# Pushing yourself to take big risks By [Mr Jeff](https://paragraph.com/@mrjeff) · 2021-12-19 --- _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 -- Outgrowing “the way we’ve always done things” --------------------------------------------- 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. How we decide important things at 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. Decision time ------------- 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. So what happened after I made the decision? ------------------------------------------- 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: ![ First feedback :-(](https://storage.googleapis.com/papyrus_images/1d5aff0b649f5cde3a32577bc577370e6ff17896469e9c0b19ac0253b5121b13.png) First feedback :-( 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: ![Second feedback :-D](https://storage.googleapis.com/papyrus_images/b552be0f4aee7da3a34edc572969f40df1f862bc55f385e21d02d1f1d7e0f286.png) Second feedback :-D 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. Reflecting on the decision -------------------------- 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](https://www.youtube.com/watch?v=pqKq4vUXEH4). [Go back to the main page](https://mirror.xyz/mrjeff.eth/s4lo91PGvKbaqy_jd505XcYdVzX81ElPFu3fnXzTotQ). --- *Originally published on [Mr Jeff](https://paragraph.com/@mrjeff/pushing-yourself-to-take-big-risks)*