In the file: Using design sprints to drive annual planning at Stripe

My Dear Friends of Figma in All right so our main people who will be leading the live stream today are michi and talia they’re both product designers from stripe and they will be the ones talking about how they have um approached annual planning with their teams so i will kick it off to them wait one moment.

Okay all right so thanks sigma team we’re really excited to be here today and as anna mentioned we’re going to be talking about how design sprints are used for annual planning but first an intro about myself i’m michi.

And i’m talia and we’re product designers at stripe now michi we can probably guess what they’re thinking right designers leading planning come on no way that always ends up in product slap and we’re pleased to share actually no not anymore.

As we all know we’re professionals at making really good looking rectangles and moving them around but today we’re here to let you in on a little secret there’s life outside the rectangle today we’re going to share how designers can play as much if not more of a role in the strategy and planning for your.

Team pixel pushers not us but before we share our secrets we’ll tell you a little bit about stripe and what we work on there for those who don’t know stripe is a financial services and payments company online payments processing for internet.

Businesses is our jam we’re available all over the world and companies of all sizes use our products to accept payments send payouts and manage their businesses online as product designers we help shape how the end users will interact with the various products that stripe puts out so we work specifically on a product.

Called stripe express which is built to address the financial needs of solo professionals or people who work for themselves and earn money from multiple places online an example of a solo pro could be a journalist who hosts a podcast for spotify while also writing a newsletter on substack and maybe teaches an online.

Course unteachable but let’s get back to the initial secret we said we’d let you in on planning we get that a lot of what we’re going to talk about today will look like a design sprint and it is design sprints are super valuable on the outside it looks like your standard design sprint but in reality it’s kind of the perfect tool.

For team wide planning so okay okay we know what you’re thinking designers leaving a design sprint groundbreaking right but what got us there wasn’t actually a desire to make these sweeping design changes instead we saw that a design sprint.

Could be the path to get people planning in an inclusive and collaborative way so what were we going through before the design sprint we were in the midst of 2022 planning but we didn’t seem to have a clear vision on what we were working towards for the upcoming year some of the product ideas mentioned.

Weren’t directly tied to user needs and we were struggling to properly explain what express was we felt like decisions were more reactive than proactive and on top of all of that we ran into the thing that so many people fear a reorg now again you may be wondering why on.

Earth would we want to be involved in planning there are so many more interesting things to do as product designers like maybe talking to users or building prototypes or going deep on interaction and motion details but it’s important that design not only have a seat at the table but that they.

Actually sit at that seat at the table when they have it and in that case it means being deeply involved with planning where important long-term decisions are made planning is not just for pms it’s for everyone no one wants to spend a quarter working on things that they’re not excited about or that isn’t impactful.

For the user we felt that design was uniquely positioned to help facilitate these important conversations in a user-centric way so we ran into that fire and with the help of a design sprint the team got back on track and aligned now how did we do this you may ask.

Here are some things we learned from our sprint that we think could apply to you and your teams the first insight despite the name design sprints aren’t actually about design the purpose of a design sprint is actually team alignment design acts as the guide through which.

You validate ideas and also brainstorm and question whether those are the right ideas to include in your roadmap let’s be real though validating ideas and getting people on board is hard and that’s why partnering cross-functionally is critical we were really lucky to have supportive partners product partners who eagerly.

Promoted and encouraged the sprint that we had in mind and wanted us to take the lead so forget about sprints only including designers everyone’s able to be creative and everyone’s able to be user focused and by including people in other disciplines everyone can be part of the fun.

Now we know that in this specific instance we were pretty lucky because our cross-functional partners were open to this idea but plenty of you out there don’t have that in fact we’re sure many of you even have partners that don’t think it’s needed so how do you handle it then first you do need to ask yourself the.

Difficult question do they have a point do they not want to sprint because it’s not necessary at the moment or because they need to prioritize other things as we know design is always eager to do northstar work so it’s important to know when it’s the right time to do it so when is the right time to get.

Involved in planning if your team is unable to explain how the projects on your roadmap fit together that could be one indicator confusion over long-term goals could be another and if you notice that user needs don’t come up during planning that’s a pretty good indicator too.

Another suggestion could be word choice yes it could be as simple as the framing of your suggestion for example rather than referring to our sprint as a 2022 north star we called it a 2022 design synthesis when we shared it more broadly sometimes word choice can surprisingly be key in making people more receptive to the idea.

Our next insight stop collaborate and listen and then plan and by this we mean before you schedule a sprint before you come up with all of the sprint activities before you send out invites collaborate with your colleagues over what you have in mind this can ensure that everyone has the.

Same expectations going in around sprint goals and deliverables but don’t get us wrong this certainly was not all rainbows and unicorns on our end we actually did stumble through this a bit personally at the start of planning michi and i dove right in and we got overly excited let’s do a four year vision sprint this.

Will be so cool we can think so far ahead but as soon as we shared out a dock with some of our partners they told us we were jumping way too far ahead we were a new team that had just had a reorg and we were working on a new product what we needed was an illustrated.

Direction for the upcoming year so we went back to square one and we updated the dates the goals the deliverables to only reflect a time frame for 2022 and because we shared this broadly with the attendees that we planned on inviting we got to hear their feedback and learn where there was confusion or.

Concern for instance many of the people we invited had different ideas of what the output of the sprint would look like some people were expecting pixel perfect final designs for all of 2022 others had no idea what to expect so this did lead us to hold more explicit conversations as a team about what the.

Expectations should be for the end of the sprint other feedback we got was that the time that was needed from the team would just be too much so we wound up reducing the entire sprint from two weeks down to one given that feedback because we collaborated on a.

Straightforward dock with our co-workers before any serious planning occurred we were able to create a successful sprint that really worked for a team specific challenges and goals and what our team needed was an opportunity to get to know each other and the work but alignment goes both ways and that.

Leads us to insight three if you want a design sprint to be a successful tool for planning you have to design it with your specific teammates in mind oftentimes the challenge can be time everyone’s got their own projects everyone’s got their own priorities and everyone’s got their own meetings to.

Attend the challenge of finding time in the calendar for everyone to come together has basically become a meme at this point and once you find that time then making sure everyone can focus entirely on the task at hand especially while remote that is nearly impossible.

So we knew this would be a challenge from the start and as a result we made it so that anyone could drop in on any workshop and meaningfully contribute even if they weren’t present for the other activities now the extra busy teammates could scan the agendas and decide which workshop was most relevant given their.

Availability and interest and we also kept each workshop to no more than an hour and a half because after a certain point as we’ve all experienced eyes tend to glaze over and people start multitasking especially when you’re on zoom of course an hour and a half is still a really long time.

But the truth is having less time can actually be an amazing constraint that allows people to be creative and focused a lot can come out of 30 minutes huddled with your team around a whiteboard virtual or otherwise so once we had determined the right timing for each workshop and all the prepping and the planning was checked.

Off we transitioned from being planners to facilitators our jobs were to tease out and reinforce the value and the merit of every person’s ideas regardless of that person’s role or seniority and once the team’s creative juices started flowing we asked each person to.

Describe what their long-term vision of what express could be in the future and we grouped people into teams and asked them to imagine what a successful launch article could look like for express one year from now this really got us as a team to zoom out and highlight the values that mattered most without getting too fixated on the.

Nitty gritty details or specific feature work and then once team themes emerged we allowed people to cast votes on the ones that resonated most we set up photos and designated voting dots for every participant and this reinforced that everyone had a say instead of favoring the loudest voices.

In the room we enabled everyone to contribute equally but we couldn’t only focus on high level directions we also needed to focus on user needs as we mentioned before we had just been through a reorg and so many folks were new to the team in the product areas they needed to be onboarded onto a.

Product and get acquainted with the problems that we were solving for we realized that this would actually be the perfect time for teammates to work together to learn the user needs and pain points of their new focus areas so we divided the attendees up by their new sub teams we had them map out the steps of their.

Users current journey and then we asked them to identify the spots that cause friction or frustration for the user from there we had them identify opportunities based on the pain points that they uncovered and to brainstorm ideas with no limitations on how to solve them.

So this exercise did two things for us for one it validated that the new teams formed from the reorg mapped pretty perfectly to the user needs which was really great but two the ideas that came out of this exercise ended up directly informing our team’s mission and roadmap.

Now we know what often happens is that a sprint can take place everyone has a good time and then it kind of slips through the cracks nowhere to be found not especially on the roadmap which leads me to the last and final insight the key to getting the word out and.

Making this entire effort worthwhile and turning the ideas into reality is socializing and celebrating the work your team has done unfortunately because we are now living in a largely remote first world you will need to create something that is easily shareable and that can live on its own without you being there to.

Explain so after the sprint michi and i created a visual deck that detailed why we did the sprint what the synthesized product vision looked like for express in 2022 and crucially how it tied back into stripes broader business goals we did make designs to illustrate the vision but we intentionally kept them.

Low fidelity so that the focus really remained on the strategic direction we announced this to our broader teams in the form of a shipped email and then before we knew it the team was buzzing about this new direction and how to build it and this also kick-started conversations with our partner teams and in general it.

Became an example of a more collaborative way to plan but sadly planning is never done you need to keep challenging and revisiting the work you’ve landed on as we know with design we should never treat any work too preciously as hard as it may be for us recovering.

Perfectionists out there so once we landed at our 2022 product vision we ran a workshop to identify assumptions unknowns and risks as we just mentioned the direction that we landed on was only that first pass we did not know everything and it was.

Critical to identify what needed more exploration and validation and what came out of that was that these open-ended questions became the priorities for our research roadmap so we know that was a lot and a lot of talking scheduling and planning and some of you might be saying to yourselves what if i don’t have the capacity to do.

This on my own so in that case enlist your non-designer teammates when i was in a startup i was the only designer but i convinced my pm to lead it with me remember a design sprint is not just about design and planning is for everyone so what happened at the end of our.

Sprint we came out with a better sense of how everyone’s work was connected we had real proof that design could drive strategy in a collaborative and user-focused way we were able to identify clear areas of focus for each of the sub-teams and we found new opportunities to.

Improve the product for our users but we know that throughout this presentation we’ve been talking a lot about designers so do not worry our cross-functional partners we see you too here are some ways you can help so for our product managers out there promote and encourage design-led sprints.

In the team non-designers will look to you to determine whether an activity like this is valuable for people in other verticals engineers definitely attend the sessions and participate bubble up any big engineering.

Initiatives that may impact the user experience and work in advance with design to incorporate it into these working sessions design managers encourage your reports to involve themselves in planning and provide air cover so that they’re able to step away from their tactical day-to-day tasks.

Now we know that stripe is a particular type of environment and it may not be the one that matches your company or your environment so designing a sprint for road map planning will differ a lot if you’re at a later stage company or a startup so at a startup gathering stakeholders may not be the problem since there.

Aren’t too many people you really can involve everyone so there’s no need to be so formal in your planning you can do a whiteboard session in a room with your team you can also do a sprint for just the upcoming month if six to 12 months feels too long and if you’re at a mature company you.

Really need to be ruthless about who to invite so that the sprint doesn’t become too crowded you’ll need to be sure to invite and win the proper stakeholders of course but whereas in a startup your only stakeholder could be the ceo in a big company you could have many stakeholders in a variety of areas.

So it’s really important that you’ll identify who is the most essential during planning and that’s it that is the secret sauce so to review design sprints aren’t just about design stop collaborate and listen and then plan the team informs the sprint and finally.

Socialize and celebrate the work that your team has done we hope that you can try out the tips that we’ve shared and that you can bask in this new life outside the rectangle so if what we shared today excites you you should come and join us at stripe and help improve what product planning looks like in teams around the world.

Thank you amazing thank you so much michi and talia um this was super insightful and it was really great to see how you guys approach your entire process and edited your strategy as you receive feedback from other people that you are getting involved.

Um so now we can move on to the q and a portion so if anyone has any questions that they would like answered please pop them into the q a we’ll be using this um to reference and ask questions for the next around 10 to 15 minutes so um.

First question either of you could answer this but someone was wondering how do you buy in stakeholders to use design sprints outside of design occasion yeah i can speak to this and so my understanding of the question is like how do we get stakeholders to invest in design sprints outside of just.

Using it for design um i think that the first thing you do is just like as talia mentioned you really just have to be really aligned with the people so before you do anything you gotta talk to your teammates and um like make sure that they’re on board and understand what a design sprint can give.

To them um if they they’re not really aware of what a design sprint is maybe like a week of a design sprint is too much of a commitment and so what you can do is like work up to that by maybe doing like a one hour sprint or a one day thing and then they can start to see the process.

And the creativity that comes out of it and then you kind of work them up to a longer one week thing but it’s not just like zero to one real quick you gotta really like build the trust with your xfn partners and then really start to like show them what a design sprint or these like design kind of frameworks can can do.

Awesome um and there’s a couple of questions i’m going to tie them together because they’re very similar but some people are wondering um how you would go about with this implementing this for agencies or people who are freelancing and working with clients yeah um in that instance the same rules.

Can apply with your clients um you can get together with your clients to ensure that you’re perfectly aligned on what their vision is what their goals are for the project that you’re working on for them you can set up time to map out what the journey is that they’re envisioning for the people using their product.

And really just remain aligned so that when the time comes that you are delivering some designs to them um there’s no you know fires that go off and and you can all be fairly aligned with what the expectations are great um all right yeah we have another really interesting question where someone asked.

Did you have any favorite exercises that produced a surprising outcome i will speak to my favor which was the llama times um and it was featured in the slide deck that we just went over but it was an exercise where we had people um mock up like a newspaper headline of what it would look like and we were.

Really surprised to just see how creative you know all of our teammates were and it was very well written and actually i think from that like it was we were able to find like some key moments of like what does this product actually do and then we use that into our product.

I think for me um my favorite was the jobs to be done and opportunities where we split everyone up and had them map out um what their users journey really was because it kind of forced you to to be confronted with the real pain points that a person is going through and what they actually want to be able to accomplish.

Um i do want to mention that every single one of these activities was made in figma because we are largely remote and so that’s this just made it super easy we could see what everyone was working on and it made it so simple to share out after the sprint as well awesome and then someone else asked do.

Your product teams work in sprints on an ongoing basis did you organize this in addition to regular working sprints so our team doesn’t or so the engineering team does do sprints actually on the design side and product i don’t think that we do that um we paired this actually with our.

Um annual planning for our team um and then the rest of the time what we usually do is just make sure that we’re aligned pretty closely with engineering so that by the time they get to their next brand it can be like coordinated with where we’re at and that’s how we work awesome.

Um and there’s also a couple questions where people wanted to know if you could dive into some of the finer details around approximately how many sessions did you guys have um and also how long were those sessions and were you focused on trying to time box the activities that you had planned as well yeah so um.

We were conducting this sprint in december 2021 um in order to start brainstorming for 2022 and we were beginning to do planning um and so we did not have all the time in the world ideally we would have loved for to be an even longer sprint but we really only had one calendar week in.

Mid-december before everyone went away for christmas and things like that um so we ended up dividing it up into four workshops within over the course of the week because everyone was really busy that week um and as as we said earlier you know each session was anywhere from an hour to an hour and a half but never longer than.

That um and we really organized it in a way that anyone could drop in on any session they could just go to two of the four sessions one of the four sessions and they would still be able to participate just as much as anyone as anyone who was there for all four sessions um so it made it really easy and.

Seamless and we were able to get so much participation because it wasn’t an all or nothing invite and we got so much out of it but in the future you know if we’re not in a time crunch it would be really great to have something even longer and more focused and hopefully maybe one day in person absolutely.

Um all right let’s just answer just a couple more questions i’m also lumping in a couple with similar themes but um some people were asking about what recommendations do you have when it comes to organizations that have low ux maturity um and also are there challenges um that you experience when it comes to.

Onboarding non-designers into figma because that was the primary tool it seems that you guys were using or if you use fig jam as well yeah i can speak to this um i also tried to throw in a design sprint when i was in a startup and so you could say that that’s like fairly um like not a lot of people.

Knew what design sprint was didn’t really even know what jobs to be done was so um before i ever kind of like nudged or kind of asked or offered the suggestion of a design sprint i started pretty early on from the very beginning when i went in which was like let’s talk about these things.

Like about how design thinks about the work um it’s not just about actually just implementing a design sprint it’s about like often showing people how design thinks and what the value could be and the truth is it’s not just design sprints that we can that’s not the only thing that we could do and so um.

You know i’ve i did sharing sessions from the very beginning about how to think about jobs to be done um how to give feedback how to run design crits and all of these things like are very traditionally designed stuff but you know when you’re in like a very low maturity work organization or just not a lot of designers you’re gonna have to.

Like lean on your other non-designer teammates to really like bring them in and make them almost like your design partners and so i did a lot of that kind of like foundation setting before design sprint ever came along and so by that time um there was like enough trust built and.

Once that kind of like topic was broached it was like a lot more receptive and then you just really have to dig into like what are the concerns that they have what are the questions that they have sometimes it’s like you know they don’t feel like it’s attached to a metric or it’s too much time or they just want to build things that are.

Right away and so you just have to like figure those things out and then like slowly chip away at those concerns um but trust is like the most important thing from the very beginning awesome all right uh let’s just ask two more questions um one there’s a couple where they’re.

Asking around you know how do you organize and coordinate these design sprints especially for people who are new to this concept do you have any kind of advice for that and so by that does it do do you mean scheduling do you mean i mean i’ll answer in terms of scheduling um.

What’s really critical is that in advance of even sending out the invites you are talking with the people you plan on inviting to the sprint um and so that that can go to as little of the details as when is everyone available so obviously it’s better to plan as far in advance as.

Is possible because then it’ll make it a little bit easier to schedule but for us we really were in constant communication with our product partners our engineers the product marketing partner operations anyone that we knew we were going to be including and we wanted to come to at least one session.

And after getting all of those responses we really were able to schedule the you know a week that worked for everyone and get a much higher rate of attendance because of that great all right uh one final question so people were also wondering um you know what comes next is this how.

Your team is going to approach road map planning in the future are you guys going to be doing this on like a quarterly and yearly basis and then also people are wondering um if you guys are going to make any adjustments or changes in the future to how you’re approaching using design sprints for road mapping.

So we’ve gotten this done and one of the things that we were really excited about is that our team’s like fairly familiar with design sprints now and one of the things that we’re setting this up for is like a broader just like design longer term vision that one of our.

Teammates is also running and so we are now at like a baseline of like here’s where our products at and here’s what we’re going to be doing for like the next year and now that we have that out of you know like aligned now we can start to like run a little bit more longer term picture like two years on.

And like think about what we actually really want this to be in a more opinionated and like compelling way and so this has set us up to do a bigger design vision program um and then in terms of day-to-day work i think we’re gonna definitely have to like keep doing our roadmap planning and then.

Take the new things that we’ve learned and then bring it back to this deck this vision deck that we created or the synthesis deck that we’ve created and start to just like change it up and iterate on it um to reflect where we’re at at any given point in time i think also because our design sprint.

Was such a success and that we were able to incorporate real conversations but also just have fun even remotely it did lay a really nice foundation for the rest of the team so that now if we bring up the topic of a design sprint again people are really open to it even more than they were before this one because they had such a good experience.

And because we you know left that sprint more aligned now we even hear our cross-functional partners say like oh when are we going to do the next design sprint um like should we do it quarterly should we do it annually um so that that will also um you know whatever changes we do make.

Whenever we host the next design sprint we will ask for feedback from our partners but it will make it also significantly easier to to schedule it and to to invite people and have people attend awesome well thank you guys so much for taking the time to go through the entire process and share some really great tips.

And learnings that you guys had in using design sprints as a format to drive planning um for context um we will be sharing out the recordings once it’s been posted on our youtube channel so be on the lookout for an email on that if you would like to revisit this talk later.

Also we have additional live streams just like this they’re called in the file so if you’re interested in any of them please take a look at our figma.com events for any future plans that we have we also regularly post on our social accounts as well announcing when we have any upcoming ones and if you guys have any suggestions or.

Ideas that you’d like to share with our team please reach out at community figma.com um one final thing that’s also not included in the slide but we do have our annual conference coming up called config and registration is opened so please please definitely register it’s.

Going to be for 24 hours so it’s accessible to people all around the world there’s always going to be a presentation going on so if you do have a couple hours then your day to jump in please do but it will also be available later as well for viewing um on our youtube channel but again thank you guys so much for joining thank you michi and.

Talia and i hope everyone has a great rest of their day thank you bye

Roadmap planning can feel like a top-down process that’s focused on execution rather than the user problems that need solving.

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