As a leader, I shouldn’t put it all my on my shoulders

I won’t be able to share every burden, but share very burden that I can. Get the maximum number of brains on the problems even if the problems represent existential threats.

Startup is not Checkers, startup is a Chess!

Tech business tend to be extremely complex. The underlying tech moves, the competition moves, the market moves, the people move.

Play long enough and I might get lucky.

In tech game, tomorrow looks nothing like today. If I survive long enough to see tomorrow, it may bring the answer that seems so impossible today.

Don’t take it personally

Every CEO makes thousands of mistakes. Evaluating myself and giving myself an F doesn’t help.

Remember that this is what separate women from girls.

If I want to be great, this is the challenge. If I don’t want to be great, I should never have started a company.

Nobody take bad news harder than you do.

Don’t think I would be best to handle bad news. It’s not my job only to worry about the company’s problems. Give the problem to people who could not only fix, but would also be personally excited and motivated to.

Make my Company Problems Transparent.

Following are reasons:


If they trust me completely, I require no explanation or communication of my actions whatsoever because they know whatever I’m doing is in their best interests. But, if they don’t trust me at all, then no amount of talking, explaining or reasoning will have any effect on them.

As company grows, communication becomes biggest challenge. If employees fundamentally trust CEO, then communication will be vastly more efficient than if they don’t. Telling things as there is a critical part of building this trust.

More brains working on solution, the better

It’s a total waste to have lots of big brains but not to let them work on my biggest problems.

Bad news travel fast. Good news travel slow.

Healthy company clutlre encourages people to share bad news, so people can freely and openly solve them. A company that covers up frustrates everyone involved.

The famous Don’t bring me a problem without bringing me a solution stops information from flowing freely.

If an engineer identifies a serious flaw in the marketing, would I really want him to bury that info?

Why we hire wrong leaders

We did a poor job defining the position in first place.

Hiring based on abstract notion leads to executives not bringing the key, necessary qualities to the table.

We hired for lack of weakness rather than for strengths.

If I don’t have world-class strengths where I need them, I won’t be a world-class company.

We hire for scale too soon.

If I hire someone who will be great in 1 year but will be poor for 1 year, people will reject her before she even gets a chance to show her stuff.

We hired for generic position.

There’s no such thing as great head of sales. There’s only a great head of sales for my company for next 1 – 2 years.

The recruit has wrong kind of ambition.

It doesn’t matter how outstanding the recruit is, if her goals don’t align with that of my company, I shall reject her.

We failed to integrate the executive.

Review my improve my integration pan after I fire an executive.

Firing an Executive

Be clear on the reasons

No need to sugarcoat it. I owe it to them to be clear about what I think happened.

Use decisive language

This is not performance review. Use words like I have decided rather than I think. Don’t’ leave the discussion open-ended.

Have the severance package approved and ready

Be ready to provide specific details of the severance package.

Demoting a Loyal Friend

I should not take the sting out of it, but be honest, clear and effective. My friend may not appreciate that in the moment, but he will appreciate it over time.

What is not enough, People need Why.

I have to be clear about why I wanted them to do the way we need.

Why do we do what we do?

Consider a Training Program for TBH

Withhold new employee requisitions from managers until they’ve developed a training program for TBH.

Hiring from Friends / Partners

IF I would be shocked and horrified if company X hired several of my employees, then I should not hire any of theirs.

Mismatches of hiring Big Executives

Rhythm mismatch

Big executives has been conditioned to wait for emails to come in, wait for phone to ring, and wait for meetings to get scheduled. People will then become suspicious What does this guy do all day? Why did he get so many options

Skillset mismatch

Ruunning large organization requires very different skills than creating an organization.

When I run large orgnaizations, I tend to become very good at tasks such as complex decision-making, prioritization, organizational design, process improvement and organizational communication.

When creating an organization, there is no organization to design, no process to improve and communication. But I have to be very adept at running a high-quality hiring process, terrific domain expertise and how to create process from scratch and be extremely creative about initiating new direction and tasks.

Screening for mismatches

Q: What will you do in your first month on the job?

Look for people who come in with more initiatves than I think is possible. This is a good sign.

Q: How will your new job differ from your current job?

Beware of candidates who tink that too much of their expertise is immediately transferable.

Q: Why do you want to join a small company?

A desire to do more creating is the right reason.

Integrating the Candidate

Force them to create

Give them monthly, weekly, and even daily objectives to make sure they produce immediately.

Make sure that they get it

If I don’t have any questions from them, it’s a red flag. In 30 days, if I don’t feel they’re coming up to speed, consider firing them.

Put them in the group

Give them a list of people they need to know and learn from. Require a report from them on what they learned form each person.

Hiring Great HR

World-class poccess design skills

Much like head of QA, head of HR must be a masterful process designer.

True Diplomat

HR must help them improve rather than police them. If HR leader hoards knowledge, makes power plays, or plays politics, he will be useless.

Industry Knowledge

HR must be deeply networked in the industry and stay abreast of compensation benefits, best recruiting practices etc.

Intellectual heft to be CEO’s trusted adviser

He must possess integrity and credibility so his thinking and judgement can be trusted by CEO.

Understanding things unspoken

Superperceptive people can tell company is slipping when nobody says anything about it.

How Big should the Titles be?

There are two schools of thought; one represented by Marc Andressen and other by Mark Zuckeberg

People ask for many things, salary, bonus, stock options … Of those title is by far the cheapest so it makes sense to give highest titles possible.


Deploy titles that are significantly lower than industry standard, but guarantees to relevel as they’re permanent. In this way, you avoid accidentally giving new employees higher titles and positions than better-performing existing employees.


It’s true Facebook misses out on new hires due to its low titles. But they also miss out on people they don’t want.

Make 1:1 Great

Being good at 1:1 meeting is understanding that it’s employee’s meeting rather than manager’s.

Follow the employee’s agenda. Here’re are some key questions:

  • If we could improve in any way how would we do it?
  • What’s the number one problem with our organization? Why?
  • What’s not fun about working here?
  • Who’s really kicking ass in the company? Whom do you admire?
  • If you were me, what changes would you make?
  • What don’t you like about the product?
  • What’s the biggest opportunity we’re missing out on?
  • What are we not doing what we should be doing?
  • Are you happy working here?

Nuts and Bolts of Organizational Design

Figure out what needs to be communicated and who needs to be in loop.

Start by listing the most important knowledge and who needs to have it. E.g. Knowledge of the product architecture must be understood by engineering, QA, product management, marketing and sales.

Figure out what needs to be decided.

Consider types of decisions that must get made on frequent basis. Put maximum number of decisions under the domain of a designated manager.

Prioritize the most important communication and decision paths.

Decide who’s going to run each group.

Don’t put individual ambitions of people at the top of organizations.

Identify the path that I did not optimize.

Just because it’s not a priority doesn’t mean it’s unimportant. If I ignore them entirely, it will surely come back to bite me.

Nobody comes out of the womb knowing how to mange a thousand people.

Evaluating people against future needs based one theoretical view of how they will perform is counterproductive. Everybody learns at some point. Was it obvious that Bill Gates would learn how to scale when he was a Harvard dropout?

If I already make a judgement that someone is incapable of doing something, it doesn’t make sense to teach them anymore. In other words, hire for attitude and train for skill.

There’s only a great executive for a specific company at a specific point in time.

Zuckerberg is a phenomenal CEO for Facebook, but he would not be a good CEO for Oracle. Make judgement on a relative rather than an absolute scale.

Asking myself if an executive is great can be extremely difficult to answer. A better question would be for this company, at exact point in time, does there exist an executive who I can hire who will be better? If my competitor hire him, how will that impact our ability to win?

Focus on what I need to get right.

Stop worrying about all the things I did wrong or might do wrong. This is the most important thing Ben learned as an entrepreneur.

Techniques to Calm The Nerves

Make some friends and talk to them.

It’s nearly impossible to get high-quality advice on the tough decisions I make But it’s extremely useful from a psychological perspective to talk to people who have been through similar challenging situations.

Get out of my head and onto paper.

Wiriting a document separated me from my own psychology and enabled to make the decision swiftly.

Focus on the road not the wall.

If I focus on the wall, I’ll drive right into it. If I focus on the road, I will follow the road.

Fine Line between Fear and Courage

Everytime I make the hard, correct decision I become a bit more courageous and everytime I make the easy wrong decision I become a bit more cowardly.

Two core skills for running a  great organization

  1. Knowing what to do
  2. Getting the company to do what I know

Measuring the quality of  a leader

The quanity, quality and diversity of people who want to follow her.

Attributes that make people want to follow a leader

  1. Ability to articulate the vision (Steve Job’s attribute)
  2. Right kind of ambition (Bill Campbell’s attribute)
  3. Ability to achieve the vision (Andy Grove’s attribute)

Giving Effective Feedbacks

To become elite at giving feedbacks, I must do better than negativity sandwich:

  1. Be authentic
  2. Come from the right place (my right intentions for them to succeed)
  3. Don’t get personal (criticize behaviors not the person)
  4. Don’t embarrass in front of peers.
  5. Recognize feedback isn’t one-size-fits-all. Some people have particularly thick skin and thick skulls while others are extremely sensitive to feedback.
  6. Be direct. But not mean.
  7. Encourage a dialogue. Not a monologue.

Negativity Sandwich

Works well with junior employees. But it has the following chanllenges:

  1. Tend to be over formal.
  2. Tend to lack authenticity. Oh boy she’s complimenting me again. I know what’s coming next shit!
  3. Senior executives recognize it immediately and it will have an instant negative effect.

Should I sell my company?

A good basic rule of thumb is do not sell if:

  1. I’m very early on in a very large market
  2. I have a good chance of being no.1 in that market

If one of the above is violated, consider selling.

When people ask Are you Selling the company?

If I say at the right price, employee will wonder what that price is and may even ask. If the company reaches that price, he will assume I will sell the company.

If I say the company is not for sale, and later I sell the company, the employee may feel betrayed. More importantly, I will feel like I’m betraying the employee and that in turn will influence my decisions.

So say, If the company achieves product-market fit in a very large market and has an excellent chance to be number one then the company will likely remain independent. If not, it will likely be sold.

Kyaw Wai Yan Tun

Hi, I'm Wai Yan. I love designing visuals and writing insightful articles online. I see it as my way of making the world a more beautiful and insightful place.