A Framework for Deciding Your Next Job

TL;DR Consider being very methodical about your next job change. Evaluate the opportunities across 16 different factors. Here’s a tool to help.

We each have our own vaguely defined ideal states for our lives — some people optimize for happiness, others for fulfillment, others for legacy. Regardless of what one optimizes for, where you work is a vital component to achieving your ideal state since it takes up such a substantial portion of your waking hours.

After changing jobs half a dozen times in the last decade, I’ve gotten a bit wiser and far more methodical about how to select my next job. This is an attempt to abstract my selection criteria into a framework that can be useful to others when selecting their next opportunity (specifically a job for a tech company since that’s what I know). I’ve included my selection criteria for the job change I made in September 2016 to illustrate how I applied the framework.

Assumptions

Some assumptions to start:

• You’ve already done some degree of self-reflection about what’s most important to you in life.
• It’s better to be proactive about choosing where you work rather than relying on the perfect job falling in your lap.
• It’s better to have a focused, curated shortlist of companies that meet your criteria, rather than spraying your resume to dozens of employers.
• It is pretty privilege-y to think you can work anywhere. However, you may have more opportunity than you think and proceeding with thoughtfulness and deliberation will be your friend.

16 Considerations When Hiring Your Next Employer

1. Size & Age of Company

How old and how big the company is will determine your experience working there more than any other factor. Generally, in small companies or large-but-young companies you’ll find a complete lack of process and structure. If you thrive on autonomy, variety, and chaos, then you’ll be fine. You’ll learn a lot and move quickly. Generally, at large companies you’ll find a lot of things have been figured out — best practices for process, lots of structure, and lots of support. However, large companies tend to move much slower, and your impact will be far more narrowly scoped.

For Example: After previously joining a 12-person startup, I was looking to go a bit larger. I decided 200 to 1,000 employees and 4+ years in existence would be a good target for me — not too big and slow but should have some things figured out.

2. The Founders’ Backgrounds

The founders of the company set the culture by applying their personal beliefs and values. Those values inform who gets hired or promoted and how key strategic decisions are framed. And the backgrounds of the founders inform who they are, where those values come from, and what sort of biases they have. Be sure to consider their education and employment histories.

For Example: I was looking for at least one technical co-founder to ensure that the company would understand the maker-mindset at an intuitive-level. And I was looking for a CEO who wasn’t a first-timer or had been doing it for at least five years, to ensure some of the growing pains of a first-time manager and leader were resolved.

3. Caliber of Leadership

A big differentiator from company to company is quality of their leadership. This can be one of the hardest things to assess from the outside looking in and may need to be evaluated during the interview process. However, you can get some signal from their writing online in how they articulate their philosophy, ethos, and vision. Additionally, the employees’ evaluation of the company leadership via Glassdoor reviews can provide meaningful input. Ultimately, the sum total of the leadership team’s decisions will shape the fate of the company, so evaluate them critically.

For Example: I was looking for a leadership team that had not just ambition and intelligence but also empathy and introspection. It can be extremely difficult to find leadership teams that embody all of that, so this was one of my highest bars.

4. Mission & Vision

If you believe like I believe, we are responsible for the work we put out into the world, it’s important to think long and hard about the social impact of the company you join. Who does it help? Who does it hurt? If it’s massively successful, are you creating a world more or less aligned with your values?

For Example: I recognize that by participating in capitalism, I make some ethical compromises. Therefore, my goal was to work somewhere that I could feel okay about spending 40+ hours a week building. Ideally, the company would have some sort of positive benefit for folks beyond coastal, upper-class tech workers. (So this was a relatively low bar, that I was pleasantly able to surpass.)

5. Type of Business

The type of business will dictate how the company is structured and who your customers will be. For example, with business-to-business products, it can be harder to understand how you are impacting end users because your customer is another business—not their customers. Or if the business is selling physical products, it will require significant people resourcing for physical processes like distribution. Those expenses could reduce how much the company can afford to invest in technology.

The logical conclusion of how a business type would operate is generally common sense, but it’s important to make sure you give it deliberate thought and ask probing questions about it when interviewing.

For Example: I knew designing for consumers was important to me, and I’ve enjoyed companies where the software is the product more than companies where something else was the product. Therefore, I only considered companies with a significant B2C component, that were definitively software companies.

6. The Economics

Does the company have revenue? Is it significant? Is there a path to profitability? And what would that path entail (i.e. selling ads, subscriptions, selling user data, etc)? Profitability is the end goal for all businesses. Therefore, it’s reasonable to expect the company to have a coherent business model, an understanding of the market size and potential, and a product plan to get to product market fit before they run out of money (assuming they are not already profitable).

For Example: It was important to me to find a company that had achieved product-market fit, significant revenue, and a clear path to profitability in the next few years. Ideally, they would have figured out their unit economics and funding but would still have plenty of upside left on the equity.

7. Risk & Reward

Companies vary widely in terms of their ambitions. Some companies are happy to achieve profitability early on, maintain a fairly modest 1–3 million dollar business, and dedicate themselves to a small, but well-served user base. Then there’s companies looking to become multi-billion dollar empires, monopolize entire markets, and go public in a few years. And of course there’s a ton of companies in between. The important part is to find one that aligns with your personal ambitions and vision.

For Example: I was looking for a ventured-back, fast growth company with grand ambitions that had yet to be realized — a company with some traction but a lot of remaining opportunity. I knew a modest, “lifestyle” business would not be for me right now.

8. The Work

The work is what you do all day, every day. It’s easier to get through your days when you’re inspired, interested, and challenged. Picture yourself doing the job day-in and day-out. How do you think you’d feel? Also, consider how the work will evolve. A company should have a good sense of their direction for the next 12–18 months. As the company moves in that direction, will the work remain interesting?

For Example: I was looking for the company’s leadership to articulate what they believed was most strategically important for the business over the next 12–18 months. Given that information, I could decide whether those strategic priorities sounded like significant design challenges or not.

9. How the Work Gets Done

Although “The Work” is important, possibly even more important is how the work gets from start to finish. It’ll be a collaborative process with many stakeholders and where the organization’s power dynamics start to show. Who has the ultimate say? Is it one person or a committee? Who decides your priorities? And are you okay with that?

For Example: I look for fairly standard explanations of how work gets done — relatively autonomous teams working quickly to ship features, learn, and improve. I was on the lookout for red flags like stringent approval processes, micromanagement from leadership, or a slow cadence of shipping.

10. Values & Culture

Culture is the day-to-day manifestation of a company’s values, their real values, not just the ones on the website. The values are what steer decision-making, which informs culture and ultimately what it feels like to work somewhere.

Once again, Glassdoor is a great way to understand how a company’s employees are feeling, and the writing of the company’s people on blogs or Twitter give a good sense of their values. This is also something to suss out early on during the first few interviews. Ask probing questions about tough topics like diversity or empowering marginalized people and see how much thought they’ve given to the topic.

For Example: This was relatively easy to assess. Any company with less than an average employee review rating of 4.0 on Glassdoor was weeded out. Anything over 4.4 is fantastic, so I would prioritize those companies. Glassdoor’s Best Places to Work was a great starting point. Also, if the headshots on their team page lacked racial and gender diversity, that was a huge red flag.

11. Career Opportunities, Learning, & Development

If you plan to be at your next company for many years to come, then your trajectory within it and after it should matter. Your next job is the learning platform for the job after it. You should be able to see a path for acquiring the skills and experiences that will enable your next role and/or the potential for that next role at that company. Your trajectory and goals are highly subjective, so I won’t be too prescriptive here but this role should make sense in the narrative of your career.

For Example: I was looking for a role managing a significant portion of a company’s consumer-facing design. The specifics of a Manager, Director, or VP title wasn’t important. When I thought about what I wanted to learn from this next role, I was looking to gain experience working with a large design team, learn from seasoned executives, and potentially get the opportunity to manage managers. If I learned those things, I would more likely be ready to succeed in a VP of Design or VP of Product role later on.

12. Org. Support

It’s hard to be successful if the company doesn’t support your discipline. It’s pretty obvious when companies put a high value on design, but not every discipline is so easy. Look out for situations when you have to prove your value (unless you’re a masochist). Typically org. support is observable through investments in headcount and where the function resides within the org. chart.

For Example: I was looking for a company that saw design as an integral part of the company’s strategic plan over the next twelve to eighteen months and a company that believed, without prompting, that a VP of Design on the executive team was essential to their success.

13. Your Boss

Maybe you’ve heard the old adage, “People leave managers, not companies.” That’s often true. It’s a big leap of faith to join a company. You’re essentially hiring a new boss. Aim for a boss you believe is intelligent, capable, and worth following. Pay special attention, if you get the opportunity, to whether that boss has her boss’ support and confidence because your performance will be evaluated in many ways based on your manager’s performance.

For Example: For a boss, I was looking for someone who I could trust and respect, someone who I believed would let me operate autonomously, and someone who complemented my strengths.

14. Caliber of Colleagues

I’m not sure I’ve met someone who doesn’t want smart, inspiring colleagues. You’ll be collaborating and solving problems with these people every day. An ideal relationship would entail you making them better, so they should be open and receptive. And them making you better, so you should be able to see yourself respecting and trusting them.

For Example: Cross-functionally, I was looking for counterparts that were non-territorial and receptive to greater design leadership. And within the Design Team, I was looking for positive, collaborative, and eager to learn designers.

15. Location & Commute

You have to live near wherever you decide to work and deal with the commute day-in and day-out. It’s important to feel confident it’s a city you could see yourself living in and enjoying for years to come and a commute that would feel manageable even after the honeymoon period ends.

For Example: I was willing to commute up to an hour. I’m not up for moving, and I’m willing to commute by train, car, or walking. This narrows my range of possible companies to Oakland, Berkley, and San Francisco and rules out companies in Marin and the South Bay.

16. Total Compensation

Obviously compensation is a big deal. You want to work somewhere that values your contribution and shows that value monetarily. Salary matters, but it’s important to consider and evaluate the entire package. Salary, equity, benefits, potential for bonuses, perks like free meals each day, all add up to your total compensation. If you’re moving cities, be sure to use a cost of living calculator to figure out a real apples-to-apples comparison of your current total compensation and your future one. If your standard of living is going up or down to take that new job, you should understand that well in advance.

For Example: In my case, compensation wasn’t a major deciding factor as long as it hit my minimum, which was to break even with my base salary and a better total compensation package.

How To Apply this Framework

My hope is that these sixteen factors provide a useful framework to assess companies and make decisions about where to join. I put together a Google spreadsheet for you to be able to apply this to your situation. Download a copy, and use it to evaluate your next opportunities.

Last Example: I joined Thumbtack in September 2016. If your criteria aligns with how I described mine, then it’d probably be a great place for you too. Thumbtack met or exceeded my expectations in every area. I’m grateful that they were excited about me too.

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