According to Microsoft, 41% of workers globally are considering leaving their current employers by the end of the year, a number that’s strongly driven by a desire for more flexible and remote working.

If you’re thinking about changing jobs, it can be tough to know how to define what’s important to you in a role or company, and how to look past the shiny exterior of adverts to see whether an organization can really stack up to your needs.

I changed jobs mid-pandemic when I joined Farewill (where I’m now VP of Engineering) and spent lots of time thinking about what was most important to me. Here are some things I found helpful to think through.

Start with defining the basics

When it comes to thinking about the practicalities of your next role, you’ve probably already got things in mind. For example:

• The kind of job you want for your career trajectory, maybe including specific titles, or level of seniority.
• The level of salary you need, and what’d be really nice.
• Other parts of the package, like holiday, stock options, learning budget, parental support, or perks like gym membership.
• Working arrangements (e.g. working from home, where the office is, how sick leave is handled).
• Type of organization (e.g. public, private, or third sector; product company or agency).
• Size of organization.
• Technologies you’d get to work with.
• Whether you want to work full time, part time, or even freelance (a whole other topic!)

These aspects are usually fairly easy to define. You’ll likely be able to pin down some of them pretty rapidly, and you can then match your list to most job ads.

Outside of that though, it can be much harder to be clear on exactly what you’re looking for, and even harder to find out if a company is really a match. Let’s dig deeper.

Reflecting on the environment you’re after

Think about the below in terms of environments you’ve been successful in previously, or which you’re interested to try out. You can then take the things you’ve realized you care about (not everything will be important to you!), delve a bit deeper and gather information about companies that could be a good match.

Company situation

Going beyond just the size and type of company you think could be a good fit, it can also be important to consider what mode of operation you’re most drawn to. In his book The First 90 Days, Michael Watkins describes this using the ‘STARS model’, where companies are categorized into Start-up, Turnaround, Realignment, and Sustaining-success, and either in a Growth Cycle, Recovery Cycle, or Crisis Cycle. This isn’t just tied into a company’s maturity stage, for example, profitability can be a rollercoaster with startups, but larger companies are also not immune to big layoffs and drastic changes in tactics. 

Different modes will typically mean different ways of working and areas of focus, which may not match up with how you like to work. I find it useful to consider what modes drain me, which I’m most excited about, and the kind of company goals I’d find most motivating.

Company culture

For me, this is a big one. I want to know whatever workplace I’m joining has similar values to me, and has a culture I’ll enjoy being part of and can contribute to.

Everyone has their own personal view on what makes a great culture. For some it’ll be things like transparency, commitment to diversity, equity and inclusion (DEI), or environmental impact. For others it’ll be regular social opportunities, chances to engage with leadership, or a high-performance culture they know will challenge them.

Some of the things I personally look out for include:

• Whether the company has published values, and if these align with mine.
• Whether I feel they’re working towards net good in the world.
• If there are progression frameworks published, to see how people can grow. 
• Signs of who does well there, including diversity of leadership, what kind of people are getting promoted (and who isn’t), especially into more senior engineering levels.
• The approach to remote or flexible working (or lack of!)
• Do they walk the walk? Everyone will say topics like DEI, mental health, and burnout are important, but what does that look like in practice?

Team culture

You could then think about the type of team you’d enjoy working with more directly. This could be a more localized team (the folks you collaborate with daily to achieve goals), or a wider group like engineering broadly or a frontend guild. Depending on the type of workplace you’re interested in, this may be small, or there may be several layers. This then becomes about the type of environment you’re excited to do your best work in. For example:

• How easy do you want it to be to make technical change happen, or get buy-in to work on technical investment projects? Do you enjoy places that are immediately open to new ideas, or where you can have an impact through changing minds? 
• What’s important to you around work-life balance (on-call, or working late)?
• Are learning opportunities important to you, and what would you like these to look like?
• What kind of relationships and team bonding opportunities do you enjoy?
• How much stock do you put in team performance, and contributing factors like psychological safety and autonomy?

Teams with problems aren’t necessarily bad. Maybe you’re the kind of person who likes making sweeping changes, being the hero when things are off track. Or maybe there’s loads of tech debt, but you enjoy this and you know they’re committed to giving you space to work on it.

Key relationships with individuals

Your interactions with some individuals can have a big impact on your day-to-day experiences. Some areas to think about include:

• What kind of person you’d ideally report to. What motivates them, and what kind of working style do they have?
• Your peers. Who would you like to mentor you? Who would you work with day to day? If you’re joining a team who pair all day every day, but you find that stressful, the relationship may not work for you.
• Who would lead your function? What’s their vision and what do they stand for?
• People who’d report into you, or who you’d be responsible for supporting. What kind of relationship would they be looking for?

Gather information about potential options

By working through some of the topics above, you’ll naturally start to pin down aspects of a workplace that excite you, and which you gravitate to more than others. Once you have this you can start your detective work to see how potential employers stack up. The best ways I’ve found to do this are:

Find a hiring contact, or get in touch with employees directly

Some companies include a contact email to use for speculative questions, but if you can’t find one see if you can find a relevant person (such as the head of department) on LinkedIn or other channels. They may not be able to talk outside of an official process, but could be up for an informal chat or to answer email questions.

Ask your network

It can be a small industry, and if you’ve got even a little bit of a network there’s a good chance someone you know will have a connection to the place you’re interested in – whether directly or indirectly. Asking for people’s experiences can give you a very honest insight into areas you’re interested in – something that can be particularly useful for folks from groups underrepresented in tech who want to hear real accounts.

Do some research

Many companies have blogs, culture pages, or externally published articles that can give you a feel for some of the topics you may be interested in. These could range from the technical details of how systems were built, to reflections on outages, through to information on their approach to progression.

Dive into the interview process

Even if you’re not fully sure that the job is right for you, the interview process can be a good opportunity to ask questions. If you don’t have enough time during the discussion itself, many interviewers or talent teams are happy to follow up afterwards. As things progress, try to speak to a range of people, and if you have the luxury of being able to afford extra time, ask who else you may be able to meet. (For more advice on interviews, take a look at my previous article about questions you may want to ask.) 

Putting it all together

Hopefully, by this point, you have a clear idea of your perfect role and company and have gathered a fair amount of information about your options. 

Unless you’re very lucky, it’s unlikely you’ll find something that’s an absolutely perfect match. In reality, you’re likely to need to make tradeoffs and compare very different options. Even if you think you’re sure about what you’re after, it can sometimes be worth throwing wildcards into the mix to challenge your thinking and give you exposure to other possibilities.

Good luck!

Now you’ve pinned down the best opportunities, it’s time to focus your attention on the application process. Fingers crossed that one’s a great match on both sides!