my boss keeps asking me to do things that aggravate our community partners

This post was written by Alison Green and published on Ask a Manager .
A reader writes:
I started working for a nonprofit last year. I work with our community partners a lot, and our director, “Fergus,’ likes to ask me to ask them for things without telling me they already said no. He’d tell you that he’s the kind of guy who doesn’t take no for an answer. Which is fine, I guess, but not the way he does it.
Two short examples:
1. My first week, he told me to email one of our partners, introduce myself, and ask them to do Favor X. I got back a very terse email with the partner with all the levels of their organization cc’d, saying they had already explained multiple times that they cannot and will not do Favor X. When I asked Fergus about this, he said he forgot asking them and they shouldn’t have been so “rude” (his word) in their response.
2. Our venue for a donor event fell through at the last minute and a local church agreed to host it. Unknown to me, they told Fergus that with other events, we had just a few hours to set up and clean up before and after the event. He sent me over there with supplies two days before to start setting up, which ended up with me having a very awkward conversation with the people there about how there was no way we could do that and they had already explained it to him. Fergus’s response was, “Well, they should have at least let you store the stuff there since you brought it over.”
So far I’m doing a few things. First, I’m recognizing red flags (if he asks me to contact someone I have no relationship with and he does to ask them to do something, that’s a red flag). I’m also prefacing my requests to people with, “Fergus asked me to ask you” — awkward, but true. And with something like the second example, I’m either asking him for more details like “what time did they say they were available for me to bring stuff over?” or being proactive and emailing to say, “Fergus said I should bring some of our supplies for the event over today, is 10 am good for you?”
But I get a LOT of no’s, and angry ones! Because they already told HIM no, and now I’m asking again.
I know I need to address this because working with our partners is a big part of my job and I’m pissing them off. Also, his reputation is … terrible. When I say “Fergus asked me to ask…” I’ve seen people actually roll their eyes in meetings. I don’t want to not do what he asks me to do, but he’s asking me to do things that are hurting our relationships with our partners.
Well, it’s going to get to the point where no one will be willing to help your organization at all, because Fergus will have used up all their good will and then some, and people will know that saying yes to him/your org means their boundaries will be trampled over. It sounds like some of them have already concluded that.
I think you’ve got to tackle this on two fronts: Fergus himself, and the way you approach the partners. You’re handling the partner piece well already — making it clear requests come from Fergus, and confirming details with them rather than taking Fergus at his word when he tells you something is okay. Keep doing that. Also, when people get angry that you’re asking them again when they already told Fergus no, you can be apologetic! It’s fine to say, “I’m so sorry, when he told me to contact you I didn’t realize you’d already spoken about it. We definitely don’t want to hassle you and I’ll relay this conversation to him.” (Obviously you can’t be like “yeah, he sucks” but you can agree they shouldn’t be hassled and indicate you’ll convey their irritation, which will politely separately yourself from him.)
On top of that, you should also talk to Fergus himself. At a minimum, every time someone is upset you contacted them, you should pass that on to him; don’t buffer him from it, and make it clear exactly how upset each person is. That’s information he needs; if community partners are frustrated with your organization, that’s highly relevant info that the the org needs to be aware of. (I’m assuming Fergus himself is the head — but if he’s not, someone above him definitely needs to hear this is happening.) You can also ask him more clarifying questions when he assigns you something — like, “so I have all the context, have you had any conversations with them about this yet?”
But you should also try talking to him about the pattern itself. For example:  “I’ve had multiple conversations recently with community partners who were upset because they felt we weren’t respecting clear boundaries they had already laid out for us — people who had told you no about something and were upset when you asked me to ask them again, or things like when Org X felt they’d made it clear we only had access to their space for a few hours. A lot of the people I’m contacting seem really fed up with us. I’m getting the sense it’s harming our reputation and they’re going to start saying no to us more often because of it.”
There’s a good chance Fergus won’t care … but it’s possible that by spelling it out like this, you might get him to check some of his worst tendencies. People who operate like this seem not to realize just how bothered people are by their behavior (they’re bad at picking up on cues or they think people won’t really mind after the immediate conversation ends, or they just have weird, miscalibrated norms), and it’s possible that you acting as a sort of interpreter — “no, they are very upset, and they are still upset even though two months have gone by” — will help nudge him toward a different framework.
But it might not. If not … well, then part of your job is doing something that you know is a bad idea. Some people can make their peace with that; some can’t. Generally it depends on how large a portion of your job it is and how bad the ramifications really are. If your whole job is to build relationships with community partners and Fergus won’t change, you probably need to move on because you’re being hamstrung in a fundamental way from getting the results you’ve been hired to achieve, and you risk blowback to your own reputation too. On the other hand, if it’s a smaller piece of your job and doesn’t come up a ton, you might choose to live with it and just focus on damage control.
I should add that in some jobs you’d have the option of just exercising your own judgment before carrying out Fergus’s requests — and strategically ignoring the ones where you can tell you’re going to annoy someone. That can be playing with fire, though; in some cases it can work beautifully for all involved, and in others it can get you fired (or one day you’ll end up ignoring a request that was actually really important). Either way, it might be helpful to ask colleagues for advice on working with Fergus; you might find out people have useful strategies for working around him.
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