Roadmaps Unveiled: Lessons from Successes, Failures, and the Crucial Role of Stakeholder Buy-in

Teresa Cain at UXDX EMEA. Video: https://youtu.be/R-VkFBGId8A

Readable transcript: edited from the recording's captions for readability (fillers and false starts removed, punctuation and section headings added). Wording is the speaker's own. Timestamps are positions in the video. Names marked [?] could not be verified against the audio.

What a roadmap is and why it matters

[00:00:00] Good afternoon. I know I'm what's standing between you and Irish coffees, so we'll have some fun. I'm Teresa Cain, I'm the director of product, UX and design at TreviPay. We are a global fintech that processes 7 billion in transactions a year, and we have around 27 engineering teams and over 100 million in revenue a year, so it's a pretty exciting time to be in fintech.

[00:00:28] Have you ever had a roadmap fail and never understood why? Today we're going to talk about the successes and failures of roadmaps and the crucial role of stakeholder buy-in.

[00:00:45] The most important part of the roadmap process happens before you begin building your roadmap. This quote is from Jim Semick. How many of you have ever used ProductPlan before? Raise your hand. Not many people. It's a great roadmapping tool if you're new to roadmapping tools. ProductPlan is similar to Aha and some other tools out there. I couldn't agree more with Jim. I used this tool for a few years, and now we're going to dive into some of those successes and failures.

[00:01:18] So what is a roadmap? Roadmaps really allow you to communicate your strategy and vision to stakeholders. However, they're not one size fits all. It's really a methodical way to balance financial impact with strategic fit at your organization, and this is something a lot of product managers and organizations struggle with.

[00:01:42] Some of the key elements of a roadmap are really the strategy and how you execute it with tactics. The strategy ties to your vision. This is usually influenced by research and ties to KPIs, or key performance indicators. The tactics then tie to your strategy, so there's usually clear tasks that you're executing on. And our favorite word of OKRs, coming off that last presentation where no one likes them: objectives and key results are really tied to those tasks that you're executing on from a KPI standpoint.

[00:02:16] One of the KPIs we have as an organization at TreviPay is to increase user adoption. Over the last five years, even during the pandemic, I've been able to have the team increase user adoption by over 200% per year, and that is a KPI that we set as an org. The OKRs that I have the teams on product, UX and design tied to that are really around different research projects. We actually conducted over 50 UX research projects last year alone, and we're on track to hit around the same for this year, for 2023, and these different OKRs tie directly into our goal of increasing user adoption.

[00:03:02] If you don't use these at your organization, one of the key differences between these is the intention behind the goal. I won't go into it too much because it sounds like no one likes OKRs here, but if you're not using these today this is really a great way to get executive buy-in, when you tie your roadmap into your KPIs or OKRs. Your ultimate goal with your roadmap is really to drive results. To drive the best results you want to make sure the vision for your roadmap aligns with your company mission and values. If you're not tying your roadmap to KPIs or OKRs, if you can tie them to your company mission and values, this will again allow you to get that executive buy-in.

Problem one: the roadmap doesn't tie to the company mission

[00:03:51] So ultimately, why do roadmaps fail? When you think of failures of a roadmap, you might think it's too long, too short, too strategic, not enough detail. Maybe it was thrown together last minute. Maybe a customer has driven your organization to conduct and work on roadmaps and you kind of had to create one out of the blue. But these are really all superficial responses to the real reason why roadmaps fail, and the real reason roadmaps fail is lack of stakeholder buy-in. So we're going to walk into some more failures of what goes on beyond that here.

[00:04:36] First problem: the roadmap doesn't tie into the company mission and goals. If your roadmap doesn't align with your company mission and goals, good luck getting funding for your project. You want to make sure you have buy-in at every level of the organization, whether it's from your executive team, maybe a board that you have sitting on there. And if you're a startup this is even more critical, as you're really setting that mission for your organization as an entrepreneur, and you want to make sure you have a very clear statement in mind for where you're going as an organization.

[00:05:13] A key solution here is making sure you're establishing a roadmap vision that ties in with your company mission and values. So let's look at our mission and values at TreviPay. Our purpose is, we help businesses grow. Our vision is to bring innovation and payment expertise to every business in the world. And our mission is to make B2B payments easier, faster and smarter. For those that haven't heard of TreviPay, we process 7 billion in transactions annually across 27 different countries. We have over 27 engineering teams and over 40 product managers, UX researchers and designers.

[00:05:57] There is not a single feature that we work on as a team that does not tie to our company mission and value. If it did, it would never get approved from a roadmap standpoint. So this is something that has allowed us to not only have success with the 200% user adoption I mentioned, but even during the COVID pandemic we've been able to grow our revenue by over 20% per year. Being fluid and making sure that you're tying into either your purpose, vision or mission goes a long way, not just to get buy-in internally but externally with your customers as well.

Problem two: the organization doesn't believe in roadmaps

[00:06:34] Problem two: the organization doesn't believe in roadmaps. Sounds kind of funny, doesn't it? I actually worked for a healthcare organization a couple of years ago and they hired me to take over and bring them into a brand new healthcare market. On my first day I asked the chief strategic officer, well, where's your roadmap? Maybe I should have asked that during the interview process. And he says to me, oh, we actually don't believe in roadmaps, we don't do them here. So first day, I was like, well, why? And he said, we've never been able to hit a deadline and deliver on a roadmap ever as an organization, so we've banned them.

[00:07:14] So I challenged the chief strategic officer, which might have been a little ballsy for a first day, but I didn't get fired so it was the right decision. I challenged him and I said, let me change your mind and let me show you how to really get the value out of roadmaps in a different way than you've been doing them before.

[00:07:35] What I was able to do, and the solution here, is you want to make sure you're inspiring the organization to show the value of roadmaps. Here's an example of how I did it. If you look at the problem here, I've obviously had to change a little bit of my roadmap, but you can see the healthcare essence here. The problem was the organization really had a strictly waterfall method, focusing on the delivery of priorities. One of the challenges with this organization is customers were asking and begging for a roadmap, sales was begging for a roadmap, and the new board of executives was begging for a roadmap. They needed one to be successful internally and externally.

[00:08:17] So one of the solutions I came up with was putting together just a targeted 12-month roadmap, and you'll notice a disclaimer at the bottom of the roadmap: dates subject to change. That was part of how I got the executive buy-in, because let's be honest, roadmaps cannot be static. It is nearly impossible, especially in a climate of COVID-19 pandemic and tech layoffs, to not have a changing roadmap. So this allowed me to not only get executive buy-in but also allowed us as an organization to deliver a roadmap to customers that set a nice pace as well, to keep them happy.

Problem three: not diversifying your roadmap

[00:08:56] Problem three: not diversifying your roadmap. You want to make sure when you're building a roadmap that you're not only including feedback from customers and stakeholders, or just keeping the lights on for your product, but that you are filling in competitive gaps and staying innovative in the industry. I talked a minute ago about tech layoffs. When I started at TreviPay five years ago there were five competitors in the market. Today we have over 50. That's in a five-year period. If you are not diversifying your roadmap you are missing out on the opportunity for revenue and the opportunity to stay relevant.

[00:09:42] A great solution here is to make sure you diversify your roadmap just like you would an investment. If you had $10 million, how would you spend it? What area of the business would you invest that money in to make sure you were going to be around in one year, three years, five years or 20 years?

[00:10:03] So this is an example roadmap investment we strive to hit at TreviPay, and this is a method I have used not just at TreviPay but one I've used in strategy consulting over the last 16 years as well. Thinking about that $10 million, you want to make sure you're investing in enriching your business or product, which is a fancy way to say maintenance; filling competitive gaps; expanding into new verticals; innovation; and integrations and partnership. When you focus on a mix like this, or target a mix like this, you're going to be able to grow and enhance your roadmap in different ways than you have before.

[00:10:44] Some of the things that organizations struggle with is being able to do the same thing over and over again. I mentioned we have 27 engineering teams at TreviPay. Sometimes the roadmaps are staying stagnant, you're doing the same thing over and over again. When we put this process in place it allows us to make sure that we are keeping a velocity for our engineering teams to be able to work on some of these items every single time. So if you're not doing a mix exactly like this, hopefully this mix will inspire you to put some different features of innovation into your roadmap.

[00:11:20] Another way you can diversify your roadmap is by, perhaps you have a three or five year plan as an organization to be the leader in the space. Your year one could be focusing on enriching the platform, year two integrations, year three expansions, year four being a leader. So this is another way you could look at creating a strategic roadmap that also diversifies, and especially if you're trying to tie that into KPIs versus OKRs.

Problem four: not validating your roadmap with stakeholders

[00:11:51] Problem four: not validating your roadmap with stakeholders. Feedback is a gift. You're going to get both positive and negative feedback, but this is a crucial step in creating a roadmap that a lot of product managers miss. One of the key things we do at TreviPay is we have every stakeholder for each product manager maintaining a top five list. I mentioned 40 product managers, UX researchers and designers. Every single one of the product managers has a top five list for stakeholders across the org. For some of them this could be up to 15 different stakeholders across different departments.

[00:12:33] And every single quarter we run what's called a quarterly steering, where we are validating and revalidating our roadmap with all these stakeholders for their top five list or any other items that come up as well. So if you're not conducting a steering as an agile ceremony, or any other method that you're using at your organization, you want to find some way that you have constant engagement and connection with your stakeholders, to make sure you're constantly validating and confirming not only with your internal stakeholders but also before you go to your customers and with your customers as well.

[00:13:13] So we talked about the solution. Getting feedback at every level of the organization is one way to get around this. If you're not familiar with how to go about selling this vision to stakeholders, what I'm providing here is an example of how you could go about selling your vision. One of the things when I came into TreviPay five years ago, I found that a lot of product managers were really nervous about going and presenting to the executive team, so I put a method like this together to be able to inspire them to show data and prove the elements that are in the roadmap.

[00:13:49] As part of that, the key thing I want you to take out of the slide is you want to make sure you're talking to stakeholders about the opportunity in the vision. This is the vision for your roadmap that's tying to your company mission and goals. This is how you get buy-in, and why you have this meeting and discussion is you want their buy-in to be able to get this roadmap approved, and you want them to be champions of your product. That's really the key element of stakeholder feedback: you want more champions of your product for it to be successful.

[00:14:23] Some other elements of selling this vision are reviewing personas, competitive analysis, creating a strategic ecosystem of where you sit in the market, brainstorming roadmap ideas. One of the things that we do a lot of internally, I know those that went to New York heard me talk about two-hour design sprints, so we validate a lot of features on our roadmap with that process, and that is another data point you could use when validating features on your roadmap. And then ultimately what you're getting here is the roadmap buy-in.

Problem five: not understanding your target audience

[00:14:59] Problem five: not understanding who your target audience is. This is really a key element that a lot of product managers struggle with. If you're not constantly validating with your customers and understanding the market, that could be a challenge. So let me tell you about some of the challenges I have at TreviPay. I mentioned TreviPay is a global B2B fintech. We're in many industries, but primarily we're in retail and automotive. So two of my key clients that I talk quite a lot about are GM and Best Buy. When we go to create new product features at TreviPay we need to make sure we're meeting the needs of two different verticals, Best Buy and GM. If not, we wind up building custom solutions instead of actually integrating into a SaaS solution.

[00:15:53] So when you think about your target audience, you might be thinking about it in different verticals or different types of customers, such as a power user, an admin role, or other levels that would log into your products and solution. These are a couple of different ways to be thinking about how you can understand your target audience. What you want to do here is you want to make sure that you confirm who will get the most value out of your roadmaps.

[00:16:20] A couple of ways to do this is user personas. I'm a big fan of user personas. These are actually two live user personas we use at TreviPay. We actually have over 40 user personas at TreviPay. I mentioned we're in multiple industries: retail, automotive, e-commerce, marketplaces. We have a lot of different personas that we're trying to meet the needs for. When we tie user personas into our roadmap, into our processes, this really allows the stakeholders to connect who is getting the value. It also allows you to further validate your features by including and knowing who your target personas are for your roadmap. When I do this I usually have the team pull in who the persona is for every single element in the roadmap, just like you would a feature in Jira or any other tool.

[00:17:12] If you're not familiar with buyer personas, this is an element you might work on with marketing, or you might be doing on your own in product depending on how big your organization is. This is really a way to understand how the customer behaves in making their decision process. The customer that is buying your product may be different than the one that is using your product, so buyer personas are really critical in making sure you're really focusing on all levels of different personas.

[00:17:42] And for those that weren't at the New York UXDX here a couple of months ago in May, a lot of folks did not like user personas, so I want to make sure I include jobs to be done for those that are not fans of user personas. Jobs to be done are really a great way to identify customer problems and needs, and it takes a lot less time than the research that's done for user personas, so I want to make sure you have that option.

[00:18:13] I mentioned design sprints. We use a process at TreviPay that is called the two-hour design sprint process. We use a lot of different processes, we conduct a lot of UX research methods and research projects throughout the year. I mentioned we're going to hit around 50. We will have landed on around 32 two-hour design sprints by the end of this year. One of the ways that we're using this method is we are validating roadmap features to get stakeholder buy-in and bring the solution to customers faster.

[00:18:45] What we noticed is when we have the data and solution from a two-hour design sprint, we're able to show that data with the stakeholder. On top of that, the best thing that we do is we actually pull the stakeholders into the process to get their buy-in ahead of time. For instance, you have a CEO. I know earlier we were talking a bit about a CEO having access to Figma. I've certainly had that problem at a few companies. So in this element, actually involving the CEO in the process sometimes can help, to make sure that they're not taking it over later on at a different time.

Problem six: not updating your roadmap

[00:19:24] Problem six: not updating your roadmap. You can't make a static roadmap, it's not realistic. Look at the COVID-19 pandemic and the changes that happened with it. Again, the tech layoffs that are going on. You want to make sure that you're staying relevant with your roadmap and you're responding to the times.

[00:19:47] The COVID-19 pandemic for many of our clients was a big disruptor. I talked about Best Buy, who is well known for their retail in-store experience. A lot of the solutions we had to build had to switch to an e-commerce marketplace model. Even though they were live already with that, we had a lot of work to be able to draw the user base into an e-commerce model. So you want to make sure you're not just looking at what you have planned, but you're looking into the future of what you should be thinking about with your roadmap.

[00:20:22] One solution here is making sure you're validating your roadmap quarterly and communicating the updates with your stakeholders. I mentioned we conduct quarterly steerings at TreviPay, so every single product manager is meeting with every single stakeholder once a quarter to validate their top five list. It doesn't mean it'll make it in the roadmap, but they're validating it. And then as a group each quarter we vote as a team interactively on what priorities are going to go into the roadmap. So every single quarter is a chance for every stakeholder to raise their hand and say, I disagree with that, here's why we need this in the roadmap.

[00:21:03] For those that aren't familiar with waterfall versus iterative methods, there are still a lot of companies using waterfall. Most are using iterative now, but there are still a lot using waterfall. So one of the things I want you to think about here is if you're an organization that has migrated back to more waterfall methods, there's still a chance for incremental delivery within that process if you're not in an agile method, by working in that same cycle of that feedback loop. At TreviPay we are an agile tech shop, as agile as we can be, so we have a lot of Kanban teams as well. This really allows us to not only work in that quarterly feedback, but we're also able to make changes every two weeks, which we have a two-week sprint cycle. So this is a really critical part of being able to incorporate that feedback no matter what software development life cycle you use, or SDLC.

[00:22:06] One of the things that we've really moved to lately is collaborative tools to increase engagement on our roadmaps. We recently migrated the entire team over to Figma from Adobe and Sketch, and with that we've actually been piloting FigJam since April of 2021 as an organization, which is now out of beta and live. With that we've actually been using tools like Figma to really build our roadmaps out and get not just asynchronous feedback but feedback on the fly during meetings and workshops.

[00:22:41] We have a couple of different types of roadmaps. One I have on the screen there is a five-year strategic roadmap. It's got made-up data in it obviously. I would get my hand slapped for that if I showed a real roadmap. In addition to that we also have a very aggressive roadmap. I mentioned the 27 teams we have, so every single team has a roadmap, and this is something we have planned out for 12 to 18 months. And then we also have larger strategic roadmaps, and we use these in our processes to make sure we're getting the iterative feedback in that constant feedback loop.

[00:23:18] So what I want you to really take away here is how can we learn from the failures of roadmaps through the opportunities of how we get to that feedback. You could have the best looking roadmap, but if you're not getting stakeholder buy-in it's not going to be successful. If you don't tie into your company mission and value you could be missing opportunities with your roadmap. So what I want you to take away here is to be able to sell the value of your roadmap and communicate it out with your stakeholders on a regular basis.

[00:24:00] And I also want to end with a quote here, since I started with one: "It's all fine and good to have vision, it's all fine and good to know your why, but if you can't execute it then it's no value whatsoever." For those that are a fan of Simon Sinek's book Start With Why, if you don't take the opportunity to get feedback and correctly execute on your roadmap, there's missed opportunity. So I hope that inspires you to execute and make changes to your roadmap process. And I'd love to stay connected, so always open to questions. Thank you.

Q&A

[00:24:40] Host: What would be maybe your top tip for getting stakeholders to update the roadmaps?

[00:24:48] Teresa: My top tip to encourage stakeholders to update the roadmaps. To get the stakeholders to update the roadmaps, sorry, I had a flutter in my ear, so this is where we do the comedy part. No, I'm just kidding. Yeah, I think really the top tip here is you kind of have to hound your stakeholder. That's one of the key elements. Stakeholders are called a stakeholder for a reason, they're waiting for you to reach out to them, so you want to make sure that you're constantly engaging. And if they're not participating you need to go after them. We're a hybrid organization, we have remote and in-person and hybrid team, so that's the challenge. You need to use the means to be able to go after and create that relationship with your stakeholders.

[00:25:36] Host: Fantastic. I know you have a book on it, but could you answer the question, how does the two-hour design sprint work? We don't have enough time for that. No, I'm just kidding.

[00:25:46] Teresa: There is a book, I published a book earlier this year called Solving Problems in Two Hours, which is on the two-hour design sprint method. There's also a free template on the FigJam community as well if you just want to see what it looks like. But really the intent of the two-hour design sprint method is, as an organization, even before the COVID-19 pandemic hit, I had reduced design sprints down to either half a day or a day, because ultimately what happens is a lot of organizations look at these three-day or five-day design sprints as, we're going to do two or three a year and it's going to cost us 50 grand. The problem there is you're waiting three or six months to solve problems.

[00:26:26] Teresa: Well, I mentioned what was going on in the fintech space. We had five competitors when I started there and we have over 50 now. I don't have six months to solve problems. So part of the two-hour design sprint method that I created was really meant to solve problems quicker, and I was fortunate to be able to pilot it out at TreviPay since I was working on a master's and it was my project. That was kind of the point there. Luckily I was able to prove my thesis correctly. But ultimately that is the method: how can you solve problems faster to stay relevant as an organization.

[00:27:01] Host: Okay, it's a bit of fear there, right? You want to stay relevant, you want to stay ahead, but then you're also showing that people can go faster so we should too. Yep, nice. So if all your features and initiatives are so tightly coupled to your mission and vision, how do you challenge said vision and mission in your company?

[00:27:19] Teresa: How do you challenge the vision? Yeah, well, when you have that answer, let me know. No, it's a struggle. Most of the organizations I have worked for have always set three to five year visions. I also am a startup coach, so a lot of the startups I work for actually don't even have a vision. For some organizations, depending on your size, it could just be setting that vision and mission as an organization or a smaller company or entrepreneur. But for these larger organizations, hopefully you work for an organization that wants you to challenge the mission and values.

[00:27:54] Teresa: In fact, when I was at TreviPay a couple of years ago they had all of us, all the executive team, in a room together and they had us challenge what ended up being our mission and values. What they learned is we did not agree with what the board had put together, so they just ended up creating it anyways. But they took our feedback. You should feel comfortable to challenge that, and if not, have the data to feel confident in doing it.

[00:28:24] Host: No, I like that. I mean, I worked for a company where our mission became the mission of another competitor and we were like, hmm, were they inspired, or is everyone working on the same thing? And ultimately the mission was too big, so essentially you couldn't get it done in three years. I like when companies actually readdress their vision every two, three years, because the market changes. If your mission statement is from 1999, no offense, but if you haven't hit it now you need to adjust it so it's a bit better, something you're actually going to achieve at some point in your company's lifetime. You know, Johnson and Johnson, let's say if theirs was to cure the world. Yeah, don't do that, because good luck curing the world of every possible thing. Maybe something that's a bit more short-term. Short-term could still be five, six years. Yeah, absolutely.

[00:29:07] Host: Let's take this: so how much of what is 12 to 18 months out on your team roadmap actually gets implemented?

[00:29:14] Teresa: Great segue. So around 70%. I would say around 30% of the roadmap is shifting, and it's not without work. This is part of this quarterly steering process of actively looking and updating. So every single quarter around 70% gets executed. And I couldn't say more high things about the engineers and designers and product team. All this is because of the team, so I'm a leader but they do all the work. I would say that having a great team of a bunch of smart people also helps as well. But 70% is a pretty good number. If we could be higher it would be even better, honestly, so maybe a good KPI or OKR for next year.

[00:29:56] Host: Nice. Let's take: do you take a different approach for roadmaps when dealing with live products versus new product development?

[00:30:06] Teresa: Yes. I think there is a lot more opportunity for creativity when you have new products and innovations in the market. I have a mixture of legacy products that have been around for 40 years and have done migrations, and I also have new product development going on. So I think from a risk standpoint you can take a little more risk with a new product, because you're looking into that market and opportunity and you're looking to draw new revenue. When you have a legacy product that you have a large set of customers for already, it's much harder to go be wild with integrations and different features.

[00:30:42] Teresa: Let's take ChatGPT for instance. We got a lot of feedback that our users want ChatGPT everywhere, let's just integrate it everywhere. Well, we work in the highest fraud industry in fintech, so that's probably never going to happen. So that's something where you say, okay, let's take that feedback, and how do we integrate AI to really solve the problem they're looking for and give them what they need, but also maintain what we're doing as an organization from a security standpoint? That's a little bit of root cause analysis on some of these requests for specific things that maybe don't apply just yet.

[00:31:20] Host: So how do you strike a balance between abstract and concrete roadmap items?

[00:31:25] Teresa: Yeah, that is a really tough one, and that's really where a process like two-hour design sprints or other UX methods like lean canvas really come into play. You're going to have your more strategic items and you're going to have your items that are a little more detailed, so you need to have a fine balance. Usually I will create both a strategic roadmap and a tactical roadmap for the teams. That really strikes a different audience of whether I have a customer-facing roadmap or I've got something that's a little more internal. For instance, I don't know if you guys have a sales team that likes to sell things that you don't actually have, so I'm really careful what we end up giving the sales team, for instance.

[00:32:06] Host: So let's go with one more question. Considering that roadmaps are often tied to waterfall methodology, how do you respond to important insights when you have quarterly meetings? Can you kill ideas or give life to new ones in time?

[00:32:19] Teresa: Absolutely. I hate to say this out loud, but yes, we have to kill ideas, and that's the whole idea. The world of waterfall was meant for a static roadmap. That is really not a possibility now, kind of just like the move to a five-day design sprint down to a two-hour design sprint. Organizations don't have time to really set one roadmap for 12 to 18 months and leave it alone. If you executed on the same roadmap and didn't make any changes over 12 to 18 months, you would probably have a competitor that added 10 new features and be losing customers by the day. So I think that's really the opportunity you have to look at: you have to not think of a static roadmap, you need to be agile with it just like you do with agile methods with your engineering teams.

[00:33:10] Host: Certainly, I totally agree. I think oftentimes I think about maybe the working backwards model, where let's say you design what the roadmap would look like a year or two years in advance and you test it today. If you took that same prototype six months into the roadmap the customers won't be as happy, because the market landscape, the options they have, will have changed. I'm super happy with Tesla, the beginning of Tesla when they're the only option. Now when there's nine different EV companies with the same price with the same level of luxury on the market, maybe my NPS score for Tesla goes down. Maybe it goes up if you keep launching new ones. But maybe if you keep the exact same product, for example the Model X, the first one they had is around eight years old now and they've done very, very few changes to it, it scores lower in the minds of consumers. So your roadmaps are also probably going to score lower if they don't change with the times. The good news is the price keeps dropping, so that's how they keep their NPS score: big margins, fake discounts. All right, thank you so much, Teresa.

[00:34:09] Teresa: Thank you.