Finding Fit

Specialists want to dive deep into their subject matter, carving out a particular area of expertise and learning skills to deal with nuance and complexity – getting deep into a codebase or shipping new features, developing a targeted skill set for SEO optimization, tackling sales enablement for a specific product set, or honing in on audit prep. Generalists pick up skills like a magpie, collecting a wide toolbox. If you’re drawn to the generalist mindset, you get energy from wearing different hats that switch based on need. In the generalist camp, you’ll value being good enough at a lot of things and being able to jump into varied tasks that add value.

How much room for creativity and self-direction do you want at work? It’s the difference between a role that is already established and has clear boundaries for expectations and success and one that was created based on need and determining how to allocate your time and figure out what will add the most value, whether that’s in the job description or not. On a day-to-day level, you might ask yourself what proportion of your work tasks, assignments, projects, and deliverables do you want to be given to you by a supervisor or team member? Are you excited about opportunities to generate your own projects through observation, problem solving, collaboration, and determining how to best add value? If you identify primarily as an executor, you may want a workflow that comes from a defined organizational hierarchy. If you’re also strategy-minded, you might prefer a workflow that requires you to take initiative more often to develop your own tasks and projects. Put another way, how much of your role do you want outlined in a preexisting playbook and how much do you want to create yourself?

Executing tasks means taking a part of a larger plan that falls in your wheelhouse and delivering on it. On this tactical end of the spectrum, you’re dealing with immediate and short-term activities with narrow and focused goals. If you get a real thrill from checking things off a to-do list, you’re likely a more tactical thinker. Outcome ownership is more closely tied to big picture thinking. Strategic planning and decision-making zooms out to long-term goals and the “why” driving your work. Those goals then translate into achievable steps and, ideally, a tactical, workable plan for getting there. You may never do a purely tactical job or a purely strategic one, but consider how much you care about having input in the larger goals and directions of a company.

Upskilling, mentorship, and professional development come in a wide variety of flavors. Your learning style may be best served by targeted training, robust onboarding programs, online courses, or formal continuing education. These types of resources can be helpful when you need to level-up your specialized expertise or learn a specific skill. On the other side, you may value a more hands-on, dive-into-the-deep-end approach. Or maybe you like the idea of a more structured learning opportunity, but only if you’ve identified it yourself and done the legwork to know that the course or conference or certification fits your needs and provides immediate value and tangible skills you can put into practice.

Do institutionalized systems and publicly defined things like org charts, training programs, benefits, incentives, and workflows bring you a sense of stability and comfort? Do you read systems as rigidity and bureaucracy or as built-in layers of protection and more professionalization? Perhaps instead you’d rather opt for flexibility, agility, and adaptability. A more flexible framework might include more risk but can pivot faster, personalize incentives, and tolerate new and more creative ideas better.

This question is a complicated one because there’s no getting away from some level of risk. One way to analyze decisions is through asking three questions: 1. What if everything goes wrong? 2. What if everything goes right? 3. What if things get weird? Under that rubric, even the most solid, conservative, steady company might have trouble making payroll or hand out pink slips to an entire department or get squeezed out by unforeseen new technology or have a fly-by-night moonshot that turns into a steady bet. Or a global pandemic could happen and turn routine on its head.

So you might think instead about how much you value and require predictability and the capacity to plan. Do you prioritize layers of protection that insulate against rough seas or agility and the ability to pivot and incorporate new information and pursue new ideas, even if that requires more risk?

Obligatory caveat: We all want to be paid fairly and well for our work and have access to benefits that allow us to live and work without fear and with more and better capacity. The distinction here is whether you are inclined to define the reward you gain from work explicitly and exclusively in terms of compensation, benefits, and monetary incentives or if you think of reward in a broader context around meaningfulness of work, ability to form bonds with coworkers, outcome ownership, and intellectual challenges.

Job titles and clear org charts provide more validation points and distinct career ladders. This is particularly important if you want a documented, benchmarked path from junior to senior to manager to director (it’s also easier to articulate the process to external parties like spouses or parents). If you’re less concerned with titles, timelines, and validation points, you might instead prioritize diversifying your skillset and preparing for a wider range of opportunities. In this case, you’re probably comfortable with expanding the sphere of your responsibilities, whether they’re associated with a job title or clear “next step” or not.

Impact ownership takes many forms. This could look like the difference between work that impacts your co-workers rather than impacting customers. Or it could look like the difference between work that has a more targeted impact and lower risk versus work with a broader impact and greater potential set of outcomes. Also involved in this calculus is whether you want your work to be geared towards the wants, needs, and expectations of customers or shareholders.

Your feelings on anonymity and access are closely related to how visible you want your work to be within an organization. This, in turn, is dictated by both the nature of your work and the structure of an organization. If you’re more comfortable in work environments that allow for less visible, more anonymous contributions, you might value the protection and buffers that layers of personnel between you and the C-Suite provide. However, if access to leadership and visibility and ownership of results are important to you, you’ll also want fewer doors between you and decision-makers.

This question is most immediately applicable to more entry level roles where you might consider if you prefer having co-workers that are doing the same or similar jobs or being the one person tasked with your role and function. But there’s a broader way to think about this scale that does translate to more advanced career stages. For a role you’re considering, think about how painful it would be to your colleagues if you left. Is there a lateral position that could cover your role or someone a step down the ladder that could step up relatively quickly and painlessly? Or would it be difficult to replace you? Then determine what situation gives you more utility or pride.

What does your ideal future look like? If you’re trying to increase your marketability at another big company, a high level of expertise can translate to moving up the ladder you’re on or jumping onto a higher rung in a new, but fundamentally similar, ladder. If you want to nurture an entrepreneurial spirit, long practice with a broad set of skills will serve you better. 10,000 hours spread across many different operational areas may not make you Tiger Woods, but it will make you good enough at a lot of things, which can make you better suited to identify and seize market opportunities in the future.