On preparing for your first leadership role
A checklist I wish I had back in the day
When I first became Head of Product, I was too excited about the prospect of being the Head of Product vs really knowing what I was getting myself into.
I was excited for many reasons:
It’s career progression. It felt like the most natural step for me after having been Senior PM/Product Lead (without direct reports, though) for so long, according to any org chart that I’ve seen for most of my career.
The prospect of finally being able to make decisions and having bigger influence/impact in the organization! I thought I could finally get my way!
Mentoring the PMs more junior than I was. It was so cool to think that I was responsible for shaping the new generation of Product Managers.
When I finally got it, it was less glamorous than the picture I’ve painted in my head. For so many reasons, too:
There was always somebody who was unhappy with something for one reason or another. And they all expected me to do something about it. Whether it was somebody from my team or their stakeholders, my own peers, my manager or their stakeholders, my manager’s manager or their stakeholders. The concerns I’ve had to deal with suddenly came from all levels.
The immense amount of context I had to pay attention to felt overwhelming. Not only did I have to be aware of the business context of the entire company, now I had to connect the dots between that and my entire part of the organization’s product and their impact (vs before when I was mostly aware of my product’s impact).
The changes in the organization were no longer just for me and my immediate team to deal with, I had to help my side of the organization deal with it too — which includes both logistical/practical AND emotional help.
And while I WAS able to make more decisions as a leader, the amount of alignment that those decisions needed was 100x bigger than they used to be. And when some decisions came with very little information/context/precedent, the fear of making wrong decisions was gripping. The accountability + logistics of decisions became so much bigger.
The amount of meetings I felt like I needed to be part blew up a million fold. The amount of 1:1s I had to do was insane. I was helping my team grow in their career ON TOP of helping them create significant business impact. Then there were the 1:1s with my peers because there was always internal situations for us to deal with together. Then there were the meetings with stakeholders, the leadership group, the rituals for my side of the organization to create a sense of team (not to mention alignment and synergies). Man. I was in meetings for the most part of the day, I felt like I needed to work extra hours just to get my own shit done.
Don’t get me wrong, I had so much fun. And I was grateful I’ve had really great senior leaders around me (on top of my direct manager) who helped me navigate my change. The salary increase was also sweet, not going to lie. And my reputation in the industry exploded (in a good way!).
But the stress was making me extremely short-tempered, extremely tired all the time, and have zero appetite for other things in my life.
Every piece of feedback I received felt like an attack on my person, whether it was about me and my leadership or how the meeting rooms were always full.
I don’t regret becoming the Head of Product. Quite the opposite. I’m glad I got it. It helped me grow in so many ways which was what I was looking for in the first place.
But there ARE things I wish I knew when I started. As much as there WERE things that I was already good at that helped me feel less like a headless chicken.
So if you’re preparing for your first leadership role now, let me share a few things that have helped me navigate the role and what’s helping my coaching clients become more effective leaders themselves + enjoy the ride.
Things to help you prepare for your first leadership role
Know the business you are in inside and out. Truly understand how your company makes money. As in:
How the company’s current goals and strategies are intended to help the company grow.
How the company could be losing money and why.
Who are the competitors, where is the indutry going, what are the opportunities and risks, even regulations that could have an impact on what you’re doing, etc. Not at just the company level now but at an industry level.
Familiarize yourself with the different products that are being built in your company and how they’re contributing to the company making money.
Know how they’re contributing to the company’s goals one way or another.
Familiarize yourself with their strategy/roadmap if they have a separate one. You don’t have to memorize it but know what’s important for them and why.
Familiarize yourself with the different teams that are building things in your company. And start building a relationship with them, if you haven’t yet.
Get to know them. Understand what makes their team good, how they work, how they solve problems, as well as what makes them tick.
Every team usually has an “unofficial” influencer. The person that everybody trusts the most. Get to know who those people are and understand why they’re the person most people look up to.
Get to know people’s strengths and opportunities. What are people good at? What are their areas for growth? What are their goals?
Speak up more.
Start speaking with people you’re not used to speaking with. That may include future peers, future stakeholders, and especially people way above your paygrade. Start building relationships with these people. The sooner you do, the sooner you build trust.
Get used to sharing your opinions. But also get used to sharing them with perspective and language that’s expected from the level you’re intending to be in. If that’s leadership, it’s gotta be strategic, coming from a company/business perspective — and not just from your product’s pov.
Get used to speaking in front a room full of people who will ask you questions, give you feedback in public, and you might not have the answer on the top of your head. Get comfortable with that situation.
Get out of the building. Literally. Get input that’s beyond your company walls. There are a lot of things to learn from.
Build relationships with people outside of your company. They might be in the same industry, doing the role you’re aspiring to have, etc. They don’t necessarily have to be product people. They can be founders/entrepreneurs, experts in the field, investors, etc.
Go beyond your industry, your country, your continent? How are products being built and sold for other markets?
Build a great relationship with your new best friend, uncertainty. There are many ways to do this, but uncertainty will be pretty much part of your day dressed in different clothes. Reorgs, hiring, promotions/salary calibrations, a new 5-year strategy at the start of every fiscal year. The sooner you learn to keep calm throughout these things and stop holding your breath for potential fall out, the sooner you can look forward to the amazing opportunities that are waiting for you on the other side. Bonus, you can help your team, your peers, walk through uncertainty with their backs straight and their chins held high alongside you.
Spend time thinking about what kind of leader you want to be. Go beyond thinking “being strategic” or “having impact”. Be more specific.
What kind of feedback do you want to be receiving?
If you’re already the ideal leader you already are: How would you be dealing with unfavourable circumstances? What would you be celebrating with your team?
What’s your personal definition of success?
If you’ll notice, I didn’t include in this list anything around upskilling on strategy, communication, or other similar skills that are asked for in leadership.
That’s on purpose.
They’re critical skills, obviously. But those skills are only as good as your input is and what you’ve normalized for yourself.
And the list above is about expanding your sources of input so you can expand your way of thinking. As well as reducing areas of unknown so your focus is on what’s at stake, so you don’t have to be learning so many things at the same time.
Is this a foolproof or even exhaustive plan? Not at all. But it’s a plan that gives you space for when you’re onboarding to the role.
Think of it this way:
By the time you’re having your 1:1s with your direct reports, you already know a lot about them, maybe including their goals, so you can focus on learning how to be a manager vs also learning about the people you’re managing.
By the time you need to figure out how to get multiple teams to collaborate with each other, you already know what people are building, how their teams work, and maybe even have a great relationship with their manager so you don’t have to spend a lot of time building trust AT THE SAME TIME as gaining alignment on something complex.
By the time you have to create a strategy that wins, you already have multiple sources of information, varied perspectives of the market, etc.
The output is only as good as the input is. And scrambling to get good at producing a good output that can pave the way of a good outcome, while you’re reaching for as much input as possible can burn you out faster than the next reorg.
And if you’re positioning yourself for consideration to be a leader? Having all of these input at hand, exposing yourself to different environments and perspectives, and more — the way you communicate and with whom will naturally change, the trust you build with other people will naturally expand your influence inside and outside of your organization, the way you think about the business and the opportunities it can explore will naturally expand.
You start embodying the leader you want to be, and other people can see you for it. Thereby increasing your chances considerably of getting into the role sooner rather than later.
And once you have it, it gives you space to enjoy your new role more vs constantly second-guessing if you’re doing it right.
I help new and aspiring leaders in Product, Engineering, Design, and other functional experts working in Tech not only become effective leaders but also be the leaders they aspire to be, minus the existential crisis and risk of burnout.
I have open 1:1 coaching spots right now. So if you’re preparing for your first leadership role or already are in it, I’d love to be your partner in making this journey more fun for you. So let’s chat.
Kax
p.s.
My newsletter will always be free. But if you find my posts helpful to you and your career goals, you might consider leaving me a tip/buying me a coffee :)