Most independent schools build their next generation of leaders by accident. Someone leaves unexpectedly, everyone scrambles, and the job goes to whoever has been there longest or seems most capable in the moment. In a recent episode of The Table, I sat down with Rebecca Malotke-Meslin, founder of Pleasantly Aggressive Coaching and Consulting, and we kept circling the same pattern: two of the systems that decide who becomes a leader, delegation and succession, are the two systems schools almost never build on purpose.
Rebecca spent more than 20 years across sales, marketing, communications, and school leadership before turning to coaching early and mid-career women in schools and nonprofits. Her lens is women in leadership and equity. Mine, after two decades in student life, is systems. Where those two meet is a practical idea: the work of developing people is not a personality trait, it is a structure you can design.
Key takeaways
- Delegation is harder for women than “just delegate more” makes it sound, because of socialization and perfectionism, not a lack of skill (Rebecca’s frame).
- When you refuse to hand work off, you are not protecting your team. As Rebecca puts it, “when you don’t delegate, you rob people of the opportunity to learn.”
- Delegating on purpose starts with one question: should this task even exist? Eliminate before you assign.
- The informal “tap on the shoulder” is not a succession plan. It rewards the loudest voice in the room, and that has a bias built in.
- You do not need a grand program. Pick one or two roles, pilot a plan, and iterate.
Why “just delegate more” is useless advice
Rebecca made a point I have watched play out for years. A leader is drowning, and the guidance from above is one sentence: “You need to delegate more.” That is the whole instruction. There is no how attached to it.
For women in particular, Rebecca argues, the barrier is not competence. It is what we were praised for on the way up. Women are rewarded for figuring things out alone, for “give it to me, I’ll take care of it.” Asking for help can feel like admitting you do not know something. Layer perfectionism on top, the same perfectionism that helped many women reach senior roles, and handing work off becomes a threat: what if they do not do it the way I would? In independent schools, most leaders also came up through teaching, where you have full autonomy in your classroom and no one to delegate to. Nobody ever taught them the skill.
There is a difference between knowing you should delegate and knowing how. Naming why it is hard is where Rebecca starts every workshop, and it is the right instinct. The presenting problem, “I can’t seem to let go,” is rarely the actual problem.
Delegation is how you develop people
Here is the reframe worth sitting with. We tell ourselves that carrying everything protects our teams from being overwhelmed. Rebecca flips it: hoarding the work robs people of the chance to grow. One of her clients has repeated this line back to her for years: “when you don’t delegate, you rob people of the opportunity to learn.”
Think about your own path. At some point someone handed you a task you were not sure you could do, walked you through it, and then you owned a new skill. That is how a workplace is supposed to work. High-achieving leaders forget those moments and start expecting themselves, and everyone around them, to already know everything.
Rebecca offers a simple test. If you go on vacation for a week and everything falls apart, you have not delegated, you have created single points of failure. Cross-training is not a nicety. It is how you keep the work from collapsing around one person, which is the opposite of a sustainable model.
What delegating on purpose looks like
When I asked how leaders actually make the shift, Rebecca laid out a process. The short version:
- Commit to yourself first, then tell your team it is coming. Many leaders fear the team will resent more work. More often the team already sees you drowning and has been waiting to help.
- Interrogate the plate. Map who owns what across the team. Summer, or the start of a fiscal year, is a natural window for this.
- Eliminate before you delegate. This is the hardest step. As Rebecca says, in independent schools “we love addition, we hate subtraction.” Before you hand a task off, ask whether it should be done at all. Do not delegate something that should simply end.
- Delegation is not always internal. Sometimes the right move is to outsource a task, not push it onto an already-full colleague.
- Communicate outcomes, not methods. Describe what the finished thing should look like and leave room for the person to get there their own way. Telling someone exactly how usually just means “the way I would do it.”
- Set the check-in in advance. Instead of hovering, name the date: “It’s due Friday, I’ll check in Wednesday.” Everyone’s stress drops because the anxiety of the surprise drop-in disappears.
- Pick one thing. Run one task all the way through so you can see where it got hard. Try to delegate four at once and it fails, you confirm your own worst belief (“I should have just done it myself”), and you never delegate again.
The tap on the shoulder is not a succession plan
The same accidental pattern shows up one level higher, in who gets developed as a leader at all. Rebecca points out that most independent schools have no real succession planning. A role opens, and leadership scans the room for the most capable person standing there. Often that is a woman, since our schools run 75 to 80 percent female. But being the smartest person in the room is not the same as being prepared. If nothing was done to develop her, she is set up to fail.
The equity problem sits inside the informal version of this: the person who walks into the head of school’s office and says “put me in, coach” gets the next opening. Rebecca’s point is that plenty of capable people never learned they were allowed to ask, so we end up handing opportunity to the loudest, most confident, most boisterous voice, which tends to skew toward the men in the room.
I call this the hidden hierarchy. The outgoing and comfortable have the informal conversations and get promoted, while the genuinely interested person who does not know the pathway waits quietly for a chance that may never come. Rebecca’s fix is a system: proactive career conversations with everyone on staff, not just the ones brave enough to raise a hand. Ask people what they want for their future, offer equitable access to the assignments that actually build leaders (board committees, strategic planning), and stop reserving them for whoever gets tapped. That is how you build a real pipeline, and it doubles as a recruitment and retention tool once people hear your school actually develops its people.
Where to start without building a monster
If this feels like a mountain, Rebecca’s advice mirrors her delegation process: start small. Commit first. Pull your hiring and retention numbers honestly, because most schools believe they are better at this than they are. Then pick one or two roles, sketch what a succession plan for each would look like, and pilot it. Gone are the days of the 50-page plan you execute perfectly. Build a five-page version and iterate, iterate, iterate.
None of this is about doing more. It is about doing the structural work once so the whole team, and the leader, can breathe. That is what strong student life systems actually protect against: the day everything depends on one exhausted person.
If you are the person everything currently runs through, know this. You do not have to do this alone.
FAQ
Why is delegation harder for women in leadership? Rebecca Malotke-Meslin argues the barrier is socialization, not skill. Women are often praised for handling everything alone, so asking for help can feel like admitting weakness. Add perfectionism and a teaching background with no one to delegate to, and handing work off feels genuinely unnatural.
What is the first step to delegating a task well? Ask whether the task should exist at all. Rebecca recommends eliminating unnecessary work before assigning anything, so you never hand off something that should simply stop.
How should a leader communicate a delegated task? Focus on the outcome, not the method. Describe what the finished result should look like, set a specific check-in date in advance, and leave room for the person to reach the goal their own way.
Why is the “tap on the shoulder” a problem for schools? It rewards whoever is most confident or vocal, which carries built-in bias, and it promotes people into roles they were never developed for. Rebecca recommends replacing it with proactive career conversations across the whole staff.
How can a school start succession planning with limited resources? Start small. Commit to it, review your real hiring and retention data, pick one or two roles, draft a plan for each, and pilot it. Treat it as an iterative experiment rather than a grand program.
