Want to Succeed? Fail First.

Failure is great. Talk about it, obsess over it, and it will teach you more than success can

When you’ve been developing products for as long as I have (15 years to be precise), you’re bound to hit a few roadblocks. And bumps in the road. A dead end, or two, or five. But that doesn’t detract from your long-term path, it just means that you need to update your roadmap accordingly. 

I can’t say I have a favorite product that I’ve worked on, because what I’m most passionate about is the method (read: madness) it takes to develop great products. 

Currently, along with my team, I work on several different products at Microsoft to enable frontline workers in several industries to help them become productive through effective and efficient collaboration. This is different from the consumer-oriented products or video analytics-based products I worked on before. But from the beginning of my career, the winning formula has remained the same.

Research > Build > Grow

To quickly hit the rewind button, I began my career engineering at small startups before moving to product management at large companies like Microsoft and Amazon. Interestingly enough, the way that development works has stayed the same; sometimes speed, scale and focus change, but the fundamentals don’t: Research > Build > Grow. 

An element I put major weight on is understanding the pain points of customers at a deep level; capturing their pain, and determining what important processes are the most painful. Building around pain points requires both technical mastery and a strong sense of empathy — by putting yourself in their shoes, you can begin to understand how a customer feels while observing and navigating your product, and what challenges they may face.

For example, while building a communications product for users whose key roles include dealing with national disasters, my team learned about the challenges faced by limitations in funding, resources, and communications. Our targeted users needed to face these issues with minimal sleep and with high safety concerns. To tackle this situation and create effective communications that reduced confusion, planning ahead and building a structure in their communications was of utmost importance.

In this situation, we spent time at the emergency ops centers and talked to people at various levels, gained empathy for the pain points, and designed the product with their points of view in mind. 

Sometimes, it’s not this simple. 

Success is Always Predated by Failure

It takes a large number of iterations to build any product, and getting there is never a straight line. But without those failures, we’d never reach our successes. Without those lessons learned, the interactions, the long nights, and painstaking roadblocks, the taste of success wouldn’t be half as sweet. 

Whether you’re the CEO of a public company or just out to dinner with peers, we’re all much more comfortable discussing our successes than our failures, even when they’re an essential part of the real story. When we do acknowledge failure, it’s often in hindsight, once there’s enough success to balance it out. 

This creates success bias, and deters others from understanding that these failures are as important as the wins themselves. Failing should be a sign that you’re finding your way to the right track — not that you’re lost. Failure means you’ve earned the confidence to say you’ve taken a risk and learned from it. It’s never the end of the road, merely a stop along the way to something incredible. 

Let’s take a look at another example. At Amazon, I was focused on increasing customer engagement with Alexa shopping. The advantage was easy enough to understand: shopping by voice fit into the flow of your daily life seamlessly. It’s a single, simple step. From the consumer experience, it simplifies things. 

Except, it didn’t. 

After the initial launch, my team observed it working really well in some cases (reordering, specifically) but in other regards it wasn’t as successful. 

So we went back to basics. 

We talked to customers and tried to understand their impact. Simply by asking “why aren’t you shopping,” we weren’t able to get clear data — because the consumer didn’t even know. It’s not that they were sparing our feelings, or were hesitant to give us negative feedback. They were unable to go one level deeper, and ultimately my team realized that they relied on visual data to make informed decisions. That’s why they were confident reordering via voice, but with new orders, found that the users needed that visual confirmation before purchasing. 

By reframing the problem, we came up with a better solution: a way to send purchase options to the users’ phone when they initiate their order from Alexa so that they can research it later — visual aids and all. 

It took a few iterations to get to this solution. Multiple failures, and plenty of roadblocks along the way. By working through failures in the product fit, we were able to optimize what worked, what didn’t, and ultimately reach our success. 

The Mindset Method

The boldest, most creative ideas are also the riskiest and require the most iterations. When projects get difficult, a defeatist mindset is easier to adopt than a growth mindset. A growth mindset involves accepting inevitable growing pains, but is also how we learn from our mistakes. Failing does not define us, how we pivot in response is what ultimately determines how successful we will be. 

A problem is not a failure, but it’s an indication that you can do better, and a call to action to understand what process or decision led you down this path. More often than not, you needn’t abandon your work or lose motivation. You can just take a deep breath, or two, or five — then take another angle. 

If you haven’t had the luxury of failing lately, follow along here. I’ll be speaking with influential leaders who had their fair share of failures on their road to success, as well as divulging a few of my own. 

Buckle up, there are some bumpy roads ahead. But the destination is always worth it, and the air time from the bumps is thrilling!