A Surprising Way Managing Has Made Me A Better Tech Lead, Part 2

This is Part 2 of the story that begins here. The points explained here are the ways in which I should have handled my first intern’s sub-standard performance. It was the first time I needed to give tough feedback to someone and I failed — massively. Described below is what I wish I had done. This is how I’d handle the same situation today.

Good Feedback Starts From Clear Expectations

The very first thing that should have happened is that I should have set clear expectations. Looking back, I see I didn’t set expectations clearly at all. I expected my intern to understand that the expectations were high and to work very hard to achieve them. When he wasn’t doing that, I didn’t let him know that he wasn’t meeting expectations. But even if I had tried, say a month in, to have a hard conversation, it would have been a conversation on very squishy ground. Because I didn’t tell him upfront what he needed to achieve to make the grade. Without that backstop, the truth was arguable.

A funny thing about high expectations is that when they’re clearly set, it can completely change the conversation. We had regular catchups where I continually asked him why he hadn’t learned basic Git commands yet and he made excuses. What if I had told him frankly that if he doesn’t master the basic Git commands, he would be failing our expectations? Perhaps he would have come to me ready to explain the work he’d put in to learn them, because the expectation was explicit. I thought people behaved like amateur psychics about expectations and I thought this kid was the asshole for not doing that. Maybe he was, but I also didn’t make things black-and-white for him when I could have.

Good Feedback Happens Immediately

I waited six weeks to tell my intern that he was failing. I suspected he was failing by day two and I had no doubt he was failing by his second week. I didn’t give him feedback because I thought it should be obvious to him. That he should intuit that he was failing and fix himself.

Every day you don’t give feedback, the problem compounds a little.

Trying to explain to him that he was causing problems for other teams was so much harder when he’d spent three weeks doing work he thought was awesome. When I finally did give the feedback, none of those situations was top-of-mind. We were in the Twilight Zone of human memory and re-interpretation. Now, as a manager of many people, I never wait for things to go stale and fuzzy. I should have had small, direct chats with him day-by-day letting him know when things weren’t working out. He might still have argued back or made excuses, but I’ll never know that because I didn’t do what I was supposed to do. It’s much more likely that he would have responded positively to at least some of the direct feedback, improved, and then begun trusting my feedback even more deeply.

Another reason feedback has to happen quickly is because if you let it fester, you’re much more likely to trigger shame in the person you’re giving feedback to. My intern felt proud of his experience. He felt cool because he was working on high-profile product initiatives. When I waited weeks to give him tough feedback, I took away some of that pride. I undermined that sense of self-worth. When you take something that precious away from someone, you really mess with them. You totally ruin the trust between you, too.

Good Feedback Starts From a Balanced Emotional State

Looking back, I can see that I really resented my intern. He had made it to Facebook as an intern through nepotism. He took it for granted. I cherished those early years. It was a life-defining transition point for me. And he was smugly wasting the real opportunity to learn and grow while simultaneously marching around like he was doing big things on high-profile teams. He was doing everything that I would hate myself for doing. It’s easy to see those feelings in myself now. 26-year-old me had no ability to connect with those feelings.

If you don’t understand your own feelings, you can’t give balanced feedback. I couldn’t see my intern for who he was because I was battling with my own emotions. My own brutality. I gave him feedback that crushed him because I thought that’s how it was supposed to work. I thought he deserved it. In hindsight, I was giving him feedback on who he was as a human, rather than what he was doing as an intern. Pretending like I was addressing one thing when I was actually addressing something different — something much deeper — was pure poison.

What I should have done is look at what was going on with him. He was both proud and insecure. Keen to show off, but scared to work hard. I clocked this as arrogant laziness. Now, I look back and I think… no — it was insecurity. I think my intern had learned to hide his insecurity by being aloof. Too cool for for school. I think he showed me ennui because he couldn’t bring himself to show his own fears or doubts. Likewise he didn’t want to get caught trying hard and failing, so if he sensed danger, he would stop trying.

What did I do to help him here? Nothing really. In fact, I’m pretty sure I just made all of those worse. I’m pretty sure any anxiety he felt about his own abilities was only made worse by the way in which I’d shamed him.

I could have built rapport with him. I could have shown him my own insecurities and made it safe for him to bring his out. Shown my self-doubts, defence mechanisms. But I didn’t. I wasn’t balanced enough to do that. So, my feedback to him was all wrong. Instead of seeing if there was a way to bring him out of his false-flag bravado, I pushed him further into it.

How I Handle Things Today

The upshot of continued existence is that you get to try again. And again-again. Now, with multiple years of people-management under my belt, I approach things way differently when tough feedback is required. Say, for instance, that one of my team members isn’t doing the right thing. For a contrived example, let’s say he’s causing trouble for the team by focusing his time on a pet project rather than on the parts of the system that need to get done most urgently.

The first thing I do is check in with my own feelings — the light and the dark. You see, we all have a little Rey and a little Kylo in us. If you pretend you don’t have any Kylo, you’re likely hiding something from yourself. So, when I’m tech leading a project and someone isn’t doing the right thing, the first thing I do is check in with myself about what I really feel. If I think the engineer is being selfish or egocentric, I give myself permission to have that feeling outright. If my spidey sense has detected that the engineer isn’t bringing a serious level of focus or urgency to the work, I give myself permission to feel resentful about that. Parents know these emotions. When a 3-year-old is being an absolute asshole… for the fifth time… today… every parent is irritated. Every parent hates that little shithead a little bit. They let those feelings come, let them be felt, and then let them go. Tech leads and managers have to learn the same skill.

Next, I try to look at the situation from the other person’s point of view. What are they thinking? What are they feeling? Beneath any bad behaviour is usually some misguided good intentions. Maybe they’re disconnected and aloof because they’re frustrated with their work. Maybe they’re insecure about being good enough to meet expectations. It could be all sorts of things. What I find is that unless I’ve accounted for all the big emotions inside myself, I can’t really see the other person clearly. If I’m trying to hold back a sense of resentment, I can’t really be compassionate toward the other person. When I’m able to quiet my own background-emotional-radiation, suddenly I see a much more complete human in front of me. When I give compassion to myself, I can suddenly extend it to others.

Once I have a sense of what they’re experiencing and what might be behind their bad behaviours, I look at what needs to happen. What specific outcomes do I need to bring to bear. My management style is about teaching people to fish while giving them real chances to fish. If our team has a tight deadline or a pressing scalability challenge, I might settle for specific technical goals, but in general I want to help the other person see the situation more clearly and enable them to make good, independent decisions themselves. This builds much stronger teams and much more capable team members. So, almost always, I try to figure out what context the other person is missing that’s leading them to contribute counterproductively to the team. Some of this is guess work, but often just taking the time to consider what they might be feeling is enough to help me give good feedback.

Then I have a chat as soon as possible. I don’t wait a week. If I can manage it, I don’t even wait a day. I find some time for a private chat ASAP. When it comes to giving tough feedback, I also never do it in writing first. Not over Slack. Not via Email. Not even over a Zoom call if I can help it. Being able to read the other person’s emotional response is crucial for giving tough feedback. It’s far too easy to get stuck in a fifty-message-long Slack message thread where the other person just doesn’t seem to be getting it. Often in cases like that, the problem is that the real conversation is one level deeper, but you don’t have the rapport or the signals to detect it. Maybe they’re being difficult because they feel anxious about something that they haven’t said. Maybe they’re just tired or distracted and you can’t tell that because you can’t see their face.

When it comes to giving the feedback, I make it clear that I am in fact giving feedback. I say something like, “I need to give you some feedback.” Or, “I need to put something on your radar.” It’s important to give them clarity that this isn’t a casual chat. It’s not a debate. It’s feedback and it’s their duty to hear it. If you don’t make this clear, conversations can get very slippery and very frustrating.

Get Ready for the Clap Back

What often happens next, especially when giving feedback to engineers, is they need to rationalise about it. In the worst case, they feel the need to argue about it.

It’s important to distinguish between two cases here. One case is where you gave poorly-thought-out feedback and the person you’re giving feedback to is reasonably disputing it. This happened to me more when I was new to mentorship and I couldn’t quite see clearly how to help someone. The other case is the more common one — you’re giving feedback that the other person doesn’t want to hear and they’re trying to squirm around it.

This happens all the time. We’re human. We have emotions. We feel shame. Frustration. Embarrassment. For most people, the first port of call when these emotions come bubbling up is to find a way to not feel those feelings. Engineers are exceptional at this. We explain complex chains of events to ourselves. We reason and rationalise how the feedback doesn’t precisely match the circumstances. My intern from way-back-when was a master of this. He was exceptional at arguing about or excusing his own behaviours. At dodging accountability.

A younger me would engage is this fight. I would try to engage with those flawed logical arguments and try to outwit my opponent at his or her own game. I don’t do that any more. What I’ve learned over the years is to just wait a few minutes.

It’s amazing. You give someone tough feedback. They squirm. They rationalise. They explain to you what you already know. They talk themselves into it. Out of it. Around it. And if you just wait a few minutes, give them time to process all of those feelings, they usually come around. I can’t tell you how many conversations I’ve been in where a junior engineer started by arguing back against my feedback and then ended with them explaining how they’re going to use the feedback to change their behaviour to improve. In each of these conversations, the dominant voice was theirs, not mine. I didn’t wrestle with them. I just gave them time to digest the feedback outloud.

We’re complicated creatures, humans. Our brains can lead us to say things based on one neuro-chemical disposition that we then immediately don’t agree with because we just changed our mind — even though what we said was the opposite of what we now feel. As a mentor, if I latch onto the first thing that comes out of someone’s mouth when I give them tough feedback, I’ll ruin the moment. Again, parents already know this. You can watch a parent of a 3 or 4 year old tell the child for the fifth time, “Please do not to stand on the sofa. You might fall off.” The child will often — in the middle of telling the parent that “I’m not going to fall” and “I don’t need to get down” — get down. The words follow the old pattern, but the actions reflect the new one.

The moral of the story is that when you give the feedback, consider the subsequent few minutes to be messy and confused. Give the person time to process and rewire their own behaviour, even if mid-way-through, they say the opposite of what you’d hope to hear. They might surprise you with what they do.


Learning to give feedback was tough. Painful, in fact. Failing at it cost me a performance review, the respect of my peers and betters, and a lot of shame within myself. Most of all, it led me to treat an intern — someone who trusted me — in a really brutal way. What I was really missing was some basic internal compassion and a sense of how to help someone who didn’t know how to help themselves. Now, as someone who bounces between tech leadership and management, I see just how invaluable this skill is. And I see the foundational elements that are required to do it. If you’re not balanced emotionally, you can’t effectively lead a team. If you’re not able to have your feedback spit back at you without losing your cool, you’re not going to get the best out of your teammates. If you can see things from their point of view and give them direct feedback from a balanced position, you’ll run more effective teams and more successful projects. I know, because I’m living that reality day to day now.

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