Seth Dobbs (he/him): How often do you engage in difficult conversations? Do you try to avoid them whenever possible? And when you do engage in them, are you able to bring them to a positive resolution? When you think about it, what makes these conversations so difficult, anyway? Hi, I’m Seth Dobbs, and this is the Principle Driven Leadership podcast, where I share principles of leadership along with examples of how to apply them to help make you be the best leader you can be. These principles are based on my years of experience as an executive leader, in building organizations and then coaching others to become leaders themselves. And I believe that not only can anyone develop leadership skills, but that everyone can and should develop leadership skills. I think they’re essential in helping you achieve your best and whatever way you might be trying to make an impact. And that’s because leadership skills help you better influence others to effectively create durable results. And leadership is a journey. One that more often than not requires you to have difficult conversations.

Now the topic of difficult conversations is fairly broad. There’s a lot of material out there on handling both good and bad. I’m going to talk about difficult conversations from the perspective of Principle Driven Leadership.

In some ways, what people perceive as difficult conversations are actually at the core of conflict or perhaps more importantly navigating what we perceive as difficult conversations is essential to resolving conflict. An organization cannot become effective without being able to handle difficult conversations. Now for this episode, I’m going to split the concept into two key sections. First what makes a conversation difficult? And then the remainder on how to prepare for and navigate difficult conversations. So first, what actually makes a conversation difficult? You can probably think of many things that apply to you personally. Over the course of my career, I’ve encountered many reasons people perceive a type of conversation to be difficult. I think one of the biggest causes is fear. It can manifest in a lot of different ways. Fear of confrontation and disagreement. Fear of telling someone something they won’t like or something that differs from their own self view. A fear of being dismissed or thought to be unintelligent. The thing is fear is one of the most debilitating emotions and can prevent us from having what could be some of the most meaningful conversations in our careers. Now, this kind of fear can stem from many things.

For example, a lack of trust. Perhaps you don’t trust someone else to gracefully handle what you have to say, or perhaps you don’t trust yourself to handle it or handle if they have an aggressive response towards you. There’s insecurity, not being confident in what you’re bringing to the conversation can make you feel fear of being thought poorly of, or being flat out wrong. Bad experiences. Perhaps you’ve had a manager in the past that hasn’t handled a difficult conversation with your particularly well. And you’re worried that you’ll leave others feeling as poorly as you felt previously. So after kind of fear, one of the next big causes can be looking at the nature of the conversation itself. It can just be difficult to tell someone something about themselves that they might find upsetting. Or perhaps even worse telling them about something

they’re not going to get, like a job, a promotion, a raise, a contract. Getting someone to take a different tact than what they desire, to change their perspective of reality of the situation around you can just seem daunting. Because so many of us are enamored with our own viewpoints and perspective that challenging someone’s can actually be very difficult.

And this gets to the third major cause of concern with trying to embrace a difficult conversation. And that’s a lack of practice. Sometimes fear stems from simply not having experience in something. And to be sure many of us find just about anything we might tackle, if you haven’t practiced it to be difficult, regardless of nature. Now it can be challenging to get the opportunity to really practice having difficult conversations. But the techniques that I’m going to describe in the second half of this can be practiced in some ways, at least, and get you conditioned to approaching conversations in more productive ways. And there’s definitely more reasons that people avoid difficult conversations, more scenarios. But this helps set the stage for how to deal with them. And so with that background in mind, The remainder of this episode will focus on navigating difficult conversations. Now over the years, I’ve come to believe that for the most part, there’s really no such thing as difficult conversations; just poor planning and lack of preparation. And having been on the receiving end of a poorly handled difficult conversations I’ll say it certainly feels like it can stem from poor planning, lack of preparation.

And that’s not to say that the fears, the concerns, the challenging scenarios aren’t real. They are. But I think that most of us aren’t trained to work through these. And you typically don’t get to see good, consistent modeling of how to handle difficult conversations to learn from. So with that, I think there are five concepts to better handling, difficult conversations. One: avoid opinions. Two: avoid guessing what others are thinking. Three: talk about outcomes. Four: where possible drive conversations towards positive change. And Five: practice. So One: avoiding opinions. How often do you tell someone something along the lines of:

“oh, I think it would be better if you did X, Y, Z.” That’s a short statement, but there’s actually two things wrong with it. First saying, “I think”. That’s already inviting debate over what you’re saying. If you heard someone say, “I think” followed by something that you don’t want to hear. What are the odds that

you’ll reply, at least in your head with, “oh, you think that, well, I think you’re wrong.” This immediately shifts the conversation from something productive to an exercise in friction and frustration. If you got past that part of my sentence, you’ve now opened up a debate on “better”.

“Better” in the absence of any kind of agreed upon rubric or framework, has no meaning, certainly no consistent meaning, and as such, expressing opinions like this is a bad way to lead into any conversation. And will absolutely make it difficult because you’re setting yourself up for what will likely be a non productive discussion.

Number two: avoid guessing and assuming. This is the other big thing to avoid guessing at or making assumptions about: what someone else is thinking or feeling. I’m not sure that there’s actually an approach that can take you deeper into the land of unproductive conversation than this kind of assumption. And it takes the form of something

like: “I know you don’t want to do this work the right way, but we need you to”, or “I’m sure you feel like you’re being overlooked and so you’re sandbagging this job, but…”

Typically the immediate response to something like this is going to be: “that’s not what I’m thinking” or “that’s not what I’m feeling.” And instead of a discussion, you’re getting into a futile debate. It’s futile because you’re trying to argue about what’s going on inside of someone else’s head. Something you cannot possibly know anything about. And of course, that’s going to be a difficult discussion and at best it’ll be nonproductive, but likely creative and more friction. 

If you think about it, so many of our difficult conversations center around one of these first two things, if not, both. In fact, I sometimes think that’s what is making the conversation difficult. You’re navigating around opinions, emotions, assumptions, all of which can be challenging by nature. So if you can’t express opinions and you can’t talk about other people’s motivations and thoughts, feelings, and so forth, what can you do. That’s the third concept: talk about outcomes. This is what centers the approach in the Principle Driven Leadership paradigm. Now this isn’t about denying that opinions, emotions, feelings, and so forth exists.

Of course they do. This is about harnessing energy and centering focus on things that are much more productive to discuss: outcomes. Ideally you can measure outcomes. You can observe whether you are effectively moving towards goals. Towards the future vision. And you can measure or at least identify a lack of outcomes. And so this means you should always look at difficult conversations, even conversations where you need people to change their behavior, by looking at and talking about outcomes. Are they not reaching outcomes that they need to reach?

Are they creating outcomes that you don’t want that are getting in the way of forward motion? This kind of discussion is much easier to have. It’s much easier to agree on that than on what someone’s motivation might be or some other personal aspects. Said another way: instead of questioning the action or decisions people take, or the reasons for taking them, you should always be discussing the impact of those actions and decisions. People don’t always know others think they’re being a jerk for example.

And in fact, trying to have that discussion is typically fraught. It’s going to be very difficult. But if instead you observed that they’re not able to get the results that they desire out of other people, you can actually have a discussion around tactics to get better results..

Getting adept at shifting difficult conversations to focusing on outcomes is a powerful technique, and will help you and your team embrace more flexible and a more adaptable mindset if you get it right, which in turn then means you and your team will be better ready to face change and adversity and engage in problem resolution.

Now I have learned some of this the hard way. Many years ago, I had someone on my team, we’ll call them Felipe, that was failing in several regards. The short version is that I told him the team didn’t think he was doing his work. He wasn’t available when they needed him and that all around didn’t seemed to be focused on doing the job. Now based on everything I’ve said so far in this episode, I did pretty much everything wrong here. And yep,

I expressed an opinion and he told me I was wrong. He was in fact doing the work. He said he felt he was available. He felt he was very focused. So not surprisingly the first 10 or 15 minutes was unproductive because he was defensive from the start. Now, fortunately, I was able to pivot the discussion around other people’s perceptions as in “that’s great.

If you’re doing everything right, let’s just talk about how to manage perceptions then because people don’t see it.” And not ideal, but it actually gave us a handle to dig into the next concept. Driving conversation towards a positive change. So that’s number four. Drive conversations towards change in a positive way. You should think about your leadership conversations from the perspective of driving to one or more positive outcomes. For difficult conversations in particular, you’re often trying to get someone to take an action, to change a behavior, to get their head around a new reality so that they can move forward again. Any conversation that you perceive as difficult, that doesn’t move towards something positive, will often instead move to the negative, to hurt feelings, to irritation and frustration. This is the most important part of preparing for difficult conversation: knowing the outcomes that you hope to reach by having this conversation. Knowing what positive change you want the other person or people to take, and then navigating and guiding the conversation so that they too see the path as a positive one to take. Looking again at my conversation with Felipe. Going into it,

I thought my conversation was about getting him to do his job. That was destined to fail because I thought the conversation was about “doing”, not reaching or changing outcomes. Part of why I talk about achieving rather than doing so much is that one person’s doing is another person’s not doing. And what really differentiates things is the results, not the action. I think that’s what we typically really mean when we say “you’re not doing X, Y, Z”, that “you’re not making the results we’re expecting.”

So, as I mentioned, I was able to pivot the conversation with Felipe to how others were perceiving him. That’s not ideal in that we’re still talking about other people’s feelings and opinions, but neither of us could actually debate what was going on in someone else’s head that was not in the conversation. So we were able to shift gear and talk about actions to manage those perceptions. We talked about how he needed to aggressively communicate when he was out and unavailable. And he had good reason to be unavailable by the way that part was never in question. And then also to aggressively communicate when he wasn’t going to hit a deadline so that his manager could manage expectations with the team and with the client. This pivot managed to get us to work our way through to positive changes and outcomes.

And he did commit to becoming far more proactive in how he communicated.

So number five: practice. Practicing difficult conversations can be difficult in itself, because in any made up practice scenario, the stakes aren’t the same as a real discussion, the pressure, the emotions, the knee-jerk reactions, just don’t fire up the same way in a staged scenario. Nonetheless, you should practice rethinking whatever difficult conversation you need to have in terms of outcomes and positive changes, and then potentially try that path out with a safe partner that can give you feedback on if you’re hitting the four criteria I just discussed: avoiding opinions, avoiding, guessing, and assuming motivations and emotions, focusing on outcomes, and moving to positive change. You can also get folks to help you prepare for what you think might make a particular conversation difficult. For example, I was once coaching someone to make a presentation to a leader that was a bit of a bully. As he practiced presentation with me, I periodically interrupted him with other questions. And then before he could fully answer, I’d interrupt him with another question. So I could see him getting frustrated, really starting to get upset with me.

And then it clicked with him. I was impersonating the bully he had to speak with. Then he understood what I was doing and told me to carry on. And while he eventually realized what I was doing was just a deliberate technique, nonetheless helped him prepare for the real thing, which in the end, he actually handled quite well. So said another way you can actually combat some fears and lack of practice by practicing a discussion with a friend who role-plays a behavior that you fear. This will help you get used to recentering around outcomes and positive change, no matter what happens and avoid opinions and assumptions.

So many months later, Felipe came back to me and thanked me. He realized in hindsight that he wasn’t really getting his job done, or really more specifically as we discussed, not reaching the outcomes we needed him to. And he appreciated that I spoke to him about it and gave him the space to change. I can’t think of a better outcome than that. Navigating, what we perceive as difficult conversations is essential to resolving conflict, to get better at handling difficult conversations. You should first take some time and analyze what makes a conversation difficult for you both in general and in specific circumstances. And then use the five concepts to help you better navigate. Which are One: avoid opinions. Two: avoid guessing or assuming what others are thinking and feeling. Three: talk about outcomes. Four: steer conversation towards positive change and Five: practice. Because even a little bit of improvement can have a big impact on your ability to manage productive conflict. Which in turn will help you grow a healthy organization and ensure forward motion.

So what conversations are you avoiding and why do you think you’re avoiding them? Before entering a difficult conversation, can you recenter yourself around what you need the other person to achieve? And what can you do today to practice reframing difficult conversations in terms of outcomes? Thanks so much for joining me. Please subscribe, comment, and share with a friend if you liked it. Send thoughts and questions to contact@pdlpodcast.com and we’ll address a few towards the end of this season. Join me next time where I’ll talk about the problem of getting too fixated on a single solution path.