Managing When You’re In The Middle

A reader asks:

I manage a staff member who frequently works on projects with our executive director, who’s my boss. It doesn’t seem like a good use of anyone’s time for me to just be a go-between for them, and I don’t want to be in the way of their communications. But I do want to be in the loop and be well positioned to spot and resolve problems and give my staff member feedback. How do I approach this?


The key to managing well from the middle is to focus on how you can best help the two “ends” – in this case, your staff member and your own manager – get what they need from each other. Here are four tips that will help you navigate what admittedly can be a tricky role.

1. Bring the questions you’re grappling with to the surface, and talk with both sides about what would be helpful. Don’t feel like you have to figure this out all by yourself. Instead, be transparent with both your staff member and your manager that you’re trying to figure out the most helpful role for you to play on the work they’re doing together, and ask what would be most helpful to them. You might also talk explicitly about what you see as potential pitfalls (such as messages losing some nuance in translation if everything is funneled through you or – if you’re not in the loop – you potentially delegating projects that conflict with higher-priority work your staff member is doing for the ED) and discuss how all three of you can avoid that.

2. You don’t have to be in every conversation just because you’re the manager. Managers in your shoes sometimes feel like they’re supposed to be involved in every conversation about every project that your staff member and your ED work on together, but that might be unnecessary or impractical. Instead, think deliberately about which conversations are the most important for you to participate in. For instance, you might sit in on the kick-off meeting for a new project, so that you’re all aligned about the project’s overall vision, desired outcomes, and the basic work plan. But there might be no need for you to participate in progress meetings or conversations to hash out nitty-gritty details. (Plus, if you can’t trust your staff member to meet alone with the ED and get the details right and follow through on what was agreed to, then you probably have a bigger problem.)

3. Your job might be to spot when to bring the two ends together, and to find ways to do that. Because you probably talk with your manager and your staff member regularly, you might start to feel like a conduit of information between the two of them. While sometimes this is the most practical or efficient method of moving work forward, part of your role is to spot when they should be talking with each other. For instance, if you observe that your staff member is unsure about how to handle a particular situation or can’t move work forward until she gets information from your manager, your role might be to flag it for your boss and suggest that they have a quick meeting or phone call. You also might be ideally positioned to spot it when they have differing assessments of a situation or are on different pages about how to advance a project, and – again – to flag it and suggest they connect about it.

4. Be explicit with your staff member that part of her role is to build the confidence and enthusiastic support of her “customer.” Occasionally you might have a different assessment of your staff member than your manager does. This can be especially tricky when you’re happy with the staffer’s work but your manager isn’t. It’s important to keep in mind that part of the staffer’s role is to build the confidence and trust of her “customers” – in this case, your manager. For example, we once worked with a VP of Development whose assistant worked closely with the ED on donor outreach, leading the ED to periodically complain about the assistant’s attention to detail. The VP thought the assistant’s work was fine, but the ED became increasingly reluctant to rely on the staff member’s work. Ultimately the VP – who had originally dismissed the ED’s concerns as being overly picky – came to realize that earning the trust of the ED was essential to the assistant’s job and that she needed someone in the role who could do that.

Whenever you’re managing someone whose success depends on gaining the support of an internal customer, it’s helpful to be clear about that expectation up-front and to define it as a critical piece of the role.