Master Debriefs Like an Expedition Leader
I always marveled at the unflappable focus one of my mentors brought to expedition debriefs. The first time or two I was on edge as I shared one issue after another. Some I thought I should have planned for prior to departure. Others came out of nowhere. Still, I wondered. When is he going to get frustrated?
Instead, he calmly addressed each detail, showing the same interest in highlights and problems. He’d spent too many years in the field to know that getting worked up over a debrief wasn’t worth anyone’s time or energy. (Unless, of course, someone hadn’t shared information along the way, but we’ll get to that.)
These were learning sessions. Time for us to find strengths and weaknesses. To grow in our understanding of the environment, local connections, partnerships, and how it all fit together for our operations. This way, the next time through, we’d be that much more educated, resilient, and able to provide a better expedition experience. Our business would grow.
In one of my favorite books, Principles, Ray Dalio, founder of the world’s largest hedge fund, emphasizes the importance of systematic reflection as a key to continuous improvement. We’ll get into exactly how it plays into his process for growth and success, and how it matches elements of expedition debriefs.
First, we have to agree on one key principle:
If you can’t confront reality, even when it’s uncomfortable, you’re only deluding yourself. You’ll never grow. And your operation or company, or product will fail.
The key is to focus on learning rather than blaming. Accept the facts of any situation without letting emotions distort them. If you can’t, it’s just your ego talking. This is the first step in effective reflection because it creates a clear, objective foundation for learning.
It can be painful. But pain usually signals that something is wrong and, therefore, can be improved. Instead of avoiding these experiences, reflect on what caused them and how they can be avoided in the future.
Dalio even says “Pain + Reflection = Progress.
A good boss or mentor will appreciate your honesty.
Seems rational, right?
Agreed?
WHAT IS A DEBRIEF?
A debrief is more than a postmortem of what went wrong or right in a project. It’s a structured discussion designed to extract lessons from the recent past and transform them into actionable insights for future endeavors. A 2021 study published in the Journal of Applied Psychology found that teams that engaged in regular debriefs experienced a 20-25% improvement in performance metrics compared to teams that did not debrief as consistently.
With that in mind, let’s dig in.
Elements of an Effective Debrief
A well-structured debrief includes four key elements that support learning and growth:
Timeliness: Debriefs should take place as soon as possible after a project ends. Fresh memories yield more detailed insights, while delayed conversations risk fading recollections or lost lessons.
Inclusivity: Everyone involved in the project should participate. This includes not only core team members but also stakeholders who may have an external perspective. Diverse voices provide a fuller picture of the project’s dynamics.
Open Communication: Encouraging team members to speak openly about both successes and failures is crucial. A debrief that focuses too heavily on what went wrong may miss critical learning opportunities from the successes achieved. Leaders should ask open-ended questions such as, “What did we do well that we should repeat?” alongside “What could we improve next time?”
Actionable Insights: Finally, a good debrief concludes with a clear set of actions for the future. This could include improving processes, adopting new tools, or adjusting team dynamics. These insights should be documented and revisited before the next project to ensure that lessons are applied.
The Ideal Mindset: Reflection, Ownership, and Growth
Effective debriefs start with the right mindset. Research shows that the way employees approach the debrief has a direct impact on their ability to turn feedback into growth. According to a 2022 study from the Harvard Business School, employees who adopt a learning mindset—seeking growth from the process rather than focusing on personal validation—gain more long-term benefits from feedback. When employees view feedback as a tool for self-improvement rather than a critique, they are more likely to internalize the lessons and improve performance .
This mindset shift requires psychological safety—a concept explored by Amy Edmondson of Harvard Business School. When employees feel safe to voice their opinions and admit mistakes, they are more likely to engage deeply in debrief discussions, contributing to a richer analysis of the project. Leaders can foster this environment by emphasizing that the purpose of the debrief is collective learning and development, rather than individual blame.
HOW TO TURN DEBRIEFS INTO A GROWTH AND LEADERSHIP TOOL
1. CREATE FEEDBACK LOOPS
Poor leaders operate in a vacuum (or echo chamber). In order to fully understand the situation and the opportunities to succeed, leaders must constantly seek feedback from others, especially from people with key experience or roles who see things differently from themselves.
In the field, an expedition leader will often daily gather feedback from their team, whose members showcase an array of specializations, backgrounds, and experiences. The last thing a leader wants is to be surprised to learn after the fact about an issue that could have been addressed or something that a team member felt uncomfortable bringing up that could have changed the trajectory of the expedition.
What Dalio calls “thoughtful disagreements” can easily turn into outright arguments if not managed properly, especially in dire circumstances. As we mentioned above, leave your ego at the dock. Don’t take feedback personally, but rather use it as valuable information for improvement.
These feedback loops also present opportunities for you to reflect and uncover patterns in your decision-making and performance.
TRIANGULATE YOUR INFORMATION
I like Dalio’s use of the word “triangulating” your view by consulting people with different perspectives, especially those who may know more than you. This way you avoid blind spots and ensure that your reflections are grounded in diverse insights. In expeditions, this will include soliciting feedback from different team members, ship departments, local contacts, and partners so that you can put together the most objective view of the situation to then work from.
Do you go to the same person or group for feedback all the time? These painful situations have a way of bringing out your natural biases and limitations. Reflecting with the input of others will help you recognize these blind spots and make more informed decisions.
This can be uncomfortable for some, which highlights the importance of creating a safe space and company culture that values innovation and the acceptance of failure as a learning tool. Reflection requires radical honesty, both in how you assess yourself and in how you communicate with others. This involves being open about weaknesses, mistakes, and areas where you need to improve.
If you’re reflecting within a team or organization, encourage a culture where people can openly share their thoughts without fear of judgment. This allows for more honest and effective reflection and growth.
2. CLEARLY DOCUMENT REFLECTIONS AND LEARNINGS
From the days of ship’s logs, captain’s logs, expedition journals, to today’s technology, explorers understand the value of tools to both capture and share reflections. Similarly, Dalio advocates for documenting lessons learned during reflection.
This allows you to track patterns, identify recurring issues, and develop principles that guide future decisions. Certain companies will create their own tools to record decisions and outcomes, which are then analyzed for patterns.
Over time, you’ll be able to extract general principles or lessons that can be applied to new situations. This practice makes reflection a systematic part of your growth process.
3. USE TOOLS TO BOOST AND SHARE REFLECTION
Instead of working from an information dump or raw information, continuously track the outcomes of your decisions and the actions you take. Compare them against your goals to see where adjustments are necessary. Use data and analytics to support your reflections, ensuring you’re making objective observations.
Then remember: takeaways that are tucked away don’t do you or your team any good. Create a system (digital or manual) to track the outcomes of your decisions and actions over time. Ensure that the system/platform/information is easily accessible by everyone who could learn from it, and that it is consulted regularly.
This is crucial in overcoming institutional knowledge loss when key employees move on.
4. STAY HUMBLE AND OPEN TO LEARNING OVER THE LONG HAUL
The key here is to embrace reflection as a continuous habit, using insights to improve over time. Arrogance can stop people from reflecting properly because it makes them believe they already know everything, but this process is never-ending. Even after decades of experience, you should continue to reflect on decisions and remain open to learning.
Commit to reflecting after every significant event, no matter how much experience you’ve accumulated, and remain open to learning new lessons from each experience.
By following these steps, you can turn reflection into a systematic process that drives personal and professional growth.
Now, lastly, let’s turn the debrief around on ourselves as leaders. How can we grow through regular debriefs?
Debriefing as a Leadership Tool
For leaders, debriefs offer a critical opportunity to assess not only the performance of their teams but also their own effectiveness. Just as important as evaluating the outcomes of the project is assessing the leadership strategies that guided it. Were there moments when decisions could have been made differently? Did the team receive the support they needed?
Leaders should be prepared to model the vulnerability and openness that they expect from their teams. Sharing personal reflections on leadership choices during a debrief can foster an environment where all participants feel empowered to share their own insights.
For more on leadership, check out my favorite books.
