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Posts tagged “leadership”

You are not your team’s umbrella

Two recent articles about engineering management stuck with me because they complement each other well to articulate a leadership philosophy I’ve held for a long time, but haven’t been able to put into words effectively.

First, in The Disappointment Frontier James Stanier expands on a controversial quote: “leadership is disappointing people at a rate they can absorb.” He talks about how keeping teams in a “bubble of protection” (where you act as the “umbrella” for bad news) never ends well. And even though managing disappointment is a core leadership skill, it is typically overlooked when training new managers. It’s worth reading the whole article, but here is a key point:

Managing a team of any size—from a handful of people to a whole company—is a continual balance between trying to empower people to achieve what they want (interesting projects, plentiful opportunities, a plethora of pay increases and promotions) whilst navigating a conflicting reality that doesn’t always want to give it to them. As such, there is a lot of truth to the quote at the beginning of the article. Leadership is about disappointing people at a rate they can absorb. In fact, I think that I’ve likely spent far more time on mitigation of disappointment or on managing expectations than I have on being motivational in my management career.

James goes on to give some really good advice on how to manage disappointment well. The second article is Will Larson’s Unexpected Anti-Patterns for Engineering Leaders, in which he also discusses the dangers of the “umbrella” approach:

The more senior the teams I’ve worked with, the more I’ve come to believe that protecting your team from reality just makes things worse for them in the long term. Larson now tries to throw his team into the gory details much more quickly. “In the past, I used to think I was energizing my team by sparing them the details. But now it feels like lying to them,” he says. On a tactical level, Larson adjusted this habit by buffering less information. “That means even if it’s disappointing for folks, I’d rather them process news bit by bit, rather than deal with a huge ocean of mess all in one moment.”

Obviously you are not going to tell your team every little thing that happens in your day and your meetings. But the idea that we should shield our teams from the realities of an organization is fundamentally flawed and ultimately does a huge disservice to people. If we hide the context of our decisions or guidance we lose the trust of our team—and once that happens, all is lost. This approach also stunts growth. If we don’t prepare people for how organizations work, their eventual exposure to reality will be a huge shock and we would’ve lost out on the opportunity to coach them slowly over time.

I once received some performance review feedback that I am “too transparent” with my teams, and I need to dial that down a bit. I respectfully declined. I don’t know of any other way to be—both as a human and as a manager. I also firmly believe I would be a worse people manager if I adopted that feedback.

That said, transparency is a skill. One I’ve cultivated for many years, and will likely never fully master. How and when you say things matter, and it takes time to learn those nuances. The above articles give some great advice on how to start that journey with your teams. So I encourage you to give transparency a try. I think you’ll find that you immediately become partners with your team members, as opposed to just their “boss.” And you will make magic together once that happens.

Generative AI Is Not Going To Build Your Engineering Team For You

Charity Majors makes some really interesting points about the consequences of “replacing” junior engineers with AI:

By not hiring and training up junior engineers, we are cannibalizing our own future. We need to stop doing that. People act like writing code is the hard part of software. It is not. It never has been, it never will be. Writing code is the easiest part of software engineering, and it’s getting easier by the day. The hard parts are what you do with that code—operating it, understanding it, extending it, and governing it over its entire lifecycle.

Also:

To state the supremely obvious: giving code review feedback to a junior engineer is not like editing generated code. Your effort is worth more when it is invested into someone else’s apprenticeship. It’s an opportunity to pass on the lessons you’ve learned in your own career. Even just the act of framing your feedback to explain and convey your message forces you to think through the problem in a more rigorous way, and has a way of helping you understand the material more deeply. And adding a junior engineer to your team will immediately change team dynamics. It creates an environment where asking questions is normalized and encouraged, where teaching as well as learning is a constant.

Lots more in the full article, it’s well worth a full read.

Invested in the WFH argument? Home in on the evidence

I really don’t know how much more data we need about this. It’s almost as if RTO is not about productivity at all…

Bloom and Han reported last week in the journal Nature that, over the subsequent two years, hybrid workers showed no difference in performance grades or promotion prospects compared to office-bound colleagues; the company’s computer engineers, for example, did not differ in their coding output across the two groups.

Hybrid workers, however, reported higher job satisfaction and were less likely to quit, especially if they were non-managers, female, or had long commutes. The authors conclude that “a hybrid schedule with two days a week working from home does not damage performance”, adding the result would probably extend to other organisations.

Can Every Sales-Driven Company be Transformed to Being Product-Led?

Some solid points in this article from Jason Knight. On product-led vs. sales-led (but could also refer to engineering-led) organizations:

To be honest, my strong opinion is that if you have to worry about who’s “leading” anything, then you’ve got bigger problems to worry about than who’s leading. If your entire company is aligned around what’s important and how to get there, then anyone could “lead” you there. This is supposed to be a collaboration, not a dictatorship. If one team “leads” and others don’t agree with where they’re being led, fix that! I generally find that misalignment is one of the most important problems to solve in any struggling company.

Hard agree with that one. I don’t believe in “healthy tension” between product and engineering. Just like I shy away from the traditional hierarchical view of “bosses tell employees what to do”. Whether it’s Product and Engineering or Manager and Teammate… it’s about partnership and helping each other (and the company) grow. We have to reframe this idea that adversarial relationships somehow create better teams and products.

What the Challenger Disaster Proved

Emma Sarappo has a fascinating review of a new book about the Challenger space disaster (gift article). It is the first global disaster I was old enough to witness and experience in real time, and I’ve never been able to get those images out of my head. This review (and book) shines a horrifying light on the many human failures (mainly due to hubris) that resulted in this tragedy:

These issues—faulty O-rings, foam strikes—were understandable. Theoretically, with study and ingenuity, they were fixable. The problem was not really a lack of technical knowledge. Instead, human fallibility from top to bottom was at issue: a toxic combination of financial stress, managerial pressure, a growing tolerance for risk, and an unwillingness to cause disruption and slow down scheduled launches.

(Side note, tell me that last sentence doesn’t remind you of software development sometimes…)

Also, the astronauts knew what was happening:

The astronaut assisting them into place and finishing final preflight checks “looked down into her face and saw that her Girl Scout pluck had deserted her,” he writes. “In her eyes he saw neither excitement nor anticipation, but recognized only one emotion: terror.” She would fly for 73 seconds before the shuttle broke apart in a fireball and a cloud of smoke. After that gut-wrenching instant, and more seconds of stunned silence, a NASA public-affairs officer would speak the understatement that would become famous: “Obviously a major malfunction.”

Link roundup: leadership anti-patterns, communication when trust is low, clarity for product managers

I’ve been pretty bad at sharing what I’m reading over the past couple of weeks, so I wanted to do a quick roundup post of some articles I have found helpful recently. I keep wanting to write longer posts about each, but it’s just not happening due to time constraints, and I need to clear out that queue, so here goes!

Unexpected Anti-Patterns for Engineering Leaders

Insightful post by Will Larson with some great advice for all leaders, including a reminder that it’s not a good idea to extract yourself from the details completely:

New engineering managers are often advised to “step away from the code.” But an extremely high-functioning exec understands the domain they are operating in at some level of detail. As you get too far out of the details, you just become a bureaucrat. Too many well-meaning engineering managers end up as bureaucrats.

The Busy Trap: How to Distinguish Being Busy from Being Productive

This one deserves a thorough read, because it talks about maximizing throughput in systems—and it’s not about making sure everyone on the team is at 100% capacity:

The real bottleneck isn’t in doing the work but in the waiting—queues that turn days of development into weeks of delay. This insight shifts the focus from individual busyness to process efficiency and the smooth flow of work from start to finish. Our findings debunk the myths that more planning, parallel tasks, and pull requests guarantee better outcomes. Instead, they emphasize the need for streamlined processes and effective collaboration to enhance true productivity. Let’s prioritize making each moment count towards faster, more efficient delivery, moving beyond mere activity to meaningful progress.

How to Communicate When Trust Is Low (Without Digging Yourself Into A Deeper Hole)

Lots of things in this post that I found very relevant and helpful. I especially have a… well, “growth edge”… in this area:

To the best of your ability, try to resist reading layers of meaning into textual communication; keep it simple, overcommunicate intent, and ask for clarity. And if someone is asking you for clarity, help them do a better job for you.

And related…

You vs. the forgetting curve

My friend and former colleague Fio with another excellent newsletter edition about why we should be ok with having to repeat ourselves a lot:

And it’s not that other people forget because they are selfish or don’t care—it’s because we plonked a bit of information at the top of their forgetting curve […] Because the forgetting curve exists, being an effective communicator might well require us to share the same information multiple times, at the right intervals, across different channels, without ever assuming that our teams and stakeholders will magically remember everything after the first iteration.

Principles of Engineering Culture at Wealthfront

I love (most of) these principles, but especially this one:

We believe our organization is most healthy when engineers, not management, propose and drive platform improvements. New products and problems are often brought to engineering teams to solve, but then technical leadership of these teams interweave these priorities with necessary infrastructure as part of their platforms’ continued advancement in engineering quality. While it is the team’s job to propose and defend these improvements, it is then management’s job to internally align and clear the path for the improvements to happen. The alternative would be for management to command infrastructure projects that teams then find time to execute. Such management decrees are avoided as they lead to poor trade-offs and unhappy teams.

Clarity for Product Managers: Part 1, Directional Clarity

Great series by Arne Kittler. This quote stood out to me because I’ve been surprised at how many people I’m currently interviewing for roles on my team cannot succinctly describe what value PMs bring to an organization:

Imagine you meet your CFO in the elevator: How well can you briefly and convincingly tell them what you are doing and why, and what the company will gain from it?

The Moral Economy of the Shire

On the non-work side of things, I adore real-world critiques of fictional worlds, like this one:

The implication in both books and movies is that most Hobbits spent their time either farming or enjoying leisure time, but this makes little sense, when one considers what we know about premodern agriculture and what little of life and culture in the Shire.

We have to realize that Bilbo and Frodo were independently wealthy…

Bilbo and Frodo are both gentlemen of leisure because the Baggins family is independently wealthy, and that wealth almost has to come from land ownership, because there isn’t enough industry or trade to sustain it. They can afford to go on adventures and study Elven poetry because they draw their income from tenant farmers renting their land.

Don’t cancel your 1:1s

I’ve linked to and written about the importance of 1:1 meetings before, and here’s another reminder:

The long game of building a thriving team is in showing up for your people week after week, and intentionally holding that space. You will not always see the value in each 1:1 right away. Your people might need help, too, to understand how to use them effectively. But over the long run, the benefits of an engaged and thriving team are immense.

I’ve been guilty of this before, but I’m making a new commitment to myself and my teams. Even if you “don’t really have anything this week”, keep the meeting. It’s in the consistency of showing up that trust and relationships build.

Employers re-examine wellbeing strategies

You don’t say…

Before providing employees with solutions to manage their stress, Fleming recommends that employers do more to tackle the ways in which their business might be causing the stress. A Deloitte survey of US workers, in 2022, found three systemic factors had an “outsized impact” on wellbeing: leadership behaviour; job design; and organisational working practices. It prompted the researchers to conclude that “perks and programmes”, alone, achieve little.

No Wrong Channels

I really like this No Wrong Doors approach, and I think we can learn a lot from it in modern knowledge organizations:

Some governmental agencies have started to adopt No Wrong Door policies, which aim to provide help–often health or mental health services–to individuals even if they show up to the wrong agency to request help. The core insight is that the employees at those agencies are far better equipped to navigate their own bureaucracies than an individual who knows nothing about the bureaucracy’s internal function. […]

Something I’ve been thinking about recently is how engineering organizations can adopt a variant of the No Wrong Doors policy to directly connect folks with problems with the right team and information. Then the first contact point becomes a support system for navigating the bureaucracy successfully.

The Slackification of the workplace has, among other things, resulted in too many different places someone might be able to go for help. It’s frustrating to be sent from team to team, with no one really taking the time to understand and assist with the problem. What if we took a “No Wrong Channel” approach instead? I know it takes a bit of extra time, but I think it’s a worthy goal to become “a support system for navigating the bureaucracy successfully” when someone wanders into our team channel with a question that is not necessarily in our direct sphere of influence.

A few tips for job seekers

Updated February 27, 2025

I am in the process of hiring for a couple of roles at Cloudflare, so I’ve been talking to a lot of candidates over the past few weeks. I noticed a few trends along the way, so I thought I’d share a quick list of tips for anyone who is currently in the job market. This is obviously just one hiring manager’s opinion, but hopefully there’s something helpful for folks here!

  • Fill out your LinkedIn profile. So many people have empty LinkedIn profiles that just show their roles with no other details. Even if there is detail in your resumé, the LinkedIn profile is often the first thing I look at. It’s an opportunity to get to know you a little bit more than the formality of a resumé usually requires. Make sure the details about your responsibilities—and some outcomes and achievements—are listed within each position.
  • Write a summary paragraph at the top of your resume. Possibly the most impactful resumé post I’ve read in recent years is Austin Belcak’s How To Write A Resume Summary That Works In 2024 . He explains in detail the importance of these 3–4 bullet points (he calls it a “highlight reel”) at the top of your resume—before you even get to the details of your previous roles.
  • Write 1 sentence about each company in your history. This is true for all companies you’ve worked at, but especially smaller startups. It takes quite a while to Google every company someone has worked for, so it’s super useful to include a brief summary of what the company does. For instance, I would describe Jeli.io as “Incident management platform for incident response teams and their stakeholders.”
  • Send a note to the hiring manager if you know who it is. This works, if you do it right (see the next tip…). I have over 2,000 applications across roles right now, so there is no way to look at every single resumé. If people reach out with a message about their interest it’s a good signal that it’s someone who is excited about the role, which is one of the big things I’m looking for.
  • Do not, under any circumstances, use ChatGPT to write your outreach or cover letter for you. This should go without saying by now, but so many letters and notes are clearly written by ChatGPT. If you read as many of these as some of us do it’s really easy to spot. It’s about the cadence and the words—so much “utilizing” and “enhancing”!—and the particular style of grammar. We want to get to know you. Use your own words.
  • Learn about the company and the hiring manager before your first chat. I want to work with people who are excited about the job. I want to know if this is one of a thousand applications, or something they are truly interested in. I know it’s not possible to spend hours on research for every single call. But a little bit goes a long way.
  • Answer questions succinctly, and then stop. I know interviewing is stressful, and sometimes it’s hard to come up with answers on the spot. But the strongest candidates are able to distill their thoughts into a few short sentences, clarify some things if they need to, and then let the answer rest. Don’t keep saying words just to fill the space. Rather ask a question back, or wait for the interviewer to finish their notes and ask the next question.

I also feel like it’s important to point out that I truly believe the hiring manager / candidate relationship should not be an adversarial one. Hiring managers want someone who will be great for the role just as much as candidates want a role they love. No one wants a mismatch that’s not going to work out. So we have to help each other out. As hiring manager I have to be transparent about the role, the team, and the process. And candidates can help by providing enough relevant information to help us figure out who would be good to explore that fit with.