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Product Management

Experiencing & Responding to Failure as a Product Manager

Justin Mertes
May 8, 2019

The Truth

Let’s just get this out of the way: if you’re a Product Manager, you’re going to fail… and it will hurt. Your failures will frustrate your clients, your own product team, and yourself.

The good news is, failure makes us better, gives us the opportunity to show our character to our clients and team, and gives us empathy for the failures of others. It also, to quote Calvin’s Father, “builds character.”


cartoon thomas and hobbes
“You mean this wasn’t the feature set you wanted us to build out?  Well at least we built some character!”


Before we jump to the “optimistic conclusion,” though, let’s zoom out: what am I talking about when I say “failure?”

What is Failure?

For the purpose of this article, my working definition of failure is “any wrongdoing done or rightdoing” left undone that hinders or sets your team back in any way.” This is a broad definition, but the heart of it is that failure is something that made you hang your head in frustration at yourself. It can be something that you recognize immediately, something that gets brought up in a one-on-one, or something that you thought was fine until you received an email from a sincerely disappointed client. I may not be able to define it perfectly, but I think you know the gut feeling when you realized that something just hit the fan, and it’s your fault.

The working definition I use specifically makes a dichotomy between things “done” and things “left undone.” This is important because we need to realize that it’s not just when we said the wrong thing in a meeting and hurt our client’s feelings that we failed. It’s also when we could’ve called two days before a mishap to cover our bases about some unspoken assumptions, and that lead to a screw-up.

NOTE: To get semantical, one could easily (and fairly) make a distinction between the word “mistake” and “failure,” in that mistakes lead to failure. For the sake of simplicity, though, let’s lump “mistake” into my definition of failure.

Who am I to Write About This?

I’m a Product Manager, and I’ve failed many times, and I’ll fail many more. I’ve made snap judgements that have frustrated clients, and I’ve said things that have hurt others. I’ve made costly mistakes that I should’ve been fired for, and I’ve had impromptu one-on-one’s where my boss has said, “Let’s talk about this thing that you did.” So, yeah, I’ve failed.

I also work at Crema, and every conversation I’ve had about my failures at Crema have been grace-filled, full of listening and encouragement, and reshaped as opportunities to learn. I’ve been encouraged to keep working, keep learning, and keep growing. The ethos at Crema whispers “you’ll fail, but in failure you’ll grow and be better.”

Crema embodies the following quote from management demi-god Peter Drucker: Every knowledge organization is a learning and teaching institution. Knowledge can’t be taught, but it can be learned.

So not only do I fail, but through Crema, my understanding about the role of failure as a PM is continuing to develop into something more than the reactionary “hang my head in shame.”

I Failed… Now What?

Right, so you blew it. For one reason or another, in one way or the next, the shit’s hit the fan, and now multiple people (or teams) are suffering the consequences.

fan in office building
Things are going to smell bad for a while (from the movie Airplane!)

You’re the Product Manager, and it’s your responsibility to help set realistic expectations, align the team, address unspoken assumptions, and build what the client wants you to build. Now, thanks to you, that’s not happening. As such, the first step to take is…

1. Tell Someone (Immediately)

If you’re a PM, you’re not an island. You have a product team, a product owner, a fellow PM, a boss, etc.  If possible, find someone that’s “up the ladder” from you. They’re a more senior team member for a reason – they’ve been there before, they have expertise in this area, and sometimes it’s their ass that’s on the line if you mess things up really bad.

Find one of them and ask if you can have five minutes of their time because “I think I just messed up, and I need to talk it over with someone.”

This is a crucial first step because it gets you speaking & processing out loud what happened, why it happened, and the way you’re seeing the problem.

This helps you more fully understand the narrative you’ve been telling yourself and figure out what precisely went wrong. It helps you understand where your mistake took place, and why it took place. It exposes you to multiple options of next steps. It brings someone else into the conversation who very well could save you from not making another mistake.

2. Do Whatever Needs to be Done

Telling someone is important because you’re not just doing what you think is the best next step. There are several different types of responses, so I’ll break down four of them right now:

Response: “Yeah, this is bad. Let’s go talk to X about it.”

I hate to break it to you, but your failure is now climbing up the ladder. We’ve all been there. The good news about this is that you get to be the one to tell whoever it is that needs to hear it. They get to hear the full context, they get to hear why you made a decision or didn’t make a decision, and they hear it in your voice that you are mad at yourself, or disappointed in yourself, or whatever your emotion is.

Now’s the time to tell the whole truth. Don’t sugarcoat it--they’re going to find it out anyway. Listen to their wisdom, and do whatever the next step is.

NOTE: You know what’s great, though? [If you’re working at a healthy organization, and this is isn’t a repeated mistake] your boss doesn’t expect you to be perfect. Fear has no place in a healthy organization, so don’t be afraid.

Response: “Yeah, this is bad. Here’s how I’ve handled this in the past, or what I suggest you do.”

If the person you’re talking to didn’t suggest you go talk to someone else about it, that means that you can take a breath – it’s not as big as as you think it is. Listen to their suggestion, listen to their experience, and respond appropriately. I’d make sure to say something like, “I just want to make sure I’m hearing you right… I’m now going to [insert the suggested next step here].” Make sure you know exactly what’s expected of you, and make sure you’re able to do it.

Response: “Regardless of how bad it is or isn’t, it’s really not your fault because XYZ.”

This one is a tricky one, because as PM’s we sometimes assume more responsibility than we should when things go wrong. At some point, things are out of our control, and that’s a message we have to keep telling ourselves. We are not all-powerful, we are not all-knowing, and we could not have know the one particular question that would’ve stopped all this from happening in the first place.

In this context, we still need to own the responsibility that we did share (as no party is ever 100% responsible and the other party is 0% responsible). Go forward, own what was your share, and don’t apologize for something that wasn’t your fault.

Response: “Hey, that’s really not that bad. Just go to X and tell them about it.”

If you hear this, you can take a breather for a second. After all, it’s not as bad as it looks! Not so fast though – you still need to own up to your mistakes. Not apologizing for something, even something small, can create an environment where teammates don’t think that honestly and humility matter. You can create a team where you can mess up and it doesn’t affect anything. You can create a culture that values “being right” over “being honest.” And, ultimately, you can create a team that simply doesn’t trust.

In Leaders Eat Last, Simon Sinek puts it clearly: “Building trust requires nothing more than telling the truth. That’s it. No complicated formula.”

The School of Hard Knocks

So you’ve owned your mistake, you’ve gone to a key person to figure out what your next steps are, and you’ve done them. The following advice comes straight from the playbook of Crema COO Dan Linhart… he shared them with me on my first day at Crema, at our first one-on-one where I felt I wasn’t doing enough for my clients, and just a couple weeks ago as I sat on a couch in our office, embarrassed and just plain mad at myself for a weighty mistake I made:

“Product Management is learned in the school of hard knocks.”

This advice was given to him by his mentor many years ago, and he has passed it on to me because he, too, learned Product Management not merely by reading and learning, but by doing and failing.

It's a hard knock life for Product Managers.

Dan began my employment at Crema and continues his encouragement towards me by reminding me that the Product Management field is one where we just can’t avoid every single mess-up. We’re going to fail. It’s going to suck. And we’re going to be better.

In other words, if your primary goal in life is to not fail, don’t be a Product Manager. If you want to succeed as a Product Manager, though, you’re going to fail… and learn from it.

To quote M. Maidique (as quoted in James M. Kouzes & Barry Z. Posner’s phenomenal book The Leadership Challenge), “Success does not breed success. It breeds failure. It is failure which breeds success.”

Make no mistake, we don’t try to fail. We don’t scour the office for shit to throw it at the fan. Rather, we approach every day knowing that failure is not the end, and that every success will come with inevitable failures. Or, to quote Chapter 8: Experiment & Take Risks from Kouzes & Posner’s above-mentioned book…

“Failure is never the objective of any endeavor. The objective is to succeed, and success always requires some amount of learning. And learning always involves mistakes, errors, miscalculations, and the like along the way. Learning happens when people can openly talk about what went wrong as well as what went right.”

Light(s) at the End of the Tunnel

Not only does failure help us not make the same mistakes in the future, or help us prepare better for upcoming situations, but there are several other benefits that come from failure (when handled properly):

1. It provides humility, and empathy for others who fail

The final moment of Zack Snyder’s (awesome and absurd) 2006 movie 300 features Spartan King, Leonidas, (along with his glistening, gritty, slow-motion muscles) as he sprints towards the god-king Xerxes. Surrounded by a barrage of arrows and blood, and a great distance away from Xerxes, Leonidas heaves his spear across the battleground to put and end to the life of Xerxes.

spartans fighting in battle
Pro tip: (most) clients don’t respond well to capes & spears.

(SPOILER WARNING) Leonidas does not kill Xerxes. Just an inch away from going through his skull, the spear slices open his cheek. Xerxes, both in fear and in pain, touch his hand to his delicate, bejeweled, royal face, now covered in blood. He pulls back his hand and looks at his blood, perhaps for the first time ever.

In this moment, the god-king Xerxes is face-to-face with his own mortality. No longer can he lead his massive armies out of arrogance, or perceived sovereignty, or out of perfection. No, he now leads out of fear. He leads out of fear because he knows, above all else, that he is mortal.

Though this example is (freaking) dramatic, it is good for us to remember that we too can bleed. We are not perfect. We cannot perfectly please our client, nor can we perfectly serve our team. We are mortal, we are imperfect, and we fail.

As such, when we see our teams, peers, or even competitors of our own fail, we see it through a new lens: empathy. We have grace for their failures, because we’ve been there too. We are quick to offer forgiveness because it has been extended to us. We can be a comforting presence for someone to process their failures with, and we can offer advice when the time is right.

2. It showcases your company’s (hopefully) healthy culture

Clients have read on your website what kind of company you are. They’ve read reviews on Google and heard from their peers why working with you is so great. And now you have a chance to show that not only are you a hard-working, creative, professional organization, but you are a humble one that admits failures, works to make things right, and learns from mistakes.

If actions speak louder than words, then company culture speaks louder following failures than when things are doing just fine. The client gets a glimpse into who your organization is at the core, not just on the surface.

The PM’s Prayer of Confession

I close this article with what I’m calling the Product Manager’s Prayer of Confession, which is an adaptation from a Prayer of Confession from the Book of Common Prayer (1789). A traditional prayer of confession serves the purpose of bringing a group of people of diverse race, sex, and age together to admit failure and announce that they aren’t perfect. This provides room for grace, forgiveness, and transparency as a community.

My Product Manager’s Prayer of Confession is meant to read at the beginning of a day or week to prepare your mind and heart, or to recite in times of a particularly weighty failure. Think of it as a mantra or creed to memorize or print off in order to shape your understanding of failure and have proper perspective and thinking about it.

We are Product Managers, and we are not perfect. We err and stray from best practices, we have followed too much the desires of our own hearts, our own priorities, or our own agendas.  We have left undone those things which we ought to have done, and we have done those things which we ought not to have done. We react poorly, communicate poorly, and prepare poorly. We fail our clients, we fail our team, we fail ourselves.
But now, as we confess our faults, we acknowledge that we are not meant to be perfect. We are not the source of all truth, nor are we the solution to every problem. We are meant to learn from our failures, and so become more humble, more empathetic, and a more thoughtful and successful Product Manager. May we continue growing in grace, professionalism, and excellence, furthering the good work of our teams and inspiring others to do the same.