March 16, 2022

Leading Through Difficult Conversations

Leading Through Difficult Conversations



Quick poll: who loves having difficult, but necessary, conversations? Anyone? No one?

That’s what I thought. It’s not easy to stand up for yourself. It’s especially not easy to tell someone you report to that you disagree with them. While having difficult conversations in the workplace might be your least favorite thing of all time, it doesn’t negate the great value of having them. Let’s use the example of Neelix in the Star Trek Voyager episode Rise, to talk through how to have these types of talks. Equipped with thehowmay be just what you need to push through and do what needs to be done.



Right out of the gate, I want to say that Neelix did not have his difficult conversation in the best possible way. He heads out on a mission, assigned to Tuvok’s team, and over and over again they butt heads. “I can’t seem to please him,” Neelix laments to The Doctor.


As things continue to go wrong, Neelix and Tuvok disagree on just about everything. Neelix pushes. Tuvok is unmovable. They continue to clash until Neelix can’t take it anymore and explodes, unloading years of pent-up frustration on Tuvok! He’s tired of being ignored and treated poorly. While Neelix did not handle the conversation well, he DID HAVE IT. And that puts him ahead of a lot of people. The harsh reality is that probably upwards of 97% of all difficult conversations that need to happen…never do. I want to say that again.Most difficult conversations that need to happen, never do.And that is a crime.

The conversations aren’t easy, but everyone benefits from them. Beyond that, there is also a negative impact to holding truths in that need to be said. We just saw this with Neelix’s explosion! When we bottle it all up inside it impacts our mood, work ethic, ability to collaborate with others, and more. When they need to be said and need to be heard, the conversation needs to happen. So if you remember nothing else from this blog please remember this: go have that difficult conversation you’ve been needing to have! But finish reading first, so I can tell you how. 



Step 1: Identify that the conversation needs to happen.

Difficult conversations can be a lot of things. They happen at work and in our personal lives. These are conversations where you may have news to deliver that the other person doesn’t want to hear. Or when you need to let a coworker know that something went wrong. Or, like Neelix, when a relationship needs attention. These conversations can come from anyone, but there is often additional anxiety when the conversation needs to go up the org chart. The first thing we can do isleverage emotional intelligence as a guide for the conversationand managing anxiety. Here’s a quick review of emotional intelligence. (I go into more detail on emotional intelligence in a few other episodes. Listen to TOS: A Private Little War and ENT: The Catwalk for more.) There are 5 dimensions of emotional intelligence:

  • Self-Awareness
  • Self-Regulation
  • Motivation
  • Empathy
  • Social Skills

These all play a role in having an effective, difficult conversation. Now that we have our foundation, let’s look at the structure of having the conversation.



Step 2: Prepare

In my experience, many people don’t consider this step and it is critical. You must prepare! John Wooden, the legendary UCLA basketball coach, says, “Failing to prepare is preparing to fail.” And that absolutely applies to a difficult conversation. You need to think about what you are going to say and evenhowyou are going to say it. Almost more importantly, you need to (here’s that emotional intelligence piece) be aware of the emotions you have around this topic. From there, you can practice self-regulation with your emotions.

A difficult conversation almost always has emotion surrounding it, but the focus of the conversation shouldn’t be driven by those emotions. Your feelings need to be expressed and acknowledged, but you also need to root your conversation in facts and observations.

Let’s say I want to have a conversation with you about the way you always make cracks about my receding hairline (yes, this is from a true story in my current role). If I don’t think through my approach and consequently I’m not aware of my emotions or have the chance to self-regulate, then I’m likely to come at you like, “Dude!!! Knock it off! You’re a jerk and I hate it when you tell me how much bigger my forehead is since our last meeting!” You’re probably not going to be open to more discussion or hearing me out. You’re going to get defensive and not feel very good about anything that happens next.

Did I, technically, have the conversation? Yes. Was it productive for anyone? Definitely not. Instead, I can take some time to prepare and reach out to you ahead of time to tell you I’d like to talk about some observations I have concerning jokes made at my expense and how they’ve made me feel. This way our meeting has the potential to be effective. I’ll be able to present my side in a way you are much more likely to hear. “I want to talk with you because I’ve noticed that every time we meet, you make a joke about my hairline. I don’t like that and it doesn’t feel good when you say those things.” You’re open to hearing what I have to say and we can proceed in a productive manner.



Step 3: Notify the other person

You’ll notice I said I let the person know that I wanted to talk to them ahead of time. This is another step that is often missed. You can’t just drop a difficult topic on someone out of the blue and expect them to be able to engage in it well. Giving them some notice can give them the time needed to prepare themselves, as you are preparing yourself, for a tough talk.

One-sided preparation may result in a one-sided conversation.In jobs where people are represented by a union, they have what are called Weingarten Rights (at least in the United States). If an interaction could result in discipline or termination, the employee has the right to have a union steward present. So we were required to give advance notice for these conversations.

In a previous position I held, people were union represented. We were required to do this, and we did. But we did it the wrong way! Earlier, I gave the example of saying, “I’d like to talk about some observations I have concerning jokes made at my expense and how they’ve made me feel.” Being specific and clear about the topic of the conversation gives the other person time, as well as a context, to prepare for. In the union job, we offered a stock message “We’re going to meet and you can have a steward there.” Period. All that did was heighten anxiety and immediately make the person defensive. Nothing good comes from that. So let the person know when and why the conversation is coming.



Step 4: Neutralize power differential in the meeting place

Where and how you meet matters too. Ideally, you want to meet in person, or as in-person as possible. I count video conferencing as being in-person, but only when both people have their cameras on.

When you meet, you want to eliminate or diffuse any power differential. Instead of meeting in your office, you may want to meet in a neutral space like a coffee shop or a conference room where you’re both comfortable. Work to match eye levels. Don’t stand while they sit or vice-versa. Don’t sit in a cushy chair pushed up super high. Sit as equally as possible. If you’re meeting virtually, I recommend blurring your background or having shared backgrounds. This reduces opportunities for distractions or perceptions of power differential.



Step 5: Set Ground Rules

Now there are some much more intense conversations than jokes about my hairline that I know you are thinking about that need to happen. Poor job performance, dishonesty, maybe even outright harassment, discrimination, or racism. Once you have prepared, notified them, and identified a neutral place to meet, it’s a good idea to establish some ground rules. This accomplishes two important things: First, it offers the rules of engagement. When the conversation has clearly articulated parameters, it lessens anxiety and sets everyone up for success. Second, it gives you an immediate win – an agreement! The ideal goal of a difficult conversation is a shared, agreed-upon solution or set of next steps. So coming up with ground rules sets the tone of seeking agreement.


Ok! You did it! The conversation is happening! You start with the statement that you worked on when you were preparing. From there, you want to share factual, objective statements. The two phrases that help me the most are“I have observed/noticed…” and “That makes me feel…” Don’t be accusatory. Instead of saying “You did this terrible thing!” you would say, “I have observed you doing ________ and it made me feel _______.” This keeps the discussion focused on facts and also acknowledges emotions while avoiding words that attack. Then listen. Listen openly and without judgment. This is where you apply empathy and social skills to the other dimensions of emotional intelligence you’re already utilizing. 



Step 6: Agree on the next steps

In most cases, the discussion shouldn’t be about proving you are right and they are wrong. (In cases of discrimination or harassment, proof may be a vital part of the conversation) The ideal outcome of this type of conversation is a shared agreement. Agree on a solution as well as the next steps. Once you’ve achieved that, congratulations, you’ve had a successful, difficult conversation! But it doesn’t end there.



Step 7: Follow up

The final step to this process is following up to be sure that both of you are staying true to your agreement. These follow-ups should be agreed upon in the conversation. So thank them for the conversation and then offer a follow-up approach. Here’s one example, “Thank you for your time. I appreciate it and am glad we were able to come to this agreement. I’d like to follow up and would like you to do the same, to be sure we both do what we’ve agreed to. How about next Tuesday we connect for 15 minutes for a quick check-in?”  



To summarize, there are 7 steps to leading a successful, difficult conversation:

  1. Identify
  2. Prepare
  3. Notify
  4. Neutralize power differential
  5. Set ground rules
  6. Agree on next steps
  7. Follow-Up


Remember our "buddy" Neelix? With our newfound skills, let’s see how he did with his difficult conversation.


Neelix wants a friendly relationship with Tuvok. He also wants to be recognized as a peer and a professional. In a high-intensity moment, with years of pent-up emotion, Neelix shouts,

You’re going to listen to me!

This is what often occurs in that 97% of difficult conversations that don’t happen. The feelings build up and then result in an explosion.



You are emotionally distraught. I’m tired of being the target of your contempt.

Not great, but understandable. When stepping through the structure of a difficult conversation I talked about two things that apply here: being objective and not being judgmental. Neelix missed the mark on both. Tuvok tried to do the right thing and put this conversation off until Neelix had a chance to collect his thoughts, prepare, and have a meaningful discussion. But because Neelix was one of the 97% for so long, the volcano started erupting and there was no stopping it! 



“I have no feelings towards Mr. Neelix.”

This is better! Neelix was listening and was able to articulate his point based on what Tuvok said.

“You made it obvious you had no respect for me.”

This is well stated. He’s still accusing Tuvok, but he is describing his feelings in a way that opens the door to real discussion and understanding. Until that is, he starts accusing again…



“You don’t have any instincts, no gut feelings.”

Any time you want to use a “you” statement, try to flip it into an “I” statement. He could have said, “I’ve noticed you don’t follow your instincts. I’ve seen that you dismiss gut feelings. Here’s why I think that’s bad.” You see, he’s saying the same things but in a way that invites Tuvok to listen instead of defending his actions.



“I disagree. FINE!”

And I would too. If Neelix came at me, warp 9.97 with shields up and torpedoes loaded, I’d disagree too and be ready to double-down on everything I had done.

Kudos to Neelix for at least having the conversation. But, because he didn’t follow the steps above, the conversation didn’t result in a shared agreement. He should have prepared, notified Tuvok of the discussion in a neutral place, and then set up ground rules. From there, they could have an objective discussion leading to an agreement. The conversation would have looked so different.

Instead, they both had to nearly die and then come through for each other in extravagant ways to find any common ground. Let’s learn from their mistakes and do better. Be one of the few who not only have those difficult conversations but lead them well!