How to Embrace Mistakes Without Idealizing Failures

Anant Gupta

SVP of Engineering & Data Science at Included Health



We launched a new product that was considered hype across the organization. It was a cool thing that we as users would love to have and we were driven by our own views of the world. We presented it internally at all-hands and made a big deal of it. People across the company were fairly excited about it.

The product was launched and it was dead on arrival. When we looked at the metrics we realized that it was not off by 10x, but by 100x. It was hugely disappointing as well as perplexing and we as users couldn’t understand why it was not working.

Actions taken

The team spent a lot of time thinking about what was o ff and came to the conclusion that what worked in a small sample size didn’t work in a larger sample size. In hindsight, many of the shortfalls were predictable, but at that moment I -- and the rest of the team -- was immensely excited and believed in the product. The team continued for the next six months to put the strenuous effort into improving features and the roadmap in general, but nevertheless, the product was nowhere near meeting the original expectations. I was overwhelmed with disappointment and was wondering how I should approach the team and tell them that it wouldn't be possible to achieve success.

I had to take two main steps:

  • Make the decision;
  • Communicate that decision to the team.

Oftentimes people conflate these two steps. For example, they would say, “The team will be so upset that I can’t make this decision”. Whereas, the team will not be upset about the decision itself as much about the way it was communicated to them.

To reach the most reasonable decision I had to ask myself what would be the right thing to do for the business. I would typically apply the Expected Value framework and compare the upside of me being correct and the probability of that being true and subtract the downside of me being wrong. In this particular case, it was evident that this was not going to work. I sat with the team and asked them to set the goal that would make us all happy and they came up with a number that was too low. I encouraged them to think about a goal they would pursue if resourcing was not an issue. We eventually agreed on a goal that was not hard to achieve. I also attended their brainstorming and problem-solving sessions as I wanted them to perceive me as a part of the solution, not only the one that hands over the problem.

The next thing to do was to scope out the estimates looking at the costs and the probability with your product lead and/or manager. This was not something I could involve the team in because it required the level of business judgment not everyone had. It required to look at the trajectory for the upcoming six to 12 months and assess if it would be the right investment. The manager and product lead concluded that it didn’t make sense to continue working on it. I could do nothing but agree.

After I made the decision I had to communicate it to the team. If you reached the decision by including the team, communicating it shouldn’t feel imposing and the team should accept a failure. This shouldn’t be done in a punitive way since you were with them throughout the journey. You also have to clearly communicate the decision to the organization, provide justification, and be able to address all their Whys without allowing for information to leak and people to speculate. You should own up to it and share the lessons you learned.

Eventually, everything comes down to accountability. As a manager, you can choose a path of being content since you shipped everything as required, or you can take into account a larger picture of failing to achieve a business objective. It is fine to make a bet and be wrong, but as a leader, you are assessed in the long run on your decision-making skills.

Lessons learned

  • You made a bet and it didn’t pan out as you expected. It is acceptable as long as you learn. But as a leader, you have to look at it from a long-term career trajectory perspective. If you don’t make good business judgments, you are not going to be successful.
  • You need to be involved in coming up with the solution and you need to involve other people as well. If as a leader you are encouraging risk, be part of it. Don’t conflate people with the problem. Make the decision and then look at how the people would fit in, but don’t do it because of the people.
  • A good leader is someone who is good at decision making. Embracing mistakes doesn’t imply that you shouldn’t be making good judgments. Failure is good, but it should be directed, causal and thought through.
  • While you want people to have autonomy and ownership, problems happen on your watch. You have to be accountable and own the problems. Your job as a leader is not to judge or grade someone but to safeguard that they don’t fail in the first place. If your people fail, you also failed because you didn’t help them or ask the right questions earlier.

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Anant Gupta

SVP of Engineering & Data Science at Included Health

Engineering LeadershipLeadership DevelopmentCommunicationOrganizational StrategyDecision MakingLeadership TrainingPerformance ReviewsFeedback TechniquesLeadership RolesTeam & Project Management

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