When I was a CEO, one of the most enduring shifts we made was in how we talked about careers.
We moved away from the idea of a single ladder and started using the language of squiggly careers, a concept I borrowed from Amazing If https://www.amazingif.com/ and embedded through practical sessions with our teams.
The intent was not philosophical. It was operational.
In many organisations, promotion is still treated as the primary signal of success. The next title. The next rung. The next layer of status. I saw this particularly strongly in parts of Africa, where hierarchy and seniority carry real weight.
Over time, three lessons became clear.
1. The ladder rewards the past, not the future - why promotion often comes before readiness
The first question that kept surfacing was this. Are we actually preparing people for the next level, or simply rewarding past performance?
Too often, strong individual contributors are promoted and then expected to “grow into” leadership. We assume they will quickly learn how to move from delivery to enabling others, stay steady under pressure, work through conflict, set boundaries, give difficult feedback, and lead with consistency.
These are not small extensions of the role they were doing before. They are a different set of muscles altogether.
When development starts after promotion, people struggle quietly and teams feel the strain. This is not a failure of ambition. It is a failure of sequencing.
2. Careers are built through conversations, not titles - why development plans need to look forward, not just inward
This is where career conversations really matter.
Good development discussions are not just about getting better at the role someone is in today. They are about preparing for what might come next, even if that next move is sideways, experimental, or not immediately upward.
That requires managers who can hold honest career conversations, support real development plans, and actively encourage people to try new things. Stretch projects. Learning secondments. Short-term assignments. Coaching.
It also requires letting go.
The strongest leaders see talent as borrowed, not owned. Their role is not to hold people tightly, but to help them move on well when the time is right.
3. Not everyone should become a manager - designing progression for specialists, not forcing leadership
A related failure I see repeatedly is forcing specialists into management because there is no other way to grow.
Across every sector I have worked in, I have seen exceptional experts who felt the only way to increase influence or income was to take on people leadership. I have promoted some of them. Even with training and support, it did not work. They were unhappy. Teams struggled. Their real value was diluted.
The issue was not their capability. It was the organisation’s design.
Some people add the most value by going deep, not wide. That means creating real specialist pathways, paying expertise properly, stretching people without requiring people management, and being willing to break rigid salary bands when scarcity and value demand it.
Progress should reflect contribution, not headcount.
If your organisation is serious about retaining talent, reducing failure, and building leadership depth, these questions are unavoidable.
How do you define progress?
Who are you preparing early, not just promoting late?
And where are you still forcing the wrong career choices?
If this is something you are actively grappling with, I am always interested in comparing notes.
Warmly,
Liz
Strategic Advisor | Former CEO | Founder, Volante
Based in Kenya, available globally
