Career in Tech

How I Decide On A Job Role

Last week I accepted a role at Databricks. I wanted to write about why I made that decision (like I previously wrote about my decision to accept a role at Google), but I realized it is impossible to discuss that decision completely in a vacuum. Every decision represents passing by some other opportunity, and in this case, the other opportunity was Google.

With that in mind, before I write about my decision to join Databricks, I’ve decided to take this as a chance to explain a bit more about how I make career decisions. I think this post help provide context for that post while also serving its own purpose as a valuable look inside how one particular (and peculiar) person thinks about this type of decision.

Ready for some spreadsheets?

My Job Rubric

If you’ve stumbled upon any of my blog posts previously, you might have picked up on the fact that I’m a bit of a nerd. I like spreadsheets and charts. So, expectedly, my decision process involves a rubric that I have setup in a Google Spreadsheet. The exciting thing about it being in a Google Sheet, is that means I can share it, so here, for your viewing pleasure is a sharable version of my rubric, complete with some semi-real data (I’m not going to share my actual live spreadsheet for various reasons that should be fairly obvious).

What you’ll see in that link is a list of factors that I have found to be important in my enjoyment of a job. At a high level, all I do is go through the factors, score each one for all of my available options, and then pick the job with the highest score. Simple.

In reality, there is a lot of internal debate and guessing. At best it forces me to be really honest with myself about what is important to me and how that compares to other options I have available to me. At worst, I’m making a very important decision based off of lightly-educated guesses.

The Three Big Categories

I’ve divided the rubric up into three general sections, mainly to help digest it. Those sections are; connection with work, lifestyle and future considerations.

  1. Connection with work is all about how much I enjoy the actual day to day work, the people I work with, the topic, etc.
  2. Lifestyle measures what my life will be like at the work location, on my way to it, on my way home from it and when I’m away from it
  3. Future considerations considers how this role will benefit future Greg – will it open other doors for me or enable me to achieve some other goal?

Most of the time, when I make a job decision, I am selecting between two or three options that have strengths and weaknesses in different sections. This makes some sense, because if a job were stronger than another in every section, it really wouldn’t be a decision that required thought. So as I undertake this exercise I always remind myself that it is possible to optimize for any one of these sections at the cost of the others but it is not possible to expect any role to score perfectly at all of them. Most of what I am trying to do in my evaluation is to understand where there are trade offs and to decide if those trade offs align with my current life goals.

Factors and Weights

Within each of those high level sections there are a few factors that I rate on a scale of negative one to positive one. You could use a different rating system and get the same result, but this is the one I use. On the tab titled ‘Factors and Weights’ I’ve filled out some notes that help describe the various scores for each factor, so that my evaluation is consistent.

For example, on the factor of travel I’ve recorded the following:

  • Negative one: 15-30 days
  • Zero: 6-15 days per year, some multi-day trips
  • One: up to 6 days per year, only day trips

So this means my ideal role has a low amount of travel and the more travel that is required, the lower a score I would give it. A role that required me to be away for most of the year (for example a conference speaker) would currently rate very low for me. It might even get a veto, which I reserve for something so bad that this one factor itself could invalidate the entire job.

Each of those factors then has a weight associated with it. Some factors matter a lot more to me than others when making a decision. For example, free snacks are nice, but there is no amount of chips that can make up for having to work with screaming jerks all day. Having weights is a nice way to reduce my bias when deciding. Many companies offer free food, which sounds great, but by weighting that factor it helps me remember that more money might actually be more valuable, since there is some amount of money with which I could buy even better food and still have some money left over.

Over the course of my career and in conjunction with my life changing, the weights have changed. I suspect they will continue to do so periodically. For this reason, I tend to look at this rubric every year or so and adjust things. Sometimes that means a job that hasn’t changed, moves up or down in my ranking because of changes in my preferences. I think this is natural and healthy. I also learn more over time that causes me to adjust my weights – either through my experience or after having conversations with others that exposes me to new ideas.

It really doesn’t matter too much how you assign weights, so long as there is a somewhat consistent ratio between things. To assign the weights originally, I used an intermediate item of value ($10k in theoretical cash) to compare different factors – that helped me make sure I was weighing the $10k 401k match the same as about $10k worth of food.  Over time I’ve settled on a range of weights where I can just sort of adjust each thing up and down and the math all works out.

What Are the Most Important Factors for Me?

So what are the factors that matter the most to me? While yours might be different, I figured I’d take a second to call out a few that are important to me and why I’ve found them to be so important.

  • Location – as in where I have to live. Being in tech and post-COVID, fewer jobs require moving, but if a job did, this would be a big factor as that impacts the lives of my whole family.
  • Hours per week on average – Time is our most limited resource and I constantly try to optimize it, so it should be no surprise that this is high on my list. One thing I’ll clarify is that this is my estimate of how much time it will actually take for me to do my job well, not what anyone else tells me.
  • Coworker competency & helpfulness – as a Product Manager, my job is very collaborative and I’ve found the people I work with make a huge difference on how much I enjoy the work, which is why this factor weighs so high.
  • Believe in the leadership & company – at the end of the day I need to know what the work I am doing is accomplishing and who is directing that. I am not someone that can just push a rock up a mountain happily if that is what I’m told to do.
  • Stress level – I’ve found stress from work to be one of the biggest ways (second to time) that my work impacts my non-work self. Funny enough, for me personally, zero stress is not optimal. I like enough that it forces me to work hard and engage, but not so much that it causes problems in my life. I get bored when there is no stress and then everyone has problems.
  • Manager Relationship – While coworkers as a whole weight higher than my manager on the scale, the manager is the person who carries the most weight for a single individual. What can be so tough about this one though is it can change without much notice and when selecting a new job it is often being ranked off of 1 hour or less on conversations.
  • Availability of increased responsibility & growth – I tend to want to take on more, so knowing that is available is really important to me. (See note above about getting bored and the problems that causes)
  • Flexibility in the future – This is more about the ability to change teams, change offices, etc. I have found I tend to need a slight change in jobs or responsibilities every 2-3 years, and so like with the growth factor, I look to see if that is available. You could argue that this shouldn’t be important, since you could always change jobs, but I’ve found that changing within companies is exponentially simpler than changing companies, which is why it is beneficial for a company to offer flexibility. Google is top tier at this factor.
  • Importance to company priorities – is the project I am working on important to the company? I’ve found that when the project is somewhere between 3-7 on the company’s priority list, I have the most success. The #1 spot has too many cooks in the kitchen. The #8+ spots don’t get enough attention. The sweet spot is near the front but not in it.
  • Mentorship – I learn a lot the hard way, by doing, but I also really appreciate the ability to learn from people that know a bit more than me. Mentorship is possible outside of a company, but I’ve found that folks in a company have a bit more a reason to be invested in your success and working together is a great way to build trust. For this reason I always look around to see if there are potential mentors at a company.
  • Cash saved – I look at cash saved rather than salary. If I’m going to live in the same place, that doesn’t matter as much, but if I’m comparing jobs that require relocation, it is important to think about how different costs of living, tax rates, etc. impact the money I am putting away for retirement.
  • Commute – This used to be a really important factor to me but I recently reduced the weight given that I’ve been working from home for a few years. It will likely be more important for me in the future and is likely really important for other people, so I’m including it here. The way I see it, if I’m going to have an extra 5-10 hours taken away from my life, I’d rather they be productive hours where I’m getting work done, sitting in traffic doesn’t help anyone.

If you look back on my blog post about why I decided to join Google a few years ago, you’ll notice many of those factors above are mentioned in that post. That wasn’t a coincidence. As I considered the role, I used the rubric to guide my thinking and so when I wrote that blog post, those ideas were top of mind.

What Factors Aren’t as Important for Me?

Over time I’ve added a few things to the rubric that I still think it is important to keep in mind, but which don’t play as much of a factor in my decision.

  • My skill level at work – I used to look at this more when I was deciding between dramatically different jobs. Lately I’ve narrowed in my career on being a Product Manager in tech companies, so I found this wasn’t a helpful signal anymore. When I was debating if I wanted to be a marketer, data scientist or product manager, this was important though. I would be a mediocre data scientist, and thankfully, I had this metric in the rubric back in those days to help steer me away from that job path.
  • Lunch and snacks at office – This is one of the elements that people tend to overvalue. There is some value to it, but lately I’ve been working at home most of the time, so really the food at the office only impacts me a small portion of the year, meaning the weight of this has dropped much lower. Perhaps some day if I return to working from an office more days of the week, the weight will go back up.
  • Other perks – Swag like shirts, backpacks, water bottles and other random perks like employee discounts are great, but I’ve found people tend to overvalue them. People are sometimes surprised that Google doesn’t give employees free Youtube Premium, but when you remember that it only costs ~$120 a year and the average Google employee is paid >$120k per year, you realize that even if they did, the weight would only be 1/1,000th the weight of compensation.
  • Automation risk – This is another factor that I worried about more when I was deciding between dramatically different career paths. There are many career paths that I would not want to start on today because of the lack of future in front of them due to automation, particularly from AI, quickly approaching.

How I Use the Rubric

I’ve found that this rubric is particularly helpful for me in two different situations. The first is when I am actively deciding between multiple prospective roles, either because I’ve actively been interviewing or because I’m being pursued by another company. The second is when I am periodically asking myself if I am still happy in a role or if it is time to move on. That latter scenario is more passive, but I find the structured thinking still helps me feel more confident in my state if I decide to maintain the status quo.

Evaluating and Comparing Roles

I would describe the evaluation as a process that relies on thinking fast and slow, according to the definitions described by Nobel Prize winning behavioral economist Daniel Kahneman in his book by the same name.

The fast thinking part of my brain makes judgements about individual factors or how I feel overall about a job. Some of those thoughts are so fast or subconscious that I don’t even fully understand them in a way that I could describe, but they happen within my brain. For example “I have a bad feeling about this” is fast thought.

The slow thinking part of my brain then asks if that judgement is valid. Does that factor really matter that much? What is the weight set to? If it feels more important that my spreadsheet says, why is that? Should I adjust the weight? Is that rating really accurate – are those people strong co-workers or just great at seeming strong in a few conversations? What have I learned in the past that might confirm or override that fast judgement?

I’ve found that by thinking both fast and slow I can come to a better decision that has fewer biases and flaws. Over time the process is somewhat self-correcting as well. As I make job decisions and evaluate them, I learn what items ended up being accurate or inaccurate, important or not. That lets me adjust my weights and make a better decision next time.

So, in the future, even if my needs and preferences didn’t change at all, I expect I would learn more about myself in a way the prompted me to; add new factors, change what it means to score high on a factor, and adjust the weights of various factors. In reality, my needs will change based my life stage, what I accomplish in one role, strengths and weaknesses I develop and/or my personal interests.

Deciding When It Is Time to Move On

I don’t like to be indecisive. I make a decision, act on it and then pause to reevaluate. With jobs, I find that it is worth it to poke my head up and look around about once a year. Looking around more frequently can make it difficult to accomplish things and result in an analysis paralysis. Spending too long without looking around can cause you to miss opportunities or end up being boiled alive by increasing heat (like the frog in the metaphor).

To start a periodic review process, I usually pull up the rubric and reevaluate my current role. Have my ratings changed on any factors? Either because the job itself changed or because I had been making a guess before and now I have more data. Have my weights changed on any factors?

Over time I’ve resigned myself to the practical philosophy that there will never be a perfect job. There are pros and cons to each job. In my experience there is a bell curve of options and the higher score you’re looking for, the less likely it is to exist and be available at any given moment. So as I reevaluate my current role, I have to ask myself, what are the chances I will find another role that scores higher, and is it worth it to invest the energy to look for that other role actively?

What I’ve found is roughly this:

  • if I’m at a 0.8 on my scale, it really isn’t worth looking around, I should just keep at my current job as I’m usually quite happy in a 0.8 role.
  • If I start to drop into the 0.7 range, it might be possible to find something better, so I might open my ears a bit for promising opportunities, but I wouldn’t have much urgency.
  • If a role ever drops into the 0.6 range, it might be time for me to do a full, active, job search. To call up some contacts I haven’t talked to in a while and catch up or take folks out for coffee.
  • If a role ever got into the 0.5 or lower range, I might actually quit my job to focus 100% of my energy on a job search. I haven’t had that happen, but I’ve sometimes considered it and advised it to other people whose situations have gotten to an equivalent state.
  • If a job ever pops up somewhere that seems like it might be 0.9 or higher, I will pay attention, because I know how rare that is. In those cases, I then have to ask, is it worth considering more options at the same time, or is it enough to compare my current role and this new one. Generally I’ve found that if I have two strong options, a third option won’t materially change the result of the process but pursing it could add a lot of extra effort and complexity.


The rubric isn’t perfect, but it helps me process through a big decision I tend to only make a few times a decade, and I believe it helps me do so in a more effective manner. I hope it can be helpful for you too.