The Pitching Skill

What’s the secret to unlimited opportunities? Why do some people get more opportunities than you? We grow up learning that you need to work hard and smart. It will result in more time, money and freedom. We can then work on whatever we want. We undermine the role of pitching our ideas and ourselves.

I started my career working on custom boot and build systems.  I got the opportunity by sending out an email to a stranger on a mailing list. I sold them the idea through my profile that I may be able to solve systems problems. I demonstrated that I can solve a C programming problem and work through the solution. The reward for solving that problem was permanent employment with salary and benefits. My next goal in two years was to join a graduate program. This time I had to write a good essay to study computer science at university. I did not practice writing good essays for two years. I wondered, why I did not practice essay writing for years? I was not taught how to pitch myself.

Pitching became second nature when I started a company. If you pitch well, you can raise money and grow your company. Pitching teaches you a lot about yourself. A person we gave an offer to asked us, "Will you be able to support remote work?". I knew we lacked experience in managing a remote team member. I also lacked the ability to convince them otherwise. Every conversation felt like I had to convince someone else that our idea was worth it. A good pitch can give you access to an otherwise impossible opportunity.

The pitch-do-check loop will help you build credibility over time.

Pitching is to convince someone (yourself included) that your future work is valuable. Don't confuse pitching for doing the actual work. Doing the work makes your old pitch authentic. Your initial pitch will not get any takers, pitch anyways. Do the pitch and the work. Check your work and refine your pitch. The pitch-do-check loop will help you build credibility over time.

Do you have a rejected idea?  A pitch for your startup, book proposal, a new idea in your team. Start with any rejected idea. Do work towards it for a week. Refine your pitch. Share the new pitch with progress. Get feedback from another person. It takes time for your work to speak for itself. Pitching is a skill that helps you jump that queue. I was an outsider to computer vision. I spent a long time pitching and building products that use computer vision. The ability to pitch mixed with a lot of luck has helped me land great opportunities.

The important thing is to take that first step. Bravely overcoming one small fear gives you the courage to take on the next. - Daisaku Ikeda

A lot of individuals are never exposed to the benefits of pitching well. They've closed themselves to a large number of opportunities.   Daisaku Ikeda writes, "The important thing is to take that first step. Bravely overcoming one small fear gives you the courage to take on the next." Each one of us can take that first step. I would love to live in a world where each individual has access to the best opportunities. Pitching their grandest ideas and doing their best work.

Transparency in startups

Have you ever wondered why your manager hides certain information from you?

My experiments with transparency span being a founder and early-stage startup team member. The phrase I am tired of hearing during my working life is that information is “need to know basis”. This statement undermines the person asking you questions. I've documented the intersection of my values with an adaptation of my real life.

Imagine you are a founder of an early-stage startup. You run into a situation where you don't have enough cash to run payroll next month. As a leader, you can either share this information with your team members, not share till they ask or do nothing. Your team members put a lot on the line to join you and don’t share much of a financial upside if things do go well. You owe the transparency to them. Doing nothing is taking the path of least emotional resistance. It erodes trust in the leadership. I've met startup employees who would never work for a founder they worked with in the past. These are the consequences of being a bad leader.

Telling your team you don't have money to continue paying them can feel scary. To be able to share this with your team is hard, but a win-win proposition. It helps your team build confidence in leadership that shares hard truths. The emotional process you undergo will make sharing hard truths easier for you. A side effect of this is that your team will reshuffle. If someone believes in your company's mission, they will double down on your company. If they have doubts, they will leave. This helps cement the culture of openness and transparency in your founding team.

Let's say you decide to not share anything about the poor financial situation. You get lucky and you find that paying customer for closing your next round of funding. Everyone on your team is happy. Your team size doubles. In a few months, the same customer is unhappy with your product. What do you do? There were no consequences of not sharing important information last time. You don't share anything again, this time with double the team size. You have now cemented a culture of not sharing hard truths with the team. Looking up to you, your leadership team does the same thing with their teams. Over time no one in your organization is sharing hard truths with each other. Those who do, look like outsiders in your organization. The growing information gap about hard truths will lead to an ineffective organization. Everyone will be second-guessing their leadership, peers and managers.

You can’t develop genuine character and ability by sidestepping adversity and struggle." - Daisaku Ikeda

Transparency is about treating people right. Leadership is about decision-making under ambiguity. Values guide your thinking in ambiguous situations. The value of transparency helps people share their true opinions. Leading with transparency is not easy in a large number of organizations. Let's challenge ourselves to building organizations of greater transparency. Here's a quote that has served me well in my challenges with transparency. "Rise to the challenges that life presents you. You can’t develop genuine character and ability by sidestepping adversity and struggle." - Daisaku Ikeda. A culture of transparency is hard to build. Anyone can start creating a culture of transparency. A good starting point is to start writing down the decisions you make and how you made them. People will notice how you take the messy glue of human emotions and transform it into a great culture.