Leadership, Then vs. Now: Why Every Generation Needs an Update
Summary: Leadership has evolved, but many professionals still rely on outdated habits formed early in their careers. In today’s fast-paced, tech-driven world, modern leaders need human-centered skills like adaptability, empathy, and narrative agility. This post explores how every generation can update their leadership style to stay relevant and effective.
Could old leadership habits be quietly holding you back?
Leadership has changed. And it’s not just a generational issue. It’s a shared challenge.
No matter when you started your career, chances are the leadership model you were handed needs a refresh.
But most of us were raised on leadership models that no longer match the pace or complexity of today’s world. Think command-and-control. Loyalty over learning. Certainty over curiosity.
It’s not that those ways were “bad”…they made sense back then. But today, things move too fast, change too often, and require something more human from us as leaders.
Let’s unpack what might be happening.
Where Our Leadership Instincts Come From
Early in your career, you probably modeled leadership based on what you saw. Maybe it was a boss who always had the answers. Or a culture that rewarded polish and authority over vulnerability and growth.
Read more about my journey leaving a career as a management consultant on the partner track here
Those early examples shape our instincts.
And that’s true whether you started your career in the 90s or just five years ago. Every generation has a version of leadership they’re unconsciously carrying forward.
They define what we think “strong leadership” looks like.
And if we never pause to revisit them, we carry those patterns forward even if they no longer fit.
You Might Be Ready for a Shift If…
You’re doing what worked before, but it’s not landing like it used to.
Here are a few signs your leadership style might need an update:
You’re doing “all the right things” but your team still feels disengaged
You’re feeling more drained than energized
Adapting to change feels harder than it should
You feel stuck between who you’ve been… and the kind of leader you want to be
These aren’t failures. They’re signals.
And they’re pointing toward your growth edge.
What Leadership Looks Like Today
To lead well now, it’s not about being the expert in the room or having everything figured out.
It’s about staying human, grounded, and adaptive…especially when things are unclear.
Here are 10 human skills modern leaders rely on:
Sensemaking – Making clarity from chaos
Self-regulation – Staying calm and responsive, not reactive
Curiosity – Asking better questions instead of chasing perfect answers
Empathy across contexts – Understanding the human side of work
Narrative agility – Helping others make sense of shifting goals
Discerning focus – Saying no, wisely
Comfort with incompleteness – Leading through unknowns
Trust-building at scale – Creating psychological safety across teams
Learning in public – Showing your growth, not just your wins
Interfacing with systems – Seeing how tech, people, and culture connect
These aren’t “nice to haves.” They’re the new foundation.
Time to Let Go of “Old School” Leadership Habits
Some of what used to work just doesn’t serve us anymore. For example:
Relying on authority can create distance instead of trust
Long-term planning struggles in a fast-shifting world
Being the expert leaves no room for team ownership or new ideas
In-person charisma won’t carry you in a hybrid culture
And here’s the truth:
You don’t need to abandon your strengths. Just evolve them.
This Is Your Opportunity
If leadership has felt harder lately… you’re not doing anything wrong. You’re just growing beyond an outdated model.
You’re ready for what’s next.
To lead with clarity, not control.
To connect with others, not just direct them.
To be real, and still respected.
No matter your title, age, or background, this is the moment to evolve your leadership to the next level.
Feeling the shift? Let’s talk.
Book a call, and let’s explore how you can grow into the kind of leader today’s world is calling for.
