When Your Boss Doesn’t Delegate: How to Earn Their Trust (and Stop Them From Micromanaging Everything)

If your boss doesn’t delegate, you’ve probably noticed two things: they want to supervise absolutely everything, and they change things you’ve already organized.

Have you ever scheduled a meeting after juggling impossible calendars, only to have them reschedule it in their own calendar without telling you? It’s frustrating—not just because of the wasted effort, but because it undermines your ability to plan and keep control of the schedule.

Managers like this don’t always behave this way out of personal distrust. Often, it’s simply their work style: they feel only they can guarantee that everything is “perfect,” or they don’t want to lose control over anything that involves them directly.

(real example) In a previous role, my boss would review and reschedule meetings I had already confirmed with several directors. At first, it annoyed me, until I realized that I needed to prove I could anticipate changes and think like they did. Gradually, I started incorporating their decision-making criteria into the calendar proactively, and eventually they began to respect my scheduling without changing it.

If your boss supervises everything, the key isn’t to fight it—it’s to integrate it into your way of working. This means:

• Learning their preferences in detail and applying them from the start.

• Communicating the reasoning behind each decision, so they see there’s thought behind it.

• Giving them visibility before finalizing something important: “I’m planning to schedule the client meeting for Thursday at 3 PM—does that work for you, or would you prefer another time?”

It also helps to anticipate their moves. If you know they tend to reschedule certain types of meetings to avoid overlaps, take that into account when booking them in the first place. This reduces the chances of them making changes later.

Finally, celebrate the moments they don’t intervene. If you scheduled something and it stayed exactly as you planned, acknowledge it: “Glad the Finance meeting stayed as scheduled—it seems to have fit well into your week.” This reinforces the habit of trusting your planning.

Ultimately, if your boss doesn’t delegate and micromanages everything, your best tool is to build trust by understanding their preferences, anticipating adjustments, and communicating clearly. Over time, they’ll delegate more and feel confident their standards are being met—without having to move every piece on the board themselves.