I had a conversation recently with a business owner about leadership transitions, and it highlighted something I see more and more in my work.
As an early Gen X’er, we were sent out to “just go figure it out.”
We fell down, scraped our knee, rubbed some dirt on it, and kept going. We didn’t wear bike helmets, and our parents cut the seat belts out of cars because they were uncomfortable and never used. There wasn’t a lot of structure. As we went into the workforce, we put up with things because that’s just how it was. If we had a good boss, that was a bonus, not an expectation. And changing jobs wasn’t easy. We waited for the Help Wanted ads in the Sunday paper, typed up a resume, mailed it in, and waited. By the time we heard back, whatever frustration we had probably passed.
So you stayed. You kept your vacation and 401(k) vesting. You figured it out. You built resilience.
The next generation grew up differently.
They had organized sports, not just pickup games in the street. In school, they were given rubrics that clearly showed what it took to succeed. There were defined expectations, clear feedback, and a path to follow. They weren’t told to “figure it out” nearly as often, they were shown how to succeed.
And sometimes I have to remind my generational peers, these are our kids. We did this.
And now they’re leading.
At the same time, the employment landscape has completely changed. Today, people expect to be treated well, and they have options. If something isn’t working, they don’t have to wait. They can find another job quickly. They’re not starting over the same way we did, with one week of vacation and years to rebuild benefits.
So what does this mean for leadership?
It means the rules have changed.
This isn’t about one generation being right and the other being wrong. The leaders who built businesses by figuring it out did exactly what was needed at the time. That approach created strong, resilient organizations.
But today’s environment requires something more.
Many of today’s leaders perform best with a clear framework. Not because they’re less capable, but because they’ve been trained to operate within structure. When expectations are clear, they can focus their energy on solving problems, making decisions, and moving the business forward.
That’s where tools like personality assessments and EOS (I’m not a facilitator, just an advocate) can help. Not as bureaucracy, but as a way to create clarity so leaders can spend less time figuring out how to work, and more time doing the work that matters.
The most effective organizations today aren’t choosing one approach over the other.
They’re combining them.
They bring structure where it helps and rely on experience and judgment where it matters.
That balance is what allows businesses to transition, grow, and stay strong across generations.
And in many cases, that’s the difference between a leadership transition that struggles… and one that succeeds.
