11 Leadership Lessons I Learned From Hiking With My Kids

Javid Jamae
Jun 27, 2016 · 8 min read

A few years ago, after moving to the Bay Area, my wife and I decided to take the kids out hiking more. At first, my four younger kids would whine and ask, “do we have to go?” After a few months of taking them regularly on the weekends, the whining evolved into, “OK, fine! Which trail are we going to and how many miles?” We considered that success.

Despite the fact that they still don’t claim that it’s their favorite activity, once we’re on the trail, they usually enjoy the experience. We discovered that hiking is not only great exercise, and really good for the brain, but it’s also a fantastic way to learn about leadership.

Deciding who is the trail leader (the person that walks in front of the group) always turns in to an interesting debate with my kids. While mediating and coaching my kids about leading the group in hiking, I started realizing that I was teaching them lessons in general leadership. Here are eleven lessons we learned and how they might apply to business leadership.

The leader isn’t merely the person in the front

Initially, my twins (our youngest) would complain the most about not being to be the leader as much as their older brothers. As the complaining increased, my justifications for not letting them be in the lead as much had to evolve. I started explained to them that the leader isn’t merely the person in lead. The leader is in the front so that they can serve the group by observing things before the others. The leader has to know where the group is going, what the group should watch out for, how fast the group can go, and much more.

The general leadership lesson: If you’re in a leadership position, don’t expect to be looked up to because of your title. Having the title of “boss” or “manager” doesn’t make you a leader. Leadership is an important job that requires responsibility, skill, empathy, and communication. Expect to be looked up to because you’re good at those things.

Leaders must keep an eye out for danger

Living in northern California, there are many thing you have to watch out for on the trails. Some trails have steep cliffs that the kids could easily fall of of. Depending on the trail, there are also animals like mountain lions and rattlesnakes that we have to watch out for. Trails that are “dog friendly” mean that there is a higher probability that an unleashed dog might scare one of our kids who is more fearful of dogs. There are also poison oak and poison ivy that we need to be able to identify and avoid. When we let one of the kids take the lead, we make it clear that they have to be cautious, look out for dangers.

The general leadership lesson: A good leader should think through the different risks that the group may not have thought about or encountered yet and bring those risks (and possible solutions) to the teams’ attention.

Leaders must communicate dangers

Sometimes the trail leader will see a cliff or a low branch, but won’t think to let the others know. Sometimes they will have run too far ahead to where we can’t hear them, or so that they’re vulnerable if they encounter a wild animal. We’ve worked hard to make sure that they not only remain cautious and look for danger, but also clearly communicate the danger to the rest of the group.

The general leadership lesson: A good leader should make enough time to have conversations about risks and issues with the team. When they do have those discussions, they should communicate in a clear and effective manner.

Leaders have to set and be mindful of the pace

The trail leader isn’t just responsible for watching out for danger, they are also responsible for maintaining the pace for the rest of the group. They have to be aware and respectful of whether someone is tired or hurt and has to walk slower. They also have to make sure to wait in case someone wants to stop to observe something. If the leader goes too far ahead, then they can’t know if anybody in the group needs to slow down, and the group starts to get frustrated or nervous about the leader not being nearby.

The general leadership lesson: A leader should be present to lead. A leader should also have a realistic understand of how fast their team can deliver so that things don’t take too long, on one hand, and so the team doesn’t get burned out, on the other hand.

Leaders must be aware of the rules and of others

The trail leader must make sure that the group’s pace is appropriate based on the trail conditions, and the group is following the trail rules.

If the trail is crowded, we don’t want to run in to other people by going to fast and we don’t want to slow down other people if we’re going too slow. If the trail is wet, or steep, we don’t want to risk slipping and getting injured if we’re going too fast.

Many trails have rules. Some trails post signs asking that you stay on the trail for restoration / preservation purposes. Some trails post signs asking you to keep quiet to not disturb the local wildlife. Some trails ask that dogs are kept on leashes. The leader must make sure that their actions and the actions of the team are in line with the expectations of the posted signage.

The general leadership lesson: The leader must make sure that the team’s actions abide by the etiquette and ethics of industry and markets you operate within.

Leaders need a mentor

Because our younger twins still had a lot to learn about being in the lead, when it was their turn, it helped that my wife or I took the lead with one of them to help talk them through the responsibilities. We showed them what poison ivy looks like, what to do if they see a mountain lion (DON’T RUN, shout and flail your arms, step backwards very slowly to rejoin with an adult, make yourself look as big as possible by lifting your arms or holding your jacket open, let an adult put you on their shoulders if you’re smaller). We taught them to keep the pace, not run ahead, and communicate danger. Working with them to not getting distracted is still a work in progress, but that also comes with age.

The general leadership lesson: If you’re in a leadership position, seek out the help of someone who is more experienced than you are. They can help you think through things that you’ve never encountered before and may not know how to respond to properly.

Followers can be leaders too

Being the trail leader is a highly sought after position in our family. When they’re upset about not being in the lead, I often try to console the kids by telling them that there is a “back of the line” leader. It’s usually not enough to quell their feelings of frustration, but it’s still an important lesson. Followers can still look and listen for dangers and they can still warn others. They don’t set the pace directly, but if the leader is mindful of the followers pace, the followers can influence the pace. The follower can also let the leader and others know if they’re going too fast.

The general leadership lesson: Because leadership is a set of responsibilities, and not a title, leadership qualities can be demonstrated by anybody, even if they’re not officially in a managerial or leadership position.

Fear of being undermined puts the group at greater risk

Sibling rivalry and paranoia are hard things to shake. Sometimes, when one of the kids becomes leader, one or more of the other kids tries to pass them or threatens to pass them. This causes the leader to start running to keep the lead, thereby throwing all caution to the wind. All leadership responsibilities are forgotten, and the leader spends most of their time looking back to make sure that nobody else is trying to pass them. Similarly, when the leader is arguing and fighting with one of the other kids, they can’t do their job.

The general leadership lesson: When a leader is engaged in or worried about internal team politics, for good reason or not, the team will have less leadership and will be at greater risk.

Undermining the leader puts the group at greater risk

Related to the last scenario, if one of the followers is trying to run past the leader they are not only undermining the leader’s ability to do his or her job, but they also can’t display good leadership or followership responsibilities themselves. And, if one of the followers is arguing with or teasing the leader, neither the leader nor the follower can fulfill their roles, and the entire group is at greater risk.

The general leadership lesson: When a follower is undermining the team’s leadership, for good reason or not, the team will have less leadership and will be at greater risk.

Leaders tend to do better in pairs

One thing we learned over the course of many hikes is that when two of my kids would take the lead together, there was typically less conflict and higher quality leadership. The leaders didn’t generally run too far ahead, because the pair would talk and keep each other entertained. There was less jealousy about who was in the lead because there was one less kid to complain about not being in the lead. There was also less resistance when we’d ask the leading team to let someone else lead because they had each other. Sometimes, they’d get so engaged in discussion that they’d forget to communicate with the rest of the group, but I think that their attention to detail and responsibility will improve with age.

The general leadership lesson: Leadership can be lonely. Sometimes a leader should enlist another team member to help them. They don’t always have to have the same job. For example, in my profession as a software developer, development teams often have a manager and “technical team lead”.

Experienced leaders are necessary for dangerous trails

Sometimes we explore new trails. When we don’t know what’s around the corner, we often find it extremely stressful to let one of the younger kids take the lead. Because they’re more excited about the new challenge, they are more likely to run ahead fast, they are less likely to observe a cliff, and they don’t communicate dangers. We’ve found it best to create a rule where an adult, and adult/kid pair, or my oldest son can be in the lead when we’re on a new trail. This causes less stress, less debate, and more observance of good trail leadership.

The general leadership lesson: When you’re in uncharted territory, you should elect to have a more experienced leader who is more attentive to identifying risks and who is better at communicating with the team to come up with solutions.


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Javid Jamae

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CEO / Founder @ Skipcard