Surprising things I learned about leadership

Unexpected discoveries from an individual contributor

TL;DR

• Leading is harder but also more rewarding than you think
• Meetings are a different form of productivity
• 1 on 1’s are a hidden gem of meetings
• Leadership has lots of work behind the scenes

Your greatness

Leading a team summons greatness out of you, greatness you might not know is there. It’s harder than you expect, and also more rewarding.

In the process, you’ll discover surprising things about yourself and others.

I know. Because that’s what happened to me.

Interim tech lead

I was invited to act as temporary tech liaison for my team while we looked to fill an open Director of Engineering position.

During those 60 days, I learned several surprising things that shifted my expectations about leadership.

You know what surprised me the most?

All the meetings

Before acting as a tech lead for my team, I spent 10% of my time in meetings, and 90% of my time programming. That ratio, or something similar, isn’t uncommon for an individual contributor.

Yet, during my first couple of weeks in the new leadership role, it changed to 40% meetings.

It wasn’t long before it felt like my productivity dropped to zero. I wasn’t coding nearly as much as I used to.

Thankfully my product manager anticipated this shift. She recommended I take on less work so I could adjust to my new responsibilities.

As my schedule filled up with meetings and more meetings, I asked my manager for time management advice.

Here are some best practices I picked up about how to get the most out of meetings.

Decide which meetings to attend

I mistakenly thought I had to attend every meeting on my calendar. Truth is, I didn’t.

Several invitations were sent more out of courtesy than necessity.

My manager offered some recommendations:

• “Learn the purpose of the meeting.”
• “Find out how important it is for you to be there.”
• “Ask if there’s anything the participants need from you at the meeting.”

Gathering that data helped me make better decisions about:

• How to prioritize my time
• If I would attend the meeting or not
• How to prepare my contribution to the meeting
• If I could benefit by observing, even if I didn’t contribute

Be more productive on meeting days

Between meetings I frequently experienced a weird productivity gap. With 15 minutes until the next meeting, I wasn’t motivated to start a project knowing that I’d need to stop right about the time I got into the flow.

My manager offered more time-saving advice:

“Plan ahead of time how to be as productive as possible during days with lots of meetings. Schedule all your meetings for one day, and remove the 15 minute gap between them.”

That was gold! Removing the 15 minute gap consolidated my non-meeting time into focused blocks where I could write code or plan. It significantly reduced interruption and context-switching.

Manage an onslaught of projects

Once I began attending all the meetings, I learned about a staggering number of projects I didn’t know about beforehand.

The first few planning meetings overwhelmed me. We discussed current projects, potential projects, backlog projects, upcoming projects, urgent projects, third party projects, and legacy projects.

I felt disheartened: we couldn’t do it all. We didn’t have enough engineers. The demands would swamp our department.

The only way I could avoid feeling overwhelmed was to change how I thought about projects. I needed a “big picture,” not detail-focused, way of thinking — a skill I didn’t usually exercise as an individual contributor.

More work will always be there. So, the key was to figure out which work was important or not.

Thomas Greaney, VP Product Management at Insider, explained it this way, “The biggest mistake we can make is to start working on the wrong stuff.”

That’s why Tech and Product Leads, stakeholders, and executive leaders put their brains together to create, prioritize, and decide on the projects our teams commit to each quarter. The more brainpower, the better.

As a leader, ask questions such as:

• “Will this project help get us where we want to go?”
• “How can we slice the projects into small pieces so we can iterate faster?”
• “Are there platform changes that will help us build features faster in the future?”

Meetings are a different form of productivity

As I attended more meetings, I realized my productivity paradigm began to change.

Meetings are a different form of productivity. Not good or bad, just different.

As an individual contributor, I felt more productive writing code than attending meetings. But as a leader, I felt most productive when I saw my team engaging during meetings. It’s not only where I gained insight into their needs, but where our discussions helped set the stage for our future productivity.

Some meetings are more effective than others. In the most effective meetings, I noticed how the organizer fostered ownership from attendees by asking open-ended questions that got us talking about:

• Things we cared about
• How we could make a better product
• Changes that could improve our workflow or workplace

I also learned how some recurring meetings built upon each other, with threads and timelines spanning months. I understood their value better after attending several times.

1 on 1's

Of all my meetings, 1 on 1’s were the most memorable. They’re kind of a hidden gem of meetings, where the most interesting and candid conversations happen.

It’s also where myself and my colleagues experienced the most leadership development. For example, when I brought my manager specific questions and concerns, he’d talk through helpful management principles, then tell me stories from his own similar experiences.

Similarly, when my team members mentioned goals or pain points, it provided us a valuable opportunity to plan how to serve them most effectively, and set them up to succeed.

I prepared for 1 on 1’s with my team members by reviewing our previous conversations, writing follow-up questions, and thinking about ways they could step into new responsibilities.

Behind the scenes

Every week I found myself devoting less time to writing code, and more time to preparing behind the scenes: thinking, planning, and meeting about about how to setup my team to succeed.

Picture someone preparing for hours, a meal that’ll be eaten in minutes.

My leadership experience was kind of like that.

There’s tons of work behind the scenes, preparing for interactions that seem brief by comparison.

When I prepared in advance, meetings were much more enjoyable and effective than when I rushed to prepare last minute.

Rewards

Once I started running a weekly meeting of my own, I made a surprising discovery: it felt rewarding to facilitate meetings where colleagues shared eagerness about upcoming projects, excitement about what they’re learning, funny stories, or inspiring experiences.

So I began to experiment with ways to have enriching experiences each time we met. We’d answer questions like these:

• What’s an insight you had this month?
• What decision are you most proud of this year?
• If you constrained yourself to one goal, what would it be?
• Tell us about the last time you gave or received great advice.
• Think about the platforms you work on. What things annoy you? What could we improve?

A new thought

During these meetings, a thought impressed itself upon me with greater force each time: “I’m surrounded by experts.” Experts in their field. Experts in life. Experts in growth.

I already knew my colleagues were smart. This was something different.

I saw my team members as masters of their craft who entrusted themselves to my care. I wanted to see them succeed personally. I wanted to see them grow.

I started to realize my role was about finding the best ways to serve them. To help them become greater. This realization, coaxed a form of leadership out of me I hadn’t recognized before.

This introduced a new problem, however. How could I grow as a leader in order to serve my team better?

So I turned to my leaders for help.

In my next blog post, I’ll share their advice, some stories, and more surprising things I learned about leadership. Stay tuned!

Thank you!

Thanks for learning about leadership with me. Hopefully you gained insight into some of the costs and benefits of leadership. And if you haven’t thought about it already, consider leading something!

And thanks to Reuben Ingber, Devon Darrow, Rachel Furst, and Mario Ruiz for your careful edits and improvements.

Got ideas or feedback?

I’d love to hear from you if you have questions or suggestions. Especially if there’s stuff you’d like to know more about, or if something I wrote about was confusing.

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