How to Have Tough Conversations With Team Members, with Brett Gilliland

This episode is a solo cast, where I have an opportunity to share something that is of value to you as a business owner in a seven-figure business. I have a bit of a cold I have been battling but I wanted to still move forward with this episode because it’s critical. Many of the businesses we serve in our community right now are dealing with some of these challenges that I’m going to talk about. I want to do this for them but also for any of you who I’m sure have dealt with or are dealing with similar challenges.

These challenges that I’m talking about have to do with having difficult conversations or tough conversations. It’s in a team member context. I’m going to talk about how to have conversations with team members. You can apply some of what I teach to any conversation that you are having that may be a little challenging for you.

Demands And Challenges Of A Business Owner

Before we dive into the topic, I want to step back and acknowledge, as I often do, that life as a business owner is very demanding and challenging. It’s no wonder that most businesses fail within the first 5 years and only 3% to 5% of businesses that ever start to make it to $1 million or more in revenue, which is why, as you have read what I talk about on this show before. It’s why we call you elite entrepreneurs. That is the name of our business but it’s a description of who you are.

As seven-figure business owners, you are elite. Not many businesses make it. You have all of that weight on your shoulders. If you have made it to $1 million or you are fast approaching that mark, you have got this growing team. You have learned how to get and serve customers with your product or service in a consistent manner. It doesn’t mean it’s always right where you’d like it to be but you have learned how to generate leads, get customers, fulfill your product or service in a consistent way and you have gotten to that $1 million mark.

You are not winging it and you have figured out enough about marketing and sales and fulfillment that you have. You have had a steady operation. Now you are moving into new territory where the name of the game is figuring out how to scale a team, how to grow an organization, and build capabilities in your company that allow you to move further past the place where you are at.

Anyway, that weight on your shoulders is constant. I feel it. As a business owner, I know what you are going through. It can affect your sleep. It does mine. Ever since becoming a business owner, there’s not a night that I don’t at least have some thoughts about the business as I’m trying to go to sleep or more commonly, that I wake up in the middle of the night, what I have affectionately started to call halftime. About halfway through the night, I wake up. If things are happening in the business that has my mind spinning, that might be the end of my sleep for that night. Poor sleep affects health, as I’m demonstrating now with my poor health.

That’s very real for business owners and I know it personally. It can affect your relationships. It certainly affects finances in some cases or many cases. More broadly, it affects you having the time that you want to do other things. In a word, that’s freedom. You start the business because you want freedom but often, the business consumes you. You no longer have the freedom or even the hope of freedom that you once thought was going to happen when you started this business.

That’s the backdrop. That’s the spot we are coming from. One of the things that weigh on you constantly, as the business owner, has to do with your team members. You might call them employees. I like to refer to them as team members but you substitute that word for employees if that’s the word you use in your mind. Whether or not you consciously do it, all of us subconsciously are either more confident, at peace, and happy about the state of our team.

If we are confident that we have the right team members and they are all doing good work or we have some concerns worked out that are playing through our mind, our subconscious all the time. If we have like a weak link or maybe one spot in the team or a couple of team members where you are not quite sure that you are getting quite the full horsepower that you would like to get there. Maybe they are great performers but they don’t fit in with the team very well. Maybe there are some poison sorts of effects that a team member or two has on the others.

That waves on you as the business owner. When you have that going on, your overall confidence in the business goes down and you show up differently. You show up differently with the rest of the team, with your customers, partners, or everyone when you don’t have full confidence that you are going on all cylinders. You are humming along because you have got all the right team members pulling in the same direction.

Having Tough Conversations: If you have a weak link, that weighs on you as the business owner. When you have that going on, your overall confidence in the business goes down, and you show up differently.

Tough Conversations

There are two types of tough conversations. I’m oversimplifying. There are lots of varieties probably but these are the two we are going to talk about. The first is a performance issue. You know somebody has a responsibility that they are not either capable of delivering consistently or they are capable but for some reason, their performance is dropped off. That’s a performance-related type of tough conversation.

The other difficult conversation that we need to have sometimes is around the fit with the values or the way that they interact with team members or customers. You might think about it as attitude sometimes, but the way that their behavior and attitude affect others. Those are the two types. One is more performance related and one is around what I will call values fit. In both cases, you might be reticent to have a difficult conversation because you don’t want to create more work for yourself.

Let me be more clear on that. What do I mean? If you have somebody in a seat now and they are performing something or doing something. They are taking some of the load off of you. Some of the collective load of the business is on their shoulders and that’s nice. Somebody is doing something but if they are not doing as much as they could be doing or should be doing, then we have a problem.

We ought to make some adjustments there. Either help them get where they need to be or move them into a different role or move them out altogether and get somebody else who can perform that role at a higher level. We are afraid to have that conversation because we are already strapped for time. We are already running like crazy. We can’t imagine a world where going down a person, even if it’s like half a person from a productivity standpoint. That feels overwhelming who’s going to fill that in? You or another team member.

How are you going to cover that? Finding somebody always takes time and it’s hard to get them up to speed once they are on board. We start to settle for what is instead of taking the necessary action to move the performance of the business up by improving a spot or two on the team that needs some help. That’s the reason and I have been through this myself as a business owner. I have watched it more times than I can count with businesses that we have served. We all know there’s a better answer out there but then we talk ourselves out of it because we want to avoid the pain of dealing with the problem.

Let’s move into what we do. Let’s acknowledge or assume we have all had this problem. Maybe now, we have team members who either aren’t pulling their full weight. In other words, they can’t consistently or aren’t consistently meeting the performance standards of the role or they are a high performer, but some of their attitude and behavior is toxic in your work environment and affects others in a negative way. What do we do to have these difficult conversations?

Mindset Ideas

I’m going to start by giving you some mindsets. Some ways of thinking about this can trip us up or the flip side of that. Ways of thinking about it that might help you prepare for and have these difficult conversations. The first thing I want to say is and this might be intuitive if you have given it some thought, but most of us don’t ever say this out loud.

I’m going to invite you to not only think about this but maybe even just say it to yourself. People behave completely logically to how the world is occurring to them. In other words, what they do makes perfect sense to them, given how the world around them is occurring to them. You might say, “For some people, that’s irrational thinking.” Whether you think it’s rational or irrational. Everybody acts in a situation in the perfect way. The precise way that makes the most sense to them, given the circumstances.

If we were facing a life-threatening situation, let’s say we are out in the forest hiking and we come upon a bear. Our first actions are going to make perfect sense to us. Now, they might not be the best actions but to that person and how that situation is occurring. They are going to take the next best step in their mind. It could be completely wrong but it is the right one in their mind. I’m no bear encounter expert, so I’m not even going to try to tell you what should be done in that situation.

Let’s say the right answer was to drop dead and play completely still. Don’t move. Another response and the total opposite end of that spectrum might be to run for your life. Whether the person took either path, it made the perfect sense to them in that situation. That’s the point I’m trying to make. If you see somebody doing something strange in your business, one of your team members does something and then you are like, “Where did they come up with that?”

Remember that people do what makes perfect sense to them given how the world occurs to them. We need to be curious. The other mindset I want you to adopt is people want to do well. Even if there are rare exceptions out there, let’s say there isn’t such a thing as bad apples in people. Somehow, they made their way into your company. You selected them, chose them, and hired them but somehow, you picked somebody that didn’t want to do well.

For the most part, you will do better off if you view people as wanting to do well. The vast majority of people, especially if they made it through your hiring process. They don’t wake up on Monday morning aspiring to go to work and be mediocre. If they don’t show up and say, “I think I’m going to do a so-so job today. That’s what I aspire to.”

Most people, especially the ones that made it through your hiring process, want to do well. They are coming from a good place, but then they are also acting in the world as if they are doing the thing that makes perfect sense to them, given the circumstances. Those are two important mindsets that I invite you to adopt those filters as you prepare for and have these difficult conversations.

Another mindset thing that I want you to try on is if it isn’t working for you as a business owner, it probably isn’t working for them as well. There’s no world where they are perfectly fine and happy. They feel like they are thriving and you feel like they are flailing. Flailing and thriving are two different occurrences. It’s possible, but in most cases, if you don’t feel like it’s working. They probably are feeling that way as well.

My fourth mindset idea here is if we are not careful, we can easily become accomplices. What do I mean by that? In most legal systems, certainly this way here in the US. If you have knowledge of criminal activity and you fail to take appropriate action, then you become an accomplice to that crime. Think about that. It doesn’t matter how you got it. Somehow you got knowledge that, let’s say, your brother-in-law or sister-in-law was doing something shady and you decided not to take appropriate action.

You knew about it and you didn’t take appropriate action. You now become an accomplice to that crime or those crimes depending on what we are talking about. In a similar way, if you fail to have difficult conversations with your team members, you become an accomplice to the crime happening in your business. Who are the witnesses of those crimes? Probably more appropriately here, who are the victims of those crimes?

Often, it’s other team members. It’s customers or maybe partners. You or your family. Everyone that you love becomes a victim of the crimes happening in your business for whatever reason you don’t feel equipped or you are afraid of the repercussions if you have those conversations. Sometimes, we allow ourselves to become accomplices to the crime.

Many of you know I spent several years in leadership positions at a company called Infusionsoft. A great company and a tremendous experience for me. I wouldn’t be where I am now without that time, my association with Clate Mask, the CEO of that company, and many other great leaders. One of the investments that Clate made was to take ten of us leaders at the senior leadership team of the company to go see Jim Collins in his lab in Boulder, Colorado, for two half-day sessions. It was amazing. It was one of the most transformational professional experiences of my life. It was awesome.

One of the nuggets and I took away many nuggets from those two half-day sessions with Jim Collins, but one of the things I took away was this quote. It says, “Spending time on or with B-players, anyone other than an A-player who’s killing it from a performance standpoint, who fits the team well. Spending time on or with B-players is taking time away from the people and the things that you love.”

Think about that for a minute. Any amount of cycles, brain time, thinking time, extra work to compensate for a poor performer, and team member conversations to smooth things over when that person bowls through the office like a bowl in the China shop. Whatever your circumstance, you have to spend a lot of time and energy working on those circumstances and those situations with the people involved.

You may even go home and talk about it with your spouse. Everything is affected by that person’s behavior or lack of performance. You don’t want to spend time on B-players. You want to have every seat in your company filled with somebody who’s going to consistently meet the performance expectations and who will be a great fit on the team. When that’s not happening, you are hurting the people you love and the things that you love to do.

At the end of the day, the struggling team member isn’t thriving in the situation. That person, he or she deserves to work somewhere where they fit well and they can perform at a high level. You want that for everyone. The mindset needs to be when I don’t take care of the problem, one person might be creating or presenting in my company, and everyone else suffers.

Some of you are like, “I have known this person for a long time or they have been super loyal to me as we have grown the business.” There are all these reasons why we don’t want to have a hard conversation. While they are all valid and they are perfectly valid reasons. You are hurting the rest of the team. You are hurting the customer experience, partners, your own family, your own loved ones, and your significant others.

The Framework: Intent, Behavior, Impact

All of those people are suffering by allowing 1 or 2 or however many difficult conversations that are left unset. Those are some of the mindset things. Let’s go now to the framework. I want to give you some practical ways of looking at and working through these tough conversations. First of all, I have already talked about this but there’s a little beach ball framework that might help you and others understand how the world occurs differently to different people.

If you can imagine in your mind if you have ever been to the beach and had one of those big inflatable beach balls. Most of the ones I have seen have these bright colors on them. They are striped. You see a segment that’s red, white, blue, or yellow. All these bright colors, not like stripes but segments of the ball. If you throw the ball up and have it spinning and we stop the ball from spinning. We hold it between two or more people. You might see a blue stripe in part of a red one. The person on the other side of you might see a yellow one. A third person would see a different perspective of that ball.

Your framing as you go into these conversations. It even helps to bring that beach ball concept to your conversation with the person you are talking about, acknowledging that, “We are likely going to see some things differently in this conversation but I want to have an important conversation with you. We need to understand how we are both seeing so we can figure out the best to move forward.”

The second framework, there are three pieces to it. The first is intent, the second is behavior and the third is impact. I will talk through each of those. If I’m sitting down with somebody, let’s use a values fit for example. Let’s say we have value in our company of we genuinely care. It doesn’t matter if we are dealing with each other, our customers, potential customers, or clients. Whoever we are working with, we genuinely care. That’s our value but you see some behavior in a team member that doesn’t reflect that.

Maybe they say things that are condescending or insulting to their coworkers. You might sit the person down and say, “I want to have a conversation with you. I’m not sure what your intent is but I’m going to share a behavior that I saw and the impact. I want to start with an assumption that you have good intent. I have known you for a while now. You are a good person. I don’t think you are a bad person. I’m trying to figure out the intent but I’m going to assume positive intent to start the conversation.”

“I’m going to explain the behavior I saw. You were talking with Johnny and I heard you say this phrase to him, then I saw this impact in Johnny. Here’s the impact that I observed in Johnny. Maybe even Johnny came and said something to you later or Johnny said something to another team member about it. There was an impact for Johnny that most reasonable people would acknowledge.”

You can go back and say, “I believe you have positive intent. I don’t think that you intended to hurt Johnny but we have this value here called we genuinely care. That moment that I observed doesn’t appear to fit that value to me. Can you help me understand what was going on for you during that time?” Your job now is you move to listening. Your job is to withhold judgment. You need to keep the emotion out of it as much as possible. You are trying to stay in a very curious place. Try and understand the facts.

The person says, “You are right. I have never wanted to hurt Johnny. For the past couple of weeks, I have learned that my father is taken ill. It doesn’t look good. I have been losing a lot of sleep over it. I’m just generally more cranky with everyone than I usually am.” I’m not saying that’s a good excuse but you might be surprised at how quickly they acknowledge their role and say, “You are right. I shouldn’t have done that. Here are some circumstances that might help you be more aware.” You can say, “I’m sorry to hear that’s happening with your father. Sorry to hear you are losing sleep over it. I appreciate that you are acknowledging that that’s out of bounds in our culture and our values. We don’t allow for that behavior. How can I help you? What can I do to help your situation?”

Maybe there are ways you can be flexible in their work schedule for the next week or two or make sure that they are getting the help they need to see a doctor if they need help with sleep. Whatever it is, you can transition to helping them make a change. I gave it an easy example but what if they say, “That’s Johnny’s fault. He deserved every word that I said.” You can go right back to, “You know that one of our values is we genuinely care. One of the ways that we demonstrate that is in the way that we talk with each other. We are always respectful to one another. We care about the other person’s interests. Those words you used with Johnny are out of line with our values.”

“Now you can move to a conversation about how we are going to make an adjustment to that behavior or how they are going to have to go somewhere else where that type of conversation is more acceptable. It doesn’t work here in our team or our culture.” You keep it very matter-of-fact and very behavior-based. You are not using generalities. You are talking specifically about things that they have done or said and the impact that it has on others, including the impact that it has on the overall team’s well-being and culture, and environment. All of that is appropriate.

Having Tough Conversations: Don’t use generalities. Talk specifically about things that they’ve done or said and the impact that it has on others, including the impact it has on the overall team’s wellbeing, culture, and environment.

Let’s move to a performance example now since I started with the values one. For the performance example, let’s say you are talking with somebody who has an expectation of, we will call it, ten units a week. I’m not talking about a sales rep, service rep, or anything. Makeup whatever role it is. Let’s say the expectation is ten. For a long time, they were always at ten. Let’s say for years they were at ten or maybe they are a new employee and the expectation for the start was ten.

They hit it a few times, then they started dropping off. Now it’s eight. Sometimes 9 and sometimes drops to 7 but never at 10 over the past couple of months. Maybe you can’t even afford to wait two months to have this conversation. When it’s consistently dropped below the standard, now it’s time to have the conversation.

You go in the same thing. Not judging. The numbers are the judge, the performance expectations. If you have made those clear, you don’t have to be judged. You get to be coached. You get to go in and say, “Sally, we both know the expectation is ten. It’s always been ten. Since the start of your owning this important role in our company, the expectation has been ten. Other people in that same role consistently hit ten. You even hit ten consistently for a while. Maybe a long time and now your performance has dropped off. We consistently see eight. Sometimes we see nine. Sometimes an occasional 7, but the standard is 10 and you are below the standard. Let’s talk about it.”

This is all very objective. The standard is the judge and you get to be a coach. I’m going back to intent, behavior, and impact. I’m going to assume positive intent. I think you want to do a good job. You have always done a good job for us in the past, or we hired you because we both believe this was going to work well for you. I don’t think you want to come in here and do mediocre work. I’m not coming from that place. You start with that intent, then you go to behavior.

If the behavior is, I see you coming in early, staying late, working it hard and I still don’t see the result. That’s one conversation. Let’s talk about why that is but likely, in many instances, the result’s not happening because the right behaviors aren’t there. You can say, “I see you strolling in at 9:00 and you are one of the first ones gone. I see you spending maybe too much time texting people or on social media.”

Whatever the case is, you can start weaving in some of the behavioral things you are observing, then you can talk about the impact. What I have noticed is when you spend time doing those things, you run out of time for the key activities that allow you to hit the standard performance of ten. That’s the impact. When you don’t do that, here’s how it affects the rest of the team or the rest of the company, or here’s how it affects our customers. You are trying to lay out the impact of their behavior.

I hope that both of those examples, whether it’s a value fit example or a performance example, help you see how you can keep this cool. You don’t have to be super judgmental. It doesn’t have to be emotional in any way. You can be a very supportive leader. Go to them and say, “I’m assuming positive intent. You are coming from a good place. I wouldn’t have hired you otherwise. Here are some of the things I’m seeing, the behavior, and the impact I’m seeing.”

Intent, behavior, and impact. You can have conversations with them, remembering the beach ball. You are seeing the blue side, the red, and all along the way on intent. Maybe you are seeing the intent wrong and they can help clarify the intent so you can see it similarly. Maybe you are seeing the behaviors differently than them. You can both share. Maybe they are seeing something different in the behavior than you are.

On the impact side, maybe they are not seeing it the same as you, but you can have a beachball conversation around intent, behavior, and impact, whether it’s values or attitude. That’s how we team and show up with others that we work with, versus the performance one where they have certain expectations as they own an important role in your company and have responsibilities that must be delivered week in and week out.

In both those cases, it matters and affects you as the business owner. It affects every single person on the team. When you don’t have these tough conversations, everyone on the team is looking at the problem child. The one person that’s where the problem is. They are going, “Why is the business owner ignoring that? I guess I don’t have to worry about performance.” Their standard of excellence around performance starts to drop or they continue to hold themselves up as a high standard of performance until they get tired of trying to pull everything themselves and go to your competitor. They go somewhere else where their talents can be utilized in a team environment where they feel like everyone is an A-player.

The Improvement Plan

You do not want to alienate your best people. The quickest way to do that is to ignore problems and not have these tough conversations. The last thing you need to do after you figure out how to have that beachball conversation around intent, behavior, and impact is the improvement plan for moving forward. You need to leave with a specific agreement as to how their behavior will change. It needs to be over a specified period. Don’t leave it open-ended.

A nice rule of thumb for me is 30 days with weekly check-ins. If it’s behavior that needs daily follow-up, then do a daily follow-up. If it needs weekly official follow-up, then do weekly. For most things, I’m not talking about high-intensity or high-impact things. I’m saying we have the next month to work on this but we are going to have weekly check-ins. That’s a nice rule of thumb.

The specific agreement is how the behavior will change, then the timeframe that you have agreed to. Here’s a tip for best practice. Have that person be the one to summarize your conversation because we are still doing the beach ball the whole way. You believe that the two of you had the same conversation but it probably occurred differently to them. What you want them to do is write you an email summarizing what you discussed and what you agreed to for the next steps. That way, they have to put their occurrence, view of the volleyball down in writing and email it to you.

You can read it and go, “I didn’t quite see it that way,” and make some adjustments and send it back to them or call them back in and say, “You said this. I was seeing it this way,” but there’s an opportunity for clarification right up front. Now you have got an agreement that you are both on board with. You can use that same agreement the next week when you check in or the next day if it’s a daily thing. You have your way forward.

Those are my tips for how to have difficult conversations. I urge you to have them. They are hurting you more than you know. They are hurting people you love. That may sound dramatic but it is the truth if something in your business isn’t right. Think about your body. If some part of your body isn’t well, you can’t perform at your highest level. If something is holding you back and until you get it right, nothing is whole or complete.

Your company is the same thing. It’s like a body and there are all these parts. Every team member plays an important role. When one is off, everybody suffers. You have got to get it right. Do it sooner than later. Even if it means losing that high performer, the right team members will step up. They will see you made the hard decision and they will come and thank you. 1) They will say, “I can’t believe it took you so long.” 2) “Thank you for doing that. Now everything is much better. We can move forward.” If they are not as hard to replace as you think they are, if you have to let somebody go, the right team members will thank you. They will rally around that decision and help you move forward.

I hope you found a lot of value in some of the framing and the tools to help you have these tough conversations with team members. You can’t afford to have people who don’t fit in your team or people who are no longer performing at a level they need to perform. I hope that you will keep reading the future episodes and keep bringing you tons of value and content for seven-figure business owners who are trying to scale.

Important Links

• Infusionsoft