How to Train New Managers
The biggest mistake companies make with management is treating it as the next rung on their current career ladder rather than a leap to a totally new ladder.
At Proletariat, we often talked about creating a formal manager training program. We didn’t fully implement it, but we built some practices that helped us support new managers as they stepped into one of the hardest transitions in their careers. Becoming a manager isn’t just climbing a rung on the ladder, it’s changing ladders entirely. You stop being measured by your individual output and start being measured by your ability to help others succeed. That’s a career change, not a promotion.
The Six-Month Trial Period
One of the most useful practices we had was giving new managers a six-month window to test whether management was right for them. During this period, they weren’t locked into the role forever. They would start by taking on a single or small number of direct reports to help ease the learning curve. If they found they didn’t enjoy or excel at managing, they could move back into an individual contributor role without stigma or penalty (and this actually did happen!). This reduced the fear of failure and gave people the freedom to explore whether management aligned with their strengths and career goals.
Another opportunity for training managers is to have them take responsibility for an outsource team or contractors. Some parts of the role are different, like there is no need to do career management with an outsource team, but it can be a good taste of the management path.
Tools and Resources for New Managers
We didn’t throw new managers into the deep end without support. Each person had access to:
Books and podcasts: Practical resources on leadership, coaching, and communication.
Mentorship: A more experienced manager who would meet with the new manager regularly to answer questions and share lessons learned. As the CEO I also met with every new manager to make sure they felt supported.
Structure: The six month trial period had several built in check points to ensure progress was being made and that all sides felt like everything was working well.
The goal wasn’t to make them perfect managers in six months, it was to help them understand the realities of the role and whether they wanted to keep doing it. Being a great manager and leader is a lifelong pursuit and we wanted to encourage people to get started on their own path.
Balancing Management and Individual Contributors
Too often, high-performing individual contributors are “promoted” into management by default because managers are more highly compensated. This can create three problems:
Unhappy managers: People who don’t enjoy the management work feel stuck
Weakened teams: Direct reports don’t get the support they need because managers are under skilled or disinterested
Undervalued individual contributors: ICs that don’t choose management feel underappreciated and that they don’t have a strong career path inside the company
This means you need a clear path to advancement for individual contributors to continue to grow in their career and compensation without having to move into management. By reframing management as a career change, you give people permission to opt in for the right reasons. That builds a culture where leadership is intentional, not a requirement.
Making Management Training Scalable
Even without a full “management bootcamp,” companies can build lightweight structures that scale:
Shadowing: Let new managers sit in on important meetings and be part of the performance review process before running their own.
Clear expectations: Define what success looks like in the first 30/60/90 days of managing.
Feedback loops: Get feedback from their team early and often to guide the growth of the new manager.
The structure doesn’t have to be heavy. The point is to make the transition explicit and supported, but also not final.
Final Thoughts
Great managers don’t just appear. Managers are not born, they are trained. Great team members are supported and given the freedom to decide whether leadership is truly for them. By treating management as a career change, not a promotion, companies can avoid the trap of undertrained management and instead grow leaders who want to lead.