The Top Three Things Overland Summers Looks for in a Summer Trip Leader, And How to Win the Job

Spending the summer outdoors with kids and teens on a hiking or backpacking trip is a dream job for many people. But how do you win one of these coveted positions at a summer adventure camp?

Over the course of 40 years, Overland Summers has hired close to 5,000 summer trip leaders. Here are the top three qualifications to be a trip leader for Overland:

  1. The Right Motivation
  2. The Right Experience
  3. The Right Temperament

You have to want to spend the summer leading kids and teens! Any other motivation just won’t cut it. For example these two motivations are fine, but they’re not the right motivation to lead a teen adventure trip: “I love the outdoors!” or “I can’t wait to see the Rockies!” Make sure you understand the right reasons to be a summer trip leader.

Overland wants to see that you are an exceptional leader— so we want to know: what have you led? Are you, or have you been, a sports team captain? Are you, or were you, the president of your student government? Do you run a campus organization, club, or team?

Overland’s summer trip leaders are unflappable. They are patient. They are thoughtful. They are well-organized and planful. They think two or three steps ahead, and they see the interconnectedness of their decisions: We call it playing 3-D chess.

You’ve thought it through, considered your motivation, experience, and temperament: are you ready to apply? If you are, then read on for tips on how to win your dream job as an outdoor trip leader for Overland.

Here are three Insider Tips to win your dream job as a summer hiking trip leader for Overland:

  1. Careful Preparation
  2. On-point Interviewing
  3. Prompt Follow Up
  • Read the Overland website (thoroughly!). What strikes you as most important?
  • Know the mission, the history, the leadership, and the staff. Be prepared to ask good questions.
  • Network to Find current and former leaders. Learn from these people.
  • Draft, revise, and polish your application. To get past the first screen in the Overland leader hiring process, your application has to show you care, that you pay attention to details, and that you’re highly motivated.
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How To Choose A Summer Adventure For Your Child

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Insider Tip #2: On-point Interviewing

If your application is picked by the Overland leader hiring team as a semi-finalist, you’ll get a chance to Zoom with an Overland staff member. Keep these ten Zoom Interview essentials in mind:

  1. Choose an appropriate setting. Don’t interview in a coffee shop! Don’t interview outdoors! Instead, sit at a clutter-free desk in a quiet room.
  2. Make sure the lighting, camera, and sound are good. Don’t wing it: test everything to make sure you’ll look– and sound– your best.
  3. Dress appropriately. Don’t overdo it (no need for a suit and tie!), but, on the other hand, a T-shirt is too casual. Strike the right balance!
  4. Be on time. Better yet, be early. Sign in to the Zoom five minutes before the appointed time.
  5. Don’t have food or drinks. This is an easy one (and, for the duration of your interview, don’t pick up your water bottle).
  6. Listen carefully. And, if you don’t understand something–especially if it’s a question, then just ask!
  7. Answer thoughtfully (and appropriately). Take your time, think it through, and do not –absolutely not– use any kind of off-color language.
  8. Be concise, on-point, and honest. This is not the time for you to indulge yourself with long, or off-point stories.
  9. Be prepared to ask three good questions. Another easy one: have these prepared ahead of time — and make sure they’re good.
  10. Thank your interviewers for their time and consideration. Take the time at the end to thank your interviewers. It’s easy. And appreciated.

Throughout the interview be yourself, relax, smile, be thoughtful, and have fun. Because that’s what we want all of our Overland leaders to do when they’re in the field leading kids and teens on a summer adventure trip.

Insider Tip #3: Prompt Follow Up

After your interview, send a followup message letting your interviewers know you appreciated their time. Keep this message brief — a two or three sentence email will do — and make it specific to your interview by referencing something that was discussed during the interview.

  1. Consider Your Motivation, Experience, and Temperament. Are you right this job?
  2. Follow our top three Insider Tips and you will have the best chance of leading for Overland. And be sure to check out this sneak peek of what it’s like to lead a trip in the Sierra Nevada.


    Tom Costley

    When Tom Costley founded Overland in 1984, he sought to create experiences for young people that were fun, where new friendships could grow, where natural beauty was embraced, where there were real and varied challenges, and where Overland’s students would achieve something of importance to them. Overland’s focus on small groups, carefully crafted trips, and superlative leadership has made it a leader in the summer camp world. Overland’s commitment to excellence in everything it does has led to its success: over the past four decades, Overland has served 40,000 students and 5,000 trip leaders. Tom writes about the outdoors and travel from Williamstown, Massachusetts.

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