Fail Fast, Learn Faster: A few lessons from my Journey

I was sitting in traffic driving home from Palo Alto to San Francisco, and I felt a sense of pride as I reminisced on my past few years at Microsoft and the journey to come. In my short time in the “real world,” I’ve learned many lessons from my successes but more importantly my failures. I've gone through many ups and downs like "What am I doing with my life?" to technical challenges like “What exactly is a virtual machine...?”

Now I don’t claim to know everything, and I have a longgggg way to go until I’m fully embracing my North Star, but I'm proud of where I’ve been and excited by where I’m going. In retrospect, I thought about the lessons I've learned in my short tenure working in sales and felt like I should share with the world.

Top Lessons:

Fail Fast - It was about a month into my career and I was ‘drinking out of the fire hose’ feeling quite overwhelmed. I traveled to see a customer with a veteran salesperson who unfortunately got the flu and asked me to fill in for her. With shaky knees I attempted to present one of our products, answer the customers questions (many of which I answered wrong), and tried (and failed) to seem like I knew what I was talking about. This may not have been the most successful meeting, but it helped me progress and improve in my role. It made me realize that if I’m afraid or hesitant to do something, well there’s no time like the present to get out and do it. The faster you fail, the faster you learn from it, and the faster that leads to success.

Be curious – Sometimes I get so focused on closing a deal that I fail to look at the customers business and see how I can actually provide value to them. I get so blinded in selling my products, that I forgot we’re trying to help our clients achieve their vision and solve their problems. It isn’t until I get genuinely curious, put aside my agenda, and have empathy for our customers problems that true opportunities start to form. In doing so, they begin to look at me as a trusted advisor as opposed to just another salesman. It all boils down to, how can I truly help you serve your customers?  

Form a Core Group - My first year was filled with many ups and downs. Often, I second guessed myself on making the right decision or if working in sales was really aligned with my goals. I formed a weekly core group meeting with 4 other new hires from across the country. During these meetings, we were honest about what we were struggling with, what we were doing well, and what we were looking forward to. This community kept us accountable for our growth, challenged us to step out of our comfort zone, and provided a safe place to confide in each other. To this day, I consider those in this group some of my best friends and I’m thankful for their support.  

Own your age - I'll admit, there were a few times in my role where I flat out lied about my age. When I started in my role, I was afraid to be perceived as the 22-year-old kid who knew nothing about technology or our customer’s business. It took me a while to I realize that as a millennial, I bring a unique perspective on how technology is engrained into how we work and how it can impact the world. This outlook is critical for the marketplace as we continue to embrace the technology revolution and as millennials become more prevalent within the workplace. Although we don’t provide the skillset of a 20-year veteran technology expert, we still provide a fresh new perspective and eagerness to be of value.

Ask for feedback – I was once told that feedback is a gift. So often I get stuck in my own ways that I fail to consider other ways to solve a problem or build stronger relationships. Once a month, I set myself a reminder to seek feedback from those that I work with on a constant basis. Whether it’s my coworkers, customers, family, or friends - ask for feedback on what you’re doing well and what you could improve on. It goes a long way in building trust, accountability, and a further way to advance your growth.  

Focus on a Goal – Even if I’m not the most knowledgeable one in the room (which is most of the time), I’m still accountable for bringing our team together to focus on achieving a common goal. Whether or not these are coworkers, partners, or customers, we need to create a shared vision to work towards together. I often view myself as the quarterback that either passed the ball or hands it off. Sometimes I run it on my own, but like Tom Brady it’s usually best when I involve my receivers. 

What’s your metric? - One of the most impactful books I’ve read is ‘How Will You Measure Your Life?’ by Clayton M. Christensen. The message of the book is that if everything boiled down to a single metric, what would be the metric that you measure your life by? My personal metric is this - How many people can I affect in a positive way that are doing better after they met me as compared to before they met me. Whether it's a friend, a customer, the person checking my bags at the grocery store, or a person I bumped into on the street – how can I add value to their life in a positive way?  

Like I said, I have a long way to go and much more to learn. But I’m energized by my learnings that will set the foundation for much more to come.

 I welcome your feedback on these lessons learned.

Alex Kremer