Here are 4 really great tips for you to think through as you consider that next job… or even personal side-hustle or side-project (via @jensenharris):
1. Start with People
Always, always, always choose the people. The people you work with every day will be by far the biggest factor in your work happiness. This isn’t measured just by whether they’re good happy hour companions or quick with a witty joke, however.
Great people will be invested in your success. They will celebrate your triumphs and help you through mistakes. They will offer to teach you and mentor you (and it’s mentorship you want!) Surround yourself by people who you click with, who you admire, who share your values.
Work priorities in many teams change frequently… who can even say what you’ll be asked to work on in six months? You shouldn’t choose a job based on a specific promise of the work you’ll be doing any more than you should choose to marry someone based on their haircut.
The people and culture of a team don’t change as quickly. They form the bedrock of your work experience through fun work or when slogging through hard stuff. Put even more practically, you’re going to be spending at least 8 hours every workday with these people—make them count!
Almost always when I’ve seen people “chase the work” (meaning choosing a team they like less in favor of what they perceive to be more interesting work), those people end up regretting their decision. Crappy team = crappy work experience, no matter how exciting the work is.
2. Your Direct Manager / Supervisor is Key
The direct manager is the most key person to consider. Especially inside of a big company, the manager you would be working for may be the most important factor in choosing a new role. No other single person will have as much impact on your success and happiness at work.
Over the years I worked at Microsoft, hundreds of people asked me for advice on choosing between multiple jobs and my guidance was always the same: “choose the best manager.” It is widely-known that the #1 reason people leave jobs in their boss. Bad manager = unhappy employee.
While a horrible boss will make your job insufferable, a mediocre manager will create something even more dangerous: a stagnant situation in which you end up stuck in your career, not getting the mentoring/opportunities you need to learn and grow, not unhappy enough to leave.
On the other hand, great managers tend to have people follow them from place to place, wanting to continue working in their team. It can actually be a great sign when you find a place in which multiple people have worked together elsewhere before—a signal of positive trust.
3. Look for the Big Opportunities
Optimize for the bigger opportunity. All else being equal, choose the job that has the most upside, even if it has a lot more ambiguity. Take a job at the startup, on the newer & less well-established team, the risky project. Nothing can vault your career forward faster.
Here’s the thing: the safe, predictable job is still going to exist in 2 years. You can still go to Amazon and help scale services. Yay. That job designing some aspect of the Facebook ad engine or coding Salesforce’s table view will still be there, and 100,000s more like it.
If you take a “riskier” role and decide you don’t like it after 18 months, then you can leave and take the safer job. Google’s not going anywhere, don’t worry. But by taking the earlier, bigger path you open yourself up not just to better challenges but also faster advancement.
Being on a team near the beginning of that team gives you an outsized impact on the DNA of the environment—the way it works, what gets built, who you hire. When leadership is needed, you’re the obvious choice: you’ve been there since the start. The risk turns into career reward.
So many people have rocketed to leadership positions on the back of having taken a little risk, while those playing it safe slowly plod towards their next performance review, maybe a small, stepwise promotion up one rung of the corporate ladder. You don’t have to play it safe!
4. Optimize for Learning
Go where you’ll learn. Chances are, your next job won’t be your last job. Too often people put everything else above learning when, in actuality, learning is what propels your career more than anything else. It’s what sets you up for great opportunities in the future.
So, start by taking a job that will force you to use technologies, tools, and methodologies you haven’t used before. Or choose a role working on a different kind of product than you’ve ever worked on. Done consumer? Do enterprise. Done Azure? Do AWS. Done megacorp? Do startup.
That’s not to say that you should forget everything you’ve already learned because, of course, that’s a big part of your value. But be willing to choose the job that will push you, especially if it feels a little uncomfortable or exciting. The safe job won’t grow you.
And make sure you pick a team that wants+expects you to learn.
During your interview, ask explicitly how the team supports learning. Ask what they’ve learned over the last 12 months. Get concrete examples of opportunities people had to step up into new, uncomfortable roles.
All of this advice, of course, assumes you have the luxury of job choice, and is targeted at tech and related types of jobs. Many people have financial, family, and other considerations that limit their choices; I’ve been there too and know you have to take the job you get.
In the end, choosing a new job doesn’t need to be stressful. Choose great people, a team that shares your values, and the best manager you can find. Optimize for a big opportunity, and go where you’ll need to learn and try new things. Do this, and you’ll make a great choice!