Taking A Thoughtful Approach To The Job Search Process
Привiт, свiте! (Hello World in Ukranian)
Thanks again to all who have purchased the book. If you have enjoyed it, please tell your friends about it and review it wherever you bought it! I saw it on the shelf in my local bookstore last week, and it blew my mind. The people at the register said someone had ordered it, so they got an extra copy. If you’re my neighbor, let’s get coffee!
If you haven’t bought the book yet and are getting value from this newsletter, please consider it! It’s available from Amazon.com, Bookshop.org, Barnes & Noble, Audible, and your local bookshop! I collect all the links to stores I find at https://itdependsbook.net/
About this newsletter
If you are new to this newsletter, I’ll explain. Every two weeks, I release a chapter from my book It Depends: Writing on Technology Leadership 2012-2022, released by Unit Circle Press last month. I release the chapters out of order from the book, but each stands on its own. There is also a podcast serializing the audiobook in order.
The Latest Podcast
The latest episode of the podcast features a short chapter and a longer one from the audiobook: “How I Get My Focused Work Done” and “The Known Unknowns.” You can get it at Apple Podcasts, Spotify, YouTube, directly via the RSS Feed, or wherever you get your podcasts.
Drop me a line
If you have questions, want a signed copy (I'm expecting some new hardcover copies very soon, as I sent out all my last batch), or want to say hi, you can drop me a line at contact@itdependsbook.net. You can also leave comments on Substack or the various podcast places, but I may miss those.
Upcoming talk
I’m giving a talk, “The path from Director to CTO: How to follow it, or how to mentor it,” at the LeadingEng conference in New York City in September. More information and registration: https://leaddev.com/leadingeng-new-york
About this week’s chapter
I talk and write a lot about being deliberate in your decision-making as a leader. A few years ago, I was looking for a new role. I spoke to recruiters, headhunters, and friends at other companies and started taking calls. I quickly realized that I wasn’t following my own advice. I was talking to companies in different industries at different stages of growth… I wasn’t sure what I was looking for. I hadn’t thought my process through. I decided to create a very structured process to help me understand what was important to me and to help me ask better questions in interviews. I documented the process that I created and shared it in this article.
Do I think you need a process like this? Well, it depends 😊. If you are in the process of looking for a new job and find yourself struggling to answer broad questions from interviewers like “What are you looking for in a company?” or can’t think of questions to ask prospective employers, spending some time introspecting on what you want would be helpful even if you are in a position where you don’t have the luxury of time or choice in your job search process. Understanding yourself better can help you adapt how you approach a company that you may not be as excited about.
This chapter from the audiobook has already appeared on the podcast, in case you would prefer to listen to it or if you want more background information (of course, you don’t get the pictures): Apple Podcasts, Spotify, YouTube, podcast.itdependsbook.net
Taking a thoughtful approach to the job search process
Originally published on November 2, 2020
Does starting a job search fill you with fear? Have you taken roles in the past that you’ve regretted?
When a recruiter or interviewer asks, ‘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. 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 past interviews and previous job decisions, 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 my decisions as a leader, so I thought I should 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 position against my prioritized criteria.
Identifying what was important
To make my list of criteria, I used a digital whiteboard tool and listed anything I thought was important in a job to me. Each idea went on a separate card (real cards would work fine too). Writing them down on paper might be tempting, but you must reorganize and group them. I would absolutely recommend cards or sticky notes (or their virtual equivalent) for this process.
After my brainstorming, I had something that looked like this:
Figure 11 - My role criteria
The vertical and horizontal ordering had no specific meaning beyond a primitive affinity-grouping exercise28 as I created the cards. I am sharing mine with you, but you should figure out your criteria since it is very personal.
Prioritizing
My next step was to sort each criterion based on how important it felt to me. After sorting, my cards looked like this:
Figure 12 - My prioritized criteria
Things in the same row were close in priority. I also sorted cards from left to right.
Then I color-coded them to help me understand the ‘big picture’ themes.
Figure 13 - Color-coded priorities
Now I had some helpful 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. After culture and mission are my role responsibilities, compensation/benefits, co-workers, the product, company stage, and finally, the tech stack.
Enter the spreadsheet
At this point, I realized that given my new strict prioritization, I could rate an opportunity against these criteria more objectively.
I exported my notes into a CSV file and loaded them into a spreadsheet. For each criterion, I added a quick explanation (so I would understand what I meant when I looked at it later). Then, I decided if it was a ‘must-have,’ and I assigned a score in decreasing order based on the ranking I had done. For each criterion, there was a simple Yes or No answer. Forcing a definitive 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 principle 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 position does not meet it. The score is positive if the role meets the principle. Note that not all the ‘must-haves’ are the top priorities!
Figure 14 - Criteria in a spreadsheet
I made the total of the scores 2000 because that is a nice round number. Additionally, maintaining a target total forced me to decrease some scores if I wanted to raise others, another definitive decision.
I then reviewed my past few jobs and used the spreadsheet to compare them against the criteria. This process wasn’t going to be completely objective. For example, rating a job I was in eight years ago against my current standards wouldn’t be a completely effective measure of the role. But it let me do some ‘sense checking’ against my criteria and forced me to think a bit harder about some of them, which slightly adjusted the scores. After that exercise, I could look at each job’s score to see if it seemed fitting, 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 worked on before I started the job. While having a good technology challenge is vital, I similarly only felt that in about three of my last five roles. I learned that while each is important, other factors can compensate for its lack. I also know that I am quite good at finding things about a product that can excite me, 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 to all of these questions from an interviewer. Instead, 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 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 ensure 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 confidently accepted it.
Doing this yourself
If this process seems like something you 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 subjective.
My feelings about my past jobs are all colored by my experiences working at them for years. Had I used this process when I interviewed, would I have predicted how the role would have turned out accurately? Probably not, although I might have focused more on 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 criteria during an interview round of some hours will always be suspect. In addition, there will always be some bias based on my experience during the interview process.
You must be very careful when creating your list of criteria not to fall victim to social desirability bias. For example, 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.
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). I was least happy with the roles that were 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 they resulted from 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 building my criteria, generating questions based on them, and evaluating my past roles extremely valuable. It made me think about what I wanted at this career stage and what I appreciated and disliked about my former positions. In addition, 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 could say no to jobs that I might have otherwise interviewed for in the past. When I found the proper role for me, I accepted it without fear of missing out on another position.
While you may not want to create as formal of a process as I did when looking for a new role, if you take one thing away from this chapter, 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 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.
Thanks again for reading! If you find it helpful, please share it with your friends.