Why decision-making comes down to customers and cross-functional collaboration: An interview with product expert Leslie Jordan

Why decision-making comes down to customers and cross-functional collaboration: An interview with product expert Leslie Jordan

Nov 20, 2023

Nov 20, 2023

In our last expert interview, we heard that one of the best ways to avoid bad product decisions is to involve key stakeholders across the business. In this article, we tap into the mind of Leslie Jordan, who has straddled customer-facing roles and engineering throughout her entire career––and she strongly advocates for customers as one of those key stakeholders.

The below discussion covers the never-overestimated importance of deeply knowing your customers, balancing multiple voices alongside quantitative and qualitative data, and the emerging need for better cross-functional collaboration. Spoiler alert: data-driven collaboration breeds better decision-making. 

Digital tools and capabilities have been credited with helping many organizations weather the COVID-19 disruption, but there’s also an analog source of innovation and adaptability in trying times: cross-functional collaboration.

––Deloitte, Teaming your way through disruption 

Making good decisions under pressure

To move with speed and accuracy (as the market demands), it is mission-critical to create a shared source of truth across teams centered on customers. As the CTO/CIO of Carmax  Shamim Mohammad puts it, “If you think about how fast technology is changing and how fast customer expectations are changing, to deliver what the customers are looking for, you have to organize as cross-functional teams. No single-function team can really deliver at the speed the customer is expecting.”

And all those digital tools and capabilities? They have to keep pace, too. Modern product-led software must perforate functional lines between Product, Marketing, Customer Success, and Sales. The Gartner article, Track Your Customer Health Score to Improve Retention, provides a great illustration of this principle in action: “To truly understand your customers and their satisfaction levels with your product or service, you need to go beyond standalone traditional customer experience (CX) metrics. For example, relying solely on feedback forms or one-on-one interaction with a customer success manager may not be enough to identify all the problems faced by a particular client or account. Plus, the timing of the feedback also matters; the survey responses may not come back in time for you to intervene for at-risk accounts.”

Crossing enemy lines? 

Let’s stay with Customer Success in an exploration of the benefits of cross-functional collaboration. Customer Success (CS) is an especially important ally for the product team (although these departments have a reputation for being ‘frenemies’ at times). ProductLed describes why there might be friction between these teams: “Many product-led companies don’t often leverage the wealth of information that client-facing teams have access to,” which is usually due to their differing job functions and lack of transparency.

The resulting misalignment can be harmful to the business and morale. Moreover, it represents a huge lost opportunity because, “There are healthy ways for Customer Success and Product to work together, achieving more than either team could on their own, according to the CS Insider article What I Learned About Working With Product in Customer Success. When Product and CS work as true collaborators, “The tight partnership creates a loop of continuous improvement,” says Slack, whose customer experience team is “strategically situated within the product organization.” 

The case is the same when it comes to collaborating with sales, marketing, support, and other teams. With greater context comes better and faster decision-making––and that could be the difference between ‘First to Market’ and the ‘Also Ran.’

For an expert perspective on data, decision-making, and communication, we turned to Leslie Jordan, the head of product engineering and design at Backflip. As a developer-turned-sales engineer, product manager at startups and tech mammoths like IBM, and the former CPO of Realtor.com, Leslie has built a wealth of knowledge in bringing people and data together to optimize planning, prioritization, and product strategy. 

Q: What’s your guiding philosophy for making product decisions? 

A: You need to understand the entire business, but first and foremost, you must understand your customers. Even with all the data, if you don't understand the main pain points, how your customers work day to day, and the overall motivations of your customers, you're not going to make good product decisions.

While I don’t agree with Product Managers who view themselves as the CEO of the product from a decision making perspective as if they have the ultimate authority (the actual CEO does!), what I like about the concept is that, like a CEO, Product Managers should feel accountability for the overall success of the product. Product management should feel accountability over everything that happens around the product. You should feel ownership and step in to help fill gaps when something goes wrong in Marketing or Sales or Customer Success.

Ask yourself how Product can help address the issue. And when you make decisions, you need to have spoken with both customers and stakeholders in every division that has something to do with the product, so you’re intimately familiar with your customers’ workflows and how the product and any company interactions/services integrate with those workflows. Each department will have a unique perspective; the customers have a unique perspective. You have to balance all of those perspectives, in addition to your product data, and ultimately make the best decision that will best solve the customer problem and provide them the most value while driving the highest impact for the business. These decisions become easier and quicker the more context and familiarity you have with your customers and customer-facing people and processes.

Q: How do you think about balancing qualitative feedback, quantitative data, and intuition? 

A: Some of it starts with the direction set by the CEO about what we're trying to achieve as a business and the overall mission for serving your end customer. Then you have to work with the CEO on where you want to focus. You use quantitative and qualitative data to inform your perspective and those decisions, but the CEO ultimately decides where resources go.

Ideally, you use data to inform and guide these conversations. You want to align the data with customer priorities and with the company direction, and then balance that with what is going to have the biggest impact on solving a customer need and driving revenue. 

Again, the bottom line is deeply understanding your customer and their problems. If you empathize with your customer and understand their journey and motivations, your intuition gets much better in making some of those big bets.

Q: Tell us about the framework you’ve developed for making product decisions. 

There are two levels of prioritization conversations you need to consider in making decisions. There’s the overarching priorities set by the CEO around what you focus on broadly, and then there's the plan of how you’re going to execute against those priorities. When you focus primarily on customer problems, you don’t get as bogged down with individual features, but you’re looking at what core problems of this overall customer workflow or customer journey you are going to address. 

When you’re coming up with the broader priorities with the CEO, you look at market opportunity, the problem space, the right to win, mission alignment, and offering complexity. For example, let’s say the total addressable market for a solution is huge. But it might not actually be a big problem for your end customer. Maybe it’s solved well enough, and you're in a mature market where it’s hard to compete because people are happy enough and it's not a big enough frustration in their journey. Assuming there are bigger problems to solve, despite the large TAM, the problem is most likely not worth prioritizing.

Then you have to ask if this is a space your customers could trust you to go into as a brand. Is it a natural fit? And does it align with your company mission? There are companies that will do unnatural things to make money. I really like Backflip because we have a strong mission and we want to stay aligned to that mission to help our small entrepreneurs and individuals flip homes. 

Finally, you need to consider complexity at a business level and an engineering level. How efficiently can you deliver on this, and is the lift worth the time and effort? 

Q: What do you think is the ideal working agreement between Product and Customer Success, as well as any other customer-facing stakeholders?

A: Communication goes both ways. It's not possible for a product team to build everything everybody wants. So it takes communication to set the sales and customer success team’s expectations and explain what we're prioritizing and why. As a product person, it's like you're essentially 'selling' to your own sales team. You have to sell them the vision and be compelling enough for them to buy into why you're prioritizing which things. This can only be successfully achieved when they consider you an expert on your customer.

A way to stay on top of what the teams are seeing more broadly is to meet with them regularly. I usually meet with these stakeholders at least bi-weekly, and I want to hear the three top issues they’re seeing right now. If they continue to come back with the same issues and it's impacting sales or retention, that's when you start really thinking about reprioritizing. They can be your ear to the ground making sure you're understanding what's blocking and causing customer churn from their qualitative perspective. They will tend to bring up issues from the most recent conversation they had, which a lot of times is not a pattern or a consistent issue across many customers. If it’s not an issue you can identify in your systems, get them to define the broader impact of the issue and bring more data about the issue across more customers. 

Q: Even when you do everything “right,” a decision might be the wrong choice. How do you minimize and recover from that? 

A: We're never perfect in our decision making. To minimize the impact of wrong decisions you need to ship early and often. You have to just get something out and not spend too much time before you get it tested and get people using it so you can actually get real market data. Then just be very ruthless in making those calls and not letting human emotion get into it. It may be that this whole team worked on it for six months and you’re worried it's going to destroy their morale, but as a leader, you need to set expectations that it’s going to happen sometimes. And it’s okay. It doesn’t mean the team did anything wrong; it just happens in business. You try something; you get it out; you can't find product-market fit; you move on. You just have to pivot quickly.

Sometimes it takes failure to learn what you need to learn in order to actually get much farther. There's a book called The Obstacle Is the Way. And I love that mentality in life: It's the hard things that you have to do to get that achievement. And sometimes that is failing, but getting through that failure and learning from it is when you build a better business and become a better professional and better person.