A core skill sorely missing from the world of work is critical thinking.

At work we're exposed to theories that have no utility, or people with strong opinions yet no data, or ways of working that don't work and whole host of other situations where heavy dose of critical thinking is required.

We need to be more critical and skeptical, even of plausible sounding theories.
 
Thinking critically about information, communication, concepts, methods etc can help you gain clarity, truth and understanding.
 
I prize two core skills when recruiting for my teams: critical thinking and good communication skills. After all, have you ever met a critical thinker who isn’t a good communicator? Painfully difficult and annoying to work with.

I will introduce three questions I use, along with a robust and complete list of excellent questions from the CIA, called the Phoenix Checklist. I have these questions in my note taking tool and use them often.


In this post:

  1. Critical thinkers can be annoying
  2. The two every-day questions I use
  3. The Phoenix Checklist

Critical Thinkers can be annoying

Critical thinking is annoying, but it’s annoying in a “good for business” kind of way.

Critical thinking is about getting to the heart, the essence, the principle, the truth. Using questions is a typical form of expressing critical thinking, but so too is developing the muscle in our own minds.

When we develop this muscle we have much more over what we let affect us, who we hang out with, what we choose to believe and how we live our lives. We are no longer swayed around with other people's agendas or motivation, we no longer take everything on face value and we develop insights and data to make better decisions.

People with strong opinions no longer push aside our own reason and logic. We can understand the world with more clarity.

It can be annoying though when those who have developed this skill ask questions. Deep, insightful, clarifying questions. Questions that make people truly think. Questions that undo someone's argument in seconds (not done with bad intentions I would like to add).

Questions that tear an idea apart or poke a giant hole in a theory. Questions that lead to more questions, questions that demand more insight and questions that challenge those who aim to bulldoze ill conceived ideas.

Good questions keep a business alive though.

My go-to questions

The field of critical thinking is ripe with plenty to learn but here are my three go-to questions to ask when listening, discussing and thinking through topics. I use these every single day in work.

What problem are we trying to solve?

This really is a power question. It gets to the heart of the matter and asks people (including yourself) to clarify what your purpose is. I've done a post and video on this question before.

That meeting you're in - what problem are you trying to solve? That project you're about to invest in - what problem are you trying to solve? That piece of work the execs have thrown at you with little insight - what problem are you trying to solve?

The twin version of this question is framed with positive action - what opportunity are you trying to open?

This question cuts through the noise and demands a clear answer. If you cannot explain what problem, or opportunity, you're taking on, why are you doing anything but getting more data and insights?

I've seen entire departments embark on a billion pound transformation without any clear idea why. No problem, no opportunity, no target or destination - just transforming. Chaos.

I've seen teams spend millions of pounds building a digital product with no clear reason why. Nobody wanted it, nobody used it. What problem were they trying to solve?

Is that always true?

This question can be applied in many situations. When someone uses an absolute (Never, Always etc) - is that always true? When someone makes a confident and clear assertion of the truth - is that always true?

Yes, I see the irony of using an absolute to test an absolute, but in this case its justified.

When someone makes a statement that is held as truth ask the question : Is that always true?

Was there ever a time when it was not true? Can you find examples where it wouldn't be true? Is it always the case that it is true - in every situation?

As a simple contrived example, when I was first learning to think more consciously critically, someone made a bold statement that all "in all standup meetings you MUST standup". Is that always true? Of course not. Sure, you should and the reason being is to encourage shorter meetings. But, when we adopted remote work and people were working from home, did we make them standup? When Dave broke his leg and couldn't stand, did we abandon the meeting? Of course not.

It's a very simple example but it brings this to life.

If it's always true, then is the opposite always false?

It's entirely possible for two competing ideas to be true or correct. If someone states that something is always true, then it would be logical to assume that the opposite is always false?

But is it? Are there times when the opposite is also true or correct? Could it be possible that both things are true at different times, or in different contexts?

Another simple example. In a heated debate about "Agile Frameworks" (you know I don't like these), someone said that one framework was the only way to achieve business results.

That would suggest that all other ways don't work and that any other way would not achieve business results. It takes less than 1 minute to find a company doing something in a different way and achieving success. The dogmatism that comes with some theories, models and methods leads people to believe that other ways don't work - they do.

In our world of work it's often worth asking this question, particularly when people espouse "one way", "only way", "only option" etc - the opposites of which are rarely false meaning that statement cannot always be true.


I’ve had people tell me that “Bob” is ALWAYS late. Not true. I found many times when Bob started early or finished late, and he was most certainly not ALWAYS late.
 
I’ve had people tell me the software DOESN’T work when they find a bug in it. It does work but they have found a bug, but it doesn’t mean the whole thing is broken. A case for being very accurate when we’re reporting faults in products etc.
 
I’ve had people tell me this tool, or that tool, is the best tool on the market. Maybe, but let’s run a proof of concept with some measures to be sure. How have they ascertained this? What problem does it solve? How do they measure it? Are all the rest really that bad?
 
I’ve seen websites with false information; strategies that lie about the current reality; measures and dashboards that are careful to omit certain information; and stories from people about successful deliveries that are clearly failing (I call this Watermelon reporting - green on the outside, red in the middle).
 
There is so much misinformation, subjective opinions and lies flying around in business that it’s very important a critical view is applied.

If more people asked critical questions to get to the truth and facts, everyone would make much better decisions.

Asking good questions like these help to keep the business alive. 
 
I am always inspired by Edward Deming’s quote:

 
“Without data, you’re just another person with an opinion”

The Phoenix Checklist

The problem

  • Why is it necessary to solve the problem?
  • What benefits will you receive by solving the problem?
  • What is the unknown?
  • What is it you don’t yet understand?
  • What is the information you have?
  • What isn’t the problem?
  • Is the information sufficient?
    • Or is it insufficient?
    • Or redundant?
    • Or contradictory?
  • Should you draw a diagram of the problem?
    • A figure?
  • Where are the boundaries of the problem?
  • Can you separate the various parts of the problem?
  • Can you write them down?
  • What are the relationships of the parts of the problem?
  • What are the constants of the problem?
  • Have you seen this problem before?
    • Have you seen this problem in a slightly different form?
  • Do you know a related problem?
  • Suppose you find a problem related to yours that has already been solved. Can you use it?
    • Can you use its method?
  • Can you restate your problem?
    • How many different ways can you restate it?
    • More general?
    • More specific?
  • Can the rules be changed?
  • What are the best, worst and most probable cases you can imagine?

The plan

  • Can you solve the whole problem?
    • Part of the problem?
  • What would you like the resolution to be?
    • Can you picture it?
  • How much of the unknown can you determine?
  • Can you derive something useful from the information you have?
  • Have you used all the information?
  • Have you taken into account all essential notions in the problem?
  • Can you separate the steps in the problem-solving process?
  • Can you determine the correctness of each step?
  • What creative thinking techniques can you use to generate ideas?
    • How many different techniques?
  • Can you see the result?
    • How many different kinds of results can you see?
  • How many different ways have you tried to solve the problem?
  • What have others done?
  • Can you intuit the solution?
  • Can you check the result?
  • What should be done?
    • How should it be done?
    • Where should it be done?
    • When should it be done?
    • Who should do it?
  • What do you need to do at this time?
  • Who will be responsible for what?
  • Can you use this problem to solve some other problem?
  • What is the unique set of qualities that makes this problem what it is and none other?
  • What milestones can best mark your progress?
  • How will you know when you are successful?
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