Over the years, I worked with and led hundreds of people. Some were staff, others volunteers, and some were my superiors.

I remember working with a highly talented young man. His talent was matched only by his lack of interpersonal relationship awareness. 

He did great work, but he wreaked havoc with volunteers and the rest of the team. 

I struggled with how to help him. I wish I had used these five rules a the time. I would have had a better chance to have kept him on the team. 

1. Confront the issue head-on and in person

Whether it’s a board member not performing their role or a volunteer that seems to miss appointments or not do what they’ve committed to, don’t wait to discuss it with them. The more time that goes by, the more tension builds. And more damage is done to the overall morale of your team.

And while I know, it’s not always possible to meet with everyone one-on-one, this should be the general rule of thumb. Things tend to spiral quickly when you result in firing off an email in a moment of deep frustration or even anger. 

Looking someone in the eyes brings out a level of compassion, making the conversation softer and more likely to result in a positive outcome.

2. Avoid exaggeration

It’s easy to exaggerate when we’re frustrated. But in all likelihood, “that person” is probably not always late, always divisive, or always lazy. They’re probably not unfriendly or rude to everyone on the team.

Starting a sentence with “you always...” is a trap you should avoid. You’ve lost the objective stance, and you have given the other person a reason to say, “that’s not true.” 

It’s important to be realistic and truthful when addressing whatever behavior makes things difficult. This will allow you (and them) to honestly explore what causes or prevents the behavior and provide powerful insights for everyone.

3. Use specific examples

If you’re anything like me, you don’t particularly like conflict. When addressing these difficult situations, the temptation for me is to keep it vague, not to hurt feelings.

I might be tempted to say, “I really appreciate you and the different ways you’ve contributed to the organization, but I just don’t feel like you’re ‘all in’ anymore.” 

There are a few problems with this kind of generic feedback. First, you don’t give them anything specific they can do to show you they’re “all in.” And secondly, they can come back with, “oh, you must be reading the situation wrong, I actually am all in.”

Instead, describe precisely what has led you to this conclusion:

• On Sunday, when you showed up 15 minutes late with no notice and things got missed, I felt like you no longer cared about this team or this organization.
• Two months ago, you agreed to help me recruit several new donors to help us reach our goal, and you haven’t recruited a single one which makes me feel as if you’re not really “all in.”

The goal is to have a productive and fruitful conversation and not necessarily elicit a defensive argument.

4. Listen well

State your specific concerns or objections, and then give them a chance to talk. Most of us are not only uncomfortable with these difficult conversations, but we’re also uncomfortable with silence. For that reason, we tend to talk and talk and talk some more. I get it. However, often these difficult conversations have been nothing more than a misunderstanding. And even if not, the only way to fully explore the issues and find a resolution is to have all of the information on the table and look at it objectively. Make your statements and observations, and then allow them to speak into those. There’s likely something that you will learn from them as well.

5. End with a specific plan

Difficult situations rarely, if ever, fix themselves. And even simply addressing the negative behavior or patterns is rarely effective enough. There needs to be a plan.

- What specifically do you need to see from this board member moving forward?

- How can this volunteer gain your trust again?

- What benchmarks does this staff member need to achieve to prove they deserve their role?

The plan should be specific and measurable, and a follow-up meeting to review their performance should be scheduled in the near future where honest feedback can be given.

I know first-hand that these sorts of meetings aren’t easy. Often, as a team leader or an organization, you want to sit back and hope the situation corrects itself, they get a different job, or God miraculously transforms their negative patterns overnight. But that is rarely the case. 

Suppose there’s any hope of saving the relationship, the morale of the team and keeping the mission moving forward with this person coming along. In that case, it will require a lot of intentionality and a few uncomfortable conversations to get there.

At the end of the day (in my experience), it’s all worth it. The situation doesn’t always get turned around. Sometimes a board member is asked to resign, a staff member is fired, or the volunteer leaves upset. But more times than not, progress is made, and the good work you’re doing is once again the main focus of your team and your time.