Why is it tough to transition to a business leader?

Yogesh Upadhyaya
9 min readMay 26, 2024


What would you find tougher — To solve the Rubik’s cube or to successfully design, manufacture and sell a product like the cube? The difference between the two challenges is central to the topic of the post: Why do so many of us find it tough when we become business leaders? There are many reasons for this but I believe that one of the main ones is that business schools train us to solve puzzles, whereas as business leaders we have to tackle ill defined, open-ended mysteries. Let us begin with understanding what I mean by puzzles and mysteries.

Image by Francis Ray from Pixabay

I first came across this distinction between puzzles and mysteries in the book radical uncertainty by John Kay and Mervyn King. The authors say,

“A puzzle has well defined rules and a single solution, and we know when we have reached that solution….Puzzles can be solved; they have answers.”


“Mysteries offer no such clarity of definition, and no objectively correct solution: they are imbued with vagueness and indeterminacy”.

Rubik’s cube is a brilliant example to understand this difference. (I first read it in a post here). The cube has an absurdly high possible number of moves but can be solved in a maximum of twenty moves. The world record time for solving the puzzle is slightly more than 3 seconds! Rubik’s cube fits the definition of a puzzle. Contrast this with the business challenges of making and selling the product profitably. In the author’s words

“There are huge numbers of unknowns — something like this six-sided mechanical puzzle had never previously been built. There were virtually infinite amounts of material choices, design options for making it work, appropriate toy regulations, packaging and marketing requirements, manufacturing options, marketing and distribution strategies, etc. There was no one right answer to any of these questions, and it is also quite possible that (at the outset) there will not be any solution that solves all constraints”

Overcoming these challenges took six years. More tellingly, none of the follow-on products launched by the company had anywhere close to the success of the original Rubik’s cube. Have you even heard of the flat ‘Rubik’s Magic’ or the spherical ‘Rubik’s 360?’ Whether a puzzle would be a successful product is a mystery.

As people transition to becoming business leaders, their challenges become more mysteries and less puzzles. Problem definition becomes difficult and all definitions are contested. All possible outcomes are not known and there is no guarantee that a successful outcome will be achieved. The world of a business leader is not Puzzleland but Mysterystan.

Most of our education, including business education, focuses on making students better at solving puzzles. Why don’t the business schools equip students with skills that would help them tackle ill defined and open ended problems? To answer this, we have to understand some of the challenges faced by business schools.

The challenge for a business school in India starts with the admission process. The Combined Admission Test (CAT) is a set of more than sixty questions. All the questions are puzzles. They have to be if the entrance test is to be objective. A mystery kind of question in the test would mean that thousands of answers would have to be judged by hundreds of different invigilators. Even if we keep aside the very real problem of corruption, there is no way you can expect different examiners to judge students by the same standards. Puzzles with definite answers are a solution to this problem as they are objective. This need for objective evaluation carries through in the MBA course too.

A professor would struggle to explain to her students why she has given the grade she has if she judges students on mysteries rather than puzzles. The problem is compounded because many students may not have good communication skills. I have seen student output from some of the best business schools and I would rather schedule a trip to a dentist than correct fifty such papers. If a professor sees a poorly written answer to a ‘mystery question’ is it because the student did not understand or is it because he could not communicate well? So business schools end up selecting good puzzle solvers and encouraging them in many of the courses taught.

The case study method of teaching (and evaluation) is supposed to introduce students to mysteries but it can often fall short of this aim because of many challenges. Let us understand some of them using an example.

The student is asked to advise the Chief Minister of Delhi on how to clean the Yamuna river that flows through the city. There is very little chance that the student would know that a big part of the challenge is that in non-monsoon months, more than 90% of water is taken away upstream for irrigation. Even if they became aware of it, they would not know that our policies encourage farmers to grow water thirsty crops and reducing irrigation outflow is not at all easy. Additionally, they may not know that the Delhi CM has no jurisdiction to tackle these issues. Additionally, even when the student comes to know that the Najafgarh drain is possibly the biggest source of pollutants into Yamuna, they may not appreciate that setting up a working Sewage Treatment Plant (STP) to clean the discharge may not have any political benefits for the CM. This is because the water quality may not visibly improve because there are so many other sources of pollution. The challenge is that this is a complex problem with a lot of interconnections and the students need to know many facts before they can start making intelligent suggestions. They need to understand the domain.

Of course, the Professor could put all these facts in the case study itself. But then, the Professor has converted the mystery into a puzzle with the facts and their rank-ordering determined by the professor herself!

Could the students be asked to work on a project that makes them understand the domain? In theory, yes. But practically we have a fresh set of challenges.

First, the domain may not be easy to learn. Note, that we have barely scratched the surface in our previous paragraph on cleaning Yamuna. Secondly, the Professor herself may not understand the domain of the project selected by students. Then there is the well known student tendency of starting the work at the last minute. Most domains are complex and last minute work has no hope of even beginning to understand the problem. Without this understanding, the student is likely to mindlessly apply whatever technique is being taught in the class. Perhaps the biggest challenge however, is that many of the best students are puzzle solvers and hate uncertainty.

In my first month at one of the best management schools in India, a second year student approached me to administer a psychology test. A few days later I got the results. The only thing I remember so many decades later, is that I scored very highly on the trait ‘Allergy to Ambiguity’. The score was so high that it shook me.

Since then, I have lost a lot of respect for psychological tests. Especially those administered by college students to other college students. However, I believe that the test result showed me something important: I was not comfortable with ill defined problems with no one right solution. Perhaps I was born with this trait. Or perhaps years of being good at Math and the Sciences made me so. It does not matter. What matters is that in MBA schools across the country, we would have many people who are allergic to ambiguity. So allergic that, like I did then, they would deny that it exists. Why does this denial of ambiguity not impact their career prospects just out of business school? It is because many entry level jobs are mainly puzzle solving.

My beginning at the rating division of CRISIL — a credit rating company — was very smooth. There was a well defined procedure for credit rating of companies. The procedure was templatised in a “rating note.” The job of a rating analyst was to fill in the rating note. Financials of the company needed to be analyzed but there was an Excel template for it. The job was not very difficult for good puzzle solvers. Sure, there were judgment calls to be made. For example, about the industry structure and about management quality, but there were people with experience of doing hundreds of ratings who could temper the judgment calls. The benefit of these templates was that a smart graduate could learn to do the job fairly quickly.

We can see this templatisation in almost all entry level jobs in established companies. Perhaps it is nowhere more so than in coding. In the classical waterfall model of software development, business analysts would talk to the clients and gather requirements. Software programmers would write code based on these requirements. When it turned out that the code was nowhere near what the client wanted, they would promptly blame the business analyst. I am told that the situation has improved with the use of development methods like Agile. But, I suspect that in thousands of teams across the world, people are still bickering and one big reason is that programmers, especially the inexperienced ones, believe that just because they are solving puzzles, their team is too.

As an aside, people who have been in puzzle solving jobs like coding start believing that the whole world is a puzzle to be solved. This makes for extremely irritating conversation on politics and society but some of this kind of people have been responsible for a huge amount of the technological and economic progress of the last few centuries. Good puzzle solvers convert mysteries into puzzles and then solve them. Let us take an example. A few hundred years ago, sea going ships could be smashed by sudden sea storms. Nature behaved like an unpredictable vengeful God. Now good quality short term weather forecasts means that very strong storms can be safely avoided. At the same time improvement in the quality of ships means that they are much more resilient.

Working intelligently and assiduously in template jobs works very well for young professionals at least for a few years. Then they are put in positions where they are responsible for converting all the ill defined uncertainty around them into well defined jobs for their freshly delivered MBAs. If they are skillful and lucky, they quickly understand that they have left Puzzleland behind and are in Mysterystan. Many don’t.

A fresh graduate who becomes a startup founder does not have this grace of a few years. From day 1, he has to figure out the market he is in, what his offering is, how would he persuade people to buy and use it, how much would it cost to build it and finally would he be able to do it profitably. A complex mystery to be tackled if there was any. To simplify this mystery, some beginning entrepreneurs import product ideas and business models from abroad. In this they have the support of many investors. However, even with these hacks, the fresh graduates have to quickly switch from a puzzle solving to a mystery tackling mode. Those who succeed are incredibly talented, flexible in their thinking and very very lucky.

How can Professors in business school tackle this challenge of equipping students to tackle mysteries rather than solve puzzles? Perhaps, they can learn from Professor Richard Rumelt of University of California. In his book Good Strategy Bad Strategy, Professor Rumelt narrates an incident. A colleague attended his classes. After ten of these, the colleague commented that in all his classes, Richard was getting the students to ask the question ‘What is going on here?’ Tackling mysteries means spending a huge amount of time on this ‘diagnosis’.

Any ‘solution’ to a problem would not make sense if the diagnosis is faulty. Most student level diagnosis of complex situations is so bad that it is not even faulty. The professor could perhaps spend most of the project time ensuring that the diagnosis is not obviously flawed. This could be done by the professor asking the students to come up with a diagnosis early and then challenging it. The challenge could be repeated multiple times. But is there time in one course for such a project?

My friend Manish Agarawal, perhaps the best teacher of Systems Thinking in India, has a great idea that would tackle this challenge of time and many other challenges that we have discussed. He suggests that MBA courses should have a project running through the entirety of the second year. The project should have early and frequent challenges including from outside experts and internal faculty. The grading of the project should be mainly on how students respond to the question, “What is going on here?” rather than on any solutions that the students propose. The quality of responses to “What is going on here?” should be judged not by its correctness but rather by its internal coherence and by how many levels deep the students have gone.

Working on such a project would be a big advantage for the student. When the time comes for him to step out of Puzzleland into Mysterystan, he would perhaps find it just a little bit easier.

This article is part of the series — Tips for early / mid career analytical types.

“How to spot a bad expert” in this series has received a lot of attention.

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Yogesh Upadhyaya

Entrepreneur. Economist. Investor. Actor. Technophile. Policy wonk. Comedian. I love to explore places where these worlds intersect.