How to Listen to People

I spent a year as the engineering site lead for Puppet’s Portland office. During that time it was my job to be the executive point of contact for any engineer, designer, or writer in our software development group. That meant that I was spending a lot of time fielding issues people were having with their team lead, line manager, or director; or I was trying to unkink operational gaps.

I’d always considered myself a good listener, but came to realize that perhaps I wasn’t an effective listener.

I went into that year as more of a fixer, imagining that my job was to give advice, or take care of problems for people if they couldn’t follow my advice. As the year progressed, the way I assessed my own effectiveness as a leader and a listener evolved. I spent less time giving advice, I measured the success of a given interaction by how much less I said than the previous one, and I shifted from offering to intervene to offering help with developing a strategy for a difficult situation or conversation the person I was listening to needed to handle for themselves.

Every now and then, you come across a phrase that helps you make a shift. That year, I came across this one:

“Listen like you don’t know the answer.”

I once had a boss who always anticipated the problem I was bringing to him, finishing my sentences then jumping to his personal playbook to offer a solution. Because his playbook was his playbook, built up over years of him solving problems with the gifts and tools particular to him, it didn’t do me a lot of good.

The great thing about that relationship was that I eventually learned to say, “I don’t think that will work for me,” and I’d explain why, and he’d settle into a more constructive, conversational mode, helping me break down the problem and figure out how to solve it in a way that worked for me.

When you’re in the listening leader role in a conversation, you become a lot more accessible when you listen without judgement, or without conveying the sense that you’ve seen and done it all, or that the problem someone is experiencing is trivial.

Over that year, I developed a set of principles. After moving on from that role, a senior leader in the company came to me and told me that people had told him they considered me an effective listener, so he asked me to give a presentation for other managers.

Below is an outline of that presentation.

People deserve to know their choices. Focus on that instead of fixing things. 

Nobody likes it when people who do good work leave, and some people don’t even like it when people who do mediocre work leave. During a time when there’s a lot of focus on attrition or concern about morale, people will sometimes soft-pedal bad news, avoid making hard decisions, or try to defer unpleasant or hard conversations to keep everybody happy. 

When you do that, though, you’re just kicking the can down the road and possibly withholding what people who are genuinely unhappy need to get “escape velocity,” make a decision, and move on. 

Don’t withhold in the hopes they’ll just calm down for a while. If they’re faced with a situation that simply isn’t going to change, they should know that, whether it’s “that’s not how we work here anymore,” or “we’ve made that decision and aren’t revisiting it.” 

Anything less is just allowing them to stay in a state where they think something will change that won’t, and it’s keeping them from making a better decision than “hang around until the thing I hate goes away.” 

You’re having these conversations because there are strains in relationships, and you should be working to make those relationships whole again

Ideally, you’re giving them someone to talk to, and encouraging them to take their problems to the person best equipped to solve them as they’re able to get enough perspective to do so. You engage in constrained and discrete action or intervention as a last resort. 

In other words, the interactions you’re having with any given person aren’t the desired end-state: It’s an interim situation. 

Some rules

You have to sit and listen

It’s tempting to come to think of yourself as a fixer, whether it’s of a broken manager/report relationship, a system or process, or even just someone’s faulty perspective. 

When someone first agrees to sit down with you and tell you what’s going on, though, the thing they’ve asked you to do in that moment is listen. They might ultimately want you to fix something, and the hope that you’ll fix something is probably part of why they’re sitting there talking to you, but in that moment the thing they want you to do is listen. Their problem probably feels unique to them, in the particulars if not as a general kind of problem. Something about it feels like it’s outside their experience or ability to handle, or they’re simply not sure what their expectations should be. 

Just listening can be pretty hard. You might have some idea of what their problem is before they even begin to speak. You might be able to see where they’re going before they get very far in to what they have to say. It’s important to let them talk it out: They need to talk through their feelings and they’ve asked you to help them do that. Sometimes they’ll even talk themselves into a solution or end up better understanding what they want to ask for. 

You don’t always have an answer, and you need to admit to that

Sometimes you don’t know. It’s okay to say you don’t know and need to go learn more. 

You have to learn how to find the balance between acknowledging their feelings and being part of a management team

Sometimes, you’ll believe another manager made a mistake in their handling of a situation. The times that’s obvious and clear-cut are pretty few. More often, there are a bunch of perspectives on the problem. In some ways, it just doesn’t matter: Your primary function in the moment someone has brought a problem to you is to listen. (If they’re reporting unsafe behavior or a violation of policy, you definitely need to escalate.)

It’s still possible to show empathy and kindness without making comment on a colleague’s decisions: 

“How did you feel when they said that?”

“How do you feel now?”

“I understand that didn’t feel great. Looking at it from your perspective, I’m not sure I’d like that either.” 

You can’t ambush your colleagues with the things you learn

To most good managers, having a good understanding of the dynamics on their team and the state of the people on the team is essential to their professional self-respect. When it turns out they’ve missed a situation, or they’ve just learned that one of their folks is having problems without bringing it to them first it can feel embarrassing. 

One way to make sure people are in a good place to take in what you’ve learned about a situation on their team is to share it with them discreetly, not around a meeting table where they’re hearing about a problem at the same time as everybody else. If you use information you have about their team dynamics or one of their employees to show them up or contradict them, all you’re doing is creating resistance to finding a solution. 

You’re listening to everybody, but you have a network and need to acknowledge that

Even if you’re touching base with a lot of people, you probably have a few people you talk to most. They’ve got a particular perspective and while they may be pretty key and influential people, it’s still just their perspective you’re hearing. 

When asked “what’s going on on the floor,” acknowledge that: “The folks I’m closest to are saying this but I’ve also heard that.” 

A Workflow

When someone needs to talk, there are a few things you have to do: 

Listen

Just listen. Try not to say much outside the usual “active listening” stuff:

“What did you do next?”

“What went through your head when you heard that?”

Stay off your phone and stay out of your laptop, or set an expectation (e.g. “my son needs to call me from school this afternoon so I’ll have to pick up my phone when I get a notification.”)

Play it back

Once they’ve told their story, playing it back to them in a few sentences shows them you were listening and helps ensure that you’ve actually spotted the issue. You may have missed it, especially if you went into the interaction thinking you already knew what the problem was. 

Just play it all back in a few sentences, and make sure you got it all:

“What I heard was a, b, and c. Did I miss something in there?” 

Keep your own emotion out of it

Sometimes people bring some stuff that’s frustrating to hear. A lot of strong emotion from an authority figure can put people on high alert, or cause them to shut down. They’re often afraid they’re going to trigger some sort of reaction out of proportion to what they were hoping for. It’s not wrong to show empathy, or say “I can see how that would be upsetting,” (or frustrating, frightening, etc.) but don’t take on their emotions (that’s bad for you) and don’t make a big display of your own anger or frustration (they’re there for help, not to watch you process your own emotion). 

Let them know what they can expect

I always make clear their story stays with me unless there’s a policy, legal, or safety issue. Some managers don’t like that, but it’s one way to insulate the person doing the listening from being turned into a back channel: If the employee was hoping for that back channel, they know they won’t get it. 

Call it out when what they saw was wrong or unusual

Sometimes, you’ll learn of things that are plainly unprofessional or inappropriate. It’s not wrong to offer an opinion. Just make clear that it’s your opinion. 

I once dealt with an employee whose manager a. claimed that there were secret criteria for being promoted that he couldn’t tell her and she hadn’t met; and b. told her teammates she wasn’t mature enough for promotion. 

I called those things out as a. untrue and b. inappropriate. I made clear that she had an expectation of confidentiality around performance conversations, and that the behavior wasn’t normal for managers at Puppet. 

Ask for permission to raise the issue with people who can fix it

We don’t want to be used as back channels for manipulation, and it also reassures people there asking for help with problems they can’t resolve that they won’t get someone in trouble or “call down the thunder” when they aren’t even sure there’s really a problem. 

Set expectations

Tell them:

  • Who you’ll talk to, if they’re okay with that
  • What you propose as a next step
  • What you’ll do next
  • When they can expect to hear from you

Follow up right away

Let them know once you know something useful, whether that’s “this is fixed,” or “I can’t do much more here, but here’s who probably could …”


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