Less envelopes, more letters
How to spend your time on what matters.
Welcome to the July subscriber edition. Thank you, as always, for your support, and for being here.
In February this year, Jason Fried sat down with David Senra for a long conversation about business, craft, and what actually matters when you’re building something. Fried drew a distinction that I found very useful: envelope entrepreneurs versus letter entrepreneurs. Typically, builders are one or the other.
Envelope entrepreneurs get joy from focusing on the container: fundraising and go-to-market strategy, org charts and operating models. Letter entrepreneurs focus on what’s inside, on the product itself and the craft and care that goes into what the user actually touches. Too many founders, Fried argued, with time, get seduced by the envelope and forget about the letter.
The metaphor maps cleanly onto engineering management, especially in the light of flattening. There are envelope managers, whose days are filled with coordination and process, reporting upward and shielding their teams from organisational noise. And there are letter managers, in the details of the work, making judgement calls, bringing technical depth, and adding value through the craft of creating the product.
Most of us are some blend of the two, but the blend matters, as two forces are shifting it in ways that are hard to ignore.
Here’s what we’ll cover:
What envelope management looks like. The coordination, process, and shielding work that fills most managers’ calendars, and why this is becoming outdated.
What letter management looks like. Substance, craft, and judgement, with concrete examples from leaders who embody it.
Why the balance is shifting. Flattening organisations and AI automation are compressing the envelope, and we need to broaden the scope of our roles.
The honest assessment. A self-diagnostic for figuring out where you sit.
Becoming a letter manager. Practical steps for shifting the balance, if you haven’t already.
The envelope still needs delivering. Why you can’t just abandon coordination, and why nuance matters in everything.
If you’d like to dig deeper into related themes, here are some articles from the archive:
Being in the details is the strongest existing piece on what I’m calling “letter management” here: staying close to the work, knowing the architecture, driving the product forward.
Should managers still code? explores the distinction between being in the code and writing code, and why every manager should be at least doing the former.
Going direct covers removing unnecessary intermediaries, which directly reduces envelope work.
New advice for aspiring managers argues that the purely delegated manager may not be a thing anymore, which we expand upon in this article.
Let’s get into it.
What envelope management looks like
Before we name what’s changing, let’s touch on what management, up until only a few years ago, typically consisted of. If you tracked your calendar for a week and categorised every activity, you’d probably find that the majority falls into what Fried called envelope work: the container around the substance.
Envelope work includes scheduling meetings, writing status updates, managing stakeholders, allocating resources, flagging risks to leadership, facilitating discussions, and absorbing the chaos so your team doesn’t have to. It’s the work of coordination, making sure the right people know the right things at the right time, keeping things moving.
None of this is bad. It’s necessary, often thankless, and someone has to do it. The problem is when it becomes all you do, when your entire worth as a manager is routing information between people who could talk to each other directly.
As I explored in Going direct, many of the intermediary layers we’ve built in organisations exist out of habit rather than necessity.
There’s a historical reason for this; one I traced in my book Become a Great Engineering Leader. The origins of organisation design go back to the railroads, where staff were distributed across vast distances and org charts were the only mechanism for coordinating communication. Those structures made sense in a pre-technology world.
In a remote-able world with the collaboration tools we have today, we don’t necessarily need complex org charts and layers of management to get things done anymore, yet many organisations still operate as if we do.
One useful test is to ask what would break if you disappeared for a week. If the answer is “meetings wouldn’t get scheduled and status reports wouldn’t get written,” you’re doing primarily envelope work. When the answer is “technical decisions would stall and the team would lose direction,” you’re doing letter work. Most managers, if they’re honest, would find their absence felt more in the former category than the latter.
The envelope manager isn’t a caricature. It’s the natural gravitational pull of the role, especially in the pre-AI era, and in some organisations (particularly large or heavily bureaucratic ones) it’s often structurally imposed rather than explicitly chosen by leadership.
Organisations generate coordination work the way engines generate heat: it’s a byproduct of complexity, and someone always ends up absorbing it. The question is whether that’s the best use of your time, or whether you’ve been so busy working on the envelope that you’ve forgotten to write a letter for a long time.
What letter management looks like
What’s inside the envelope? Letter management is the substance of the role, the craft, the judgement, the deep engagement with the actual work your team is doing. It’s the part of management that requires you to know things, not just to coordinate things, and it’s all about being in the details, which I’ve written about numerous times before as a yardstick for where our roles are going.
Some of the notable thinkers in engineering leadership have been articulating this for years, even if they didn’t use the envelope and letter framing. Charity Majors has long argued through her “engineer/manager pendulum” that engineering managers need technical skills fresh enough to “independently evaluate their work, guide their development, and resolve technical conflicts.”
When you outsource that judgement to a tech lead because you’ve lost the technical thread, you’re allowing your technical ability to diminish: you’re an envelope manager wearing a letter manager’s mask.
Jeff Bezos codified a similar instinct as Amazon’s “Dive Deep” leadership principle: “Leaders operate at all levels, stay connected to the details, audit frequently, and are sceptical when metrics and anecdote differ.” When the anecdotes and the data disagree, Bezos argued, the anecdotes are usually right. You can only know that if you’re close enough to the work to understand the anecdotes in the first place.
And then there’s Andy Grove’s leverage equation from High Output Management: a manager’s output equals the output of their organisation plus the output of the neighbouring organisations under their influence. The key variable is leverage, and letter skills (coaching, technical contribution, vision, difficult decisions) create higher leverage than envelope skills (scheduling, status reporting, stakeholder management).
An hour spent reviewing architecture (perhaps through inversion) with your team compounds differently than an hour spent updating a project tracker.
The common thread is proximity to the work. Letter managers aren’t managing from a distance, processing reports and relaying summaries. They’re close enough to the substance that their involvement makes the work better.
As I wrote previously, being in the details means knowing enough about what your team is building that you can ask the right questions, spot problems early, and make judgement calls that a pure coordinator never could. That’s not micromanaging. It means being able to be a technical peer as well as a manager.
Why the balance is shifting
Envelope work and letter work have always coexisted, but the balance is shifting. Two forces are compressing the envelope, and neither shows signs of slowing down any time soon.
The great flattening
The first force is structural, i.e. how companies are thinning and reforming. Post ZIRP, organisations are getting flatter, and the management layers that existed primarily to coordinate and relay information are being removed.
Middle managers made up 30% of all layoffs in 2023, up from 20% in 2018. Amazon set out to cut around 14,000 managerial roles in 2025, with CEO Andy Jassy explicitly targeting a 15% increase in the ratio of individual contributors to managers. Microsoft, Citigroup, and UPS all followed the same pattern.
The layers being removed are disproportionately envelope layers: managers whose primary function was to collect information from one level and relay it to another. When organisations flatten, the coordination work doesn’t disappear entirely, but it gets redistributed, automated, or stripped away as unnecessary. The managers who survive are the ones who were doing letter work all along.
AI eats the envelope
The second force is technological, and, as you know, it is coming at us like a tsunami. Gartner predicted in late 2024 that by 2026, 20% of organisations would use AI to flatten their structures, eliminating more than half of current middle management positions. Their reasoning was blunt, and it reads like a definition of envelope work. “A large portion of their work involves reading reports, analysing data, and translating information between layers of the organisation.”
The data supports it. A Harvard Business School study found that after AI tool adoption, coding activity rose by 5% while project management activity fell by 10%. The specific tasks being automated read like an envelope manager’s job description: status updates, scheduling, progress tracking, risk flagging, meeting summaries, and resource allocation. And studies aside, I’m sure you’ve just experienced this first-hand in your day-to-day work.
The identity crisis
These two forces are creating what could be called an identity crisis for engineering managers. Will Larson captured this. “We’ve flattened engineering organisations where many roles that previously focused on coordination are now expected to be hands-on keyboard. The best managers of the prior era are now reframed as bureaucrats rather than integral leaders.”
That reframing is painful, because countless managers built their careers on envelope skills (coordination, stakeholder management, organisational navigation) that were valued, and in many organisations still are. But the ground is shifting. A recent LeadDev panel surfaced the “senior identity crisis” of managers asking “if I’m not writing code, what am I?”, with one panellist observing that “the golden age of the engineering manager, focused on team happiness and productivity, seems to no longer exist.”
Here’s the rub. If what you offer is the envelope, you’re competing against AI tools that can do it faster and against organisations deciding they don’t need as many layers of it. If what you offer is the letter, you have something that can’t be automated, something that only grows more valuable as the layers around it come off. That’s the bet worth making as the org chart keeps thinning.
What about you?
Where do you sit? This section requires some deep introspection, because most of us overestimate how much letter work we’re actually doing. What we think about and what we actually do can be two different things: we remember the one architecture review we did last week and forget the twelve status update meetings that surrounded it (been there, done that).
Patrick Lencioni draws a useful distinction in The Motive between two types of leaders. Reward-centred leaders are drawn to the status, compensation, and influence that come with the title. They gravitate towards the parts of leadership that feel important (the meetings, the decisions, the visibility) and avoid the parts that are difficult or unglamorous (the code, the friction, and the bottlenecks).
Responsibility-centred leaders see leadership as an obligation: they do the hard things precisely because they’re hard, and because nobody else is going to do them.
It’s not hard to see how this maps onto envelope and letter management. Reward-centred leaders tend to be envelope managers: drawn to the coordination and stakeholder work because it’s visible and keeps them in the room where decisions happen. Responsibility-centred leaders tend to be letter managers: they do the uncomfortable work that actually changes outcomes, getting their hands dirty alongside their team.
Most managers will agree that substance matters more than coordination. The harder test is whether your calendar reflects it.
For this exercise, look at your calendar and inboxes for the past two weeks and categorise each block as ruthlessly as you can: was it envelope work (coordination, status, facilitation, shielding) or letter work (technical review, coaching with depth, making a judgement call, pair programming with the ICs on your team)?
There is a nuance worth keeping in mind as you do it. A one-to-one where you discussed career goals is letter work, while a one-to-one where you relayed project updates from another team is envelope work. The ratio between the two will tell you something useful about where your time actually goes.
