Hard Conversations with Peers

A cat lying in an office chair stares at the man perched on the front edge of the chair working
Sometimes that coworker just isn't taking the hint

A real-world factor in hard conversations is the relative status of you and the person you’re talking to. Every social group has formal and informal hierarchies, and taking that into account increases the odds of a hard conversation going well. I’ve teed up three articles about this, each focused on a different status: peers, people in power, and people who work for you. Today I’m starting with specific things to consider as you’re preparing for a hard conversation with a peer. If you want the TL;DR before diving in, here's a three line summary.

There’s lots of reasons you might need to have a hard conversation with a peer. Maybe you're an engineer and the new engineer’s comments on your code are nitpicking and patronizing. Maybe you’re a product manager and your product marketing counterpart never has time for you and your very important product. Maybe you’re a manager and another manager is making things hard for your team.

Going back to our discussion on assuming positive intent, my first bit of advice is to take a moment to be ridiculously clear about your understanding of terms and norms. This is especially important when crossing team boundaries, but even within a team you might not have normed around all the things. For example, that nitpicking engineer might have come from a company where every detail mattered, but your team limits reviews comments to things that are a major concern. Communication norms can also be cultural, whether people are from different countries, or just opposite coasts of the U.S. A few years ago I was in my first in-person meeting with a coworker from another office. She was so aggressive I thought she was angry and I knew the meeting wouldn't go well if I didn't figure out why. So I paused the meeting and said, "I know we don't know each other but you sound really mad and I don't know why. Can you tell me what's going on?" She was surprised because she didn't think she was being aggressive at all. In her view, she was just excited about our new project and wanted to get on with it. Then she laughed and said she was from New York and forgot she was out in Portland and needed to dial it down a notch. We got along great after that and I loved her style once I knew how to interpret it correctly.

In addition to behavioral norms, different definitions for common terminology can also trip people up. I gave some examples of this in the article on assuming positive intent.

The second thing to think about, especially if you’re crossing functional boundaries, is that the other person may be operating under a very different reward system. This includes everything from their actual paycheck to wanting to look good to their boss.

Once when I was a product manager, I was shipping new features that I wanted to be discovered and used by our customers. I never seemed to be able to get any help from my product marketing counterpart. Then I found out that she and her team got quarterly bonuses based on leads generated, i.e. contacts who might become new customers. Aha! We had very priorities. Once that clicked, while I couldn’t change it, I knew where I could expect help, how to better help her, and what I needed to do myself. And we got on a lot better, too.

Here's a different example from my product manager days. An engineering manager I worked with kept declaring new features I’d specified done and moving on to new work, but I knew the features weren’t really done. They didn’t meet the specs or pass user testing. After months of conflict and trying to get rework prioritized, I finally had a conversation with him that revealed that his boss valued declaring work done and gave him the leeway to ignore parts of the spec he didn't think were important in order to “keep shipping.” This turned out to be at the root of a lot of what I thought were communication problems between me and the team. The real problem was that our bosses weren’t aligned on what was important. That gave me a whole different problem to solve, but one that actually got to the root of things.

Here’s my last piece of advice on having hard conversations with peers. You’re going to be tempted to outsource this conversation. You’re going to want your boss to deal with this, or maybe the other person’s boss, or someone else more senior than you. Don’t do it. (If you’re you’re dealing with harassment or other safety issues, that’s an exception to all of this. Get all the help you can.)

Don’t try to outsource the conversation until you’ve given in a real try. It may not work, but that’s OK! Because when you ask for help after you’ve given it a try yourself, you are going to improve your creditability, your reputation as someone who gets things done, and even your ability to get help. Plus, some finite and non-zero percentage of those conversations you thought were lost causes will turn out fine. You can do more than you think with just one honest, altruistic, curious conversation with a peer. But if it doesn’t work out, and you then ask for help, your boss is going to be impressed and grateful that you gave it a go. They’re also in a better position to help because probably the first thing they were going to do was ask you, “have you already talked to this person about this?”

OK, because I’m being such a hard-ass on this I’m actually going to give you another option. If you really don’t feel ready to have the conversation, do your prep work and THEN go ask your boss for help. Say “I want to talk to this person about this thing, and here’s how I’m thinking about approaching it. I’m kind of nervous about it, though. Can you help me figure out if I’m missing anything and get ready to have this conversation?” Because you did the work and you’re showing the courage to have the conversation, your boss is going to appreciate that you’re not just throwing a problem in their lap. Usually one of two things happen, assuming you have a halfway decent boss. One is they help you and you go in better prepared and also feeling like someone’s got your back. And when it’s over you’ve got someone to debrief with: win, lose, or draw. 

The other thing that might happen is that your boss might wave you off. Maybe they know about other things going with this person, team or department and they are working to resolve a bigger issue. So then you get all the benefits but don’t have to do the hard thing ;). Be curious here though. Is your boss just afraid of conflict or are they really trying to solve things? Ask what the timeframe is for a resolution. Clarify how you’ll handle this problem in the meantime and do your best to leave the conversation with a concrete plan. If your boss says they just can’t afford to have the pot stirred at all right now they really might be right, so if they’re generally a reasonable human being give them the benefit of the doubt and just focus on how to work around the issue indefinitely. If this is just the latest example of how they’re a gutless wonder, well think about whether you like the rest of your job enough it balances out. 

Summary

That was a long one so here’s a summary of three tips for having hard conversations with peers: 

  1. Clarify terms and norms
  2. Understand how other person is rewarded
  3. Don’t outsource

Your Dot Release: If you don’t have a hard conversation at hand, you can still practice the first two tips in your next conversations with peers. Pick two people you work with regularly and take a few minutes to explicitly define some key terms and compare your definitions of success. It will be a good chance to learn and improve an important relationship and you’ll have some practice before your next hard conversation.  

Release Notes: Two cool things to share with you this week. First, I wrote an article about bragging for the inspiring Certain Age Magazine. It’s a less work focused take on the power of bragging to illuminate our stories and I hope you’ll share with folks who might find it interesting. 

And for Portland people: I’ll be facilitating a session on bragging for product managers at the Portland Product Tank on January 28. Jack Hott will also be talking about a practical use of Generative AI. I’m excited for both sessions as well as the chance to hang out with product folks. Event info and registration (it’s free!) are here: https://www.meetup.com/producttank_portland/events/305468076/?eventOrigin=your_events

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Jamie Larson
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