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Where Have You Been?

Document Your Leadership Journey

“IF YOU DON’T KNOW where you’re going, any road will take you there.” I love this quote, not only because it’s supposed to get you moving if you’re stuck, but also because it screams, “Get organized, and have a plan!” This is great advice whether you’re planning a trip or your own leadership development. Any significant journey worth taking is worth planning. Let’s pretend you’re taking a six-month sabbatical to climb Mount Everest. You wouldn’t dream of tackling this adventure without a lot of planning, right? You also wouldn’t plan this trip without looking back at what you’ve learned from other high-peak ascents, both successful and unsuccessful. You’re going to need every bit of that experience to make this climb, so you better take stock of your lessons learned. The fact is that looking back can help you see the next adventure more clearly.

The same is true when it comes to planning the next step in your journey of leadership self-discovery. One of the first things you should do is reflect on where you’ve been as a leader. Are you doing this on a regular basis? Are you reflecting on your lessons learned? You should be; the leader who doesn’t learn from his or her mistakes is doomed to repeat them. What were the critical moments that shaped you as a manager? How did you react? What did you do well, and what could you have done better? How did others respond to you? When did you start to feel like a true leader? Most important, what did you learn from these moments?

Leadership is definitely a personal experience; the lessons you learn may be common ones, but the specifics of each situation make your leadership story unique. All of us can remember critical incidents that shaped us as leaders—times when we learned from a mistake or stepped up in a big way. Maybe it was standing up to a boss when you knew you were right. Maybe it was failing to pull the trigger on a bad hire or supporting an employee who turned out to be a star. Or maybe it was really listening to feedback and recognizing that you needed to change your leadership style.

Some lessons involve other people and can reveal patterns, such as failing to leverage peers or build relationships. Other lessons involve your own judgment—a fateful read of the strategy that leads to poor decisions or opportunities seized because you were willing to take a calculated risk. Your career is filled with times when you made the right call, did the right thing, or learned a difficult lesson. These are the touchstones of your life as a leader, the milestones along your leadership path. Your own leadership journey provides tremendous insight into how you should continue developing as a leader. In other words, where you’ve been can help clarify where you need to go. By reflecting on your lessons learned, you can build a development plan that optimizes your remaining growth areas.

Write Your Own Leadership Journey

There is an easy way to document your lessons and build your leadership story. Start with your first leadership role, when you first began to manage people. Write down the company, your job title, and the time frame you were in the role. Remember when you got your first direct report to manage? Were you excited about the opportunity? Maybe a little intimidated by the responsibility? You probably did several things right; but you might have made a few mistakes, too—first-time supervisors usually do. Think back to that job. What were the two or three most critical incidents that happened in that role, and what were the most profound learnings from those experiences? Write them down. Take the time to really think about the experience, but capture the essence of the lesson in a few simple words. Now, go on to your next role and repeat the process. At the end of this exercise, you should have traced your entire career as a leader and recorded your critical incidents and lessons learned along the way (see Figure 1).

Put your leadership story on a PowerPoint slide or practice telling it from memory. Share it with your boss, your peers, and your team. If you have a large organization, share it with your entire department in an all-hands meeting. Sharing your leadership journey allows you to model three powerful leadership tools at once: reflection, storytelling, and lifelong learning. Take your audience through your career, and tell the stories that have molded your leadership philosophy. Stories make your lessons come alive and cast you in a favorable light, as they generally involve you having learned from mistakes. Share your journey with pride—these are lessons that have had a profound impact on you, and sharing them candidly demonstrates that you’re open to learning from the lessons that lie ahead.

In my career, I’ve helped dozens of leaders create and present their leadership journeys, and the process has been beneficial every time. People love the framework because it helps them establish authenticity, which is critical for leaders. The process is particularly effective with leaders who have a reputation for being “hard to read” because the personal journey tends to showcase them as regular people. Sometimes, the leaders I work with are reluctant to build a robust story; they think they’re bragging about their background or, worse yet, aren’t proud of some of their career choices. The fact is, your journey is your journey—those are the stops you made along the way. Don’t apologize for them. Every experience helped shape who you are today. Besides, the more important stories involve critical incidents and lessons learned—the very instances you should emphasize and use to grab the audience’s attention.

By studying where you’ve been, and what you’ve learned, you can better chart the course of your future development. What leadership lessons do you still need to learn? What traps do you want to avoid? What experiences do you need to add to your story? Reflect on your own journey by writing and telling your leadership story, and you’ll create a more vivid roadmap for self-development going forward.

Bootstrap Takeaways

Document Your Leadership Journey

1. Create your own leadership story by mapping your critical experiences and lessons learned. Pick out the memorable moments and be specific.

2. Share your leadership journey with others—practice telling your story.

3. Use the past to plan the future—what do you still need (and want) to learn?