Howdy! Everybody has their own styles of working, and after you read this, you’ll know mine – what makes me tick, what makes me happy, and what we can both do to ensure a positive working relationship.

A typical day

I write in the mornings and do most of my meetings & client work in the afternoon. With limited one-off exceptions for time zone accommodation, I haven’t taken a morning meeting since 2013 in order to protect my writing practice.

I’m light on meetings because I perform deep work for a living, which needs spaciousness by design. I love it when meetings give us a clear sense of what to do next, resolving blockers & developing rapid consensus. I am not the kind of person who lives in meetings in order to hold space for psychic heat death. Instead, I rely on Slack & Trello to coordinate across the course of a work day.

Contemporary communication tools have many business benefits. They act as sources of truth that people can rely on to know what to do. They also allow for broader consensus, allowing those not in meetings (and future hires!) to be looped in.

Draft is open from 9a until 5p Central Time, Monday through Friday. When Draft closes, my home’s internet shuts off. I don’t keep work communications on my phone.

How I make decisions

I move with deep intention. I work on one thing at a time. When something has my attention, it has my full attention.

I think about the long term in just about everything. I think carefully about what will create durable, stable businesses, including both my own and those I work for.

I try to gather as much information as possible before deciding anything, and I often make decisions that represent halfway points between multiple stakeholders. Fairness is a good word to keep in mind when thinking about how I settle tactical decisions, as is the sentence “a good compromise makes everyone mad.”

How I think through problems

I think in systems. There are always reasons for the things that happen in technology, and usually those reasons are rooted in tradition or messy human-ness, both of which take time to understand & address.

When there’s something intractable happening, I tend to play the long game. There are a million battles to fight at any point, and I think the path to success involves knowing which ones are worth handling at any point. Sometimes you need to get some quick wins before you handle the big stuff, for example, or you need to ask bigger questions about why a thing is happening.

How I like to share information

I’m a writer by nature. When I’m sharing new strategic or research work, I prefer to do so in the form of a written report, or in the form of written cards on Trello or Slack.

This guide is an example of the sort of work I do. I write for readers. I expect people to read my writing. You are paying, in large part, for my writing.

I present new design work on calls, walking everyone through a comp and pausing for questions. Reactions are less great during this period, because they tend to be rooted in personal preference and less oriented around the strategic direction we want to be taking.

How I like to receive information

In text, ideally, over Trello or Slack. Calls are nice for talking through blockers & resolving conflict, but if we have to wait a long time for our next call, text it is.

The type of teammate I aspire to be

I want to view myself as a trusted resource, a representative of how we research & understand the customer.

I know things are going well when people ask me complex questions about customer behavior, and I’m able to either answer them definitively or provide an evidence-based guess that synthesizes what we’ve already done.

What makes me excited

I cherish curiosity. We never have all of the answers, do we? And there is no substitute for doing the necessary work to understand & address them. Nothing lights me up more than when I find something new & baffling, because then I have the opportunity to figure it out. I find so much human richness to this sort of work, even if at times it feels hopeless & upsetting.

How I blow off steam

I bike in the city of Chicago. Nothing more dangerous or upsetting will happen to me in any given day. You cannot hurt me in a way that matters.

How I handle conflict

Immediately and on a video call, if at all possible.

Conflict gets a bum rap. It is how consensus is developed among many perspectives. It is how surprises are addressed. It is how ambiguity is clarified.

We will be in conflict at some point, even if neither of us calls it that. I will point out the sticking issue, explain how I felt as a result of the issue appearing, resolve any confusion, and work out next steps.

Situations I thrive in

I work best within calm companies on the slow web, for those who know how to take care of both themselves & each other.

I thrive in any situation where the team has a mutual curiosity. I love questions. I love asking questions, and I love your questions even more. If something unexpected is happening or you’re uncertain about why I’ve done something, it’s a good idea to ask. I’ll try to do the same.

I love work environments where management exists to serve their workers, not the other way around. I especially love environments where work is co-created together with an open mind.

If you arrive to our work together sitting on the same side of the table, with a pile of wild & impossible problems in front of both of us, and treat me as your equal, I will come away nourished & happy.

Situations I do poorly in

I work in the tech industry, which historically loves disrespecting the boundaries of its workers. As a result, I have lots of clear boundaries that I’ve cultivated in order to do the best possible work for you.

I don’t do my best work when decisions are poorly explained, made on phone calls without broader consensus, ungrounded in evidence, or rammed through by fiat. I also don’t do end-runs, internecine fighting, burnout culture, or ghosting.

There is a real human on the other side of your video calls. I invite you to treat them like you’d want to be treated.

How I delegate

I have an assistant. My delegation process for them is fourfold:

1. I do the work.
2. I write up a procedure for them to do the work.
3. I observe them following the procedure, and provide feedback & updates to the procedure.
4. I let them do the thing.

I am fairly hands-off once we get to step 4.

What I think I’m great at

I’m really good at talking with customers, prioritizing design decisions, and analyzing A/B tests, clearly. I can bugfix a prototype. I can tell you why our experimentation framework is misbehaving. I can read the heat maps that you set & ignored for a year, and I can help you make money from them. Ditto behavior recordings. I have 20 years’ experience with running usability tests. I can herd cats and resolve blockers with the best of ‘em.

But I’m also good at understanding the more relational side of doing tech. We are all feral meat sacks at the end of the day, and it’s our job to figure out how we can take care of each other and move things forward.

What I’m less great at

I can code, but you probably don’t want to pay me to write production-grade code.

I’m not so great at producing video.

I like to look at analytics for research purposes, but if you think “research” involves my answering a lot of questions about why your ad campaigns aren’t performing, you’re perhaps missing the point of both research and why you’ve hired me. I’m not a dashboard bro, and tend to default to the softer, qualitative, story-based sides of the work. After all, humans always exist behind the data, and I’ve found them to be quite irrational animals.

How to praise me

Working alone is hard because I don’t get enough positive feedback at my job, full stop. I’ve run A/B tests that have generated tens of millions and nobody has thanked me for them. I end Zoom calls and always wonder how people feel.

Please don’t forget to let me know when I’ve presented something cool, run a cool experiment, or gotten a big win for the team. Even just a brief Slack DM is great. It takes only a few minutes and you’ll make my month. Emoji reacts go farther than you know, too, even though I personally don’t use them.

How to deliver constructive feedback to me

Ideally, ask questions about my thinking first, and then hit me with the “yes/no/yes”: say something good first, then the feedback, then something hopeful & positive.

For example, “I love what you did with X, but Y needs to fulfill our goals in Z way. I think maybe A will be a good way forward instead?”

Hooray

And that should be it! Thanks for reading, and let me know if you have any questions – I’m happy to clarify anything.

Thanks also to my pal Val Geisler for the format, which was my starting point for this.

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