It occurred to me recently that every boss I’ve ever had has told me at some point that I’m easy to work with. I’ve been thinking about why, and here’s what I’ve come up with. (To be clear, I’m far from perfect at this stuff; I just strive in this direction. Also, doing this stuff requires that you have a reasonably sane manager. If you don’t, then as always in that case, all bets are off.)
• Approach your work like a consultant and try to assess things from an emotionally detached place. That means, for example, responding to critical feedback about your work in the same way you’d respond to a problem that wasn’t connected to you — by gathering information and talking over options. (“Would it be better to do X?” “I think Y is happening because of Z. Let me try to do ___ and see if that solves it.”) It’s approaching it as collaborative problem-solving rather than as something sticky and emotionally charged. And speaking of feedback…
• Make it easy to give you feedback. That means soliciting it directly by asking questions like, “Should I handle that differently in the future?” and “Do you have thoughts on how I could do X better?” and it means not getting panicky when you get it. (See above; treat it as collaborative problem-solving, not an attack.)
• If your manager’s perspective is different from yours, focus not on persuading her to see it your way or on getting frustrated, but on figuring out why: What do you know that she doesn’t know, or what does she know that you’re not considering? The reason for your differing perspectives is probably in there.
• Work to get a good sense of what types of things your manager wants to be in the loop on — what she wants to be consulted on, what she wants to approve, and what she wants to be informed about. And if you’re unsure, don’t guess — ask directly so that you know.
• Keep your manager in the loop about anything remotely sensitive/awkward/controversial and how you’re handling it, so that there aren’t surprises later (for either of you — whether it’s her being surprised that Sensitive Thing X happened or was handled a certain way, or you being surprised afterwards that she doesn’t like the way you handled it).
• Accept idiosyncrasies with grace and calm. Every manager — every person — has at least a few weird preferences or pet peeves. Roll with them. Maybe your manager wants everything printed in Times New Roman 14 and you much prefer Arial 12. Make your case for Arial once and then drop it. Don’t snark to coworkers every time you have to change the font on something or try to sneak in Arial. And don’t make her feel like you think she’s ridiculous for it; roll with her preferences the same way you’d want your team to roll with yours.
• When your raise concerns, frame them from the perspective of “what makes the most sense for the organization and why?” rather than “I want X.” That’s the perspective your manager is going to need to take, so it’s better for both of you if the conversation starts there.
• That said, if something really just comes down to “I want X,” be straightforward about that too. If you have credibility built up from doing the other things in this list, sometimes it’s okay to say, “I understand that X doesn’t sound like a big deal, but it’s driving me crazy. Could we try doing ___?”
• When you’re confused or concerned by a manager’s words or actions, ask about it rather than letting it bug you and make you anxious. And don’t try to dance around it; just plunge right in: “I noticed you seemed hesitant when we were talking about X in the staff meeting. Do you want me handling that differently?” Or, “Last week when we talked about X, you said Y. I realized I wasn’t sure what you meant by that.” Or, “I might be misreading this, but do you have any concerns about how I’m handling X?” (The key: You have to say this stuff calmly and with genuine openness and curiosity. Sounding agitated would give it a completely different feel.)