Insurance Academy

6 Checkpoints Before You Have a Difficult Conversation

By Patrick Wraight | Academy Journal Blog | April 19, 2017

I’ve been on both sides of the desk, having a conversation that neither of us wanted to have. I’ve been the leader who needed to address an issue and I’ve been the person that has the issue that needs to be addressed. I’m not sure which side of the desk is worse but neither is very fun. At first, I thought that this would be a post for leaders, but as I read my outline I realized that these thoughts apply to both sides of the desk. Here are a few checkpoints to prepare yourself for those inevitable tough conversations.

Set clear expectations. Preparing yourself for these conversations starts at the beginning of your relationship with your team. Whether you are the leader or the team member, you need to be very clear about what you expect from someone else. How can you tell if you are performing well, unless you know the standard that you’re being judged against? You can’t. This isn’t only a leadership expectation. The team member needs to be clear about what they expect from their leaders also. How does your leader know if they are serving you well, unless they know what serving you looks like? They can’t. I would say that setting clear expectations across both sides of the desk is the most important step in avoiding those difficult conversations later. At the very least, it makes it so that no one is surprised if the conversation is needed. As personal finance author Dave Ramsey put it, “To be unclear is to be unkind.”

Set formal and informal checkpoints. It’s important to check in often to find out whether or not you’re on course. Try this. Wherever you are, (once you finish reading and commenting) get in your car and drive to Tropicana Field in St. Petersburg, Florida. Here’s the catch. Don’t check a map and turn your GPS off. No, don’t use that app on your phone, either. Someone is already thinking, no problem. I live in Clearwater and it’s easy to get to there from here. You’re the only one. The rest of us have to find St. Petersburg, let alone find Tropicana Field. Many of us will have to find Florida first. You get the point. If you just hop in the car and drive toward Florida, it’s going to be hard to figure out exactly where you need to be without looking at signs and using the GPS or a map. Just like on a drive, at work you need to be continually making sure that you’re going in the right direction. It takes frequent informal, stand up conversations that help everyone to see where the team is going and those short conversations at the desk to guide the team member in the right direction. You also need those formal conversations. You need to set aside 30 minutes to an hour (I recommend monthly) to review the metrics that tell you where you are compared to where you’re supposed to be and then to discuss the course corrections that will help you to get to where you’re supposed to be.

Say what you mean, not what makes you feel good. Here’s a tough one. If you let yourself wing it, you’ll end up saying things that you don’t mean because you didn’t take time to find out what you want to say. Take some time and prepare exactly what you need to say so that you’re not stumbling around trying to decide, or worse so you don’t try to make it up as you go. This goes back to clarity. If you have taken time to prepare for this meeting, it will help you to communicate clearly so that you can be as kind as possible. You preparation should include: exactly what the problem or issue is, time for your team member to address what they see as the root of the problem and to respond to all of your comments, time to discuss solutions and next steps, and some possible solutions and next steps. This needs to be a discussion. Today’s culture doesn’t allow for leaders to dictate solutions. If you want to reengage this team member, offering them a voice in the solution and the next steps will help you.

Say it when you need to, not when you want to. You’ve heard it said before and you’ve probably said it, too. Bad news is not like cheese. It doesn’t get better with age. Get this conversation over as quickly as possible. If there’s a behavior issue that needs to be addressed, all that waiting around creates toxic air in your team and you’ll be dealing with that for longer than you want to; much longer than if you had handled the behavior as soon as it came up. If someone needs a course correction, it’s easier to address when the correction is small, rather than six months from now when it becomes a major correction. There will always be other things to do. There will always be deadlines and projects that also need your attention. Your calendar will tell you that you don’t have time to have this conversation, but you know that the only possible time to have this conversation is immediately. Once you have the conversation, things can begin to heal and get better in the team.

Silence can be your friend. During your conversation, don’t feel the need to fill the air the whole time. Sometimes you have to make a statement and let it hang there. Like I’ll tell my sons, no is a complete sentence. If what you just said doesn’t need an explanation, don’t try to explain it. Just let it stand on its own. If your team member needs clarification, hopefully you’ve created an atmosphere of trust that will allow him to take in what you’re saying, chew on it, and ask questions or respond. When he finishes, let the silence sit for a minute. It isn’t necessary to respond that moment. Give yourself time to think through what you say next. Silence can be your friend.

Surrender your pride and be humble. This is a requirement for both sides of the desk. Tough conversations can become emotionally charged in a moment. It doesn’t take long for a reasonable person to blow up when they feel like they’ve been attacked. I can attest to what happens when you let the stress of a day get ahead of you and you take that stress into a tough conversation. I’ve gone into conversations with my pride on my sleeve and defended myself harshly when I didn’t need to. I’ve also had to go back to that manager and apologize for being angry, especially when there was no need to be. If you approach the conversation humbly, you can feel the sting of what’s been said and take it in the manner that it should be meant. Remember that your leader probably cares deeply for you, for the team, and for the company. That means that even though the conversation may sting, it is for everyone’s benefit.

These are just a few thoughts about making those conversations that you’re avoiding easier. We still don’t want to have them, and nothing is going to make it so that we look forward to them. Hopefully, you found something that will help you have that next conversation. Maybe you have some tips for us? Leave a comment with your thoughts.

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