Leading a Company from the Heart

Every so often I come across a book, article or video that really strikes a chord. This week I discovered one such video by Justin Rosenstein, co-founder of Asana. The principles and advice that Justin imparts in this video were really inspiring and deeply motivating. Any budding entrepreneur or existing company leader should watch this!

Cliffs Notes

Note – these are not in order of how Justin relays them in the video. I have categorized these points into areas that I feel are applicable.

Personal Psychology

  • When people tell you something is impossible, be very skeptical.
  • Be in a world where we help affirm and help each other instead of one where we tear each other down.
  • Wake up every day and realize you are alive. It is easy to get distracted by the day-to-day.
  • 50% hedonist / 50% contributing back. Jusin talks about how he lived his life by consuming as much resource and taking and enjoying everything he could without giving much back to the world. He later realized that doing this is not how we achieve a sense of deep satisfaction and joy. Instead, the way we achieve this is by contributing back to the world.
  • Don’t always think about our own interests and instead thing about humanities interests as a whole.
  • Work life balance is not necessarily about the hours you put in each week. You can put in 60 hours a week but after a few weeks you start to burn out. Work life balance is about knowing when to work hard vs when to take the time to reflect and take a deep breath.
  • The most important part of being a leader is managing your own psychology.
    • There is a voice in your head that is self doubting. It sounds like you, but it is not you. Imagine this like an annoying judgmental roommate living in your head. Every time you hear this voice appreciate that it is trying to be helpful, but it is not you and you make a decision from a different place.
    • Sometimes you find yourself thinking that you are not qualified or shouldn’t be in the position you are in. This is a universal psychology problem and is called imposter syndrome. It is just a voice in your head that is telling you that you are an imposter and don’t fit in.
    • There are two stereotypes of people, one is very lackadaisical and don’t seem to get much done and the other is someone who is intensely engaged and has passion for what they are doing and always has a little sense of stress and fear all the time. Both are not ideal. Instead look think about willful intention with non-concern for results.
      •   On the best days you can be fiery and passionate. Sometimes things do not work out. The world will go on. Fight if there is still a chance of getting something to work, don’t just give-up.

Leveraging Ways To Make Impact

  • It is possible to achieve the satisfaction from helping others but also realize that your time and resource is very limited. Justin explains that you could spend your time doing philanthropic things like building a house for someone but there is opportunity to leverage technology to help a far greater number of people and have impact at an enormous scale.
  • It is more exciting to contribute to the mission of a technology company that has the power to impact the world than it is to build one house at a time.
  • It can offer a company more leverage by  contributing to tools that will help the company as a whole instead of managing people.
  • Give others the tools to leverage themselves and make an impact.

Romanticized Notion of Project Management

  • Romanticized notion that Project Managers spend their time constructing a vision, blazing a bold trail  forward, contributing to strategy meetings and generally thinking at the high level abstraction.  When the reality is 90% of the time is spent on the friction and overhead of coordination.
  • Huge amounts of time not doing work or contributing to areas that you are passionate about. Instead doing “work about work”. Example – reading and writing e-mails
  • Justin would wonder why everything was moving so slowly and spend time fantasizing  about everyone being telepathic and knowing what everyone else was doing.

Solve Big Problems

  • Clearly the problem of Project Management experienced led Justin and Dustin would get together and explore the notion of making it easier for teams to communicate.
  • Be a doer more than a dreamer. Dustin, who was the VP of engineering at Facebook at the time, stepped down from being a VP just to work on solving the project management problem.
  • Justin and Dustin realized that the problem was not isolated to the likes of Facebook and Google, this problem is one shared by all of humanity.
  • Realize when the solution becomes a Facebook sized opportunity.
  • Realize that we can come together to solve some of the worlds biggest problems, no matter how big they seem.


  • Come together.
  • Align our energy in a common direction and vision.
  • Execute this together.
  • Hopefully harmoniously and in sync.
  • Realize that we are not a series of teams competing with each other but instead we are a single company working towards single ends.
  • We need to have the will to come together and explore.
  • We need to have the tools, skills and expertise to execute on that will to succeed.

The “One” Project

  • The single human project for global thriving.
  • All coming together and all contributing our unique skills to do something great in the world.
  • This is not just philanthropic endeavors but includes other companies like Lift, which enables car sharing to allow us to have fewer cars on the roads in general.

Avoid Focus on Money

  • Don’t focus on getting as much money, accolades or collecting as much resource as we personally can. This is a fool’s errand in terms of happiness.
  • Instead focus on the opportunity to contribute to the giant opportunity we have to make the world a much more exciting place.


  • Thinking about values are key to a companies success.
  • Values are something you repeatedly come back to. They should be used almost on an hourly basis at meetings.
  • Mindfulness
    • Knowing what you are doing. Reflect clearly and deepen our understanding of what we want to be doing and if this aligns with our values.
  • Balance
    • It is very tempting to choose one extreme or another when faced with a decision of what to do.You can do X or Y and decide to choose to do X. Although by choosing one direction you get a lot of clarity but in general these extremes are very bad and lead to negative consequences.
    • It is not about compromise and trying to pick from both. Instead you want to find a middle way that transcends the negatives of each approach.
  • Radical Transparency
    • Always take copious notes and send those out to everyone at the company. This includes notes from board meetings.
    • The only thing not shared is personal information.
    • Leads to a lot of trust.
  • Company as Collective of Peers
    • You could be out there running your own company, but sometimes it can be just as rewarding to work on big ideas.
    • We are all visionaries if we have an environment where we can come together and collaborate.
    • Hire extraordinary people who could be running their own companies but instead come together to form a “super group”.


  • Directly Responsible Individuals (DRI)
    • Anything in the company big or small has exactly one person who is the DRI. They may have a huge team behind them, but they are always accountable.
  • Company Calendar
    • Team leads at the company come together and say by a certain date what they plan to achieve. All of the company can see this commitment.
    • Each week there is a report on the commitment and there is a round of applause if the milestone or task was achieved. This achieves a sense of comradely in that everyone can talk about how they came together to achieve the goal.
    • If something was not achieved, the DRI has to run a five whys process and then send these notes out to the company so everyone can learn a little more about how to avoid the same mistakes.
    • Judgement free process.

Leadership Styles

  • Every leader wants the team to get lot done, have accountability, make sure that people do the things they commit too. This often gets stuck between two leadership styles:
    • Soft leadership – “Oh, you missed the deadline? ok, no problem.”
    • Hard leadership – Yell at people and tell them if they screwed up.
    • Middle ground – If these are not appealing, institute accountability by having individuals  commit to a deadline in front of not just their team, but for the company to see. Every week have individuals report on the progress, this leads to communal pressure. If something was not done, have them run a five whys process and send out the notes to the entire company.

Decision Making

  • Typically the question comes up if we should do something the right way or do something the fast way. Both extremes are clearly terrible.
  • If you try to do things perfectly then the market will pass you by before you are ready to launch.
  • On the other end, if you just throw spaghetti at the wall and hope to see what sticks then you can really tarnish your brand.
  • The middle way is the “pragmatic craftsmanship”. Knowing when to take more time or less time with a given case.

Company Meetings / Discussions

  • TGIF All Hands Meeting
    • Go round the room and speak about one thing you are excited about and one area where we could be spending more attention. The last point is an opportunity to explore the problem and take action.
    • Energy accumulates when everyone speaks about the things they are excited about.
    • Never end up in a situation where a problem festers for months and gets out of control.
    • Everyone is very open and honest about contributing to the discussion.
    • The company gets a little bit better each time. Eventually there will be few or no areas that need attention.
  • The five “whys” – Keeping asking why and going deeper into the problem. By the time you get to the fifth “why” you should get to the root of the problem. Address each of the “whys”, don’t go overboard but make sure this is addressed for the future.
    • Take the time to stop and reflect and ask these questions. This should lead to a more stable company or product.
  • Roadmap Week
    • Every quarter (or episode) hold a roadmap week where the whole company stops doing normal work and is placed in committee meetings contributing to company roadmaps. For example, there would be a committee for mobile or one for design.
    • Committees can include anyone from the company. This could be a support person who has read all the complaints about mobile and wants to be on that committee to be the voice of the customer.
    • Committees are given advice on values before hand. For example, the mobile committee understands where this fits in with the overall vision for the company.
    • It is entirely up to the committee to understand where is the company now and where the company could be going. Understanding the options, what are the pros and cons, who should work on this and put forth a plan on what we can do.
    • Trust people to make the right decisions.
  • All Hands Company Calendar Meeting
    • Team leads, and sometimes individuals, come together and commit to a deadline for a milestone on the calendar. This is visible by the entire company.

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