Rewrite The Docs at ATO 2019

solidarityforever

If you’re here because you saw my talk at All Things Open 2019, thank you!! If you are here just because, thank you too! 🙂 The original blogpost that my talk was based on is here and below are links to some of the organizations I mentioned. The ones that accept donations are indicated with a $ sign:

Solidarity!

Gratitude: August 2019

Before the month is out, I just want to share a few things that gave me life as of late.

The Last Black Man In San Francisco

This movie was stunningly beautiful. When I saw the trailer I thought it was going to be sort of the same thing as Barry Jenkins’ Medicine for Melancholy but it was more like Atlanta if Atlanta was replaced by San Francisco. It was eerie but exciting to see streets I walk so very often these days through the eyes of “natives”. Spoiler alert: It’s not just about San Francisco 😉

Tiny Desk Concerts: Lizzo and Jeremy Dutcher

Two of my faves recently had TDCs. So queer, so visually engaging, such music to my ears. What is it about that damn tiny desk that conjurs such sweet magic?

Me! on No Manifestos Podcast

Audio-Technica-AT2020-USB-Podcasting-Mic.jpg

I had a really fantastic conversation with my old coworker Stuart Sierra about tech and activism and other things for his new podcast No Manifestos. I am super pleased with how it turned out! Please do listen.

A Few Things to Consider Before Becoming A Remote-Friendly Company

A few years ago when I was at Clubhouse I blogged about our process of becoming a geographically distributed team. In that case, the first stumblings towards global domination were not made to acquire talent but rather in an attempt to retain talent vital to our team (talent = people we really loved working with and didn’t wanna lose!). In that article, I outlined some of the ways we tried to bridge the gap and some of the things that were still just tough.

I’ve also written about some of the reservations I have about working from home, especially as it pertains to underrepresented people in the workplace.

Since moving to Nylas and serving on the top-notch leadership team here, I’ve been even more privy to some of the business-side challenges of having a team where people are working from all over the place. SO I thought I’d pull together a quick blogpost of my learnings.

Things to Consider Before Opening Up Satellite Offices or Having Remote Teammates

People In Other Places Are Often In Other Timezones Too

I know it sounds obvious, but it needs to be stated. If you employ someone somewhere else, their day may overlap with yours a lot, a little, or not at all. You need to think about how that’s going to affect everyone’s ability to get things done. If your SF-based team is making most of your decisions synchronously in meetings or Slack, how will that affect your support folks in Berlin, your UX designer in Medellin, or your developer in New Zealand? Will they have to work odd hours just to keep up with HQ or can you start relying more on async tools?

When working across large distances across the globe, it is important to establish a baseline in every area for when they should be online and working and when they should stop and go live their lives. While you might sometimes need a teammate to work before or after their formal working hours, it is useful to know, clearly define in the calendar, and respect those agreed-upon working hours.

If you’re going to be working across significant time differences, I recommend trying to move meetings to times that work better for people and leaning more heavily on tools like Clubhouse and email that allow people to communicate on a more humane timeline.

Flights and Hotels Are Expensive

Cohesion across teams does require some amount of time spent together in fleshspace. Getting people together often means flights, hotels, and expensed meals. Just make sure you have the money for this — and that you earmark it especially for those purposes.

A/V Is An Investment…Good A/V Even More So

I am of the opinion that videochat software is painfully immature and being relied on too heavily for important communication. I use videochat every single working day and it is very much in the “can you hear me now?” phase. This is unfortunate because around the world in so many contexts people rely on it to make crucial decisions (read how Skype Trial has tragically become the norm for US immigration court).

Despite videoconferencing’s weakness as a replacement for “the real thing”, it is what we got. So doubling down to make it work is important. Headphones, good mics, fast wifi, and good webcams can cut down the distance between co-workers and enable you to have vital conversations with less muffle, crackle, and static.

When these all fail you — as they inevitably will — try to keep your teammate’s phone number nearby and just call them on the phone. I’ve had so many hours wasted fighting with videochat. Don’t let that be you and your team.

Employing People In Other States and Countries Can Be Costly and Time-Consuming

Different states and countries have different employment regimes. If you intend to employ people there, you will need to be in compliance with those requirements. HR companies like Gusto can likely help you with red tape, but it will still require some time and money to make sure you are following the rules of (and engaging the insurance market of!) the state or country where your fantastic new potential teammate lives.

Benefits Can Be Lopsided

If your company offers special perks to people in the office, you’ll need to carefully consider which of those you can/want to extend to people working from home or a satellite office. Things like free lunches and free office massages or whatever are often there to entice people to come in to the office and stay there. They tend not to be as feasible to make available to people who are working from home.

It is important to think about offering a benefits regime that doesn’t cause lopsidedness or ill-will when your HQ folks and your remote folks compare their cards.

None of this is intended to discourage you from doing what you need to do to attract and retain great people for your company. The last 10 years of my career have been spent working in organizations and teams that span state and national borders, and I’ve rarely had to rule someone out because of their location.

Remote workers do work; geographically-distributed teams can and do work—even on a small scale. They just work best when you go in with your eyes open to the challenges.

My DEI Sniff Test

I recently started a fantastic and challenging new job, but before I got here I spent 6 long months carefully job hunting.

At this point in my career, I have afforded myself the right to be a lot more picky about where and with whom I work since I spend more waking hours with coworkers (and customers!) than I do with my family.

For most of my professional career I’ve been the “Lonely Only” along several axes, and I didn’t want that anymore. I didn’t want to have to be the sole representative of diversity anymore or feel burdened with the task of rifling through my LinkedIn to fill the pipeline with underindexed folks.

So, I took a more studied approach to job hunting. Rather than just relying on “warm intros” from white male friends, I struck out and did a lot of my own research and quickly developed a “diversity sniff test” that. I hoped this tweaked approach might prevent me getting into some of the same messes I’d been in before. So, what’d I do? Well here’s a few things.

1. I checked the picture on the team page

I know team pictures can be outdated and misleading, but a quick scan for people of color on the team page can at least give you a sense of whether the company has made any effort to show that they care enough to at least try to show that people of color are welcome there. For whatever it’s worth, Teachable’s Careers page was one that stuck out in my mind as making me feel like I’d be comfortable there.

2. I looked into who was actually in leadership.mostlywhiteguys
A careers page can only tell you so much. I’ve definitely worked at places where they purposely position the women and POC in front during picture time to make them jump out in the picture even though few were in leadership roles. Finding out who is actually in charge around there sometimes requires sniffing around on site like LinkedIn and Crunchbase. Once you know who they are, you might peek at their Twitter to get a sense of what actually matters to them .

3. I looked at what they sponsored.

nylasdiCompanies that truly care about DEI should be going beyond hire a few brown faces and be giving money and time to groups and events that want to disrupt the ratio. This can be a cover up too (one need look at all the noxious corporate pride stuff), but it gives you a little signal that they are trying to exhibit some amount of virtue or what Prof Scott Galloway from Pivot podcast cynically calls “Woke As A Business Strategy“.

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I am not saying my current company perfectly ticked all my boxes. None of this sniffing is foolproof, but this research — coupled with working my diverse network to ask several pointed questions of the whispernet— did yield a better result than in the past.

How about you? How do you sniff out companies that share your values? Drop me a line and let me know!

Gratitude: May 2019

Before the month ends, I am just sliding in here to share a few things that gave me life this month.

Cillian Murphy’s Playlist on BBCRadio 6 Music

I completely live for Cillian Murphy. For the past few months, he has been covering for Guy Garvey (of Elbow) on BBC Radio 6 Music. I like ALL the music Cillian plays, and when he plays and waxes poetic about artists I already know and love, it just deepens my overwhelming love for him. He was just in NYC for a theater run and I sadly missed despite my best efforts. One day, Cillian. One day…

Thanks for the Feedback by Douglas Stone and Sheila Heen


This book holds the solution to many of the world’s problems. Nearly all feedback is a gift. We just need to learn how to mine it for the gems.

Fontaines DC


I learned about this band via Cillian Murphy and his aforementioned radio show. They are so Irish and wonderful. Their NYC show is sadly already sold out.

Gratitude: April 2019

Here are some things I was grateful for last month. I meant to post this last month, but I started a new job and the month zipped by! 

New job!
I am now the Head of Customer Success at Nylas! I couldn’t ask for a better group of folks to work with and the trips back and forth to SF have been fruitful and illuminating. I am exceedingly grateful for all the outpouring of support and sighs of relief from my loved ones . It was a tough slog.

Juanita on Netflix

I love Alfre Woodard. I love Adam Beach. I love Alfre Woodard and Adam Beach together. This movie made me smile from start to finish. Will watch again.

Food!
belotti
During one of my many recent trips to the Bay Area, I had occasion to have several great meals. Two of the best were at Japanese restaurant Rintaro and Italian restaurant Beloti. If you go to Belotti, definitely get the broccoli!

Minding The Gap

This Oscar-nominated (not that that matters, but still) documentary about a group of skate friends coming of age in middle America completely broke my heart and is the best movie I’ve seen thus far this year.

Gratitude: January 2019

Just sharing one of the things that lifted my spirits this month….

jeremy-dutcher-wolastoqiyik-lintuwakonawa-album-artwork-1200x1200
Jeremy Dutcher is a classically-trained queer Canadian Indigenous tenor, composer, musicologist, performer and activist. He is a member of the Wolastoqiyik (Maliseet) member of the Tobique First Nation in North-West New Brunswick, and after doing a research project exploring old wax cylinder recordings of Maliseet songs that were no longer known to the young people (due to being banned by the government by way of the Indian Act), he decided to revive them in post-classical arrangements for a contemporary audience. The result of this 5-year project is his album Wolastoqiyik Lintuwakonawa. I seriously can’t stop listening to this. I love him, his gorgeous voice, the whole project. More of this. YES.