How to Master Difficult Conversations at Work with Confidence

Takeaways

Master the art of navigating challenging conversations at work. Learn to understand contributions, manage emotions, and address identity impacts for more effective and constructive dialogues.

Several years ago, I was working with a company that had given their founder a legacy position on the board to honor them for their past accomplishments, as they hired a new leader. While this founder maintained an affable, supportive, and innocent posture while in board meetings, during side conversations with senior staff, they would become manipulative and aggressive, trying to bully them into using the organization’s operations and finances to benefit their personal agenda.

The staff politely stood their ground against these attempts to undermine their integrity and the integrity of the organization, but as the threats escalated, it was clear that they desperately needed the board to step in and resolve this at the board level. That is actually when the situation became difficult.

Ideally, the board chair, who had been consulted by the staff as these encounters unfolded, would have stepped in with a challenging conversation with this founder. The board chair was a well-known leader with an incredible resume of successive high-level leadership positions but was paralyzed by the specter of this demanding conversation looming. Promises to have the conversation repeatedly turned to excuses and requests for the staff to be patient and hope and pray for the founder to change.

After months of abdication by the board chair, the situation only worsened, until the exasperated staff appealed to the broader board who immediately stepped in, appointing a courageous board member to lead a special meeting to address the situation and bring a resolution which ultimately included removing the founder from the board.

It is easy to be an armchair quarterback, particularly in hindsight, and say the board chair should have stepped in earlier. But it is so hard for all of us when we are in these situations. As leaders, we all face challenging conversations every day, most of us several times a day. And they don’t always go well. It is understandable to be hesitant to jump into another one.

If you are like me, I am always looking for ways to learn how to increase my ability to navigate these conversations constructively.  I wish that being given a role or title, also meant we were granted an immediate increase in skills, like leveling up in a video game, but it doesn’t work that way.  We have to work at it. Instead, too many leaders, see their conflict skill level like a toddler sees the dirty diaper they are sitting in. “I know it’s a mess, but it’s warm and it’s mine so I’m just going to gut this out as long as I can.”

There is a better way.

Some tools can be learned to help you navigate a challenging conversation. This is not about some toolkit that helps us “win”, or get our way. It is not even about increasing your skill of message delivery or technique, or even about being understood. If we are still approaching challenging conversations, trying to get all our arguments water-tight, a perfectly dialed-in script to make our case, we aren’t ready for a challenging conversation. Those are all techniques that will likely take the conversation in the direction we don’t want it to go.

Challenging conversations are not about message delivery, but about learning. If your purpose is to learn about why we are missing each other, why there is friction, or why they see something differently than we do, then we can make real progress.  In her book, Difficult Conversations, Sheila Heen does a fantastic job of breaking this learning into three layers. I use a similar framework when coaching clients but if you are looking for additional reading, her book is highly recommended.

Most of us prepare for a difficult conversation by defining what has happened which is the best place to start.  But instead of focusing on your theories about why they are so difficult or why they won’t apologize, whose fault it is, and their intentions; step away from what you’re right about and try to put yourself in their head and understand better why they think you are at fault. This first step is all about replacing certainty with curiosity.

1)    Own your Contribution

This will help you get to the heart of what will be helpful in this first stage, which is owning the ways you contributed to this. Too often we approach a conversation wanting to attach blame.  And if you have ever been in a culture of blame, you know how unhelpful that is. Shift from blame to contribution. Blame looks for whose fault it is mostly, usually to punish. Instead, assume that everyone involved contributed, so everyone has something to own and change to fix the problem.

The most common contribution is that you saw it coming but did nothing. Another contribution that is often missed is simply being unapproachable. Don’t try to downplay the significance of these “sins of omission”. If you can approach the conversation understanding how you contributed and be honest and accountable for that, it is an invitation for others to be accountable as well.  When everyone owns their contribution, we can fix the problem.

2)    Talk About Your Feelings

We also need to talk about our feelings, or these emotions will find a way to escape in less healthy ways. Conventional wisdom has been that we shouldn’t talk about feelings at work. But when it comes to hard conversations, there are two parts, the problem we are trying to address and the way that problem has made us feel about each other. To reach a solution, we usually need to address both sides of this. When I have a coaching client wrestle with a show of emotion at work, whether that be raising their voice, crying, or pounding their fists on the conference room table, it is usually because they lack a better way to release that emotion. Talking about those feelings is usually the healthiest way to release that emotion.

This second issue is more important than the first. Traditional advice is to just be objective and rational and function like a robot. The problem is that we are not robots. We all have feelings and need to deal with our emotional reactions to each other. You may feel confused, frustrated, concerned, angry, or even hopeful. Expressing that productively is essential. 

As essential as the first step of contribution is, if we only focus on that, we are just solving a surface issue, and don’t deal with the underlying issue that we need to talk about, which may be that you don’t listen to me, or you are making decisions without me. The real issues usually surface when we can identify the emotions we are feeling, which often point us to the real issue. For instance, conflict might be brewing over missed deadlines. In step one, you need to own your contribution which may that you aren’t getting your deliverables on time. But when you start to identify your emotions, you may realize you feel overwhelmed. If you can talk about it, you can then dialogue about the lack of equity in roles which is producing your real conflict.

What do you do if you start getting emotional when you talk about your emotions? While getting emotional is rarely helpful, if it happens, try to name your emotion which usually serves as a healthy relief valve for that emotion. But if the tears flow, let the person you are with know what to make of it. Don’t leave it to them to process why you are emotional. If you don’t address it, they are left feeling like they “made someone cry” or that you are mad at them and it only makes finding and resolving the issue more challenging. A great step is to say, “I’m passionate about our work, I want to work well together and I just need to take a quick walk to reset. Can we try this again in 10 minutes?”

3)    Understand How This Affects Identity

As important as identifying Contribution and Feeling, the third layer of Identity is the most important factor in a hard conversation. It is what makes a hard conversation hard.  And it is the part of the conversation we are having with ourselves about ourselves. We tell ourselves a story about ourselves, about who we are and who we hope to be in the world. But when we get into conflict it raises questions in our minds about if we are the people we intend to be. What we do with these questions determines not just how these conversations go but who we become.

There is something about the conversation that is suggesting something about you. Do they not respect me?  Am I not competent?  Did I not do something right? It is essential to be aware that this is why this conversation is hard for you. And that is why it is hard for the other person as well. What do you fear this conversation says about you? And what do you think the other person fears the situation says about them?

One of my hard conversations was with a long-time mentor whom I had worked with for years. He had successively progressed in his career and had given me opportunities to advance along with him. When an incredible offer came from another company, I couldn’t pass it up, but I dreaded telling him my decision. I feared that this supportive boss would somehow see me as ungrateful or someone who would abandon a friend. But identifying it and naming it in that conversation took away the power of that fear.

4)    Tactics, Tips and Timing 

Now, that you have this layered approach as part of your toolkit, when should you have the conversation? If your real purpose is to change them or control their reactions, you are not ready for the conversation. If you are endlessly rehearsing with yourself how to perfectly make your points to explain how right you are, you are not ready for the conversation. If you have shifted from “telling them off” to genuine curiosity and wanting to better understand them, you are in a learning posture and are ready to have the conversation.

Keep in mind that if you tackle the big question of “How am I contributing to this?” and you can see ways that you have contributed to the problem, it may not help to talk about it. You should just do something different and stop contributing to the problem.

In working with one client, I heard repeatedly of a senior leader who was often tasked with taking on challenging conversations for the organization. In meeting her, she was clearly skilled in interpersonal dialogue but it was also clear that while hard conversations with her often ended with little conflict, they ended with even less clarity. People whom she was sent to fire walked away, liking her but unsure if they still had a job or not. The organization mistakenly thought she was great at this because they valued peace more than truth. Unfortunately, the result was an organizational culture of false community with an institutionalized confusion of what honest dialogue even looks like.

With that rich ideological backdrop, let me offer a few great tactical frames and phrases as you navigate your next challenging conversation.  

Start by giving a “heads up” as the conversation begins like, “I need to have an uncomfortable conversation with you.”  It helps the person take a breath and prepare to navigate this with you.  Without a warning, they may feel ambushed when they realize what is going on.

Lead with humility by saying something like “I’m nervous about this because I’m not sure how it is going to go.  Please be patient with me as I am trying to figure out what is going on. This relationship matters to me and I don’t want to avoid this, I want to go through this with you.” 

It is a good tactic to ask permission to have the conversation at this time. They may want to press pause to make sure they are emotionally ready or have enough time blocked off to process with you.

When talking about feelings, it is helpful to be specific.  Don’t just say you are sad or mad.  The more specific you can identify your feelings, the more helpful you are being. Are you uncomfortable, afraid, or confused?  Be specific.  The same is true when describing behaviors and the impact of those behaviors. Don’t generalize. Pick recent and egregious behavior, and don’t exaggerate about its frequency. Don’t say they always do it, if it happens once a week or month or just started recently.  Personalize when you describe the impact.  Don’t invoke the whole organization as If you have an invisible army behind you. “Everyone around here is frustrated with you.” That is manipulative, usually not true, and easy for them to discredit. Keep this to your concerns.  “I fear that if we don’t deal with this, there will always be tension between us.”

As the conversation gets underway, commit to finding the third story. You have a story that you are confident about with your observations and concerns, usually centered around the other person’s misdeeds. But they also have a story and it is probably centered around your misdeeds. So what would a dispassionate third-party mediator say about this situation? That is a story we both feel we can be part of.  It doesn’t mean you can’t speak from your vantage point once the conversation starts but don’t ever start with your story. Put both stories on the table, stitch them together, and then ask, “How do we solve the problem together.”

Listening is at the heart of this, but listening is the first skill to go out the window when the conversation gets difficult. Stay committed to asking good questions, always seeking to understand.  “That’s not making sense to me yet.”  Rephrasing what you are hearing regularly will help take their emotions down a notch, “I think what I hear you are saying is this. Am I getting it yet?”

Be genuinely empathetic but don’t stop there. You do need to speak up for yourself but never lead with that.  Let’s be honest. You’ve probably been mad at them for a long time because you would rather have that than risk them being mad at you through this conversation.  But if you don’t share what you are thinking and feeling, you are not bringing your full self to your work.  It is OK to still speak about your viewpoint even if it is conflicted. It is fine to say to someone, “I’m grateful for your contribution, but I need more from you.”

And finally, people don’t change because of one conversation.  As a leader, you have to develop this like a muscle. Keep using these techniques. Even when the challenge pops back up and needs to be discussed. Again. Keep reframing the issue.

Stay curious and kind.