Trusted Deputies
As you rise in an organization, your success depends less on what you do and more on the people you trust to help you get it done.
When you first become a manager, you can see everything. The work is right in front of you, and it’s easy to keep in touch with your small team. You know where you stand. But as you rise up the ranks, it gets harder. I experienced this abruptly when, after managing teams of roughly five people, I took a senior leadership job managing eighty-five.
It was at that point I became acutely aware of the importance of what I now call “trusted deputies.” It took me a while to get them in place—some were already there and were great, some were not. When I did, it changed my life and the lives of my team members as well.
Why deputies matter
The bigger the team, the harder it is for the leader to exercise direct oversight and influence. This begins the moment you become a manager of managers and only intensifies as you rise. Your role shifts from functional to managerial. You can no longer do the work yourself; you have to ensure others do it well.
So how do you make sure the team delivers independently and to a high standard? You find people to help you. People who can manage a portfolio of work and people with near-complete autonomy and still hit their goals.
There are two ways you’ll recognize you need a trusted deputy. One is that the role already exists in the org chart: there’s a clear function being managed by someone, and you need to know if that person is up to it. The other is that you feel the pain of the role’s absence—you’re spending an inordinate amount of time personally performing the function. This usually happens during a deliberate transformation or a period of significant growth.
What to look for
Assuming someone is already in the role, assess their capabilities along three dimensions:
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Functional success. Are they effective in the role? Are they meeting their goals?
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Bigger picture thinking. Do they work with their heads down, or can they participate in strategic discussions—how goals are set, where the business is headed, what tradeoffs matter?
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People management. What’s their management style? Do they motivate their team? Does the team respond to and enjoy their leadership?
The first two are standard competence. It’s the third that might matter most. Trusted deputies need to be more than functionally capable—you want them taking the same careful and nurturing approach to their teams that you take to yours. You can’t build a culturally aligned organization without this.
Building trust
The way trust gets built is by setting expectations clearly—then following through on both sides. I call this the Central Axiom of Management:
Management is the grant of autonomy in exchange for visibility.
Autonomy means the person doing the work gets to decide how it gets done, as long as it gets done. But that doesn’t mean you close your eyes. The deputy provides visibility into how things are going—through updates, check-ins, and results. Over time, this exchange creates the building blocks of trust.
What happens when it works
It can take a while to build your corps of trusted deputies. Not everyone is ready from day one. Some need coaching and then rise to the occasion. Some aren’t fit for the role and need to be replaced—yes, replaced, because you cannot afford underperformance in your leadership team.
But as the group improves, something remarkable happens. Your deputies start working together even when you’re not looking. The team builds its own cohesion, focus, and alignment. In my experience, the best teams develop to the point where they regularly outperform their targets and carry a genuine feeling of pride.
The multiplier
The real payoff isn’t just that you get your time back. It’s that, over time, the investment compounds. Trusted deputies go on to create more trusted deputies and team performance and satisfaction skyrocket. That’s how great teams scale.

JD Deitch
B2B SaaS operating executive specializing in post-deal execution and operational scale for PE-backed companies.
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