29 June 2018

Week 3-4: Progression

Posting on a Friday this week, it’s been hella busy, after last week off. May stick to Fridays for now, always a good time for a retro.

Look at those tomatoes. Credit: my wife

The Skinny

I’m gonna tell you what I’m working on…

There’s always something magical about floating around in a (watermelon themed) rubber ring in a swimming pool in Southern Italy. Clears the mind.

Inspiration doesn’t gradually grow during downtime, it hits you suddenly. Having spent most of the week not thinking about work (I finished His Dark Materials trilogy and ate a lot of Gelato instead) I allowed my mind to wander back to it on the penultimate day. A couple of hours later, my plan for this week changed in a moment.

The result, it turned out, was progression.fyi, a collection of open source and public progression frameworks.

  • Built in a day (plus another couple of hours to add a mailing list)
  • Shared on my Twitter and Linkedin feeds only
  • Several thousand visitors, several dozen mailing list signups, a bunch of DMs/emails for follow-ups.
  • People posted it on Hacker News, Product Hunt etc. Others were tweeting/sharing it themselves (I only discovered all of this through GA)
  • A funny moment as someone shared it on a slack group I’m in, not realising I’d made it.

*Record scratch* *Freeze Frame*

You’re probably wondering how I ended up in this situation.

Back at Deliveroo, I was a design manager. A first time manager, who at one point had eight (amazing) designers reporting to me. Learning how to be a good manager took up all of my time, and I felt that I’d barely scratched the surface when I left.

One of the tools that us design and research managers started developing was ‘D3’ - a ‘Deliveroo Design Development’ document, to explain to all the designers, researchers and content writers (us included) what good looked like at each level and what was expected of them as members of the team. This ranged from soft attributes like intellectual humility, to hard skills like proficiency in our core tools.

We all needed to know how to grow at work. We needed clear, fair goals and a way to get there.

The process of creating this document was long and challenging for a number of reasons.

  • First: there was a moving target with aggressive team growth numbers to hit. With every stage of team size we’d need to rethink how many levels we might need.
  • Second: writing is really hard and there was a huge amount of content to write. With every new box filled, there had to be a discussion about the language and nuance.
  • Third: we were in many ways deciding our own fate as managers – something we frequently talked about openly. How could we make the best decisions for the team even if that meant changing our own career paths?

I would count that group among the very best people I’ve ever worked with, not only in terms of being ‘good at their jobs’ but also for being open and working together on a shared goal, in no small part because of Simon’s thoughtful leadership.

But it was still really really hard. I don’t think we ever cracked it while I was there, despite off-sites, endless feedback sessions with the team and hours of spreadsheet wrangling.

Back to the present. I’ve been looking at the broader themes of career progression for a few weeks, in areas from personal career development and coaching through improving those 1:1 manager employee relationships all the way to understanding how the big (mostly crappy) HR SaaS companies work.

But for months now, I’ve kept spotting other design managers and leaders sharing eerily similar documents to D3 themselves, or asking ‘are there any good examples’.

That’s why progression.fyi was born.

It’s very early days but if the reception to this simple site is anything to go by, then other people are feeling this pain too.

That’s good news for me.

My to-do list from last working week:

  • Speak to 10 more users (Done)
  • Build and share a landing page (Not the page I expected to ship, but done)
  • Get a v0.1 MVP up and running (Paused on this…)
  • Explain what I’m working on in a blog post/mailout (Done!)

The Good

  • Shipping something feels good, even if it’s simple. Getting a reasonable reception to it is also good. It’s all good data for my brain and confidence.
  • Holidays are very good. It’s SUCH A FALSE ECONOMY to not go on holiday. That week of work is 100% less important than your mental health. I suspect if I hadn’t gone to Italy, I would have been working on something different and may well not have shipped anything this week, or last… I need to write more about this sometime.

The Bad

  • This update has slipped, perhaps for good reason but still a frustration. I read somewhere that writing is a muscle you need to strengthen. I need to do some squats.
  • The flipside of shipping something is you do start to look at the numbers a lot. Definitely been distracted by GA, Twitter, Linkedin and Slack more than most weeks. Some of it is research/helpful but some of it really isn’t. 2 minutes of replying to a tweet too often leads to half an hour of reading depressing political commentary.
  • About once a day, I’m still getting the ‘what the hell are you doing, you’re not earning any money’ tap on my shoulder. Just enough to freak me out for a bit. Still learning how to not be a salaryman.


  • His Dark Materials is complete. (Thanks Graham for suggesting I power through and finish it). Such an immersive world, and some lovely narrative devices around the Daemons. Would definitely recommend to anyone as a break.
  • I took ‘Rework’ on holiday too - it looked like a good thick holiday read, but half of it is illustrations! Read it in about 2 hours. Still nice to be reminded of some of those common assumptions we don’t need to make when starting a business.
  • A bunch of stuff around maker/manager and progression obviously. This Farnam Street post was a good one.

Goals for next week

  • Follow up with fellow ‘FYI’ers to learn more about their problems.
  • Explore revenue ideas for FYI. I’m interested in any one of ‘productised service’, ‘digital download’ or an actual piece of software. The beauty of trying to bootstrap is I need to solve this early on.
  • Make a more robust content marketing plan. How do I help the people who need my service, find me, for free? By having opinions on the internet! Scary.

(Yep, no design or product goals in there. Welcome to being the whole business, jonny…)