Learning From Great Leaders Around You

I'm early in my career. When choosing jobs, I've chosen to prioritise learning above everything else. That's not to say that I haven't pursued a good salary and interesting work, but rather that they come secondary to the learning that comes with a role.

Early on in my previous job I was part of a team working on a new project. It was led by our CTO and received a lot of attention from the rest of the leadership team. A couple of times each week I'd sit in on meetings with them. For the most part, I was just a fly on the wall, observing the conversations and interactions.

I learnt a ridiculous amount by being in the room when they were thinking through and making decisions. It made me realise that you can accelerate your learning and your career significantly by getting in the room with great leaders and thinkers. Here's why:

1. You begin to notice patterns in the things leaders place importance on. Often, a point would seem clear to me, but they'd dig in deeper, double click on an idea, ask a few more questions. More often than not, I'd realise that I'd overlooked something important. The best thinkers all seemed to have an intuition for important ideas and an eagerness to understand them very deeply.
2. You're given the chance to watch them interact and communicate. How do they challenge each other? What kind of questions do they ask? How do they approach different people to try and facilitate effective conversations? I realised that your opinion is only as valuable as your ability to communicate it.
3. Strong opinions, lightly held. One of the best things you can do for your career is learn how to develop a strong point of view, while being willing to change your mind when presented with better information. The way someone handles themselves when confronted with opposing opinions tells you a lot about them.
4. The best way to describe these meetings is a battle ground of ideas. These were very accomplished and astute thinkers presenting ideas to battle against each other in a quest for truth. Being in that environment is exhilarating. It's humbling, too. If I want to sit in those seats one day, there are a lot of lessons I need to learn. Seeing the rigour used by these leaders when making decisions forced me to do the same. There was no way I was going to present an idea without having thought it through properly, without understanding the implications and edge cases, without being able to defend it. It raised the bar and forced me to try and rise to it.
5. Perhaps most importantly, it facilitates future work. Great leaders are right, a lot. They know things. So having their operating philosophy available on-demand, or even a rough approximation of it, can be really useful in moving the ball forward and getting teams aligned around the best possible decision.

I started a new job a few months ago, moving from a company of ~150 people to a company of ~15 people. Since changing roles and joining a smaller team, I've found myself in these situations more frequently. I've been on the line more often and found myself being the target of questions about what we're doing and how we're going about it. Real learning comes from working on things that are critical to the company because it means that you're going to get feedback and criticism on the work you're doing.

I see this as an under appreciated benefit of working on a smaller team. Big organisations come with more hiding spots. It's easier to avoid responsibility. It's often more comfortable, but you need direct involvement if you want to get good. You need to make mistakes, fix them and continue moving forward.

I've been lucky to find myself in these environments. Not every position is like that. You don't always have the opportunity to get in the room with decision-makers on a consistent basis.

I haven't identified reliable ways to ensure that you do besides displaying a lot of agency. Identify meetings that you don’t normally attend, and ask if you can sit in and observe them. For example: If you’re in product, sit in on the engineering team’s daily stand-up. Ask your boss if you can shadow them some time at a meeting you don’t normally go to. Observe sales and customer support calls. When you ask to sit in, explain why you want to observe. Practice paying attention to more than just the content of the meeting. Notice how your peers and other leaders speak, think and act. You'll learn a lot as a result.