Prioritizing Roadmap

"Prioritization and road mapping. So you have to be able to sequence the work much like in building a product, right? Building your growth strategy, you have to sequence it. That sequence has to make sense based on your growth models."

"The idea of being able to take all of these crazy inputs, trying to create a very structured model to figure out, 'Okay, what is true? Where do we have conviction? Where do we have questions? What are the most important problems to solve? How do you prioritize? How do you get a team rallied around a shared context in one single goal?'"

"It is a real wartime moment where you just need to blow up roadmaps, share context with everyone and say, 'Okay, everyone, we have a totally different mandate than what we did a couple weeks ago.'"

"I'm going to have some cannonballs. I'm going to work on a couple cannonballs and I'm going to have a bunch of lead bullets. And maybe it's 80% of your energies on those big cannonballs, 20% on the lead bullets, and having a constraint like that forces you to choose the fewer experiments that are actually probably the really good ones."

"My approach at Google was 70% of my effort and my team's effort should go on things that everybody acknowledges are important and useful and create value. Maybe it's boring, linear value, but some kind of value... once you do this, you have 30% of your extra time that you can plant all these seeds."

"We are constantly getting feature requests through sales, through customer success. And we had sort of no way, bar to decide well what do we take on, what don't we take on? And this clearly has become our bar."

"Being agile, not being stuck with roadmaps, being able to just say, oh, we're just going to switch priorities right away, is going to be super important... there's going to be capabilities that are going to drop. And you want to really, in some cases, if it really affects your business, you want to be able to jump on it really, really quickly."

"We call them... First BB is Brilliant Basics... The second one is Bread and Butter... Then, there are Big Bets... Breaking Bad essentially is a different world altogether. That's where you want to redefine your company... it gets down to product managers eventually prioritizing between these four. So I don't think it's a tactical prioritization product manager call. It really is a product strategy call."

"I like this framework that's taken from a book called Playing to Win and it talks about how strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose... it forces you to create clarity around where you're going to play and where you're not going to play. And so, this really helps the product team hone in on delivering value for a very clear set of people versus trying to build something for everyone."

"Just top line? I think identifying what is the biggest bottleneck, what's the biggest problem and iterating fast on saying, 'Okay, this is the biggest problem, let's really, really solve that problem.' And then picking in the next one and not overthinking, not dreaming out the long roadmap."

"We think about it as what season are we in? Season one might've been prototyping of AI and then it was all around models and reasoning models, and now it's the advent of agents... grounding everybody on the ethos of what are the secular changes? What are the customer problems we need to solve? What does winning look like?"

"I think the other thing is just we try to leave Slack in the system, not just for the unplanned, but for the slope. I think that we have to continuously be thinking about how we're going to disrupt the platform in our thinking and what we need to be investing in to make that possible."

"So instead of just talking about features, it's typically talking about features for the first 90 to 120 days, but after that we just talk about struggling moments because that's the seed for real innovation and basically where new products come from."

"They then are running their own roadmap. They're deciding what are the most important things for us to go work on, and having a prioritized list of those things and be able to start at the top of the list and work their way down with the pool of resources that they have."

"We went down from trying to ship maybe the 40 things that quarter to three and nothing else mattered. And that became the rhythm of the company for almost that entire year."

"How do you be really focused on where to invest your time, effort, and energy technically, which is why most of the engineering effort for Uber was on the dispatching system and the pricing system. That's just where the leverage was at the time, given the scarcity of resources."

"We have a rolling two year product plan. Strategy. Product strategy roadmap that gets updated every six months with releases. We release products every May and every November or October."

"I now try to say no to what I call fake work, which is things that feel like work, but they don't actually move the ball down the field. And I really try to say yes to the work that's very meaningful."

"What you then do is you... down select from those 10 to 15 opportunity areas into ideally three... ranking them on, I would say four or five key dimensions or criteria."

"In less mature product orgs who first bring in product ops, the first thing they ask them to do is streamline the planning process... How do I actually just get the people to plan the same way and give me the thing that they're planning and doing?"

"The most difficult thing about making that kind of effort is developing a common currency by which you can trade off their efforts. So this team is saying they can move this metric by X and this team is moving this metric by Y. I have no way to make those two things comparable. The growth model is the function that lets you do that."

"TAM or the size of the market actually matters very little because these are all big enough that they would dramatically inflect the curve of the business if you make them work. It's much more relevant to focus on a couple things. One is how adjacent is that to the business as a proxy for can we actually go get it?"

"Start with the potential outcome, then look at probability not the other way around because then you're going to apply that mental filter and throw out ideas that may not have been worth throwing out."

"At the bottom of every team charter we have a section called, Think Bigger. 'With 20% more time, what would you do that isn't on this list already?'"

"70/20/10 investments model... 70% of your building time should really be going to your core product, that has product market fit. 20% of your time should be going to strategic initiatives that aren't core... And then, 10% of your time should be going towards bets."

"We have what we think of as the public roadmap. This is basically what people have asked us for... So we have a second roadmap which we think of as a secret roadmap."

"The way that you make a decision on which one you focus on is similar to best customers. So high willingness to pay... urgent problem... high retention or even expansion potential... customers congregate in a way that make them really easy to market to... or you have an unfair advantage with this market."

"As a rule, I never used rules as thumbs, but these two percenters, I would kill them. If I launched something and it was only 2% we'd, we called it scraping the barnacles, just get rid of it."

"The idea is that, roughly, you shouldn't be spending more than 10% of your time planning versus executing or building. Which means that if you're working quarterly 10 weeks, you should spend one week planning."

"Whenever someone wants to have a strategy conversation, it assumes that they don't understand their priorities. The priorities is always a list from top to bottom where there's one thing that's more important than the others. You can't really have a strategy session about the other things because there's only one thing to work on."

"We started this thing where just basically we call it orange and red priorities... We said, these are the big rocks we got to get done. We're going to get those things done first. We're going to be upfront and honest with you, and these are the things and these are price. And then you can plan from there."

"Given the same amount of skill intelligence and resources, a product manager with a great innate ability to prioritize is going to generate 5X the impact of someone without that skill."

"I suggest using ICE, impact, confidence and ease. I think I have a slide coming on this. So impact, confidence and ease which is basically a way to assign three values to each idea."

"I recommend using outcome roadmaps saying by October we want to achieve this outcome. By Q4 we want to launch in another three countries, or we want to grow our usage in India by that much... Otherwise you want to keep it open and the roadmaps can kind of suffocate this process if you decide upfront with low confidence that this particular idea must be launched."

"When you can be really laser focused on, my goal each quarter is to make this metric go up, I think it's much easier to make sure that you're working on the highest ROI thing. I think when you think more about like, oh, I want to make this feature better, I think it's easier to get lost in what better means."

"A roadmap in strategy is not a commitment. Instead, it's a way to double check if your plan makes any sense at all and is even anywhere near feasible. Because what happens to every team I see do these roadmaps, you put it together and you realize 'We're not going to hit our vision in five years or 10. This is like a 30 year vision, if we keep going at the pace we're going.'"

"It's not about how do I go faster? How do I get more efficient? It's about how do I put the thing that is the most important first in my day or in my life, and then build everything else around that and accept that you're going to need to do a bunch of those little things."

"The whole point about a roadmap is that it's not designed to be your plan. I think about it as being a prototype for your strategy. What I mean by that is we talk about prototyping all the time in the lean world and a prototype is essentially a way of checking your assumptions."

"So we sat down and we came up with a three column roadmap, current, near term, future, which became now, next, later. And it took away the simple concept of a timeline at the top."

"I don't plan long-term because I want to do what I think, not what I thought... Every six weeks, we rethink what we're going to do next. We're very much an in-the-now company, making it up as we go."

"You are one of the best people I've ever worked with at solving problems three through 100, but I need you stuck on problems one and two."

"You have to be very intentional to carve out time for exploratory work for deep dives because as you mentioned, there are always more questions and more work to be done than hours in the day."

"When something comes up to be able to say, 'Hey, this data poll that you want me to do, is this more important than these other three things that I was going to be working on? Yes or no?'"

"You're telling a story. So what I want from you is I want themes, I want a story. Why are these things the biggest things to invest in these levers, the biggest ones to pull? And what I really don't want, what I think is a very common mistake from road mapping is people thinking a spreadsheet with a bunch of projects, the RICE framework, everything has an impact, a cost and an effort column filled out. They think that is prioritization and that is a roadmap."

"I think you can go too far either direction, right? It's like everything in life is about balancing the polarity between two opposing forces. And so in this one it's like, yeah, you go too hard in division and theory land... And you just get wrapped around the axle of like, well, that sounds really good in theory, but I have no idea how to even start executing on this... But you could probably go too far into execution land too... It was like, people would be like, 'I'm just going to run through a wall. I have no idea if that's the right wall to run through.'"

"AI research progress is bottlenecked by management, research management. It's because you have constrained set of compute and you need to allocate the compute to the research paths that you feel the most convinced about. It was like you need to have a really high conviction in the research paths to put the compute, and it's more return on investment kind of situation."

"The cycles is just a way to say that for the next week or the next two weeks or whatever timeframe, we are going to work on these things and these other things we think are the priority or the focus for this timeframe."

"Internally, we also talk about this, you knowing RPG games, you have the main quest lines and then you have the side quest lines. And we often talk about the companies avoid the side quests. There's always ideas people have... This doesn't progress the main quest line, which is building this product and making it awesome for these customers."

"The ritual is essentially you can take any set of problems or solutions or themes or whatever you want to get people's input on, and you put those into a table and then people can basically vote with their dollars and usually you allocate $100. And so people will go through and say, "Oh, I want to allocate $10 to this and $20 to this and $50 to this because I think it's really important.""

"One, going back to the mission, is this actually going to help us get to AGI? So there's a huge focus on there's this potential shiny reward right in front of us, which is optimize user engagement... And is that really the thing?"

"Literally, for your product folks, the number one lesson... you cannot prioritize a product roadmap without having a willingness to pay conversation. If you're just prioritizing based on what you think or what you feel or technical resources, you're getting it wrong."

"You don't need 20 features to solve a problem. You just need one or two features which work really well. This whole concept of critical user journeys. How do you make sure that, if you're solving problem X, any feature that you build in the product... should be well designed and it should have the focus and prioritization so that you're only getting things for the critical journey so that the user can use it and not get confused."

"The best PMs not only can find the one thing to work on, but they can stay with that one thing long enough to actually finish it."

"Getting to the one thing you should do is extremely difficult and being able and having the gumption to say no to all those other things is really hard, because there's probably at any given time, 10 things you should do, but you can't do 10 things."

"The Low Impact Death Spiral is the dynamic in which every medium to large company I've ever worked with finds itself in one way or another... It starts with adding little features here and there, making little cosmetic improvements because it's easier, it invites less scrutiny and you're less likely to mess up something important"

"Are we estimating and measuring impact in the same unit of measure as our goals? Because if we're doing that, then we're keeping ourselves honest and we're saying, 'Does this actually have a chance of contributing?' Whereas again, if we get really clever and we come up with a proprietary scoring system and all these little intermediate steps, we can feel like we're doing really awesome work and being very, very terribly smart. But we again, run the risk that we are going to lose our connection with why we're setting about to do this work in the first place."

"In a feature team, basically you are handed a typical roadmap. Almost everybody, even though I wish this wasn't the case, almost everybody to have the same thing, that it's a prioritized list of features and projects. So some stakeholders got together, usually quarterly, and they say, "Look, to run our part of the business, we need these features. It's not really complicated. We need these features.""

"He was looking for a portfolio roadmap of what everybody's doing and he wanted to see what are the big pushes we're making from a feature perspective and how do they tie back to our overall strategy and our goals."

"You work on problems that have a 10X positive or a negative impact... That's what you focus on. That's what you spend bulk of your time."

"It just always comes back to how do I set strategy, how do I deploy strategy, and how do I make sure it's well communicated and that everything that we're doing on the tech teams, on the product teams, is laddered up into a company strategy that's well prioritized."

"A good test is you go to all of your teams, and you ask them what they're doing and why... They can connect everything they're doing, from the tactical stuff on the team, all the way back up to the business metrics."

"Some of the normal things that people would maybe reach for in building the company early on, we really let those fires burn for a long time, especially when it came to things like sales and marketing. And so just working on the product, and building a product that you like first, your team likes, and then also then adjusting it for some set of users, that can kind of sound simple, but then, as you know, it's hard to do that well."

"The stuff that we absolutely have to say no to is the exact kind of thing that leads to this bloatedness that makes ICs hate their lives. It's customization features requested by middle managers in order to make reporting a little bit easier at the cost of making IC workflows worse."

"At any given moment, we have probably 20 or 30 opportunities that we could possibly explore, just product opportunities, like problems to solve, areas to improve for our users, but they're not ready yet. We don't have enough conviction around how we might approach it. So, we just accumulate understanding of this stuff and periodically, we accumulate some more stuff, and then we reevaluate."

"You have to be ruthless with prioritization as something scales up and put out the largest fires first, because that was something that I didn't really fully understand, is how many things go wrong."

"I think the way that we think about, or us to think about our roadmap for any feature team at Slack is that it's a portfolio and it's meant to be a portfolio that's diversified a couple different ways. I think one is you want to diversify things that are meant to be new capabilities versus making the thing you've already built a little bit better every day... Are there things that are meant to be risky that you aren't sure are going to work but might have a lot of upside versus things that are known bets."

"I remember doing really on is actually talking to the leadership team and being like, 'I don't think we should be putting 50 engineers on this project. Looking at the rest of the roadmap and the rest of the priorities, excuse me, I think this team would likely be better served elsewhere.'"

"Difference versus table stakes, very simple... differentiation. So what's different and better? But critically, what's different and better in ways that customers care about?... on the other side, there's a entry requirement or table stakes... They're real basic stuff, boring stuff, and easy to ignore."

"Focus, it's the fundamental source of power and strategy. Trying to do too many different things is defocusing."

"Which of your ambitions can you begin to make progress towards reaching, and what's holding you back? What are the barriers? What are the problems? So I approach the question of the problem now through the filter of the ambition."

"You can classify anything that you build in a company into one of two categories, solution deepening and market widening. Now, solution deepening means making your product better for its existing users, but not making it available to more users. Whereas market widening means making your product available to more users, but not making the product itself any better."

"You get to these points of just diminishing marginal return in every system where it feels like you could put 50 people on this project, it's just not going to dramatically move the needle... You then find your next growth driver or set of drivers."

"As a general rule, as a general principle, I certainly try to make sure that we're always reserving some capacity for bold, audacious experimental research projects. You can think of those really uncertain bets as being five to 10% of the team's capacity. About 25, maybe 30% of the team's capacity should generally be on just operations. How do we keep our in-market products meeting customer expectations? And then the remainder of it, what is that, about 60% or so, is really on incremental progress for our end market products."

"Substack is a pretty principled company... prioritization standpoint and from a strategic standpoint... all things equal, do the one that holds constant this principle of control."

"What is our appetite for this? What is the maximum amount of time we’re willing to go before we actually finish something? And we have that startup moment... at least this, if not the whole project, this meaningful piece, we can literally walk away from."

"What that ends up meaning when the when a new user signs up is that there's too much in the beginning to to take in and understand, and you don't then have a very focused product that gets the user to the thing that you most want them to do. And that's actually part of the importance of understanding level one, what your core action is."

"In order to be able to effectively run a high velocity testing program, you need to be able to source ideas from across the company. And that's why I came up with ICE, that if you're having people submit ideas and you can't tell them why their idea was not chosen, they're just going to get upset... But if you have a systematic way of being able to compare ideas, it's more likely that people will be able to get it"

"Brian also has another one... about how to rank your to-do list by finding leverage... he sorts his by which of these is most likely to create leverage of getting rid of the rest of my lists"

"L tasks which are leverage tasks... when you put in a certain amount of effort, you get 10X or 100X in return... neutral tasks (N)... overhead tasks (O)... as a product manager... all your tasks are not created equal, there are actually three type of tasks that you end up doing in such a role."

"You should stop doing work that simply provides a positive return on investment, ROI. And you should start focusing on work that minimizes opportunity cost... ROI mindset... end up trying to decrease the denominator... start working on the low hanging fruit. You start prioritizing the quick wins."

"The idea is the first bit of effort you put into something doesn't result in a huge amount of value. And then there's some magic threshold where it produces an enormous amount of value and then continued investment doesn't really pay off."

"Don't fall for fads. It's do the thing that your customers are asking for and are willing to pay for... if you have something that is working, don't get distracted."

"The other big lesson... it's also very important to know what you're not building. And this one is not only in big companies, I would say even in startups, it's extremely important to know what you're not building because you could very easily get swayed by customer X telling you to do this, customer y telling you to do that. And a product that tries to be all things to all people usually doesn't end up going anywhere."

"You don't win by doing 10 things well. You win by doing one thing really well and maybe you fail nine things. This is the thing that I've told the company, 'This is very different than school,' right? In school you optimize for your total GPA. But for companies, I just need to get an A+ on the one class that matters."

"We took all the churn reasons that our customer success and sales teams had been painstakingly collecting for years, grouped them by category, which was roughly product features we needed to build, sorted descending by ARR, took the top 10 things and made that our roadmap"

"One of the traps with RICE that we observed is that the C and E, the confidence and effort tends to cause you to prematurely deprioritize potentially high reach, high impact bets... ignore the C and E for a little longer than it's comfortable, and just sit with those high reach, high impact ideas with engineers and designers in the room committed to actually trying to solve them."

"the big rocks are not a laundry list of 20 things because if I asked you to make me a cocktail, you would put ice in first. Then you would pour the drink. You would not put the drink and then put the ice... So it's like 3, 4, 5 things that anyone can remember that are the biggest things that if we land, this gets us closer to solving the problems."

"We've just started trying something new called the $10 game for priorities... you and your manager might come in and you can list out all of your priorities and then show you through just dividing up $10 where you're spending all of your time. And I've done this with people and we've sort of gotten down to like, 'I'm putting 10 cents here this week.'"

"Before, we planned annually primarily. Now, we plan every six months, but for a rolling 12 months. So we have higher confidence in the immediate half, lower confidence in the following half, but we just plan every 12 months, every six months because it gives our business more confidence in what's coming and a better opportunity to align our go-to-market and product planning."

"What we realized is that some things were taking off, and some things weren't... we decided to kill the Tip Exchange. And suddenly, the publishing of projects in the portfolio went up... we killed groups. And lo and behold, more people published more projects... if you make the whole product about one thing, everyone does that. That core crank operates at 10X the velocity."

"We have a rolling six month roadmap that gets updated every three months and the first three months of that roadmap, we have a 80% position level... For the next three months... we have a 50% [level]."