Originally published on LinkedIn.
There’s a moment every leader faces and knows! The one where everything feels familiar yet foreign and strangely uncertain, like driving through a blinding snow storm or navigating a heavy fog at night. You can see enough to keep moving but not enough to be sure you’re still on the road.
If you’re piloting a boat… you can’t necessarily trust your senses, you have to allow yourself to trust your instruments, despite what your senses may be screaming! It’s easy to navigate when the path is clear on a map that’s known.
The real test comes when the road ahead disappears and all you have left is instinct, judgment, wisdom, and the trust of the people on the journey with you.
In my work with organizations undergoing digital and cultural transformations, I’ve watched smart, capable leaders stumble or become paralyzed. Not because they lacked talent, capability or will, but because the fog was thicker than they expected... especially when their leaders and peers are stumbling along in the same fog.
Many of today’s most capable leaders have grown up in arenas where their expertise was hard fought, earned, tested, trusted — sometimes even becoming unquestioned. They know their business and processes inside out; it’s a big part of what’s made them successful. And so, the inevitable expectation of leadership perfection occurs.
But since when did omniscience become a prerequisite for great leadership? I know I don’t have it (and I’ve been around a few blocks), and I absolutely know the title “Master of Total Knowledge” doesn’t exist.
So, when a new paradigm arrives, like AI or SaaS, it asks something deeply human of a leader: “Can you risk vulnerability to lead the way through uncertainty?” Trust me when I say it feels awfully uncomfortable to go there — even risky. Sometimes what seems like resistance from a leader can really be hesitation; a moment when their experience no longer charts the way.
That’s the hard truth of unrelenting change; challenging even the most seasoned leaders to find, trust, and embrace a new way. And rather than expose vulnerability in uncertainty, leaders may adopt a defensive position: “This won’t work here,” or, “This has always been successful, so you can’t do it like that.” Often, those are signals that confidence or understanding still need to be found and built.
There’s the truth: it’s not stubbornness; it’s often self-preservation. These are people who are experts in their domain, and when peer expectations of their experience and expertise cause them to feel that domain slipping from their grasp, skepticism becomes a shield. “This won’t work here” isn’t always a technical objection; it's likely a plea for help and clarity.
It may be a signal that things have evolved beyond their current knowledge and that the confidence they feel pressure to instill in those they lead hasn’t yet been found — and so, to them, trust, especially self-trust, is equally elusive.
This is why I believe vulnerability, the outcome of which is knowledge and trust, is the true currency of transformation.
You may have the best architecture, the cleanest data, even best in class tools; but if the people who need to lead and adopt them don’t feel confident enough to trust them, to step into the unknown, nothing will seem to work… and things will inevitably stall! Even worse still, the pursuit of what seems like perfection can become the enemy of good; and good is often what gets you much closer to the goal. Transformation isn’t a one-and-done event.
It’s a journey where the destination matters, but is often unknown… and likewise too, the confidence of everyone walking the path, especially so for those leading the way!
Building confidence takes more than technology, flashy demos and catchy PowerPoint presentations. It takes effort in governance to show there’s a trustworthy structure; accurate storytelling to connect people first to the “vision”, the “why”; and transparency to make progress visible.
It’s being honest about the hard work, dedication and vulnerability necessary to step beyond what is currently known, so you can foray into the uncharted waters of what’s new; crafting the necessary journey to the destination… it’s identifying a North Star, and then keeping your eye on it! It’s not about convincing leaders to abandon what they know. It’s about creating a safe space for them to learn, question, and ultimately own the new model themselves.
I’ve seen what happens when that alignment clicks. Teams stop resisting and start exploring. Skepticism becomes curiosity. Leaders who once said “this won’t work here” begin asking “how can we make this work here?” or, “why haven’t we done this sooner.” The fog doesn’t magically lift; but now there’s a North Star everyone can work toward confidently! A unified, shared vision alongside mutual vulnerability which allows confidence and trust to grow, keeping the team moving forward.
Leadership isn’t about having all the answers. It’s about supporting and guiding others when the answers aren’t necessarily visible or available. It’s about instilling confidence despite the path being unclear! Your identified North Star is the destination, and you’re open to new pathways to getting you there! While finding your way through the unfamiliar or unknown, the role of a leader isn’t to pretend the road is clear but to help people feel confident enough to walk it together.
When that happens, wicked problems stop feeling like dead ends and start becoming challenges we’re equipped to solve. That’s how complexity becomes clarity, and how experience becomes the wisdom that informs your team and instills their trust! That’s how legacy becomes the new destiny and how transformation then endures.