Leadership lessons I learnt from Will Larson
10 timeless leadership lessons from Will Larson that shaped my journey through every step of engineering management.
👋 Hey, it’s Stephane. Welcome to my weekly newsletter where I share lessons, and stories from my journey to help you lead with confidence as an Engineering Manager.
Will Larson is the author of amazing books like An Elegant Puzzle and Staff Engineer and his blog is also very active and top-notch. I recommend his material to all Engineering Leaders.
Last year he published The Engineering Executive’s Primer which I somehow missed, so when I noticed it recently, I had to get it delivered ASAP.
The truth is, that this book is for experienced leaders and not so much aspiring or new EMs which I know you might be.
So after reading it, I thought what a great tribute to him it would be if I collected all the wisdom I have got from him throughout the years and shared it with you:
For engineers working towards becoming a manager
For first-time managers
For managers working towards exec roles
Let’s get into it.
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Back to this week’s thought.
For aspiring Engineering Managers
You know this hopefully well that this path isn’t for everyone.
1. Know Why you want to become a manager
Reflect deeply on your motivation for moving into management. As an aspiring engineering manager, having a clear “why” will guide your career decisions and prepare you to answer tough questions about your goals.
This self-awareness ensures you’re pursuing leadership for the right reasons (e.g. desire to amplify impact or grow teams), not just title or status.
What is your why? Define it well.
Write it on a piece of paper. Does it inspire you when you read it?
Leave it and read it again after a week.. Does it spark the same emotions of fire?
Does it still make sense to you? If so, that means you’re onto something!
Management will test your patience, stretch your people skills, and force you into problems with no clear answer. If you’re not in it for the right reasons, it’ll eat you alive.
2. Recognize each role is “One of One”
There is no single template for engineering leadership success.
There are frameworks that seem to be successful in different environments, but every engineering manager or executive role is unique with its own context and set of challenges.
For an aspiring manager, this means you should be learning from others’ experiences but being ready to adapt.
What worked for someone else might not work for you. Embrace a flexible mindset and focus on principles rather than a one-size-fits-all playbook.
It’ll take some time of experimentation and growth for you to find your style and get somewhat comfortable in a management role.
3. Look beyond internal promotions
Don’t rely solely on climbing the ladder in your current company. Internal engineering leadership openings can be rare and often very competitive.
Instead, proactively expand your professional network and keep an eye on external opportunities.
This is exactly how I got my first Engineering Manager offer back in 2019. I was working as a Senior Software Engineer at a different company when I managed to get in the interview pipeline for an external EM role.
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Many high-level positions aren’t even posted publicly, they’re filled via personal connections. By networking and engaging with the industry, you increase your chances of finding a management role and set yourself up with allies and mentors before you even get the title.
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For New Engineering Managers
You got the job. It might have felt hard to get but the truth is that the hard part begins now.
Your team’s watching. Your manager expects big things from you. You don’t know if you’re sinking or swimming.
4. Prioritize learning and trust in your first 90 days
In the first few months of managing, resist the urge to “fix everything” immediately.
Focus on understanding your organization’s people, processes, and pain points, and on building trust with your team and peers.
A few months ago, I joined a new company. My plan for the first 30-60 days was to try not to make any decision. Just observe and learn how things work and why. At Amazon, new executives are not allowed to contribute at all for the first 3 months, just learn.
Spend time learning how the business works, what the culture values, and where the engineering team stands (technical health, morale, delivery) before making changes.
By listening and observing first, you’ll avoid missteps and gain credibility.
Remember not to judge or impose past solutions without context, as every team’s situation is different.
5. Communicate consistently and run effective meetings
Once you understand a bit more about the organisation it’ll be your turn to start communicating.
Good communication is a core part of team management.
New managers should establish regular info-sharing habits and meeting routines to keep everyone aligned.
For example, hold recurring one-on-ones and team meetings to spread context and surface concerns.
It’s also wise to send a brief weekly update (sometimes called a “weekly drip”) so the team knows what’s happening and what you’re focused on.
These practices create transparency, reinforce team culture, and ensure problems or updates don’t get lost in silence.
6. Manage your energy and priorities
Management is demanding, sometimes thankless and lonely, so be deliberate about how you spend your time.
You should be putting the company and team needs first, but don’t neglect the work that keeps you energized. If you’re burning out or constantly drained, allocate some time to projects that excite you or play to your strengths – and delegate or adjust tasks when possible.
Ffind a sustainable balance: handle the urgent priorities, but if the balance between team responsibilities and your own energy is off in the long run, proactively address it so you can lead effectively without burning out.
For Engineering Managers moving toward Exec roles
First of all congrats! This is another big move in your career.
Personally I view this one as big of a step as going from Senior to Staff Engineer. Exec roles require a whole new skillset to be successfull compared to managing a team or two as an EM.
7. Develop a clear engineering strategy
As you prepare for higher-level leadership, focus on strategic planning.
Craft an engineering strategy document that outlines where and why your organization will allocate its people and budget, the fundamental guiding rules for your teams, and how decisions should be made in engineering.
This strategic framework aligns the engineering org with the business’s goals.
For instance, Will Larson highlights that a good strategy includes a solid diagnosis of core challenges, a set of guiding policies (principles/trade-offs) for the organization, and coherent actions to execute on those policies.
Being able to define and communicate such a strategy will demonstrate that you can steer the engineering ship at the executive level.
Tip: you can experiment with this at all levels. If you’re an EM or IC you could draft such a document for your team with your manager. Trust me, you will learn a ton just from doing that and I can almost guarantee it’ll help you progress your career.
8. Work in “Company-First” Partnership with Executives
Transitioning to an executive role means collaborating closely with CEO, product heads, and other peer leaders.
To succeed, adopt a company-first perspective and strong listening habits when dealing with fellow executives.
In practice, this means aligning engineering initiatives with broader business objectives and being receptive to input from non-engineering stakeholders.
It also means not simply copying tactics from your previous experiences, first understand your current company’s landscape and why things are done a certain way.
By considering a variety of perspectives and focusing on what’s best for the whole company (not just engineering), you’ll build trust among the executive team and ensure engineering is seen as a reliable partner in shaping strategy.
9. Build a cohesive Engineering Leadership team
At the executive level, your success depends on the leaders under you.
Treat your engineering managers/directors as your “first team” and invest in their unity and growth.
Set clear team values and operating principles for how your leadership team works together (e.g. how you make decisions, share information, and uphold quality).
It’s equally important to explicitly communicate expectations to your managers. For example, that they should lead their teams effectively, collaborate with their peers, stay aligned on strategy, and proactively inform you of issues.
By cultivating an aligned, trust-filled leadership team, you ensure that the entire engineering organization runs smoothly even as it scales (and you’ll free yourself to focus on higher-level strategy, knowing your managers are going in the same direction).
10. Use metrics wisely to drive results
A key executive skill is measuring and communicating engineering’s impact.
As you step up, determine which metrics matter for your org’s success - such as delivery throughput, system reliability, quality measures, or team engagement - and track them to inform decisions and report progress to stakeholders (e.g. the CEO or board).
However, be careful with metrics: they can be misused them or create wrong incentives.
For instance, don’t fixate on individual productivity metrics or vanity numbers that don’t drive real outcomes.
And if there’s a trust issue in the organization, address that first rather than masking it with numbers.
The lesson is to use data as a tool for insight and alignment, not as a hammer. When done right, a balanced set of metrics (covering execution, operational health, and improvement over time) can be a powerful framework for strategic thinking and ensuring engineering is delivering value in terms executives understand and care about.
Not affiliated, Engineering Enablement substack has great resources on this topic (written by the founders of DX - a really awesome platform for getting developer insight).
Final word from me
If you’re serious about growing in this field - as a lead, a manager, or an exec - I am of the opinion that his recent book that inspired me to write this issue is of value.
It might not be super practical to you today, but it’ll help you get a sense of how progression looks like for managers, which I think makes it worth it.
That’s all, folks!
See you in the next one,
~ Stephane
PS. If you’re taking this management thing seriously, here are more ways I can help:
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I've learnt engineering management is a constant process of finding clarity within uncertain information.
That's for sharing your learnings for all levels of engineering leaders!
I really like Will Larson approach to building engineering strategies. Great lessons!