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Published · transcript-backedAishwarya Naresh Reganti: evaluation
11 Jan 2026 Lenny's Podcast Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon
“The second one is the culture itself. And again, I work with enterprises where AI is not their main thing and they need to bring in AI into their processes just because a competitor is doing it.”
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- Speaker
- Aishwarya Naresh Reganti
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- Verified speaker
- Claim type
- evaluation
- Recorded
- 11 Jan 2026
- Publisher
- Lenny's Podcast
Transcript context
…Sweet. I always like the optimistic perspective. I'm excited for you to listen to this and see what you think because it's really interesting. And to your point, there's a lot of things to focus on. It's one of many things to worry about and think about. Okay, let's get back on track here. So we've shared a bunch of pro-tips and important piece of advice. Let me ask, what other patterns and kind of ways of working do you see in companies that do this well and teams that build AI products successfully? And then just what are the most common pitfalls people fall into? So we could just maybe start with, what are other ways that companies do this well, build AI products successfully? I almost think of it as like a success triangle with three dimensions that's never always technical. Every technology problem is a people problem first. And with companies that we have worked with, it's these three dimensions, like great leaders, good culture and technical prowess. With leaders itself, we work with a lot of companies for their AI transformation, training, strategy and stuff like that. And I feel like a lot of companies, the leaders have built intuitions over 10 or 15 years and they're kind of highly regarded for those intuitions. But now with AI in the picture, those intuitions will have to be relearned and leaders have to be vulnerable to do that. I used to work with the CEO of now Rackspace, Gagan. So he would have this block every day in the morning, which would say catching up with AI 4:00 to 6:00 AM, and he would not have any meetings or anything like that. And that was just his time to pick up on the latest AI podcast or information and all of that. And he would have weekend vibe coding sessions and stuff like that. So I think leaders have to get back to being hands-on. And that's not because they have to be implementing these things, but more of rebuilding their intuitions because you must be comfortable with the fact that your intuitions might not be right and you probably are the dumbest person in the room and you want to learn from everyone. And that I've seen that being a very distinguishing factor of companies that build products which are successful because you're kind of bringing in that top-down approach. It's almost always impossible for it to be bottom-up. You can't have a bunch of engineers go and get buy-in from the leader if they just don't trust in the technology or if they have misaligned expectations about the technology. I've heard from so many folks who are building that our leaders just don't understand the extent to which AI can solve a particular problem or they just vibe code something and assume it's easy to take it to production and you really need to understand the range of what AI can solve today so that you can guide decisions within the company. The second one is the culture itself. And again, I work with enterprises where AI is not their main thing and they need to bring in AI into their processes just because a competitor is doing it. And just because it does make sense because there are use cases that are very ripe. Then along the way, I feel a lot of companies have this culture of FOMO and you will be replaced and those kind of things and people get really afraid. Subject matter experts are such a huge part of building AI products that work because you really need to consult them to understand how your AI is behaving or what the ideal behavior should be. But then I've spoken to a bunch of companies where the subject matter experts just don't want to talk to you because they think their job is being replaced. So I mean, again, this comes from the leader itself. I've spoken to a bunch of companies where the subject matter experts just don't want to talk to you because they think their job is being replaced. So I mean, again, this comes from the leader itself. You want to build a culture of empowerment, of augmenting AI into your own workflows so that you can 10X at what you're doing instead of saying that probably you'll be replaced if you don't adopt AI and stuff like that. So that kind of an empowering culture always helps. You want to make your entire organization be in it together and make AI work for you instead of trying to guard their own jobs, et cetera. And with AI, it's also true that it opens up a lot more opportunities than before. So you could have your employees doing a lot more things than before and 10x their productivity. And the third one is the technical part which we talk about. I think folks that are successful are incredibly obsessed about understanding their workflows very well and augmenting parts that could be ripe for AI versus the ones that might need human in the loop somewhere, et cetera. Whenever you're trying to automate some part of a workflow, it's never the case that you could use an AI agent and that will solve your problems. It's always, you probably have a machine learning model that's going to do some part of the job. You have deterministic code doing some part of the job. So you really need to be obsessed with understanding that workflow so you can choose the right tool for the problem instead of being obsessed with the technology itself. And another pattern I see is also folks really understand this idea of working with a non-deterministic API, which is your LLM. And what that means is they also understand the AI development lifecycle looks very different and they iterate pretty quickly, which is can I build something iterate quickly in a way that it doesn't ruin my customer experience at the same time gives me enough amount of data so that I can estimate behavior. So they build that flywheel very quickly. As of today, it's not about being the first company to have an agent among your competitors. It's about, have you built the right flywheels in place so that you can improve over time? When someone comes up to me and says, "We have this one click agent, it's going to be deployed in your system." And then in two or three days, it'll start showing you significant gains. I would almost be skeptical because it's just not possible. And that's not because the models aren't there, but because enterprise data and infrastructure is very messy and you need a bit to ... Even the agent needs a bit to understand how these systems work. There are very messy taxonomies everywhere. People tend to do things like get customer data, we want, get customer data, we do, and these kind of things. And all those functions exist and they're being called and basically there's a lot of tech debt that you need to deal with. So most of the times, if you're obsessed with the problem itself and you understand your workflows very well, you will know how to improve your agents over time instead of just slapping an agent and assuming that it'll work from day one.…
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