The Biggest Mistake Leaders Make When Having Difficult Conversations and How to Avoid It

What makes difficult conversations so difficult?

If you’re the boss in your workplace, you have the ability (and the responsibility) to sometimes pull rank, call the shots, and make tough decisions. This is an absolutely appropriate way to deal with certain difficult situations, assuming it’s done in a way that doesn’t shut people down.

If “taking a stand” is your default leadership style, however, you’ll probably run into trouble pretty quickly because the bottom line is that your people’s needs aren’t getting met. And this isn’t the best long-term team-building strategy for you.

So let me let you in on a little secret… the biggest mistake that leaders make in difficult conversations is that they waste their time arguing about positions instead of dialoguing about underlying needs.

This is because many leaders don’t really understand how to have difficult conversations in a way that enables them to get their needs met, while at the same time meeting the needs of the people they lead.

Let’s break it down…

If you’re managing a team that’s leading a big project, you may prefer to have everyone update the project plan on a weekly basis. Perhaps you need this information to keep your boss appraised of progress, concerns, questions, etc.

Breaking this down into positions and needs:

Your position: Team members update the project plan once a week

Your underlying need: Information

Now perhaps Sally is on your team, and Sally prefers to update the project plan at the end of each month. She finds that this is the most efficient way for her to work given her natural preferences and time constraints.

Sally’s solution: Update the project plan every month

Sally’s underlying need: Efficiency

You and Sally could argue for days about whether the project plan should be updated every week or every month and get nowhere. But as soon as you shift the conversation to a dialogue about how to meet both of your underlying needs (i.e., information and efficiency), you have a solid foundation to come up with options that actually work for both of you.

A conversation about “How do we meet both of our needs?” could lead to options like:

  • Sally shares her updates at weekly team meetings.
  • You ask Sally when you need information about the project and she proactively raises issues with you.
  • Sally updates you at your weekly individual check-in meetings.
  • Joe (a co-worker) takes a small task off Sally’s plate, freeing up time which she will use to update the project plan every week.

And the list goes on. The point is that now you’re working towards a resolution that you both can buy into! And this is how you get your needs met, while meeting the needs of others.

Quick Tip: A position is nothing more than a person’s preferred solution for meeting their needs. The way to distinguish between positions and needs is that positions can only be satisfied in one way (or very few ways), whereas underlying needs can be met in many different ways.

How to Avoid the Biggest Mistake

The problem with most difficult conversations is that the underlying needs of each individual remain below the surface in the conversation, or in other words, they are left unsaid. So it’s no wonder that we find ourselves spinning our wheels!

Underlying needs are kind of like the roots of a tree – we don’t see them but they play a crucial role. They anchor the tree to the soil, provide it with nutrients, give it support for its structure, etc. A person’s underlying needs are often based on their goals, their desires, their values, etc. In other words, all of the things that make up who they are as an individual.

Your mission, if you choose to accept it, is to hone your open-ended questioning skills so that you can help surface the underlying needs of others when you’re faced with a difficult conversation. Questions like the ones below will help you do this:

  • Walk me through your thought-process here.
  • Tell me what’s most pressing for you in all of this?
  • What’s your biggest concern right now?

This approach can be challenging when you’re feeling frustrated, but it opens up the possibility of having a deeper and more meaningful conversation that actually resolves the issue at hand.

And keep in mind that in most situations there are usually key joint needs that both people share, such as running a successful project. You may have different ideas about how to get there, but keeping these key shared needs in mind is incredibly helpful… especially if the conversation starts to become heated.

You can use joint-needs to refocus the discussion if things escalate, for example: “Hey, I know we both really want to ensure that this project is a success. We just have different ideas about how to get there but our end goal is the same. Let’s get back to talking about options that might work for both of us. Say more about why [xxx] is important to you…”

Working towards win-win resolutions may take a more time in the short-term, but building this type of goodwill with your employees will pay off in spades in the long run.

The Highway Analogy – How to Stop Other People from Derailing a Conversation Without Offending Them

Having difficult conversations can be a little like merging onto the highway.

I know this analogy sounds far-fetched… but stay with me here for just a moment.

Preparing for a difficult conversation is one of the best ways to ensure that it will be successful.

But what if the other person throws something at you that comes out of left field?

You’ve spent all this time mapping out your needs, anticipating what might be important to the other person, thinking of potential win-win solutions (more on these topics in upcoming posts!)… and all of that gets derailed in one fell swoop.


So here’s the deal, as much as you can prepare for a difficult conversation, you can’t anticipate everything that the other person will say or need.

And this is where the highway analogy comes in.

If you’re clear on which topics you’d like to discuss, you can consciously assess the importance of the new topic and then decide whether you need to “speed up” or “slow down” to deal with the issue instead of just getting derailed by it.

Speeding up (in a collaborative way) is essentially saying something like – “That’s a really important topic and I’d love to discuss it with you. Let’s set up another time to talk exclusively about that so that we can give it the attention it deserves. For this meeting, let’s focus on what we decided to discuss – [insert the agenda items that ideally you would have agreed upon together beforehand.]”

Speeding up is a helpful technique when it’s more important to focus on the topics that you had intended to discuss first.

And when you can make it safe for the other person by helping them see that you’re fully committed to addressing the new issues they’ve raised (just at another time), it helps them come back to the conversation at hand.

But sometimes the thing that comes out of left field from the other person is actually more important… and needs to be dealt with first.

If that’s the case, then slowing down to talk about their topic makes sense. And here again, it’s incredibly helpful to make this explicit so that everyone knows that you’ll come back to the other topics later.

It sounds SO simple, doesn’t it?

However, I can’t tell you how many executives, managers, and professionals I’ve shared this analogy with and watched it “click” things into place for them.

The clients that I work with need to have numerous conversations with the people in their workplaces every single day… and many of them are difficult conversations. So simply strategies that can help people quickly course correct when things get off track are worth their weight in gold in my books!

This analogy came to mind for me when I worked as a workplace mediator. Part of my job was tracking the conversation between parties to help make sure that they addressed everything that they wanted to talk about.

Whether I was working with two individuals or an entire team, everyone was always clear on what would be discussed beforehand.

In some of my sessions, however, I would see parties skirting around the more contentious issues. They’d want to talk about everything else that was going on in the workplace instead of addressing the actual issues between them.

My job in those moments was to check in and find out if this is how they wanted to spend their time – essentially highlighting that they had a trained professional in the room who could help them work through their sticky issues and they could take advantage of that or they could continue to talk about things that they probably didn’t need my help to discuss.

This usually brought them back on track and they were always grateful for the intervention.

But sometimes they would let me know that they actually needed to address the issue they were talking about before they could get back to the other topics.

This was also great for me to hear! Mainly because my goal was to help ensure that they made the most productive use of their time with me. And I generally found that whatever they were discussing got wrapped up much more efficiently than it would have been otherwise. Bonus!

In other words, speeding up and slowing down was something I had to navigate constantly with parties in my work as a mediator.

People generally don’t like wasting their time, but they’re sometimes scared to address sensitive issues. When you can lead them there gently and help them understand that you want to work with them to fix things, they generally tend to hop on board.

Most people actually appreciate being held accountable in a supportive way. And sometimes we need to check ourselves and readjust our plan based on new information that emerges in the situation.

The key here is that when we choose to speed up or slow down consciously, we avoid getting derailed.

So the next time you have a conversation and you feel like things are falling off the rails, remember the highway analogy and consciously choose what to do about it.

Let me know how it goes! I’d love to hear back from you.

How Your Way of Handling Conflict at Work Might Be Hurting You

The Importance of Consciously Choosing Your Conflict Handling Style

We all have different ways of handling conflict based on our upbringing, our experiences, our core values, and many other factors. Our default approach may work well in some situations, but it may work against us in others.

This is why it’s important to understand your default style so that you can consciously decide whether that approach is the best one in a situation (as opposed to acting on “auto-pilot.”)

It’s also helpful to understand which styles the people you work with tend to use you so that you can adjust your approach, if necessary.

According to conflict-handling behaviour theorists Kenneth Thomas and Ralph Kilmann, Ronald Kraybill, and others, there are 5 basic approaches (or ways) to deal with a conflict. And they centre around two key factors:

  • Your level of focus on the issue (i.e., the task, your needs, and your goals). Another way of looking at this is your level of assertiveness.
  • Your level of focus on the relationship (i.e., getting along, the other person’s well-being, and the other person’s needs). Another way of looking at this is your level of empathy.

The 5 Styles

Here’s a brief description of what the styles looks like and some of the pros and cons of each one:

Take a Stand (high assertiveness & low empathy): “I can’t budge on this.” This style usually generates win/lose outcomes.

This style can be useful in situations when the issue is too important for you to compromise on. And just for the record, it’s quite possible to take a stand without being confrontational. The downside, however, is that even when it’s done amicably, this style can upset others because their needs are not met through this approach. This style can also be harmful to relationships in the long run if it’s overused.

Do Nothing (low assertiveness & low empathy): You won’t hear much from someone using this style. They’re not actively pursing a solution to the situation or trying to maintain the relationship. This style usually generates lose/lose outcomes.

This style can be useful when you’re not involved in the situation and there isn’t a clear benefit to your involvement. The downside of this approach is that others may feel frustrated if they want you to become involved. And if you do happen to have some needs at play in the situation, they won’t be met through this approach.

Give In (low assertiveness and high empathy): “Sure! We’ll do it your way.” This style usually generates lose/win outcomes.

This style can be useful when the issue isn’t important to you and when you want to focus on meeting the other person’s needs. As with all the styles, this one is perfectly appropriate. However, if it’s used excessively and your needs regularly don’t get met, you’ll probably end up feeling resentful and this in and of itself will damage the relationship.

Compromise (moderate assertiveness and moderate empathy): “Let’s meet halfway.” This style usually generates outcomes where both people win a little and lose a little.

This style is great when you need to come to a quick resolution and the issue and relationship are somewhat important in the situation. The downside of this style is that not all of your needs get met through this approach and the other person also won’t have all of their needs met in the situation.

Collaboration (high assertiveness & high empathy): “Let’s find a way to make this work for both of us.” This style usually generates win/win outcomes.

This style is appropriate when both the issue at hand and the relationship are important. It essentially involves advocating for your needs to be met… and also advocating just as strongly for other person’s needs to be met. The downside is that it can take a more time to use this approach and it’s not ideal when a quick decision is required.

Food for Thought

All five styles are appropriate and effective if used at the right time and in the right context. It all depends on what your particular goals are in the situation.

As you can see, certain styles require more assertiveness and certain styles require more empathy. Both assertiveness and empathy are core leadership competencies.

Assertiveness is the ability to express your feelings and thoughts appropriately. And empathy is the ability to recognize, understand, and appreciate the way others feel.

One possible way of viewing our choice of styles is this:

  • When we choose to use a style that requires us to be more assertive, it doesn’t necessarily mean that we don’t have empathy or care about the relationship… it simply means that the issue is really important to us in that situation.
  • On the flipside, when we choose to use a style that requires us to be more empathetic, it doesn’t necessarily mean that we don’t have the ability to be assertive or care about the issue… it can simply mean that the relationship is really important to us in that situation.

Maintaining a neutral perspective about the styles can help us test out new approaches that are outside our comfort zone. And it can be useful to maintain this neutral perspective when we come across others who are using a style that we may not like.

The key here is to make sure that we’re not overusing one style… and as a result, experiencing the downsides of this. There are 5 styles for a reason. We encounter many different situations at work and in life so why not use the style that will work best for us!

It’s also important to keep in mind that difficult situations and conflict are dynamic in nature.

You may decide to use one style at the beginning of the situation and as things evolve, you may eventually decide to switch to another style that is more fitting for the new circumstances.

It’s this type of reflection and flexibility that will allow you to maximize your chances of reaching your goals and a successful outcome.

So the next time that you encounter a difficult situation at work, try consciously reflecting on which style would be most helpful in the situation and see what you might do differently to improve both your impact and your results!

For more information please also see:

“When a child is learning how to walk and they fall down 50 times, they never think to themselves, ‘Maybe this isn’t for me.’” – Anonymous

How Mindset Eats Strategy for Breakfast When It Comes to Dealing with Conflict

We often fear conflict in the workplace because we’ve experienced the negative impact of poorly handled difficult situations.

When not handled well, conflict can absolutely take a heavy toll on individuals, teams, organizations, and even on our friends and family outside of the workplace. And it can result in lost time and energy, damaged relationships, and decreased productivity.

But if we set aside our past experiences for just a moment and take a look at a definition of conflict, it’s actually quite neutral:

Conflict can be defined as a real or perceived difference between what is important to one person and what is important to someone else. 

At work and in our lives, we cannot help but encounter differences in priorities, approaches, perceptions, and beliefs every day. However, conflict itself is not inherently good or bad, it’s the way that it’s handled that makes all the difference.

When handled well, conflict can actually have some very positive benefits, such as the development of new and creative solutions, better communication, and healthier relationships.

The question then becomes, how can we maximize the benefits of conflict in the workplace and minimize its negative impacts?

Mindset Eats Strategy for Breakfast When It Comes to Conflict

The most important place to start is your own mindset. As the saying goes, whether you believe you can or you can’t, you’re right.

If you believe that conflict is bad, then when a conflict occurs you’ll be more likely to react from a fear-based perspective – i.e., in fight, flight, or freeze-mode. And your reaction will have an impact on how others respond to you. In essence, “When you’re scared, you’re scary.” (Anonymous) This type of interaction will probably result in negative outcomes, which will then reinforce your belief that conflict is bad.

On the other hand, if you believe that conflict is normal and an opportunity for something positive to emerge, you’ll be more likely to respond in a way that opens up communication – i.e., through personal reflection and dialogue. And this response will have a different impact (a more positive one) on the other people involved. This will increase the chances of there being a positive outcome to the situation and will reinforce your belief that conflict is normal and an opportunity.

Whether we like it or not, conflict will occur in our lives. It’s kind of like death and taxes. So, given that it’s inevitable, it’s important for us to examine how we think of conflict so that we can view it in a way that will help create the outcomes we want.

Mindset is one of the first pieces that I work on with clients in my Coaching Program. Shifting out of those hard-wired fight, flight, and freeze reactions takes commitment, patience, and effort; however, once this piece starts to fall into place, the conflict resolution strategies that we cover in the program become exponentially more effective!

So take a moment and check your mindset.

  • How do you currently view conflict?
  • How would you like to think about conflict?
  • How can you get into this mindset the next time you encounter a difficult situation in the workplace?

Wishing you happy reflections 🙂