[00:00:00] Trisha Price: Hi everyone. I have an exclusive discount for Hard Calls listeners to Pendomonium, Pendo's Product Festival happening March 24th through 26th, 2026 in Raleigh, North Carolina. Listen in at the halfway point today to get this special discount to the product festival. Bringing today's top leaders in product, AI, and software.

[00:00:23] Trisha Price: Welcome back to Hard Calls. I'm Trisha Price. It's the first week of a New Year, and if you're like me, you are looking at everything, your roadmap, your team, your strategy, and you're realizing something. The hard calls you're facing are a lot bigger than deciding what feature to build. It might be determining if you have the right people with you on the journey, [00:00:45] which products you need to feed, which ones to starve, even if they're making money because maybe they don't serve the long-term future and strategy.

[00:00:52] Trisha Price: You are thinking about ensuring your team is truly optimized using AI and different tools, and you're thinking about that agentic AI feature you just shipped and whether it's performing and how its quality is. Over the last few months, I've had incredible conversations with product leaders from across the globe from companies like JPMorgan Payments, ADP, Morgan Stanley at Work, Vantaca, nCino, FactSet, and a couple of the best product coaches in the industry.

[00:01:23] Trisha Price: In this episode, we're bringing it all together. We're breaking down the hard calls and what's behind them, the people, [00:01:30] our investments, and the times where we bet everything. So whether you're navigating AI adoption, restructuring your team for scale, or just trying to figure out what to say no to this year, this is the perfect episode to get you ready for 2026.

[00:01:45] Trisha Price: Let's dive in.

[00:01:51] Trisha Price: Let's start with the calls that keep us up at night. The people, no spreadsheet can make these decisions for you. Sometimes it's about the culture. Sometimes it's about scale. Sometimes it's about performance, but it's always about protecting the company's potential. First up, Jodi McDermott three-time CPO and board advisor.

[00:02:12] Trisha Price: Jodi explains the most [00:02:15] dangerous person to have on your team, that high performer who destroys culture from the inside. 

[00:02:20] Jodi McDermott: I can think of a couple of hard calls particularly that have fallen into both of those categories with people. If you've ever had somebody in your organization that maybe was a really high performer, but they weren't a cultural fit.

[00:02:35] Jodi McDermott: Yes. And maybe they ruffled a lot of feathers and it wasn't one time, but it was continuous. There's been times I've had to make a really hard call to move a high performer out because I knew it was pulling down the rest of the team. Yeah. And, sometimes it's hard to even see it's happening. Because people are afraid to say something and, and you have to be watching out for that.

[00:02:56] Jodi McDermott: To be able to protect, you know, the totality of the team, right? [00:03:00] 

[00:03:00] Trisha Price: Protecting the team sometimes means making the decision to let someone go whom you genuinely like and respect. Jessica Soroky, a prod-ops leader, shared a hard call about a team member who was doing everything right. Well, culturally, but he wasn't the A player that the company needed to drive growth.

[00:03:19] Jessica Soroky: We had a team member who was absolutely trying their best. They were incredibly positive. They had like the, if I could recreate their personality and the professionalism and the willingness to try, I would do it a million times over. Unfortunately, even at their best for what we needed at the time we had to step back and be willing to look at is this truly [00:03:45] the best of the best? Is this the elite team member that we need right now to do everything we're trying to achieve? And the hard call, there was no, no, like great human being, amazing person. Worked really hard, tried really hard. But they just weren't what we needed to that A-player.

[00:04:03] Jessica Soroky: So, we had to make the really difficult call to have to part ways with that person to be able to create space for somebody who was better suited for our needs at the time. And while it's on a product specific call, I think it really did change because. I respect that human being, but the person they brought in has, has made some game changing moves for our team and for Pendo and all of that.

[00:04:25] Jessica Soroky: So at the end of the day, I know it was the right call, but it was definitely not easy in the [00:04:30] moment. 

[00:04:30] Trisha Price: One thing I learned from working with startups and large corporations is that the skillset to start a company is different than scaling one for growth. During the episode with my longtime mentor, Pierre Naudé at nCino, we discussed the brutal reality of scaling an organization and the hard conversations you must have with the people who helped you start the company when they can no longer contribute to its growth.

[00:04:54] Pierre Naudé: So I want you to think, I know you start thinking about product choices, technology tools. Do you embrace AI? You know, is it in the cloud? Is it platforms? The real issue is your organization with success will grow tremendously. And how do you scale both the structure? The people [00:05:15] management and the ability to manage hundreds of people versus in the beginning, you're a band of brothers or sisters.

[00:05:22] Pierre Naudé: You're all together, you're building this little company. You're so excited because you want your first ten customers. Well, the same people who ran that business on day one are not the same people who's gonna run it when it goes public. And I would tell you, if I come back to hard calls, some of the hardest calls is to tell those people that.

[00:05:40] Pierre Naudé: The scale has outgrowing their ability to manage and judgment, because what we get paid for in the end is judgment. Okay? And so then you have to find different positions in the company for them and bring people in that can do that scale. I think that is a critical element of management as well as product management.

[00:05:58] Trisha Price: The second type of [00:06:00] hard call we discussed on this show is what I refer to as the "stop" call. With the rapid advancement of AI capabilities and tools, there's a lot of pressure to move fast, but as leaders, we have to know when to hit pause in order to protect trust, to protect outcomes, and sometimes to protect our own teams from shipping something that isn't ready.

[00:06:23] Trisha Price: Peter Bailey from JPMorgan Payments face this head on. He had a launch ready for the Federal Reserve. High stakes, high visibility, but the data vendor just wasn't right. Here's why he risked his brand new job to stop the project. 

[00:06:38] Peter Bailey: There's always one that really jumps out to me. It was shortly after I joined JPMorgan.

[00:06:43] Peter Bailey: I was hired to be the [00:06:45] global head of product for our wholesale credit risk group. And, shortly before I joined, we had received some constructive, if not critical feedback from the Federal Reserve about our CCAR submissions, and we had received feedback specific to the way that we were providing information in our reporting.

[00:07:06] Peter Bailey: And, we're at risk of not being able to execute our plan. And so when I was hired, this was the problem I was given and to go and fix that. And what we realized, almost immediately was that a lot of the information that we were providing to the Fed had to do with our customers' financial data.

[00:07:26] Peter Bailey: It was the vast majority of the information that we were providing, [00:07:30] and we had a pretty broken way of collecting it and reporting it across all of our different lines of business, across our investment bank, commercial bank, private bank, business bank. All of these different teams were doing it differently, and ultimately by the time it got to the fed.

[00:07:45] Peter Bailey: We were not showing up well and the Fed knew that. And, it was raising concerns on our ability to manage risk and the information we were reporting. And one of the things we quickly realized was that, we have a lot of public clients, publicly traded entities, and a lot of this financial data is publicly available.

[00:08:04] Peter Bailey: So let's bring it into a new platform and we can structure it and ensure that we're delivering this information consistently. And as we were approaching that launch, one of the [00:08:15] things that really started to, to become apparent to me and was just not sitting well, is that the vendor we had chosen to provide the data really just was not the right fit.

[00:08:28] Peter Bailey: And no matter how hard we tried. It was becoming more and more apparent that we had made the wrong decision in terms of how we were bringing this data into our ecosystem. And so we had a decision to make. Do we launch and meet this target, and I think we still would've been able to show significant strides from where we were.

[00:08:54] Peter Bailey: Or do we look at it and say, we've this is not the right time, this is [00:09:00] not the right. Product and we need to take a little bit more time and go back to the, to the drawing board so you know, the decision. Do you launch something that, everybody's excited about, but you know, is not ready? Or do you hold the line and potentially risk disappointment?

[00:09:16] Peter Bailey: Put your job on the line even though it's the right thing to do. 

[00:09:20] Trisha Price: That theme of trust is critical, especially with incorporating AI into your systems and your products. ADP is responsible for paying one in six people in the United States, and when Naomi Le Riviere and her team are ready to ship a fully automated AI agent.

[00:09:38] Trisha Price: She stopped it. The product was ready. It was fast, it was innovated, it drove outcomes, but [00:09:45] clients weren't ready. 

[00:09:46] Naomi Lariviere: So, you know, I oversee our client facing AI program at ADP. It's called ADP Assist. And again, this is another initiative where it's build once, deploy it across our entire ecosystem. And we've been working on agentic AI and in the space of payroll and sometimes in the space of payroll. You know, and with this technology, we wanna go as fast as humanly possible. And there's so many wonderful things you can do with it, you know, from, you know, just task automation to like actually doing the entire process for you. And that's actually this initiative had that goal.

[00:10:26] Naomi Lariviere: We are just gonna do everything for you. You don't need to worry [00:10:30] and the hard call for us is as we started to talk to our clients and we were showing them early concepts of what we wanted to do, and you know, we were iterating on it. What we realized is that our innovation was colliding with the trust that our clients had in us.

[00:10:49] Naomi Lariviere: We service over 1.1 million clients. We pay one in six people in the United States. That's a lot of people. When you say you can't get things wrong. Imagine getting a paycheck that's not right, right? Like that is not a good scenario for us. It's not a good scenario for our clients. So you know, when you are doing things that may erode the trust of your user.

[00:11:14] Naomi Lariviere: You [00:11:15] might wanna reconsider what you're doing. So we actually, as we talked to the clients, we're like, okay, well if we wanted to get to that, they're like, well, that's a really great thing in the farer in the future. you know, like, how can we get you on that trust building journey? So, you know, what we learned is, yes, speed matters, but trust compounds.

[00:11:35] Trisha Price: Sometimes the stop call isn't about bad data or broken technology. It's about revenue and the cost of doing business. Board and product advisor. Jodi McDermott backs this up with her story of when she made a very unpopular decision to end a product built for a single customer. Was it making money? Maybe, but she explains why that money wasn't good revenue.

[00:11:58] Jodi McDermott: We had [00:12:00] acquired a company that had a product that they were building for one customer. So it was a product they had contracted to build this product and everybody felt like they were close to the finish line, close to the finish line. And every quarter that would go by, we just needed one more quarter.

[00:12:19] Jodi McDermott: One more quarter. And I had a few executives on, you know, my peers that were going, what are we doing over here? Why are we spending money on this? But, when you, when you, especially when you acquire a company, you have a new customer coming in. You, you're trying to be a promise keeper. Right, like product, you're trying to be promise keeper as much as you possibly can.

[00:12:39] Jodi McDermott: And that was one that was a really hard call that that, you know, we finally made the decision that we were [00:12:45] gonna go negotiate to get out of this agreement and that we had to say no and we had to stop because we didn't see profitability done online. At one point we did, and then it just kept dwindling and dwindling.

[00:12:55] Jodi McDermott: And especially when you are working in private equity and you have a timeline for how you're spending those R&D dollars. You just can't be deploying it where you're not gonna get the return. And that was a really, really hard call. And I would say that that was, that was probably one that I was, it was definitely influenced on, it was there, you know, it was discussion with my CEO and my CFO and, and others and how we were gonna manage the customer.

[00:13:20] Jodi McDermott: But that was a hard one. As a product officer of having to go and tell a customer, no, we can't keep going and we can't keep doing this. 

[00:13:27] Trisha Price: That I'm so glad you shared that because [00:13:30] sun setting products or disappointing a particular customer is probably one of the hardest. Things we do as CPOs. But I mean, you and I both know, even if you finished the product products are never finished, right?

[00:13:46] Trisha Price: Yeah. And so it's like even if you met the needs of that particular customer and got live there would've been asks for forever for that. And so you know, making that difficult decision not to do a one-off for a customer, but to try to invest those R&D dollars where you can get. A multiple where everybody's using it is obviously always the right choice, but that doesn't mean it's the easy choice.

[00:14:11] Jodi McDermott: Well, it comes down to what's good revenue, right? Yeah. So even if, [00:14:15] so, you know, somebody put on the table at that time, well, well, what if we keep building it and we just have a dedicated development team that does the work and we just carve it off and set it over here? Okay, well, but it's never, it's never gonna grow to be a 10 million, $20 million product, right?

[00:14:29] Jodi McDermott: You're never gonna get that enterprise value multiple off of it. It's this one thing over here, so. Is it good revenue? It's not good revenue. 

[00:14:38] Trisha Price: Mark Mitchell from Morgan Stanley at work explains the discipline of walking away from a massive client when the custom work required just doesn't balance out with the needs of the company.

[00:14:50] Mark Mitchell: I think, you know, I think there's a, so as I was thinking about this, there's a couple different answers to this, but I think. What I would say is one of the hardest things for our business and for my [00:15:00] role almost, you know, probably once a year, is we engage in a sales conversation with a really large client of ours.

[00:15:08] Mark Mitchell: And what we ultimately figure out after, you know, sort of getting into that sales conversation with this prospect is that we may not be a great fit for each other. You know, whether that's sort of on their side or on our side, or maybe a little bit of both. And it's this really tough decision that you have to like, sort of ultimately come to, to realize as excited as we are and as long as we've worked on this thing, there just may not be sort of a go forward path here for us.

[00:15:33] Mark Mitchell: And it's super difficult and always, always sort of, a hard kind of call to ultimately make. 

[00:15:41] Trisha Price: I'm so glad you talked about that, and I know that's gonna probably [00:15:45] weave through various conversations that we have today and man, that takes such discipline to be able to acknowledge that and I'm glad you brought that up, because all of us as product leaders, there's always pressure for revenue.

[00:15:58] Trisha Price: There's always pressure for customer happiness, and that's just such a hard and difficult decision to make. 

[00:16:05] Mark Mitchell: Yeah. When you look, you know, when you look at those situations and it's, you know, it's kind of, it's kind of the, you know, again, it's, it's more of an exaggerated version of what we sort of do every day, right?

[00:16:14] Mark Mitchell: It's, you look at the situation and you say the effort that we're going to have to sort of put out, right? Whether that's cost or, you know, development time or product, team time, whatever, however you wanna sort of think of it, is gonna be huge, [00:16:30] you know in this situation, let's just say. And then, you know, you sort of start to pencil out, okay, so how does that look over the longer term for revenue and for this and for that, and all the different dynamic parts of kind of like how these things fit together.

[00:16:43] Mark Mitchell: And you know, sadly, sometimes you just come to this conclusion that it just doesn't really, it doesn't really pencil, you know, and the the sort of upstream swim to sort of build the things that this particular client's gonna need. Find ways to sort of do that, that in a way that they add value to other customers and other clients.

[00:17:03] Mark Mitchell: Like, like that story just doesn't, it ultimately just doesn't tell, you know?

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[00:17:09] Trisha Price: Registrations for Pendomonium 2026 are now open. [00:17:15] We are bringing together the most inspiring minds in product and leadership who will challenge your thinking on everything from product-led growth to the future of product to gaining value from your AI investments.

[00:17:28] Trisha Price: It is likely you'll even run into some of our guests from hard calls. The product festival is designed to spark curiosity. Create conversation and build community while spotlighting the newest tech. For software experience leaders, I would like to invite you to join me in Raleigh, North Carolina from March 24th to 26th with an exclusive 30% discount.

[00:17:50] Trisha Price: When you use the code hardcalls30, that's hard calls all lowercase, and the numbers three zero. Get your discounted ticket at [00:18:00] pendo.io/Pendomonium. See you there.

PART 4: THE "GO" CALLS

[00:18:04] Trisha Price: Finally we have the "go" calls. The moments where you look at the market, your customer feedback, or even your own career, and realize you have to pivot even if it hurts.

[00:18:16] Noa Ginsberg: We try to bring more speed to decision making here, but yeah, you have to pull it forward. You have to make a hard call. You have to make it clear to people too, what the call is. And I think recognizing where you are, whether it's a people call or if it's a priorities call. I think knowing where you are is always important.

[00:18:34] Noa Ginsberg: In order to get where you wanna go, you have to know where you're starting, and that's something that we've, we think about a lot. We have a lot of good tooling in place. And you mentioned, you know, instinct [00:18:45] versus data. I really think our gut feel as you gain experience is a bunch of data that's just sort of in your own LLM, in your mind of what you should do what. You've seen this before, you start to have some pattern recognition. But always relying on gut checking that not only with the data, but with other experts, other stakeholders with our customers within our own teams. Always validating that. So like trust your gut, but verify I think is very important and using all those tools at your disposal.

[00:19:19] Noa Ginsberg: So you do make the best decision. 

[00:19:22] Ben Currin: To kind of maybe zoom out. Like what's a big, memorable hard call in the last, last year or so? I think [00:19:30] deciding on a direction of what it means to have an AI strategy was a really, and is a really hard call. It's also, I mean, it, it's hard. It's the most important and probably best thing that we've done over the last several years, but that's hard to say.

[00:19:47] Ben Currin: Hey, we've all been, and this isn't just Vantaca. We've all been spending all of our time and energy building software for humans for years and years and years. And then to think about what does it mean to enable humans to delegate all that work to AI and like what all is kind of a sunk cost of what you've built so far.

[00:20:06] Ben Currin: And is that okay and is it not okay. And do you wanna hold on tight to it? So, I mean. That that kind of big thing is, is probably the [00:20:15] hard call. And for us it was, you know, this is undeniably the future and it's, it is gonna be a great future and there's gonna be bumps along the way, but we have to jump all the way in the pool and not be afraid of, you know, how many sunk costs there are or what we have to go back and re-litigate In terms of things we've kind of held on tightly to before. 

[00:20:32] Trisha Price: But you don't always have resources or power when you know it's time to make a go call.

[00:20:37] Trisha Price: And that to me is one of the toughest positions to be in. Pendo's CEO Todd Olson shared a story from early in his career about creating a hill to stand on, building a product with no budget, no team, but knowing that customers would want it and it would be good for the company. 

[00:20:55] Todd Olson: I'm gonna go back to one pre Pendo, 'cause I think it was one of like the sort of like.[00:21:00] 

[00:21:00] Todd Olson: Interesting hard calls I made. I was, so this is at Rally Software just prior to Pendo, you know, this is maybe two to three years before I started Pendo. I was I saw this opportunity to build this add-on product and I was not the head of product there. I had no power, no control, no resources to do it.

[00:21:22] Todd Olson: I was in product marketing and but I had this opportunity and I saw this product . Actually some customer built some open source product using our APIs. And it was like, wow, all of our customers could use this. I mean, we talk about product market fit. When you have a customer build an add-on to your product that uses your data, you're like, okay, I know I want that.

[00:21:44] Todd Olson: So [00:21:45] I convinced a bunch of people to hire some consultants to take this open source product and start productizing it with customers over the next three to six months that outsource team grew and grew and grew into. It was like honestly kind of a full fledged engineering team. To the point where finally the CFO kind of woke up and is like, what's going on?

[00:22:09] Todd Olson: We have like, is this like some slush fund that you're like directing funds to? And that ended up becoming, a portfolio management add-on to our agile project management solution, which you know, the company ultimately sold to Computer Associates, which was in that space. But it was, I think it was that not letting title, not letting role...[00:22:30] 

[00:22:30] Todd Olson: I eventually took over product shortly thereafter. So then I actually had that ability to move the whole, like move a bunch of engineering resources onto it. We pulled it in house, but I think just not letting things get in your way. Yeah. I think that's how you make hard calls and like having conviction around something.

[00:22:49] Todd Olson: So, so yeah, I'd say that's it. 

[00:22:51] Trisha Price: Not all "go" calls discussed on the podcast were work related. Sometimes the "go" calls personal. Gabrielle Bufrem was a successful product VP at a high growth startup. She had it all, but she wasn't falling in love with the work anymore. Gabi walks us through the conversation she had with Marty Cagan that convinced her to bet on herself and go out on her own as a product coach.[00:23:15] 

[00:23:15] Gabrielle Bufrem: I vividly remember being having left my last startup. People were like, you're crazy. The market is not good. You have a great road at a great company. They're doing super well. And I was like, yeah, but I need something different. Like, I know that it's time. And I remember talking to many CEOs at that time, and they're all really great.

[00:23:35] Gabrielle Bufrem: Like a lot of them, I was like, whoa, this is like great business. I can see the returns. I would work for this person, all of that. But still, I like wasn't falling in love. And it was one conversation I had with Marty because any big decisions, I think, like I looked for my mentors and I told him, I was like, yeah, I'm just like not falling in love.

[00:23:56] Gabrielle Bufrem: He told me, yeah, because you wanna be a coach. Like you've told [00:24:00] me this. And like, I think I gave him 20 reasons, Trisha, why I wasn't gonna do it or why I wasn't ready. I was like, maybe it's this, maybe it's that, maybe it's this other thing. And I think he like crushed them all in like the bare like 10 minutes that he was just like, no, because of this.

[00:24:15] Gabrielle Bufrem: No, because of that. And then he was like, anything else? I was like, no. But I, I really do think it's taking the plunge from doing something that I knew I was good at, which was, running product and being a product leader to then stepping into a new role of helping other product leaders do their job really well and learning marketing and learning what sales is, and learning how to operate as a solopreneur and not have a [00:24:45] team around me anymore, and really taking that plunge and.

[00:24:48] Gabrielle Bufrem: I think that it, it felt like a hard call because it was the unknown, but it also felt really right, which I think is kind of the magic of product and making product decisions in general. It was like the art and the science. It's like I, I knew what had to be true for me to do it, and that was the science part, but I also knew, in my gut that it was the right instinct.

[00:25:13] Trisha Price: And speaking of Marty Cagan. We'll close this section with a very important lesson from the legendary product coach Marty Cagan. A "go" call isn't just about shipping, it's about absorption. Marty shared how he learned the hard way while at eBay [00:25:30] that just because you built it doesn't mean users can digest it.

[00:25:34] Marty Cagan: We had just acquired PayPal. And the hardest part for people on early eBay was just paying for something. They were literally sending checks through the mail. I mean, a lot of people were born after what I'm describing, so it was a long time ago, but it was you know, this idea of integrating a real payment solution.

[00:25:55] Marty Cagan: There was some crummy ones before, but this was good. Was something that we were really excited about and it was one of those rare eBay's, a marketplace. So there's buyers, sellers, and then eBay. It was one of the rare win win-wins. Buyers wanted it. Sellers wanted it. We wanted it. It was just a great win, and we tested the hell out [00:26:15] of it because this was a big change to the workflow to list something, a big change to buy something we did.

[00:26:21] Marty Cagan: We tested the hell out of it. We did all the practices that, you know, you try to advocate. Because of other mistakes earlier you learn that are really important to do. And we did it. And I remember, 'cause we got in this, right before we launched, we had a, we all sat down with the CEO and said, are we ready?

[00:26:38] Marty Cagan: And I'm like, we're ready. This is gonna be, this is, we're so excited. The community knows about it. They're excited about it. The people that tried it loved it. Anyway, we launched it. It was a disaster. And it was a disaster. It's one of those things, whenever you launch something big, you're kind of looking at the data because it's normal that there's a little bit of a dip [00:27:00] because it's basically people are learning how it now works and then that's normal, but you expect it to go up again and get better.

[00:27:08] Marty Cagan: And it wasn't. And I'm like, finally, oh my God. I know, I know what happened. We screwed up. I screwed up. And this was a lesson that I've got so many scars. I share this with so many companies even today, that it's not enough that people love your product. It's not enough. They also have to be able to digest it.

[00:27:32] Marty Cagan: And what was going on was, even though these buyers and sellers were screaming for this solution. That doesn't mean they were screaming to change how they work. 

[00:27:43] Trisha Price: The anatomy of a hard [00:27:45] call isn't just about it being tough or flipping a coin. To make the hard calls, you need the right data and tools to have clarity on a situation.

[00:27:54] Trisha Price: The right data helps you make. Better, more informed decisions by providing visibility into the situation. Whether it involves a team member, a product, or a strategic decision making the hard call is uncomfortable, but with the right insights in hand, you can make the calls that are best for you, your team, and your customers.

[00:28:14] Trisha Price: As we kick off this year, I wanna challenge you look for areas both professionally and personally, where you know a change is needed. Be brave. Make the decision and I know that I truly believe that no decision is also a [00:28:30] decision. I'm Trisha Price. Thanks for joining me here on the Hard Calls Podcast. And stay with us to keep hearing more from today's top product and AI leaders.

[00:28:40] Trisha Price: Thank you for listening to Hard Calls, the product podcasts, where we share best practices and all the things you need to succeed. If you enjoyed the show today, share with your friends and come back for more.