Collecting my hats

Reflections from working at an early-stage startup

Dear reader,

I left my job a few months ago! 

For the last 2+ years, I studied the craft of product building at Clay, helping grow a no-code spreadsheet into an increasingly popular lead generation tool. I joined a small team with around 10 customers and left a rambunctious group building for almost 1000 companies.

Working at a startup taught me a lot about human beings. To me, the job of a product person is one of translation and suggestion. Even at a tiny company, each person — customer, team member, founder — speaks a different language to express their unique needs. Doing meaningful product work requires positioning yourself at the center of the chorus to translate between parties and decode each person’s perspective. It also means doing the (often more difficult) work of understanding your own. As I write this, I find myself coming back to a quote from Babel, a novel I read last year about actual language translation:

“That’s just what translation is, I think. That’s all speaking is. Listening to the other and trying to see past your own biases to glimpse what they’re trying to say.”

During my initial months at Clay, I conducted hundreds of customer demos, learned to navigate our codebase, and took the liberty to ask my team all sorts of questions about themselves and our company. I started to synthesize this array of feedback as if it were a puzzle, extracting my own hypotheses about which problems were important for us to dig into as a company. I learned that articulating problems in an honest and compelling way could fuel the creativity of myself and my team. The problems identified became a source of truth against which to generate, prioritize and execute on our ideas. Achieving clarity on our goals became a mechanism to keep the team moving through the hard work and disagreements and very human emotions that are part of productive product building.

Me celebrating my ‘birthday’ (last day) with some very joyful Claymakers

Here are a few notable product insights I internalized over the last couple of years:

Product is about balance

The art of product (and perhaps life!) lies in discerning which mode of thinking to apply to make decisions in a given situation. I like to use the analogy of ‘thinking hats’ to remind myself of this. You can only have one hat on at a time, and hats usually come in complementary pairs, examples being:

The product hat where you wave your magic wand and design your dream feature vs the engineering hat where you evaluate what’s feasible to add to your current codebase

The dreamer hat where you think about your vision for your market (and the world!) vs the pragmatic hat where you act on what your market wants you to say or build right now

The fast hat where you ship fixes as quickly as possible vs the slow hat where you take the time to ponder ideal solutions

The big picture hat where you work to make connections between the parts of a system vs the siloed hat where you ignore what’s out of scope and focus on specifics

The instinct hat where you lean on your qualitative intuition vs the data-driven hat where you run tests and collect numbers

Hats take time to collect — sometimes you might not have the hat you need in your closet, or it might be too small or too weak for the task at hand. This is when it’s helpful to borrow from someone else. In other words, don’t be afraid to get help from people who are good at the types of thinking you’re not. And remember that no hat is superior to another — choosing between them is the balancing act.

Don’t worry about being too articulate too soon

If someone is thinking creatively, their initial thoughts on something aren’t going to sound amazing. The only things that foster perfect articulation are more time and information.

This observation should be applied two fold: don’t be afraid to sound stupid when you try to express an idea or observation for the first time, and don’t judge anyone else for sounding inarticulate the first time they express a thought. And as a product leader, don’t create a culture where people feel like their thoughts have to be polished before sharing them. Thoughts must be shared to be refined — good ideas don’t happen in a vacuum, at least not perfectly phrased ones! 

I find the inverse of this is generally also true. If an idea or thought sounds too perfect right off the bat, it’s likely not original or creative. 

Collective behavior follows familiar patterns

Economies evolve, technologies evolve, but people, communities, and societies tend to move in familiar waves. I came into my role with a strong intuition for the micro: inferring what individuals want. I think what ultimately helped level up my product thinking was sticking around long enough to observe the macro: how a customer base behaves over time. A couple of patterns that stuck out to me:

Words matter
The vocabulary you use across your product will be recycled by users as they communicate with coworkers, friends, and back to you. Successful word choice in your features, website positioning, and email copy is what convinces users of the value of your product and attracts more ideal customers. Finding the language that resonates is more art than science, requiring a combination of meeting customers where they’re at and observing how use of your tool shapes their thinking. Resonant language also changes over time as your market evolves – the use of your product should help fuel that evolution. 

Communities serve as knowledge bases
An active community around a tool isn’t just a powerful marketing lever, it also helps increase the value of your product. Community members help each other generate more value from your tool and give you visibility into which market insights and knowledge to document or productize. Sometimes you learn more from seeing your users interact with each other than from talking to them yourself. A great way to take advantage of this is by pushing users to communicate in public channels and fostering active engagement between them.

What’s next for me

Anyone who knows me well is aware that a common complaint of mine is that I am bored. To counter this, I try to feel so absorbed in my life that I have little to think about except the next person to meet, event to attend or decision to brood over. I achieved this sort of busyness in the latter half of 2023. Those six months of working and living were incredibly busy on both personal and professional fronts, but during that time, I didn’t feel the same inclinations to write and ponder and critique in the ways that feel characteristic to me.

In the last few months I’ve been attempting to embrace my boredom instead of escape it. I go on long walks, cook big batches of minestrone soup, watch movies from the Oscar noms, and visit the same coffeeshops again and again. I’m still complaining about being bored, but I’m starting to notice new thoughts and ideas spring up once more.

I have also continued my reading habit, picking up new books and essays and combing through hundreds of notes and bookmarks that I have accumulated over the last couple of years about topics like media ecosystems, learning on the internet, search engine design, and online advertising. As I synthesize these thoughts, I have noticed I keep returning to the same guiding questions. I’ll be spending the next chapter of my time exploring them — stay tuned to hear more.

If you enjoyed my writing, please subscribe! I’ll continue to share life reflections and post occasional updates on my explorations.

Talk soon,

Anita

As always, some music for your time ~ Kyle Chayka talks about the Youtube algorithm’s renewal of City pop in his new book, Filterworld. I made a playlist inspired by those vibes 🌃

Special thanks to the editorial team (group chat) who reviewed this piece — Kavitha for always being my first reader, Rayna for telling me when I lose the plot, and Megha for being the real Mad Hatter.