Career job hunting

Cate’s Career Coaching Process (AKA A Process for Finding Your Next Job)

A young woman sits accross from an older woman who has a notebook. Both are wearing old fashioned dress. It looks like a job interview.
Credit: Flickr / Ethan

I know a number of people who have been laid off recently – the market is on a downturn and this is more common than seems to be being talked about. I’ve spent time helping a few people try and find their next thing lately, and after some iterations I now have a process.

1. What are you going towards?

Whether someone is leaving their job voluntarily or not, there’s a good chance it hasn’t been great for a while. This makes it easy to focus on what you don’t want rather than what you’re going towards. But you make better decisions when you focus on what you want rather than what you’re trying to avoid.

Be brutally honest – what do you really want to be doing? What do you want your life to look like? How do you want your job to fit into you life?

Only once you’ve done this, consider what tradeoffs you are prepared to make.

For me: I loved managing a distributed team, and I wanted to keep doing that if possible. But I knew there weren’t many of those kind of jobs, so I was realistic that I might have to compromise. There were two dimensions of compromise: on-site management, or remote IC (individual contributor) work. On-site IC wasn’t something I was going to consider until those options were ruled out.

If you’re helping someone else: It’s easy to think you know what someone wants (if you think you know them well), but don’t assume. Ask questions, make observations about what they seemed to enjoy and what their strengths are, but let them figure out what they are going towards. It’s great if you are surprised! This sometimes takes people a while (and multiple conversations), but it’s really worth the time because it’s the foundation of everything else. Once they’ve figured it out, don’t help them be “realistic” even if you think that it’s going to be hard to find what they want. It’s unlikely to be helpful. Most people who you actually want to help have no trouble being realistic.

2. Resume.

Honestly, I hate resumes. Even as a hiring manager, I take very little interest in them (I think resumes are mainly a bias vector). I don’t have one, I got my last 4 job offers without one, and when I did have one it was one I paid someone else to create for me. If that’s an option for you, I really recommend it and I’m happy to connect you to the person who did mine (tweet me – @catehstn).

Unfortunately most people still need resumes.

The main points with resumes:

  • Focus on what you achieved, not what you did.
  • Keep it short.
  • Make it readable. Use clear and concise language.
    • Prefer short paragraphs to long bullet points.
    • Use a service to check the reading age.

Once you’ve written up your experience, write your summary. The summary is two to three sentences that position you as a good person for the job you want, and should be backed up by the experience you have.

When you think you’re done, send it to three friends whose opinion on this is worth having. Ideally they review or at least see resumes for the kind of job you want. They might point out stuff you’ve missed. Try and find at least one native speaker of the language your resume is in.

If you’re helping someone else: This really depends on how much time you have. I don’t believe resume writing is a useful skill, so I’m happy to rewrite sections for someone. The process I followed was: I rewrite (or write) the section from their last job in discussion with them, they rewrite other jobs, and then I go through and edit those. Then, we write the summary together. If you’re just reviewing someone’s resume, focus on how they are coming across, or any information that appears to be missing, rather than how you personally would write a resume.

3. “Soft” interview questions.


The purpose of these interviews is normally to get a sense of your experience, personality, and ways of working. When you wrote the summary for your resume, you made a conscious effort to think about how you want to present yourself. You want this to come out in your answers. This means not just answering the question, but deciding what you want the takeaway from your answer to be – something that supports your summary – and then telling a story that showcases that. This means that the same story can be an appropriate answer to multiple questions, depending on what you highlight.

The more open ended the question, the more scope you have for this. For example the question “tell me a bit about your background?” You can answer this question directly and chronologically (“I went to university at XXX and then I worked at YYY and did ZZZ and then…”) or you can frame the interview with your answer.

When I get asked this question, I say something like: “I’ve spent my whole career working on mobile, including writing a J2ME app a long time ago! At Google, I built most of the first generations presentations experience on iOS and ran a team building a location-based B2B app, and also worked on that app on Android. Most recently, I ran the mobile team at Ride.”

When answering these questions, one thing to keep in mind is that stories about dysfunctional environments are not helpful. For example a question like, “tell me about something you worked on that failed?” The answer that most springs to mind might be the one where the business didn’t know what they wanted, asked for unreasonable things, didn’t listen to engineering, and of course it didn’t ship or what eventually shipped was something that people didn’t want. If you don’t have a better lesson from this than “don’t work in that kind of environment” (a very fair lesson to learn from that experience), it’s not a good story to share. A less epic failure with more concrete takeaways is a better option.

If you’re helping someone else: Don’t just consider if the answer seems good, consider if it relates to their summary. If you’ve worked with them or know them well, point out other stories or achievements they might have missed – people are often a little blinded to their strengths, because they come more easily.

3b. Recommendation.

If I’m writing (or likely to write) someone a recommendation, I write it after we’ve done this together – it’s when their achievements are top of my mind, and I can write something that a) supports their summary and b) highlights some stories they might want to talk about in an interview.

If you’re asking for a recommendation: Make it easier on your recommender, and highlight some bigger achievements that you think they can speak to. These should relate to your summary. E.g. if your summary highlights your love of experimenting with new technology, include that experimental project you did that influenced something in a useful way.

4. Technical interview preparation.


When I give someone a mock technical interview, I give them my standard technical interview but I am less nice. Mainly, I do less time management for them – allowing them to spend too much time in places that aren’t helpful, if that’s their inclination.

I think Time Management is the easiest and most overlooked skill of technical interviewing. When people don’t know the answer they are very tempted to spend a bunch of time on peripheral things like validation, or writing a bunch of different function definitions, or setting up an elaborate test suite. Sometimes they start writing a brute-force solution with the goal of better understanding, but this takes up a more time than it provides utility. All of these might be good and useful things to spend time on in Real Life Programming, but can work against you when you are trying to show your capabilities in 45 minutes to an hour.

Other common mistakes:

  • Not taking the time to think of more than one option for solving the problem.
  • Not communicating clearly, meaning the interviewer has to guess what you are doing.
    • It’s easier to give someone feedback and guidance when you understand how they are thinking, what they are doing, and why.

5. Introductions.

Some people spread a broad net, my preference is to speak to a few places that I have strong introductions into. It’s more likely to be a good fit, and I’m more likely to be successful in the process. When I was looking for a job in August / September, I spoke to four places with strong connections and ended up with two offers that I felt great about. This is my preference with introductions – to introduce people to places where I think they have a good chance of success, and where I think they would be happy. I use a customised version of the recommendation I wrote to introduce people.


I estimate that taking people through this process took ~8 hours per person (and these were people I knew well). As a result it’s not something that I would make time for other than for close friends or people I have a professional commitment to. They probably spent at least that, more, working on parts of it by themselves – technical interviews especially are a lot of work to prepare for.


Job hunting is a PITA and a ton of work. It helps to think about how to be effective at it.

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