This is a collection of random notes and learnings from different sources about my journey to leadership. In no particular order any resource is more important than the other. I write this mostly to my current and future self for personal reflection, but feel free to learn from this post or the materials mentioned. This is a live document and will be updated (hopefully frequently) whenever i find something useful. The context here is leadership in software engineering, not necessarily applicable or not to other industries.

You may ask "why leadership?" and i ask myself the same question again, and again, too. To put it in another way let's take a more practical example: "I want to be rich". So everyone wants to be rich, maybe 50% of them want to know what it takes, maybe only 1% of them actually do the work needed, most probably only 0.1% of them succeed. On a similar note, I want to embrace the challenges and make good use of the work i do. I notice i find joy teaching exchanging knowledge and experience with people. I want to grow people, alongside building my own business, so all in all i have nothing to lose but everything to gain.

Professionally i have 0 prior experience as a full-time leader in any organization. However with the aspiration to become one, i have been paying attention to the surrounding environments, from my families how people interact, from schools where i notice different teaching styles that suit different learning styles and subjects: certain majors requires learning by heart/book the academic foundations like math, physics and chemistry, some others like engineering focuses more on the practical side where technology changes is almost always faster than most schools and teachers can adapt to.

I used to work as a part time English tutor, I love teaching, more like spreading good knowledge to others. There is a problem, however, is even when you're the best teacher in the world, if the students don't spend time and effort to improve themselves, there is little to no improvement after all. So all in all, leadership is similar in a sense that you spend your time growing other people. To make leadership effective, it's required to have good environment and culture, proper hiring process and getting great people in and constantly adapt to the team you grow.

Projects

• evisa-vn.com: tech-startup jack-of-all-trade founder & lessons learned
• goahead.sg: end-to-end solutions for Singapore property market - CTO & co-founder

Books

Photos

Talent Management

Communication Skills

Conflict Management

Videos

• How to Start a Startup - Y Combinator: The Vault
• The single biggest reason why start-ups succeed | Bill Gross
• Engineering Management: Interviews & Hiring ft. Google Engineering Director
• Brian Chesky’s new playbook

The role of a leader is to see potential in people that they may not even see themselves and when I tell somebody it's not good enough, either I'm saying you're not good enough, or I believe that you have more potential than you're showing me

Culture is what happens when you're not in the room and the brand is what people say when you're not in the room

I now try to say no to what I call fake work, which is things that feel like work but they don't actually move the ball down the field, and I really try to say yes to work that's very meaningful and people that are very meaningful to me

I hope years from now, 70% of what I said I still believe but if 100% of what I say, I still believe then I probably haven't learned very much

• The nature of product | Marty Cagan, Silicon Valley Product Group

On an empowered product team where you're trying to come up with a solution that solves the problem you've been assigned, that means we have to discover a solution that's 1. valuable 2. usable 3. feasible 4. viable. Now while the engineers definitely own feasible, and the designer definitely owns usable, valuable & viable which are two of the hardest things to do that's the product manager. That takes skill & knowledge. That's why we say in order to be a product manager on a real product team you've got to do your homework

There's 2 kinds of discovery: 1. discovering the problem to solve that you should focus on, and 2. discovering the solution that you're going to deliver that people would buy. People don't buy the problem they buy your solution. Obviously they don't buy it if it's not solving something they care about but, there are many products that are solving what they care about. The real question is do you solve it better than everybody else so that they buy you and that's where you need to take time. If you need to spend a little time on the problem fine but don't spend a lot of time, because you need to save as much time as possible to come up with the winning solution

Most of our time needs to be on solution and that's prototyping, that's testing with users, testing with customers, testing with stakeholders, testing with our developers, we're testing constantly. We're not just trying to find out you know if they like it. In fact, it's just the opposite. It's weird when we're doing user research, we're finding all the reasons they don't like it. In fact, that's an Elon Musk quote is when you do user research you should be focused on finding all the reasons they won't use your product

• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)

At the core design is is simply intention. You're bringing intentionality to the decisions that you make, and thinking about who is this thing for. If you're designing a door knob, does the door knob speak to whether or not I'm going to push or pull or turn, is it comfortable in the hand, is it easy to manufacture, is it easy to put on and remove. These are some of the intentional decisions one could make whether or author, a designer, an engineer, the product person, any function can put that intentionality, who is impacted by this, who is using this. That literally could be anything from designing a door knob to designing your org structure, to designing your strategy. Obviously great design is also creative and it also is demonstrated with great taste, design expertise with people that have these creative skills and and these great taste is an incredible important thing to bring into the organization. But I think day one everybody can bring more care and intentionality and I think that will result in better outcomes internally and externally in the long run.

• The ultimate guide to product-led sales | Elena Verna

Product-led growth is all about product's ability to self-serve activate, self-serve engage, and convert that usage to a monetization opportunity. So you bring people, you get them to an aha moment into the habit loops, and then you able to extract value back out of them.

Extraction of the value can be direct where you actually capturing revenue from them, or it can be indirect where they're participating in your growth model via virality or user generated content and bring additional business through the doors. There is self-serve monetization. So I'm using product self-serve, I go to the pricing page, I find the plan that best suits me on features that I want to unlock, or usage that I want to unlock, and I buy it. However that's not the only way to monetize that usage. You can monetize that usage with sales, too. Why? Self-serve monetization has a cap of about 10 thousand dollars that's just how much we're able to process on the credit cards before they start getting flagged and declined by the banks. So much we as a consumers and prosumers are even willing to put on our credit card, because not all credit cards have limits of over 10 20 30 40 thousand. So self-serve monetization is very much a prosumer use case where an individual is trying to solve the problem on their own.

Product-led sales converts the usage that you've generated via self-serve into a sales opportunity, and it attaches a salesperson to close a much larger contract, which can be 15 20 a 100 thousand dollars, in order to bring an enterprise level solution to a company that has already been using it in the self-serve manner. Product-led sales assumes that there is a migration from an individual use case that you acquired an end user, with and an escalation into an enterprise level solution that solves enterprise level problems.

Self-serve monetization is very much an individual use case, versus product-led sales is turning that individual use case and self-serve usage into a sales pipeline with enterprise level value.

In traditional sales world, marketing creates pipeline for sales, sales sells product, product engages with the paid user to drive retention. In the product-led sales, product acquires and activates a customer, and product creates pipeline for sales. So relationship is not that there is a go to market org with marketing and sales, and product just kind of throws features across the fence for them to sell. The collaboration here is between product and sales. What that means is the product has to take on accountability over pipeline. The worst thing that you can do is to say: "I'm going to do product-led growth or I'm going to do product-led sales, and I'm gonna do it in marketing". Recipe for disaster. You will be failure mode within 6 months, because product has to take accountability over selling of the product itself. And that is not to be taken lightly, because so many product teams are deeply deeply uncomfortable with owning monetization targets.

Every product should have goals on keeping healthy engaged user base. They should definitely have goals in terms of, maybe feature utilization, or customer satisfaction. But what I'm saying is to have also some sort of monetization goals. What that is for each company I think differs, depending on their level of comfort and their love and how close they are to revenue capture mechanism.

If you have a freemium product, I guarantee you 75% of your customers in freemium product are not aware of what you're selling. So only focusing on monetization awareness can give you incredible output on driving monetization, and it's really its products ability to communicate via feature walls, via usage walls, via trials, or what the value of the paid offering is. I've seen I've heard stories from Slack, of just showing message limits messaging, and how big of an improvement on conversion rate it had. I've had it firsthand at Survey Monkey, where just adding consistent UI across all of the paid triggers that were that Amazon gold color, and making sure that each user has been able to see at least 3 of them. There's a rule of 3 that goes into advertising, that we need to see things 3 times in order to remember them. That drove monetization awareness and conversion rate up, but that's basically consumes 80% of your work. The second one is just conversion rate optimization, so your pricing page optimization, your checkout page optimization, your currencies that you offer, the payment methods that you offer, to make sure that there is as low friction as possible in order to actually pay. Then the last one is is what you're selling do people want to buy. This is where you actually go after monetization model change, which features are in each plan, what are the price points in each plan, how does the upgrade path look like, do you have add-on strategy, do you have just pay to paid monetization plan strategy.

Awareness of monetization. Two ways. One qualitatively. I just run surveys against people say "do you know what we're selling?" It's shocking how many just have no idea what's in our paid plans. Or I just track pricing page views per activated account. So how many of the activated accounts landed on the pricing page at least once, because that's at least a level of exposure that they hit some sort of trigger that pulled them to explore pricing page. One of the things that I just want to give a hint to anybody who's listening from a sales top-down companies, one issue you might have is that when your product is developing functionality especially, paid functionality, they just design review it and ship it for paid plans only. So if I'm in the free plan or in the lower tier plan, I don't even see it I don't even know that existence, because it doesn't exist in the app because it was never designed for me to even see it. So just doing one small change of pushing your design reviews, to review functionality from every single state of the customer, free state, lower paid state, and target state. that this functionality is actually unlocked, can do all of the difference in the world. Because then you'll actually understand how that functionality is being exposed to a free user.

Pitfalls:

1. Don't treat product-led sales as a traditional top-down sales process. Every single user does not equal an opportunity for you to co-chase after. You need to understand the right triggers and usage. They can help you automate qualification process, so it's almost automating some of the SDR efforts to say when is the right time for my sales for my human that I'm paying a lot of money to intervene into this account and add value. Because sales interaction has to add value to user journey, not be disruptive, or create additional friction.

2. Hold your product accountable. This cannot be just executed through marketing and sales. Product has to have a seat at the table, and product and sales relationship has to be one of the closest ones in this motion. And that's really hard to change, especially in the traditional top down sales company where marketing and sales have closer relationship. So try to create new rituals, try to create the new ways of communication between the teams for them to be aligned behind the same goals number.

3. Don't leave marketing out of the equation. Majority of your usage will not have a buyer in it. You will need marketing your enterprise marketing, your account based marketing, to go and find and hunt that buyer, and to bring them and connect them with usage. So lean on your marketing team, just because you're doing product-led growth and product-led sales does not mean you don't need marketing. Strong product marketer can do wonders, in helping you with messaging, with outreach and sales enablement materials.

4. Don't wait on data and efficacy too long. You might be using your intuition at the beginning very well, but start thinking about how you will need to scale your data issues. because product-led sales is all about leveraging usage for pipeline creation. So you need to be able to measure that usage, understand that usage, track it and evolve it.

Podcasts

• Tech Lead Journal

Posts

• How To Scale a Development Team
• The CTO Journey at a Small Startup
• Scaling Slack during explosive growth
• The Infrastructure Behind Twitter: Scale
• Evolution of The Twitter Stack
• ‘Be hard on yourself’ and eight other lessons for bootstrapping a startup
• The 4 Growth Frameworks You Need to Build a $100M Product
• Better Engineering Leader: Wrapping Up the Series

Quotes

Start with the customer experience and work backwards to the technology - Steve Jobs

Customers don't form their opinions on quality from marketing, they don't form their opinions on quality from who won the Deming award or who won the Baldrige award, they form their opinions on quality from their own experience with the products or the services - Steve Jobs

In some cases when the music stops there'll be some people that don't have a chair - Steve Jobs

You know who the best managers are? They’re the great individual contributors, who never ever want to be a manager, but decide they have to be a manager because no one else is going to be able to do as good a job as them - Steve Jobs

Great people when they have different opinions, they usually can convince each other that one of them is right, or pick one that's better than all of them within a very short period of time - Steve Jobs

If you work with people that aren't as good as you then you know you become a country of midgets. If you work with people that are better than you then you really grow - Steve Jobs

If you get the right strategy, if you have the right people, and if you have the right culture at your company, you'll do the right products, you'll do the right marketing, you'll do the right things logistically in a manufacturing and distribution. And if you do all those things right the bottom line will follow - Steve Jobs

You can't connect the dots looking forward, you can only connect them looking backwards. So you have to trust that the dots will somehow connect in the future. You have to trust in something, your gut, destiny, life, karma, whatever. Believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well worn path, and that will make all the difference - Steve Jobs, Connecting the Dots

Sometimes life's gonna hits you in the head with a brick. Don't lose faith. I'm convinced that the only thing that kept me going was that I loved what I did. You've got to find what you love. And that is as true for work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied, is to do what you believe is great work. And the only way to do great work, is to love what you do. If you haven't found it yet, keep looking and don't settle. As with all matters of the heart, you'll know when you find it. And like any great relationship, it just gets better and better as the years roll on - Steve Jobs, Love and Loss

Your time is limited, so don't waste it living someone else's life. Don't be trapped by dogma, which is living with the results of other people's thinking. Don't let the noise of the others' opinions drown out your own inner voice. And most important, have the courage tto follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary - Steve Jobs, Death

Productivity means the ability to use man and machines in such a cooperative way that you produce more products per man-hour of a superior quality than any other person can do, any group of person can do. That means cooperation not antagonism - Lee Kuan Yew, 1980

To the young and to the not so old, I say, look at that horizon, follow that rainbow, go ride it - Lee Kuan Yew, 1996

When the student is ready the teacher will appear. When the student is truly ready, the teacher will disappear - Lao Tzu

Quality is not an act, it is a habit - Aristotle

If you can dream it, you can do it - Walt Disney

If people aren't laughing at your dreams, your dreams aren't big enough - Robin S. Sharma

Strive for continuous improvement, instead of perfection - Kim Collins

It does not matter how slowly you go as long as you do not stop - Confucius

It always seems impossible until it’s done - Nelson Mandela

In this life, you don't have to prove nothin' to nobody but yourself - Rudy

If you can't explain it simply, you dont understand it well enough - Albert Einstein

Train people well enough so they can leave, treat them well enough so they don't want to – Sir Richard Branson

Everyone wants to live on top of the mountain, but all the happiness and growth occurs while you're climbing it - Andy Rooney

If you're going through hell, keep going - Winston Churchill

Life moves pretty fast. If you don't stop and look around once in a while, you could miss it - Ferris Bueller

Don’t ever get too comfortable, you can be replaced - Unknown

Keep your friends close; keep your enemies closer - Sun Tzu

When it feels scary to jump, that is exactly when you jump, otherwise you end up staying in the same place your whole life, and that I can't do - Abel Morales

If you’re good at something, never do it for free - The Joker

With great power comes great responsibility - Stan Lee

Some birds are not meant to be caged, that's all. Their feathers are too bright - Stephen King

My mama always said, life is like a box of chocolates. You never know what you're gonna get - Forest Gump

Yesterday is history, tomorrow is a mystery, but today is a gift. That is why it is called the present - Kung-Fu Panda

Don’t ever let somebody tell you… You can’t do something. Not even me. Alright? You got a dream… You gotta protect it. People can’t do something’ themselves, they wanna tell you you can’t do it. If you want something’, go get it. Period - The Pursuit of Happiness

Well Mr. President, I’m helping put a man on the moon - Mr Janitor