Irrational...
Slides for Measuring an engineering organization.
Last week, I gave a 30 minute talk to a group of CTOs and VP Engineerings in San Francisco
about...
2 weeks ago
Last week, I gave a 30 minute talk to a group of CTOs and VP Engineerings in San Francisco
about measuring engineering organizations.
This talk was essentially this blog post,
and here are the slides.
A few topics worth highlighting:
Measurement educates you, and your audience,...
Irrational...
Poking around OpenAI.
I haven’t spent much time playing around with the latest LLMs,
and decided to spend some time doing...
a month ago
I haven’t spent much time playing around with the latest LLMs,
and decided to spend some time doing so. I was particularly curious
about the usecase of using embeddings to supplement user prompts
with additional, relevant data (e.g. supply the current status of their
recent...
Irrational...
How to plan as an engineering executive.
Some years back, I interviewed a senior leader for an engineering role, and asked them a question...
a month ago
Some years back, I interviewed a senior leader for an engineering role, and asked them a question about planning. I enjoyed their response, “Ah yes, the ‘P’ word, planning.” That answer captured an oft heard perspective that planning is some sort of business curse word. Even when...
Irrational...
Good hypergrowth/curator manager.
In 2016, I wrote Productivity in the age of hypergrowth to discuss the challenges of engineering...
a month ago
In 2016, I wrote Productivity in the age of hypergrowth to discuss the challenges of engineering management during periods of hypergrowth. Managers in such periods spend much of their time on hiring and onboarding, with the remainder devoted to organizational structure and...
Irrational...
Who runs Engineering processes?
Uber ran a tech spec review process called the DUCK Review. “DUCK” didn’t stand for anything–it was...
2 months ago
Uber ran a tech spec review process called the DUCK Review. “DUCK” didn’t stand for anything–it was created as a deliberate non-acronym–but was otherwise a fairly typical review process. When I first joined, we’d review one or two specs each week.
The volume of requested reviews...
Irrational...
Mailbag: What should you do if you report to an underperforming executive?
Recently, an email came in asking what to do when you report into a mediocre or underperforming...
4 months ago
Recently, an email came in asking what to do when you report into a mediocre or underperforming executive.
I’ve gotten variants of this question a number of times over the years, and it’s worth digging into a bit:
Have you written anything about working in middle management where...
Irrational...
Internal comms for executives.
Whenever an executive joins a new company, there is an awkward merger
between the executive’s...
4 months ago
Whenever an executive joins a new company, there is an awkward merger
between the executive’s preferred communication style and the norms that organization has already established.
I remember a recently joined executive complaining that engineers weren’t reading his emails.
He...
Irrational...
Balancing your CEO, peers, and Engineering.
There are so many stories of hiring a new executive who comes in and wreaks havoc. I’ve seen...
a month ago
There are so many stories of hiring a new executive who comes in and wreaks havoc. I’ve seen engineering leaders start with a giant, doomed migration, marketing leaders who accelerate expenses until they necessitate a round of layoffs, and a number of executives fired in their...
Irrational...
Grab bag of random thoughts.
A bit over a week from now, I’ll be joining a company to start a new role, and I wanted to ramble a...
a month ago
A bit over a week from now, I’ll be joining a company to start a new role, and I wanted to ramble a bit to braindump
the numerous loose threads in my head as I transitioned from Calm to the past month of full-time writing, and then
into this new role.
This isn’t really a job...
Irrational...
Extract the kernel.
As I’ve served longer in an executive role, I’ve started to notice recurring communication...
a week ago
As I’ve served longer in an executive role, I’ve started to notice recurring communication challenges between executives and the folks they work with. The most frequent issue I see is when a literal communicator insists on engaging in the details with a less literal executive.
I...
Irrational...
Interviewing engineering executives.
Earlier I wrote about getting hired as an Engineering executive, and it’s perhaps even more...
a month ago
Earlier I wrote about getting hired as an Engineering executive, and it’s perhaps even more important to discuss the opposite question: how should you interview and evaluate Engineering executives? As an Engineering executive, you may not directly run one of these searches, but...
Irrational...
Building your executive network.
In most of my roles, I’ve learned more from my peers than from my manager. Even when you get along...
3 months ago
In most of my roles, I’ve learned more from my peers than from my manager. Even when you get along well with your manager, your peers’ perspective will usually be closer to yours than your manager’s. Once you transition into an engineering executive role, you’ll still have peers,...
Irrational...
Running your engineering onboarding program.
Most companies say that it takes three to six months for newly hired engineers to fully ramp...
3 months ago
Most companies say that it takes three to six months for newly hired engineers to fully ramp up.
Engineering leaders know it’s impolitic to admit that it takes their team longer than three to six months to onboard new engineers,
so that’s what they say out loud, but they...
Irrational...
Safe defaults.
Back in 2018, when I first wrote about sizing engineering teams, I was surprised how much my advice...
4 months ago
Back in 2018, when I first wrote about sizing engineering teams, I was surprised how much my advice rankled a colleague. He wanted to spin up a new engineering team of two people, which I thought was a bad idea. It would be a fragile team that would fall apart quickly if it...
Irrational...
The Engineering Executive's Primer.
See on O’Reilly’s website for The Engineering Executive’s Primer.
In 2019, I worked with Stripe...
a month ago
See on O’Reilly’s website for The Engineering Executive’s Primer.
In 2019, I worked with Stripe Press to publish my first book, An Elegant Puzzle,
which captured many of the lessons I’d learned as an engineering manager in fast growing Silicon Valley companies.
In 2021, I decided...
Irrational...
Make an effective executive LinkedIn profile.
tl;dr - it’s valuable to update your LinkedIn profile to be a concise, accurate, and current summary...
4 months ago
tl;dr - it’s valuable to update your LinkedIn profile to be a concise, accurate, and current summary of your accomplishment. Spend at most two hours updating it, then ask a friend (ideally a recruiter) for feedback. Incorporate that feedback and don’t think about your profile...
Irrational...
How to capitalize engineering costs.
There are many important meetings in your first ninety days as a new engineering leader, but one...
5 months ago
There are many important meetings in your first ninety days as a new engineering leader, but one that’s both easy to forget and surprisingly important is your first meeting with the finance team. There’s a lot to learn from the finance team, particularly drilling into your profit...
Irrational...
Getting a job as an engineering executive.
I started my first executive job search when I was 25.
Eventually, I got an offer to lead...
4 months ago
I started my first executive job search when I was 25.
Eventually, I got an offer to lead engineering at a startup with four engineers,
which I turned down to join Uber.
It wasn’t until a decade later that I joined Calm and started my first executive role.
If you start...
Irrational...
2022 in review.
Previously: 2021, 2020, 2019, 2018, 2017
After the past two years, it’s odd to write an annual...
5 months ago
Previously: 2021, 2020, 2019, 2018, 2017
After the past two years, it’s odd to write an annual reflection where my first thoughts are happy rather than bleak.
The truth is that there is a lot of bleak out there right now–just look at the layoffs and the funding environment–but...
Irrational...
Using cultural survey data.
When I was at Stripe, I reworked the hiring process for Director-plus engineering managers.
My goal...
2 months ago
When I was at Stripe, I reworked the hiring process for Director-plus engineering managers.
My goal was to better evaluate polished senior leaders who always said the right thing.
I wanted to find the real beliefs and behaviors underneath all the polish.
One interview focused on...
Irrational...
What does it mean to be a cost center?
When I shared my piece on Measuring an engineering organization, one point I made was that focusing...
4 months ago
When I shared my piece on Measuring an engineering organization, one point I made was that focusing too heavily on optimization metrics (e.g. things like CI/CD time) can turn engineering into a cost center. That’s not because optimization metrics aren’t important, they’re...
Irrational...
Trying Plausible.
I’ve been wanting to spend some time trying out recent
developer and infrastructure tooling,...
4 months ago
I’ve been wanting to spend some time trying out recent
developer and infrastructure tooling, starting with taking Tailscale for a spin
(it’s quite nice).
Next, I’ve been thinking about replacing Google Analytics on this blog for some time,
and decided to try out Plausible.io as a...
Irrational...
Measuring an engineering organization.
For the past several years, I’ve run a learning circle with engineering executives. The most...
5 months ago
For the past several years, I’ve run a learning circle with engineering executives. The most frequent topic that comes up is career management–what should I do next? The second most frequent topic is measuring engineering teams and organizations–my CEO has asked me to report...
Irrational...
Setting engineering org values.
Uber’s best known corporate value is probably Super Pumped,
which, in addition to being a one-time...
4 months ago
Uber’s best known corporate value is probably Super Pumped,
which, in addition to being a one-time company value, is also the title of Mike Isaac’s account of Uber
and the subsequent television show.
However, for me personally, the value I remember most is Let Builders...
Irrational...
Onboarding peer executives.
While many companies build out an elaborate Engineering onboarding program, the process for...
2 months ago
While many companies build out an elaborate Engineering onboarding program, the process for onboarding new executives tends to be an ad-hoc, chaotic affair. There usually is an executive onboarding process, but it’s used too infrequently to ever get excellent.
Part of the problem...
Irrational...
Lessons not worth learning.
A few weeks ago I had a call with a startup founder who was frustrated with their team. The team...
5 months ago
A few weeks ago I had a call with a startup founder who was frustrated with their team. The team kept getting distracted by interesting work, and was avoiding the most important work to move the business forward. Was it possible to build a team that simply does the important work...
Irrational...
A brief rant on converging compliance regimes.
Although I’ve never worked exclusively on compliance, much of my work over the past decade has...
5 months ago
Although I’ve never worked exclusively on compliance, much of my work over the past decade has touched on reconciling between product and compliance goals, and over that time I’ve developed something of a pet theory on the evolution of compliance over the next five to ten years:...
Irrational...
ReadME contribution on reliability programs.
I was excited to contribute an article,
Move past incident response to reliability
to Github’s The...
3 months ago
I was excited to contribute an article,
Move past incident response to reliability
to Github’s The ReadME project.
This topic was particularly on my mind when I wrote it towards the end of last year,
when I was focused on my Infrastructure Engineering project.
That project is a...
Irrational...
Better to micromanage than be disengaged.
For a long time, I found the micromanager CEO archetype very frustrating to work with.
They would...
4 months ago
For a long time, I found the micromanager CEO archetype very frustrating to work with.
They would often pop out of nowhere, jab holes in the work I had done without understanding the tradeoffs,
and then disappear when I wanted to explain my decisions.
In those moments, I wished...
Irrational...
Deciding to leave your (executive) job.
If two friendly executives meet for dinner, it’s likely they start by exchanging just how messed up...
2 months ago
If two friendly executives meet for dinner, it’s likely they start by exchanging just how messed up things are at work.
Initiatives are behind, layoffs are happening everywhere, the team is in disarray.
Then they’ll laugh, and switch topics. Sometimes one of the executives can’t...
Irrational...
Engineering’s role in Mergers & Acquisitions.
I managed the engineering team at Digg as we ran out of money, and were eventually acquired. It was...
3 months ago
I managed the engineering team at Digg as we ran out of money, and were eventually acquired. It was an eye opening experience, and I learned a great deal about the reality and the optics of selling a company, particularly one with no money and a shrinking user base. Humbling was...
Irrational...
Culture vs systems.
Recently, I had a chat with a friend who was frustrated by their company culture. They’d been...
4 months ago
Recently, I had a chat with a friend who was frustrated by their company culture. They’d been pushing the company to operate with more urgency, but didn’t feel like it was landing. “How do we,” they wondered, “get the team to recognize that urgency is essential to our success?”...
Irrational...
Writing an engineering strategy.
Once you become an engineering executive, an invisible timer starts ticking in the background.
Tick...
3 months ago
Once you become an engineering executive, an invisible timer starts ticking in the background.
Tick tick tick. At some point that timer will go off,
at which point someone will rush up to you demanding an engineering strategy.
It won’t be clear what they mean, but they will want...
Irrational...
Trying Tailscale.
Like most folks working in infrastructure engineering in 2014, I really enjoyed Google’s BeyondCorp...
5 months ago
Like most folks working in infrastructure engineering in 2014, I really enjoyed Google’s BeyondCorp whitepaper. My foremost personal interest was grounded in the fact that Uber’s contemporaneous security implementation didn’t include a VPN, so it was interesting to see a...
Irrational...
Meetings for an effective eng organization.
Some engineers develop a strong point of view that meetings are a waste of their time. There’s good...
4 months ago
Some engineers develop a strong point of view that meetings are a waste of their time. There’s good reason for that perspective, as many meetings are quite bad, but it’s also a bit myopic: meetings can also be an exceptionally valuable part of a well-run organization. If you’re...
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