Why the Worst Product Managers Expect the Best

With each product I’ve built, things rarely come together exactly as planned. But it’s not the inconveniences, technical challenges, or misguided people that are the problem. It’s that we ever allow them to catch us off guard in the first place.

Anyone can operate under ideal conditions. But ideal conditions are the exception, not the rule. Eighty percent of your time building product will take place in a maelstrom of ambiguity and obstacles.

It’s naive to expect that the world should bend to your favor and promote ideal conditions. Most reasonable people acknowledge this. But when it comes down to it, many of us cling to expectations that our work should progress without pushback and our lives should follow a neatly charted map. We forget how much of life is negotiating egos and hidden variables along the way. 

The best teams embrace imperfections beyond their control and create great products anyway.

The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

It’s easy to pick out the product teams who struggle with this. Each challenge appears to catch them off guard, demoralizing the team and throwing people into a state of anger or despair. This type of reaction points to two things: inexperience and fragility.

Improvement comes from experience and perspective–you’re prepared to face a wider range of potential scenarios. In turn, this allows you to develop a deeper well of resilience and resourcefulness.

Creativity and resilience

At age 23, I started working for a healthcare startup, building out a web-based patient portal. Each setback caught me off guard because I expected things to just work–a laughable statement for anyone who has worked in technology for more than a week. When I went on-site for the launch with our first big client, I was unable to anticipate the ways I was about to get torched. 

There were technical challenges inherent to a complex healthcare organization and integrations with its existing software that we had to sort through. But the technical challenges were only half of it. The true test was handling stakeholders–internal and external–as well as the people who create noise and thrive on passive-aggressive emails.

Anyone who has worked in product is familiar with these challenges. There’s nothing unique about them. But I struggled to adapt because my expectations were off base. I lacked perspective. I was focused on perfection in our product and people pleasing–both impossible tasks–rather than creativity and resilience. 

The best product managers are able to cycle through dozens of permutations and anticipate certain situations through dimensional thinking. But no matter how good you are, at some point you’ll get hit by something you didn’t see coming. Whether the feature you’ve been working on breaks or a “senior leader” steps in and changes the rules at the last minute, you will encounter situations that test your limits. 

Your job isn’t to prevent these mistakes or eliminate every obstacle. Rather it’s to develop the ability to continue moving forward when the inevitable occurs. Leading product requires that you establish an unwavering sense of perspective and imbue this quality in your team. Then, and only then, can you build the resilience and resourcefulness to adapt, imagine creative solutions, and bring them to life. 

Resilient teams who cause a few more quality issues will always beat out fragile teams who are only able to operate under perfect conditions. The difference is self-awareness and being able to step back to put things in perspective. This means assuming responsibility instead of feeling sorry for yourself because something you built didn’t work or someone criticized you. 

This is not to say that you shouldn’t focus on promoting favorable conditions. You can’t create a complete shit storm for yourself and hope to come out better for it. But you should also understand that you’re never going to get ideal conditions. There are going to be things beyond your control. And that’s what keeps life interesting–the challenges and obstacles you have to learn how to overcome along the way.

Each team meeting, one-on-one, and retrospective is an opportunity to develop these qualities in your team. By challenging each other to maintain perspective and reflect on experiences, you can turn things back to what’s within your control–your attitude, the effort you put into your work, and the guiding principle that propels you forward.

Opportunities for reflection

In my experience, few things are more valuable to the morale and resilience of a team than holding retrospectives every few weeks. These are best done with your immediate team (keep things small so everyone can have their voice heard) in a low-stress environment, outside of work. There are multiple formats, but each person should have a chance to discuss what’s gone well and what hasn’t. 

This provides a valuable outlet for everyone to air their frustrations, without judgment or repercussions, and remind each other of recent accomplishments. It also allows the team to come together and consider how you might frame challenges in a more productive light and course correct the things within your control.

Retrospectives are just one outlet to discuss experiences and rediscover perspective. And with the right perspective, you can begin building the resilience to navigate the conflict and uncertainty inherent to challenging work. 

Creating more opportunities for reflection is the best way to harness experience and build perspective. It’s the first step towards realizing that imperfect conditions are where the majority of life takes place. Knowing this, you’ll be able to lead better teams, build better products, and live a better life. 

Expect challenges. Expect unknowns. Expect ego. When you set your expectations accordingly, you’ll waste less time consumed by the things that have happened to you. 

Anyone can operate under ideal conditions. But the best product teams don’t sit around waiting for the stars to align. Instead, they embrace the imperfections inherent to life, create their own momentum, and make things happen for them. To steal a line from Charles Bukowski, “What matters most is how well you walk through the fire.”

*This article was originally featured on Mind the Product.

The Secret to Developing Thick Skin

If there’s a defining feature that sets apart smart creatives who are able to sustain themselves at a high level of performance, it’s thick skin. They’re persistent in their work and resilient to outside opinion and rejection. They’re able to put themselves out there, time and time again, and deliver. And while this might appear to be a natural talent, it’s far from it. It’s a skill that takes years to develop, and it begins with renegotiating expectations.

Many talented people struggle with this–entrepreneurs, artists, athletes, writers. While they might be brilliant in their work, when it comes to putting themselves out there, they end up demoralized or enraged by the slightest hint of criticism.

This becomes a downward spiral that throws off the entire creative process. Even if you are able to correct course, it’s an unnecessary distraction that disrupts your focus and pulls you away from more meaningful work.

Internal vs. External Expectations

To offset this and develop the thick skin required to put yourself out there, you must first differentiate between internal and external expectations, assigning each their proper weight. Internal expectations–the expectations you hold for yourself and your creative process–should always take precedence.

How your work is interpreted, received, or recognized, is beyond your immediate influence. It’s not that this is completely irrelevant, but it should matter far less because it’s an unreliable metric against which to measure yourself. The greater the importance you assign to external expectations, the more dependencies you introduce, and the higher the likelihood that you’ll end up pissed off, burned out, or distracted from the work that matters most.

Self-sufficiency is the path towards effectively managing expectations. In the opposite direction are dependencies–evidence of placing a premium on things you can’t affect.

When you prioritize the internal expectations you hold for yourself, you naturally develop the thick skin required to put yourself out there and consistently produce at a high level. Instead of seeking value in the recognition, you begin seeking value in the creative process itself. And this is the only sustainable path forward.

“The tranquility that comes when you stop caring what they say. Or think, or do. Only what you do.”

— Marcus Aurelius

Turn your attention back to what’s within your control. Put in the work. Focus on your craft. Create something that resonates with you. When you limit the external dependencies and surrounding noise, the more relaxed, concentrated, and effective you will be.

Feedback vs. Criticism

This is not to say that you shouldn’t seek feedback–which is critical to further developing and growing your skills. But feedback is to criticism as internal expectations are to external expectations.

In other words, the source is fundamentally different. Feedback comes from fellow creatives with skin in the game–the doers–who are taking risks by putting themselves and their work out there. These are the people whose opinions and judgment you should respect most. Criticism comes from insecure bystanders, shouting from a distance, who are incapable of creating anything meaningful of their own.

The intention behind feedback is also different. Criticism is often shallow and malicious in nature–focused on breaking you down. True feedback, from an inner circle whom you respect, is diligent, constructive, and objective. Its purpose is to challenge you to improve yourself and your craft.

In short, it’s about growth–which is a painstaking process in its own right–not about praise, telling you what you want to hear, or making things easier. It’s up to you to draw the line and determine who has your best interest in mind.

Create Your Own Momentum

When the inevitable criticism does come, use it as motivation and redirect that energy to create momentum of your own. With the right perspective, it becomes almost laughable.

Consider how much time and energy it took that person to criticize you–it consumed them. Nothing is a more sad, ineffective use of time–so let the childish tantrums end there. Refuse to allow yourself to be distracted by those without skin in the game. Their opinion holds no validity.

“An opportunist in life sees all hindrances as instruments for power. The reason is simple: negative energy that comes at you in some form is energy that can be turned around–to defeat an opponent and lift you up.”

— Robert Greene

For most talented, hardworking people, it’s just a matter of time. Which means you need to find the energy to keep going–to continue creating. The more dialed into yourself that you are, the less outside opinion should matter, and the more resilient you’ll be in your creative process. If you rely on external validation to keep you going, you’re going to have a short career.

A meaningful, fulfilling creative life demands hard work and tough decisions. Those who aren’t cut out for it will lean towards the path of least resistance, as defined by mindless consumption or shallow criticism. It’s easy to live that life.

If easy is what you want out of life, feel free to join the ranks of the unremarkable.

But those who make a difference show up, bust their ass, and sustain themselves at that level by having their expectations in order. They’re able to differentiate between internal and external expectations, valuing self-sufficiency over dependencies and feedback over criticism.

If you take the time to develop these skills–resilience, persistence, and mental toughness–outside opinion will lose its grip and you’ll be able to better carry your own momentum forward.

The Myth of Losing Your Edge

One of the biggest fears that many hardworking, talented people have is that if they ease up in any facet of their lives, they’ll lose their edge. It’s a myth that’s fueled by a failure to differentiate between internal and external expectations. If you want to be at your best, it’s important to make this distinction and assign each their proper weight.

If you’ve convinced yourself that your edge comes from orchestrating external factors–things that are by nature beyond your control–that’s your ego taking over. This mindset is what pushes people to high strung, compulsive, and rigid behavior. Attempting to inflict your will with brute force and control every variable will drive you to exhaustion.

What keeps you ahead is not a state of constant dissatisfaction and the excessive demands you place upon the world. And while you might be quick to dismiss this as the ‘slackers credo’ of aiming low, take a closer look. Renegotiating expectations has nothing to do with the trajectory of your aim. It’s about prioritization.

You do not control the actions of others, how your work is interpreted, the recognition you receive, the specific obstacles you face, or whether the perfect sequence of events unfolds immediately before you.

It’s not that these things don’t matter. But they should matter less. Because they aren’t what define your edge and they aren’t reliable metrics against which to measure yourself.

The greater importance you assign to these types of external expectations, the more dependencies you introduce, and the higher the likelihood that you’ll end up pissed off, burned out, and distracted from the work that matters most. While you might be able to influence these to an extent, any significant control you believe you possess over them is illusory.

Your real edge is in your persistence and your own abilities. Your inner drive is independent of external expectations–the two are not inextricably linked. You have to be able to separate these from one another, as the resourceful and antifragile know well.

Rather than compromising your edge, redefining internal and external expectations puts you at a significant advantage. You free yourself to focus back on the things you can actually affect–mainly, your actions, dedicating time to your craft, discovering meaning in your work, living in accordance with your principles, developing your own resourcefulness, navigating inevitable obstacles. This is the most accurate way to measure your own progress.

When you become reliant on someone or something else to determine a successful outcome or your personal sense of self-worth, you’re putting yourself in an impossible position. Dependencies introduce anxiety and envy.

The mentality of “if only X, Y, Z happened for me, that would solve everything” is more of a liability than it is an asset. And it doesn’t say much for your ability to prioritize. Why place a premium on things you can’t directly affect? You’re wasting your limited time and energy, which could be better allocated elsewhere.

What you should prioritize is a state of relaxed concentration. It’s here where your best work gets done.

When you turn your attention back to your own abilities and immerse yourself in the task at hand, the anxiety subsides. There’s something calming about putting in the work when it’s down to just you and your craft. It brings things back to self-discipline, self-expression, and the pursuit of meaning in your work, all of which are within your immediate grasp.

Most top performers, who once believed their insatiable, demanding tendencies to be their edge, will concede this with age. What you achieve in life is not conditional on your external expectations. They don’t make you better and they don’t guarantee success. There will always be other factors in play beyond your control, and that’s okay. What actually matters is your internal focus, the work you’re putting in, and the expectations you hold for yourself.

Renegotiating expectations doesn’t mean sacrificing personal aspirations or expecting less from yourself. And it doesn’t mean aiming low. It means aiming higher and demanding more–of yourself–and prioritizing that. Define yourself by substance. Not by luck or futile attempts to bend the world to your will.

When you differentiate between internal and external expectations–assigning each their proper weight–it’s not your edge that you’ll lose, it’s your angst. In its place, you’ll build gratitude and a greater capacity to focus on the work that resonates strongest with you. It’s here where you can make a real difference and develop the quiet confidence that it takes to create something meaningful.

The Stoic Guide to Winning the War of Reality vs. Expectations

“Fortune falls heavily on those for whom she’s unexpected. The one always on the lookout easily endures.”

— Seneca

Most of us are torn between the duality of what’s playing out in our minds and what’s actually taking place around us.

We all have certain expectations that things should go a specific way. For some of us, it’s holding fixed expectations that our relationships should be exactly as we’ve imagined—perfect partner, kids, family, friends. For others, it’s the expectation that we should have it all figured out by now, that our careers should follow a carefully plotted path, or that some special event—wedding, birthday, vacation abroad—should live up to the hype.

The trouble with this line of thinking is that higher expectations do not equate to higher levels of happiness, gratitude, or performance. Additionally, projecting fixed expectations is in fundamental opposition to the impermanence and ambiguity that define life. Expecting things to go a set way is to reject the fabric of life. You cannot and will not eliminate all uncertainty from your life, no matter how hard you try.

In reality, there’s no such thing as the way it should be. Everything is in a state of constant motion.

The harder you work to eliminate uncertainty and ambiguity from life, the smaller the confines of your comfort zone become. True comfort is found through embracing discomfort, not shielding yourself from uncertainty—and this is the paradox of comfort. The wider the range of potential scenarios that you’ve trained yourself to handle, the better things will turn out.

It’s not that expectations are inherently dangerous. But they become exactly that as we fixate on a single outcome that’s outside of what the Stoics deemed as our ‘reasoned choice’—one which we have little to no control over. Positive visualization—setting expectations sky high and fixating on the best-case scenario–is not so much a strategy, as it is a recipe for failure. Sooner or later you’ll end up wrecked by something beyond your control.

Expectations outside of your reasoned choice leave you fragile, rigid, and reactive. Focusing your limited energy on trying to control every variable and getting from A to B like you’ve dreamed it in your head is restrictive and ineffective. It limits what you will learn, what you can achieve, and the person you will be.

“Who then is invincible? The one who cannot be upset by anything outside their reasoned choice.”

— Epictetus

Negative visualization—contemplating the range of potential outcomes, including the unfavorable and worst-case—is a far more effective technique offered by the Stoics (also known as premeditatio malorum). The greatest minds don’t sit around thinking of a fanciful alternate reality where everything plays out according to plan. They develop the resourcefulness to navigate inevitable obstacles and turn them to their advantage.

The only expectation worth holding is that you take advantage of opportunities to act in accordance with your own values and principles. You should expect to leverage your own resourcefulness and resilience to better yourself, regardless of current circumstances or obstacles. Create your own momentum.

“Just as nature takes every obstacle, every impediment, and works around it – turns it to its purposes, incorporates it into itself – so, too, a rational being can turn each setback into raw material and use it to achieve its goal.”

— Marcus Aurelius

It all comes down to your perspective. Prepare yourself to handle a range of potential outcomes, develop confidence in that ability, and limit any expectations beyond your reasoned choice. When you adopt this mindset, you strip setbacks and external circumstances of their power to catch you off guard and dictate your life.

Reality rewards resilience. Projecting fixed expectations in life blinds you to everything but the one-track, imaginary path you’ve predicted.

At the foundation of each of these Stoic lessons is the negotiation of reality and expectations.

Acknowledging this inner war allows you to bridge the gap and begin developing the mindfulness, focus, and resilience that it takes to make meaningful progress of your own. Otherwise, you run the risk of becoming disconnected and discontent with the only life you have.