From getting shit done to leading people.

As part of my career development homework, I was asked to identify four areas where I’d like to focus my efforts over the coming few months.

Of course, there are plenty of areas where I’d like to improve, but I wanted to find four complementary areas that could work together rather than four completely separate goals.

The reasoning behind my choices is pretty simple. Up until this point in my career, I’ve largely had to focus on myself and what I needed to do to achieve success. If I’m going to grow into a leadership position, though, I think there are some core areas where I need to develop. These are the four I’ve landed on.

Courageous Communication

I’m certainly opinionated, but I’m not naturally someone who tries to rock the boat. I’m unlikely to disagree with a superior, and when I do, it’s usually delivered on eggshells.

I don’t necessarily think that’s because I’m agreeable by nature. I think it’s more because I’ve been so focused on securing the bag, so to speak.

When you start with nothing and you’re given a life-changing opportunity, there’s a lot to gain, and I’ve never wanted to jeopardise that. Through that lens, I could convince myself that it’s been strategic to some degree. But I think it’s also trained some of the battle-hardiness out of my persuasive communication.

I’m also quite open to the possibility that I’m wrong, which I think is generally a good quality. The downside is that it probably makes me easier to move from my position when someone else feels strongly about something.

What I need to get better at is having a firmer opinion, stress-testing it, and then being able to deliver it with conviction.

Leadership Presence

For me, this is where there’s probably the biggest overlap with courageous communication.

In my day-to-day work, I see confident and courageous communication as one of the biggest building blocks of leadership presence. That’s actually one of the reasons I wanted to include this on the list, even though it overlaps with the first area.

Of course, leaders need other qualities too. Firm decision-making comes to mind. So does big-picture thinking and accountability.

One of the qualities I personally admire most in a leader is the willingness to get their hands dirty when the situation requires it, and the ability to operate at a high standard alongside the people they’re leading.

That might not always be necessary, but it’s something I look for because I want to feel like I have something to learn from the people above me beyond sweet-talking and political navigation.

If I’m going to lead people effectively, I want to be someone who can do the work, understand the work, and then give other people the confidence to follow me.

Relationship Building

I’d consider myself a pretty friendly and chatty person, especially in person. But because of the nature of remote work, and because I’ve convinced myself there’s near-zero chance of establishing a genuinely close friendship through Zoom calls, I’ve largely neglected this side of my career.

The last true friends I made at work were people I worked with in person at Apple.

I’m not sure whether it’s the shared struggle, the ability to make small talk, or maybe just the ability to shit-talk over lunch that brings people together beyond a professional capacity. But I do know that if I left my current job tomorrow, there’s probably no one I’d stay in touch with in any great capacity.

Maybe friendship isn’t necessarily the goal of relationship building at work. But when I think about the people I could rely on in a crunch, the people who might put me forward for a role, or the people who might put in a good word for me with a senior person they work alongside, it tends to be the people I’ve built genuinely strong personal relationships with.

I also think there’s something particularly valuable in building relationships with senior people who can sometimes have an aura of unapproachability around them.

When you actually talk to them, they’re usually perfectly friendly. But there’s still a barrier there, and I think part of career development is learning how to break through that barrier and become someone who is considered part of the inner circle.

Prioritisation and Alignment

I don’t have much of an issue identifying my own priorities, and I’ve always been pretty good at doing whatever is needed to move the team forward.

Where I think I could be stronger is in organising and aligning other people.

I have an almost allergic reaction to project tracking and busywork in general. Unfortunately, it’s somewhat of a necessary evil in the product world.

I’ve been fortunate throughout my career to work with producers and project managers who live in spreadsheets so that I don’t have to. But as I move towards leadership, I can’t rely on someone else to always take care of that side of things.

This is probably one area where I’ll look to AI to streamline as much of the administrative work as possible.

The alignment piece is more interesting to me, though, because it comes back to communication and selling a vision that people actually buy into.

It’s also about identifying the right people for a given task and making sure that people’s responsibilities play to their individual strengths. Ideally, everyone should get something out of the work: the team gets the outcome it needs, and each person gets an opportunity to do something they’re particularly good at or interested in.

Ultimately, I think these four areas are pretty interconnected.

Courageous communication should help build leadership presence. Leadership presence should make relationship building easier. And stronger relationships, combined with better prioritisation and alignment, should make it easier to actually lead a team rather than simply being the person who gets the work done.

That feels like the bigger shift I need to make over the next few months: moving from being successful because of what I can personally accomplish to being successful because of what I can enable other people to accomplish.

In addition to going through the career coaching, I also picked up a copy of Empowered by Marty Cagan and Chris Jones. It has a 4.6 rating on Amazon and is considered a must-read for people looking to lead product teams. I'm curious to see if there's much to learn, given it's been my day-to-day life for close to 10 years now, but hopefully there will be some interesting tips that I will share in a future edition of the blog.