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The Benefits of Analysing Complex Problems with Critical Thinking and Extreme Questions

I'm often called the 'risk eliminator', thanks to my knack for critical thinking and asking the right questions early on. This approach helps us not just avoid potential issues but also encourages fresh, innovative thinking. It's about applying insights practically and ensuring our ventures are safeguarded and successful. In this article, I'll share these strategies to empower you to transform risks into growth opportunities.



Before I start to carry out tasks, I need context, data (information, reports, or evaluations), insights into other perspectives, and time to study the topic. Sometimes, I also think back to past experiences. Thanks to this, at the earliest stage of a venture, I’m able to ask all the difficult questions that we would have to ask ourselves anyway later on. They allow for approaching a situation from an entirely different perspective and taking measures that can safeguard us against failure in the future.

What helps me on a daily basis are critical thinking and extreme questions. Importantly, not only do I focus on dangers, problems, or potential pitfalls, but I also come up with fresh, innovative ideas.

According to Alfia Mamleeva’s ‘Developing Soft Skills and Critical Thinking’ published in The European Proceedings of Social and Behavioural Sciences, ‘Critical thinker is able to separate facts from fiction, honesty from lies, accuracy from inaccuracy.’

To demonstrate how to learn this skill and what might be helpful in the process, I’ll try to break the concept down into prime factors.

Defining critical thinking

Critical thinking is a process responsible for handling information. It allows for a rational take on a problem or situation and making an informed, well-structured decision. In other words, critical thinking consists in:

  • looking beyond the most obvious sources of information, viewpoints, and processes;
  • using logical thinking to:
    • test assumptions,
    • differentiate between facts and opinions,
    • break down complex problems,
    • and – first and foremost – find efficient solutions.

Critical thinking is getting down to the crux of the matter through asking intelligent (pertinent and sometimes extreme) questions that allow for reaching an accurate judgement.


Critical thinking in data

In a study carried out in 1972 by American Council on Education, 97% of respondents considered critical thinking as the most important educational goal of bachelor studies.

As many as 89% of the surveyed faculty members stated that critical thinking is their primary teaching objective. Only 19% of them, however, were able to actually define it.

Decades went by, and the market became saturated with employees who were taught the importance of critical thinking. The educational system itself, however, failed dismally in terms of actually putting the concept into practice.

In 2016, a study was carried out on a group of 63,924 managers and 14,167 graduates. 60% of corporate leaders cited critical thinking as the worst-developed social skill amongst graduates.

And the situation hasn’t improved at all. Although critical thinking is invariably indicated as one of the most prominent competences needed for the development of educational system, economy, and humanity itself, the market demand has never been fully satisfied.

As shown in the ‘Society for Human Resource Management’ report, 84% of recruiters claim that job candidates seem to lack such key social skills as creative and critical thinking.

Critical thinking has become an extremely desirable competence in today’s labour market, and nothing suggests the trend will turn any time soon.
After all, it aims at producing an optimal solution, while involving an open-minded approach to analysing viewpoints and reaching conclusions.

As stated in the ‘Future of Jobs Report’, by 2025, as many as 50% of employees will need to retrain due to the growing impact of technology, whereas critical thinking and critical problem solving are perceived by employers as skills that will continually grow in pertinence.

Using critical thinking in business

Although critical thinking is vital from the point of view of each organisation member, those who benefit from it to the greatest extent are probably the managers. Their task is not only to ensure that everyone does their work correctly, but also to make important – often hard and far-reaching – decisions.

That being said, integrating critical thinking into the corporate structure may prove to be a rather tall order. Most organisations are used to existing patterns, or remain under a strong influence of certain people, concepts, or processes, which makes it difficult for employees to open their minds and look at issues objectively.

Meanwhile, using critical thinking necessitates a fresh take on things. We need to carefully gauge and question data to amend the way we approach problems. On the other hand, the process can be only so long, as hesitation may paralyse our business or discourage our teams from taking action. Once we have analysed all information and weighed our options, let’s not be afraid to make a choice – too much wavering may result in indecisive leadership.

Not all decisions need to be made with the use of critical thinking

Not all business choices require serious critical thinking. The amount of time and energy we spend on reaching a decision should be directly proportional to its business importance.

If our task is to determine whether Christmas chocolates for clients should have strawberry or cherry filling, let’s not dwell on this too much. But if we intend to restructure the organisation or delegate some responsibilities to new people, we have to stop for a while and think things through before we take a step forward.

Competences needed for critical thinking


Effective communication

According to the ‘LinkedIn’s Global Talent Trends’ report, 89% of recruiters claim that when a hired person falls short of expectations, the commonest reason for it are poor social skills. Despite the fact that 77% of managers look for candidates who are able to think critically, 46% of them state that the newly employed people still need to hone their communication skills.

Communication skills are the most vital component of critical thinking – they let us open our minds and understand another person’s perspective. They also allow us to ask pertinent questions and look for solutions. Additionally, once we – as managers – have made a decision, we need to communicate it adequately to the rest of the team or other stakeholders.

Analytical thinking

Another essential skill is analytical thinking. It lets us gather information from multiple sources and eliminate any biases towards a given issue. It also consists in:

  • carrying out objective, independent evaluations;
  • focusing on facts;
  • operating on data and numbers;
  • as well as being able to use them as a basis for formulating questions.

58% of managers claim that analytics is crucial for their organisation. Only less than 1% state that it won’t be important for their business operations for at least the next five years. This, in turn, clearly indicates that by the end of the decade, analytics and analytical thinking skills will have become an inseparable part of the world of business.

Analytical thinking – which extends beyond the newest technologies – helps us find viable, optimal, and efficient solutions. Sometimes, it means making a decision to test the validity of an assumption, and then repeating the process with another one. An important element of analytical thinking is also creative thinking. It consists in finding a way to connect incompatible sources and conflicting perspectives to find the ideal solution. After all, the most obvious conclusions are not always the best ones.

Perceptiveness, openness, and the right attitude

According to the research carried out by Stanford Research Institute International, success depends in 25% on technical skills, and in 75% – on human ones.

Open-mindedness, accompanied by the right attitude, is needed no less than other skills. If we don’t account for different points of view, assumptions, or beliefs, we won’t be able to notice the problem itself, let alone its roots. Perceptiveness, on the other hand, will let us not only detect the issue at hand, but also foresee potential complications based on previous experiences.

How to begin the critical thinking process while solving problems at the company

When we face an issue to solve, we should begin the critical thinking process by pinpointing the crux of the matter. Should we fail to do so, we might end up working at cross-purposes and reaching erroneous conclusions. But how do we approach this right?


🔹 Identify the problem

For the purposes of further analysis, we may assume that – together with our team – we have launched a product that is supposed to resonate with our target group perfectly. It turns out, however, that the sales are extremely low, and all potential customers pull out eventually.

At first glance, it seems that the crux of the problem is slow customer service.

🔹 Analyse the problem after having gathered the necessary data

Once we have identified the issue, we should analyse it in more depth. This involves collecting relevant data and obtaining feedback from teams. Given the significant role clients played in the previously discussed case, it is essential to also understand their perspective on the matter. What may help us collect information are the following questions:

  • Does this happen because our teams lack experience?
  • Did we make a mistake at the recruitment stage?
  • Do employees assume professional roles they feel uncomfortable with?
  • Does the issue arise from equipment?
  • Do we use an unsuitable CRM system, or are we dealing with an ill-devised sales process?
  • Does the problem lie in not-so-universal materials?
  • Why does customer service take so long?
  • Can customers be more independent in their actions?
  • Is the problem unrelated to customers?
  • Is the issue caused by our application?

While confronting a complex problem, it is worthwhile to ask yourself such questions as:

  • What is the heart of the problem?
  • Why does the problem or challenge exist?
  • What information do I need to gather to gain a deeper insight?
  • What should the final process look like?
  • What should my notes look like?

The following questions might be of further assistance:

  • Who?
  • What kind?
  • Where?
  • Why?
  • How?

🔹 Look for alternatives

Asking questions may help find alternative roots of the problem, and at the same time – solutions. The more information we acquire about them (especially if it contradicts our tentative assumptions), the higher the chance of us finding the correct pieces.

🔹 Let go of everything unnecessary and take action

Next, we choose the most important – and the most probable – reasons for the emergence of the challenge we face. Additionally, we:

  • search for solutions,
  • devise a plan of operation,
  • create a list of priorities,
  • communicate and act on our decisions.

🔹 Observe and analyse

Afterwards, we should keep monitoring the effectiveness of our solutions. We need to question, change, and improve them constantly. After all, we might have solved our customers’ problem today, but this doesn’t mean we can’t do even better in the future.

Solutions are not always self-evident

For the purposes of this exercise, we may assume that the fault lay not with the sales team, but with the application, as it turned out to be fairly unintuitive. Due to its poor performance, the sales team needed to spend more time than expected explaining its workings to each customer.

The chosen solution was to restructure the application, which ultimately led to a higher conversion rate and better sales. But if we were to tackle the same issue in the future, wouldn’t it be more practical to develop a cleverer onboarding plan and automate the sales process up to some point?

When it comes to real-life examples, I have a story from many years ago. Back then, we were working on our own start-up. We created a tool that changed a smartphone into a microphone. Our idea was to overcome the problem of passing the microphone around during discussions or Q&A sessions at lectures and workshops.

While the conference organisers were absolutely delighted with our solution, the audience seemed rather reluctant to use it. Thanks to critical thinking and asking dozens of non-obvious questions, we were able to get to the heart of the matter.

It turned out that the problem didn’t lie with the tool itself, but with the fear of asking questions in public – which, according to various studies, ranks among the most prominent sources of anxiety in people. It let us see our solution in a completely different light and, subsequently, direct our efforts towards anonymous communication.

At the first conference during which we tested the improved tool, the number of asked questions grew from zero to as many as 912 (with 1,000 people in the audience).


The power of extreme questions – not limited to critical thinking

A crucial concept to mention while discussing critical thinking are extreme questions.
Extreme questions are supposed to stimulate our creativity and help us find a solution we wouldn’t have considered otherwise.

They are often used during brainstorming sessions. Thanks to them, unique business models come to life (revolutionary to the point of defying our critics and competitors).

An example of extreme questions is a debate we had at our People Ops department when we were dealing with a poor match rate between a candidate’s profile and our job requirements. After myriad meetings and countless attempts at identifying the problem, I asked,

‘How would we look for candidates if we were unable to use social media, job boards, websites, or other means we are used to today?

Examples of extreme questions I’m working on

Below are some other questions I’m currently pondering to gain a deeper understanding of our organization’s position. I hope they will be helpful to your business as well.

  1. If our goal was to deliver just one specific service/product, what would it be?
  2. If we all had to work on just one annual goal, which one would we choose and why?
  3. Who would we hire regardless of cost?
  4. What would we do if we had to hire someone in one week?
  5. If we had to recruit a person by making only one contact, how would we do it?
  6. What would it be if we could only do one employer branding activity a year?
  7. If we could ignore cost, what EB activity would we plan?
  8. If we could 3D print the ideal employee (e.g., a developer) and the system asked us for (at most) three traits/skills that person possesses, what would they be?
  9. If we were to create a life-sustaining project and put it into production, what would we have to do to ensure that no one would die from using it?
  10. What would we have to do if we could only put projects into production by pressing two buttons: “deploy” and “retract”?
  11. If we only worked on maintenance projects, how would we ensure the development of our teams?
  12. What would we do if all our customers disappeared and we had to build our development and brand from scratch?
  13. If we had to start selling our services without the Internet (even for search), how would we do it?
  14. What if you were forced to charge customers in a completely different way? Which business model would we choose?
  15. If we had to double our prices, how would we justify it?
  16. If we had to do marketing without using anything we use now, how would we do it?
  17. What would we do if we had to complete our project in a maximum of two sprints?
  18. What would it take to rebuild a product in half the time?
  19. If we never had the chance to talk to a customer again but had to finish or rebuild a product for them, what would we do (and how would we figure out what to build)?
  20. What would be the most incredible thing to build in a project? What would we create if we didn’t have to listen to anyone but ourselves and didn’t have to consider anyone else? (not what would be most profitable)
  21. If we decided tomorrow that all project teams would swap their projects, what would we have to do (or continue to do) to make that happen?

Download the list of extreme questions to spark new ideas and inspire innovative solutions


Advantages of critical thinking and asking extreme questions

The more time we devote to critical thinking, the easier it will be for us to come up with crucial questions even before a problem occurs. Critical thinking may also help us:

  1. control our emotions;
  2. cope with chaos (thanks to factual data);
  3. question information;
  4. discover non-obvious patterns between issues and ideas;
  5. spot inconsistencies and errors;
  6. view things from the perspective of different people and departments;
  7. build a competent team;
  8. devise efficient processes and streamline the existing ones;
  9. develop plans aimed at responding to potential challenges;
  10. delegate tasks to suitable team members;
  11. finding fresh ways to deal with the existing problems;
  12. communicate effectively;
  13. come up with innovative, valuable ideas;
  14. assess when it’s the best time to stop thinking and start acting.

At the World Economic Forum in Davos, creative thinking and critical thinking were ranked second and third on the list of the most important skills needed to flourish during the industrial revolution.

According to scientists, critical thinking is a skill that can be learned. When it comes to our workplaces, we can begin by identifying areas that don’t seem to involve critical thinking to a considerable extent. Then, we may get down to solving minor problems, utilising the process I have suggested, and gradually move on to tackle more serious issues.


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