There’s a moment in every leader’s year — it usually sneaks up sometime between late November and early December — when a quiet question taps you on the shoulder:
“Is my leadership style still serving the people I lead… or have I outgrown it?” Most leaders feel that tap.
Few pause long enough to answer it honestly.
And fewer still allow the answer to influence how they operate. But here’s the truth that’s easy to forget: Leadership styles are not permanent. They’re not personality traits.
They’re not “just who you are.”
They’re choices — often outdated ones — that you carry forward long after they’ve stopped working.
The leaders who shape industries, inspire teams, and transform cultures all share one pattern: They evolve.
And almost always, that evolution begins in discomfort.
Let me share three real-world examples — from manufacturing, entrepreneurship, and global technology — that show just how powerful leadership evolution can be.
The Toyota Way: Improvement Built on Courageously Simple Questions
The Toyota Way didn’t burst onto the scene with fanfare or consultants. It emerged slowly, almost quietly, from a mindset and a discipline that challenged everything traditional manufacturing believed at the time.
In the early days, Western executives dismissed Toyota’s approach as too deliberate, too respectful, too slow.
But Toyota wasn’t chasing speed — they were building excellence. One standard, one process, one human interaction at a time.
Taiichi Ohno, often considered the architect of the Toyota Production System, once said: “Without standards, there can be no improvement.”
He meant this literally — you can’t improve what you can’t define — but also culturally. A leader’s behavior sets the standard. If the standard is unclear, improvement can’t happen.
What many people don’t know is that Ohno was famous inside Toyota for asking a deceptively simple question during shop-floor visits:
“Why?”
He would ask it five times in a row until the real problem was uncovered. In one interview, a Toyota manager recalled: “Ohno wasn’t trying to embarrass anyone. He was trying to liberate us from our habits.” That’s leadership evolution. Not adding complexity, but stripping it away until the truth becomes visible again.
Sara Blakely: Outsider Thinking as a Leadership Advantage
Sara Blakely built Spanx by questioning every “industry standard” she encountered. She didn’t come from retail. She didn’t come from fashion.
She didn’t have a product design background. And that… was her superpower.
Buyers told her she didn’t know what she was doing. Manufacturers rolled their eyes at her prototypes.
Industry experts rejected her because she didn’t speak their language. But Blakely had something else — an unstoppable beginner’s mindset.
She once shared in a talk at Stanford: “The word ‘no’ just became a challenge to figure out another way.” Blakely also talked about how she reframed embarrassment.
Her father would ask the kids at the dinner table:
“What did you fail at today?”
Not to shame them, but to celebrate taking risks.
She learned that discomfort isn’t a threat, it’s a signal.
It means you’re leaning into something new, something worth exploring.
Nadella: The Hardest Leadership Shift — From Knowing to Learning
When Satya Nadella took over Microsoft, the company was successful — but stuck. The culture rewarded being right, being smarter, being the expert in the room.
Nadella didn’t respond with a restructuring chart or a new mission statement. He responded with empathy.
He said: “Empathy makes you a better innovator.”
That wasn’t a polished corporate line.
That was a real human being reflecting on real life and allowing it to shape how he led millions of people.
He introduced the idea of moving from a “know-it-all” culture to a “learn-it-all” culture. This was a radical shift. It forced leaders to put curiosity above ego.
It encouraged teams to listen before reacting. It asked managers to coach, not command.
So What Does This Mean for You?
We often enter December thinking about goals, metrics, budgets, and plans. Important things, no doubt. But overlooked is a far more fundamental question:
“Is the way you lead still working?”
The Toyota Way teaches us to examine our systems. Sara Blakely teaches us to challenge assumptions. Satya Nadella teaches us to evolve our presence.
Your leadership style is a living, evolving tool. And evolution requires intentionality.
Think About This
- What part of your leadership style has become automatic rather than intentional?
- Where have you defaulted to “the way we’ve always done it”?
- Which part of your leadership system needs a tune-up?
- What would your team say if asked, “How has your leader grown this year?”
Action Step
Before the year ends, pick one element of how you lead — your meetings, your coaching style, your communication habits, your decision-making pace, your presence in conversations — and upgrade it.
Wenkroy International LLC is a Professional Advisory company with a main purpose of helping entrepreneurs and business people create the strategy, the plan and the steps necessary to achieve that person’s vision for their business and often their life, while navigating the obstacles which may be blocking them from reaching their goals. The process may involve one on one coaching, advising, laser focus days, personal growth workshops and more. The methods utilized are determined together. The results and value positively impact individuals, teams, divisions and across entire companies. People are now able to focus on what matters most to them, because, they have clarity on where they are heading.
As always share the information in this article with people you know.
