Business Strategy

Should you try Google’s famous “20% time” experiment to encourage innovation? We tried this at Duolingo years ago. It didn’t work. It wasn’t enough time for people to start meaningful projects, and very few people took advantage of it because the framework was pretty vague. I knew there had to be other ways to drive innovation at the company. So, here are 3 other initiatives we’ve tried, what we’ve learned from each, and what we're going to try next. 💡 Innovation Awards: Annual recognition for those who move the needle with boundary-pushing projects. The upside: These awards make our commitment to innovation clear, and offer a well-deserved incentive to those who have done remarkable work. The downside: It’s given to individuals, but we want to incentivize team work. What’s more, it’s not necessarily a framework for coming up with the next big thing. 💻 Hackathon: This is a good framework, and lots of companies do it. Everyone (not just engineers) can take two days to collaborate on and present anything that excites them, as long as it advances our mission or addresses a key business need. The upside: Some of our biggest features grew out of hackathon projects, from the Duolingo English Test (born at our first hackathon in 2013) to our avatar builder. The downside: Other than the time/resource constraint, projects rarely align with our current priorities. The ones that take off hit the elusive combo of right time + a problem that no other team could tackle. 💥 Special Projects: Knowing that ideal equation, we started a new program for fostering innovation, playfully dubbed DARPA (Duolingo Advanced Research Project Agency). The idea: anyone can pitch an idea at any time. If they get consensus on it and if it’s not in the purview of another team, a cross-functional group is formed to bring the project to fruition. The most creative work tends to happen when a problem is not in the clear purview of a particular team; this program creates a path for bringing these kinds of interdisciplinary ideas to life. Our Duo and Lily mascot suits (featured often on our social accounts) came from this, as did our Duo plushie and the merch store. (And if this photo doesn't show why we needed to innovate for new suits, I don't know what will!) The biggest challenge: figuring out how to transition ownership of a successful project after the strike team’s work is done. 👀 What’s next? We’re working on a program that proactively identifies big picture, unassigned problems that we haven’t figured out yet and then incentivizes people to create proposals for solving them. How that will work is still to be determined, but we know there is a lot of fertile ground for it to take root. How does your company create an environment of creativity that encourages true innovation? I'm interested to hear what's worked for you, so please feel free to share in the comments! #duolingo #innovation #hackathon #creativity #bigideas

It’s easy as a PM to only focus on the upside. But you'll notice: more experienced PMs actually spend more time on the downside. The reason is simple: the more time you’ve spent in Product Management, the more times you’ve been burned. The team releases “the” feature that was supposed to change everything for the product - and everything remains the same. When you reach this stage, product management becomes less about figuring out what new feature could deliver great value, and more about de-risking the choices you have made to deliver the needed impact. -- To do this systematically, I recommend considering Marty Cagan's classical 4 Risks. 𝟭. 𝗩𝗮𝗹𝘂𝗲 𝗥𝗶𝘀𝗸: 𝗧𝗵𝗲 𝗦𝗼𝘂𝗹 𝗼𝗳 𝘁𝗵𝗲 𝗣𝗿𝗼𝗱𝘂𝗰𝘁 Remember Juicero? They built a $400 Wi-Fi-enabled juicer, only to discover that their value proposition wasn’t compelling. Customers could just as easily squeeze the juice packs with their hands. A hard lesson in value risk. Value Risk asks whether customers care enough to open their wallets or devote their time. It’s the soul of your product. If you can’t be match how much they value their money or time, you’re toast. 𝟮. 𝗨𝘀𝗮𝗯𝗶𝗹𝗶𝘁𝘆 𝗥𝗶𝘀𝗸: 𝗧𝗵𝗲 𝗨𝘀𝗲𝗿’𝘀 𝗟𝗲𝗻𝘀 Usability Risk isn't about if customers find value; it's about whether they can even get to that value. Can they navigate your product without wanting to throw their device out the window? Google Glass failed not because of value but usability. People didn’t want to wear something perceived as geeky, or that invaded privacy. Google Glass was a usability nightmare that never got its day in the sun. 𝟯. 𝗙𝗲𝗮𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗥𝗶𝘀𝗸: 𝗧𝗵𝗲 𝗔𝗿𝘁 𝗼𝗳 𝘁𝗵𝗲 𝗣𝗼𝘀𝘀𝗶𝗯𝗹𝗲 Feasibility Risk takes a different angle. It's not about the market or the user; it's about you. Can you and your team actually build what you’ve dreamed up? Theranos promised the moon but couldn't deliver. It claimed its technology could run extensive tests with a single drop of blood. The reality? It was scientifically impossible with their tech. They ignored feasibility risk and paid the price. 𝟰. 𝗩𝗶𝗮𝗯𝗶𝗹𝗶𝘁𝘆 𝗥𝗶𝘀𝗸: 𝗧𝗵𝗲 𝗠𝘂𝗹𝘁𝗶-𝗗𝗶𝗺𝗲𝗻𝘀𝗶𝗼𝗻𝗮𝗹 𝗖𝗵𝗲𝘀𝘀 𝗚𝗮𝗺𝗲 (Business) Viability Risk is the "grandmaster" of risks. It asks: Does this product make sense within the broader context of your business? Take Kodak for example. They actually invented the digital camera but failed to adapt their business model to this disruptive technology. They held back due to fear it would cannibalize their film business. -- This systematic approach is the best way I have found to help de-risk big launches. How do you like to de-risk?

Back on recession watch, Leading Indicator #2 – the FHA mortgage delinquency rate. This isn’t typically in lists of leading economic indicators, but it may be a proverbial canary in the coal mine in the current context. FHA borrowers have low to moderate incomes, with a median income of about $75,000 a year, and most are first-time homebuyers. Judging from the recent increase in the delinquency rate on FHA loans, these households are under mounting financial stress. This is despite the exceptionally low 4% unemployment rate and goes in part to the credit characteristics of the borrowers, including lower credit scores and downpayments. Even more important may be their high debt-to-income ratios. With mortgage rates and house prices as high as they are, borrowers have to shell out a big share of their income to their mortgage payment to get into a home. They may have gambled that rates would fall and could refinance, bringing down their payment. However, the Fed’s higher-for-longer rate policy and quantitative tightening have forestalled that exit strategy. Combine this with higher homeowner insurance premiums and property taxes, and borrowers struggle to make mortgage payments. What happens when the job market wobbles even a little bit? Thus, why this is a good statistic to include in our recession watch. Not that the financial troubles of FHA borrowers are enough to push the economy into recession. Indeed, high and middle-income mortgage borrowers are having no trouble making their payments at this time – the gap between the FHA delinquency rate and those on Fannie and Freddie loans has never been as large. But if the economy is headed for trouble, it is FHA borrowers who will signal it first. And they are. #rates #FHA #income #recessionwatch #fed

Innovation is only as valuable as the problem it solves. We live in an age where technological advancements move faster than our ability to strategically adopt them. It’s no longer a question of can we implement this? but rather, should we? The real challenge isn’t access to innovation. 𝐈𝐭’𝐬 𝐝𝐢𝐬𝐜𝐢𝐩𝐥𝐢𝐧𝐞. Discipline to pause before we purchase. Discipline to align tools with outcomes. Discipline to measure impact before we declare success. 𝐓𝐡𝐞 𝐃𝐫𝐢𝐯𝐞𝐫𝐬 𝐨𝐟 𝐭𝐡𝐞 𝐓𝐞𝐜𝐡 𝐏𝐚𝐫𝐚𝐝𝐨𝐱: • 𝐒𝐡𝐢𝐧𝐲 𝐍𝐞𝐰 𝐎𝐛𝐣𝐞𝐜𝐭 𝐒𝐲𝐧𝐝𝐫𝐨𝐦𝐞: The irresistible pull towards the ‘new’ and ‘novel’, often at the expense of sustained objectives and an overarching strategic vision. • 𝐅𝐞𝐚𝐫 𝐨𝐟 𝐌𝐢𝐬𝐬𝐢𝐧𝐠 𝐎𝐮𝐭 (𝐅𝐎𝐌𝐎): The anxiety that failing to adopt new technologies or trends could result in missed opportunities for growth or competitive advantage. 𝐓𝐡𝐞 𝐑𝐞𝐚𝐥𝐢𝐭𝐲 𝐂𝐡𝐞𝐜𝐤: • 𝟑𝟎% of App deployments fail • 𝟕𝟎% of Digital Transformation initiatives don’t meet goals • 𝟕𝟎%+ of manufacturers worldwide are stuck in pilot purgatory • 𝟓𝟖% of IoT projects are considered not to be successful • 𝟔𝟏% of manufacturers don’t have specific metrics to measure the effectiveness or impact of AI deployments 𝐀𝐝𝐯𝐢𝐜𝐞 𝐟𝐨𝐫 𝐭𝐡𝐞 𝐓𝐞𝐜𝐡-𝐂𝐮𝐫𝐢𝐨𝐮𝐬 𝐂𝐨𝐦𝐩𝐚𝐧𝐢𝐞𝐬: 1. 𝐀𝐬𝐬𝐞𝐬𝐬, 𝐃𝐨𝐧'𝐭 𝐀𝐬𝐬𝐮𝐦𝐞: Evaluate whether the technology fills a need or optimizes current operations before investing. 2. 𝐀𝐥𝐢𝐠𝐧, 𝐓𝐡𝐞𝐧 𝐀𝐜𝐭: Ensure that any new tech acquisition is in alignment with your strategic business goals. 3. 𝐌𝐞𝐚𝐬𝐮𝐫𝐞 𝐭𝐨 𝐌𝐚𝐧𝐚𝐠𝐞: Develop clear metrics or KPIs to track the success and relevance of your technology investments. 𝐅𝐨𝐫 𝐚 𝐝𝐞𝐞𝐩𝐞𝐫 𝐝𝐢𝐯𝐞 𝐨𝐧 𝐭𝐡𝐢𝐬 𝐭𝐨𝐩𝐢𝐜, 𝐢𝐧𝐜𝐥𝐮𝐝𝐢𝐧𝐠 𝐬𝐨𝐮𝐫𝐜𝐞𝐬:  https://lnkd.in/eX89kQ6n ******************************************* • Visit www.jeffwinterinsights.com for access to all my content and to stay current on Industry 4.0 and other cool tech trends • Ring the 🔔 for notifications!

In 2011, the Amazon Appstore failed on launch and Jeff Bezos was furious. It was my fault, and I handled one aspect of recovery so poorly that one of my engineers quit. I still regret it 14 years later. Please learn from my mistake. The main lesson is that when you are leading through a crisis, it can feel like it is all about you. It isn’t. It is about: 1) Solving the problem 2) Guiding your team through it The product issue was that there were some pretty simple bugs, and we solved those problem well enough that I was eventually promoted. Where I failed was in guiding my team through the crisis. My leadership miss was that I neglected to encourage and support the engineer who had written the bad code. He did a great job stepping up and supporting the effort to fix the problem, but shortly afterward, he resigned. During the crisis, I failed to make clear to him that we did not blame him for the launch failure despite the bugs. I imagine that left room for him to think we blamed him or that he didn’t belong. It is also possible that others did blame him directly and that I was too caught up in the crisis to realize it. Both instances were my responsibility as the leader of the team. His resignation taught me a valuable lesson about leading through a crisis: No matter how bad the situation is, your team must be your first priority. If you make them feel safe, they will move heaven and earth to fix the problem. If you don’t, they may still fix the problem, but the team itself will never be the same. As a leader, here is how you can give them what they need: 1) Take the blame and do not allow others to be blamed. In some bug cases after this we did not release the name of the engineer outside the team in order to protect them from judgment or blame. 2) Separate fixing the problem from figuring out why it happened. Once the problem is fixed, you can focus on root-causing. This lowers the risk of searching for answers getting confused with searching for someone to blame. 3) Realize that anyone involved in the problem already feels bad. High performers know when they have fallen short and let their team down. As a leader you have to show them the path to growth and success after the crisis. They do not need to be beaten up on- they have taken care of that themselves. 4) See crises and problems as growth opportunities, not personal flaws. Your team comes with you in a crisis whether you like it or not, so you might as well come out stronger on the other side. As a leader, the responsibility for a crisis is yours in two ways: The problem itself and the effect it has on the future of the team. Don’t get too caught up in the first to think about the second. Readers- Has your team survived a crisis? How did you handle it?

Great Board conversations don’t sell—they stretch your thinking. Having spent time both as a member of the management team working with the Boards and as a Board member myself, I’ve seen a few common pitfalls that even seasoned leaders fall into. Here are three that stand out: 1. Trying too hard to “sell” the strategy. Your job with the Board isn’t to pitch—it’s to inform. The goal is to create a regular rhythm of updates around the business, strategy, and execution. One of the fastest ways to lose credibility is to act like everything’s perfect. Every company—no matter how successful—has real challenges. Board members know this. Being candid about those challenges doesn’t make you look weak. It makes you trustworthy. Transparency matters. Your numbers already tell part of the truth. Bring the rest. 2. Keeping the strategic aperture too narrow. Executives often focus on operational detail and forget that Boards can be most helpful in widening the lens. Leverage their distance from the day-to-day as a feature, not a flaw. I cringe when I hear, “I need to dumb it down for the Board.” In reality, the best Boards raise the level of strategic thinking. Bring them into big questions: “What does our industry look like in five years? Where should we be positioned?” Boards are at their best when they help you challenge your assumptions and stretch your thinking. 3. Not asking for guidance. Some of the best advice I’ve ever received in my career has come from Board members. Don’t just report—ask. Tap into their experience. Invite their perspective. The Board appreciates humility, especially when you say, “I haven’t figured this out yet—I don’t have the answer. But what are the strategic issues you would consider if you were in my shoes?” Because here’s the truth: The smartest executives don’t try to impress the Board—they learn from it. And here are 3 things I’ve learned to always get from a great Board conversation: 1. Start with the commercial “why.” Boards aren’t there for a product roadmap walkthrough—they want to understand business impact. Always lead with the commercial dimension. Why does this matter for revenue, margin, competitive advantage, or long-term growth? When you start there, everything else has context. Your Board isn’t a stage—it’s your secret weapon. 2. Define what good looks like. One of the most helpful things you can do is to show what “great” would look like—clearly and with metrics. It gives the Board a benchmark to assess against, and it keeps the conversation focused on outcomes, not just activity. 3. Ask what you’re not seeing. The question I’ve found most consistently valuable: “What do you think we’re not thinking about as a management team?” You’ll be amazed at the insight that comes back. This invites perspective without defensiveness—and you’ll often uncover blind spots or strategic angles that weren’t even on your radar. Because Boards aren’t there to be dazzled—they’re there to help you see what you can’t.

Over the last year, I’ve seen many people fall into the same trap: They launch an AI-powered agent (chatbot, assistant, support tool, etc.)… But only track surface-level KPIs — like response time or number of users. That’s not enough. To create AI systems that actually deliver value, we need 𝗵𝗼𝗹𝗶𝘀𝘁𝗶𝗰, 𝗵𝘂𝗺𝗮𝗻-𝗰𝗲𝗻𝘁𝗿𝗶𝗰 𝗺𝗲𝘁𝗿𝗶𝗰𝘀 that reflect: • User trust • Task success • Business impact • Experience quality    This infographic highlights 15 𝘦𝘴𝘴𝘦𝘯𝘵𝘪𝘢𝘭 dimensions to consider: ↳ 𝗥𝗲𝘀𝗽𝗼𝗻𝘀𝗲 𝗔𝗰𝗰𝘂𝗿𝗮𝗰𝘆 — Are your AI answers actually useful and correct? ↳ 𝗧𝗮𝘀𝗸 𝗖𝗼𝗺𝗽𝗹𝗲𝘁𝗶𝗼𝗻 𝗥𝗮𝘁𝗲 — Can the agent complete full workflows, not just answer trivia? ↳ 𝗟𝗮𝘁𝗲𝗻𝗰𝘆 — Response speed still matters, especially in production. ↳ 𝗨𝘀𝗲𝗿 𝗘𝗻𝗴𝗮𝗴𝗲𝗺𝗲𝗻𝘁 — How often are users returning or interacting meaningfully? ↳ 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 𝗥𝗮𝘁𝗲 — Did the user achieve their goal? This is your north star. ↳ 𝗘𝗿𝗿𝗼𝗿 𝗥𝗮𝘁𝗲 — Irrelevant or wrong responses? That’s friction. ↳ 𝗦𝗲𝘀𝘀𝗶𝗼𝗻 𝗗𝘂𝗿𝗮𝘁𝗶𝗼𝗻 — Longer isn’t always better — it depends on the goal. ↳ 𝗨𝘀𝗲𝗿 𝗥𝗲𝘁𝗲𝗻𝘁𝗶𝗼𝗻 — Are users coming back 𝘢𝘧𝘵𝘦𝘳 the first experience? ↳ 𝗖𝗼𝘀𝘁 𝗽𝗲𝗿 𝗜𝗻𝘁𝗲𝗿𝗮𝗰𝘁𝗶𝗼𝗻 — Especially critical at scale. Budget-wise agents win. ↳ 𝗖𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻 𝗗𝗲𝗽𝘁𝗵 — Can the agent handle follow-ups and multi-turn dialogue? ↳ 𝗨𝘀𝗲𝗿 𝗦𝗮𝘁𝗶𝘀𝗳𝗮𝗰𝘁𝗶𝗼𝗻 𝗦𝗰𝗼𝗿𝗲 — Feedback from actual users is gold. ↳ 𝗖𝗼𝗻𝘁𝗲𝘅𝘁𝘂𝗮𝗹 𝗨𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱𝗶𝗻𝗴 — Can your AI 𝘳𝘦𝘮𝘦𝘮𝘣𝘦𝘳 𝘢𝘯𝘥 𝘳𝘦𝘧𝘦𝘳 to earlier inputs? ↳ 𝗦𝗰𝗮𝗹𝗮𝗯𝗶𝗹𝗶𝘁𝘆 — Can it handle volume 𝘸𝘪𝘵𝘩𝘰𝘶𝘵 degrading performance? ↳ 𝗞𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲 𝗥𝗲𝘁𝗿𝗶𝗲𝘃𝗮𝗹 𝗘𝗳𝗳𝗶𝗰𝗶𝗲𝗻𝗰𝘆 — This is key for RAG-based agents. ↳ 𝗔𝗱𝗮𝗽𝘁𝗮𝗯𝗶𝗹𝗶𝘁𝘆 𝗦𝗰𝗼𝗿𝗲 — Is your AI learning and improving over time? If you're building or managing AI agents — bookmark this. Whether it's a support bot, GenAI assistant, or a multi-agent system — these are the metrics that will shape real-world success. 𝗗𝗶𝗱 𝗜 𝗺𝗶𝘀𝘀 𝗮𝗻𝘆 𝗰𝗿𝗶𝘁𝗶𝗰𝗮𝗹 𝗼𝗻𝗲𝘀 𝘆𝗼𝘂 𝘂𝘀𝗲 𝗶𝗻 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝗷𝗲𝗰𝘁𝘀? Let’s make this list even stronger — drop your thoughts 👇

Your influence in the board room and executive team is 90% communication with measurable examples. The words you use can make or break you. Naturally, I've been compiling a list of "instead of saying this, say this" with measurable results. Many are based on my gotcha moments where I've failed miserably at explaining what marketing does. I've said things like: “We’re increasing brand awareness.” “Our demand generation efforts are working.” “We’re improving our SEO strategy.” Every marketing leader has said some version of these. The problem? Nobody in the boardroom or executive team cares about (or understands) marketing buzzwords. They care about revenue, efficiency, and business impact. Let's flip the script. I've compiled a list of marketing-speak and translated these statements into terminology a room full of non-marketers would understand. And bonus, I've included the right metrics to back them up. Example: 🚫 Don’t say: “We’re generating a lot of leads.” ✅ Say this instead: “We’re bringing in people who are actually interested in buying.” 📊 Measure it with: Organic Traffic, Demo Requests, MQL-to-SQL Conversion Rate I put together a full table of these translations and a template so you can ensure your marketing efforts land in the boardroom. I'll share the list and other communication tips this weekend in my newsletter, but if you just want the table. Let me know. Drop a “TABLE” in the comments, and I’ll send it over.

New CMO: We're moving 50% of the marketing budget to brand / top of funnel. VP Growth: Hell no. My ROAS will drop, and my bonus depends on hitting a ROAS target. New CMO: Not anymore. Your bonus is tied to two metrics: 1. Total contribution dollars generated by the business (at 35% contribution margin). 2. Contribution dollar lifetime value (rolling 30, 60, 180, and 365 days) for our owned business. VP Growth: wtf?! How can I own this? New CMO: Metrics aren't about individual ownership—they're team-driven. The real challenge is choosing the right ones. VP Growth: How do we know these are the right metrics? New CMO: The right metrics grow business health and fundamental enterprise value. If we increase these metrics, while keeping fixed costs flat, we become more profitable. Are they perfect? Maybe not. But they're miles better than short-term ROAS or new customers acquired, which have far less of a direct connection to fundamental business health when we increase those numbers. VP Growth: How can you say that? New CMO: For ROAS, you can hit any number by: 1. Spending less. 2. Doubling down on branded keywords, existing customers, or retargeting. 3. Running more discount events. But ROAS lacks incentives to drive incremental revenue—what actually grows the business—and says nothing about the cost to generate it. And for new customers acquired, there is no notion of customer quality. A massive sale drives high ROAS but attracts discount hunters who won't buy at full price unless we run bigger sales. Both of these metrics lack context on quality and long term profit, which is ultimately the fundamental goal of business. VP Growth: Ok, I'll buy that, but how can I be responsible for overall contribution dollars? New CMO: As a singular individual, you can't. That's why half of your budget will now be based on team performance. For you though, it'll drive you to make better decisions with how you spend our marketing dollars VP Growth: What do you mean? New CMO: You're free from short-term ROAS pressure to pad stats and can focus on incremental profitable growth. You can step back and do the things you know are right to drive net new incremental demand (meaning: you would not have gotten that revenue if you didn't spend that ad dollar) even if it's low ROAS. VP Growth: And the mythical purse string holders are bought in? New CMO: Yup - the CFO and board now understand that the real goal for our marketing investments is both short and long term incremental contribution dollar generation at the highest possible contribution margin. That was my one condition for agreeing to accept the offer to join VP Growth: Well butter my biscuits, let's do this. New CMO: Please never say that again

Most change initiatives don't fail because of the change that's happening, they fail because of how the change is communicated. I've watched brilliant restructurings collapse and transformative acquisitions unravel… Not because the plan was flawed, but because leaders were more focused on explaining the "what" and "why" than on how they were addressing the fears and concerns of the people on their team. People don't resist change because they don't understand it. They resist because they haven't been given a compelling story about their role in it. This is where the Venture Scape framework becomes invaluable. The framework maps your team's journey through five distinct stages of change: The Dream - When you envision something better and need to spark belief The Leap - When you commit to action and need to build confidence The Fight - When you face resistance and need to inspire bravery The Climb - When progress feels slow and you need to fuel endurance The Arrival - When you achieve success and need to honor the journey The key is knowing exactly where your team is in this journey and tailoring your communication accordingly. If you're announcing a merger during the Leap stage, don't deliver a message about endurance. Your team needs a moment of commitment–stories and symbols that anchor them in the decision and clarify the values that remain unchanged. You can’t know where your team is on this spectrum without talking to them. Don’t just guess. Have real conversations. Listen to their specific concerns. Then craft messages that speak directly to those fears while calling on their courage. Your job isn't just to announce change, but to walk beside your team and help your team understand what role they play in the story at each stage. #LeadershipCommunication #Illuminate