Intimate remote work

In Lookback, we’ve had the no­tion of be­ing able to work re­mote as a base­line since day one. Here are some of my thoughts on the deeper end of work­ing re­mote, on per­sonal lev­els.

This is from our jobs page:

We’ve cho­sen to build a dis­trib­uted team. We don’t want any­one to move be­cause of us. On the con­trary, we want to em­power peo­ple.

Where in the world are you the most pro­duc­tive and cre­ative? That’s where you should work from.

Working re­mote is a thing many (often smaller to medium sized) soft­ware com­pa­nies pick up these days — Basecamp (formerly 37signals) are huge fans, so huge they wrote a book on it. Companies sort of re­alise that all tal­ent nec­es­sar­ily don’t want to live in San Francisco, New York, Stockholm, or some other tech hub. At Lookback, we of­ten call it dis­trib­uted work, since it im­plies that there should be no cen­tral­ized of­fice where every­thing is or­ches­trated from (even though half of the team re­sides in San Francisco at the mo­ment).

Some friends of mine of­ten ask how we main­tain per­sonal re­la­tion­ships and keep a great work­flow in or­der to churn out high qual­ity work to­gether. I think these two things are tremen­dously im­por­tant:

  • Put in the en­ergy, tol­er­ance, and love, as in any re­la­tion­ship
  • Realise it’s a nev­erend­ing process
 ![](/assets/posts/lookback-cooking.jpg)  ![](/assets/posts/lookback-cooking-names.jpg)

From my own ex­pe­ri­ence, re­la­tion­ships de­mands a lot of en­ergy. Not in a bad way, just a lot of ded­i­ca­tion, will, and de­ter­mi­na­tion. Even non-ro­man­ti­cal ones, such as friend­ships, needs some love once in a while in or­der to main­tain that friendly bond you have with a per­son.

The same is with job re­la­tion­ships when work­ing re­mote. If a suc­cess­ful com­pany is to be built, where the em­ploy­ees cre­ate great prod­ucts, they need to be closer to each other than just a chat avatar in Slack. Your mileage may vary of course; some peo­ple don’t have this need. I’ve re­alised these things have worked well for us in Lookback:

Have phys­i­cal mee­tups

Obvious but eas­ily for­got­ten. So much fun, and can be re­ally pro­duc­tive! Eat food, hang out, talk about high level things as com­pany cul­ture, long term goals, soft sub­jects”. Last meetup, we had a typ­i­cal team build­ing ac­tiv­ity in­volv­ing cook­ing food to­gether at a restau­rant (we ac­tu­ally got to make our own sausages com­pletely how we wanted them). Then we dis­cussed re­ally deep per­sonal sub­jects, such as pri­or­i­ties, work­flows, and as­sump­tions. This was so fruit­ful, and brought us closer on a new level.

Have an Emotions chat room

One day, our CEO Jonatan cre­ated an Emotions chat chan­nel in Slack. It was for venting stuff”, which we had seen a pat­tern of peo­ple do­ing in var­i­ous other chan­nels. So this chan­nel’s pur­pose would solely be for ex­press­ing things like you would of­ten have at a phys­i­cal of­fice, per­haps 1-on-1 with a co-worker. Again, some peo­ple are in more need of this than oth­ers, but even if you’re not writ­ing in there your­self, just be­ing able to tune in oth­ers’ mood is re­ally help­ful in day to day work. For in­stance, if a co-worker has a hard time at home with the kids, he or she might be re­ally drained on en­ergy. That would­n’t be ex­posed any­where else in a team wide way if it’s not clearly com­mu­ni­cated in an Emotions chan­nel.

Having this room has given us the no­tion of that it’s okay to feel and ex­press your­self to your co-work­ers even if you’re re­mote. It’s a safe zone for good and bad moods. People around me can au­to­mat­i­cally ad­just to me if I ven­ti­late that I’ve had a re­ally bad week due to X, and have that in the back of their heads when they’re dis­cussing prod­uct fea­tures and plan­ning on Trello or what­ever.

Constantly tweak it

Remote work­flows are com­plex. Async com­mu­ni­ca­tion is great for some and hard for oth­ers. It de­mands un­der­stand­ing, tol­er­ance, and over-com­mu­ni­ca­tion.

We need to un­der­stand each oth­er’s way of work­ing, and one an­oth­er’s needs. One per­son might need more coach­ing and 1-on-1s, while an­other per­son com­mu­ni­cates like a nat­ural born re­mote worker on Trello/Slack/forums.

This needs to a con­stant cir­cle of al­ways-be-tweak­ing mind­set, where we never set­tly. Everybody should be able to voice their opin­ions about the re­mote work­flow in or­der to make it bet­ter, even by say­ing this thing X is­n’t work­ing out for me.

Example: we used Flowdock for chat­ting in the be­gin­ning. It’s a great chat plat­form: it has got every­thing Slack has with slightly dif­fer­ent UX. Our main thing was the use of threads. Instead of hav­ing every­thing in the same bucket (a chan­nel) peo­ple could start new threads to dis­cuss a sin­gle topic within a chan­nel (this might come to Slack soon, a bird tweeted in my ear). Anyhow, this was get­ting more com­plex to main­tain as the com­pany grew to twelve peo­ple, and we moved over to Slack just to ease the com­mu­ni­ca­tion for every­body in the team. We moved over to Discourse from GitHub Issues for our in­ter­nal fo­rum, since GitHub worked well in the­ory but was­n’t meant to be a fo­rum in the first place.


So easy to rea­son about but hard to pull off! It’s an art, prac­ticed in many con­texts: on Trello, in Slack, in the fo­rum. A rule of thumb I’ve got is to re­ally voice all rel­e­vant in­for­ma­tion I have in a cer­tain sit­u­a­tion. That is, bring up stuff like fu­ture block­ers, op­por­tu­ni­ties, fu­ture steps, and so on. If you work in dif­fer­ent time­zones, as we do, this is even more im­por­tant, since a day’s work might be slightly blocked or boosted just by your abil­ity to share in­for­ma­tion be­fore you go to bed and your co-work­ers con­tin­ues the joint work.

Repetitions are fine, since they pre­vent fu­ture mis­as­sump­tions. Have a sin­gle source of truth, whether it’s a doc­u­ment, Trello card, or fo­rum thread. And to me, few things beat face-to-face, syn­chro­nous voice chats. Talking with each other in voice brings out an­other layer of sub­tle com­mu­ni­ca­tion pat­terns, rather than speak­ing with each other in a text chat.

Have per­sonal ret­ro­spec­tives

We’ve got weekly ret­ro­spec­tives, where we rate these top­ics on a scale 1-10:

  • Happiness. Our gen­eral hap­pi­ness level dur­ing the week. Are we happy with life? Why/why not?
  • Restedness. Are we drained or tired? Why?
  • Productivity. Did we feel we achieved a lot dur­ing the week?
  • Team spirit. Did we have fruit­ful 1-on-1s, or some other break­through feel­ing of be­ing close to the team? Or just a gen­eral no­tion of hell yeah we’re the best?

We keep this in a Google Docs spread­sheet, and it’s com­pletely open to read each oth­er’s rat­ings and com­ments for any­body in the team. This is an­other, re­cur­ring layer on top of the more im­pul­sive Emotions chat chan­nel dis­cussed above.

I think much boils down to the no­tion of that in­di­vid­u­als that are close to each other can build bet­ter prod­ucts (beware, to­tally un-sci­en­tific the­ory). Yes, re­mote work de­mands en­ergy. Yes, re­mote work needs con­stant love, tin­ker­ing, and in­di­vid­ual ad­just­ments. It might not be for every­body. But when you achieve this cool equi­lib­rium re­mote work in dif­fer­ent time zones can bring, it’s pure bliss.