Shreyas Doshi: evaluation

Transcript context

…Yeah, so you're basically saying there's all these productivity tricks, ways to do more faster. And no matter how many of these tools you've got, you are just going to take on more and more work, and they'll peter out? I'll say many of my most popular newsletters posts are, "Here's productivity tricks and tips." And so people are always looking for these. And I'm curious to hear where you go with this, of just like that is not the answer long term, there's a different approach? Yes, and so the challenge is the following. How many of you are going through some kind of annual planning right now or you're planning on going through annual planning? Please. Everybody loves annual planning, great. So let's take annual planning. If you are a high-level manager, leader within a company, what does your month look like? Or in some cases, unfortunately, what do your two or three months look like when you are going through annual planning? It's all these kind of spreadsheets to fill out, and meetings to have, and dependencies, and priorities, and stakeholders to meet, and so on. And so I noticed, for instance, that at some point, that was making me really busy, and then that was making me feel guilty now, because I had my team to look after and to support, and then I had product decisions to make and various other things, and I've gone on some planning retreat or whatever. And there you go, you last four, five, six, weeks, does that sound familiar to folks? Yeah? Okay, so I noticed that I needed to change that at some point, and actually found a solution, again, late in my career, but I found a solution, because I asked myself this question, which is, "Why am I so busy? I'm doing all the efficiency things, I'm managing my to-do list like a champ. I have my calendar set up just right. I have my routine set up just right. I'm working out so that I'm engaged at work, I'm productive, I'm doing all of that. Why am I so busy? Oh, it's planning season, and that is supposed to take up four to six weeks." And this was at Stripe when I encountered this. So that is supposed to take up four to six weeks. Well, I realized that you don't have to do that. And so at some point in my time at Stripe, what I realized is the following, we go through a whole all sorts of just rituals around planning for four to six weeks. Then, we emerge and we share our plan with our executives. You know the questions they're going to ask, like, "If money were no concern, what would you do? What is your ambitious plan? So if we gave you five more engineers, what would you do? What other things would you include in the roadmap?" Right? The standard stuff. And so you emerge, you do your presentation, and then you publish the plan, and then you start the new year with a lot of enthusiasm and a lot of excitement. And January goes fine, until you get three customer escalations for features that were not in your plan. And so now, you try to figure out how you're going to revise resources. You go talk to some dependency team that's going to sort of support these new features from these customer escalations. And you go through that process, and you revise your plan again. And then, usually by the time it's last week of February, everybody's forgotten the actual plan. And now, we are executing off of some other list somewhere. at process, and you revise your plan again. And then, usually by the time it's last week of February, everybody's forgotten the actual plan. And now, we are executing off of some other list somewhere. And by the way, when you mention this at times, politely of course, you might mention like, "You know, I'm noticing we are not actually really using the plan that we spent four to six weeks minimum doing." And then, some smart person in the room chimes in with, "Plans are useless, but planning is everything." I don't know, Eisenhower, somebody else, I don't know who said this, "Plans are useless, but planning is everything." Nobody knows what it means. Nobody knows what that means, but everybody appreciates, "Ah, plans are useless, but planning is everything." Right? So I went through a few years of this. And then I go, "You know what? I'm going to bend some rules here." And so what I realized, Lenny, is you don't have to go through these four to six weeks, and it was an accident. Basically, what happened is around that time, the product I was working on, Stripe Connect, it's like a major product for Stripe, major, major business for Stripe. And I had put together a product strategy, like a real product strategy for this product. And so this must have been earlier in the year. And so now, planning season came along. And the interesting I found is that because I had a real product strategy, not one of those fake ones, a real product strategy that I had gotten alignment on with everybody, my planning for this major product for Stripe took me like three days. Right, so while a lot of my peers, unfortunately, for their own products, were in this four-to-six week cycle of planning, and meeting, and blah, blah, blah, I just put it all together in three days, and whatever artifacts were needed, I put them together. I did not fill out some templates. That's where it's about bending the rules, because if a template doesn't make sense, why should I fill it out? There's no need to fill it out. And so that's when I realized that actually, if you have a real product strategy, a real one that everybody is aligned with, that you have got pre-alignment on, then a lot of this nonsense we tend to do with annual planning actually goes away. Now, you still have to do some resource allocation and all of that, but even there, you don't need that false precision. How many of you have gotten into arguments about, "So should it be eight engineers for this team in 2025, or nine engineers for this team in 2025?" Like, who cares? We all know that even those numbers that we set up, we don't actually follow through on them, as 2025 happens. So that's just an example of where we spend a lot of time on things that we think are strategic, that we think are important, but actually, we ought to spend that time on other much higher leverage things. Right, now it does require some upfront work, in this case upfront work on a clear product strategy that everybody understands, that everybody's aligned on. But frankly, if you have that, planning should be a breeze.…

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