Lessons learned from my recent tech writing job hunt

Alyssa Rock — Tech writer. OSS community manager. DocOps enthusiast.
Aug 17, 2024, updated Sep 2, 2024 25 min read

I’m happy to say that I accepted a new role last month as a technical writer for a startup named Cribl, the data engine for IT and security. This new role comes at the end of a slow, silent hunt for a new job that I started as far back as August 2022. (Yes, you read that right: I’ve been quietly job hunting for nearly two years.)

I started casually job hunting in June 2022 after Broadcom announced their acquisition of VMware. I want to be clear that I have nothing against Broadcom and I respect many things about Broadcom corporate management. I appreciate their fiscal discipline and their strong drive to reduce layers of bureaucracy and middle management. Deciding to leaving Broadcom was very difficult. I miss my manager, my fellow tech writers, and my development team at Salt tremendously.

That being said, Broadcom has a well-known reputation for implementing large, rolling layoffs for companies they acquire. To me, it seemed statistically likely that I might get laid off at some point. So, I started proactively job hunting as early as 2022 in anticipation of that possibility. I didn’t job hunt very aggressively, only applying to opportunities that seemed interesting and a good fit. I figured that if the right job opportunity came along, I would take it. And the right job finally did come along! (Thank you for putting your trust in me, Cribl!)

So, in this blog post, I want to share some of the job-hunting lessons I’ve learned the last two years. This blog has three sections, in which I discuss:

  • The state of the job market for the tech industry today.
  • Job hunting strategies that helped my personal job hunt.
  • Final closing thoughts about the nature of job hunting itself.

If you’re familiar with my writing, you know that I write super long blog entries. But, as always, you don’t have to read every single word I write. You can definitely scan and skim! I have lots of headings in this post so that you can quickly scan and see which tips or sections are most interesting to you.

💥 The tech industry went from boom to bust (and the job market reflects that)

As I mentioned in my introduction, I started job hunting as far back as August 2022, which was just before the job market started to go sour for the tech industry. And make no mistake: it is definitely sour. As the era of free money ended and venture capital investment slowed (caused by the failure of Silicon Valley Bank and cryptocurrency), many small tech startups closed their doors and big tech began laying off workers.

Since the end of 2022 when big tech initiated multiple waves of massive layoffs, some estimates show that around 450,000+ tech workers have lost their jobs up to this point. While there have been some job gains to offset these losses, many people are still out of work and tech layoffs have continued. A few months ago, CNN estimated that the ratio of open jobs relative to the number of applicants on LinkedIn was 1:2, down significantly from the early 2022 ratio of 1:1 (one job for every seeking candidate).

Simply put, it’s harder to get a tech job now than it was during the height of the pandemic. And that means that the balance of power has shifted to employers. But that doesn’t mean that hiring managers are necessarily happy about these ratios either. Hiring managers frequently report feeling understandably overwhelmed by the larger pool of job seekers. It also hasn’t helped that there is an increased surge in applications because of the relative ease of finding and applying for jobs over the Internet.

In response, employers have responded with various tactics to cope with the deluge of applications:

  • More aggressive resume weeding, such as ATS resume screening.
  • Raising the bar of excellence, often expecting applicants to be a closer fit than in the past.
  • Longer, extended interviewing periods and processes, such as requiring multiple rounds of interviews or competency tests.
  • A disturbing trend in candidates being ghosted.

The best article that explained what I was feeling on the ground as a job hunter was this article entitled: What the heck is going on with the UX job market?. Even though it’s about UX, the job trends with UX design and technical writing tend to be fairly closely linked and often mirror each other. I recommend reading it if you’re looking to validate your sneaking suspicion that things are particularly bad in the tech industry job market right now. It’s not just your imagination. It is worse than normal.

The upshot of these poor job market conditions for job-hunters is:

  • Your job hunt will likely take longer, possibly double the amount of time you may have expected:
    • For experienced writers, that may mean 6-9 months of active job hunting. (Under normal conditions, I would expect job hunts to take 2-6 months at this level.)
    • For junior or entry-level writers, it could mean 7-12 months of active job hunting. (Under normal conditions, I would expect job hunts to take 6-9 months at this level.)
  • The squeeze for jobs will be felt most by junior technical writers, but it will also impact more senior technical writers:
    • Junior or entry-level technical writers will find it harder to find employers who are offering entry-level work and they will notice that the qualifications are more rigorous or demanding than normal.
    • Senior technical writers will find the competition is stronger. You may find you are now competing both across and up—competing across against people who are both at your level and competing up against people who are perhaps one level above you in your experience level and title. This increased competition is likely being caused by some candidates choosing to “shift down” the career ladder to cope with the lack of jobs at their expected experience level.
  • The normal churn of people leaving jobs won’t result in new job openings the way they normally do:
    • People who maybe are tired of their current job will be more likely to “grin and bear it,” choosing to remain in their current jobs longer because they may feel pessimistic about finding a better job.
    • Employers may choose not to back-fill roles when employees depart, preferring instead to do more with less.

Plan your finances accordingly. Your rainy day fund may need to stretch a bit more than normal.

😕 Okay, so it’s a tough market. What can I do about it?

With my talk about gloomy job market conditions out of the way, I’ll now share a couple of the lessons I learned in my most recent job hunt.

🤝 I can’t emphasize enough how important your network is

One of the most challenging aspects of my job hunt was that I couldn’t hunt out in the open and lean on my professional network for help finding opportunities. I’ve worked really hard to form meaningful, trusted connections throughout the technical writing and software industry, so it was especially difficult that I couldn’t openly tell people I was job hunting. Because I couldn’t tap into my network, I had to rely on mostly cold applications. That’s one of the potentially big reasons why my job hunt took as long as it did.

If you can be open about your job search, then I strongly recommend tapping into your social network as much as possible. I have almost always landed jobs in the past through people I knew. I initially found out about the job at Cribl through someone I had connected with when I ran the Write the Docs Quorum events in 2021. The connection helped me initially discover the job and get my foot in the door. I still had to be a good candidate beyond that initial connection, but even loose connections like those can help.

If you’re not used to a network-first method of job searching and don’t know how to use your professional network for job hunting, I recommend checking out The 2-Hour Job Search by Steve Dalton. It is a helpful guide for conducting a network-centric job hunt. Although it is a little geared toward recent college grads, it can easily be adapted to a seasoned worker’s job hunt.

I need to give one caveat, though: never treat your professional network of friends and colleagues as purely a means to an end. Yes, you should always form strong working collaborative friendships with potential future coworkers. But you should form these relationships because they will enrich your life for their own sake, not simply because they can help you get a job.

My main way of building my professional network is through contributing to open source at The Good Docs Project. I personally love to socialize with other people by working on meaningful tasks together. It helps me get to know people on a deeper, more collaborative level. Open source is a great way to build lasting friendships while skilling up at the same time.

Build your network in open source

These relationships will enrich your life and career for their own sake, but they have the added benefit of helping with your job hunt at times when you need it too.

🤖 The biggest change from when I last job hunted: ATS resume screeners

I found that one of the toughest parts of job hunting was getting past the new bouncer of the job hunting world: applicant tracking system (ATS) resume screeners. Recruiters use ATS software to scan your resume for keywords that determine how well you match the job description you applied for. I don’t fault employers for using ATS screeners, especially as a means of dealing with the tidal wave of applicants that every job gets these days. That being said, I personally think ATS resume screeners are perhaps overly aggressive at weeding out candidates and early scholarly research appears to back that up.

I’ll use myself as an example. At this point in my career, I have 10+ years of experience, a wealth of technical and industry knowledge, and deep connections in the technical writing world. I consider myself to be a fairly strong candidate. I also manually customize and adapt my resume and cover letter for every position I apply for to match what the job description says they are looking for. Even with all of that, I found that the vast majority of my applications were failing to get past ATS screeners.

I generally prefer to rely on my professional network to pole-vault over the resume-screening stage, but, as I said earlier, I couldn’t do that with this job hunt. So, I began running a lot of experiments to see how I could build better resumes that could get past ATS screeners.

Here’s what seemed to work:

  • Identify the keywords - Watch for the words that are repeated words continuously throughout the description. These keywords hint at the company’s requirements. You must have these keywords on your resume.
  • Use those keywords - Highlight the specific qualifications, skills, and certifications you have that match what the job description mentions. Use the same keywords the job description uses.
  • Mirror the same keyword organization as the job description - Different keywords are weighted differently. The order in which keywords appear in the job description reflects the importance of those keywords for that job. Prioritize your work history and display your work accomplishments in the same order as the requirements listed in the job description. Ensure the first few bullet points under each position are directly relevant to the job description. Focus on accomplishments and responsibilities that match what they’re looking for.
  • Don’t forget to proofread! - Checking for grammar is especially important for technical writers for obvious reasons.
  • It still needs to be human readable - It’s tough writing a resume to be read by both bots and humans, but if you get past the bot gatekeeper, the resume still needs to be able to communicate with a human. Now is a good time for me to also remind you that you should not keyword stuff or try to cheat by puting fake keywords in white print on your resume. ATS screeners can catch this behavior.

Failing that, the easiest path is to simply pay for ATS resume builders like Teal HQ. I used Teal HQ near the end of the job hunt to learn how to better customize my resume and it really helped. Jobscan is a similar tool that others recommend, but I haven’t used it and can’t speak to its quality personally.

These tools let you add all the possible line items (skills and bullet point phrases) that could go into your resume. Then, you upload a job description for a role you are applying for. The tools then coach you and offer advice for how to custom-build and improve your resume for that particular job. TealHQ helped me to manage the task of customizing my resume while simultaneously preventing me from introducing the kinds of little errors that I am sometimes prone to when I make constant line-item tweaks and edits.

It also provides additional tools to track the jobs you apply for, such as which stage you are at with each one. Having done that kind of tracking without tools before, I think that it helps manage the cognitive overload and administrative busy-work of job hunting.

⌚ Timing seems to matter

Another thing that helped me was to apply for jobs the same day they were posted. I also recommend using job search tools besides LinkedIn. For example, I was much more successful finding jobs on Otta than on LinkedIn.

Sometimes I would see an interesting job description while scanning at lunchtime. At the end of the day, even though I was tired from a full day of work, I would push myself to take an extra hour at the end of the day to apply. Taking the time to get an application in early seemed to help me get more callbacks.

✨ Investing in my portfolio site was definitely worth it!

I’m really glad that I spent 9 months building this portfolio site and improving my web development skills along the way. As I mentioned in my inaugural blog post, my primary goal in creating this portfolio site was to improve my Hugo skills, but the secondary goal was to help my job hunt.

By a lucky coincidence, the fact that this site is coded in Hugo was a big bonus for me in my job application with Cribl since their docs are built with Hugo. That was incredibly lucky and a big selling point in my favor! However, even if I were applying for a non-Hugo job, creating this site from scratch demonstrates that I have the solid technical skills that a technical writer needs to have.

I think my website mostly speaks for itself, so you can poke around my site to get a sense of what I recommend including in a portfolio site like this.

One thing I might call out is the success stories portion of my site because most portfolio sites don’t include a section like this. Even though it’s not a traditional feature of portfolio sites, I feel that building out my success stories helped give me an edge in my job hunt. The success stories on my site are the result of thinking deeply about what my dad (a retired human resources manager) calls PAR stories. PAR stands for Problem-Action-Result. Sometimes these stories are also called CAR (Challenge-Action-Result) or STAR (Situation-Task-Action-Result). I’ll use PAR here as an homage to my dad.

PAR stories are useful for talking about your accomplishments in job interviews. They help prove to a potential employer that you have the necessary skills and track record to perform the job. In the PAR story format, you talk about a relevant problem you needed to solve at your job. Then you explain the action you took and the positive benefit that came from it. These stories should take you no more than 2 minutes to tell in a job interview. Most job coaches recommend having a variety of 10-12 PAR stories you can tell in a job interview, with 5 of them being some that make you look especially great, which means you should try to bring some of them out in most interviews.

I used the success stories portion of my site as a way to brainstorm and record my own PAR stories. I didn’t always tell all of my stories in job interviews, but the process of brainstorming these stories helped give me an underlying confidence that I was a strong applicant.

Also, even though I don’t know that this is actually true, I found comfort in imagining that potential employers might possibly read these stories on their own if they were perusing my website in more detail.

That’s a good segue to talk about another important tip, which is to…

😎 Don’t stop believing!

If you need to put that Journey song on repeat right now, go ahead and do that.

The mental game is a big part of effective job hunting. You need to find ways to keep your confidence high and your spirits up, especially when facing rejection. It reminds me a lot of what it was like to go on dates when I was single: lots of emotional roller-coasters, over-analyzing how every date/interview went in excruciating detail, lots of hoping and wondering.

I had some rejections during my job hunt that really hurt and which threw me off my game for a few days. They made me doubt myself and my abilities. But I found ways to power through them. I can’t tell you how to get yourself into a good place mentally where you can believe in yourself because only you can do that. But if it helps, here’s some of the things I did to keep myself in a good place:

  • I took the criticism I got in job interviews and—instead of getting defensive about it—I tried to own it and see how I could improve. For example, after some brutal criticism of my writing samples, I improved those samples and swapped them out for better ones that showed my skills more effectively.
  • Sometimes after getting a bad rejection, I would take a piece of paper and write all of the fears and insecurities that a bad job interview made me feel on one side of the paper. Then, on the other side, I would write a statement reframing some of those fears into more positive, empowering statements. These reframed statements helped me to consider more positive angles or perspectives on the situation. For fun and to help myself let go, I would then go out in the backyard, burn the paper in a healing ritual, and move on with my life.
  • Kvetching with other job hunters about the awful market was very healing. I recommend finding a support group of other seekers if you can. (Open source, anyone?) One cohort of people I know who got laid off from the same company at the same time, so they decided to organize a daily job hunter stand-up with each other to commiserate and share tips.
  • Having a mantra can help. It’s cheesy, but when either of us is job hunting, my husband and I frequently say to each other: “You’re a gem and they would be wrong not to hire you.”

📒 Cover letters, interview questions, and thank you letters—OH MY!

Several months ago, one of my former coworkers recommended reading Steve Dalton’s The Job Closer for advice on crafting cover letters and preparing for interviews. I also recommend this book for job hunters. It helped me to know what to write and what to prepare for interviews. It also helped me better understand best practices for the other parts of the job hunting process, such as cover letters and thank you letters. These little details add up.

I followed that book’s advice for the “Tell Me About Yourself” (TMAY) question in interviews and wrote a 2-minute introduction to myself that incorporated several FIT statements (favorite-insight-transition) recommended by the book. I memorized this statement and practiced delivering it naturally several times. For Cribl, I only gave my TMAY statement one time to the recruiter, but it helped me leave such a powerful impression that the recruiter ended up being one of my biggest advocates for hiring me at the company.

I’m not going to put my entire TMAY statement here on my blog, but here’s a small sampling from it:

My favorite part about my current role has been developing strong relationships with my co-workers across the company, including obvious ones like product management, engineering, and UX. But also ones you kind of have to work for and be deliberate about cultivating such as sales engineering, professional services, support, and technical marketing.

I learned that I thrive as a super-connector who breaks down silos and brings people together to solve problems and, ultimately, to create great technical content. Because at the end of the day, I feel that technical writing is actually about your ability to collaborate and the quality of your relationships.

I also followed the book’s advice and sent a follow-up thank you letter to the recruiter the day I was supposed to hear back about the job decision. That action seemed to jump-start the final steps in getting me to the point of getting a job offer.

😅 Job interviews went better when I learned to stop worrying and just be myself

Over these past few years, I had some really brutal job interviews. Some were big gut punches to my ego and were difficult to recover from.

I learned that my best interviews were the ones where I stopped overthinking my responses and instead just tried to be my natural self. When I complained to my husband about how hard interviews were for me, he gave me great advice: “They’re easier when you just think of it as a conversation with a new person you’re meeting for the first time.” He was right about that.

📐 Contributing to open source definitely gave me an edge!

A recent survey by CNCF found that 79% of open source contributors say that contributing to open source has helped their career. This is 100% true for me too. I was asked directly about my leadership and contributions to The Good Docs Project in every single Cribl interview (and I did many rounds of interviews with them). For this role, Cribl was looking for strong evidence of my ability to collaborate, lead, and mentor others. They wanted someone with strong soft skills as much as they wanted technical skills and writing skills. My work at The Good Docs Project is how I demonstrated these soft skills in action.

As I said in a recent presentation, contributing to open source can help your career in many ways. It has helped me:

  • Improve my existing skills - I often deepen my existing skills or get additional practice with these skills in open source.
  • Develop new skills - One of the things I like about open source is that it gives me a chance to develop new skills that I am interested in developing. As a technical writer, if I were to suddenly jump in and start doing UX design work or product management work or marketing, I would probably get some weird looks from people and I might even get in trouble. But in open source, I get to do that kind of work all the time. I’ve had opportunities to do product management, to do user research and design, to write marketing copy, and even to be a human resource manager. That’s because when you work in open source, you often have to wear many hats and take on a variety of roles and responsibilities. You can begin to develop those skills based on what the project needs, which is something I personally really enjoy.
  • Take on leadership opportunities - Open source always benefits from people who are willing to step up and do the hard work of being a leader. Through open source, I’ve learned how to manage both small and large teams at scale in ways that I never would have done at work. It’s nice to also practice and develop leadership skills in a low-stakes, sandbox environment where I can make mistakes and that’s okay. The consequences for making a mistake are usually pretty small. So, I just learn from my mistakes and improve and get better for the next time I face a similar challenge.
  • Build my network and exchange best practices with expert practitioners in the field - Because of the years I’ve spent working in open source, I’ve built a strong professional network of people well beyond my immediate company. I get to regularly exchange ideas and best practices with professionals working for Google, Amazon, Microsoft, and other major companies. They make me a better technical writer and broaden my understanding of the tech industry in general.

It’s also just really nice to have an additional source of experiences to draw form in an interview. I always tried to answer questions using my official work experiences most of the time. But failing that, my open source experience was there as a back up for times when I didn’t have official work experience to draw from.

🌱 After you finally get a job, keep the next job hunt in the back of your mind

When you finally land your next job (and you will!), keep preparing yourself for the next job hunt by investing in good habits that will pay off over the long term:

  • Continue to build your professional network - As I said before, these relationships will enrich your life and career for their own sake, but they have the added benefit of helping with your job hunt at times when you need it too.
  • Pay it forward - If you were fortunate enough to get a job using your network, pay it forward by helping trusted, capable people in your professional network to land their next job. Make referrals and help them make connections when you’re aware of opportunities.
  • Record your success stories - When you have a big accomplishment or a big win at work, make sure you capture that! Also try to capture any metrics or quantitative proof of the accomplishment at the time it occurs.
  • Invest in your professional development - Always stay curious and hungry to learn. Look for ways to improve your skills by working on interesting projects that will help you grow and stretch beyond your current capacity. Creating a portfolio site or contributing to open source after work hours for a few hours a week is a great way to do that! You could also consider setting up coworker study groups for these purposes.
  • Put money in savings for the next rainy day - If you depleted your rainy day savings account while you were job hunting or if you never had one to start with, it’s time to start building your rainy day fund again. Start with a goal to get at least 1 month of savings to cover living expenses. When you meet that goal, throw a party to celebrate, but keep going. Next, get it to 3 months. If you can eventually get it up to 6 months, you will be well prepared for the next potential layoff.

😩 My parting thoughts about the hiring process

Okay, if you made it this far in my blog post: good job! This is the part of the blog that I’m not expecting everyone to make it to. If you’ll indulge me, for this final section of the blog, I am going to do some mild hand-wringing about how broken the entire job hunting process is. I want to lament about how the job hunting system actively works against its own stated goals of hiring good team members.

Let me begin my argument with a salient analogy. As you are likely aware, here in the U.S. we’re in the middle of an election year. I dislike election years immensely. They make me feel sad. One of the things that I feel sad about in election years is how I am constantly reminded that the set of skills it takes to win elections are completely different from the skills it takes to effectively govern and do the job of the office. There isn’t much overlap between these two skill sets and, in some cases, the skills may actually cancel out each other in highly counterproductive ways.

In that same vein, I feel frustrated that the skills required to get a job are entirely different from the skills it takes to do a job effectively. To illustrate my point, let me mention the book The Ideal Team Player by Patrick Lencioni, which I recently read to prepare for my previous blog entry. The book is about three important virtues that every ideal team play must have: being smart, hungry, and humble. Lencioni strongly emphasizes how important humility is:

People who are hungry and smart but lack humility are “skillful politicians.” These people are cleverly ambitious and willing to work extremely hard, but only as much as it will benefit them personally. Unfortunately, because they are so smart, skillful politicians are very adept at portraying themselves as being humble, making it hard for leaders to identify them and address their destructive behaviors. By the time the leader sees what’s going on, the politician may have already created a trail of destruction among their more humble colleagues who have been manipulated, discouraged, and scarred.

Frankly, we could all do with less self-oriented politicians at work and in our lives, right? We need people who are more collectivist and willing to put others ahead of their own egos and ambitions. But let’s face it: the current hiring process dis-incentivizes selecting employees who are humble. It only encourages being smart and hungry. It doesn’t in any way select for humility.

By its very nature, job hunting requires you to constantly sell yourself. While it’s good for people to advocate for themselves up to a point, it can be taken too far. It can change how you think about yourself and how you treat others. But our currently brutal, highly competitive hiring system practically encourages you to take it to that level of unhealthiness.

I am not a person who enjoys drawing attention to myself. I am not a person who enjoys talking about my accomplishments. I feel deeply uncomfortable at the idea of playing politics or choosing to work on high-profile projects purely for the visibility. Instead, I prefer quietly doing a good job that needs to be done in a way that I can be proud of. I like to give credit to other people and to my team as a whole, but I don’t like to receive solo credit by myself. I prefer quiet altruism. And, frankly, I actually really like that about myself.

But job hunting forces me to become something else. It forces me to build an egotistical portfolio site like this as a monument to my oh-so-great accomplishments. It takes stories of accomplishments that I genuinely cherish for intrinsic reasons and cheapens them by turning them into public displays of merit for extrinsic gain. It changes how I think about myself and how I present myself in ways that I feel deeply ambivalent about.

And it just kind of saddens me because, well, I guess there’s no other way for humble people to convince someone they’re worth hiring. So naturally humble people either have to learn how to play the game, to twist themselves into something they are not, or just give up trying. I can’t help but dream and wish and hope that there was another way.