Working at a summer camp can be challenging, espe­cially if you’re in a year-round position and dealing with a difficult boss. It’s no secret that not all bosses are perfect, and that no industry is completely made up of incredible leaders. Fortunately, most folks in the camp industry would describe their bosses as understanding and respectful. And certainly empathy is paramount when working with the volume and age of individuals we see during the summer.

When spending ten months preparing for two, camp professionals have a relatively small window of opportuni­ty to execute a high-quality program. To run a safe, quality summer camp requires leadership. Camp is a high-perfor­mance environment, and with the intricacies of a camp operation, you may even have multiple bosses.

Friendships at camp can span years. Although friends who become supervisors can be supportive, that new re­lationship can also be awkward. You can’t necessarily talk to your boss like a friend and expect the same attitude in response. And it’s possible your boss might not even acknowledge that the relationship has changed.

Such lack of clarity can take their team on a roller­coaster ride, one that is nearly impossible to stay off of. Anxiety and the stress it creates can trickle all the way down to the campers.

Living where you work creates even further complexity. As a staff member you must learn when to be distant and when to be close. Living where you work can even mean that your boss is also your landlord.

Why You Need to Show Your Boss Grace

It’s impossible to think every person will be an incred­ible leader. Not all bosses are great. A whole industry complex exists based on teaching and enhancing boss­es’ leadership skills. This includes books, speakers, and podcasts that preach the principles of great leadership. Ultimately, a boss’s leadership comes down to their per­sonality and desire to be known as an outstanding leader.

A fantastic quote by relationship expert Dan Savage de­tails the meaning of his coined phrase, “the price of ad­mission.” Savage said, “There is no settling down without some settling for” (Savage, 2011). In every relationship, whether it’s with your boss or someone more intimate like your spouse, you will have a certain amount that you are willing to put up with to be with that person.

For instance, my wife is obsessed with Walt Disney World. It’s her “happy place.” While I enjoy seeing our kids happy during family trips there, the theme park would not be the first place I would choose to go. Re­turning to Disney World year after year is “the price of admission” I’m willing to pay to be with her.

No boss is perfect; it’s important to recognize that. And that’s OK if you know what you are willing to put up with. It’s also acceptable if your “price of admission” changes over time. When you are no longer willing to put up with something, it’s time to speak with your supervisor about a change. You don’t want to let it go until you find your­self in an adversarial or negative relationship with your supervisor.

Let’s review three principles we know about bosses:

  • are human.
  • will make mistakes.
  • develop along with their staff.

Some folks expect their boss to always be the ultimate authority. That’s just unrealistic. Try to show your supervi­sor the same grace that you would want to be shown in those moments when you fall short.

How Trust Plays into Your Relationship with Your Boss

Trust is fundamental to every relationship. While you may expect leaders to inspire such confidence, you must also own your role in that area. It is your responsibility to be a meaningful steward of trust, and it’s important that everyone — you and your supervisor(s) — foster this reliance and don’t just expect trust to be given in your direction.

Your first instinct with fostering a positive relationship is perhaps to become a friend. However, you can have a positive working relationship with a boss without doing this. In fact, friendship can actually cloud the power dy­namic with a boss, so the supervisor-employee dynamic needs to be respected. The power dynamic is a pathway to building trust with a supervisor who wants their au­thority and decision-making to be highly regarded.

With trust, you have more control than you may think. Demonstrating honesty, vulnerability, and consistency are all pathways by which you can build such trust — and following through on your words reminds a supervisor that you are trustworthy. While as a team member you might be tempted to remove all boundaries and be friends, that separation might actually help your boss form a sense of trust.

How to Increase Communication with Your Boss

Communication is a key component to creating trust. All of us have a deep fundamental need to be understood. It’s the reason that one of the greatest gifts you can give someone else is your time. However, from how a mes­sage is delivered to what is said and how it is interpreted, communication can fail in many ways.

In general, don’t listen just to respond. Sincerely listen to what is being said, process that information, and think before you speak. Unfortunately, the desire to share an opinion can sometimes result in making a statement before the other person has even finished talking.

The quickest way to learn how to communicate with your supervisor is to identify their communication style. Several personality and communication tests are available (Myers-Briggs Type Indicator, DiSC assessment, emotional intelligence assessments, StrengthsFinder). While these tools are effective, the easiest thing to do is just ask. Your boss might feel they communicate completely differently than someone else would assume. Also, you may find that the way your boss likes to communicate is different from your preferred communication style.

Dan Pink, in his book To Sell Is Human, wrote, “They teach us how to answer but not how to ask” (2013). While some folks in the camp industry might not want to think of communication as sales, it is important to remember that you need to ask questions to learn how to communicate most effectively with your boss. Sell yourself as the conscientious team member you are.

The proverb “We were given two ears and one mouth for a reason” reinforces this message. Asking questions of someone shows that you care about and respect them.

Communication is often muddled by the tools we use. Email, text, and phone etiquette often need to be taught. When communicating with your boss, don’t forget to express gratitude, and be concise in the details you share. Also be clear about your call to action. What are you asking of your boss? Do they need to answer a question, RSVP to a meeting, or something else? It’s important to repeat the requested action at the end.

Keep in mind, there is a high likelihood that your boss will not hear some part of your message — but you will surely leave an impression. Maya Angelo says it well: “At the end of the day people won’t remember what you say or did, they will remember how you made them feel.”

Know, too, that everyone wants a different frequency of communication. Some folks want check-ins to happen daily, while some are content with weekly or even monthly updates.

How to Problem Solve with Your Boss

Especially in the camp industry, high performers are expected to solve problems. It’s one of the most valuable skills you can bring to your team. However, problem-solving can also cause friction with your boss.

When working with people of all ages, leaders require emotional intelligence. However, bringing emotion into the process can get in the way of problem solving. Not every boss will respond well when someone is obviously upset. While emotions are linked to everything, it is important to know that emotions can also distract bosses from seeking solutions to issues.

Timing is everything when problem solving. Know that your priority on any given day may be different from your supervisor’s. Teams function best when they respect each other’s time. Slowing down the decision-making process will often lead to better decisions. The steps — stop and think, gather facts, and brainstorm solutions — need to be spelled out all the way through the process.

A proactive mindset will allow for a productive conversation with your boss. You can use the PROACT acronym to aid in your decisions (Hammond, Keeney, & Raiffa, 2015):

  • PRoblem — State the problem.
  • Object — Figure out your objective in solving the problem.
  • Alternatives — What are your alternatives (i.e., potential solutions) for solving the problem?
  • Consequences — Think through the consequences of those alternatives.
  • Tradeoffs — Additionally, think about any tradeoffs to your potential solutions.

This thought process can help whether you and your boss are making a decision together or if a larger team is taking part in that process.

Keep in mind that your supervisor may well rely on you to be honest about your opinions. If your supervisor doesn’t know or understand your position, they likely won’t consider it.

Wrapping up

To find empathy, remember that bosses are human and not always perfect. Trust is a fundamental building block that allows clear communication and problem solving to happen. And when in doubt, ask for advice from a mentor.

Photo courtesy of Brave Trails, San Diego, CA


Hammond, J. S., Keeney, R. L., & Raiffa, H. (2015). Smart choices: A practical guide to making better decisions. Boston, MA: Harvard Business Review Press.

Pink, D. H. (2013). To sell is human: The surprising truth about moving others. New York, NY: Riverhead Books.

Savage, D. (2011, August 21). The price of admission. YouTube.

With over 20 years of experience developing overnight and day camps, Dan Weir is the senior consultant at Immersive1st. He can be reached at