We Develop Leaders Too Late

Miles Canyon, Whitehorse, Yukon

Over the years, I’ve seen too many bad leaders. For a long time, I thought the problem was the individuals. I don’t think that anymore.

One Path to Advancement—and Its Pitfalls 

In many organizations, there is still really only one path to advancement: manage people. Some individuals—strong individual contributors—step into leadership roles reluctantly because that’s where higher pay and opportunity sit. Others step in eagerly—committed, motivated, genuinely wanting to lead well. Both groups are routinely failed. 

We promote people into leadership roles without actually preparing them to lead.

Late Leadership Development 

When it exists, leadership development often shows up as annual, one-off trainings—sometimes delivered years after someone has already been managing a team. By then, habits are ingrained, pressure is high, and mistakes have already had real consequences.

A few years ago, while discussing a potential leadership development program, an executive told me her first leadership training didn’t come until she was an executive—long after being a manager and director for many years. “At that point, it’s too late,” she said. 

I don’t fully agree. The need for learning as a leader is never actually over—roles evolve, contexts shift, and expectations change. But I do agree with what sat beneath her statement: leadership development starts far too late.

It needs to start earlier. Not at the first managerial role, but before someone is ever responsible for others.

Learning to Lead in Real Time 

In my experience as an employee, manager, and now leadership coach, I’ve seen how much smoother transitions could be if emerging leaders were equipped before stepping into their first formal managerial role—with foundational skills, tools, and the mindset to lead effectively. Too often, strong technical experts are pushed into management and struggle—not for lack of commitment, but because leadership draws on a completely different set of capacities than those that made them successful individual contributors.

Of course, many leadership skills are refined in real time—they have to be. But the understanding and development of those skills, and the mindset shift from doer to enabler, should start earlier. 

I stepped into leadership as a subject-matter expert, well prepared to do the work but not to lead others doing it. Like many experts, I was naturally drawn back into execution. I was fortunate to have a team that granted me the grace to stumble, trip! stumble, trip! (to quote my children’s favorite book) before I found my footing as an enabler. 

I quickly realized that leadership requires a very different set of skills—listening deeply, supporting growth, balancing guidance with autonomy—and had I been better prepared, I could have been more thoughtful and effective from day one. Experiencing this firsthand reinforced just how critical early leadership development is—not just for individuals, but for the teams and organizations they lead.

Why It Matters 

The data reinforces this. Leadership experiences shape how people feel about work and leadership itself. Poor leadership has two major consequences.

• First, it drives disengagement and attrition—strong employees leave, or check out emotionally, when leaders fail to support, listen, and enable their teams.

• Second, it discourages emerging talent from aspiring to leadership roles. Despite Millennials and Gen Z set to make up 74% of the workforce by 2030, a majority report they do not want to pursue managerial positions. This is in large part due to redefined understandings of success and shifting career aspirations, but also compounded by having experienced poor leadership firsthand.

Rethinking Leadership Development 

In this next series, I’ll be exploring why we need to rethink leadership development—starting with when it begins. Specifically, why prioritizing leadership development earlier, more intentionally, and with greater investment matters not just for emerging leaders, but for the health of organizations as a whole.

If you support future leaders, this conversation matters.

Your Turn 

Think back to your first leadership role: were you prepared, or did you have to learn once the stakes were high? How did that shape the leader you became—and how you want to lead others?