9 mins

Does starting a job search fill you with fear? Have you taken roles in the past that you’ve regretted?

April 13 – June 22, 2021 Event series
graphic element

Tell your team: LeadDev Together is back!

A six part event series addressing engineering leadership's most fundamental challenges.

When a recruiter or interviewer asks you the question – ‘What are you looking for?’ – do you draw a blank?

I’ve been working long enough to have been through dozens of job interview loops myself. While I think I am pretty good at the process, I have still found myself not ready to answer the ‘What do you want from your next role?’ question.

I’ve also been a hiring manager long enough to have performed hundreds of interviews and seen all levels of answers to similar questions.

I completed a new job search in October 2020. Based on my interviews and job decisions in the past, and some frightening moments in my early interviews, I decided to take a more formal approach this time. I often talk and write about being deliberate and thoughtful in your decisions as a leader, so I thought it would be good to take my own advice.

I created the following process to help me in my job search:

  • Identify the things that were important to me in a job;
  • Prioritize the criteria that I identified;
  • Figure out how I could evaluate a potential job against my prioritized criteria.

Identifying what was important

To make my list of criteria, I used Miro and listed anything I could think of that I thought was important in a job. Each idea went on a separate card (real cards would work just fine too). It might be tempting to write them down on a piece of paper, but you will need to reorganize them and group them. I would definitely recommend cards or sticky notes (or their virtual equivalent) for this process.

After my brainstorm, I had something that looked like this:

The vertical and horizontal ordering didn’t have any specific meaning beyond a primitive, affinity-grouping exercise as I created the cards. I am sharing mine with you, but you should figure out your own criteria since it is very personal.


My next step was to sort each criterion based on how important it feels to me. After sorting, my cards looked like this:

Things in the same row were close in priority. I also sorted cards left to right.

Then I did a bit of color-coding to help me understand the ‘big picture’ themes for myself.

Now I had some useful information about myself and what I wanted. Some things were surprising to me. Some things I had thought were essential weren’t nearly as much of a priority when forcibly rated against others.

I learned that the company culture and mission are the most important things to me (pink), followed by my role responsibilities (green), compensation/benefits (bright blue), co-workers (pale yellow), the product (pale blue), company stage (turquoise), and finally the tech stack (mustard).

Enter the spreadsheet

At this point, I realized that given my new strict prioritization, I could rate an opportunity against these criteria in a more objective way.

I exported my notes from Miro into a CSV file and loaded them into Excel. For each criterion, I added a quick explanation (so I would understand what I meant when I looked at it later), I decided if it was a ‘must-have’, and I assigned a score in decreasing order based on the ranking that I had done. For each criterion, there was a simple Yes or No answer. Forcing this explicit decision requires you to make a choice instead of giving partial credit.

Each criterion can have a negative, zero, or positive score. The score is negative if the criterion is a must-have, but the role does not meet it. The score is zero if the criterion is not a must-have, and the role does not meet it. The score is positive if the criterion is met by the role. Note that not all the ‘must-haves’ are the top priorities!

I made the total of the scores 2000 because that is a nice round number. Maintaining a target total forced me to decrease some scores if I wanted to raise others, which was another definitive decision.

I then went through my past few jobs and used the spreadsheet to compare them against the criteria. This process wasn’t going to be completely objective. Rating a job I was in eight years ago against my current standards wasn’t going to be a completely effective measure of the role. But it did let me do some ‘sense checking’ against my criteria, and forced me to think a bit harder about some of them which resulted in adjusting the scores slightly. After that exercise, I could look at each job’s score to see if it seemed right, given my experience. While none of them were perfect, they each felt ‘close enough’ to a point where I was reasonably happy with the scoring.

Rating my previous roles against my current criteria also allowed me to look across them to find patterns and give me more insights about myself.

It was interesting to note that while my excitement about the product is central, I have only been excited about three of the last five products I’ve worked on before I started the job. While having a good technology challenge is vital, I similarly only felt that about three of my last five roles. I learned that while each of those things is important, other factors can make up for its lack. I also do know that I am quite good at finding things about a product that can make me excited, so that isn’t as much of a concern to me as it would seem.

Creating interview questions

For each of my criteria, I created a set of sample questions that I could use to help me evaluate a job. Given that my initial list of criteria was 39 items long, the list of questions ended up spanning five pages. I did not expect answers for all of these questions from an interviewer. The questions were prompts to help me think of ways to evaluate the company in an interview situation. I knew that if I did my due diligence in the interview process, I could answer any one of those questions for the company.

The process was analogous to building interview questions for hiring someone in a company. You start with your company values or career ladder benchmarks and use them to generate questions for a candidate. My tenets list came from my prioritization exercise, and now I was developing the queries I needed to answer so that I could figure out how to score the role against them.

As I interviewed with different companies, I had the question prompts in front of me. If you have ever been in an interview, and the interviewer asks you, ‘Do you have any questions for me?’ and you can’t think of anything immediately, having five pages of questions in your eye line is very helpful!

As I went through the interview processes, I reviewed my notes for each company to decide how comfortable I was rating them against my criteria. In some cases, I requested a couple of extra conversations to make sure I had a minimum confidence level.

Making a decision

Once I got to an offer stage, having my ratings was valuable in evaluating the specific offer and deciding if I wanted to extend the process to get to the offer stage with one of the other companies I was interviewing with. While there were a few companies I was excited about, my ratings made it clear that one company was the best fit for me. When we negotiated an offer I was happy with, I could confidently accept it.

Doing this yourself

If this process seems like something you would want to employ, I can recommend it, but it is worth understanding the limitations.

This process gave me a sense of objectivity, but it is still a subjective process.

My feelings about my past jobs are all colored by my experiences working at them for years. If I had used this process when I interviewed, would I have predicted how the role would have turned out accurately? Probably not, although I might have paid more attention to specific areas in the interview process. If I ever leave my new job, it will be worth doing this exercise again for the company to see how my feelings changed over my tenure.

My ability to judge an opportunity against 39 different criteria during an interview round of some hours will always be suspect. There will always be some amount of bias introduced based on my experience during the interview process itself.

You have to be very careful when creating your list of criteria not to fall victim to social desirability bias. Are the items in the list things you care about or something you think you should care about? The prioritization process can help with this, but it is still an easy trap to fall into.

My evaluation of my past roles showed that my favorite jobs only satisfied around 80% of my criteria. This result seemed a bit off (even adjusting for the ‘what I want now’ vs. the ‘what I wanted then’ bias). The roles I was least happy with were both less than 60% of a match. While the percentage matches weren’t perfect in absolute numbers, they were different enough in relative numbers for me to be comfortable with my criterion. I rescanned my priorities to see if it was a result of social desirability bias. Still, I think it was my criterion evolving based on my experiences.

While there are some limitations to the objectivity of the process, I found the act of building my criteria, generating questions based on them, and evaluating my past roles to be extremely valuable. It made me think about what I want at this stage of my career, and what I appreciated and disliked about my former positions. This exercise helped me be much more self-aware when talking to recruiters and people at each company.

Thanks to this process, I was able to cut short interview loops when it became apparent that the job wouldn’t meet my criteria. I was able to say no to jobs that I might have otherwise interviewed for in the past. When I found the right role for me, I was able to accept it without any fear of missing out on some other position.

While you may not want to create such a formal process as I did when looking for a new role, if you take one thing away from this article, let it be that it is worth spending some time to think through your past positions, where you want to go in your career, and what is important to you in a job. Having that level of self-awareness in an interview process will give you a better sense of the questions you are trying to answer and a higher confidence level when you interview.

Best of luck in your search!