Last week, we talked about one huge question, “How the hell are you supposed to have a career in tech in 2026?” That’s pretty specific to this current moment, but there are some timeless, more perennial questions I've been sharing with friends for years that I wanted to give to all of you. They're a short list of questions that help you judge whether a job that you’re considering is going to crush your soul or not.
Obviously, not everyone is going to get to work in an environment that has perfect answers to all of these questions; a lot of the time, we’re lucky just to get a place to work at all. But these questions are framed in this way to encourage us all to aspire towards roles that enable us to do our best work, to have the biggest impact, and to live according to our values.
The Seven Questions
- If what you do succeeds, will the world be better?
This question originally started for me when I would talk to people about new startups, where people were judging the basic idea of the product or the company itself, but it actually applies to any institution, at any size. If the organization that you’re considering working for, or the team you’re considering joining, is able to achieve their stated goals, is it ultimately going to have a positive effect? Will you be proud of what it means? Will the people you love and care about respect you for making that choice, and will those with the least to gain feel like you’re the kind of person who cares about their impact on the world?
- Whose money do they have to take to stay in business?
Where does the money in the organization really come from? You need to know this for a lot of reasons. First of all, you need to be sure that they know the answer. (You’d be surprised how often that’s not the case!) Even if they do know the answer, it may make you realize that those customers are not the people whose needs or wants you’d like to spend most of your waking hours catering to. This goes beyond the simple basics of the business model — it can be about whether they're profitable or not, and what the corporate ownership structure is like.
It’s also increasingly common for companies to mistake those who are investing in a company with those who are their customers. But there’s a world of difference between those who are paying you, and those who you have to pay back tenfold. Or thousandfold.
The same goes for nonprofits — do you know who has to stay happy and smiling in order for the institution to stay stable and successful? If you know those answers, you'll be far more confident about the motivations and incentives that will drive key decisions within the organization.
- What do you have to believe to think that they’re going to succeed? In what way does the world have to change or not change?
Now we’re getting a little bit deeper into thinking about the systems that surround the organization that you’re evaluating. Every company, every institution, even every small team, is built around a set of invisible assumptions. Many times, they’re completely reasonable assumptions that are unlikely to change in the future. But sometimes, the world you’re working in is about to shift in a big way, or things are built on a foundation that’s speculative or even unrealistic.
Maybe they're assuming there aren't going to be any big new competitors. Perhaps they think they'll always remain the most popular product in their category. Or their assumptions could be about the stability of the rule of law, or a lack of corruption — more fundamental assumptions that they've never seen challenged in their lifetime or in their culture, but that turn out to be far more fragile than they'd imagined.
Thinking through the context that everyone is sharing, and reflecting on whether they’re really planning for any potential disruptions, is an essential part of judging the psychological health of an organization. It’s the equivalent of a person having self-awareness, and it’s just as much of a red flag if it’s missing.
- What’s the lived experience of the workers there whom you trust? Do you have evidence of leaders in the organization making hard choices to do the right thing?
Here is how we can tell the culture and character of an organization. If you’ve got connections into the company, or a backchannel to workers there, finding out as much information as you can about the real story of its working conditions is often one of the best ways of understanding whether it’s a fit for your needs. Now, people can always have a bad day, but overall, workers are usually very good at providing helpful perspectives about their context.
And more broadly, if people can provide examples of those in power within an organization using that power to take care of their workers or customers, or to fight for the company to be more responsible, then you’ve got an extremely positive sign about the health of the place even before you’ve joined. It’s vital that these be stories you are able to find and discover on your own, not the ones amplified by the institution itself for PR purposes.
- What were you wrong about?
And here we have perhaps one of the easiest and most obvious ways to judge the culture of an organization. This is even a question you can ask people while you’re in an interview process, and you can judge their responses to help form your opinion. A company, and leadership culture, that can change its mind when faced with new information and new circumstances is much more likely to adapt to challenges in a healthy way. (If you want to be nice, phrase it as "What is a way in which the company has evolved or changed?")
- Does your actual compensation take care of what you need for all of your current goals and needs — from day one?
This is where we go from the abstract and psychological goals to the practical and everyday concerns: can you pay your bills? The phrasing and framing here is very intentional: are they really going to pay you enough? I ask this question very specifically because you’d be surprised how often companies actually dance around this question, or how often we trick ourselves into hearing what we want to hear as the answer to this question when we’re in the exciting (or stressful) process of considering a new job, instead of looking at the facts of what’s actually written in black-and-white on an offer letter.
It's also important not to get distracted with potential, even if you're optimistic about the future. Don’t listen to promises about what might happen, or descriptions of what’s possible if you advance in your role. Think about what your real life will be like, after taxes, if you take the job that they’ve described.
- Is the role you’re being hired into one where you can credibly advance, and where there’s sufficient resources for success?
This is where you can apply your optimism in a practical way: can the organization accurately describe how your career will proceed within the company? Does it have a specific and defined trajectory, or does it involve ambiguous processes or changes in teams or departments? Would you have to lobby for the support of leaders from other parts of the organization? Would making progress require acquiring new skills or knowledge? Have they committed to providing you with the investment and resources required to learn those skills?
These questions are essential to understand, because lacking these answers can lead to an ugly later realization that even an initially-exciting position may turn out to be a dead-end job over time.
Towards better working worlds
Sometimes it can really feel like the deck is stacked against you when you're trying to find a new job. It can feel even worse to be faced with an opportunity and have a nagging sense that something is not quite right. Much of the time, that feeling comes from the vague worry that we're taking a job that is going to make us miserable.
Even in a tough job market, there are some places that are trying to do their best to treat people decently. In larger organizations, there are often pockets of relative sanity, led by good leaders, who are trying to do the right thing. It can be a massive improvement in quality of life if you can find these places and use them as foundations for the next stage of your career.
The best way to navigate towards these better opportunities is to be systematic when evaluating all of your options, and to hold out for as high standards as possible when you're out there looking. These seven questions give you the tools to do exactly that.
/s3/static.nrc.nl/images/gn4/stripped/data142311710-955992.jpg)
:format(jpeg):fill(f8f8f8,true)/s3/static.nrc.nl/bvhw/wp-content/blogs.dir/114/files/2019/07/ikje5bij3-1.png)