Should I stay or should I go? Part 2
Tips on choosing your next role, and avoiding being sucked in by seductive job ads.
So you've decided to start looking for a new role. Or perhaps something that piques your interest has popped up. Roles are 'advertised', so, like ads, they're meant to look attractive at first glance. How do I guard against the onslaught of job ads and avoid jumping at one I soon regret?
I believe it comes down to three fundamental principles:
Understanding what you want to learn and experience in your new role.
Understanding how you work and how much you want to change.
Ensuring prospective roles align with what you want and how you operate.
What do you want to learn and experience?
As per my previous post about the importance of learning in your role, think about what you want to learn and experience in your next job. This helps identify a role that fits and prevents you from rushing into one you later lament.
Do you want to learn more about scale and reliability? Then, you might want a platform team role in a larger company.
Do you want to experience working with users and product management? Find a role on a product team, and ensure you understand their product.
Unfortunately, your past experience can typecast you into specific roles or domains. For example, having worked in identity and access management, I've received many pings for roles on similar teams in different companies. You may be interested in taking these roles to experience building a system or team from scratch or to learn if your knowledge translates to a new industry. Like typecast actors, you need to decide if that's what you want or if you want to break out.
I also caution against targeting a specific company because you love its products and want to learn how that company works. You limit your options, and, like the adage of meeting your heroes, you may also find that it is not as glamorous as expected. Start with what you want in a role first. If such a role exists in a company you admire, that's icing on the cake.
How do you like to work, and how much are you willing to change?
We often want new experiences. The grass is always greener on the other side. Engineers who have always worked in behemoths wish to experience 'the startup life'. We must understand how we like to work and how malleable we are. Without this understanding, we risk breaking ourselves.
Simon Wardley (of Wardley Maps) has previously talked about pioneers, settlers and town planners, which can serve as a good starting point. Paraphrasing:
Pioneers are those willing to explore crazy ideas and work in highly ambiguous areas. They hack together the 0-to-1 prototypes to demonstrate a north star for an organisation.
Settlers take the pioneer's ideas and productionise them.
Town planners then scale and optimise what settlers have built.
Understand which of these you gravitate towards and what you want to experience. Personally, I've progressed from town planner to settler and now want to do more pioneering. Some engineers like to stay as one type, which is totally valid. If you want to transition, be reasonable about how much of a leap you want to take in each new role. Jumping straight from town planner to pioneer could be jarring.
Company and org size
Another facet to consider is how much order in chaos you like and how much structure you are willing to introduce into a system. This helps determine the maturity of the organisation you want to target. I like analysing problems methodically and introducing and improving team processes to minimise wasted effort. Therefore, I know I like small-medium organisations where I can help mould how they operate, and I would find it challenging in a tiny startup running frantically to get a first user. Others like operating with robust pre-existing processes in large organisations, or exploring issues based on gut feeling alone in tiny teams.
Large companies have a reputation for bureaucracy and moving slower, but offer the safety of likely not collapsing quickly and a good pay packet.
Luckily, there can be opportunities for large companies to operate in smaller, isolated organisations; these may be nascent products or newly spun-up locations. These are not authentic startup experiences, but they can give you a sense of how much startup life you can take.
Changing teams vs changing companies
Changing roles doesn't always need to mean changing companies. If a company is growing, there are usually many opportunities outside your current team or org. It is easier to learn more about your potential teammates and managers as you can ping current or ex-members of the team. You can get an accurate assessment of the team's challenges through internal documents written by the team. Visibility of the team to leadership, a strong indicator of the team's importance to the company, should be easy to ascertain through town halls or strategy documents.
Changing companies presents many risks. You will likely need to work with many new people and prove yourself to them. Although some company cultures are similar, there will always be some subtle differences that are difficult to understand until you experience them. Unless the role involves directly working with an ex-colleague willing to share their perspective, it will be challenging to get a true sense of what a team is doing and how they are perceived by leadership and the rest of the company.
Given these risks, unless your goal is to get out of your company's bubble and expand your network, or the company culture is toxic to you, I feel moving between teams in a company should be your first port of call. Look around for internal opportunities first before taking the bigger leap.
Finally, aligning on expectations.
Armed with a clear understanding of what you want from your next role, it's time to ensure prospective roles match your expectations and your hiring manager is aligned.
You will likely discuss upcoming projects that you may work on to align the role with areas in which you want to grow. However, take these projects with a grain of salt. They may pivot by the time you arrive. Also, use your judgment about how realistic a project is; the goals may sound incredible, but if it is too good to be true, it'll likely pivot or be cancelled. Instead, try to learn about all projects a team and partner teams are working on to better understand the strategy of the team, organisation and company and see if that matches what you are looking for. If everyone works to drive improvements in the same area, the strategy will likely stick even if specific projects change.
To understand how you are expected to work, be clear on who you will work with and their roles (other engineers and/or other functions). Who comes up with the crazy ideas to explore? How does the team fit into the broader organisation and company? How large is the team? What are the experience levels of team members? Use this information to create a model of what role you and your team are expected to play (pioneer, settler, town planner) and the organisation's maturity (are you there to improve how it operates?).