Job Hunting Tips for Nonlinear Careers

I originally wrote this post while job hunting in 2018. I knew I needed a change from the work I was doing, and I developed a tool (read: spreadsheet) that helped reinforce a few lessons from the process.

You can make a copy of it over here. I hope it helps you out. If knowing your not along helps, here’s some of my story.

The difficulty of job timelines and titles

One of the toughest parts of job hunting is the timeline. It can easily take a month to interview with a company worth joining in a mid- to senior role. It can take 1-2 months before that to network your way to getting the interview (more on that later). Slower HR processes add another 1-2 months and more when the timing is unlucky. If you’re unexpectedly leaving a job and don’t have a runway of savings, it can lead to stress that makes the whole experience blur into a sense of panic.

What’s even more difficult can be understanding what particular job title to pursue. Job titles are changing or evolving constantly. There are lucrative opportunities with titles like Developer Advocate or SRE that you may want to give a try, but you’re not sure you’ll hear back. It’s great to give it a try, but getting rejected can make the entire job hunting experience feel like a failure.

Numbers are our friends when panic wants to set in.

I found a pattern of job hunting that helped me get out of that train of thought, and it’s since helped a handful of people I’ve mentored. I’m hoping it (or whatever version of it you help make) can help others.

Step 1, prioritize your why and your what

I have a nonlinear career path, with time in support, engineering, marketing, and a little sales. Over the years, I’ve focused on exciting roles at companies I believe in more than a given title I’m looking to perfect. I’m not saying that’s the best strategy, but it’s been mine to date.

So when I was let go by my last gig, I knew my startup itch was scratched for a while. Startups, in my three tries and ~5 years of experience, have been a lesson on the importance of revenue. It’s the master all venture-seeking companies serve, and it’s ultimately the only thing that matters unless you’re making a lot of it already. I’m good with taking a breather from that rat race while I make up for lost 401k contributions and a work/life balance that left me disappointed in my priorities of late. That leads to my why: I’m interested in working for a mature organization, which gives me space to have focused learning that will refine my core skill set while spending more time outside of work.

Knowing that I am leaning toward larger organizations, the question is doing what. A specific title is something I have intentionally avoided in order to continue to round out my knowledge of running an enterprise b2b business. I’m not a certain job title for life; my identity tends toward evolutionary on that front. Others enjoy the deep expertise you get from being a certain job type continually. I respect both, and know myself. I’m still exploring. Rounding out my skills is part of my why.

Knowing that, the what remains. I’ve been involved in much of the Developer Relations backchannels since the DevRel Collective started. It’s great to see DevRel being more of a standard role, but there are few products I have a passion for representing at the moment. But a funny fact remains: I realized I love to study DevRel and facilitate its successful execution more than I enjoy doing it. As I zone in on my what, I keep getting back to two questions:

  • How does open source become more sustainable for maintainers? And,
  • How does someone in a community organization quantify their value to a company?

That’s (part of) my what: I want to build systems for maintainers or Community professionals to be valued more, especially in the open source world. To me, that means I want a systems thinking-oriented role, one where I have space to create lasting communities. That tells me I want to seek a Program or Product management role. Secondarily, I would do any work that gives me time to dig deeper into either while advocating for their standardization. (Spoiler alert from 2020: I did with my role at Opensource.com.)

I will be honest and say it took me two months into unemployment to commit to saying no to opportunities that didn’t align with my why and my what. Before then, I had a vague sense of dread about even the most exciting opportunities. I knew I wanted a job, but I hadn’t found what I wanted to do again. After I knew my what and why, I felt better about the choice.

Step 2, get your team together

In 2008, almost exactly 10 years ago, I was unemployed like I am today. I had graduated with a CS degree from a decent college, but I couldn’t land a job anywhere. I had filled out 90 applicants in the weeks up to graduation, and I heard back from only one of them. Not even an Apple Store wanted me to interview. That’s about a 1% response rate. I was ready to give up when I happened to mention my unemployment on Facebook. A college acquaintance responded to the post asking if I’d be willing to move to Boston. I had applied to jobs in 12 different cities, so what’s one more? Sure. He referred me, and I got a call that day. The referral was magic, netting me a 100% hit rate. I was stunned that after months of hearing nothing back that I got such an immediate response.

Fast forward to today, and not a lot has changed on this front. References are everything to getting a callback, and I every job I’ve gotten was due to a referral. Even this time around, I applied to a competitive role at a top-tier company and heard nothing back for 3 weeks. Then I got to know someone who worked through, out of dumb luck, and she helped me get noticed. That’s nearly a month without a word and then bam: immediate response.

At this stage in my life, the response rate is close to 90% for referrals, and non-referral applications are closer to 10%. So the next step is this: tell people you’re looking. If you took the time to work through step 1, you have something to say to them. And if you think you have no one to tell, look again. There are a lot of people who are willing to help when you ask nicely. If you’re looking for examples on doing it well, check out this one or this one.

Step 3, know how to pitch

You asked for help, privately or publicly, and now have a chance to talk to a potential employer. How are you going to get the job? I always ask myself, “how have you proven you’re qualified? How have you prepared?”

When it comes to qualification, I let a spreadsheet show me the way. The simplest model I’ve found is to add each requirement into a line and see how you line up.

My “Job Preparedness” spreadsheet. Copy each qualification into a spreadshseet, then add a check and a story.

When it comes to years of experience in a particular type of role, I remember to push myself to find the best story to tell. For instance, my last Developer Advocacy role included everything from managing Agile-style product management to defining a brand and go-to-market strategy. I like to take the time to frame a job appropriately on my resume. If I’m still short on years of experience, I still apply. If it says 5-8 years experience and I have 4, I let them say no instead of me saying no. These are often near-meaningless numbers made up by copy/paste job descriptions.

I also prepare. It’s a double-edged sword sometimes, but I have this quote from the not-as-short-as-legend-tells-us Napoleon Bonaparte deep inside my headspace:

“If I always appear prepared, it is because before entering an undertaking, I have meditated long and have foreseen what might occur. It is not genius where reveals to me suddenly and secretly what I should do in circumstances unexpected by others; it is thought and preparation.”

Here’s my routine for any job I make it this far through the application process:

  • Read a book on the subject that I will be focusing on. For a Product Management role, I picked up Inspired by Marty Cagan. More data-focused? I cruised through Lean Analytics. Blockchain came up for a little while, so I read Attack of the 50 Foot Blockchain (then backed away slowly from that idea).
    • Why take the time? If I’m not willing to read a book on the subject, I definitely don’t want to do the work for the next stage of my life.
  • Imagine I got the job. Now what? I tend to do two things for this one: write a blog post about what my job means to me. I also write out however many goals come to mind. My preferred format has been OKRs and I toss them in an Evernote or gist. Both of these solidify a significant part of what I want to communicate in the interviews.
  • Plan to be an active interviewer. See how you can guide the interview process as opposed to letting it happen to you. Part of the interview is how you handle the interview process. Guiding it forward while not being overbearing is a great example of how I lead. For example, I have frequently sent my OKRs to the hiring manager as a way of starting a discussion on whether we’re on the same page. I’ve been told it’s helped me get the job offer.

If I’ve done all these parts, I go in confident that I can accurately represent myself in a way I can be proud of. And that often means a decent interview process.

So you didn’t get the job

If we take the worst case next, let’s say I followed these tips and don’t hear a thing back. What do I do? First off, I fight the urge to throw my hands up and assume it taught me nothing. Not hearing back sucks, and it doesn’t give me anything I know I should work on next time. But it does give me some data: I didn’t get the job. The questions I ask next are:

  • Are there external variables? These can be location requirements that I don’t fit, company news that affects hiring, stock market news that causes a hiring freeze—anything I can glean from what’s visible in my network.
  • How far did I get? If no one responds to my resume, then it either is not useful or is great but for a different job. If I got a phone screen but no interview, then I probably said something offputting and should practice with my friends. If I made it through interviews and didn’t get a role, it tells me more about my interviewing than it does my resume. Breaking down the phases here helps you know what’s off and what’s something else. That’s why I made this spreadsheet for you to enjoy.
  • Was I qualified? If it is too great of a delta between my resume and the job description, then I may be barking up the wrong tree. Or if someone you know got it, you can figure out what qualifications mattered more than the ones you offered (read: I didn’t say “have,” because it’s what you presented, not what you have).
  • Have I shown that I’m qualified? For the type of work I do, it’s worth taking the time to write blog posts, produce podcasts, or share code that is fresh and related to the work I want to get. If I haven’t done this for more than a month, I assume it impacts my job chances.

You got this

Me climbing out in Wyoming.

I occasionally rock climb. A friend of mine always says “you got this” when I try a challenging route. If I follow up with “I probably don’t,” he always wins the discussion with “try your best.” I have to say, I eventually figure it out the more I try. As tongue-in-cheek as his one-liners are, they’re right.

So when you’re deep on the job hunt, imagine me saying “you got this.” When you protest, think of me saying “try your best.”

If you can look at a rejection and tell yourself that you tried your best, you can hold onto it until you get to a yes.

Let me know if any of this is helpful to you on Twitter, @mbbroberg. If you’re curious about what job titles you should consider, the archive of my old podcast, The Geek Whisperers is full of good ones.