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Posts tagged “career”

Managing Up

Michael Lopp has a great post about “managing up”, including how problematic that term is:

To me, “Managing Up” has that “your boss’s job is more important than yours” feel, which pisses me off. Your boss’s job isn’t more important than yours; it’s different.

He goes on to share some great advice for what to share with your manager, and when. For instance, when to share something immediately:

Unexpected developments. A situation appears in front of you, a non-threatening one but unexpected. Strange. Something is up, but you can’t discern the backstory story or the intent. It is unfamiliar. Tell your manager. Now. Just a brief note. A heads up. It’s probably nothing—it usually is—but there is a chance your manager’s context plus your suspicions equals additional clarity.

A career ending mistake

This is lovely post by John Arundel (“Come for the schadenfreude, stay for the thought-provoking advice” indeed!). I especially like the section on how to become a good manager:

If you want to become a great manager, which I think is the only kind worth being, start practicing now. Learn people skills, communication, collaboration, psychology. Work on understanding the things that make different kinds of people tick. Manage yourself excellently. If you can’t organize yourself, how do you expect to be responsible for a team?

"The kids are too soft"

This is another amazing AHP essay, this time about the critiques of Gen Z employees:

I’ve long argued that the critique of younger generations is a sublimated critique of a generation’s own parenting and child-rearing practices: no one wants to admit that the decisions they made (or tacitly endorsed) are responsible for the type of worker they find objectionable. But that sort of introspection requires, well, work.

It’s well worth reading the whole thing, but I also wanted to highlight the recommendations for what we (Gen X, etc.) can do about this:

So how do we break this cycle? If, upon encountering or even considering the attitude, ambition, or “work ethic” of a younger generation, your impulse begins to drift towards they don’t work like we do, my hope is we consider the following:

  • How have we, as a society — and how have I, as a leader — helped foster the conditions that encourage someone to work a certain way, with certain habits, or attitudes, or ambitions?
  • How much of my reaction is to the fact that someone is not working exactly the way I did at that point in my life — even though my circumstances were almost certainly wildly different?
  • How has our society — or our industry — tacitly agreed on an understanding of excellence that has little room for different ways of navigating the world, of making space to care for others, or collectivism just generally?
  • What if working differently is also an attempt to keep people in the industry for longer — and make the industry as a whole more sustainable?
  • What can I learn from the way they’re approaching work?

Why competent workers become incompetent managers

This isn’t a new revelation, but it’s helpful to see research to back up how important good managers are:

Managers play a crucial role in shaping an employee’s experience. For example, research shows that nearly 70% of the variability in employee engagement can be predicted by their managers’ behavior, decisions, and personality traits. In other words, whether people are happy, energized, or miserable at work depends mostly on their boss—and whether or not they’re an incompetent manager.

The article goes on to talk about the well-known Peter Principle, which states that “employees are promoted based on their success in previous jobs until they reach a level at which they are no longer competent”:

One of the core mechanisms behind the Peter Principle is the gap between the skills needed in junior technical roles and those newly and additionally required in senior and managerial positions. To improve the promotion system, especially for significant promotions for team leader or line manager roles, it’s essential to consider a person’s past performance or technical expertise and leadership potential, such as collaboration experience or services to the team. Organizations can counteract the Peter Principle through comprehensive training programs that equip employees with necessary competencies, such as people management skills, strategic thinking, and emotional intelligence before promoting them to managerial roles.

It’s mind-boggling how often organizations promote individual contributors into manager roles without any training at all. This is a major contributing factor to the Director problem so many orgs are battling with right now:

Your organization will succeed or fail on the basis of your director layer. And in most organizations, that layer is a mess right now.

Replacing my Right Hand with AI

I like Erik’s thoughts about AI and coding in Replacing my Right Hand with AI:

I do think that AI will lower the bar for anyone to be able to create software, just like anyone can use Excel to do their own personal accounting. This is a good thing!

And:

Human engineers won’t go away. We’ll still be needed to drive high-level prioritization, understand the overall architecture and scope of the problem, and review the AI’s work, especially as systems get bigger. But we’ll spend much more of our time thinking about what to build, and much less on the repetitive “how” of building it.

On the Product side of this argument, there is Paweł Huryn’s Will We Lose Our Jobs to AI? Cutting Through the Hype. Short answer: no! But he makes some points about how we should adapt that I agree with, especially these two:

  • Educate yourself in AI: You should understand concepts like fine-tuning and AI agents, but there’s no need to obsess over them. YouTube videos are perfectly fine unless you want to tie your career more closely to AI.
  • Get interested in the business side of the product: How do your organization’s Sales, Success, and Support teams work? How exactly does your company make money? How do you acquire customers? What are the key acquisition, retention, and revenue metrics? How do these metrics differ depending on the customer segment? How have they changed over time? Who are your competitors? What’s unique about your strategy?

In short, use AI for the things that it is good at, and get better at the things that it’s not good at.

High-reaching informality and the difference a good manager makes

Neil Perkin tackles some important leadership points in High-reaching informality (emphasis mine):

Overly formal environments are more likely to be low in psychological safety, and less likely to encourage people to speak up, contribute their ideas, and challenge assumptions or norms. Informality helps to break down barriers, reduces the toxicity and influence of internal politics, helps a team to get the best ideas and to be adaptive in delivery to arrive at better outcomes. […]

It’s useful to think of psychological safety as the bringing together of mutual trust and respect, and also comfort with dissent. Overly or inappropriately formal environments reduce trust down to a transactional relationship: I asked you to do this, so did you do it? Whilst dependability is important, trust is also built on competence, confidence, integrity, and empathy.

This relates to something that’s been on my mind quite a bit over the past few weeks: the question of what it means to be “boss”. The “transactional relationship” that Neil describes above is one I will always avoid with all my heart with my teams.

I was lucky early in my career. When I first joined eBay I had a fantastic manager. He was empathetic and people-first, and yet strongly business-driven. He coached me, corrected me, taught me how to speak the language of business, challenged me… but above all, it felt like he was on my side. I had someone in my corner, someone rooting for me, someone to help me navigate a gigantic organization while I really felt like I had no idea what I was doing. He didn’t react negatively to bad news or frustrated questions, he simply said, “tell me more about that.” I will be forever grateful to Christian for the way he set me up for long-term career success.

20 years later I know just how lucky I was. From my conversations with teams and candidates over the past year or so it has become clear to me that very few people have the privilege of working with a good manager early in their career—someone who is supportive yet determined for us to do the best work of our lives, together. This seems particularly acute in the middle management layer1, where organizations spend very little time on training new leaders. From The Strengths, Weaknesses and Blind Spots of Managers:

Worldwide, the cost of poor management and lost productivity from not engaged or actively disengaged employees is $8.8 trillion, or 9% of global GDP. Changing how people are managed is perhaps the easiest way to boost productivity within organizations.

Yet, the majority of managers receive little feedback on how effectively they manage their team. Less than half of U.S. employees (42%) report having the opportunity to formally provide feedback to their manager, and fewer than one in four (24%) have formally rated their manager’s performance.

I’m not sure what the solution is, but I do think this is an important problem to call out and watch out for. Do you have transactional leaders in your company, or relational ones? The transactional leaders might initially appear to be more effective, but everything I’ve learned up to this point in my career has shown me that those benefits are short-lived, and almost always end up with disengaged, resentful team members. As leaders we are not here to tell people what to do. We are here to provide strategic direction and context, and coach our people—as part of the same team—on how to make the business and themselves successful for the long haul.

PS. If you’re looking for a book that covers these topics really well, give Good Authority: How to Become the Leader Your Team Is Waiting for by Jonathan Raymond a go.

Grow down

I love this reflection about personal resilience from Mandy Brown:

That is, we grow not only up—not only skyward—but down, into the roots, back to that from which we came and to which we will, one day, return. We become, in time, more rooted and resilient, more capable of surviving the storm, less easily shaken away from ourselves by idle wind or rain. When I think about growing down instead of up, I think about becoming centered, about knowing what work is ours to do (and, critically, what work is not), about a slow, steady power rather than a rash and inconstant one. After all, as anyone who’s ever lived among city trees can tell you, neither brick nor concrete nor iron can stop a root as it seeks out water. We should be as steady in our search for that which nurtures our own lives.

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.

The compounding, non-obvious value of doing exceptional work

In Crazy Charlie’s Window Michael Lopp says something that has stuck with me for a couple of weeks now (emphasis mine):

The reason, decades later, I frequently think of this unpaid weekend adventure sifting through a year of garbage, hardware, and knick-knacks is because it is when I discovered the compounding non-obvious value from doing exceptional work.

It’s a great story, well worth reading. Matthew Ström makes this point in a slightly different way in The polish paradox (again, emphasis mine):

The polish paradox is that the highest degrees of craft and quality are in the spaces we can’t see, the places we don’t necessarily look. Polish can’t be an afterthought. It must an integral part of the process, a commitment to excellence from the beginning. The unseen effort to perfect every hidden aspect elevates products from good to great.

Doing good work and getting the details right result in better outcomes, yes. But it’s about more than that. It’s not just about the job, it’s about us. The sense of accomplishment and purpose that comes from doing great work is an intrinsic reward that is life-giving far beyond the confines of our immediate job duties.

Constraints on giving feedback

Will Larson really got me thinking with his advice on the best ways to push your organization to improve. It’s essential work, but “organizations can only absorb so much improvement at a given time before they reject the person providing the feedback.” We have to balance the feedback about how to improve with guidance on how operate within the existing environment:

When I focused on how the environment could change to make my team more successful, I was usually technically correct, but usually didn’t help my team very much. Because work environments change slowly, it benefits your team more to give them feedback about how they can succeed in their current environment than to agree with them about how the current environment does a poor job of supporting them. Agreeing feels empathetic, but frames them as a bystander rather than active participant in their work.