Growing from senior to lead
For many designers and software engineers in the tech industry, career progression almost always involves the idea of switching lanes to some sort of a management ’track’. The thought of doing less technical work puts off many people who have dedicated their lives to craftsmanship and delivering high-quality work. In this article, I’ll share my opinion on what I think the core ingredients for being a lead are, and shed some light on what the work of a leader entails. This piece was first drafted in October 2025, and took roughly a year to finish as it comes straight from my heart.
Needless to say, a lead is already a senior as a baseline. While I’ve split them into 2 separate articles, many ideas discussed in the last one1 apply in both places and overlap quite a bit. One good way to begin thinking about becoming a lead is imagining yourself in a group of peers, all of whom are equally capable and experienced. How do you pick someone from within to lead the entire group?
What defines a leader boils down to the ability to choose your team’s focus. You’ve probably heard of this phrase a lot:
Doing the right things, the right way.
Being a leader is all about choosing what those right things are, and committing to them. The bigger your team, the harder it is.
Point of view
The act of choosing implies having an opinion or perspective of something that particularly lies in the future. Specifically, work that has yet to be defined. What should your team be working on for the next 3, 6 or 12 months? More importantly, what is it that you truly believe in and want to focus your team on, regardless of what anyone says, or even if anyone says anything at all?
As a leader, you cannot simply allow other people to dictate your team’s entire portfolio where your areas of expertise and skillsets are concerned. It is not uncommon to see strong seniors struggle with this because they have gotten used to helping others, working horizontally, collaborating and being rewarded for it. They got to where they are because of their craft, and have succeeded in delivering value to the rest of the org with their skills. Their next year’s plan is either dominated by a backlog of requests from other people, or a list of todo completely derived from OKRs trickled down from the top. Year in, year out.
Absorbing leadership’s plan and requests is not the problem here. There are times when it makes sense to do that when all hands are on deck, and the entire business needs to pivot. I get it, but that’s not what I’m talking about. You can be aligned with direction from the top and have your own point of view at the same time. What you need to be careful of is mistaking someone else’s opinion for your own.
You are the expert here—you should be driving the conversation around what your domain could bring value to the business.
On borrowed conviction
When leaders take the stage and address their teams, they’re speaking from a position of authority. As a listener, you don’t have certain information that they might be privy to, and it’s easy to just accept whatever they say. We also know that they are smart; that’s why they’re there. All these things add up to lend the impression that they have perfect information and are in the best position to make decisions. And so, when your boss asks you to jump, you instinctively ask “how high?”.
Your boss strongly believes that your team should do X and Y in the next year, and you nod furiously in agreement. Everyone has the best intentions here, there’s no malice involved, the arguments sound correct, and the goals look aligned all the way up to your CEO’s hair strands. You relay the OKRs for the coming year to your team enthusiastically, and this is exactly the point where you failed your boss, yourself, and your team. You’ve become a carrier pigeon, or a ‘meat proxy’ in today’s internet lingo.
It is one thing to work on things just because “management asked for it”, and another to do them because you’re already going to do them anyway, and management just happened to be aligned with it. This is a simple (but hard) problem to solve. Do your homework beforehand and envision the future before anyone tells you what it could look like.
And to know what it looks like, you need to study and do a lot of homework. A shit ton.
Know a lot of things… and people
You need to know the business well, how it’s doing, where its competitors are, what customers need and where it hurts. You also need to know where the company is going, where it wants to go next, which then trickles down to where your department is going, what other departments are trying to achieve, what other teams in your own department are thinking about, where the workflow and process gaps are… basically every single external force that can impact or influence your team’s trajectory.
So first, master the skill of gaining access to information, and not just that, but also how to maintain continued access. Build trust, reputation, connections and relationships, raise social capital and your standing, exercise those “soft skills” that are often neglected by technical folks so that you can maximise the number of inputs into your plans and your chances of success.
Make plenty of keikaku
But knowing is not enough. Knowing things does not equate to having an opinion, it is merely the prerequisite. Synthesise the information you have, and make many plans. Then make plans for those plans. You don’t have to reveal everything at once, but you want them in your back pocket because things can change on a dime and the next thing you know, both your boss and team members are looking to you for direction. Yes, commit to the finish line, but stay flexible on the route.
While you may only be focused on one thing (or two to three at most), be prepared for multiple ways to achieve the same thing through different means. In fact, don’t count out partial achievements; some things might take a bit longer and it’s not wise to reject a plan just because you can’t achieve it in the ideal sequence you have in your head. Also, don’t just execute one plan at one time; be multithreaded and let multiple approaches play out at their own speeds. Prune the dead ends, and redirect your focus onto the most promising plans.
Reading between the lines
Side note here. We all know that actions speak louder than words. If you full commit to a direction which heavily depends on another team or leader, your future is kinda held hostage by them.
Sometimes, you’ve got to read between the lines, interpret situations accurately and hear what is not said. Do collaborators or sponsors actually have skin in your game? Did they commit resources and budget, or did they waffle, deflect and postpone? If you don’t master this skill, you will—emphatically in Singlish—die also don’t know how you died.
Exhausted yet? We’re only halfway done.
It’s still all about people
Fundamentally, you’re not just making a decision for yourself, you’re also making it for other people. You’re making decisions on behalf of your very own teammates, collaborators who rely on your work, and other leaders who rely on you being on top of your game. This already makes it a high-stakes decision, because one wrong turn and you’re burning precious resources twice—once for doing something with poor returns, and once more for steering the team back to the right thing.
As if it wasn’t hard enough to convince smart people to follow your lead, you also have to be careful of borrowed conviction flowing downwards. Just as you nod your head in agreement with your boss, your team will do the same to you. How do you tell buy-in from deference? Different strokes for different folks. Some people push back as a way to test your idea, while others propose alternatives as a way to softly disagree. What you don’t want is for people to wait for instructions and fully agree in meetings. It’s usually a warning sign if there are no questions raised.
Delegation
After putting in all the legwork to have a point of view and communicating that vision, you don’t end up doing the work yourself. You physically can’t because there’s too much. Sorry, it doesn’t get better here for ‘craftspeople’. We’ve only touched on the first part which is doing the right things. Doing them the right way as a leader means letting go and creating the system and environment for others to do so.
I’ve reflected on this same thing in an article I wrote ~6 years ago2, and it still holds true today. Design yourself out of the way. One measure of your success in delegation is that the work gets completed without you being in the room. I’m not about to expand into how you can do this, as it would double the length of this article. Smarter people have spilt plenty of ink on this topic already in best-selling self-help and leadership books. LLMs can also give you a concise 5-step plan to doing this, but I will just touch on one particular thing I find most important.
No one is checking in on you
Taking the lead means you’re accountable for everything, and it’s a lot like running your own business. Once you’ve set your own OKRs and your boss has agreed, the deadlines and commitments are yours to promise. No one is outlining the work to be done for you, chopping it up into release plans and giving you a schedule.
The best thing you can do for yourself is installing feedback loops that help you find out if you’re wrong quickly. State your bet upfront clearly so you know what wrong looks like. Setup cadences and systems of accountability with your peers or your one downs. Hopefully, you have been nurturing their growth so that they’re actually capable of supporting you in this sort of ambiguous work.
In the event that you do hit a dead end, you’ll realise it sooner than your boss. Always seek feedback early, and communicate changes early. Don’t wait till you can schedule a meeting; a short message or email to let your boss know what changed is incredibly valuable—they have their own timeline and ongoing conversations with other leaders. You don’t want them to make verbal commitments not knowing the latest developments that only you have visibility into.
Conclusion
We’ve talked a ton about what a leader should do, mostly cerebral and cognitive things, or the mind of a leader if you will. I’ll end off with the heart of the matter.
As a leader, you lead people. The day will come when you no longer lead them, and you’ll know if you did a good job when they decide to follow you even when they don’t have to.