The Soothing Lull of an Organization on Autopilot

In nearly every product organization, particularly more mature product organizations, there are usually stretches of time where teams go into “autopilot” mode. Sometimes, this is because external conditions are so favorable that the numbers are all going in the right direction, and nobody is feeling all that much pressure. Sometimes, this is because people have stopped paying attention to the numbers, and the product team is operating with minimal accountability and oversight. And yes, sometimes, this is because all the right pieces are in place and you are operating like a well-oiled product machine.

But this autopilot mode comes with substantial risk. When a team has gone too long without a new challenge or a fresh perspective, it can begin to feel like “the way things are” is the only path to success. New ideas that don’t support the status quo are watered down or waved away. Teams become more insular and less curious, important questions go unasked, and critical opportunities are missed.

When your team feels like it is on autopilot, it becomes more important than ever for you to seek out challenging ideas and alternate explanations. Talk to users who have abandoned your product, even if there aren’t that many of them, and try to figure out what went wrong. Explore competing products, and catalog what they seem to do better than you. Bring challenging questions back to your team—what if the direction you’re taking is totally wrong? What if the linear growth you’re experiencing is a fraction of what’s possible? Model openness and curiosity by asking questions that directly challenge the work for which you are most directly responsible.

Finally, channel these challenging questions into hands-on collaborative work via time-boxed prototypes. What if we reinvented the product from scratch in one week? What if the core user need has changed, and we only had three days to transform our product accordingly? I personally favor prototypes that directly challenge the fundamental assumptions of a product over “hack day” and “20% time” projects that are framed as a break from working on the “real” product.

The Good Times Aren’t (Always) the Easy Times

So, if a lack of immediate challenges and the resultant autopilot mode is not the sign of truly good times in a product organization, what are the signs that a product management practice is improving organizational health? Here are a few general indicators that you are on the right track:

Conflicts are discussed in the open with minimal personal attacks

A healthy product organization is not marked by a lack of conflict; rather, it is marked by the ability to address and resolve conflict in the open with minimal defensiveness, ego-driven attacks, and passive-aggressive flailing. As we discussed in Chapter 5, disagreement can actually be a critical tool for making good decisions as a group.

Everybody feels invested in the work that they are doing

In a healthy product organization, everybody is invested in the work that their team is doing, and in the way that their team is working together. If you suggest a new product idea or a new process improvement and it’s met with a chorus of shrugs, this does not mean that you have the full and unwavering support of your product team. So long as disagreement is being handled in a healthy way, disinterest is actually much more dangerous for a product team.

People see new information (and new people!) as an opportunity, not a threat

In a healthy product organization, people never shy away from signals that they are on the wrong path. They do not wait until their quarterly review to share that they are unlikely to hit a quantitative goal. Their mission, per the CORE skills of product management, is to bridge their user’s reality with their organization’s goals—and any information, people, or ideas that help them get there are seen as a gift.

When I’ve interviewed for product roles in the past, one of the informal metrics I’ve relied upon most is, simply, how I’m treated when I walk into an office for the first time. Am I eyed with skepticism and hushed whispers? Or are people open, curious, and engaged? In a healthy product organization, new information and new people are seen as an opportunity to learn, not a threat to “the way things are.”

To summarize, the truly good times as a product manager are not necessarily the easy times. Nor are they necessarily times when the company itself is doing well, though that certainly helps. The times when product management is at its most successful and powerful are those when new challenges are actively sought out and approached with openness, curiosity, and candor.

It is not an accident that these times tend to coincide with major product launches, last-mile pushes to get a new feature out the door, and other high-stakes, high-pressure situations. The moments that require the most collaboration, the most camaraderie, and the most connection tend to be the moments when product management has an opportunity to truly shine. The real challenge is to bring that same level of energy and excitement to your work every single day.

Carrying the Weight of the World

Early on in my career, a mentor of mine told me that a product manager’s job is “to think about every single little thing that could possibly go wrong, before it goes wrong.” I replied, “Well, that’s pretty much what I do all the time anyhow, so this job should be perfect for me!”

For people who are inclined to carry the weight of the world on their shoulders, product management can be a little bit too perfect. Being a product manager can leave you feeling like every problem you encounter is yours to solve, from new products launched by competitors to personal disagreements among your colleagues. And during moments of particular organizational difficulty or dysfunction, product management can feel both relentlessly demanding and absolutely futile—like pushing a boulder up a hill while 10 larger, more important boulders roll down past you.

Many of my worst moments as a product manager have occurred during times like this, when the sheer weight of the job felt unmanageable. I have thrown tantrums in front of well-intentioned colleagues, stormed out of meetings with senior leaders, and withheld critical information from my own team out of fear that they would be mad at me. And the vast majority of this bad behavior has been motivated by the same dangerous fallacy: “I am the only thing keeping this team (or this company) from completely falling apart.”

This is where the connective nature of product management can serve as an amplifier of organizational discord. As a product manager, you are responsible for connecting people throughout the organization, and the more broken and misaligned these connections are without your direct and constant intervention, the more you can start to feel like you are the only thing standing between your team (or your company) and oblivion. During these times, you might begin to feel like you need to be everywhere at once in order to put out fires and resolve disputes. You might catch yourself grumbling to your friends, and sometimes even to your colleagues, about what a mess this whole thing is. But it’s your mess, and you can’t even imagine how it would continue to operate without you.

To revisit our bad product manager archetypes, this is where the thin line between the Hero Product Manager and the Product Martyr starts to blur. If you begin to feel like you are the only person who can save your team and your company, you are going down a dangerous path. Here are a few steps you can take to avoid falling on the double-edged sword of product heroism and martyrdom:

Make a list of the things outside of your control

Did a tech giant just launch a product that directly competes with yours? Are two senior leaders in your organization embroiled in a battle for the CEO position? While both of these developments might have a serious impact on your job, you can’t control another company’s roadmap or another person’s ambitions. Make a list of the things that are outside of your control, to serve as a reminder that it is not your job to solve every problem for everybody.

Look for opportunities to delegate important things

One way you can break the cycle of heroism and martyrdom is to delegate truly important things to your colleagues. Rather than trying to insulate your team from organizational dysfunction, ask your team to step up and take on responsibility for something that is actually mission-critical for the organization. Delegating important things to your colleagues means that they will likely run up against some of the same friction and frustration that you have been experiencing. While this is not an easy thing, it is often a good thing. It will give you a chance to address these challenges as a group, rather than you feeling like you are the only person capable of and responsible for solving them.

Protect the routines and rituals that bring your team together

During challenging times, it’s easy to let things fall through the cracks—especially things that don’t reflect the perceived urgency of the moment. Team lunches, coffee meetings, high-level brainstorming conversations—these are usually the first things to disappear from your calendar when the going gets tough. You might assume, as I often have, that your team will be just as happy to enjoy a delicious meal short one very stressed-out product manager. But your absence sends a powerful and dangerous message that the time you spend with your team is just not that important. Your colleagues might, in turn, wonder why they don’t have anything more important to do.

One of the very best things you can do as a product manager is to protect the time that your team spends together doing normal, fun, and routine stuff. Show up, be present, and model for your team that, even in the midst of major organizational challenges, it is of the utmost importance that you find time to step back, communicate, and connect.

Summary: It’s Hard Work, but It’s Worth It

From the thrill of a product launch to the frustrations of organizational dysfunction and inertia, product management tends to have some pretty extreme highs and lows. Product management necessitates being smack in the middle of whatever is going on with your team and your organization, which means that if there’s a lot of difficult stuff going on, there’s going to be a lot of difficult work to do.

It is for this very reason that product managers can have such a profound positive effect on the lives and experiences of their colleagues. Because you are in the middle, the actions you take are likely to be outsized in their impact. As the informal ambassador between your team and the rest of the organization, you can set the tone for how people communicate with one another, listen to one another, and demonstrate respect for one another’s time and perspective. And during times of organizational crisis, you can choose to be the fearless protector of the very best things about you team and your company.

Your Checklist:

• Be wary of your organization and team falling into autopilot. Actively bring new ideas and challenging perspectives to your team at all times.

• Use time-boxed prototypes to explore alternate product directions, even when there is no immediate or obvious pressure to change course.

• Remember that a good product organization is not one free of conflict, but rather one in which conflict is handled openly and without personal attacks.

• Try to bring the energy and enthusiasm from your best and most exciting moments as a product manager to every day of your work.

• If you begin to feel like you are the only person keeping your team or your organization from falling apart, take a step back. Make a list of the things you can’t control, delegate impactful work to your colleagues, and make sure you are protecting your team’s most valued routines and rituals.

• Understand that the connectedness of your role carries great responsibility, but also great opportunity. Do everything in your power to protect and embody the very best things about your team and your organization.