A few tips for job seekers

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.
  • 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.

Do we need to be honest about Fridays?

I’ve been very interested in the rise of the 4-day workweek (4DWW) ever since we adopted it in a previous company and saw the benefits and value it brought to our business. In Do we need to be honest about Fridays? Bruce Daisley makes an interesting observation about how the 4DWW might eventually sneak up on most businesses:

I’ve met several organizations who use Friday as a meeting-free day (to allow team members to chow down on emails and admin). Others tell me that their Fridays are a much slower pace, where meetings peter out mid-morning. […] So, let’s be real, is this how the reality of a four day week will take hold for most of us? That Friday will be kind of a catch-up day for those who need it but that many of us will work at half speed, casually ‘keeping an eye on things’.

Generative AI Is Totally Shameless. I Want to Be It.

Yes, I’m a relentless fanboy of whatever Paul Ford writes, but this is a truly wonderful post about what makes AI so addictive and impossible to look away from. He frames AI as a technology that truly has no shame because “it possesses an absolute willingness to spout foolishness, balanced only by its carefree attitude toward plagiarism.” And so:

By aggregating the world’s knowledge, chomping it into bits with GPUs, and emitting it as multi-gigabyte software that somehow knows what to say next, we’ve made the funniest parody of humanity ever. These models have all of our qualities, bad and good. Helpful, smart, know-it-alls with tendencies to prejudice, spewing statistics and bragging like salesmen at the bar. They mirror the arrogant, repetitive ramblings of our betters, the horrific confidence that keeps driving us over the same cliffs. That arrogance will be sculpted down and smoothed over, but it will have been the most accurate representation of who we truly are to exist so far, a real mirror of our folly, and I will miss it when it goes.

We Need To Rewild The Internet

I finally read this very long essay about Rewilding the Internet that’s been making the rounds. It’s about 30 mins of your time and in my opinion it’s time well spent.

It’s about what internet-builders can learn from the field of ecology, where the word “rewilding” has a very specific meaning. It’s essentially about systems thinking, which I know a lot of us care about deeply.

Rewilding the internet is not a nostalgia project for middle-aged nerds who miss IRC and Usenet. For many people across the generations today, platforms like Facebook or TikTok are the internet. They’ve long dwelled in walled gardens they think are the world. Concentrated digital power produces the same symptoms that command and control produces in biological ecosystems; acute distress punctuated by sudden collapses once tipping points are reached. Rewilding is a way to collectively see the counterintuitive truth; today’s internet isn’t too wild, even if it feels like that. It’s simply not wild enough.

In the end, I can’t help but think that though I love these ideas, it’s just… too late. I hope I’m wrong though.

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.

If you’re doing their job, who’s doing your job?

Melissa and Johnathan Nightingale have some hard truths about what happens when leaders take on too much of their team’s workloads in If you’re doing their job, who’s doing your job?

But now we have an overwhelmed team working for an overwhelmed boss. This is where cheap problems go to get expensive. You are chronically unavailable because you’re slammed. Your team can’t get your attention on a thing so they make their best guess. Their best guess turns out to be wrong. All the work needs to get redone. […]

As a manager at any level in an organization, a key part of your job is figuring out how to get the most important things done for the organization. Yes, the hard part of that job is sometimes the doing, and you can pitch in. But when your team is overwhelmed, when there is structurally too much to do, it’s your job is to figure out what’s most important. Where is that work happening?

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.

How to move into Product Management at your company

I am currently in the process of hiring a product manager for my team at Cloudflare. One of the neat things about Cloudflare is that internal candidates are encouraged to reach out to hiring managers to chat with them about the role. That means that I’ve had several really great conversations with colleagues over the past couple of weeks, many of them with folks who are in other parts of the org like BI, customer support, finance, engineering, etc. The question they have is, “how do I move into product management?”

It’s a great question, and after I’ve given the same answer a few times, I decided to just go ahead and write it down in our internal wiki as well. Below is a lightly edited version of the advice I shared, in case that’s helpful to anyone else who is trying to move into the PM role at their company:

  • If you’re brand new to the job I have a couple of book recommendations to get a general sense of what good product management looks like. I recommend starting with Inspired by Marty Cagan, and Escaping the Build Trap by Melissa Perri. You’ll hear these two books mentioned a lot in our field, and they are classics for good reasons. After that, read everything you can get your hands on (but stay away from LinkedIn Influencers, that’s mostly ChatGPT content these days). For more book/newsletter recommendations, I have a running list here.
  • Then—and this is the most important advice I have—do the job before you have the title. Every role can be expanded into some area of product management. Think deeply about the product(s) you support, what customers need, how it contributes to the business, what could be better, what you think the long-term strategy should be. Start exercising the PM muscle so that when the right role comes along internally, you’re ready for it.
  • Publish your thinking. Every company has an internal wiki, many with personal spaces. Use it. If you have an idea for a product, or an analysis that’s interesting, or some thoughts on future strategy, write it down, publish it, and share it with the PM who works on that product. This is the best way to practice for the job—clear, succinct communication is a crucial skill, so this exercises that muscle as well.

If you learn the craft, practice the craft, and show publicly that you can do the craft, you’ll be well on your way to moving into product management at your company. When a good job rolls around you’ll be able to point towards the work you’ve done to give hiring managers a sense of your product skills.

And lastly, this is a great job. You will love it!


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