As I prepare for Amazon behavioral interviews, I have found almost every leadership principle has at least one failure question. Every time I hit it, even though I knew failure questions were just learning/growth mindset questions, I kept freezing.

To unblock myself, I tried to list my 10 biggest career failures and found I had 15 listed under 7 core concepts. I am sharing my failure categories and list (at a high level) to help you get unblocked.

The Concepts:

• Communication

• Data

• User Experience

• Business Model

• Delivering Feedback

• Hiring

• Prioritization

Communication

Three of my career failures can be linked to communication problems:

• Amazon - I let my frustration with being dismissed because I was down-leveled and probably because I was a woman in a very male-dominated organization get to me. I let my anger and frustrations show, and while I was right, it made the sexism problem worse.

• Yelp - Here I found two different communication problems impacted my career:

  • Being too detailed with executives

  • Not realizing someone saw me as a threat

  I was invited to help the executives solve a company-wide problem, after earning their trust by turning the experimentation program around in just 3 months. But when I presented, despite practice, I kept getting peppered with off-topic questions. I eventually learned that I needed to get buy-in before I entered the room.

  In another scenario, I was clearly under-leveled, even when promoted. When I did get promoted, my engineering partner saw me as even more of a threat and started trying to set the agenda for our teams without discussion, the very day I got promoted (while I was still on vacation). It created an impossible situation. But if I had read the room quickly, I could have gotten ahead of it sooner. In the end, I learned to watch for team and organization dynamics to figure out how to make my case. I also learned the importance of staying neutral when someone appears to be attacking for no reason. Use the neutrality response to buy time to get more information and build a coalition.

Data

One of the most painful career mistakes I made was not diving into the data, especially when I had the time to do it. I ended up getting my organization to fund a project that didn’t have legs. In the end, I was the one who had to take the credit for the error, even though my director signed off without asking for it. We were all over confident, my director the most. You will notice it only happened once because it has been seared in my memory.

User Experience

Two of my biggest career mistakes can be traced back to user empathy or understanding the user experience. Once at Bottlerocket and once at my coaching startup.

• Bottlerocket - This story is a combination of a prioritization failure and a user experience failure. A lot of what we built was hacked, due to the highly regulated nature of the wine industry. At the time, there was not good cart checkout platform that let you block shipping by state, which we needed to do. The only way I could make it happen was to put friction in the checkout process. As we all know now, that is the biggest reason people don’t buy. At the time, I had to balance the cost of: fraud, labor and lost sale due to inventory being blocked by flagged (as fraud) sales and complicated by lack of technical expertise. Also, every legitimate buyer who tried to purchase but we had to refuse to deliver due to fine print created a terrible brand experience - as NO ONE reads the fine print and almost non one knows about the super complicated liquor laws in the United States.

• intrico.io - At the time, it was a minor oversight. I had a client who wanted more than I could reasonably deliver in a session. I made the mistake of not telling them they had to make a choice. In the end, they gave me an unfair review on the marketplace website I had to use for supporting cash flow. The marketplace was desperate to show clients their reviews would be upheld, even though the owner knew it was unfair. It ended up costing my roughly $10K to $20K over 2 months as one bad review led to fewer bookings. The platform promised to let coaches review clients but never did. In the end, I learned to set expectations at session very carefully. I also learned to vet platforms carefully in the future. And as a PM who works on marketplaces, I know that if you don’t build trust on both sides, you end up losing income. Since I couldn’t trust the platform to have my back, I doubled down my efforts to build my own brand and refused to participate in more than the minimum with the platform. I went from one of their strongest content to producers to someone who hated working with them and did everything to avoid the platform.

Business Model

Both of my business model failures were, surprise, surprise, at startups: Bottlerocket and Catch+Release.

• Bottlerocket - The data I had said we needed to expand in a city with a university. But others on the team wanted to go to a wealthy area where we had an opportunity to be near a grocery store, which is typically a slam dunk for a wine shop. But our business model was a user-centric model and even though this was near a grocery story, there were not a lot of our loyal demographic in the area.

  We opened a store, but in the end, we had to shut it down. I have beat myself up for years that I didn’t advocate more heavily for the user-centric model over the grocery/income model.

• Series A Startup - When interviewing for my role as Head of Product, I over-indexed on my opportunity to lead a team again and so I didn’t properly investigate the business model before joining the team. After setting up the user research practice, it became clear to me that the company wanted to build a direct relationship with creators, but what the end users (those paying) needed was an API that connected to the platforms they already worked on. What should have been a heavy B2B model was actually more of a B2B with B2C model. In the end, I left shortly after concluding that the business model was flawed, but the entire leadership team was 100% behind the approach, and dissenting views were not welcome. It was my own mistake. I should have more thoroughly vetted the business model.

Delivering Feedback

I am an expert at delivering feedback to those I coach and mentor. But delivering feedback to managers and skip-levels is a trickier game. There are 2 instances where I should have delivered feedback to my skip-levels in distinctly different ways. The TL;DR is find a way to get a 1:1 and deliver the feedback in a private and comfortable setting with time for the listener to process without feeling threatened.

In one situation, I shared the feedback in a written format. While there was nothing wrong with the format, it landed more harshly than I wanted. The result was a delay in truly being heard. Eventually, it led to an investigation that proved me to be correct, but too late to help me.

In the other situation, I delivered the feedback verbally in a larger group. Again, I ended up being correct and others shared my feedback once I made it safe for the room to speak up. But it hurt my career. Instead of being rewarded for helping facilitate a much-needed conversation and change, I became hated for speaking up. If I had done some scenario planning before speaking up, I would have reduced the collateral damage to my career.

Hiring

There are two situations in which I made horrible hiring decisions. In one case, the person reported into me and in the other, I was instrumental in hiring my manager.

• My Direct Report - Working at a Series A startup, I agreed to hire someone after being pressured by time constraints and a pushy partner. It was complicated by my arrogance that I could correct for the deficiencies through strong coaching. In the end, the PM we hired was not a fit for the role, and I lost the trust of my partners.

  I took full responsibility for the bad hire and for not trusting my gut and letting myself feel bullied. But to be honest, I lost trust in my partner, who failed to acknowledge that they had pushed me into the hire. I made an additional mistake, after that hire, I overcomplicated the process, trying to vet not for my concerns but for the partners who no longer trusted me.

  An interesting observation, after I left the team, the partner who bullied me ended up making another bad PM hire.

  Hiring people is not easy. We over-index on things we really want and then gloss over the imperfections we should probably address, even in a good market. My lesson was about the expensive cost in trust when you make a bad hire.

• My Manager - While I had changed my vote after being open to the negative feedback from others on the panel, my justification for the hire recommendation let the hiring manager justify making a rash decision. In the end, the company probably lost roughly 10+ employees because of the hiring choice. While the final decision was not mine, I have never forgotten my initial hire recommendation and how influential it was in facilitating the making a bad decision.

Prioritization

The two items on my list related to prioritization are (1) timing of taking a new role and (2) not putting effort behind marketing rather, I focused on quick cash flow sources.

The energy in a startup can be addicting. When I was at Bottlerocket, I loved the team and mission, it was my family. And so, I stuck around too long. That put pushed my career back by 10+ years, it is part of why I have been down-leveled for the better part of a decade and I am still trying to dig out from underneath. Note: This story is not one I share in interviews, but for those who look to me for career advice, it is a cautionary tale.

Then there is my startup: intrico.io. I don’t love how I look, and so I have dragged my feet on creating YouTube videos as marketing materials. This has probably cost me six figures per year. If I was to start over again, I would have saved more money and come to my startup with a budget for marketing. This budget would have included turning down small cash flow projects for investing in marketing efforts. Maybe next time around.

Summary

I have shared these stories to inspire you to think about your own failures and what you learned from them. And I will admit, I hope writing them out in long form will help me remember them when I am interviewed next week.