Dimitar Phillipov
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Why Project Managers Ask Stupid Questions

Why Project Managers Ask Stupid Questions

May 26, 2025Dimitar PhillipovHow To Cook a Parrot
project-management

How do you feel in situations where you're not the smartest person in the room?

Ashamed, nervous, and in a defensive position that verges on apathy.

You expose yourself for fear of exposing yourself.

You feel like something is wrong, but you're unsure about expressing it.

You join the conversation with something that might sound intelligent and you find yourself forced to defend your hollow thesis.

Or you swallow your grammar and go into a reactive mode of "we'll think about it later."

You don't want to relive the trauma that opened up in 5th grade when you raised your hand, said something nonsensical, and half the class laughed at you, while the teacher quickly switched her attention to her favorites, who were always "prepared."

And that's it - the "Study to succeed" or "The smartest one eats the pie" model has taken root in your innocent childish subconscious, only to become the hidden destroyer of your dreams and the gray cardinal that secretly brings mediocrity into your life.

Try to remember what you were taught as a child about curiosity - were you encouraged?; was that a good thing?; or was I supposed to keep quiet and not ask questions because I was annoying my mom?

Now you're grown up, have a family, and bear the burden of responsible decisions . Those who you simply can't drown out in a 15-minute 'session' of cheap dopamine - keep coming back and knocking on the door.

Your brain is burning out trying to create practical order in sectors of disinformation and chaos. You leave the conversation, open Google or ChatGPT, and search for answers to unasked questions, only to have new questions arise.

The critical analysis process has strained your mind and your brain has automatically registered a threat signal - you are looking for distraction.

It would be interesting if we could calculate the unrealized profit , the funds spent, and the time lost - derivatives of each unspoken question.

For a long time, I wondered why I ask more questions than others around me.

  • I went through a period of being proud of something I used to call "critical thinking".
  • through the contradiction "is it good to be different, does that make you a rebel , is it good to be a rebel...",
  • along with philosophical reflections on perfectionism ,
  • and finally the socio-emotional breakdown after labels like: “…you can’t talk to him, he doesn’t listen to anyone… ”.

It took me a lot of digging to find the right definitions for my subtle quirks, which challenged my personal sense of self-worth.

You may have been blessed like me - being encouraged to be curious as a child - I owe that to my grandmother , Milica Filipova. After 30 years, I am beginning to realize the profound value of her daily declarations to me that I was a "curious child" . If I have the opportunity to pay tribute to her in only one place, let it be this page!

Or maybe you were forced as a child to "bury" the discoverer, typical of every child's mind, because your parents needed a "minute of peace" after a slavish 9-to-5 workday.

As I have admitted to myself that I sometimes do with my children, the concept of homeschooling has become too high on my list of personal projects.

By the end of the article, you will understand the mental model that:

**- It will help you see the opportunities that you have so far frivolously written off.

  • It will become your new weapon to tackle the biggest challenges in your projects.**

To warm up - how far can we go if we start asking questions about your life?

Try not to look for answers through analogies and information you've already heard from somewhere, and after every spontaneous answer that comes to mind, ask yourself again - is this really true?

  • Why shouldn't I get a promotion, even though I don't see any logical reason for it to happen?
  • How do you get promoted? - after hard work?; after being included at the right time?; or by a good combination of circumstances?; What if I have low (or clouded) self-esteem, and I don't realize how much I've proven myself and now a door opens for me? Could it be that I've been doing something that wasn't my job, but in fact this will turn out to be my new job?
  • Why not start a side project for fun? And what if it becomes my main income? What will I lose if I start focusing 1 hour a day for 3 months? Will a new skill hurt me? And what can it bring me? What is the price of the sacrifice? In fact, can what I will sacrifice be called a sacrifice at all?
  • How do you start a side project? Am I drawn to something different? Is my attention registering the same information from different sources? Has something been on my mind for a while? Why don't I explore it? Should I give it at least 30 minutes of attention?
  • Let's go further - why shouldn't I become a millionaire? What if everyone around me is light years away from such a perspective? What's actually stopping me? Are there some wrong beliefs ingrained in my subconscious since childhood? Or do I just not have the time? And what will I do if I don't try? Will I win if I don't try?

Now let's see how far someone in history has come, after simply asking enough questions and strategically seeking the answers:

he most impressive idea when I first came across self-help literature was the story of Henry Ford's interrogation - how a Chicago media outlet publicly accused him of being indifferent to the war (World War I). He exercised his right to challenge the accusation in court, and the lawyers began to ask him various questions from the general history of America to prove the accusation, such as "How many soldiers did Britain send to America in 1776 to suppress the rebellion?" His answer:

If I really want to answer the stupid questions you ask, or any of the other questions you ask me, let me remind you that I have a series of electric buttons on my desk. By pressing the right button, I can summon people who can answer any question related to the business to which I devote most of my efforts. Now, would you please explain to me why I have to overload my mind with general knowledge just to be able to answer questions, when I have people around me who can provide me with any knowledge I need?

We learn about this story from the books of Napoleon Hill . To prove his conclusion, he writes:

An educated person is not necessarily one who has an abundance of general or specialized knowledge. An educated person is one who has developed the faculties of his mind to such an extent that he can acquire anything he desires, or its equivalent, without violating the rights of others.

Through my professional prism as a Project Manager, it sounds to me like "... he can implement any project he wants..."

When you become a Project Manager , you put yourself in situations like Henry Ford's every day. You work with highly qualified specialists .

But not everyone has the talent to explain complex technological architecture in simple language. Some simply don't have the patience or desire to do so. You need the ability to ask questions and seek out the necessary information from people more knowledgeable than you.

At the end of the day, the responsibility for dealing with any challenge is yours. The more you ask, and the more detailed and clear picture you paint in your own mind, the closer you are to the conclusions you need.

You will inevitably annoy someone. Accept that this will not violate their rights.

A Chinese proverb says:

He who asks a question is a fool for a minute; he who does not ask one is a fool for life.

I would add - the one who does not ask the questions is shirking the responsibility of taking others out of the prolonged ignorance in which they would always prefer to remain, just to have one more day of the comfort of mediocre performance.

It's certainly good to ask questions, we already agree.

But how do you get the answers you need?

On first principles in thinking

The concept of first-principles thinking is both paradoxically simple and intuitive, yet extremely laborious and cognitively intensive. As a result, it is not given the respect it deserves in the modern arsenal of those who want to excel in their endeavors.

A person who has spent some time in a technology organization (or similar environment) perceives qualities such as problem solving and critical thinking as the foundation for overcoming any challenge. They are also a requirement on almost every CV , whether for a Project Manager or any other more serious position.

Often, however, we combine the two, only to find that something is missing from the picture, and then we switch into full-on dedication mode, determined to keep going until we get to the truth we need.

In order to properly perceive the thought technique, we need to look at it from several angles, through the eyes of several prominent minds, and give simple examples.

The points of view:

Thinking from first principles is a technique for approaching problems from a beginner's perspective, even if you're not. Instead of working with analogies and what others around you "know" to be true, you put in the effort to figure out what is actually true, and therefore what is truly possible.

You apply it by asking a lot of questions, challenging the assumptions of others, and digging deeper than others. You go far, all the way to the root causes, to establish the truth about yourself.

In physics, the concept is defined as “starting directly at the level of established science, and not making assumptions relying on existing models.” The most amazing thing is that the definition has been around for at least 2,500 years. The author is Aristotle, who synthesized it as “the first basis from which a thing is known.”

We cannot fail to mention the modern example of Elon Musk:

We go through life reasoning by analogy, which basically means copying what other people do with slight variations. We have to do that too. Otherwise, mentally, you won't make it through the day. But when you want to do something new, you have to take a first principles approach.

Here's how one rocket scientist, Farnham Street, summarizes the concept:

The main drawback [of thinking from first principles] is that it's really hard. Thinking analogously, or copying what others are doing, is like being the opening act of a band and playing someone else's music. Whereas with first principles thinking, you go back to the fundamental raw materials of music, which are the notes, and from there you create a new song from scratch. That's a first principles approach. It's really hard to do, because so much of what we do in life is motivated by what we've done before, and also by what others around us are doing. First principles thinking, if you take it to the extreme, can be really ineffective, because we learn by imitating other people - even learning how to walk comes from copying others and modeling their behavior. Part of the difficulty is choosing what to question, because you can't survive if you're just questioning everything you do. Choosing what to question and also using knowledge in a way that will enrich you instead of worry you.

You don't have to be Elon Musk or a rocket scientist to make a difference - when you stop reasoning by analogy and start challenging the prejudices of the people around you, you no longer 'fit in'. And it's very likely time to change your social circle.

All books on success talk about the enormous influence of your surroundings, or as it is known in folk folklore, " you become what you associate with " - you start copying their behavior, their way of thinking, and their worldview in general, until you equate your bank account with the 5 people you meet most often.

You will inevitably find yourself in situations where you can't just change your environment - the simplest example - you are a Project Manager and have a project team assigned - you can't just get another 10 engineers. An ideal moment to apply first principles thinking, and go further in challenging and exploring, or simply demand answers to the questions you have so wanted to keep quiet.

It will be difficult, you will upset some people, you will wander into the unknown, you will have to learn new things. But it will be worth it - often it will be the only approach to deal with the "insurmountable" obstacle

Real examples

That being said, many of the biggest breakthroughs in history have come from someone's effort to think from first principles. This includes the classic examples of SpaceX and Tesla, the breakthrough that led to the architecture of artificial intelligence, the invention of the airplane, the discoveries of nuclear power and general relativity, and many more.

Erwin Schrödinger

The task is not so much to see what no one has yet seen, but to think what no one has yet thought in relation to what is visible to everyone.

Try to apply the above thought to your own social circle?

The most eloquent modern example is related to the mass spread of artificial intelligence.

OpenAI co-founder (the company that created chatGPT) and chief scientist - Ilya Sutskever, shares the following :

…. Everyone knew that deep neural networks cannot be trained. It is impossible. […] Today we take deep learning for granted. Of course, a big neural network is what you need. You feed it data and you get amazing results. Everyone knows this. Every child knows this. How could we not know this? How could something so obvious have been unknown? ….

_For a clearer picture, let's clarify - humanity did not create an algorithm that would always tell the machine what to do next, but an algorithm through which the machine would constantly and continuously train itself to make the right decisions. With each passing day, artificial intelligence is getting better.

And for even more eloquence - The algorithm that guides Tesla's self-driving cars is not fed with simple commands like "If you see > a red octagon > on the right > with the inscription "STOP" = stop! Instead, a sufficient number of videos of live drivers are marked with "correct driving" (the driver stopped at a stop sign) / "incorrect" (respectively, did not stop), without mentioning the sign, after which the machine itself analyzed the similarities in both to determine that the presence of something octagonal red is found in all = correct and done - the result is a computer that will make mistakes shockingly fewer times than some drivers in Bulgaria._

Someone simply challenged what everyone thought was “true,” dedicated the effort and time to finding out if it was actually impossible, and the result was perhaps the biggest breakthrough in software history.

Some simpler examples from everyday life

Or how to apply the mental model of first principles to your own projects.

Let's say you've decided to take on something challenging. For example, you're going to buy a home. The first thing you think of are the people you've talked to and shared their successes, failures, and thoughts on the subject. That is, you immediately look for an analogy - if someone else has done it, I can do it too... I'll just copy it. However, if the reasoning of others was something like "Nowadays, real estate is very expensive..."; "Why should I enslave myself with a 30-year loan..."; "All those banks ask for a large amount for initial payments and fees..." then with the primary approach of analogy, you isolate yourself back into the circle of mediocrity.

On the other hand, if you start asking questions and are determined to put in the time and energy until you get to the truth, you will find that “The properties that everyone sees on the internet are mega expensive, and that's exactly why no one has bought them - they're just sitting there advertised”; “I'll actually never be 30 again until the end of my "credit age"; “It turns out that there are quite a few banks that offer the opportunity to finance everything in the deal - down to the last penny”

Instead of starting to talk to the people around you and copying them as the second step, you start from the fundamental known truths - "How do you buy a property?"; "How do you finance a deal? - What are the participants actually interested in - buyer, seller, lender?"; "What is the real cost of financing?"; "Are there anomalies in the arithmetic mean that may be in my favor?"; "What and where can I negotiate in my favor?"

From personal experience, similar to the above example, in 15 years I changed 15 different apartments in Sofia, and I found that for every 10 listings there are 1 or 2 that are offered 10-20% below the market price - always for some strange reason . And, if the participant is willing to negotiate, very interesting results can be obtained in my favor.

I saw the same statistics during a home buying exercise.

Applying the mental model from a first principles standpoint is adequate everywhere , and is not reserved only for great thinkers and scientific discoverers.

When you are a Project Manager, you will sometimes hear a project participant express a concern that scares everyone. Then it is your job to ask the right questions and get to the truth, only to find that the statement is not worthy of further attention and was the result of simple panic.

It's not that the work is boring, on the contrary - in other similar situations, in order to keep the project going, we will have to find a new way of doing things that we haven't done before. And guess who will have to work hard to find it by starting with the questions, reading the information, listening to all the points of view, and then connecting everything into a unique breakthrough idea?

Scott Berkun synthesizes it in one of the best possible ways:

…Good Project Managers are that force. They are driven to keep moving forward, always looking for something that can be improved faster and smarter. They seek chaos and turn it into clarity. As skeptical as they must be, Project Managers are also optimistic that all problems can be solved if enough intensity and focus are put in. For reasons they themselves cannot fully explain, they continue to hold the torch against ambiguity and doubt and refuse to give up until all possible alternatives have been explored. They believe that good thinking wins and that it takes effort to discover good ideas.

The absolute example:

Inside every little child lives the discoverer. The mental model from the position of first principles is somehow spontaneous.

My son is 2 years old, and he often asks the question Why?

“Dad, why are we getting dressed to go outside?”

  • “so that we don't get cold”

    “But why?”

  • “because we might catch a cold”

    “But why?”

and so it goes on until it breaks the topic down to the core of things, or until it gets hungry - I often have to change the topic with a game - it just doesn't get enough, and sometimes I haven't delved into the topic enough to have all the answers...

In children, the first instinct is to strive to understand things at the level of raw materials that have come out of the factory.

A unique quote from Dan Koe reveals the idea in depth:

Humans have invented mental models like language, culture, concepts, religion, and stories so that they can adapt, build, and acquire the knowledge and skills needed to thrive in any situation. This is the skill that makes us unique. This is the skill that most people have lost. You see, as children, we love adventure. We love to make discoveries and establish truths. We make mistakes and learn from them. We sometimes get burned. But then our growth stops being based on mistakes. It starts being based on the distinguishing traits that our parents and teachers don't like about us. The traits that they find annoying and unacceptable. The traits that they think won't lead us to the vision of success that they've been conditioned to believe is the only possible one, without opening our minds to the discovery that there's never just one 'right way'.

In other words, we grow up, and instead of preserving the discoverer within us, we go into a “copy and analogy” mode, just to be accepted and loved. Over time, we pay the price because we have buried “first principles” – the tool for dealing with any challenge – and we surrender to mediocre and defeatist survival.

Jesus says it best:

…. Suffer the little children to come unto me, and forbid them not: for of such is the kingdom of God. Verily I say unto you, Whosoever shall not receive the kingdom of God as a little child, he shall in no wise enter therein . ( Mark 10:15)

By the kingdom of God, understand the ideal of the perfect life - God's Paradise established on earth. Your personal world perfect and complete.

Why does it say “who does not accept” and not who does not try, does not understand, does not work out…. In order to achieve your highest aspirations, you need to be childishly “naive.” To accept that there is an ideal and perfect way.

Why isn't it possible?

Children have no prejudices. They have no limiting beliefs.

You try to limit them, but they will still wonder what's on the other side.

They will ask why. They will explore. They will try.

They will believe.

They will get burned and make mistakes.

They will find it, and they will succeed.

And while the Lord gave advice to the 'grown-up' - " Truly I tell you ... whoever does not...has nothing at all...",

for the children (for those who believed more childishly) he issued a double command -

“ …leave the children…don’t stop them….”

Keep asking questions.

Every second of the research effort is worth it.

The "aha" moment - the moment you make the discovery, find the answers, arrive at the truth, overcome the challenge - is an incomparable experience.

At such moments, a combination of neurons in your brain fires simultaneously for the first time, bringing such a strong surge of motivation that your gait changes. Happiness and a sense of fulfillment begin to haunt you.

There are no impossible projects.

You have the weapon to realize any idea.

Why can't you handle it?

The double command of Almighty God is your confirmation that you are on the right path.

Follow me for more in the series

More on the topic of First Principles in Thinking:

I recommend you:

Lenny Rachitsky 's blog , from which the topic was inspired Steven Johnson's book - "Where Good Ideas Come From: The Natural History of Innovation" and his entire bibliography
The best book on Project Management by Scot Berkun: Make Things Happen: Mastering Project Management