TCW #021 | If the job fits, wear it?
Goldilocks and Alice in Wonderland both know that when it comes to things that matter, finding the right fit is paramount. Jobs are definitely one of those things.
This week, we’ll talk about how to tell if your job still “fits” you well.
In my experience, job fit is like suit fit. A well-tailored suit looks and feels fantastic, and anything else is a bit uncomfortable.
We’ve all observed friends and colleagues in each of these scenarios:
Job too big? They are drowning 🛟
Job too small? Their head is crushed against the ceiling 💂♀️
Job just right? They are hitting the balance between flow and high growth 😎
And when it comes to ourselves, we often have a hard time seeing our job fit objectively.
This post will help you (1) diagnose how well your current role fits and (2) determine what to do to get to get into the perfect fit.
Let’s dive in.
Why job fit matters
The #1 predictor of mental health in technology professionals is job-related stress. When you’re doing high-impact work that matters to you and you’re
in the right role ✅
at the right company ✅
owning the right scope ✅
— you’re on Cloud Nine (professionally).
However, when one of those things goes awry, the stress can pile on quickly.
I spent 5 years at Google, where I interviewed 2-4 candidates per week for engineering, EM, PM, TPM, Test Eng, and PgM roles. One of my highest-stakes tasks was to assess and advise on candidate leveling. Essentially, I helped determine if someone should get the title and compensation of a Junior Engineer vs a Senior Engineer vs Staff Engineer — at Google these correlate with levels (L3 to L10+).
At the same time, I was also a manager. So once those employees started, it was my job to assess employee performance against the role expectations, by level. I’ve seen firsthand the emotional stress and damage that can be caused when people are in a job that doesn’t fit them well. I’ve also worked through a number of solutions to get people into the right role fit, and every one of them is thriving today as a result.
I’m not here to say that it’s easy to come to terms with the fact that your job doesn’t fit well. It’s definitely painful to admit a bad fit, but it’s much more painful — in both the long-run and short-term — to avoid addressing the issue.
Let’s start with the two most common role fit issues: job too big or job too small.
First, we’ll walk through the telltale signs that you can use to identify if you’re in one of these situations, then the solutions that I’ve found work best if you’re experiencing poor job fit.
Job too BIG: “I’m Drowning”
When you feel like you’re treading water and constantly running at a sprint to keep up with your work, you’re going to feel stressed — that’s a given. But there are other negative consequences of being in a job that’s too big for you.
What it feels like
you’re stressed and “on” all the time, checking emails before bed, feeling overly alert and always behind
a persistent sense that you’re forgetting or missing something (possible anxiety)
your work deliverables are often late, hastily put together, and even sub-par
you spend most of your time “blocking and tackling” and have little time for strategic planning
What it looks like (outsider’s perspective)
you look stressed and frantic
you seem like you need more help
you may even seem unreliable (if you’re missing deadlines or delivering substandard work due to the overwhelm)
on the flip side, you may seem calm and collected to colleagues, but they may feel that your work is substandard nonetheless
Getting to the right fit
Case 1: Descope
Sometimes, you have all the skills for the job, but just too much scope. If so, you need to descope.
To do this systematically:
Write down all the major components of your work
Estimate weekly effort for each activity (or time track for 2 weeks using a tool like Toggl, if you want to be more scientific)
Stack rank efforts by two factors: (1) your competency, (2) your level of interest
After you hit ~35 hours per week of effort, draw a line. Anything below that line needs to get descoped. Propose new owners (or delegate if you have this ability), and then work with your manager for any residual tasks
Example
I created a ready-to-use template you can use for this exercise. Grab it here.
Case 2: Consider demoting yourself
PS: This sounds way scarier than it actually is.
Sometimes, you’re actually not competent enough for the role — as in, you lack the skills to do the job well enough.
This happens all the time, and it’s not entirely your fault. Companies frequently hire and even promote people above their capabilities (see: the Peter Principle). At fast-growing companies, the work environment can shift so quickly that you can’t grow fast enough to meet the new demands for your role.
The trick is to acknowledge that being in the right role, even if it’s smaller, is better for your long-term growth and mental health.
How to demote yourself effectively:
Go back to an IC role. If you are a new manager struggling with management, consider if you might be happier or more successful as an IC (note: I see this happen all the time in technical roles. Often, new engineering managers decide they prefer technical work over management work. It’s not going to surprise anyone or limit your long-term growth).
Bring in the Cavalry. Build a case for and inquire about hiring a more senior leader above you. Taking the lead signals your maturity and can avoid a prolonged and/or awkward demotion or even firing. Plus, you may get to keep your compensation and/or title. Your new manager can help you reallocate your work and get you on a more comfortable growth trajectory. TLDR: Getting layered, especially if you take an active role in making it happen, can be a major positive for your career.
Job too small: “I’ve Hit a Ceiling”
Being in a role that you’ve outgrown feels, well, stagnating. I’ve had many friends and clients hit this point in their career, and not wanting to look for something new, they wait it out for a promotion or a bigger role, but it doesn’t always come. Why? Because this problem has an insidious feedback loop.
They decide to wait for the opportunity to come. They might even tell themselves they are “coasting” or “resting” while they wait.
Before they know it, they’ve stagnated. Their growth is at a standstill, and their energy is low.
They find that it’s hard to get re-engaged and build momentum for themselves.
It’s ok to “rest and vest” for a few months here and there, but if you find yourself coasting or hitting the ceiling for too long, you run the risk of skill atrophy, stagnation, and loss of momentum in your career trajectory.
What it feels like
“Job too small” can be caused by internal factors or external factors, so it can also present itself in many different ways, including:
You’re coasting. You get your work done in <20 hours per week.
You’re stuck. You know you are stagnating, but you feel too lazy or burned out to summon the energy to overcome the stuckness.
You’re blocked. You’ve asked for more. The company or your manager just can’t seem to give you meatier work.
What it looks like (outsider’s perspective)
This one can be particularly subtle for colleagues to notice, since the reasons can vary so widely.
If you’re an expert on The Thing they need, co-workers often don’t notice that you’re stagnating, because they appreciate that you’re an available “go-to” person. Don’t expect them to say anything.
If you’re trying to get promoted but it’s just not possible, your co-workers may notice it more, and they may provide verbal validation that you’re overdue for role growth. Use this to motivate you to take action.
If you’re willfully coasting and you have a manager who cares about your long-term growth, they will hopefully call you out on it. This “call out” could even take the form of a PIP (personal improvement plan) — which might feel terrible to you in the moment— but trust me it’s one of the most effective wake-up calls for talented people who are stuck. I’ve seen it get people out of ruts and back on a stronger and more rewarding growth trajectory many times.
What to do (if you’re ready for a change)
TLDR: the ball is in your court to get unstuck if your job is too small.
Case 1: If you’re blocked, give it one more try, then shop the deal
Often, the fastest way to increase your role and scope is within your current company. So, even if you feel you’ve tried 5 times with no traction, give it one final try, and be very direct:
I’m excited about this team and the work we’re doing here. I’d like to take on more so I can continue to grow and increase my impact. I have a few ideas on how I might be able to do that. Is this a conversation we can have in the next two weeks?
If you get no response (or foot-dragging/hemming and hawing), it’s time to shop the deal. In this case, you are the deal. If you’re at a large company, it might make sense to look internally first (since internal transfers are usually faster and easier than an external job search).
Otherwise, it’s time to polish that resume, reconnect with your network and recruiters, and get on an active job search. I have posted extensively on how to job search effectively — check out the Debugging Your Job Search series, starting at TCW #010.
Case 2: If you’re coasting, reconnect with your Why
A ship without a captain can get lost at sea. And sadly, I see people in tech get lost in their careers all the time. Coasting can feel great in the moment — after all, you’re carving out more time for the fun parts of life: family, kids, friends, the great outdoors, etc — but it can lead to the eventual decay of your skills and value in the talent market, and even make it hard to get back into a career groove.
Tech moves fast, and if you’re not growing, your skill set is decaying — and you’ll find yourself struggling to compete in the future.
To regain your momentum and motivation, try reconnecting with your career values. What motivates you? When you used to be engaged in your work, what was your Why?
It doesn’t have to be world peace or mission/impact, by the way.
Three questions that might spark this exploration for you:
What year was the best year of your career? Break down what you liked about the work, the team, and your manager at the time.
Reminisce on your favorite work project ever. What made it your favorite?
When you feel most engaged in your work, what are you doing? Who are you with? Why is it so motivating to you?
Neither of these issues resonates?
If neither of the above situations applies to you, you may not have an urgent problem to solve, which is great. But there’s a big range between dysfunctional and optimized!
Let’s walk through what “great fit” looks like, since you might be in The In-between Space, and some tweaks can get you nestled into the career fit sweet spot.
Job just right: “I’m in a Groove”
This is where you want to be: flowing and growing.
What it feels like
You have a nice balance between knowing what to do (flow state) and challenging yourself to learn new skills (grow state).
~80% of the time, you’re in a state of flow, where you get lost in your work, lose track of time, and make meaningful progress.
~20% of the time, you’re researching, hypothesizing, trying out new things, problem solving, and growing your skills.
What it looks like (outsider’s perspective)
Your work product is timely and well executed
You’re engaged and creative with your work
You’re “always learning new things”
Co-workers seek you out for advice, new ideas, and your expertise
What to do (to stay optimized)
Staying in this state of balance requires a regular cadence of checking in with yourself.
Every 4-6 months, I run through this list of questions:
What new skills or capabilities have I gained since the last check-in? Do I predict these new skills growing in value in the job market over the next 5 years?
How has my average stress/anxiety level been in this period? Any anxiety dreams/sense of overwhelm/other signs of overload?
What was the composition of my average workday? How’s the balance between overhead (ie meetings), deep work/flow states, and exploration/learning?
How long was my average workday?
How many times did I work on nights or weekends? When it happened, was this planned or unplanned?
How is my outlook for my career in 10 years? Is it improved, flat, or worsened?
I’m a big believer in lazy systems, so if this checklist resonates with you, I highly suggest putting it into a calendar invite for yourself every 4-6 months. Here’s a handy checklist for you:
I guarantee you will reap tremendous professional benefits from checking in with yourself regularly, whether you’re in a great job fit right now, or not.
🎉 That’s a wrap! Give this job fit framework a try and let me know how it goes.
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