My first mentor taught me a very valuable lesson. Part of learning is also earning your own war stories and the best way to learn is to fail.
Afterwards I have always endeavored to do the same when coaching people, that is create an environment where:
- they have strategic objectives but can set their own tactical goals
- have global freedom wrt the deadlines but are held accountable when they commit to one
- have some resources to manage
As a CISO running a small team in a big org I needed everyone to have at least some basic skills in the following domains:
- interacting with clients
- analyzing contracts
- basic technical chops (some scripting to be able to analyze logs)
What I did was:
- Talk to other Directors: who are they coaching in their team? can we have our juniors team up on projects?
- give projects that had actual business values: nothing that could tank the quarter but enough to be noticed outside of the team
- give them at least one direct report to manage: me, for one hour a week
Then I let them work. I keep my hands away from the controls unless I see resume-generating events looming.
They must completely trust the sandbox, know that you won't let them blow their leg off. They must also understand that if they create a mess they will also have the responsibility to clean it and pivot from it to create value.
This dynamic worked especially well for distributed/remote teams. Managing by outcomes over time beats monitoring "active" status any day of the week, it allows asynchronous workflows, trust and underperformers will opt out quickly because there's no fluff to hide behind.