The benefits of analysing complex problems through critical thinking and extreme questioning – 21 examples

At work, I am often referred to as a ‘risk man’. This is because it is built into my DNA that I can predict the future based on the (often potential) risks I see because of analysing a situation. I need context, data (information, reports, or analyses), consideration of different perspectives and time to recognise the topic before I get down to business. There are also times when I reach back to previous experiences. This allows me to ask tough questions at a very early stage of a project that we would have asked ourselves anyway in the near future. This allows me to look at a situation from a completely unique perspective and to take actions that may protect us from failure in the future.

On a day-to-day basis, ‘critical thinking’ and ‘extreme questions’ help me to do this. Importantly, these help me not only focus on the threats, problems, or dangers themselves but also to come up with fresh and transformative ideas.

According to the paper ‘Developing soft skills and critical thinking’ published in The European Proceedings of Social and Behavioural Sciences: “a critical thinker is able to separate fact from fiction, honesty from lies, accuracy from inaccuracy”.

To find out how this can be learned and what can help with this, I will try to break down the topic.

What is critical thinking?

Critical thinking is the process responsible for processing information. It is supposed to contribute to a rational understanding of the problem we are facing (or the situation we are in) and to making, based on reliable and understandable data, a considered and structured (e.g., arranged in a process) decision. In other words, critical thinking involves:

• looking beyond obvious sources of information, opinions, and existing processes,
• using logical thinking to:
  • examine assumptions,
  • distinguish facts from opinions,
  • and breaking down complex problems into smaller parts,
• and finding effective solutions.

Critical thinking is getting to the heart of problems by asking intelligent (pertinent and sometimes extreme) questions so that you can make good judgements based on:

• facts
• data,
• evidence,
• experience,
• and observations.

It does not rely on the use of:

• emotions,
• assumptions,
• conjecture,
• opinions,
• your own prejudices,
• or existing processes and procedures.

Critical thinking from the perspective of data

A 1972 survey conducted by the American Council on Education found that 97% of respondents identified developing students’ critical thinking skills as the most important goal of undergraduate education.

The science faculty members taking part in the survey overwhelmingly, 89%, stated that critical thinking was their primary teaching goal. However, only 19% were able to define what it is.

Decades passed, during which increased workers were being educated to understand the importance of critical thinking. However, the education system itself has completely failed to address this issue.

In 2016, a survey was conducted on 63,924 managers and 14,167 graduates. It showed that 60 per cent of company leaders identified that critical thinking was number one on the list of social skills that graduates lacked.

It does not get any better over time. Despite constant talk of critical thinking as one of the key factors needed to develop people and the education system and drive the economy, market needs have never been filled.

According to a report by the Society for Human Resource Management, 84% of recruiters say there is a deficit of key social skills such as creative and critical thinking among job candidates.

Critical thinking has become a highly desirable skill in today’s job market. This is because it seeks to find the optimum solution to a problem and involves being open-minded and considering different points of view before drawing conclusions.

In terms of the prognosis for the future, no change is expected.

The Future of Jobs Report indicates that by 2025. 50% of the workforce will require retraining due to the increasing use of technology. The same report indicated that critical thinking and problem solving are at the top of the list of skills that employers believe will continually grow in importance.

Using critical thinking in business

Critical thinking is relevant to everyone in an organisation, but business managers are likely to benefit the most from it. Their job is not only to ensure that all team members are doing their jobs properly but also to make difficult and important decisions that can have far-reaching repercussions.

However, integrating critical thinking into business life can be a considerable challenge. Most organisations are either used to existing patterns or are heavily influenced by people, concepts or processes that make it difficult to open their minds to look at things objectively.

Meanwhile, when we use critical thinking, we cannot simply take things as they are. We need to carefully measure and question information to improve how we think about it. On the other hand, we can’t be stuck in it all the time because being indecisive can cripple our business or discourage our teams from taking action. Once we have thought through the information and the options available, let’s not be afraid to decide, because focusing on problems for too long will lead to ‘indecisive leadership’.

You can hear about other remarkably interesting managerial mistakes in the Foundations of Organisation podcast in episode 51.

Critical thinking does not have to be used in every decision

Not every business decision requires deep and critical thinking, either. The amount of time and energy we will spend on a decision should be directly proportional to how the decision affects our business.

If our view is to choose the filling of Christmas chocolates for customers, between strawberry and cherry, then let’s just decide. However, if we are about to reorganise the business or hand over an area of responsibility to new people, we need to stop and think about the details before we move forward.

Competencies needed for critical thinking

I have written about the importance of social competencies in business in one of my articles entitled ‘Social competences. “The most successful people are those who can talk to people“. Personally, I still believe that everything we do starts with communication and ends there. The same is true for critical thinking.

Communication

According to LinkedIn’s Global Talent Trends report, 89% of recruiters say that when a hire doesn’t work out, the reason is usually a lack of social skills. 77% of managers are looking for employees who can think critically and, when it comes to hiring, 46% of them say that new hires nevertheless need to improve their communication skills.

Critical thinking and communication skills are paramount, and they are what allow us to open up and understand other people’s perspectives. It allows us to ask the right questions and, through them, seek solutions. Additionally, once we, as managers, have made a decision, it will be crucial to communicate it to the rest of the team or other stakeholders.

Analytical thinking

Another important competence is analytical thinking. By gathering data from multiple sources, we can discard our preconceptions about the topic we are dealing with. This includes:

• independent judgements,
• focusing on facts
• data and figures,
• and the ability to ask thoughtful questions based on them.

58% of managers say analytics is important to their organisation. Only less than 1% say that analytics will not be important to their business even five years from now. This unequivocally indicates that analytics and analytical thinking skills will be a ubiquitous part of the business world by the end of the decade.

Analytical thinking, not least in the high-tech world, allows us to find a solution that is feasible to execute yet well-optimised and efficient. Sometimes this means making a decision to see if the solution (or part of it) we assume is likely to work and then moving on to the next one. Creative thinking is also an important part of analytical thinking. It involves figuring out how to combine improbable (incompatible) sources and differing perspectives to find the best solution. The most obvious ideas are not always the best ones.

Perceptiveness, openness, and attitude

Stanford Research Institute International has identified in its research that human competence is responsible for 75% of success, compared to 25% when it comes to technical skills.

Open-mindedness goes hand in hand with our attitude, as necessary as other skills. If we do not consider different perspectives, assumptions, or beliefs, we will not see the problem or the source of the problem. Perceptiveness, on the other hand, will allow us to see and identify the problem and even predict potential problems based on our past experiences.

How to start the critical thinking process for problem-solving in a company

When faced with a problem to solve, the critical thinking process should start by identifying the problem and what it really is. Defining it wrongly can lead to a poor understanding and, therefore, incorrect conclusions. But how do you dress this up in an easily repeatable process?

Identify the problem

For an example of further analysis, we can assume that we, together with our team, have made a product that we thought would appeal perfectly to the chosen target group. Meanwhile, we find that after going into production, sales are virtually nil, and customers who are interested in the product end up dithering.

Digging deeper into the subject, at first glance, it looks like the problem is that the sales team is too slow in serving customers.

Perform a problem analysis preceded by data collection

Once we have a pre-identified problem, we should perform a deeper analysis of the problem. Collect data related to it and feedback from the teams. Given that in the case assumed earlier, customers are also involved in the core of the problem. We also need to get their perspective (data). Questions such as:

• Is this because our teams do not have the right experience?
• Or did we make a mistake at the recruitment stage?
• Are people working in roles they don’t feel comfortable in?
• Maybe it’s a hardware problem?
• Maybe we’re using the wrong CRM, or it’s a poorly laid out sales process?
• Is the problem in materials that are not very versatile?
• Why does the customer service process take so long?
• Can’t customers show more self-reliance?
• Does the problem not lie with the customers?
• Is our application not responsible for the problem?

Additional questions to ask yourself when sitting down to solve a problem.

When preparing to solve a complex problem, it is worth asking yourself questions such as:

• What is the real problem?
• Why does this problem or challenge exist?
• What information do I need to gather to understand more?
• What should the target process look like?
• What should the notes look like?

In addition, questions such as:

(click on the question to expand)

Look for alternatives

Asking questions will be able to generate alternative sources of problems and, therefore, solutions. The more data we acquire about them (especially those that contradict our initial assumptions), the more likely we are to find the true ones.

Discard the unnecessary and act

Next, we select the most important and likely causes of the challenge we face. In addition:

• we look for solutions,
• create an action plan,
• prioritise,
• communicate
• and implement decisions.

Observe and analyse

After everything, we should continue to look at what is happening with our solutions. We are constantly trying to question, change and improve them. Because we may have solved a customer problem today, but that doesn’t mean you can’t do it even better in the future.

The solution to a problem is not always obvious

In this exercise, we can assume that the problem was not related to the sales team but occurred directly in the application itself. This one proved to be lacking in transparency and customer friendliness. As a result of problems with its use, the sales team had to spend more time introducing the customer to the app each time than they had anticipated. The solution chosen was to redesign it, which increased conversions and sales. But in the future, when we look at the same problem again, instead of this solution, couldn’t we design onboarding and automate the sales process itself up to a certain point?

From real-life examples, I can share a story that took place many years ago. We were working on our own startup at the time. We created a tool that turned a smartphone into a microphone. When creating our product, we wanted to solve the logistical problem of communicating it to people who wanted to ask a question to the presenters of a lecture or workshop. The conference organisers were enthused by the solution we came up with, but the audience did not want to use it. By thinking critically and asking dozens of non-obvious questions, we were able to discover the real source of the problem.

It turned out that it was not connected directly with the tool but with the fear of asking questions in public, which, according to research, was the number one greatest fear among people. This allowed us to completely change the way we viewed our tool and offer a completely different solution in the form of anonymous communication.

At the first conference, where we tested the already improved solution, the number of questions asked from the audience increased from zero to exactly 912 (from 1,000 people in the room).

The power of extreme questions, not only for critical thinking

An important thing to mention with critical thinking is extreme questions.

Extreme questions are those that are meant to stimulate our creativity and help us find a solution that we would not have even dared to think about before.

They are very often used during brainstorming sessions and are also used to create unique business models (so extreme that they defy our critics and competitors).

An example of such extreme questions can be seen in the debate we had some time ago in our People Ops department when we were confronted with the low matching rate of candidates to our advertisements. After many different conversations and attempts to identify the problem, I asked the question:

“How would we search for candidates if we couldn’t use social media, job boards, our website or any of the other ways we know today?”

Extreme questions I am currently working on myself

Other questions I am currently working on to help me understand even better the position in which our organisation finds itself can be found below. I hope these will be of any help to you in the case of your business.

1. If our aim was to deliver just one particular service/product, then what would it be?
2. If we were all to work together on just one annual goal, which one would we choose to deliver and why?
3. Who would we recruit without regard to cost?
4. If we had to recruit someone in a week, what would we do?
5. If we had to recruit a person by making contact with them just once, how would we do it?
6. If we could only do one Employer Branding thing a year, what would it be?
7. If we could disregard costs, what EB action would we plan?
8. If we could print the ideal employee (e.g. a developer) on a 3D printer and the system running it asked us for (up to) three qualities/skills that this person possesses, what would it be?
9. If we were making a project to sustain life and release it into production, what would we have to do to ensure that no one who uses it dies?
10. If we couldn’t put projects into production any other way than by pressing two buttons – “upload” and “undo” – then what would we have to do?
11. If we only worked on maintenance projects, then how did we provide development for our teams?
12. If all our clients disappeared and we had to earn our growth and brand from scratch, what would we do?
13. If we were to start selling our services and didn’t have the internet to do so (even to search for something) how would we do it?
14. What if we were forced to charge customers in a completely different way? What business model would we choose?
15. If we had to raise our prices twice how would we justify it?
16. If we had to do marketing activities without using everything we do now how would we do it?
17. If we had to finish our project in a maximum of two sprints, what would we do to achieve this?
18. What would have to happen to build the product from scratch in half the allotted time?
19. If we didn’t have the opportunity to ever talk to the client, and we needed to complete or build the product for them from scratch, what would we need to do (how would we find out what to build)?
20. What would be the coolest thing to build on the project? What would we build if we didn’t have to listen to or care about anyone else but ourselves? (No, what would be the most profitable thing)
21. If we ordered tomorrow that all project teams swap their projects what would we have to do (or constantly do) to make this happen?

The benefits of critical thinking and asking extreme questions

The more time we spend on critical thinking, the easier it will be to come up with questions before a problem even arises. Additionally, it will help us to:

1. keeping our emotions in check,
2. controlling the chaos around us (with facts and data),
3. questioning information,
4. seeing non-obvious connections between problems and ideas,
5. pointing out inconsistencies and errors,
6. seeing the perspective of different people and departments,
7. building a well-qualified team,
8. streamlining and creating efficient processes,
9. having plans for potential challenges,
10. delegating tasks to qualified team members,
11. finding new ways to deal with existing problems,
12. communicating effectively,
13. coming up with fresh transformative ideas,
14. setting a boundary for when to stop thinking and move on to action.

At the World Economic Forum in Davos, creative and critical thinking skills came second and third on a list listing the most important skills we will need to thrive in the industrial revolution.

Critical thinking is considered by experts to be a skill we can learn. We can be helped by finding the areas in our workplaces that seem to lack critical thinking the most. We can then start by tackling smaller problems, using the process I suggested earlier so that over time we can be able to move on to bigger challenges in this way.

Sources and supplementary material

https://hbr.org/2019/10/a-short-guide-to-building-your-teams-critical-thinking-skills
https://www.forbes.com/sites/helenleebouygues/2018/11/21/how-critical-thinking-improves-life-outcomes/
https://www.criticalthinking.org/pages/the-state-of-critical-thinking-today/523
https://journals.sagepub.com/doi/10.3102/0034654315605917
https://www.cambridge.org/elt/blog/2019/03/07/critical-thinking-survey-results/ 
https://www.kallidus.com/resources/blog/soft-skills-masterclass-lesson-5-critical-thinking/
https://arc.dev/developer-blog/analytical-skills/
https://www.amanet.org/articles/companies-see-need-to-build-analytical-skills-in-their-organizations-a/
https://www.payscale.com/data-packages/job-skills
https://longform.asmartbear.com/extreme-questions/index.html