How to decide who to work with

Think of the last time you were introducing yourself. You probably started with, went into detail about, and ended summarizing what you do now, or how you did what you did previously.

Take a look at job postings. Most will go into detail about what the job is, how critical it is to the business, what the roles and responsibilities are and what the title is. The same thing happens in job interviews — you are encouraged to describe what you did in your previous roles.

I started my career almost 15 years ago this month. If there is one big takeaway from all my professional work experience, it’s that who you work with matters way more than what you do and how you do it.

Almost everyday I need to make a decision on who I want to work with — cofounders, customers, employees, partners, investors, interns, mentors, advisors….it’s a long list of people who are so critical that making the wrong choice on one or more of these is guaranteed to ruin my work and the value I create in this world.

So to get clarity on this, I created a simple framework for deciding who I want to work with. Let’s call it the 2x2 Ability/Intention Grid.

The 2x2 Ability/Intention Grid

Ability is simply the aggregate of the skills, the drive, the passion, the desire to do good work.

Intention is a combination of a person’s motives, beliefs, and assessment of what is right v/s wrong.

Good Abilities & Right Intentions

Image: Courtesy of TheAtlantic.com

This is where magic happens. This is where dictatorships are toppled, social change happens and innovation thrives. When you find a person, or group of people who have the skills to create amazing things, who are smart, and driven, and have a set of motives that align with yours and their assessment of right versus wrong resonates with yours, whatever it is you are working on will thrive and create value.

You will not come across many people who will fall into this quadrant. But when you do, figure out how to work together. If it’s a customer, figure out how to align your incentives and create something beautiful. If it’s an interview candidate, show her how together you will create something valuable.

Weak Abilities & Right Intentions

Oh Charles, you mean well.

The majority of people you will come across usually belong in this quadrant. These are people who might not have all the skills to be great at their work, but they align with you on what is right versus wrong and share common beliefs with you.

This is the job candidate who doesn’t have years of fullstack development for a SaaS application, but understands the importance of not building technical debt. It’s the cofounder who knows she hasn’t done sales before, but shares your vision on what your idea can be and understands that you both need to roll up your sleeves to get things done.

When you come across someone from this group, you both can amplify the abilities by working together, but only if the intentions are aligned. When things don’t work out, at least the damage will be limited and scoped. If you hired someone and her skills never got to the level needed to execute, your startup won’t die.

Good Abilities & Wrong Intentions

Zero-sum games: If you are good, but have the wrong intentions, you will figure out a way to capture as much of the pie rather than spend a moment figuring out how to grow it for everyone.

In this group, it’s people who have good skills, but wrong intentions. Very little, if any value is created around them, and in fact they end up destroying more value than creating it. But they come out ahead. It’s similar to not really growing the pie, but getting as much of it as you can, for yourself. Greed is usually the driving factor behind the person’s intention.

Pro-tip: If you are in this category of people, be really good with your abilities. i.e if you know you are an a$$hole, be a really good a$$hole. Don’t suck at that. You won’t be liked or loved by people around you, and you won’t create sustainable value in the world, but you will do great. Because if you are not good at what you do, you will end up causing good and important things to die (Bad Abilities & Wrong Intentions)

Weak Abilities & Wrong Intentions

This is why good things die.

These type of people hurt the world the most. Great ideas die, companies get shutdown, employees get laid off, products get killed, and customers are shortchanged.

Unfortunately the second largest majority of people fall in this quadrant. Figure out how to recognize people from this group and get as far away as you can. That investor willing to fund your right now, but has no idea how to help your startup will eventually kill your company. That slow-moving partner who is willing to sign a contract now will eventually be the source of all the negativity and drag down your business.


I have worked with people from all four groups, and I have made a conscious decision to recognize who I am working with way before we talk about the what and the how. Your time, your work, and your life is precious — don’t waste it on working with the wrong people.