As an Executive Coach and the founder of both Blue Unicorn Coaching and Angry Olive Consulting, I’ve had the privilege of working with incredible leaders across a variety of industries, from hospitality to tech and everything in between. One thing that always strikes me is how many of these leaders, whether seasoned veterans or newcomers to management, share a common challenge: building a leadership legacy that lasts.
Too often, leaders get bogged down in the day-to-day grind of running operations, tackling urgent problems, and managing the constant flux of team dynamics. The big picture—the legacy they leave behind—gets lost in the shuffle. And yet, it’s this very legacy that will define their leadership long after they’ve moved on from their roles.
But what does it mean to build a legacy as a leader? And how can you be intentional about creating one that lasts, one that reflects your values, influences those around you, and leaves your business stronger than you found it?
In this article, I’m going to explore how you can build a leadership legacy that lasts by thinking differently, asking better questions, and taking purposeful action. It’s about more than just getting results; it’s about developing the kind of leadership that inspires, motivates, and impacts people for years to come.
What Is Leadership Legacy, Really?
Before we dive into strategies, let’s first define what a leadership legacy is. Your leadership legacy isn’t just about what you accomplish or the position you hold. It’s about how you shape your organization, influence, grow, develop, and mentor the people within it, and contribute to the long-term success of the business. Your legacy is the impact you make on others (both internally and externally), the systems you put in place, and the way you cultivate a culture that can thrive without you. Afterall, if your organization, business unit, department, or team cannot perform just as well when you are on vacation as it does when you are present, what does that really say about the long-term legacy you are building?
Think about the leaders who have left a lasting mark in your life. Was it their accomplishments alone that made them memorable? Or was it the way they made you feel, the way they challenged you to grow, or the way they believed in you when no one else did? A leadership legacy is built on moments like these.
As you move through your career, your legacy is shaped not only by your decisions but by the environment you create. Do you empower your team to think for themselves and ask “ALL” the questions? Do you lead with empathy, vulnerability, and integrity? Or do you play it safe, sticking to the status quo, and avoiding the tough conversations?
Building a leadership legacy that lasts is about creating an enduring impact—one that’s rooted in your personal values and vision. But how do you do that when you’re constantly balancing the demands of the present with the aspirations for the future?
Thinking Differently: Leadership Starts with a Mindset Shift
The first step in building a lasting leadership legacy is to think differently. It’s easy to get caught up in the reactive cycle of managing tasks and putting out fires, but truly visionary leaders know that the long-term success of an organization starts with the way they think about leadership.
Let me paint you a picture: Imagine a leader who spends their days consumed with the details, whether it’s tracking inventory or dealing with an employee dispute. They focus on the “how” and “when,” believing that their role is to manage the day-to-day. But what happens when that leader moves on? Sure, the operations may continue running smoothly for a while, but without a foundation built on leadership principles that transcend the daily grind, things inevitably begin to fall apart. Systems break down, team morale declines, and that leader’s influence slowly fades.
Now, picture another leader who takes a step back, consistently asking themselves: How can I make this situation better for my team in the long run? What will my decisions today mean for the culture tomorrow? How am I inspiring others to be better leaders themselves? They understand that leadership is about creating an ecosystem that thrives beyond their personal presence.
Thinking differently means shifting from a transactional mindset (doing the work yourself) to a transformational mindset (empowering others to grow, take ownership, and innovate). It’s about working on the business far more than you are working in the business. It’s about asking yourself the hard questions that challenge you to think deeper and wider than the immediate moment and adopt a long-term vision for the legacy you want to leave.
I’ve seen this mindset shift in action with a client of mine—let’s call him Dan. When Dan first came to me, he was deeply embedded in the minutiae of his business. He ran a busy restaurant and was constantly running between the kitchen, front-of-house, and the office, managing day-to-day operations. He didn’t have time to think about leadership beyond the immediate needs of his team.
But after some coaching, Dan began to think differently. Instead of reacting to every challenge, he started to anticipate what his team would need to succeed in the future. He began delegating more, trusting his team to make decisions, and giving them the resources they needed to grow. Dan also started asking deeper questions about his team’s development. He asked himself, “How can I help my team become better leaders? What values do I want them to carry forward once I’m no longer here?”
By shifting his mindset from managing to leading, Dan began to build a leadership legacy that transcended his daily role. His business became more resilient, and his team became more self-sufficient and motivated, knowing they were part of something bigger than the day-to-day operations.
Asking Better Questions: The Key to Unlocking Your Leadership Potential
In addition to thinking differently, building a lasting leadership legacy requires you to ask better questions. As a coach, one of the most powerful tools I have is the art of questioning. When you ask the right questions (and allow those on your team to do the same), you unlock insights, inspire reflection, and open the door to growth. The right questions help you avoid surface-level thinking and dig deeper into the why behind your actions, decisions, and leadership style.
Here’s a challenge: The next time you face a leadership decision, try asking a few of these questions:
What will this decision mean for my team’s development in the next 6 months?
How can I empower others to take ownership of this problem?
What kind of culture am I creating with this decision? Is it one that aligns with my values?
If I were to leave tomorrow, what systems would my team need in place to continue succeeding without me?
How can I develop leaders around me, so that they’re better equipped to take on more responsibility?
You can also utilize the “Cummings Decision Making Matrix” – the following four questions can layer across any thought process or decision that needs to be made:
Is it on brand?
Does it serve our target audience?
Can we support our employees?
Is it fiscally and operationally feasible and responsible?
Asking these types of questions forces you to zoom out and think strategically. It requires you to consider the bigger picture of leadership and not just the immediate outcomes of your decisions. These questions also push you to think about how your leadership affects others and what legacy you’ll leave behind in your absence.
The problem is that many leaders don’t ask these questions. They’re too focused on the “urgent” demands of the business or they simply don’t know how to reflect deeply on their leadership practices. But when you make a habit of asking better questions, you’re not just improving your own leadership; you’re developing the leadership potential of everyone around you. The more you focus on what is “important,” the less you find yourself having to deal with the “urgent”
Building Your Legacy Through Action
Once you’ve shifted your mindset and started asking better questions, it’s time to act. A leadership legacy isn’t built on good intentions alone—it’s built on consistent, purposeful actions.
One of the most powerful ways to build your leadership legacy is by investing in your people. Great leaders know that they can’t do it all themselves. They rely on their teams, mentor them, and actively work to help others step into leadership roles.
Think about a situation when someone took the time to develop you, whether it was through feedback, mentorship, or giving you the chance to take on more responsibility. That moment likely had a profound impact on your career and leadership journey. Now, ask yourself: Are you providing that same opportunity to others?
I encourage my clients to actively create leadership development programs within their businesses, whether formal or informal. This could mean offering mentorship opportunities, providing resources for professional growth, or simply creating an environment where team members feel supported in their development.
A great example of this in practice comes from my work with a brewery owner, Stacy. Stacy was passionate about developing her team, but initially, she didn’t have a formal leadership development program in place. Instead, she offered mentorship, gave her team ownership over certain decisions, and made a habit of providing regular feedback. Over time, Stacy’s team grew into a group of strong leaders who could take the business forward without her micromanaging every detail.
Her legacy, as a result, is one of empowerment and trust, and her business continues to thrive long after she moves on to new ventures.
Final Thoughts
Building a leadership legacy that lasts is not an overnight process. It requires you to think differently, ask better questions, and take purposeful actions that are aligned with your values. It’s about keeping “the main thing the main thing.” It’s about creating a culture where your influence can continue to ripple outward, long after you’ve moved on from your current role.
As you reflect on your own leadership journey, ask yourself: What kind of legacy do I want to leave behind? How can I start today to ensure that my leadership not only creates short-term results but builds a sustainable, impactful future for those around me?
Remember, leadership is not just about what you do today—it’s about what you inspire others to do tomorrow. I’ve always said, “If you are not better off for having worked with me (no matter how long or short the time period), I have failed you as a leader.” By thinking differently and asking better questions, you’ll set the stage for a leadership legacy that lasts for years to come through a long line of people who you not only have mentored, advised, and developed, but also will do the same for their teams.
Who will be having a conversation five, ten, twenty years from now talking about how it was you that so significantly influenced their growth and development as a leader in their industry? Now that’s quite a leadership legacy to be proud of!