I wrote this blog post early in 2017. Besides my day job leading the analysts at Wise (formerly TransferWise) I was also a part of the “planning guild”. There were four of us and our task was to coordinate the quarterly planning cycles for all 35+ internal teams.
There was just one problem: planning was broken.
-- START --
Every quarter — over the last 6 years of TransferWise’s existence — each product team has presented their plans to the rest of the company during a special day. That’s what “the planning day” is.
It’s the glue that keeps our autonomous teams together. Everyone knows how it works, what they need to do, and what they’ll get out of it.
There’s just one problem. It doesn’t work anymore. We now have more than 700 people, 35+ teams, and they’re spread across the globe.
There are bunch of traditional ways we could solve this planning conundrum, and obvious reasons why these wouldn’t work:
Give each team just a few minutes to present a super-concise message: but it’s so short, what’s the point?
Make planning just once-a-year: nope, the world changes way too fast.
Make it three days long: we ain’t got that kind of time.
Do it over hangouts: a 10-hour 9-office “can you hear me now?” marathon is insane. Just no.
Only invite “senior managers”: Really? You don’t know how we work at Wise, do you?
Etc, etc, etc. None of these would work for Wise.
You’d think this is a problem for our founders and senior leadership team. In a sense it is, but they won’t solve it. Instead it’s a problem for whoever thinks it’s a problem and takes the time to solve it. One of them is me. Over the last couple of quarters, with a few colleagues, I’ve helped to put together the plan for “the planning day.”
Like any of our product teams, we gathered feedback from our customers: the people of Wise.
Some of feedback we collected was radical, some modest, but in the end it was our decision. When I read through the feedback, I found a kernel of an idea on how we should do it. But it was such a different idea. We’d never tried anything like this. It’s our one and only chance this quarter to do planning. If it failed, we waste 600 people's time,. Or worse, we might derail some teams. The stakes were high.
Since two of my planning team members were on holidays and the other was unreachable, it was my decision. I pitched it to my colleagues (who in spite of being on vacation gave feedback) and a few others who I thought could help me evaluate whether we should take the risk.
I decided we’d do it the radical way. Completely differently than we ever had. And see what happens.
I winced when I sent off the email describing the new plan. I emailed everyone. All 600 of them. I wondered if I could get fired for stepping so far out from what was expected.
The first reply I got back was a simple “Love it!”. The second response was this though:
I hated receiving this feedback because she was absolutely right! It was in the front of my mind. I wrote an extensive pro-and-con list and got feedback from a dozen people on it. I very nearly did not do it for the exact reasons my colleague pointed out.
But then I did. For a few minutes, I wondered whether I’d made a huge mistake.
A few minutes after that I got this message from my colleague Wander (who was the main inspiration for the idea) in slack:
I got a bunch more messages that afternoon. The vast majority echoed what my colleague Wander wrote. At that point I felt good, but surprisingly, still not great. I still had doubters, but I guess you can’t make everyone happy, right? I knew going into this that not everyone would like this plan. I knew there were potential downsides, but I hoped that the net benefit was positive.
But then… a bit later, after the buzz of making the decision had worn off, I felt different. I was ecstatic and knew the risk was worth taking. What changed?
I realized that if I’m not getting messages like the first — concern that we’re changing too much too fast and that we don’t know what will happen in the future — I haven’t pushed the limits. If that happens, I’ve already, consciously or not, stopped myself far short of what I might just barely pull off. And I’d have resigned the whole team to doing the familiar, even though it’s not working.
I don’t know if this idea will pan out — we’ll see in a month — but I’m confident now it was worth trying.
-- END --
I’m incredibly proud I took this chance. This was the very first “Mission Days” for Wise. It’s evolved and is still going strong years after I left Wise.
I wrote this blog post early in 2017. Besides my day job leading the analysts at Wise (formerly TransferWise) I was also a part of the “planning guild”. There were four of us and our task was to coordinate the quarterly planning cycles for all 35+ internal teams.
There was just one problem: planning was broken.
-- START --
Every quarter — over the last 6 years of TransferWise’s existence — each product team has presented their plans to the rest of the company during a special day. That’s what “the planning day” is.
It’s the glue that keeps our autonomous teams together. Everyone knows how it works, what they need to do, and what they’ll get out of it.
There’s just one problem. It doesn’t work anymore. We now have more than 700 people, 35+ teams, and they’re spread across the globe.
There are bunch of traditional ways we could solve this planning conundrum, and obvious reasons why these wouldn’t work:
Give each team just a few minutes to present a super-concise message: but it’s so short, what’s the point?
Make planning just once-a-year: nope, the world changes way too fast.
Make it three days long: we ain’t got that kind of time.
Do it over hangouts: a 10-hour 9-office “can you hear me now?” marathon is insane. Just no.
Only invite “senior managers”: Really? You don’t know how we work at Wise, do you?
Etc, etc, etc. None of these would work for Wise.
You’d think this is a problem for our founders and senior leadership team. In a sense it is, but they won’t solve it. Instead it’s a problem for whoever thinks it’s a problem and takes the time to solve it. One of them is me. Over the last couple of quarters, with a few colleagues, I’ve helped to put together the plan for “the planning day.”
Like any of our product teams, we gathered feedback from our customers: the people of Wise.
Some of feedback we collected was radical, some modest, but in the end it was our decision. When I read through the feedback, I found a kernel of an idea on how we should do it. But it was such a different idea. We’d never tried anything like this. It’s our one and only chance this quarter to do planning. If it failed, we waste 600 people's time,. Or worse, we might derail some teams. The stakes were high.
Since two of my planning team members were on holidays and the other was unreachable, it was my decision. I pitched it to my colleagues (who in spite of being on vacation gave feedback) and a few others who I thought could help me evaluate whether we should take the risk.
I decided we’d do it the radical way. Completely differently than we ever had. And see what happens.
I winced when I sent off the email describing the new plan. I emailed everyone. All 600 of them. I wondered if I could get fired for stepping so far out from what was expected.
The first reply I got back was a simple “Love it!”. The second response was this though:
I hated receiving this feedback because she was absolutely right! It was in the front of my mind. I wrote an extensive pro-and-con list and got feedback from a dozen people on it. I very nearly did not do it for the exact reasons my colleague pointed out.
But then I did. For a few minutes, I wondered whether I’d made a huge mistake.
A few minutes after that I got this message from my colleague Wander (who was the main inspiration for the idea) in slack:
I got a bunch more messages that afternoon. The vast majority echoed what my colleague Wander wrote. At that point I felt good, but surprisingly, still not great. I still had doubters, but I guess you can’t make everyone happy, right? I knew going into this that not everyone would like this plan. I knew there were potential downsides, but I hoped that the net benefit was positive.
But then… a bit later, after the buzz of making the decision had worn off, I felt different. I was ecstatic and knew the risk was worth taking. What changed?
I realized that if I’m not getting messages like the first — concern that we’re changing too much too fast and that we don’t know what will happen in the future — I haven’t pushed the limits. If that happens, I’ve already, consciously or not, stopped myself far short of what I might just barely pull off. And I’d have resigned the whole team to doing the familiar, even though it’s not working.
I don’t know if this idea will pan out — we’ll see in a month — but I’m confident now it was worth trying.
-- END --
I’m incredibly proud I took this chance. This was the very first “Mission Days” for Wise. It’s evolved and is still going strong years after I left Wise.
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Mr JeffProphets and Professionals
I wrote most of this with my colleague, Mallory in late 2018, when we were both at Wise (formerly TransferWise). That’s why it’s a bit more readable. -- How to think about the tensions scaling up a startup This is too simple, but hear me out. You can split start-up people into two camps. Some we’ll call Prophets. The others are Professionals. Organizations like Wise have both. Every company has both.Why do we care? Three reasons.The first is that when startups are fortunate enough to grow up ...
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I wrote this in November 2015 while I was at Wise (formerly TransferWise). I wrote it after being completely captured by a book I read called ‘Reinventing Organisations.’ It was such a good book, and it applied so closely to Wise that I couldn’t not write it. I was so inspired by the book an Wise that I wrote this long essay (6000+ words), hosted a long lunch interview on the topic with Wise co-founder Kristo, and got probably 100 Wisers (of 500 at the time) to read the book. Looking back, my...
Mr JeffSelf-leadership part 1: organisations throughout history
This is part 1 of a 3 part series on self-leadership, based on my reading of Frederic Laloux’s excellent book Reinventing Organisations. All quotes, unless otherwise mentioend are from this excellent book. This post in particular summarises this book’s research into how humans have gone from tiny bands of cave dwellers to enormous organisations.Organisations throughout human historyIn order to understand organisations in the modern day, some context of the different ways people have organized...
Co-founder @ salv.com, formerly at Wise & Skype.
Co-founder @ salv.com, formerly at Wise & Skype.
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