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Should I Tell My Boss About This? This is How to Balance What Your Direct Reports Do (& Don't) Need to Know Understanding what your direct reports do and don't need to know ensures smoother communication and leads to better outcomes.

By Darian Shimy Edited by Micah Zimmerman

Key Takeaways

  • The better you and your mentees know each other, the more support and freedom you can give them to take risks that allow them to grow and become better.

Opinions expressed by Entrepreneur contributors are their own.

When I worked at Square, I had 180 people reporting to me. It would have been impossible for me to know the details of every single task they performed on a daily basis. But there were also certain things I needed to know in order to manage them effectively and make sound leadership decisions.

I faced a challenge I've seen many people in management struggle with: How can you tell the difference between the information you need and the information you don't? Moreover, how can you make sure your direct reports are giving you the necessary information — and what information should you provide vs. hold back when reporting to someone else?

Sharing up appropriately requires case-by-case judgment

Some of the things I needed to know from the people who reported to me were obvious: if one of them quit, for example, or if there was an HR issue. But other cases were far less cut-and-dried.

For instance, let's say someone discovered a bug in the new software. That would have been something I needed to know, but it would also raise other questions. How long had the issue been going on, when will it be resolved, and how severe was it? Knowing how many of these details to share and when to share them would be far more difficult.

Later, when I had a new boss, I found myself on the other side of the coin. How could I make confident and accurate decisions about what she needed to know from me?

To help me make these judgment calls, I developed a framework supported by a simple (but important) set of questions. I've shared these below so that you can adopt this framework for dealing with your direct reports and share it with the people who report to you.

Related: The Best Communicators Follow These 3 Rules When Talking to Those in Authority

The rule of thumb is to never leave your lead in the dark

The overarching principle that all of my rules for sharing up are based on is pretty simple. In the case of my former boss, I decided that if she was ever asked a question about something in my domain, she needed to be able to speak to it.

Let's say there was a legal issue involving some European regulations. Did she need a 30-page dossier explaining the particulars? No, but I could reasonably assume she needed to know we were on it and would update her when there was a resolution.

The most important thing for me was to make sure she would never be caught off guard. This way, if she were asked about the issue in a shareholder meeting, she would at least be able to provide an overview of how the issue was being addressed. She could also explain that one of her subordinates was handling the particulars, which would be perfectly reasonable.

Questions to ask before sharing with your lead

The principle I've outlined above is fairly broad, so here are three yes-or-no questions I recommend everyone ask themselves when deciding to share information up the ladder:

  • Is this something that their lead might ask them about? Oversharing isn't helpful — your boss doesn't have time to read every line of code. But they do need to know if there's an issue with the coding and who is on top of the fix for it.
  • Is this a high-value issue? Consider what your team has to gain by sharing the information (i.e., perspective or resources that could help solve a problem) and what you stand to lose by not sharing it (needed support, a second set of eyes, etc.).
  • Does this have a wide blast radius? In the event that you choose not to share something, how much damage could it do? The point of asking yourself this question is not to catastrophize — but clarifying the risks in a given situation (even the outlying ones) is vital for insulating yourself and your team from them.

If you answer yes to all three questions, your lead needs to be aware of this issue so that they can notify the appropriate parties, provide input as needed, and insulate the organization from potential risk.

Related: Why the Best Managers Ask the Most Questions

Sharing up with a direct report also depends on your relationship

Making accurate judgments about when to share up is an art form, and it requires some practice to get it right. It's also heavily dependent on the personality of the person you're working with, which is why relationship-building in the workplace is so important.

I'm a big believer in sharing experiences. During my 11.5 years at Square, the people who reported to me had marriages, divorces, miscarriages, home purchases, legal issues, substance issues, long-distance moves and more. I knew all about them.

Why? Because those things affect how a person works and what they bring in from one day to the next. Not every manager works this way, but I do. I don't believe in micromanaging, but I do believe that the better you and your mentees know each other, the more support and freedom you can give them to take risks that allow them to grow and become better.

Related: Be a Coach, Not a Referee — How to be a Good Mentor and Manager from a Coaching Perspective

Darian Shimy

Entrepreneur Leadership Network® Contributor

Founder and CEO of FutureFund

Darian Shimy is the founder and CEO of FutureFund Technology, a fundraising and selling platform for K-12 school groups. He has 25+ years in web-based technologies and managing engineering teams.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

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