The Change-Maker’s Playbook: 10 Lessons for Transformational Leadership
Ever feel like leading change is a bit like herding cats through a room full of rocking chairs, blindfolded? If so, welcome to the club!
Managing teams is challenging enough, but leading transformation? That’s a whole different level of complexity requiring strategy, agility, empathy – and whole lot of resilience as a leader.
Having spent my career driving change and helping companies tackle the "impossible", here are my top 10 insights for anyone navigating the exhilarating, often stormy, seas of transformation and change.
10. Know What You’re Actually Trying to Change
It’s a classic trap: you think the goal is crystal clear, but when you dig in, you realize everyone has their own interpretation of what “transformation” means and what “change” looks like. Sometimes companies say “transformation” when they mean, “implement a new technology platform”. Sometimes companies say, “culture change,” when they mean, “We aren’t ready to change the operating structure, processes, incentives, or people.” It’s not unusual to interview for a Transformation leader role with 10 people at the same company and hear 10 different versions of what the problem is and what the role is intended to address. Part of the job of the leader is to get people on the same page, but it’s good to know the rough parameters before you accept the job.
9.??Start Where You Are, Not Where You Want to Be
Vision boarding is great, but action starts with an honest reality check. Ask yourself these questions:
Successful change requires a grounded understanding of your starting point before you dive in.
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8. Don’t Let a Crisis Go to Waste and Create a Compelling Vision
Here's a secret: crisis can be your best friend. Why? People and organizations rarely change and move outside their comfort zone unless forced or the status quo is more painful than the risk of change. When there's an urgent problem, suddenly you have everyone’s attention. But what if you don’t have a crisis? Please don’t manufacture one. Instead, create a compelling vision that people can rally around. It needs to be big enough to feel almost scary, and exciting enough that people want to be a part of it. Whether it's the pressure of "we’re in trouble" or the excitement of "we’re going to change the game," both can be powerful fuel for change. And to be blunt, crises and compelling visions get funded.
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7. Do a Pre-Mortem: What Will You Regret Not Doing?
Before launching into a major change, take the time to do a pre-mortem. A lot of time when we’re creating a compelling vision, we focus on what success will look like. There’s also value in imagining a future where things don’t go well. Think about what you wish you’d done differently. What will you regret not tackling sooner? A pre-mortem helps you learn, listen, and set the boldest goals with intention while avoiding the landmines in your path. As an Eternal Optimist leading transformation and change, I like to believe the best, but I do my best to plan for the worst. This makes me more resilient as a leader and the organization becomes more agile in response to both expected and unexpected setbacks.?
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6. Build a Team That Balances You Out
Transformation and change are team sports, and no single leader can cover all the bases. Effective deployment of talent starts with your team. If you’re a big-picture visionary, recruit others who thrive in the details. If you’re cautious, team up with someone who’s wired for bold leaps. Tap into those internally who have seen change fail in the organization – they have insights on Red Flags (in people and behaviors). I know it can be tempting to recruit in the people who have helped you drive change in other organizations but be aware of the need to balance external thinking with internal knowledge. Together, you’ll have the balance needed to create sustainable, meaningful change.
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5. Clarity is a Superpower (And People Crave It)
In time of uncertainty and when things are shifting constantly, a clear message cuts through the noise. People want to know: what are we doing and why does it matter? As leaders, clarity is our superpower. We don’t need all the answers, but we do need to anchor people in the purpose. Bring focus, reassure people, and keep the path forward visible, even when the ground is shifting. As leaders, we have to give clarity. Clarity on what transformation means for the business. Clarity on what needs to change. Clarity on what success will look. Clarity on how progress will be measured. Clarity on how to get there and the role each employee plays in the change. Yes, I said “each employee” because transformation and change require each person to know how what they do at work every day moves the organization forward. I’m talking about attitudes, habits, and deeply held beliefs – not just job tasks. Spoiler alert: these are way harder to change than technology, but it’s a non-negotiable for sustainable change.
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4. It’s All Relative
Everything is relative and most everything should be measurable. As a leader, you’ll learn that speed, pace and progress are especially relative. The speed at which you’re able to drive transformation at a performance-culture modern bank with a supportive executive team is very different than the speed at which change will happen at a 100-year-old insurance company with a skeptical and reticent executive team. It’s the job of the leader to push the boundaries of comfortable. If there aren’t failures along the way, then you aren’t pushing the limits of what is possible. ?
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3. Use Every Win as Fuel
Wins don’t come every day, so when you get one, make it count! A victory isn’t just a happy moment; it’s fuel for more change. Use it to prove that your approach works, to motivate the team, and to keep the momentum rolling. A small win can be the catalyst for the next big move. Too often, companies say, “Ok, this is working. Let’s pause on pushing so hard,” not realizing that it’s critical to use these periods of progress to keep the momentum rolling. Leverage the wins to be points of activation and acceleration.
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2. Don’t Lose Sight of the Vision — Keep Your North Star Bright!
When you’re deep in the trenches of transformation, it's easy to lose sight of the bigger picture. The vision that felt crystal clear at the beginning gets buried under day-to-day hurdles, spreadsheets, and back-to-back meetings. But if you lose sight of the vision, so will everyone else. As a leader, your role is to keep that North Star visible — not just for you, but for everyone on the journey. Remind people of why this matters, of the change you’re all working toward, and how each step gets you closer. Even when things feel chaotic, that vision is the glue holding it all together. So, don’t let it fade into the background; bring it into every conversation, every milestone, and every team huddle. Because when people can see the why, they’ll push through to get to the how.
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1. People Aren’t Obstacles — They’re the Whole Game
When it comes to transformation and change, it’s people, people, people. This might be a surprise because the things most frequently talked about are AI, CRMs, ERPs, and other alphabet-soup acronyms for technology. But make no mistake: it’s humans, not technology, that determine an organization’s transformation and change. Moving the hearts, minds, and hands of people is the trifecta that actually gets things done. In the end, leading change is about connecting on a human level and understanding the complicated emotions that drive human behavior.
It’s a tough thing to push towards a 5-year vision when people are stuck in the here-and-now – grace and empathy go a long way.?As Oprah Winfrey says, “The greatest leaders recognize that they can only go as far as the people they’re leading are willing to go. That requires empathy, respect, and the ability to inspire others to believe in the vision."
Special note for leaders brought in from the outside to lead change:
It’s a lonely job to be an outsider leading change and transformation. You won’t have the relationships within the company to fall back on for advice and friendship – you’ll build these over time, but people will be wary because you’re changing their jobs and sometimes they feel you are even challenging their professional identity and view of the world. People do not like change, and you will be the driving of change. Even if they like you personally, you will be seen as a threat by many.
I say this because it’s important to build a support network elsewhere. I don’t mean just friends and family – although those are helpful. I mean a professional network of trusted people you can reach out to for advice and commiseration on the inevitable challenges and setbacks that occur during leading large-scale change and long-term transformations. This really helps with your resilience and mental health, and I think you’ll also find it helps broaden your perspective and inspire new ideas.
Now, go out there and be the change. Or, at the very least, be the person who helps others get there.
Leaders of change and transformation:
I’d love to hear from you. What would you add to this list or change?
#transformation #leadership #changemanagement #leadingchange #leadingtransformation #leadingwithpurpose #intentionalleadership #digitaltransformation #businesstransformation #transformation #wearemavens #unleashingmavens
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Than you, Jimmy Chou, for tagging me. And thank you for sharing, Angela Spencer. I really like these lessons, and so many resonate with me. Angela Spencer, you asked for some thoughts and here are mine: #1. Love your willingness to state people are first. Too many in change forget this critical element of success because the easier part is rarely the people part. #2. In establishing a North Star, I agree with you! I would add that we need to be sure we have the right one. Often we determine that star is implementation, when it should be integration. #7. I love the idea of a Pre-Mortem. This is a great place to use "Should vs Could" in the conversation. Instead of "What should we do to make this work?" go with "What could we do to make this work?" Makes it less parental. Thanks again!
Donna Highfill would love this and look forward to her thoughts, as well