Can We Talk? Difficult Management Conversations

Scott Arizala
November 2019

“Can I talk to you for a minute?” It’s a simple question that in the blink of an eye can send the receiver on an emotional roller coaster. Take a moment and slowly read the following list. Pretend each one of these people is asking you that question. Notice your initial emotional reaction.

  • Boss (Oh man, I’m in trouble. I’m probably getting fired!)
  • Significant other (What did I do/not do/miss/say/not say . . .)
  • Work friend (What are you going to ask me to do that you didn’t do or don’t want to do?)
  • Nonwork friend (What’s wrong? Who’s sick? What’s the drama?)

The list could go on, and your reactions might have been different than mine, but I’ll bet we share some of the same feelings. Most people’s reactions are generally negative, laced with the prospect of unwanted consequences, the assumption of difficult work, and the like. Maybe there is someone on the preceding list (or from some other important category) to whom you don’t have a negative reaction when they ask for your time and attention. It’s worth taking a minute to think about that person and why you don’t react the same way. More than likely, it’s not just because you have a wholly different relationship with that individual, but because your experience with them tells you that when they ask you for some time to talk, it could be any number of things, not just the bad stuff. They have desensitized you to that particular question by sharing, asking about, and engaging with you on a variety of topics. All relationships are built on communication, and you have learned over time that engaging with this person is easy. You get them, they seem open to you, they react in ways that you would expect, and they really listen to what you have to say.

So how can we be that kind of effective communicator to the staff we supervise? While we will undoubtedly have negative things to say and many difficult management conversations, it is far easier to have those conversations couched in a generally positive relationship than in one in which they feel dread from the moment you open your mouth.

To that end, before we can even talk about the mechanics of a difficult management conversation, we have to work on creating positive relationships with the people we supervise in an environment where feedback is welcomed, expected, and asked for. The scope of that is considerable, but consider these four key components:

  • Be a role model. To create a culture of feedback, you need to show your team how. It’s not natural, and where we get the most experience with feedback is at school and in our jobs. School tends to be competitive, and most job “performance reviews” aren’t exactly positive, growth oriented, or inherently motivating. So you need to ask for help, giving your staff firsthand experience working with you not just for you. You need to ask for feedback, and, when it’s critical, do something differently. It doesn’t have to be huge or drastic, but it does need to be measurable and relevant so people notice.
  • Be approachable. You are their boss and leader. How they feel about coming to you for anything will have a direct impact on how they feel about you approaching them. You want people to feel taken care of, listened to, and validated when they come to you. Notice I didn’t say “right.” If your staff feel good about coming to you, it’ll be easier for them to trust you, which will lead to more effective conversations if you need to correct something they are doing.
  • Be accessible. None of this works unless you are around — and not in the way many camp directors are. Speed walking intensely through the middle of camp with a stern look on your face and a bunch of stuff in your hands doesn’t count. Slow down and put your things in a backpack. It is way easier to stop and talk or engage with someone who looks relaxed and interruptible. Everyone has a job to do, and yours may frequently take you out of the mix of camp. So it is important that you find time and space to be available.
  • Practice clear communication. Finally, feedback is essentially about not meeting, meeting, or exceeding expectations. That demands that you are clear about what those expectations are and when they start to change. We generally are not as clear with our staff as we think we are. Spend a ton of time talking in small groups and one-on-one, if possible, about what your expectations are for their jobs and various responsibilities. If you can add a discussion point about what they expect from you, then you are creating the foundation for effective difficult conversations.

With all that as a backdrop, there are essentially three parts to any difficult management conversation. There’s the prep work, the actual dialogue, and the follow-up.

Prep Work

For most conversations you have, there will be some time to prepare. That could be the handful of moments it takes to get someone’s attention and redirect what they were about to do all the way through to the hours or days it might take to gather necessary information and find the right time. Mostly, that will depend on the reason for the conversation and the urgency with which you want this person to do something differently. The following are some things to think about while you are prepping for a difficult conversation:

  • What do they think their job, role, or responsibility is or was in the context of this issue? You may not know the answer, but it will help if you think back to how you talked about this issue and how you specifically told them (or didn’t tell them) what your expectations were.
  • Have you given them critical feedback before? If so, what happened? Did someone else on your leadership team do this? What happened with them? Again, you may not have answers to these questions, but if you do, they might inform what you are going to do or say during this conversation.
  • What do you think they need to be more successful? If your knee-jerk reaction to this question is, “Just do the work,” “Just be with the campers,” or “Stop doing X altogether,” you may need to ask for some help from someone else on your leadership team or get advice from a trusted source outside of camp. You might be too wrapped up in the situation to get enough perspective to be helpful.
  • How do you want this interaction to be an example for how this person should handle difficult conversations with campers? No matter what the behavior, most of us would answer that question with words like “compassion,” “understanding,” and “patience.” We don’t want kids to “get away” with whatever, but we also want to focus more on the learning and less on the consequences. The same goes for staff.

The Conversation

The last few minutes of getting to wherever you are having this difficult conversation (away from others at camp, with someone else from your leadership team, and where interruptions won’t occur) may have been awkward. Don’t extend this awkwardness with small talk. Just calmly state the facts. Easier said than done, but the quicker you get to your version of the issue, the sooner you can relieve the added pressure of it being awkward. Remember, what you know is just a result of your direct experience or what someone else has told you — neither of which means you have the whole story or understand everyone’s perspectives. Circumstances and other “facts” can always change the story. More than a list of bad choices or things they didn’t do, each point should be clearly expressed in terms of the negative impact it had or could have on others. For example, most overnight camps have a curfew for adult staff. If someone is out past curfew, the potential negative consequences range from being too tired the next day to campers being left unsupervised at night. Maybe nothing actually happened, but the fact that they could have happened is reason enough to change the behavior.

Careful Listening

Engage in careful listening. Listen for comprehension and ask questions to help clarify that understanding. This is really hard. Most people listen to respond. However, waiting for a pause (or just interrupting) to try and ramp up your “argument” as a reaction to what you are hearing is not careful — and maybe not even really listening. Careful listening is actually harder during difficult management conversations, because the nature of what you are listening to is either defensive and excuse laden or paints a picture entirely different from yours. When the individual’s response is defensive, it typically lacks accountability. When it changes the story, so to speak, you can lose a sense of direction and goals for the conversation. Hang in there, ask good follow-up questions, paraphrase what you are hearing, take notes (if appropriate), and assume the person in front of you is coming from a good place and is a good person.

Yes, and . . .

It’s time to pivot. Because you listened carefully, you are now in a position to take the conversation where it needs to go. It’s OK if it needs to end now so you can investigate further or even just digest their reaction. You have come to the crucial “yes, and” moment where you can circle back around to the behavior that needs to change or stop. Improv actors will recognize that phrase as an acting technique. The idea is that on stage, during improv, you never stop a story from unfolding; you simply add to it and allow it to grow. The same can happen during hard conversations.

Let’s set the stage: When your staff member reacted to your assessment of their behavior and you carefully listened to what they had to say, you essentially heard, “I experienced it like this . . . .” Who are you to tell them otherwise? We do it to kids all the time (a child falls down and starts crying, and we say, “You’re OK!”), but it would be absurd if we did it to adults. Imagine seeing an adult trip and fall and get up crying, and then hearing someone say, “You’re OK!” Ridiculous, right? Well, trying to argue with an adult staff member, point for point, on why something they did was wrong is basically the same thing. They may have made a poor decision, but the reason they did is theirs, and you can’t take it away. However, that poor decision had a negative consequence regardless of the reason behind it. So, just say, “Yes, and X still happened, and that’s not OK. So, Y still needs to change.” This technique allows you to hold two conflicting truths at the same time and refocus on the needed change.

Steps for Change

“How are we going to make this change?”

Time to dive into the methods for change. Since you used the “yes, and” approach, you don’t have to argue about anything, just discuss how to fix it. If a person lack the skills, self-awareness, or critical thinking to develop new ideas in that moment, make sure you have come prepared with a few ideas you think will help them be successful. If they need it, offer some of your suggestions. This is like a dance. You can’t just step in and start doing some wild moves; you need to see how comfortable the individual is with the basics, and then you can offer new steps.

Did you notice the pronoun shift at the beginning of this section? It’s a subtle but important point to make. Your job as a supervisor is to be a resource to your staff, to help them deliver the best experience to campers, and to support their hard work. This includes helping your staff overcome challenges and poor decisions. When you say “we” as a framework for this part of the discussion, you are underscoring your responsibilities.

Striving for Change

The final step in every difficult management conversation is the trying phase. Obviously, this includes the staff member trying some of the new techniques or methods you just talked about to see if it fixes the problem or curbs the behavior, but it actually demands more:

  1. Understanding
  2. Structure
  3. Follow-up

The staff member must understand not only what to do differently, but why it is important. During the first part of the conversation and again during the “yes, and” step, you took the time to explain the negative consequences of their actions. The staff member may not agree with or like what you’ve said, but because you paid them and their ideas respect, they are far more likely to return that same respect. Don’t shortcut this part of the conversation. The individual needs to be able to connect the behavior or choice to the negative consequence on their own. It might not sound the way you want it to sound, but give them the space they need to process and discuss it with you.

By structure, I mean that you have to help your staff person think through how they will apply some of the methods you’ve discussed with them. Does the individual need to include others? Do they need additional resources? Should you be there to guide them or act as a role model? For example, if a staff member is always late for breakfast at an overnight camp or late for staff check-in at a day camp, just saying, “Be on time or early from here on out” isn’t helpful, even though it might be the behavior change you want to see. Leave the house earlier, wake up 15 minutes earlier, prepare for your day the night before, and buy an alarm clock that is not your phone might be some of the methods to achieve that change. Now put some structure and support around those methods.

“Wake up 15 minutes earlier” is easy enough to say, and, frankly, not that hard to do, but that is my old-responsible-
camp director-dad-self talking. Ask your staff. It’s pretty hard. So the structure around that might be one or more of the following:

  • Ask your co-counselors or roommates to also get up earlier to help.
  • Set additional alarms that you can’t snooze easily.
  • Set an “I have to leave in two minutes!” alarm or reminder.
  • Set up a special treat or reward for yourself, like a quiet cup of coffee before everyone else arrives.

Finally, you should set up a specific follow-up or check-in timeline. A lot of behavior that we are trying to correct through a difficult management conversation isn’t necessarily easy to correct. It may be based in other issues, poor habits, or routines that have turned into ruts. Each staff member is different, so the timelines vary, but everyone deserves a chance to actually change their behavior. If they don’t change, do they know what the consequences will be? Do you? Discuss it so there are no surprises moving forward. Would you fire someone for being late? Probably not. Would you fire someone for being late 26 mornings of a 55-day summer after multiple specific conversations about being on time? I’m guessing you probably would. When staff know the consequences to continued underperformance, they have more power and agency to change it.

During your check-in, ask about the specific methods, what is working, and where they may need more support or structure. Please remember that pit-of-your-stomach feeling “Can I talk to you for a minute?” can elicit. Your staff member has likely experienced it. Even worse, the foreboding feeling was warranted; they did do something wrong and are now in trouble. That nagging feeling often turns from the specific behavior to a more generalized feeling about their job and performance as a whole. They will inevitably walk away from this conversation feeling deflated and embarrassed. On some level, the individual may think that everything they do is subpar. Now is your opportunity to prove them wrong. Chance are, they are doing a lot (or at least a little) very well, and it is up to you to see it and then offer them genuine praise and recognition. They need it.

Scott Arizala is a leading expert, trainer, and consultant in summer camp. He is the CEO of The Camp Counselor, a consulting and training company, and the executive director of Chasing Summer, an organization dedicated to creating access for people with autism in recreation and education. He is a pioneering contributor to and project manager of Expert Online Training, a world leader in online training for camp staff. Scott is the author of the best-selling book, S’more Than Camp and contributing editor of Happiness, Diversity & Autism: Practical Strategies for Inclusion. Check out his website TheCampCounselor.com for more information.