Why Product Adoption Breaks Down — and How to Innovate Inside a Large Organization

Victoria Mensch: Welcome to Decisions at the Frontier. I am very happy and very excited to be joined today by Shiraz Cupala, VP of Product for Microsoft Teams Meetings. Across more than 25 years he has built and led innovation work at the intersection of technology and human experience, with a reputation for combining strategic vision, calm discipline and cross-functional execution. Shiraz, welcome. It's so great to have you here.

Shiraz Cupala: Thank you, Victoria. It's really great to be here, and thank you for that wonderful intro.

Victoria Mensch: Your career has spanned all these different areas within product. Can you tell us a little bit about your career? How has this shaped you, and what does it actually mean for you?

Shiraz Cupala: Absolutely. I have a confession: I'm a bit of a theater kid. I love the stories and the sets and the costumes and lights and sound — everything about theater. I've even produced shows and was on the board of a children's theater. But I'm not a particularly great actor. I did a little in high school and realized that was not my strength. The thing I love about it is creating magical experiences that bring people together. To me, innovation is about making the impossible possible, and I love doing that in dramatic ways that get people excited while fixing their problems and eliminating frustrations — all the things we do as product people. I love it because of the excitement and emotion it creates for people and the satisfaction of helping people. That's what keeps me going and loving this space.

Victoria Mensch: That's so beautiful, because innovation is about creativity in a lot of different ways. Did your relationship with innovation change over the course of your career? Maybe you stepped in for one reason and then realized something else, especially in the product area.

Shiraz Cupala: At the very beginning of my career, innovation was about business process — improving very specific processes to make people more efficient. That was interesting, and it was magical, but a lot of that magic was internally focused and internally impactful for companies. I wanted to have a more direct impact on people, so pretty early on I shifted to creating products that more directly touch people's lives, both individually and as groups. My focus shifted toward what's more fulfilling for people and connecting them with each other. And of course the technology space has changed so much over the last few decades that what we're able to do, and how we create those things, has dramatically changed as well.

Victoria Mensch: Did you find that your design background gave you a different angle than a pure product or engineering background would?

Shiraz Cupala: Yes. The most important part of building great products is understanding people. Most people assume that means know your customer, know your users, and of course that's essential — you can't do anything without understanding the customer. But you also have to understand everyone involved in making and delivering your product to be successful as a team. When you do that, you create products and plans that everyone can connect with emotionally. My design background is really about how I connect with people emotionally — whether that's designing the product, where I have a discerning eye for visual quality and an intuition for emotional impact, or convincing the team internally why this is the direction we should take. That has been critical in allowing me to create the products I have.

Victoria Mensch: I really like that you mentioned emotional connection and how people use the product. This is something we hear a lot from people who come through the academy: it's one thing to design a product — you've done all the research, you've connected emotionally, you have that intuitive understanding of how it should work and how it should help — but the adoption and usage of that product is a different challenge.

Shiraz Cupala: It's a dramatically different challenge. We can think we've designed this amazing product, and it may work for us and for a certain number of people, but then you hit the wall: a few people are using it, but more people aren't, or the few who are use it for a little while and then leave. That's where we have to go deeper and understand the real problem we're solving for a customer. Is it painful enough for them to change the way they're doing something? The customer wasn't doing nothing — they had some solution to that problem. We think we've got a better mousetrap. Is it really better? We have to understand the real friction they have, and whether we can overcome it enough to counteract the inertia of change. When we haven't analyzed that balance, that's when you start to have adoption problems and retention problems.

Victoria Mensch: Do you have any stories where it surprised you? You thought the product would have one kind of adoption among customers, and it turned out differently.

Shiraz Cupala: Yes. A number of years ago we built a feature in Teams where you could change the branding — the colors. I thought it was a cool feature, there was definitely some use for it, and customers would like it. What I did not anticipate was how passionate customers were about that capability. I've been doing product a long time and talked to tons of customers, and this one I missed: that brand color meant they were making the product theirs. They had such an emotional connection to their company, and their employees had that connection, and they wanted to project it to their team and their customers. I would sit down with IT executives at Fortune 500 companies and they'd tell me how passionately they loved the branding feature. I learned something, which was really delightful — we're always learning.

Shiraz Cupala: Early on, when I was at OfferUp, we wanted to make it simpler for people to pay for their purchases. This was before the simplicity we now take for granted with Venmo and Cash App. You had PayPal, but it was a little cumbersome, and people were primarily paying with cash. So we built a feature to pay through OfferUp. What we failed to anticipate were the cognitive barriers and trust barriers people have with effectively saying, “I'm going to give a stranger my credit card.” You're used to giving your credit card to a stranger in a store, but not to a stranger you meet on the street. That was one where we were ahead of where the market was.

Victoria Mensch: So that really required a dramatic change in behavior. Looking back at all your experiences, where does the transition from a beautifully designed product with a great user experience in the pilot setting to real adoption most commonly break down?

Shiraz Cupala: First of all, we oftentimes fall in love with our own solutions, and it's really important not to. Many of the greatest products out there were actually accidents: a company built a solution for its own team, it was really good, they started showing it to other people, a whole company was born, and they threw away their original product. So falling in love with a product isn't necessarily bad, but you have to listen to the customer and ask: I've got a few people using it — why are they using it, and why aren't other people? Then people run a survey or ask customers what works, what doesn't and why they use it, and assume whatever the customer says is the right answer. Users are notoriously bad at understanding their own motivations, and surveys can be very misleading. What I always tell my team is that you have to look past what they're saying to what they're thinking, to what they mean by that. You have to watch them. Oftentimes they'll say one thing and literally in front of you do the opposite in the next breath.

Shiraz Cupala: I'll use an example. AI is everywhere now; we're all trying to build products that take advantage of it. We designed the ability in Teams to have Copilot answer questions for you. You might be in a Teams meeting or a chat and need a piece of information, and you could just ask right there, the way you'd @mention a colleague. We enabled Copilot to be a participant in the chat and answer questions for you. It worked great for us; it wasn't perfect, but it was really useful. What we didn't take into account was that even internally within Microsoft, people were very cautious about using it, because they didn't know what it was going to answer and were worried about being embarrassed by the answer. In a group setting, if something goes wrong, you're not just frustrated — it makes you look bad. That's one of the challenges, particularly in meetings where it's happening in real time, and we're very thoughtful about it when we design our capabilities.

Victoria Mensch: From where you sit, what is fundamentally changing in how people collaborate nowadays?

Shiraz Cupala: Obviously people can be anywhere and collaborate, so that's a fundamental change. People also go back and forth between synchronous and asynchronous collaboration much more than they did even five or ten years ago. I might chat with someone or send an email, then we jump into a meeting, then we follow up afterwards, and that becomes a seamless form of collaboration. A lot of the time you may not even talk to the person — you send a message and they send something back, very quickly, with all the new tools we have. That changes how people communicate and how thoughtful they need to be: being clear so there isn't misunderstanding, and managing the overwhelm, because you can get so much communication.

Victoria Mensch: Given all that, what does it require from product leaders now when they look at product design?

Shiraz Cupala: The most important role for a product leader is making sure that everyone who needs to be part of that collaboration is included, is heard and participates in making the best thing you can. Everyone says that sounds great, but the product leader is uniquely positioned to be the go-between, the translator between all the different disciplines. The product leader has a role in understanding the business and the customer, but also in understanding all the players on the team — the designers, marketers, engineers, writers — everyone who will help design and build the solution. They don't all speak the same language. It's the product leader's job to bridge communication gaps, bring people together, and create the vision and the rally everyone gets motivated behind. Being able to motivate those teams around a direction is what the product leader role is really all about.

Victoria Mensch: You preempted my question. There's so much complexity, especially in large organizations, with so many roles and stakeholders participating in the success of the product. How do you coordinate all that to advance your vision of the product?

Shiraz Cupala: Early in my career, I'd have a vision and just start telling everyone, trying to convince everyone how great it was and why we should do it. A few people listened and got on board, and most people said, “I'm not so sure,” or “I've got a different idea.” The mistake I made was trying to convince everyone at the same time, and that's never going to work. Within an organization, just like with customers, you have early adopters, later adopters and laggards, and people who won't come on board until someone else has made the decision and says, “This is what we're doing now.” That's even more so in large companies, but it happens in very small companies too, like OfferUp. You need all those personalities to build a successful company and product. You start with the people who see your vision — not naysayers, but not people who tell you everything is perfect either. That's how you improve, hone and refine the solution. As you do that, you bring in newer voices, and fairly quickly you can get to the point where you've cracked the nut: you've solved enough of the questions and problems that the big middle says, “This actually makes sense, and I can come on board.”

Victoria Mensch: So that's how you build consensus. But there are always conflicting priorities within the organization, and the product vision you had in the beginning may not be fully realized. There are always trade-offs. How do you decide what gets in and what gets left out?

Shiraz Cupala: This is very, very hard. We have a collaborative note-taking feature in Teams meetings that we released four or five years ago. It was a very new capability, and there was a minimum set of capabilities we believed was required for users to adopt it — for it to be easy enough and valuable enough that they'd be excited to use it in their daily work. We were working with a number of different teams: the new Loop team, with its real-time collaboration technology (it's now called Pages), and the Outlook team, because sometimes you need to take notes ahead of time or draft your agenda. Not everyone could deliver on the timeframe we needed, or was aligned on the capabilities we thought were necessary for a complete feature. Without something complete, we were really worried it just wouldn't take off.

Shiraz Cupala: So there's a balance between what you believe is the ideal capability, what you think is the minimum, and what you practically can do — technologically and organizationally. Some teams have different priorities: “That's great, but it's fifth on our list, and we've got three other things to deliver in the next three months.” Getting through that took negotiating with them, with our leadership and with their leadership, and we had to compromise. The hardest compromise was the timeline. Everyone wanted to ship something fast, and my team was eager, but without that capability it just wasn't going to work. So we had to reset expectations internally. We could have shipped half a product and kept improving it over time, but I wasn't willing to do that, because you only get a few shots with customers to really delight them. I said, “This is going to take longer, but we're going to get what we need.” You have to figure out where you can compromise to reach the end goal. It took a lot longer than any of us wanted, but we ended up with something very strong that people really love.

Victoria Mensch: That brings me to another question: what does it take to innovate within a large organization? Sometimes the vision is dramatically different from the core of the organization. Our listeners ask all the time how you push for that innovation while making sure the core stays intact and keeps growing, and at the same time prepare for what's to come.

Shiraz Cupala: This is super hard. It's hardest in large organizations, but it happens in smaller ones too. The biggest mistake people make is trying to get their teams to do both at the same time. You take someone who owns a specific area and say: keep this area going, keep improving it incrementally, keep customers happy — and also come up with some breakthrough crazy innovation. That is a recipe for frustration and failure. Not because the people aren't smart, but because you've asked them to be of two completely different minds. The sustaining, iterating mindset is completely different from the throw-it-all-away, come-up-with-something-radically-different mindset. Many people can do both, but it's really hard to do them at the same time. We've tried it a few times and it was slow, and we as leaders were frustrated about why we weren't making more progress.

Shiraz Cupala: Our biggest successes have been when we sectioned off part of the team to think about a particular crazy, blue-sky problem. What I don't like to say is “we have an innovation team,” as if other teams aren't innovation teams. Everyone's innovating in some way. Even the team working on V5, V6 or V7 of a product is doing a different type of incremental innovation, and that's valuable and really exciting too. But when you're doing breakthrough innovation, you need to isolate that team and not meddle or get in their way, because they need to think about radical ideas you would normally reject so they can come up with something truly exciting. Then you figure out: we believe that's a winner — how do we make it happen within our existing context? Once you have the winner, something you're all excited about, it's much easier to ask how to make it work than to try to come up with something inside your existing framework. You just don't innovate enough that way. That's the innovator's dilemma, so to speak.

Shiraz Cupala: I'm not interested in high growth in a team like that. What I'm interested in is the retention rate. Even if you have five users, if they cannot live without that product, you've got something — that's interesting data. Then: how do you grow from five to ten to 50 to 100 to 1,000 to 10,000 to 10 million? That's the path you have to figure out. But I'd rather take…