. That the other person is attacking us by being disobedient or disrespectful.

But the reality is, it’s not all about you. In fact, if you’re a thoughtful leader, there is probably very little of it that’s about you.

Leadership Ego - Main

Let’s take a little look at an example.

A newly promoted leader is having difficulties with one of their team members. They used to be colleagues, but now they manage the team.

The team member is being disrespectful, talking back and questioning the capability of the newly promoted leader in front of others.

Sounds like a challenging conversation needs to be had.

The leader, in this case, is frustrated. It’s not nice being disrespected in front of the team. And the team member is being rude and unprofessional.

At first, the leader may feel like it’s a personal attack on them. But what else might be at play?

Firstly, the team member may feel annoyed that they didn’t get the promotion, and the current leader did.

They may also feel upset because they feel like they’re not doing well in their career and this is another backward step. Perhaps they are having financial struggles, and this promotion would have really helped. This might just be another knock on their already low confidence.

As you can see, there are lots of possibilities that don’t involve the leader in this scenario. It’s more about what’s going on for the other person that may be bringing out this bad behaviour.

What This Principle Does For Us

If you can enter a challenging conversation knowing that it’s not all about you, it’s powerful.

Firstly, you’re less likely to take things personally. There are so many other potential factors involved (see the iceberg model here for more on this).

Second, you’re less likely to demonise the other person. What the other person is feeling is probably quite natural, so you’ll be less likely to be overly critical and go into attack mode.

And third, it helps us to get curious. “I wonder what’s going on for the other person, for them to act like this?”

Which leads us to the next principle.

Principle #2: Make an Effort to Understand the Other Side

Empathy - leadership qualitiesThis one follows on nicely from the previous principle.

In a challenging conversation, it’s important to make an effort to understand what’s going on for the other person, instead of focusing on ourselves.

The principle to remember is to understand the other side. In practice, this means:

  • Asking questions. Open questions to find out more information, and closed questions (Yes / No, True / False, Black / White) to confirm that you understand; and
  • Sitting and listening. Instead of trying to impose your solution or opinion on the conversation and “win”, focus on their opinion instead.

Following this principle is useful, because it signals that you are interested in what the other person has to say.

They may feel unheard and undervalued, which may actually be a contributing factor behind the challenging conversation in the first place.

This also shows a lack of self-interest on your part. Self-interest is a trust destroyer, so the more we can minimise it, the better.

Learn More:  Why Building Trust Is Better Than Authority.

Principle #3: Acknowledge Emotions, But Don’t Let Them Overtake the Conversation

One thing I hear often from leaders when it comes to challenging conversations is that they are impressed with people who can “take the emotions out of the conversation”.

Empathy image - brain vs. heartI can see where they are coming from, but I don’t think it’s quite right.

We don’t want to ignore emotions or suppress them.

We don’t want to only focus on facts and logic. They don’t tell the whole story, and often emotions are a strong driving force behind a person’s behaviour.

So in this principle, I find it useful to acknowledge and speak about emotions, without letting them overtake the conversation.

Acknowledging means speaking them out loud. Saying what emotions are coming up for you, and what might be coming up for the other person. Then testing your understanding by asking questions.

When faced with a leader who only focuses on results or cold-hard facts and logic, it can seem quite impersonal. It can give the impression that you don’t really care about what’s going on for the other person.

It may feel uncomfortable, but acknowledging yours and others’ emotions during the conversation may provide you with a perspective that you didn’t expect.

Challenging Conversations Are Imperfect, So Stick to the Principles

You’ll never have the perfect challenging conversation.

Someone will say something unexpected or unwelcome, and you’ll need to adjust on the fly.

That’s why I think that keeping some simple principles in mind is easier than engaging in detailed planning or memorising if-then possibilities in the moment.

That’s not to say we shouldn’t prepare, but hopefully these principles will help you navigate and adjust in the moment, and provide you with a sense of confidence when you do engage in your next challenging conversation.

What other principles do you think are useful for engaging in a challenging conversation? Let me and all the other thoughtful leaders know in the comments below!

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