How Chess Helps Us to Make Tech Decisions.

So for those of you who don’t know, some of us in Mäd are chess enthusiasts. We play chess in our coffee break, we sneak it in during lunch, and we play after work over here, when we finish off at whatever time. It’s always a good way to end your day. (Even though it’s not so good when you lose?)

The point of this article is not to get you into chess. There are certain habits in chess that encourage you to be better, in whatever industry you are in. It won’t answer some questions you might have about whatever issue you might have, but it might give you some questions to take away and ask for yourself.

Who plays chess

Recently, Bill Gates had an exhibition with the world’s best chess player, Dr. Drunkenstein (better known as Magnus Carlsen). Who do you think wins?


Magnus Carlsen beat Bill Gates in 9 moves. It took him under a minute and a half. BUT, Magnus Carlsen is worth $8 million, Bill Gates is worth $150 billion. So really, who’s more successful?

And in all honesty, there is a danger of measuring success in dollar values.

Peter Thiel


This guy started PayPal, and now he runs an investment group, Clarium Capital. He was also Facebook’s first external investor. So clearly, he knows his moves.

Now he’s pretty well-known for his lectures in Stanford where he often talks about chess, and using that as examples of how to help businesses. I’ve borrowed plenty of his ideas for this article.

And these guys.


George Soros, Carl Icahn, Pierre Omidyar.

It goes both ways. Not all chess players end up in Wall Street, running successful startups. The smart ones give up chess instead of becoming grandmasters, and make a lot of money in Wall Street. Good for them.

Benefits of Chess for Your Business

You’re gonna be damn smart.

Actually, that’s not entirely true. They’ve done a research on the benefits of chess on young children, and they couldn’t find a correlation between chess and intelligence.

But, they did another research on adults, and found that there is a strong correlation between cognitive abilities and chess. Chess does help with cognitive abilities, processing speed, short-term memory and comprehension.

So that’s the obvious one out of the way.

Being Pragmatic

Everything we do in Mäd, we have to do step by step. There are rules in chess that are not strictly laws, but they are rules for a reason. Your rook shouldn’t be out too early, they’re the best when some of the verticals are free. You should try to control the centre. Don’t block your own pieces.

Know your sequences: Chess has three acts, just like a drama: the opening, the middle and the endgame.

Every move that your user makes matters.

The opening: what comes after the splash screen? Is it going to be your brand, your value proposition? That matters. Do you need a login screen before you convert your user?

Customers always think step by step, so at any given time you need to be at least two or three moves ahead of them. UI/UX has best practices. Same with chess. Openings are known for good reasons. English, Sicilian, King’s Pawn, many players follow these openings because they are proven.

Just as in chess we train ourselves to think sequentially. Step by step.

Compared to chess, actually building a website, or mobile app is far more complex. There are more variables, there are more players. There are infinite amount of steps, but the board is bigger. Much bigger.

Same thing with what we do here. What features do we need to develop first? Do we need a login? Why? Should Create Order come after Order History? What if there’s no connection? Poke every hole. Every move matters.

The screen below is a quick example of a simple feature. Order History. Sure, you need to order, but what happens if the order is rejected? What happens if the order is cancelled. Then what happens next when the delivery is complete?


But look at it in a higher level:

How are you going to convert your users? What’s your target? There’s another chess grandmaster, Capablanca, who said that before you study anything else, you should study the endgame.

This quote is apt.

“To succeed you must study the endgame before anything else." ~Capablanca

Always start with the endgame. What are your business objectives? What does success look like to you? This is the one question that we always ask our clients and prospects.

And quite a few struggle with this. Without the endgame in mind, the openings don’t even matter.

In chess, time is a resource, especially in blitz games. That is the same in any business. We can see this in our scrum teams. Every single task is broken down in hours. We plan what we need to develop two weeks in advance, that’s the sprint planning. We know the total number of hours available to us, and then we work backwards.

So this, brings us to our next point.

Value and Opportunity Cost

Each chess piece has a different value. The pawn is valued at one point, the knight and bishop at 3 points, the queen at 10. The biggest irony is that the King has no value, because he is the last piece: you cannot trade your king for any piece. But, in the end, the value is very subjective.

It is very subjective because we don’t know if the players with more points will win the game. More often than not, they do, but sometimes we don’t know. The color of the bishop in the game matters. The knight and the bishop are both worth three points each, but depending on the type of game you play, they may be worth more. If you are playing with a lot of open spaces, then you’ll be stupid to sacrifice your bishop, because they cover more space. If the game is congested, more often than not your knight will be super useful. So in this situation, it’ll be silly to sacrifice your knight.

We had a talk last time, for Mäd Monday 2, Mike Ivanov from Pay&Go talked about how to prioritize which features to develop. Whether the feature is going to be profitable, and whether the team has the capability to create the feature in the given amount of time.

Every task has its value. Every task has its priority. So which comes first? How do you define which should come first? And this, absolutely depends on you.

Rule of Economics

There are always unlimited demands, unlimited things to try, unlimited wants, features, but resources are always going to be limited. There are only so many hours in the day, and so much you can focus your attention on. So prioritization matters, but how do you define that?

Every organization should have a way of measuring the value of each task. Is it going to be an important feature that everybody uses? How do you decide on that?

A typical example is business value versus complexity quadrant. Even this one is problematic. How do you define business value? Is it going to depend on the size of your users? The expected revenue from users? Do you even know the size of the population? How do you measure complexity? Is it an estimation by development time?

This should be going regularly through your minds, and eventually you will be able to gauge the value and complexity intuitively, because the longer you spend on your product, the better you know your users, your customers, the better you know them.

There are other ways where you can measure value. Last time Mike talked about weighted scoring, so those involved in the project give a value between 1-10 on the complexity and the value. This is still quite subjective, in some respects, most of them are, but at least with the law of averages, and the wisdom of crowds, you can have a more objective result.

Value is always tricky, whether you’re paying for a ming vase, stocks, developing a feature. But if you are unsure, at least for us, we follow a principle: always go back to your user.

But, whatever you do, always have a plan.


So Peter Thiel again.

“A good intermediate lesson in chess is that even a bad plan is better than no plan at all. Having no plan is chaotic. And yet people default to no plan."

Making a plan is difficult. Yes. But like he said, having some form of a plan is better than having no plan at all.

This, in some ways, is very similar to thinking pragmatically, but at the same time, there are further questions to ask in the bigger picture.

What are the risks? How fast can you pivot?

In chess, you might be planning an attack on the king side, with a bishop, but if your opponent sees that coming, then you need to change the plan altogether. Either you apply more pressure, with more resources, or you change the direction completely. You attack from the other side of the board, use different pieces.

Planning a mobile app end to end is also more complex than planning an attack in chess. What comes first?

Once we’ve signed the proposal, how do we lay everything out? Who’s responsible and accountable for each step of the process? We make no apology for sending extremely long proposals, because we go through the minute details.

Other Lessons

Here are other things I learned from playing chess.

*Analyze your competitors
*Work under pressure
*Teaches you to be humble in your win
*Teaches you to be humble in your losses

Thinking about Chess the wrong way.

People as Chess Pieces


There is a danger to using chess as business analogy. One analogy that I don’t really want to use is that of chess as a narrative for an organization. Even though it is based on that, I can’t sacrifice anyone in the team.

It’s pretty silly looking at people as chess pieces. Everybody plays a bloody important role. I can’t say that the board members is the King, or the CEO as a queen, it’s just not such a good analogy for the modern times. I do find substituting people as chess pieces to be limiting, and very demeaning.

So yes, there are dangers of thinking too far in advance. We’re running businesses here, we don’t have the luxury of time. It’s always chasing you, trying to bite you right in the bum. Every business is a lightning chess game. Your information is limited by the time available to you, but in all cases, we have to always minimize errors.

And I think the biggest difference is that chess, it’s an individual game. Business, technology, you can’t do alone. You need a team for that. And a bloody good one too.

Kit Teguh

Kit Teguh

Digital Strategy @ Mäd. Spending more than half his life in Asia, Kit brings the local knowledge to the team. Believing that there is always much to learn, he instills a learning attitude in Mäd.

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How Chess Helps Us to Make Tech Decisions.
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