Critical Thinking Skills for Business: Daily Questions + Phoenix Checklist

Critical Thinking at Work: Asking the Right Questions to Get to the Truth

A core skill that’s sorely missing in the world of work is critical thinking.

At work, we’re constantly exposed to theories with little utility, people with strong opinions but no data, ways of working that don’t work, and a host of other situations where a heavy dose of critical thinking is required.

We need to be skeptical — even of plausible-sounding ideas — and trained to separate fact from opinion, truth from assumption. Thinking critically about information, communication, concepts, and methods can help us gain clarity, understanding, and better decision-making.

When I recruit for my teams, two skills are always top of the list: critical thinking and strong communication. Why? Because I’ve yet to meet a critical thinker who isn’t a good communicator. Painfully difficult to work with otherwise.

Here’s how I approach critical thinking in the workplace, with three go-to questions and the robust Phoenix Checklist, developed by the CIA.

Critical Thinkers Can Be Annoying — in a Good Way

Critical thinking is, by nature, a little irritating — but in a “good for business” way.

It’s about getting to the heart of a matter, understanding principles, and uncovering truth. Asking questions is the most visible expression of critical thinking, but developing the skill within our own minds is just as important.

When we cultivate this skill, we gain control over what influences us, what we choose to believe, and how we act. We’re no longer swayed by agendas or shallow reasoning or plausible sounding ideas. Strong opinions no longer influence us and our logic, and we can understand the world more clearly.

Yes, critical thinkers can be annoying — because they ask deep, clarifying questions. Questions that challenge assumptions, poke holes in theories, and force people to think harder. But good questions keep a business alive. Too many questions though are a form of sabotage!

My Three Everyday Critical Thinking Questions

Here are my three most-used questions in the workplace:

1. What problem are we trying to solve?

This is a power question. It demands clarity of purpose. Ask it in meetings, before projects, or when tackling executive requests. If you can’t clearly explain the problem — or the opportunity — you’re pursuing, pause. Gather more data. Gain insight.

I’ve seen billion-pound transformations launched without a clear problem or target. Chaos ensues. I’ve seen digital products built that nobody uses because the problem wasn’t clear. Always start by clarifying the problem — and its twin: the opportunity you’re opening.

👉 See this post on asking this simple but powerful question

2. Is that always true?

Apply this whenever someone makes an absolute statement: “Never,” “Always,” or “Everyone knows that…”

Ask yourself:

• Is it always true?
• Are there situations when it’s not true?
• Could the opposite also be valid?

For example, early in my career, someone said, “All standup meetings must have participants standing.” Not true — remote work, broken legs, or accessibility needs proved exceptions.

This question is particularly useful when people promote dogmatic approaches: “This framework is the only way to achieve results.” Usually, other approaches also work, depending on context. Asking “Is that always true?” exposes hidden assumptions and prevents flawed reasoning from taking root.

3. If it’s always true, is the opposite always false?

This is a natural extension of the previous question. Often, multiple perspectives can be true simultaneously, depending on context. Critical thinking helps identify these nuances, avoiding rigid, binary thinking that limits innovation.

Why Critical Questions Matter

• Prevent people spending millions on projects with no clear problem or value.
• Counter misinformation and “watermelon reporting” (green outside, red inside).
• Challenge subjective opinions and expose flawed assumptions.

As Edward Deming said:

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

Critical thinking thrives when paired with good data and the courage to question assumptions.

The Phoenix Checklist

For a deeper approach, I use the Phoenix Checklist, a robust framework of critical questions developed by the CIA. I keep it in my digital notes and use it frequently to challenge assumptions, clarify thinking, and uncover truth.

The Problem

• Why is it necessary to solve the problem?
• What benefits will you receive by solving the problem?
• What is the unknown?
• What don’t you yet understand?
• What information do you have?
• What isn’t the problem?
• Is the information sufficient, insufficient, redundant, or contradictory?
• Should you draw a diagram or figure of the problem?
• 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?
• What are the constants of the problem?
• Have you seen this problem before, or in a slightly different form?
• Do you know a related problem?
• If you find a related problem already solved, can you use it or its method?
• Can you restate your problem—more generally or more specifically?
• 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, or just part of it?
• 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 and accounted for all essential notions?
• 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 techniques and results can you see or try?
• What have others done?
• Can you intuit the solution?
• Can you check the result?
• What should be done, how, where, when, and by whom?
• What do you need to do now?
• Can you use this problem to solve another problem?
• What is unique about this problem?
• What milestones mark progress?
• How will you know when you’re successful?

Using Critical Thinking Every Day

Critical thinking is a muscle that needs regular exercise. These questions, from the three core ones to the Phoenix Checklist, are tools to:

• Separate fact from opinion
• Make better business decisions
• Challenge dogma and assumptions
• Promote clarity and actionable insight

When teams embrace critical thinking, they avoid wasted effort, prevent costly errors, and make decisions based on evidence, not just opinion.

Final Thoughts

Critical thinking is essential in today’s workplace. It’s not about being contrarian or difficult — it’s about uncovering truth, clarifying purpose, and enabling better outcomes.

Combine critical thinking with strong communication, and you create teams that are not only smart, but effective, collaborative, and aligned. Questions like “What problem are we solving?” or “Is that always true?” are not just rhetorical — they’re tools to keep a business alive and thriving.

The Phoenix Checklist provides a comprehensive list to systematically think through problems and solutions. If used consistently, it transforms decision-making from reactive to informed, strategic, and accountable.

Critical thinkers might be annoying — but in the best way possible: they make businesses, teams, and decisions better.