Diary of a new engineering team lead: How are you really?

I have the goal of writing one of these posts every month. I published the first at the very start of April and if I manage to get this written up and posted in time I might just squeak it in by May’s end. Technically meeting my goal, right?

I have considered myself to be shy and/or introverted for most of my life, but in my mid-twenties (thanks in part to forcing myself to take an improv course) I discovered I am actually quite a personable introvert. If I relax it turns out I can actually speak to people, though my eighteen-year-old self would find that idea quite far-fetched. I think it’s this ability to have good conversations with people (and make terrible jokes) without being overbearingly extroverted that makes people think I should try leading. In a field full of introverts a slightly more extroverted introvert is perhaps well suited to helping others feel comfortable opening up.

The idea of today’s post is a simple one that came to me while talking to someone else who’s thinking of becoming a team lead. I had only been in the job a couple of weeks and felt like a complete novice, but I wanted to try to give some advice. Much like with these posts, I think that forcing myself to produce some wisdom from all this puts me in more of an overt learning mindset than I might otherwise be in.

Many experts on engineering leadership say that good 1-1s are the backbone of success in any leadership role. I feel this is intuitively correct—the relationships and rapport that you build through deep one-on-one conversations make every other aspect of working with people far easier, more fulfilling and more fun.

My friend was struggling to get his team members to tell him how they were actually feeling in 1-1s. I hadn’t really felt this pain—generally my 1-1s end up being quite illuminating and don’t feel like a huge struggle. I had to think a little to understand why that might be.

I don’t think this is the whole story, but the tip I came out with this particular day was this:

In 1-1s, ask how someone is, and listen to their answer. Then ask them again, a slightly different way. The second time, they’ll probably tell you how they really feel.

What am I talking about? Wouldn’t that be annoying?

Honestly, I think I’m at an advantage with this one just because I’m Irish, and “How are ya?” is a standard greeting and only as much of an actual inquiry as someone saying “Hello,” generally speaking. You’d often say it as you walk past an acquaintance, without even breaking stride. Even with close friends, it’s often the ritual that starts most chats. As a result, I’m used to plenty of conversations going something like:

Hey, how are ya?

Grand! You?

Can’t complain, any news?

I thought this was uniquely Irish, but in my 1-1s I found the opening often going a similar way. People answer with something super short, then ask how you are in return. That’s great, and understandable. Where my non-Irish colleagues differ, however, is that when I reflexively ask them the second time, with different wording, they usually pause, reflect, and then answer with more depth and honesty. Worries and fears get talked about, or frustrations.

My theory is that the first time elicits an automatic response. People politely answer without any real thought, and return the question—the standard rhythm of conversational back and forth. The second time is enough to jog a brain into actually considering the question, and with politeness out of the way they get to tell me how they really feel.

I must also commend my teammates for how honest and candid they are with their feedback. People aren’t holding back, or at least not enough that I notice. Our first couple of months together have had some difficulties (projects not moving the way we’d like—I have a post in the works about this). It’s been wonderful to get honest check-ins with how people feel about the situation. This is, after all, the core of a good 1-1.

My colleague reported back a week later that the tip had made a considerable impact on the quality of his 1-1s. Now that I’m doing it consciously, I see it too.

Perhaps publicising it this way will ruin the ‘trick’, but I think it’s such a natural, human thing that it’s unlikely to stop working. We all, fundamentally, want to connect with other people—to know how they are and to tell them how we feel. Being asked how you are is almost like the word ‘said’ after dialogue in books, carrying meaning but not catching attention. Your brain understands what it means, but it doesn’t trip over it.

The true key behind this, of course, is that you actually have to care how someone is for this to work. You can use almost any wording as long as you genuinely care about the answer, and listen carefully to what they say and how they say it. This little tip just greases the wheel.

I’m giving you permission not to feel awkward about effectively asking the same question twice. Nobody will even notice, but the results could be profound.