Leadership & Development from the Trailhead - How managing people on the trail equates to People & Projects in Business
- Jeremy Oyen
- Apr 22
- 5 min read

As I am preparing for the upcoming season of outdoor adventures and mentorship opportunities, I reviewed an article that I have included in field guide trainings for years and started thinking about how it could apply when looking at the way people and business leaders navigate theirs and their teams’ work.
In Paul Nicolazzo’s Site Management® – The Missing Link article he delves into the process of management of risk during outdoor programs through the process of site management. Nicolazzo defines site management as a “continuous process that begins when the students arrive and ends when they leave. It occurs in the present tense.” As I was reading this, I thought about how I have taken and adventure based model and applied it to other aspects of leadership and mentoring and a light bulb flashed. If we reframed the definition to match that of people leadership, project management and team development becomes … “The continuous process of leadership and collaboration that begins when employees come together to work towards a common objective. It begins when the project launches and ends when it is complete.” You could also expand this to start when an employee is hired (by you) and ends when they move on (to another assignment, role, or company).
The area that really became intriguing for me was equating one’s leadership modeling or style to the way that Guides position themselves on the trail to provide the most supportive environment for their group. The Guide’s approach needs to include factors such as risk management; opportunities for instruction, assessment, team building; and being able to do the activity without assistance.
Below we will look at a number of examples of “Instructor Positioning” examples and share what it might look like in the working world.
Here are some assumptions we will make for these examples:
The project (trail) has already been defined.
Objectives and milestones are known
Your role is to set up the team, identify the ones accountable and assist them on their journey.
We have 2 guides in each scenario for field risk management purposes. You may be guiding solo, and you will have to adapt.
For illustrative purposes, group movement in the examples shown below is left to right, and the colored dots represent the Guide (in red) and the team (in blue).
Example 1: Far Lead / Far Lead

This is an approach where you (the guide) are positioning yourself well ahead of your group. They are safely moving along a well established trail, but you need to get ahead to scout for possible risks/hazards that they might encounter and you want to be fully prepared to help them navigate the challenge.
In a business setting this approach would be used when the team fully understands and are capable of executing on their individual and group assignments, but the project leader(s) know that there are some items that might need to be cleared prior to the group getting to the stage of work when they meet that obstacle. These obstacles can vary greatly and only with strong planning and identification of dependencies on systems or other teams can a leader know that situations like this are coming and get out ahead of the work to assess and plan for the hazard.
Example 2: Lead / Lead

This model is great when you know the trail, your experience indicates that there are no known hazards ahead, but you need to be in front to manage the team’s progress just in case something unexpected arises.
Consideration for this approach is similar to the Far Lead / Far Lead but is more applicable when the risks or uncertainties are minimal. You are there to keep the group going and direct them around issues that arise.
In both examples 1 & 2 you are in charge. Your team is doing what you are asking of them. There is less individual autonomy here due to potential risks or hazards that you feel would disrupt or danger the project.
Example 3: Middle / Middle

Here is where you are starting to shift from an approach where you need to be in-front to one where the group is starting to take “point”!
Middle / Middle is an excellent way for you to build group relationships and create a different dynamic with your team. In this approach the group is completely and fully capable to take charge, managing the work, and run the project with minimal supervision. You are still there as needed, but empowerment and ownership is growing.
Example 4: Sweep / Sweep

Just picture it, you’ve launched the project, assigned tasks and accountability, and you are able to work with your team to execute the project under their direction. In this approach, you do not see or know of any hazards or issues that would stop the progress or put any of the work at an undue risk. Effectively you are allowing your team to showcase their talents a bit more, and are right behind them when they do encounter something they may not have expected (but you did).
Example 5: Flanking

In examples 1-4 there has been a linear path being followed, think of it like hiking along a single-track trail in the mountains. When the trail is less defined, like on an ocean or other large open spaces, team members may spread out. Working on different tasks can take people in varied directions, while still working towards a common goal or location. In situations like this, you are at your most active. You need to be aware of where each member of your team is, what direction they are going (what they are working on) and when appropriate you may have to nudge them away from a hazard to ensure their safety and bring them back to the group.
This can be one of the best examples of where things can either go amazingly well, or really get off the rails. To employ a “flanking” leadership approach, everyone needs to have a full understanding of the group’s objective, their accountability, and the empowerment that has been given to themselves. Work is matrixed. There is great independence and autonomy, but only to the point where it helps the entire group.
Leadership (Guide) positioning is critical when working with teams. The manner in which you work with, protect, facilitate, and empower your team tells them exactly how you feel about them and their work. If you always are in the Lead/Lead, you are indicating to the team that they need to simply follow you. There is no inspiration or call to action for them to lead, which means they are limited in their growth to specifically what you ask and tell them what to do.
When you are able to shift your team members forward along the path, you are letting them know you believe in them, their abilities, and their insights. You are pushing them to achieve success. You are giving them the opportunity to grow. They may stumble along the way, but you are there to lift them up, stabilize the situation, and continue.
There will always be times when you do need to lead from the front, but the more that we can lead from the middle or flank our teams, the better off we all will be.
“Chase Your Adventure” in leadership by facilitating other’s growth.
It is not our part to remove all hazards everyone will encounter. It is our hope to provide the structure and opportunities to identify hazards, learn how to manage them, and conquer them – together!
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