The fear of failure looms large for many product managers, regardless of level. It’s easy to understand why: in some organizations, a single misstep can lead to far-reaching consequences for users and stakeholders. In a career where precision is paramount and foresight is essential, it can be extremely difficult to deal with mistakes–especially the ones we’ve made ourselves.
While it may seem counterintuitive, making mistakes is an essential part of any product manager’s journey. In fact, many of the world’s top technologists, startup founders, and artists agree that their best work has been achieved by seeking out new and oftentimes risky opportunities–and embracing the mistakes that come with them.
In his book Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration, Pixar Co-founder Ed Catmull puts it this way: “Mistakes aren’t a necessary evil. They aren’t evil at all. They are an inevitable consequence of doing something new (and, as such, should be seen as valuable; without them, we’d have no originality).”
In this article, we’ve spoken with experts–product owners, founders, and enterprise PMs–in order to discover how they metabolize mistakes and turn them into opportunities for growth.
Thanks to Kristen Poli for crafting this piece for GoPractice.
Kristen Poli is a product leader and tech journalist.
She previously held the position of product manager at Contently and was the product management lead at Curacity.
Her articles have been published in outlets like WIRED and Hackernoon.
These experts include:
- Kriti Pinto, Co-Founder of Docuseal
- Corey Hobbs, Director of Product at Daily
- Jake Weber, Founder of Printernet
- Vinay Aradhya, Principal Product Manager at Thomson Reuters
- Jenna Coleman, Co-Founder of Atticus, Builders Backlot, and Lynn
Is there a difference between a ‘good’ and ‘bad’ mistake? If so, what sets them apart?
While our experts’ opinions differ, they agree that all mistakes are not essentially bad. It’s important for product managers to reflect on past failures and successes in order to prevent ‘bad’ mistakes–characterized by their relative avoidability–and encourage ‘good’ ones, which can be made by pushing boundaries, trusting customers, and taking calculated risks. In addition to creating a culture that fosters ‘good’ mistakes, product managers can reframe success and failure as learning opportunities to foster continuous improvement and personal development.
‘Good’ failures contribute to long-term successes
Absolutely. A “good” mistake is one from which you and your team can learn and grow. These are the mistakes that, although they may cause short-term setbacks, ultimately contribute to the long-term success of the company. They often involve taking calculated risks, experimenting with new ideas, and pushing the boundaries of innovation.
On the other hand, a “bad” mistake is one that is avoidable, costly, and potentially damaging to the company’s reputation. These mistakes often result from poor decision-making, lack of foresight, or neglecting to learn from past failures. For bootstrapped startups like ours, it’s essential to encourage a culture that embraces good mistakes while actively working to minimize bad ones.
‘Bad’ mistakes are continuous; ‘good’ ones are discrete
On a product level, a good mistake is one that you made in service of a customer. There are lots of times when you’ll get a set of requirements that seem a little obtuse to what you’re doing, but are in place to make certain customers happy. In these situations, things may fail, and you may have to create workarounds to get things back on track.
A bad mistake is one that you continually make. Bad mistakes create ripple effects in your organization, and create churn: they lead to engineers feeling burnt out, designers feeling burnt out, and marketing feeling burnt out, all because you’ve built an unsustainable product or feature (even though it might be flashy).
I’ve learned that bad mistakes happen when product managers pile on concessions again and again. I find this often happens with technical debt–there are resource constraints, customer timelines, and expectations to deal with. With teams that I lead, I work to ensure that the customer knows the cost of certain features, and can manage trade-offs; whether they’re financial or not. It’s important to give customers the ability to choose one priority for themselves over others–they get to decide their own fate.
The success/failure binary can be limiting
I think it’s beneficial to frame your work, or your goals, outside of the binary outcomes of success or failure. It’s more useful to ask “what are all the ways I will gain from this and benefit from this project?”
For example, I recently experimented with launching a podcast. Even if my primary, external goal of building an audience fails, I’m still meeting interesting people, getting better at conversing, and learning more about my interests. When you think about it this way, there’s a nearly infinite amount of things that can be defined as successes.
It’s not always easy to keep this in mind when reaching for an ambitious goal, but there are always larger, more important long-term wins in every project. I think that picking the right project or the right goal is more important than your eventual success or failure. By using this type of systems thinking, I can prioritize which projects to focus on rather than chasing a trend or external measures of success. As the artist Tom Sachs says, the reward for good work is more work.
What strategies do you use to analyze and learn from mistakes?
“Learn from your mistakes” is an adage that’s frequently repeated, but often underexplained. For some product managers, developing smart systems to analyze mistakes, summarize learnings, and make commitments is the best way to prevent unnecessary mistakes from occurring. Experimenting with postmortem analyses, taking full accountability for missteps, and embracing iterative practices can help product managers turn past mistakes into future opportunities.
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Conducting post-mortem analyses
When a mistake occurs, I believe in digging deep to understand its root cause rather than just addressing surface-level symptoms. This involves examining processes, communication channels, and decision-making frameworks to identify where things went wrong. Here’s my approach:
- After any significant project or decision, we conduct post-mortem reviews to evaluate what worked well and what didn’t. These sessions provide valuable insights into our processes and help us identify areas for improvement.
- I believe in taking an iterative approach, where we continuously evaluate the outcomes of our decisions and make adjustments accordingly.
- Learning from mistakes is only valuable if we use that knowledge to implement changes. Whether it’s refining our processes, providing additional training, or adjusting our strategy, I’m committed to taking concrete actions based on our learnings.
By embracing a culture of continuous improvement and learning, we can turn mistakes into opportunities for growth and innovation, ultimately propelling our startup forward.
Taking accountability–and being proactive
The only ‘bad’ mistake is one that you can’t learn from. People deal with failure very differently. I think it’s very important to be able to acknowledge failure, call it what it is, and take ownership of it–even if what happened wasn’t a personal failure. If a mistake is made, I have to take accountability for whatever portion of the decision I was responsible for, and tell the rest of the team that we (as a product team) did indeed mess up.
Sometimes it’s about admitting mistakes proactively–we’ve sent emails to customers before saying “hey, we screwed up.” When a customer sees you take ownership, they know that you’re listening and that you care. Some people think this is only important for customer support, but building trust with customers is important for product teams as well. After you make a mistake, it’s important to define what you’ll do differently next time, and how you can apply your learnings towards what’s coming next.
What mistakes have you made in your career? How did you learn from them?
As a product manager or founder, mistakes can be difficult to recon with, especially when large groups of users are involved. That said, it’s important to recognize when mistakes have led (or have the potential to lead to) valuable learnings and pivots. In these examples, Jenna and Vinay both used mistakes to supercharge their efforts and build even better products by admitting failure, connecting directly with users, and working overtime to compensate for unexpected technical or strategic outcomes.
Failure and success can be concurrent
I don’t have a theoretical background in product. Everything I’ve learned, I’ve learned through practice (and lots of failure).
With Atticus, there was a huge demand for our product. Our only competitor was Mac-only, and most of our authors (potential users) weren’t working on Macs. That competitor had zero interest in branching out to Windows. There was so much demand that my co-founder and I put together a bare-bones version of what we wanted Atticus to be– after all, people were sending us memes that said “take my money!” As a result, we launched way too early.
We called the first version of Atticus a beta. It was supposed to be a closed beta for people who signed up knowing it was an incomplete product, but of course, the beta didn’t stay closed. Suddenly, the word spread, and we had people buying the product who didn’t understand what it was. People just assumed that everything they experienced that was “wrong” was a bug, but the product was kind of unfinished. To make things worse, account creation emails didn’t go out automatically on launch day, so we were sending emails manually all day. I think that’s all we did!
So–failure is going to happen. You can’t not fail when you’re building any product. In this story, we were profitable in six hours–but I still ended the day feeling closer to failure than success. I learned a lot about message control very quickly. It was painful; but I learned that you can have failure and success at the same time.
Mistakes can lead to pivots
At one point, I was working for a consulting company, and my team and I were advising an on-demand ride-hailing company. Our customers owned fleets of buses and cars. In order to develop a new on-demand ride-hailing platform for our customers, we did a lot of market research, which included making prototypes and working directly with drivers. We reached out to every driver we could–it was a ton of administrative work.
Unfortunately, we missed out on understanding the market holistically and weren’t looking at the big picture. We caught on to the market trend of on-demand rides quite late, and had to revisit our roadmap. Then, because this was back in 2021, Covid quickly caused the entire tourism industry to decline. People weren’t as interested in taking rides, especially group rides.
So, we were able to pivot: instead of picking up and dropping off people, our drivers delivered items–many delivered medications, gifts, even Covid tests. People couldn’t go to FedEx to drop off packages anymore–they were quarantined and isolated. As a result, we were able to provide an on-demand courier service.
With this pivot, we were able to reap the benefits, even in a crowded marketplace. We didn’t have to make significant changes to our software or business model. Eventually, this product split into two different product lines, and we created a portfolio of on-demand services.
I wouldn’t say any of this was a mistake, though perhaps others might. The team had the grit, perseverance, and dedication to really understand the market and user pain points, and the willingness to pivot. After this happened, the whole team started thinking differently, focusing on the future, and asking questions like “how can we ensure our product will succeed three or four years down the road?”
Conclusion
For product managers constantly striving towards perfection, mistakes can feel like the end of the world. While it can be difficult to take accountability for (and learn from) mistakes, they’re an essential part of any product manager’s journey. By determining the root cause of mistakes, addressing mistakes directly with stakeholders, and proposing changes to prevent the same mistakes from happening repeatedly, product managers can turn failures into opportunities. Making a mistake is often the first step to building better systems, products, and outcomes for users.
Illustration by Anna Golde for GoPractice
