When I worked at Shesh, 180 people reported 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 some things I needed to know to manage them effectively and make sound management decisions.

I am faced with a challenge that I have seen many times people in management struggle with: How can you distinguish between the information you need and the information you don't? Furthermore, how can you ensure that your direct reports are giving you the necessary information — and what information should you provide versus withholding when reporting to someone else?

Appropriate allocation requires case-by-case judgment

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

For example, let's say someone discovered a bug in the new software. That would have been something I should have known, but it would have raised other questions. How long had the case been ongoing, when was it going to be resolved and how serious was it? Knowing how much of these details to share and when to share them would be much more difficult.

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

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

Connected: The best communicators follow these 3 rules when speaking with those in authority

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

The main principle on which all my rules for sharing are based is very simple. In the case of my former boss, I decided that if she was ever asked a question about something in my domain, she should be able to talk to him.

Let's say there was a legal issue involving some European regulations. Did she need a 30 page file explaining the data? No, but I could reasonably assume she had to know we were on it and would update when she had a solution.

The most important thing for me was to make sure she never was caught off guard. That way, if she were asked about the matter at a shareholder meeting, she would at least be able to provide some insight into how the matter was being handled. She could also explain that one of her subordinates was handling the data, which would make perfect sense.

Questions to ask before sharing with your manager

The principle I described above is quite broad, so here are three yes-or-no questions I recommend everyone ask themselves when deciding to share information at scale:

• Is this something their manager might ask them about? The superintendent it's not helpful – your boss doesn't have time to read every line of code. But they need to know if there's a problem with the coding and who's in charge of fixing it.
• Is this a high value issue? Consider what your team has to gain by sharing the information (ie, perspectives or resources that can help solve a problem) and what you'll lose by not sharing it (necessary support, a second set of eyes, etc.).
• Does this have a wide blast radius? If you choose not to share something, how much harm can it cause? The point of asking yourself this question is not to catastrophize – but clarifying the risks in a given situation (even peripheral ones) is vital to insulating yourself and your team from them.

If you answered yes to all three questions, your manager needs to be aware of the issue so they can notify the appropriate parties, provide data as needed, and insulate the organization from potential risk.

Connected: Why the best managers ask more questions

Breaking up with a direct report also depends on your relationship

Making accurate judgments about when to split is an art form and takes some practice to get right. It's also very dependent on the personality of the person you're working with, which is why building relationships 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, abortions, 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 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. good.

Connected: Be a coach, not a referee – How to be a good mentor and manager from a coaching perspective