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Finding Person-Problem Fit

22min read

Author: Brie Wolfson

“The best color in the whole world is the one that looks good on you.”–Coco Chanel

When investors are looking to make bets on companies, they look for product-market fit. I think we can and should use that same framework to make bets on talent. That same magical spark that ignites when a company finds their perfect place in the market happens when a person finds the right problem to work on. Let’s call it person-problem fit. And let’s talk about how to find it. 

Because if we’re going to have the dynamite careers we aspire to, and be rewarded accordingly, it’s going to start with figuring out what holes are you-shaped. I’ve heard this described before as “playing the right game,” or “climbing the right ladder,” but I think it’s about more than that. I think it’s about finding the things that light you up inside so much that you can’t help but dive in and do things you are wildly proud of. It’s about the thing at the tippy top of Maslow’s hierarchy of needs that many of us spend our whole lives searching for: self-actualization. The sooner you find them the better it all compounds. And no one else but you—not your manager, not your partner, not your parents, not your performance review—is going to be able to do this work for you. 

The ultimate goal is, of course, to find the work that taps into the best of what you have to offer. There’s no shortage of company OKRs or open roles in your LinkedIn feed or issues in Linear that need an owner or hats to wear or shoes to fill. The first step towards picking the right one for you, and you alone, is to look inward at what you’re working with. 

Here are some exercises you can rely on to help you build that self-awareness. 

We’ll start off by looking at tactics for collecting data from your environment as you work to give you the real, fact-based truth, about what you’re great at (which, by the way, won’t always align with the narrative you’ve spun in your head about what you’re great at). Some you’ll be able to tackle solo and others will engage your broader community in sharing feedback. Then, we’ll explore a few artifacts you can create based on what you’ve learned that will help you become a magnet for the kind of work that will make you shine.

Think of this like a menu. No need to bite off too much at once (the eyes are always bigger than the stomach, aren’t they?). Start with the stuff that immediately resonates.

Data Collection

One of the trickiest things about understanding ourselves is that the way we see ourselves is all tangled up in what we admire in others, and what our colleagues deem the “cool team,” and what our company leaders tell us is the highest priority thing to work on today, what our parents wanted us to be when we grew up, and all sorts of other stuff. These are interesting inputs, but ultimately they are distortions of reality bent in the direction of our own (often unconscious and involuntary) biases and judgments. We can create some pretty captivating stories about ourselves, but that may or may not be reflective of the reality of how we actually show up in the workplace. 

So, I like to frame this type of self-inquiry as “data collection.” The exercises are designed to help you detach from that tangly mess of biased judgments in your mind (and gut), and look at the facts. As you work through these exercises, think about yourself as a scientist running an experiment in which you are your own subject. 

Data collection: logging while you work

I’m a big, BIG fan of logs. In computer land, a log is a file that contains a record of events. Teams (often observability teams) set these up because they provide a ground-level account of what’s going on at all times. (These come in especially handy when things inevitably start to go awry). You see where I’m going with this, don’t you?

Having this data recorded and stored will help you tease out patterns and trends (sometimes unexpected!) from the in-the-weeds, day-to-day, goings-on of your work life. 

To set up a log, just open up a blank document. Then, just drop things into this doc as you go, as often as you can. The only consideration is what format you’re going to be most comfortable in. Pick one tool and stick to it. You want as much information as possible in one place when the time comes to do your learning. 

A quick interlude about tools:

For most of my logs, I like using a pretty bare-bones text editor with great search functionality and low barrier to get something in there. Google Docs is my personal go-to. I like to be able to open a new tab and dump stuff into the doc without much fuss (FYI typing docs.new into your browser will open up a new doc for you if you’re logged in). I’ll rely on search when it’s time to look things up later. 

If there’s a visual component, particularly screenshots, quotes, or other bits and bobs I collect from across the internet, I turn to Are.na. If I want to have something more free-form, especially if I’m sketching a visual for an idea, I’ll use Figma. Notion is another popular option for this kind of idea capture. 

Other self-proclaimed loggers I know turn to products with more robust tagging functionality. I wish I was disciplined enough to do the tagging up front because it makes the “data analysis” a lot easier later. My favorite product for this use-case is Reflect. To me, it strikes the right balance of easy-to-add-things to and allows you to cut by day or by tag when you want it. Roam Research is another option (though I’ve found this a little less user-friendly for my very basic use case). If this sounds like a system you’d be able to uphold, I’d say do this! But, for a lazy logger like me, the combination of having to open yet another tool and the pressure to tag just deters me from adding anything.

Now, back to those logs. Here are a few different flavors to consider. You can also combine many of these into a single log (I do!). 

Scrapbook of Things I’m Proud Of

This is exactly what it sounds like; a collection of things you’re proud of—things that make you smile (maybe even blush a little bit) or want to write home and say “look at how awesome things are going!” It can be a thing you worked on, feedback you’ve received, or someone posting about something you did. 

Snag Log

This has similar properties of the Scrapbook of Things I’m Proud Of, but the snag log covers the things that bog you down or draw your energy—things that make your tummy turn or sink down in your chair or have to close your laptop and take a breather. A friend once framed this as an “ick list” (and to be totally honest, it was about her ex-boyfriend she was trying to get over). To quote myself in that First Round Review piece, things that have appeared in my ickies list include: still can’t get this query to run and weekly standup bores me to tears, and welp, that launch was totally lackluster. Waste of time? It might feel embarrassing or silly at the moment it’s happening, but it’s data you can use to get more productive or find more joy in your work.”

Note: I wrote about these first two types of logs recently for First Round Review. I’ll beat the drum about these tactics as much as I can because they have been massively impactful in my life and career!

Interoception Log

Interoception refers to the sense of the internal state of the human body. I first learned about this term from my psychiatrist and first encountered the idea of an interoception log in Annie Murphy Paul’s book, The Extended Mind. The book’s thesis is that our body holds more clues than we might expect to interpret our environments, and as a result, advocates for listening to our bodies more. 

I’d self-identify as a person that is willing to lean on her intuitions, but if you’re skeptical about “trusting your gut,” get this. The book cites a study called the Iowa gambling task that totally blew my mind. The task works by presenting participants with four virtual card decks, containing cards that will either earn them money or take it away. The goal is to win as much money as possible. Unbeknownst to the participants, two decks are “bad decks” (more likely to take money away) and two decks are “good decks” (more likely to win you money). The consistent finding is that participants will gravitate towards the “good decks” without consciously knowing they’re doing it.  Even hovering over bad decks will elicit a stress reaction (like skin surface temperature rising). Wild!  

Your interoception log should take stock of any big feelings, and what’s happening when those big feelings occur. If you’re anything like me, coming up with words to describe feelings can be a challenge so if you’re in the same boat, here’s “The Feelings Wheel,” created by Dr. Gloria Wilcox to help.  

Image source: AllTheFeelz App


Whenever that :starstruck: feeling strikes, record it—products, people, quotes, spaces, books, art, recipes, etc. If you don’t know where to start, maybe your company has an inspiration channel in Slack that you can pick some favorites from? Alternatively, the Are.na explore tag is full of rabbit holes to tumble down. And, if nothing’s tickling you there, ask some colleagues you admire what blogs, newsletters, or Twitter accounts they follow. Your taste will reveal itself over time, promise! You just gotta get in there.

Over time, I’ve riffed on this concept a bit, and now maintain a list of things, created by others, that I wish I created. (At the risk of giving you too much of a glimpse into my brain) things on my list include: The Empathy Exams (book), The Marginalian (FKA Brainpickings, blog), We Feel Fine (art/tech), and this episode of Invisibilia (podcast). As you can tell, what lands on here has very little to do with what I have the skills to create myself, and more to do with the things that speak to some combination of my tastes, outlook, interests, and medium.

Magnet Board

What do people come to you for? What are your colleagues constantly asking for your advice or input on? What do your company leaders DM you about? (The less these are the things squarely in your Job Description, the better). 

For me, I noticed people were always coming for me to edit their writing. And, a key piece of editing well was predicting how the information would be received by its audience. Often this was blog posts or marketing page copy, but the stuff that would really light me up was the stuff getting shared with other Stripes (All Hands presentations, shipped emails, product requirement docs). As I got deeper into the world of editing internal docs, I increasingly found myself looped into matters of internal communication. Noted.

Fires I Run Towards

Fires are scary! The natural reaction is to run away from them. Most people do. But, there’s always that rare flavor of problem that makes you want to sprint right towards it. 

I know I’ve found one when people are treating something like a hot potato but for some reason, when it falls into my hands, it doesn’t seem all that hot. During my time on Stripe’s BizOps team, I found this happening all the time. When projects like company planning or integrating newly-acquired companies or developing content for our all-employee conference came up, I would be the only one to raise my hand (and I did it with gusto/was surprised no one else wanted to work on them!). On the other hand, when projects like identifying new markets, running go-to-market strategy for a new product, or inflecting product adoption with new onboarding flows came up, I averted my eyes so I wouldn’t get called on while others were very quick to volunteer themselves. 

Now that I’m 18-months into consulting startups on their company culture, I can see how these moments in our BizOps staffing meetings were early clues that I was into something others weren’t. And, the space was wide open for me to do something with. Isn’t that interesting?! 

Maybe your lightbulb moment isn’t quite so glaring, but I bet if you looked closer, and turned over a few rocks, something like this is unfolding right before your eyes.

Data collection: personal working session

To complement your logs (or to replace them, if constant logging sounds unfun/overwhelming), give these exercises a try. Doing a great job on these will require some time and space for honest self-reflection, so I’d recommend blocking the time and shutting down email/phone/Slack while you do it. 

I’ve found switching my physical space makes it easier to switch into a new mental space. So, if you’re so inclined, consider taking yourself to a coffee shop or a different room in your house or a park nearby with a pen and paper to dive in.

In all of these exercises, get as specific as possible. Stick through the lulls. The ideas will probably come in waves, and you don’t want to miss out on key insights because of your own impatience (or the siren call of your inbox). Plus, at least in my own experience, that’s when the nuance really starts to reveal itself.

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Energy assessment

The goal of this exercise is to articulate what gives you energy and what draws it down in your work. I know the approach seems relatively straightforward, but I think you’ll find it’s harder than you think it’s going to be to tease things out (and rank them against each other). 

If you’re stuck, start with what’s listed on your job description, what’s on your to-do list for the day or week, what’s on your calendar, or the stuff that you’re the assigned owner for. Then, let it flow. Nothing is too small. It’s all rich data. 

Another option (that I learned about from Compound founder, Jordan Gonen, who was inspired by Opendoor co-founder, JD Ross), is to print out your calendar for a few weeks and “highlight everything that gives you energy in green and everything that takes away energy in red.” This will give you a pretty good sense of not only the qualities of the work that fuels vs drains you, but also a sense of what the overall composition of your work environment looks like.

Rooms you want to be in

In short, work you want to have more exposure to. List them out. And don’t let your imposter syndrome get in the way. You’re allowed to want more exposure to something even if you don’t know how you could directly contribute right this minute. And, you’re allowed to ask to peek around corners or fly-on-the-wall for conversations about topics you’re interested in. 

Also remember that the people in those rooms are also allowed to say no. It’s all okay. 

Expressing curiosity is attractive. It often bears its fruits over the long term. Getting in the game usually starts with getting your gear on, going to practice, and hanging out on the sidelines for a while. 

Your teachers, role models, and villians

How we respond to others says a lot about what we value. And, it’s probably about time for a break from all that inward focus. In this exercise, make a list of teachers, role models, and villains and then journal for a bit on what it is about them that elicits the outsized reaction in you.

When it comes to your teachers and mentors, consider what they taught you and why you think their teaching style allowed you to learn so well from then.

When it comes to your role models, consider what about their work or their approach to it, is so appealing to you? And since no one is perfect, what would you change if you could?

When it comes to your villians, consider what exactly grinds your gears. What about the way they do what they do doesn’t appeal or impress? And, if we assume that they must be effective in some respect or context (that’s why they were hired to your awesome company!), what do you think you’re overlooking or not valuing that others do? Why is that?

Career Decisions Matrix

Another exercise that is simple in approach, but the good kind of challenging to fill out. 

Create a table where the columns are roles you’ve had and the rows are things you value in your work. Below is a screenshot of mine to give you a sense of how this could look and work. 

Then, weight each value. I like listing these in groups to not only stay organized, but also to ensure that I’m not over or underweighting any set of factors. To gut-check the weights, compare a few groupings or factors. Looking at my matrix, mentorship and learning is ranked highest, and 2x as important as lifestyle and flexibility. Checks out.

Then, color code or score each role to see how they stack up. You’ll probably find this exercise loops a bit–as in, your list of values and their weights will probably evolve as you reflect further on past work and sink deeper into the exercise. It’s also possible that you become aware of the ways in which your weighting scheme has changed over time. Take note of it all. Let it flow.

Data collection: asking your colleagues

Your colleagues—those you work with closely and those who observe you from afar—can be an incredibly rich source of data. The key to getting good information here is to create an environment where they can give you good information. 

This is where I think performance reviews, even though they’re executed with the best intentions, are unfortunately very ineffective—they’re just too loaded and situated in a context of weird incentives. When you turn to your colleagues for feedback, make sure you have your scientist hat on. Make requests from a place of open-mindedness and earnestness, and communicate that with not only your words, but also the format for delivering that feedback. A few ideas for how to do that.

Core sampling

Ping 20 people and ask them to tell you what you’re great at. (20 is kind of a random number, but you’re a scientist and you need to get that sample size up!). Aim for a diverse set of respondents—people close to you and your work, people further away, people in roles like and unlike yours, people higher and lower on your ladder, people with styles and unlike like yours, people with similar and different experiences or backgrounds than yours.

So you don’t come off like a total egoist, be open about the fact that you are doing an exercise to learn more about the places and ways in which you spike so that you can be more productive and satisfied at work. Remind them to be honest. Thank them for taking the time to do it. And, give them an out (that doesn’t require an explanation) in case they can’t or don’t want to for any reason right now. 

Treat close colleagues to dinner and ask them to tell you what they think you’re great at

For the people who you really want to dig in with, ask if they’d be willing to carve out more intimate time, outside of the office (YOUR TREAT!!), to have this conversation with you. Maybe you even want to give them a price range and let them pick the restaurant? Remember, they are doing you a favor, even if you are paying, so definitely make sure it’s at a time and location that is convenient for them.

If you have any specific questions or topics that you think it would be helpful to explore with this person in particular, do yourself a favor and send them in advance. Even if they aren’t going to formally prepare, you’ll probably get the gears going. 

I did this once and it changed my life. No exaggeration. 

Ask someone who has worked closely with you to write a mock recommendation for an academic program you’re interested in (real or fake)

This definitely places more of the time/energy burden on your colleague, but they might prefer an option for something async and this format is more fun than a typical performance review. Also, it’s a pretty cool way to create an artifact around this that you can (both) look back at in the future. Since this might be relatively time-intensive, I’d leave the timeline open for this. 

I wrote one once for a dear colleague and friend, and it was honestly so much fun to spend some time gushing. 

Producing Artifacts of Your Learnings

Now that you have all this data, what to do with it? 

The first thing to do is just review it. Clear some time on your calendar to sit with this amalgam of data you’ve collected and simply sift through it. I think you’ll get a kick out of what you see. Your logs will be little time capsules of things that feel far away in the rearview mirror by now. Your personal working sessions will reveal just how thoughtful and self-aware you already are. And the kind things your colleagues said about you will warm your heart. 

Some clear themes will reveal themself immediately. Even more themes will emerge with a little more time metabolizing. You’ll pat yourself on the back for spending the time to learn all this stuff about yourself. And you’ll have more constitution about these things you kind of knew about yourself all along and now have the data to back up.

And once you’re done reveling in your new-found self-awareness (and please do enjoy that for as long as you feel like), it’s a good idea to establish some artifacts around those and then put them in a place where others can find them. Because that’s how to get the magic of matching your talents and inclinations to the stuff those around you need more hands and minds on to really happen. 

Working with me

Jay Desai first conceived of this concept (he called it a ‘user guide’) and I first learned about it when I read Claire Hughes Johnson’s, former COO of Stripe. At its core, this document is a way to express and scale your preferred working style and preferences. (This one also features in my First Round Review piece if you want to read more).

The goal or expectation shouldn’t be that someone else bends their working style to yours. Instead, it should be used as a tool for someone else to understand you better. As I mention in that piece, I’ve also leaned on “working with me” documents in situations when something’s not quite clicking with a colleague and you’re not sure why. Creating and then comparing documents has been immensely helpful in spotting unexpected points of alignment or misalignment that can lead to moments of deeper connection and teasing out root causes of work friction.

Here’s a link to mine! And a screenshot of what it looks like here.

Brag document

This is the curated and edited version of your “what I’m proud of log” that is appropriate for “public” consumption. Julia Evans does a fantastic job of not only describing the virtues and impact of these documents, but also provides fantastic guidance on how to create your own on her blog here. This is especially useful around performance review time! 

In her words, 

“There’s this idea that, if you do great work at your job, people will (or should!) automatically recognize that work and reward you for it with promotions / increased pay. In practice, it’s often more complicated than that – some kinds of important work are more visible/memorable than others. It’s frustrating to have done something really important and later realize that you didn’t get rewarded for it just because the people making the decision didn’t understand or remember what you did. So I want to talk about a tactic that I and lots of people I work with have used!”

A quick summary of her tips (again quoted word for word because Julia is a master at this stuff):

  • Explain the big picture
  • Don’t forget to include the fuzzy work
  • Write a document listing your accomplishments

Remember, by showing people what you’re proud of, you’re also implicitly clueing them into the stuff you want to do more of. If there are gaps between what you’re proud of and what you want to do more of, share that, too!

Your career action plan

This is a tactic I borrowed from Stripe who is doing some incredible programmatic work around talent development. One core principle of their development philosophy is that career planning should originate from the individual, not the manager.  Managers will, of course, relentlessly support their team members in clarifying and achieving their career goals, but it is ultimately up to the individual to drive the conversation (when they're ready) and clarify what they want. I like this approach for many reasons, one of which is that it’s rooted in individuality and self-awareness vs. the prescriptions and structures of organizations. 

This very simple template will help you articulate your goals and identify any gaps between where you are and where you want to be. Then, it makes room for you to translate those gaps into a proposed action plan for closing them. This process makes it much, much easier for those around you to plug in and help. Win, win, win!!

Your aspirational resume

Write a resume for a job you want in 5, 10, or 20 years from now. Stay in the creative, imaginative, ambitious space. Maybe that job doesn't exist yet. Maybe you don’t have the skills to do it yet. Maybe no one does. Write it down anyway. Do it in the real format of the job description for full effect. It’s more fun and it will help you actually visualize what it would look like.

A prior colleague one told me a story of stumbling across a job description for his dream job. The only problem was it required him to be fluent in Japanese. You guessed it. He got fluent. 

Knowing where you want to go is a good step towards getting there. 

Sharing them out

Once your docs are in a good place, it’s time to put the word out. If a tree falls in the forest…etc. Think of it like a bat signal—you want to project the best of you out up into the sky so that anyone who needs you knows you’re around. 

Your options are:

  • Send them directly to others who you think would care (your manager is probably a good start)
  • Post them into public spaces (so those in the outer valences of your orbit can be aware of them too)

Don’t be shy! Do it! Do it now!

The time is now

I collected and designed these exercises to be snackable and fun, but I know that the pursuit of self-awareness can be a scary and challenging task that strikes some deep chords. But I can say from experience, it’s worth it. It’s the place that’s filled with thoughts like “I can’t believe I get paid to do this?” 

And it’s within your reach. 

So, I’ll say it again. Don’t be shy! Do it! Do it all now!