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Why you should talk to 30 people (and build a spreadsheet) before changing jobs

June 21, 2021 in Career Transitions

With vaccination rates rising and government restrictions lifting, employers across North America and Europe are beginning to plan for physical office re-openings (or permanent closures!) The consensus is that we’re entering a massive talent shuffle, as employees whose personal working preferences don’t line up with company policies explore opportunities at companies where they do. a16z, Homebrew, Axios, and Bloomberg have all written about it.

Mass adoption of remote-first working will be a huge driver in how the next generation of employees, particularly startup engineers, evaluate career transitions. Some go so far as to argue that the career transition will be relatively simple—the most talented people will pick up and go directly to their current employer’s competitors if they can’t work remotely.

I don’t buy it. Remote-first work is absolutely a factor in making a career transition. It’s part of what compelled me and all my colleagues at Commit to join our company. But if everyone built a decision matrix, and applied different weights to the factors that mattered to them most while they navigated career transitions, a very (very) small subset of the population would weigh remote-first 100%.

Exhibit A: A sample decision matrix for navigating job transitions that is likely applies for only a very (very) small subset of the population

Company AttributesDecision Matrix Weights
Leadership team0%
Tech stack0%
Potential for growth/learning0%

Some subset of people likely do want to stay in the same industry (and product space), and so are compelled to join a competitor—especially in network-driven jobs like enterprise sales or venture capital.

This is much less likely for software engineers working at tech companies.

How people actually evaluate career transitions

At Commit, we help engineers navigate career transitions and decide between different startup opportunities. At any given time, an engineer is evaluating opportunities in different industries, at different company sizes, with different engineering cultures, using different tech stacks, and on different engineering teams (e.g. platform vs growth).

Everyone’s weighted average scorecard looks a little different. But crucially, we all build one.

Exhibit B: A sample decision matrix for navigating job transitions that’s more representative for the average startup engineer

Company AttributesDecision Matrix WeightsMust-Have
Leadership team30%
Tech stack10%
Potential for growth/learning—specifically exposure to data engineering50%
D&I policy and exec championY
Has raised VC fundingY
Team lead has previous management experienceY

When I was navigating my personal career transition last year, I followed a five-step process:

  1. Map out my skills
  2. Talk to 30 people in the universe of roles I was considering.
  3. Overlay my skills and preferences against the role maps I had built to see how I would contribute, where I would grow, and which skills I wouldn’t leverage.
  4. Identify the company attributes that mattered to me and assign them weights.
  5. Build out a weighted average scorecard and test its output against my gut.

I treated my career transition the same way I treated a potential investment, and when I joined Commit, I discovered that a lot of my colleagues had done the same thing.

Sim Brar has focused his evaluation framework on pairing gut instinct with hard calculations. His approach:

  1. Define the attributes that matter to me (i.e., autonomy, growth, responsibilities, salary, company growth, interest in product).
  2. Score each opportunity against them on a scale of one to five.
  3. Look at the results and evaluate if the ensuing trade-offs make sense or if your gut is telling you that a lower-scoring opportunity should be higher.
  4. Use a derivative of Tim Ferriss’ Fear Setting exercise: ask, “What’s the worst that can happen, and what could I do to remedy that problem—either before starting or after I took the opportunity?” to reduce resistance to change and the unknown.

While Brian St. Amand was evaluating whether he wanted to graduate from a pilot and join that company full-time or re-enter Commit and look for new opportunities, he acknowledged that every decision has trade-offs, and rather than selecting the option with the fewest trade-offs, he looks for roles where he can build a mitigation plan against them. His approach:

  1. Map out the attributes that matter to me (e.g., leadership style, mission, potential to learn about the industry, teaching vs learning ratio, skill development in backend and in product, tangible impact on customers). 
  2. Build a pro/con list against them.
  3. Identify a mitigation strategy for the trade-offs that come with every role.


For most people, this analysis takes place in their head, and often relies more on gut instinct than on hard calculation. As we’ve learned at Commit, these two things don’t have to be at odds.

Sarah Marion leads Founder Partnerships at Commit. She’s spent her career collaborating with early stage founders as they solve valuable problems.