One of the most underrated behaviors of great transformation leaders isn’t a strategy or a framework. It’s something much more human: the ability to genuinely understand what the people around you are actually dealing with.
Here’s something I notice a lot when I work with leaders who are running transformation. They’re incredibly smart. They’re motivated. They care deeply about where the organization is going. And yet — they’re constantly surprised when people don’t come along with them.
And when I dig into it? It’s almost never about the strategy. It’s almost never about the roadmap or the vision or the business case. Nine times out of ten, it comes back to the same thing: they haven’t taken the time to really understand the context of the people around them.
Not just their job titles. Not just their KPIs. But what they’re actually carrying. What tensions they’re navigating. What pressures are keeping them up at night. What’s making this transformation feel threatening to them, even if on paper they’ve said yes.
That’s what this behavior is about. And I think it’s one of the most important ones we can develop as leaders. So let’s get into it. Right?
The Tension at the Heart of Every Transformation
Let’s start with the honest reality of what transformation leadership actually looks like.
You’re not starting fresh. You’re not building something from zero on a clean slate. You are balancing the existing system — keeping the lights on, keeping customers happy, keeping the business running — while simultaneously trying to move towards something fundamentally different.
That dual reality creates enormous tension. And it doesn’t just live at the organizational level. It lives inside every single person in your leadership team.
Your CFO is trying to protect financial stability and invest in the future at the same time. Your head of operations is trying to maintain efficiency today while redesigning processes for tomorrow. Your HR leader is trying to manage current talent pressures while building the capabilities you’ll need in three years. They all hold this tension. Every single day.
“The challenge isn’t getting people to support the transformation. It’s understanding what makes it hard for them to do so — and that starts with understanding their context.”
If you’re leading that transformation and you don’t understand the specific version of this tension that each of those people is carrying? You’re going to push in ways that create resistance you don’t understand. You’re going to make decisions that feel obvious to you but feel impossible to them. And you’re going to wonder why people who said yes in the meeting aren’t really moving.
Understanding their context isn’t a nice-to-have. It’s the prerequisite for everything else.
From “About Me” to “About You” — The Leadership Shift That Changes Everything
I want to be honest about something here. This shift — from being focused on yourself to being genuinely focused on others — is not a given. It’s something that happens over time. And sometimes it doesn’t happen at all, even in very senior people.
Think about where most of us start in our careers. When you’re early in a professional role, you are rightly focused on yourself. On delivering. On proving your competence. On the content you need to bring to the table. That’s appropriate. That’s how you build your skills and your credibility.
But here’s what I’ve seen again and again: the more senior you become, the more you realize that the content — the thing you were so focused on — is maybe 10% of the equation. The other 90%? It’s about connecting with others. It’s about understanding what they need. It’s about how well you can switch your perspective from yourself to the person in front of you.
And here’s the tricky part. Even very experienced leaders can fall back into self-focus — especially when they’re new to an organization or a role. Richard Stark, a leadership expert and coach I deeply admire, talks about what he sees as an almost inevitable cycle.
When a first-time CEO steps into the role, there’s often a healthy dose of imposter syndrome. Am I really good enough for this? I’ve been chosen, but I’ve never done this before. And here’s the thing about that — a moderate level of insecurity is actually really helpful. It keeps you curious. It keeps you humble. It keeps you listening. You’re not assuming you have all the answers. You’re genuinely looking to learn and looking out for what could go wrong.
But over time? If the results are good, the insecurity fades. And sometimes what fills that space isn’t wisdom — it’s overconfidence. Maybe even arrogance. I know the playbook. I’ve seen this before. I don’t need to consult people.
“The risk is that confidence tips into arrogance — and in a world where the rules keep changing, yesterday’s playbook can be tomorrow’s blind spot.”
This is where understanding context becomes even more critical. The more confident you are, the more you need to consciously practice the perspective shift. Because the autopilot will take you straight back to yourself — your experience, your assumptions, your answers.
So the question isn’t just: can I be curious when I’m uncertain? The question is: can I stay curious when I’m confident? That’s the real leadership skill.
You Can’t Fake Being Curious. Right?
I love this insight, and I think about it a lot.
A coach once told me: just be curious. As if curiosity is something you can perform. And look, I’ve tried it. I’m sure you have too. You’re in a conversation, you’re not that interested, but you know you should be. So you ask a question. You nod. You say “interesting.” But the other person feels it instantly. They know.
Genuine curiosity is one of those things that is almost impossible to fake — and that’s actually a really important piece of information. Because it means that if you want to understand people’s context, you have to actually want to understand their context. It has to be real. It’s not a technique. It’s an orientation.
And this connects deeply to authenticity. The leaders who are truly great at this — the ones who make people feel genuinely understood — aren’t running a playbook. They’re actually interested. They actually want to know what it’s like to be in your shoes, facing your pressures, trying to navigate your constraints.
Which brings me to something really important about empathy.
A note on “putting yourself in someone else’s shoes”
We use this phrase all the time. And I think it’s worth pausing on, because it can mislead us. When I put myself in your shoes, I’m projecting. I’m asking: how would I react if I were in your situation? But I’m not you. My history, my fears, my values, my nervous system — none of those are yours. So what I’m actually doing is imagining how I would feel. And that’s not the same thing at all.
Real empathy is trying to understand their shoes. Not wearing them yourself — understanding what it feels like to wear them when you’re the person wearing them. That requires genuine curiosity. It requires asking. It requires listening without filling in the blanks with your own experience.
That distinction matters more than it might seem. Because a lot of what people call empathy in leadership is actually well-intentioned projection. And well-intentioned projection can still lead you very far from what the other person actually needs.
The Autopilot Problem — And Why It Makes You Selfish Without Knowing It
Here’s something I think we don’t talk about enough in the context of transformation leadership. The conditions of transformation — the pressure, the pace, the uncertainty, the constant balancing act — are almost perfectly designed to activate your stress response.
And when you’re in that stress response? You cannot be selfless. It’s physiologically nearly impossible.
Richard explained this in a way that really stayed with me. When we feel unsafe — when the pressure is too high, when things feel out of control — our autonomous nervous system shifts us into fight, flight, fix, or freeze. And in that state, we become a smaller version of ourselves. We lose the wider capacity to see all the possibilities. We stop listening. We become that horse in the race with the blinkers on — running hard, but seeing only what’s straight ahead.
And here’s the leadership consequence: when you’re running on autopilot in stress mode, and you approach someone to get their buy-in or their input or their support — it comes across as selfish. Because it is. Not intentionally. But you’re in survival mode. You’re trying to make yourself safer. And that comes through.
People don’t feel understood in those conversations. They feel used. Or steamrolled. Or like they’re just a means to your end.
The Autopilot Loop
High pressure → stress response → fight/flight/fix/freeze → tunnel vision → self-focused → people don’t open up → less information → worse decisions → more pressure.
The loop feeds itself. And it’s incredibly common in transformation contexts. The question is: where do you break it?
The break comes from awareness. From noticing — often physically — that you’ve been triggered. And from choosing to pause before you react. Viktor Frankl wrote about this beautifully: between stimulus and response, there is a space. And in that space is our freedom and our power.
That space is where good leadership lives. That’s where you can switch off the autopilot and choose to show up differently. To be present. To be curious. To focus on them rather than on what you need from them.
But you can only access that space if you notice you’ve left it. And noticing requires practice.
Both/And: The Polarity Problem in Transformation
I want to talk about something that’s directly related to understanding context — and that’s what happens when you have smart, well-intentioned leaders who are genuinely trying to understand each other, and they still end up in conflict.
Because sometimes the issue isn’t misunderstanding. Sometimes the issue is that people are actually representing genuinely different — and equally valid — perspectives. And if you don’t understand that dynamic, you’ll keep trying to resolve a tension that isn’t actually resolvable. At least not the way you’re approaching it.
Richard introduced me to the concept of polarities. The idea that many of the challenges leaders face in transformation aren’t problems to be solved — they’re tensions to be managed. They’re both/and situations, not either/or.
A classic example? Global scale versus local customization. Every large organization I’ve ever worked with has wrestled with this. And what tends to happen — without fail — is a pendulum swing. First everyone decides that local customization is the priority. They rush towards it. And over time, the efficiencies of global scale start to erode. So the pendulum swings back. Everyone rallies around global scale. And then the organization loses touch with its local markets. And around it goes.
The reason this keeps happening is that leaders keep treating it as a problem with a solution. But it’s not. It’s a polarity. You need both. You need global scale and local customization, held in a kind of dynamic balance — adjusting, tracking, adapting as conditions change.
And here’s where understanding context comes back in. You cannot manage a polarity alone. You need the people who are closest to the tensions — the ones who can see when the balance is tipping — to speak up. You need them to feel safe enough to raise the early warning signals. Which means you need to understand their context well enough that you’ve built the kind of relationship where they will.
No single leader — no matter how smart, no matter how experienced — can see all of this from the top. The information lives in the people around you. Your job is to create the conditions where it can surface.
Being vs. Doing — The Mode That Changes Everything
Here’s something I’ve been sitting with lately. We talk a lot in leadership about what to do. What actions to take. What conversations to have. What processes to put in place. And all of that matters. But there’s a mode that underlies all of those things — and if that mode is off, none of the doing will land the way you want it to.
That mode is being.
Being present. Being genuinely there with the person in front of you — not already thinking about the next meeting, not replaying what went badly yesterday, not composing your response while they’re still talking. Actually being with them, in this moment, with full attention and no agenda beyond understanding.
This sounds simple. It is very hard.
Especially in transformation contexts, where the calendar is packed, the pressure is high, and there are fifteen things that feel more urgent than sitting with a fellow leader and really listening. The temptation is to turn every conversation into a transaction. To get in, get what you need, and get out.
But here’s what I’ve seen: the leaders who are most effective at bringing people along in transformation are almost universally good at this. They have a quality of presence that makes people feel like they’re the only thing that matters in that moment. And it creates safety. It creates openness. It makes people willing to share things they wouldn’t share with a leader who’s clearly already somewhere else.
“The quality of being present with someone is really what unlocks the conversation. Not the questions you ask. Not the technique. Just — actually being there.”
One practical way in: notice physical sensations before you go into an important conversation. Not as a therapy exercise — just as a way to anchor yourself to the present moment. The sound in the room. The light. The feeling of your feet on the floor. Small things that pull you out of your head and into right now.
It sounds almost too simple. But it works. And it takes thirty seconds.
The Tiny Habit That Changed How I Prepare for Conversations
For each of the leadership behaviors we work with, we try to identify one tiny habit — something small and concrete that you can actually start doing tomorrow. Because big behavioral change rarely comes from big intentions. It comes from small, consistent practices.
For understanding context, here’s the one I keep coming back to — and that I use myself.
Before any conversation with a fellow leader about transformation, take two minutes to think about the specific pressures they’re under that might make this difficult for them.
Not in a manipulative way. Not to figure out how to work around their concerns. But to genuinely get curious. What is it like to be them right now? What are they trying to balance? What might they be afraid of? What would transformation cost them, in terms of their team, their budget, their sense of control?
When you walk into a conversation with that kind of preparation, something shifts. You stop being someone who needs something from them. You become someone who actually sees them. And that shift — from me to us — changes the entire quality of the conversation.
It turns a potential negotiation into co-creation. It’s not me trying to get you to support my transformation. It’s us figuring out together how to make this work, given everything we’re both carrying. Right?
One More Thing: Let Someone Help You See Your Blind Spots
I want to end with something that I find both obvious and underused.
If you’re working on staying more present, more other-focused, more aware of when you’ve gone into autopilot — you don’t have to do that entirely alone. In fact, it’s much harder if you try to.
Pick one person in your organization — someone you trust, someone who’s close enough to see you in action — and ask them a simple thing: when you see me go into flight mode, when I look like I’m running on autopilot and not really listening anymore, let me know.
Give them permission. Make it safe. And then actually use what they tell you.
The leaders who grow fastest in this kind of work are rarely the ones with the most self-awareness from the start. They’re the ones who’ve built the right relationships to get real feedback — and who’ve made it safe for the people around them to give it.
That’s also, by the way, an act of understanding their context. Because when you ask someone for that kind of feedback, you’re saying: I see you. I trust you. Your perspective matters to me. And that creates exactly the kind of relationship where both of you can do better work together.
So, Where Does That Leave Us?
Understanding their context isn’t one conversation or one exercise. It’s a practice. It’s something you build over time, with intention, with curiosity, with the willingness to slow down when everything is telling you to speed up.
It means holding the tension of the transformation with your fellow leaders, rather than pushing it at them. It means approaching every leadership conversation with genuine curiosity about what they’re carrying. It means staying present enough that people feel safe to tell you the truth.
And ultimately, I believe this: the leaders who can do this — who can really understand the context of the people around them — create faster, better, more sustainable transformations. Not despite taking this time. Because of it.
Because transformation isn’t something you do to an organization. It’s something you build with the people in it.
Yeah. That’s the whole thing, really.
Your Tiny Habit for This Week
Before your next conversation with a fellow leader about transformation, take two minutes to think: What is this person actually dealing with right now? What pressures are they balancing? What might make this hard for them?
Walk into the conversation with that as your starting point. Notice what changes.
Part of the Good Behaviors for Transformation Leaders series · Human-Centric Leadership by Zanna van der Aa
