Below are things I learnt from experience, readings and attending talks (eg Y-Combinator online startup school). Ongoing - I update this when I remember / encapsulate realizations.

Communication about or during work

• Radical transparency (like Ray Dalio describes in Principles) is central to allowing everyone to make the best decisions they can. The more accurate and comprehensive one’s picture is reality is, the more informed their actions can be. Find ways to share and update others about relevant information.
• Clear meetings: what are we meeting about? agenda points by everyone in advance. There was one meeting that had a long list (8 things) to discuss without clear desired outcomes for each. I took the time to categorize desired outcomes. This paid back by making all following meetings more effective. The task categories are: Brainstorm together about X, find info/research X, reach consensus about X, divide labor of X task. Finally, before ending meeting, what did we learn from this, where are we documenting it? What tasks are we each taking out of this and when do we meet again? Accountability.

• You will get frustrated. Unless you are a saint. It’s ok to reach this point, but not ok to not address it. When I feel frustrated, I take a break, try understand what it is through self-awareness and reflection. It may be a misunderstanding, fundamental disagreement, a personal need that is being challenged (e.g. feelings of autonomy, competence, relatedness). I break down and organize thoughts for myself first, then message or call the relevant people. Reading about psychology helps tremendously (e.g. self determination theory, NVC / non-violent communication).

What am I working on?

• in a startup nothing moves forward unless someone moves it forward. the gears only turn if you drive them.
• modulate between research and explore on a macro view, then translating that into executing in small steps/splitting work. Executing in the present moment is the only way: do not dream about paying others to do it. There is no money, do the work, no matter how rudimentary (more on this later).

Sales:

• Not evil because it is about meeting people’s needs. Sales is mostly about listening, not about persuading or manipulating anyone. For designers, sales is a natural extension to talking to users: it extends the conversation beyond the “what are you struggling with” and into “how can I help you with this?” If you can truly help, they see proof of it, they trust you, they like you, then they may buy from you (some of this sentence is from Gitomer’s Little Red Book of Selling). If you are resistant / shy about getting paid, you may have an internal hurdle to overcome. Money is after all a medium of exchange that represents value. Someone parts with their money when the exchange brings them an equivalent value: we all naturally have a “willingness to pay” for what we value. It is subjective, not everyone needs the same things as badly.
• 1. prospecting : who might be interested? user groups? where do they go, where can we find them?
• 2. conversations: talk and learn, is this the right product for them? what problems are they facing? might there be perceived risks from their end about committing to your product?
• 3. closing: the buying process.
• “Build and they will come” is not guaranteed and usually untrue. Address early adopters of a hair on fire problem. Hair on fire problem is one that needs to be urgently solved, no matter how ineffectively. Read about sales: it’s not about manipulation, its about giving people what they want.
• “adoption curve”: there is a bell curve of who is willing to adopt novel things first. Some people are very resistant to trying new things: it is absolutely expected that they will say no. You target early adopters and innovators, those who know there is a potential upside as well as downside. The early adopters are a fraction of the population (2.5%). This is the reason why it is important to go reach far and wide. In other words, rejections are not necessarily because you are bad at sales, but because 97.5% of population are not ready for the unfamiliar. Accept no and move on, it is a numbers game. https://www.youtube.com/watch?v=xZi4kTJG-LE

Letting go of perfectionism:

• difficult to build from scratch. There is no “how to” manual, because startup/innovation is inherently novel. You are betting against the consensus of what already exists, so there is a limit to how much one can follow existing methods before converging towards something that already exists. Makes you more empathetic of developers and startups in general.
• execution > planning because first draft is going to be bad anyway. “The first draft of anything is shit” - Hemingway. The positive effect of time spent planning diminishes after a certain time. Find out when it’s time to stop planning and start doing. Doing will result in learning and adjustments as you go. Much of the habit of trying to foresee problems in advance, is the mind trying to resolve the discomfort of uncertainty via thinking. But thinking is not action, and only the act that resolves a perceived problem will convince you that it’s not worth worrying about. Quantity leads to quality. No one is counting, only you are. Sometime the first take is the best take anyway. The best time to nurse an idea is the moment it’s born. Just do it, now.