On managing new (old) coworkers

Dear Plucky:

I recently started a new job as a manager and several of my team members are previous coworkers. One of the guys has a really bad habit of taking action without asking first or thinking through the strategy; this means that he has gone over my head to my new boss (perhaps because my boss is his former boss).

I know my new team members don’t want to be micromanaged but at the same time, I feel the strategic vision should be something I establish and convey to my team and boss. But as I am new to management, I really don’t know if that is an old way of thinking and I don’t want to make a critical mistake. What do you think?

New Sheriff in Town

Dear Sheriff,

What a nuanced question. First of all, cheers to articulating a complex dynamic… old coworkers, new coworkers, promotion into management AND skip-level authority issues?! I need to pour some more coffee.

(Jen goes away and serves herself more coffee.)

Ok. So a few things occur to me here:

1. You’re in a trust building phase with your previous coworker (now your Report), so this is going to take some time and patience. Even when we have worked with someone in a prior job, the dynamics around a different culture, new competition and unknown authority structures require that we begin again. Have you ever heard the St. Benedictine quote, “Always we begin again”? It is so true.

“Always we begin again” is a solid mantra when joining a previous coworker on a new team, in a new company or through a new role.

Since you’re laying a foundation of trust, spend time observing the politics and dynamics for these first few weeks (if you haven’t already). Pay attention to how this Report ticks in this new company. What is he afraid of? What is he proud of? How is he challenged? How is he succeeding? All of this information is relevant — and spending a few 1:1s on these topics can illuminate his current work landscape so that you can best manage him.

2. Interestingly, there are two lines of trust for you to build in this scenario — one with your Report but also with your Manager. So let’s talk about that.

Since you’re inheriting the Report from him, it would be good to sync up to get his impressions and feedback about the team. (I imagine this conversation as two doctors meeting as one’s shift ends and the other’s begins. It’s important to give some high level status updates about the Reports in your care).

While you’re getting his perspective, feel free to ask him for some advice. You might say “so I’m taking over some of your previous Reports and I want to be both respectful of the relationships they’ve built with you AND make sure my role is empowered to hold authority. What’s your guidance for how we keep lines of authority clear with them?”

What you’re doing by asking that is reminding your manager that “HEY! Push back when this dude comes directly to you… remind him to follow the org chart” without being so explicit. If he’s a good manager he will appreciate the opportunity to co-manage this transition with you, especially because you are being so thoughtful and professional about it. Make sense?

3. Now let’s talk about the Report’s over-enthusiasm for taking action. This sounds like a perfect area of growth to identify with him and work on over time.

Tactically, if he comes to you with a new idea that he’s vetted through your manager, feel free to say “ok, well let me sync up with [Manager] about that and I’ll get back to you. I definitely want to be in the loop on things like this!” That’s a gentle reminder of org chart and responsibility too. So long as you’ve done good trust building with your Manager, this will clear up shortly because you’ll both be continuously routing him through the chain of command.

So to wrap: begin again with your Report. Build trust with your Manager. Invite the Manager’s perspective on the team and ask for his partnership in delegating you the authority for the Reports. Tag team the chain of command until everyone knows the new way of doing things…

At which point, let’s be honest, someone else will quit or be hired and you’ll somehow have to start again, a la Benedictine. WELCOME TO MANAGEMENT! It’s a wild west out there… but the victories are deep and sweet.


Are you a manager? Have you ended up managing a previous coworker? Join us for the next So Now You’re a Manager training. We’re going to talk about it all, normalize modern managing and help you find your way through it with a bunch of new friends.