Product Leadership

Chapter 4. Is There a Formula for Success?

The primary concern for product leaders, and the people that hire them, is what makes a successful product leader. Closely related to this is how the leader builds a successful team around them. From the very first interviews with product leaders, we felt sure that a generic description of a successful leader would prove to be nothing more than a myth. No two product organizations, not even close competitors, are alike enough for a cookie-cutter approach to be possible. Certainly, no product leaders are that alike either.

It’s not surprising, then, that there is no single formula for success. Despite this, we were excited to find common threads running through the characteristics and styles of successful leaders. For the old pros, they will be reminders of what’s effective; for the newcomers, they’ll be a collection of best practices to amplify and accelerate personal growth. Here are some of the topics we’ll cover in this chapter:

• What works for other successful product leaders

• What styles of leadership exist and which are applicable to you

• What insights are generic or transferable across organizations

• What mistakes product professionals commonly make, and how they can be avoided

What Does Product Leadership Success Look Like?

Success as a product leader can be hard to define, but it is critical to do so correctly and to consider not only the leadership, but the product too. Ultimately, each product, company, and sector will be judged differently. Their successes and failures will be relevant only in the context in which they exist. However, one thing is certain: a product leader will be judged by how well they deliver a valuable solution to a customer problem.

This resonates with our own experiences and was reiterated by our interviewees. The bottom line is to focus on the problem. As GV’s Ken Norton says, “I like to start with the problem. Smart people are very solution-oriented, so smart people like to talk about what the solution is going to look like to the problem. But successful people think about the problem. Before I talk about this product, or this feature, or this device I’m going to build, I must understand the problem at a deep level. Then success is easy to articulate, because you know what it’s like when that problem is solved.”

Framing your success around solving or ameliorating a customer problem makes it much easier to define, share, and communicate that problem with your team. Suddenly, finding ways to get to that successful end state becomes much easier. The best product managers, therefore, focus on defining and prioritizing problems, not solutions.

Focusing on the problem instills a sense of what the goal is before it’s even articulated. The team focuses on the user’s need—what you’re trying to solve and why you need to solve it, not how. The research automatically skews toward a deeper understanding of the user, instead of simply testing possible solutions. The user stories and personas become rich background information, which helps everyone involved make connections and find solutions that might not otherwise be obvious. By avoiding optimizing for one possible solution, focusing on the problem and describing it well to the team can open up a much wider universe of solutions. Once the research has been done and defined, and the problems described and prioritized, the delivery team can collaboratively design the solution that gets the job done most effectively. That way everyone’s creativity can be directed toward a much better result.

Measuring Success

The best product leaders have a considered approach to defining and measuring success. Paul Adams, VP of Product at Intercom, says, “We spend a lot of time defining the problem and defining the success criteria. What’s the problem we’re going to solve and how will we know if we solved it?”

Measuring success will always be a hotly debated topic in the product leadership world, because we are all looking for an elusive metric that isn’t universal. There are so many debates about NPS (net promoter score), daily active users, licenses, LTV (lifetime value), and engagement by event. Our hope is that the development, product, and user experience roles are beginning to see the problem that has been distracting them from making clear decisions—outputs versus outcomes. Because we have been so focused on engineering delivery, our success metrics have been based on the output of simply shipping an experience to a customer. It’s time to go beyond the output and think deeply about measuring the outcome.

“Good product leaders think about success in the short term and the long term. If anything, they’re thinking more about the long term than many other people around the table,” Tanya Cordrey, previously Chief Digital Officer at the Guardian, underlines.

Here is a great example that hopefully we can all relate to. Imagine an enterprise dashboard that is intended to show return on investment to the buyer of an enterprise solution. In the planning phases, the requirements are set, and a beautiful interface is designed, coded in the web application, and shipped. Typically, the fact that something that the user hadn’t had exposure to has been shipped is success enough. This is not true anymore. The best product leaders in the world are placing a big data layer between the design and the server side, so they are able to measure every affordance choice in the experience. An example of an outcome in this scenario would sound more like this:

We would like to see a 65% increase in engagement of our enterprise dashboard experience within a 90-day period of production release. We would add in additional key performance indicators (KPIs) like average time in app, increased average # of logins. We also believe that these design bets (affordance choices within the experience) will drive that growth.

Normally, this would be established in the discovery phases and become the sole reason for creating a new innovative experience, refreshing an old experience, or removing technical debt. You can use other indicators such as NPS, which has proven to be a very scalable, teachable, and useful metric to use when applied correctly and not used as the only metric.

Cordrey adds, “I think return usage or any measure of customer satisfaction and loyalty are really important, because I think we’ve seen in the history of the internet that there are many companies with incredible topline figures, but at the end of the day those companies stall because they don’t have any retention and they can’t hold on to their users.”

Most metrics suffer from this—a single point of measurement. Try to begin with establishing an outcome, not an output, and that outcome should be based on your customer and the problem you are trying to solve. Then use several metrics in the experience to measure that outcome so that you don’t rely on a single metric organization-wide to drive your product strategy forward. The results will speak for themselves. Actionable, measurable, and time-bound metrics that balance the short term and the long term are the best practice by the world’s best practitioners.

Measuring Success as a Problem-Solving Ability

Recognizing product leadership through the use of measurable performance indicators is only the first part of the story. The second part is the organization’s ability to measure success. This, ultimately, is the ability to measure the problem statement, and that is as important as defining the problem itself. Many product leaders fall into the trap of measuring success with exclusively internal metrics, like how many cards were shipped. They assume that the announcement “We shipped!” releases tension from the team, because they assume success is measured when the item is delivered. This couldn’t be further from the truth. We agree that having an efficient delivery model that ensures work is shipped in a reasonable and healthy manner is a form of success, but, if the only motive is to ship an artifact, then it doesn’t solve the problem. Shipping work must also solve a problem and result in customers truly receiving value from whatever was shipped. It follows, then, that the ability to measure the outcome of this is paramount. It would be better to see teams obsess over indicators of success or failure as they relate to solving the identified problem statements.

Pluralsight, an online learning platform, provides a great example of this with how they discovered a problem statement around note taking:

Through observing Pluralsight’s learners [the company’s internal name for users], the team noticed two behaviors which proved to be important indicators of future improvements. While watching the Pluralsight courses, one learner was observed jotting down notes on a physical notebook, while another did the same using sticky notes. The learners wanted to save information they thought was important so they could return to those spots at a later date, and the handwritten note was a timestamp or a couple of words intended to jog their memory. These observations by the Pluralsight user testing team identified a problem that eventually became a permanent notes feature. The fascinating thing for the team was that the competitive landscape for this scenario was not another product, but a notebook and a sticky pad.

The team in this example rallied behind this problem statement. Once they released the feature into production, they began tracking a number of interactions with it versus other popular affordances to get quantitative feedback. The team was also acutely aware of the qualitative feedback that helped them make informed decisions on impact and next steps.

Success is a function of a team’s ability to unco..ver a problem, see how that experience would empower the user if it were gone, and deliver the solution in a delightful and efficient way.

Common Characteristics of Successful Product Teams

Every  team has a unique set of characteristics that bonds its members and aligns their efforts behind shared goals. However, it is possible to identify common themes in successful teams, and in our conversations with top product leaders, these came up again and again. Unsurprisingly, not one of our product leaders mentioned hard skills, such as engineering, design, or specific product management expertise. On the other hand, soft skills were referenced by almost everyone. In Drift cofounder and CEO Dave Cancel’s words, “It’s not that the [product leadership] skills are secondary; it’s that their past experience is secondary.” Cancel believes that the characteristics of a successful product leader will always be weighted toward the softer skills. “What we’re looking for are things that fit more on the qualitative side, which people hate because it’s so squishy.” These “squishy” things, when present, are what makes the people management element of the job infinitely easier, and they tend to be found in all great product leaders:

• Lifelong learning. Actively seeking new information, insights, and understanding is a cornerstone to successful product management. Things move fast in software, and standing still is consummate to sliding backward. Connected to this is an open-mindedness and coachability in all respected leaders; they don’t assume they know all the answers and constantly refactor their thinking to take in new knowledge and feedback.

• Strong communication. This is a big bucket that includes several soft skills like listening and presenting, but communication is fairly self-explanatory. As Bob Allard, CEO of ExtensionEngine, says, “All project management problems are communication problems.” This can be extended to product management too. Strong leadership of any kind has a foundation in strong communication skills.

• Empathy. Deeply connected to communication is empathy—not only empathy for team members inside and outside the organization, but for customers as well. “I think [product leadership] is significantly customer focused, and needs to be in order to build a great product,” says Joshua Porter, founder of Rocket Insights, a Boston-based product design and development agency. Nothing exists without the customer, so empathy for the customer experience is essential. Another element of empathy is being sensitive to the product creation environment you’re working within. This environmental empathy gives the product leaders insight into the kind of team to build and how that team can be aligned with the larger organizational goals.

• Diversity. Strong leaders know that a diversity of backgrounds, experiences, and demographics provides the range of perspectives needed to build a complete product experience. A one-dimensional team will produce a one-dimensional product, and the modern software product space is a complex array of tastes, needs, and expectations. Top product leaders look for team members that can bring differing opinions and experiences to the table.

• Business savvy. This characteristic is related to how product leaders understand their role in the value delivery process and their grasp of the broader business context. Solving problems for your market is the primary reason for the role, and a strong knowledge of where to focus effort and manage the assets to ship product is essential. It’s not necessary to have a full range of financial and operational skills, but a good product leader needs to be able to take a seat at the executive table.

• Cross-functional representation. Teams without representation see the world with strong biases. The more a product leader can bring the functional areas of a product together, the more likely the team will act in a coherent manner.

• Collocation. Working side by side with your team makes communication easier and faster. Placing the product manager next to the product marketer can have striking results on improving feature release communications. We really want to emphasize that the teams should sit right next to each other when possible. This improved communication substantially increases a company’s building velocity.

• Autonomy. The best teams have the ability to solve problems on their own without having to run everything up the ladder. Decision-making skills and the authority to implement those decisions are critical to a team’s speed and effectiveness.

• Interdependence. This might seem almost contradictory to the autonomous point, but successful teams don’t wall themselves off from the rest of the company. Autonomy is a reference to the ability to make decisions, not a reflection on their avoidance of others. Seeking out others in the company for input and knowledge reflects maturity in a product team.

• Accountability. The best teams place guardrails in place that allow them to see clearly when either the qualitative research isn’t paying back or the product releases are not hitting the desired outcomes. These guardrails must be supported by metrics and frequent measurements to be meaningful. Having these in place acts as insurance. Teams appreciate having this real-time feedback loop. As you can imagine, upper management also benefits from having this in place—especially in the early stages, as it establishes trust.

There are other characteristics that product leaders seek in their teams and organizations, but these consistently top the list. The more specific the product team roles, the more specific the skill set will be. For example, a product manager who is working on a product that leverages design aesthetics is likely to have a good sense of taste. Leaders will seek the team skill sets that match the context and stage  of their product.

How to Identify Product Leaders

If you’re a hiring manager, team lead, or a startup founder, you’ll need to know what constitutes a good product manager. Hiring for product leadership is hard, and the difficulty is exacerbated by the current high demand and low supply in most markets. The product leadership role will always include hiring and managing people, so unless you’re a single founder in a very small startup, you’ll be working with others, some inside and some outside the company. They might not be directly reporting to you, but you’ll be collaborating with them. Either way, working with people is part of the job. Although we’ve already mentioned some hiring strategies and tactics in earlier parts of this book, this section deals specifically with what to look for in a product leader. The characteristics listed earlier are high-level and provide some guidance for founders and hiring managers. This section digs a little deeper to describe what leaders should look for in high-performing product team members.

We’ve listed several areas that successful leaders point to when hiring a team or looking for product leadership in their organizations. Every organization will have qualities specific to that culture or situation, but the following qualities are relevant to almost every product manager and team. Some characteristics may be more relevant than others depending on the product, company culture, and stage of the business, but in general a good product leader:

• Plays well with others. Product management and product leadership are people-first roles. Teams are made up of individuals who each bring their own personalities, perspectives, and opinions. The best team members understand this and embrace the diversity, investing in getting to know one another. Understanding what makes people tick makes it easier to get the best out of them and identify when there is a problem. It has the added benefit of opening up communication channels. The personalities we exhibit at work are generally guarded and often belie our true nature, so taking the time to talk to one another provides the opportunity to communicate directly and honestly. Beware of the talented engineer who insists on working independently and claims to work better when left alone. Providing quiet spaces for people to work in can be productive, as long as team members don’t become isolated and shrink away from others, which can lead to misunderstandings and a breakdown in communication. Great product people see their work in the context of what the team is achieving. They are capable of connecting and communicating with lots of different personalities. This does not mean they are all things to all people, but rather that they are able to engage empathetically with others, even when they don’t have a lot in common with them.

• Seeks challenge. The product leader that enjoys new challenges will thrive in the current digital product environment. Between the ever-changing technology and product markets, there is never a dull moment in this space. Being comfortable with the ambiguity of this role is something we observed in most of the product leaders we interviewed. There are challenges around every corner, and a strong leader tends to anticipate change and prepare their teams for the constantly shifting sands of this space. Setting the expectation that nothing will remain the same reduces the stress that arises when that change inevitably happens. When hiring, ask questions about the person’s experiences dealing with challenging situations. Candidates should get excited and animated about how they solved problems or the prospect of meeting challenges head-on.

• Gets their hands dirty. Anyone who has worked on a product team knows that things are never perfect. The best team leaders don’t shy away from the daily messes; they get their hands dirty and solve problems. “I get feedback from the people I work with, that, as a vice president, I do a lot of practitioner-type work,” says True Ventures Design Partner Jeff Veen. “And I don’t mean sitting at Sketch or Photoshop with the pixels, but I run a daily stand-up with the teams going through what the decisions are for each day, asking, what is the product going to be? What did we find out from the usability testing?” Helping make tough daily decisions can be the best way for product leaders to help their teams. As Veen suggests, getting your hands dirty doesn’t mean doing the work of the technical members of the team. On the contrary, a poor manager or leader is constantly jumping in to do the practitioners’ work because they think they can get it done faster. Trusting others to get their work done is more effective, and delegating is the goal; this doesn’t mean being absent, it means involving yourself in the day-to-day workflow so you know what’s going on and can assist where necessary. Showing up as an experienced practitioner, but not feeling like you need to push the pixels or write the code, is a healthy balance for a leader. What this means is that leaders do need to remain close to the practice of the product creation process to ensure they maintain credibility with the team. Ultimately, unblocking obstacles from the flow of work is the best way for a product leader to get their hands dirty.

• Always acts and thinks “team first.” The kind of leader that needs constant recognition and praise is not likely to be the best person for this job. The top product leaders hardly ever get recognition for their hard work and dedication. Furthermore, they tend to turn any limelight they receive back on their teams. Putting teams first is what leaders do at all levels, and especially at the product level. Their efforts are consistently put through the lens of, “What can I do to make my team successful?” Knowing what will make the team successful, and acting on that, should be a part of a leader’s daily work. This team-first approach also relates to how leaders motivate and incentivize their teams. OKRs, goals, or rewards should all be aligned with what the team is working toward. This does not discount individual growth plans and OKRs, but they should be aligned with the greater good of the team or company. Culturally healthy companies will align individual and team goals with the company vision and values. Immature or unhealthy cultures align their team’s goals exclusively with things like financial bonuses for senior executives, share price, or the investors’ exit event.

• Is comfortable wearing lots of hats. All of the product leaders we interviewed have very diverse experiences and career paths. They are comfortable wearing the hats of marketer, manager, technologist, customer advocate, and facilitator, to name a few. We should add that this doesn’t mean they are experts at each of these roles; rather, they are comfortable working across all areas as the role evolves or as the product demands. On the downside, this can be a weakness if the product leader tries to fulfill too many roles for extended periods. Being competent doesn’t mean they have to take on everything. Understanding their own weaknesses, so they can delegate to more skilled team members, makes product leaders even better in the areas where they are strongest.

• Displays curiosity. This trait relates to several others mentioned here, but needs to be addressed specifically. Having a deep interest in learning, enthusiastically accepting new challenges, encouraging others to speak up, and listening to their perspectives are all actions driven by curiosity. Curiosity gives leaders the necessary mindset to solve problems. Product leaders are constantly reading and learning about what’s new and what will affect their product and teams. A leader that’s less curious is likely to miss potential solutions. Product leaders on the other end of this curiosity spectrum have little or no interest in other’s viewpoints, in listening to customers, or in learning new skills. This closed mindset tends to shut them down to new opportunities and solutions.

• Communicates well. This might seem so obvious it’s not worth mentioning, but it’s surprising how many senior managers and leaders are poor communicators. Having the ability to share information in a clear, concise manner is a necessary and desirable skill for a product leader. Whether they’re talking, listening, writing, planning, sharing, or facilitating, the goal is always to be understood. Key amongst these is written communication. Much of the product leader’s time is spent writing documentation, emails, reports, and messages to the team, outside partners, and other company leaders. If writing isn’t a strong skill, then getting training, or at the very least having a skilled assistant, is recommended. Visual communication in the form of sketching, drawing, and mapping is also an effective skill for all leaders in the modern era of whiteboarding and collaboration. Product leaders can be found at the whiteboard or sketchpad sharing their ideas on problem solving several times a day. Developing these skills helps tease the concepts out of the team’s minds and onto a space where those ideas can be shared and discussed. Even if stick figures are the pinnacle of their drawing abilities, it’s still an important part of the leader’s communication repertoire.

• Possesses selling skills. This might be controversial, but when you consider what product leaders do each day, it’s no surprise that selling is on this list. To be clear, this is not the type of selling associated with business development; rather, it’s the type that works to change minds and get buy-in from others. In his book To Sell Is Human (Riverhead), Daniel Pink refers to this skill as the ability to “move” people from one mindset to another. Product managers and their teams spend several hours each day engaged in these activities. They collaborate with each other to move ideas, and this requires being able to sell concepts and advocate for perspectives. Many leaders we spoke to don’t even realize they are selling, because getting buy-in on ideas feels like part of the job; however, they all recognize that these skills are critical to effective leadership. Linked to sales skills are negotiation skills. This is evident to any product manager who has had to present a project plan to an executive team. Life is one long negotiation. Every interaction is an exchange of sorts. Unfortunately, negotiation skills are not always natural or inherent. In fact, most people find negotiation difficult and even distasteful. Learning how to get what you need for your team to be successful means learning how to negotiate, and for any product manager, it might be worthwhile to get some training or coaching on this topic. At the very least, read the book Never Split the Difference: Negotiating As If Your Life Depended on It, by Chris Voss (HarperBusiness).

• Has exceptional time management skills. Shipping product is a race against time. Managing that race is a series of little decisions that collectively make up the product roadmap. Product managers that have risen to be leaders know this and protect their time and their team’s time. Time management stretches to almost every part of the job. Prioritizing the right work and delegating nonessential things is paramount to getting a product out the door. The interviews revealed that the top product leaders think of time as their most precious commodity. Tactics for efficient time management include reducing the frequency and duration of meetings, saying no to distractions, delegating wherever possible, and being fiercely protective of their time, all while making quality time for their team and customers. Time allocation will be very contextual and dependent on the personalities of the leader. We’re advocates for allocating time for uninterrupted, focused work, but we’re also aware of those rare examples where leaders are capable of achieving high outputs with shallower interactions. The book Deep Work: Rules for Focused Success in a Distracted World by Cal Newport (Hachette) explores these concepts in depth and is recommended for all product leaders.

• Is a visionary. Product leadership, by definition, requires a vision for where the product has to go. According to GV’s Ken Norton, “There are examples of great leaders who weren’t visionary but were great at making tactical decisions, which is perfect for taking a hill in a battlefield. That’s leadership. But product leadership requires a vision of where you need to be. What does this product need to be in five years? How are we going to get there? And how do I articulate that vision so that everyone else has it in their head, too? There’s the sense of a North Star that you’re aiming toward; that’s important to this type of leadership.” For great product leaders, this means “internalizing the vision, it means buying the vision, it means loving the vision,” adds author and consultant Rich Mironov. “And that means you end up being the visionary.”

• Shows equanimity/grace under fire. Being equanimous is tightly connected to the “plays well with others” trait we discussed earlier. Structuring equanimity into daily and weekly activities and meetings is the job of the product leader. “We practice equanimity—the idea of taking all this emotional anxiety and trying to structure it, understand it, and channel it into productive output,” says Jeff Veen. Google spent two years exploring what makes a team effective, including 200+ interviews and measuring 250+ attributes of 180+ active teams. Its conclusion? That the individual mix of traits and skills in the team was the least likely predictor of success. Who is on the team matters much less than how the team interacts, and the number one dynamic that defined successful teams was a sense of psychological safety—a sense that the team would not embarrass, reject, or punish someone for speaking up. Being able to instill this sense of psychological safety and trust is a key part of the product leader’s job.

While making a list of ideal skills is easier than finding the person that exhibits all of them, we maintain that a majority of these would be present in a good product leader. Our experience has taught us that even when some of these skills are absent or poorly developed in a leader, that leader is aware that these skills are important and worth developing.