The Project Manager’s Guide to Critical Thinking Skills

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Published in Project management on 19/07/2021, last updated 26/10/2023.

Remember playing the game Clue as a kid? You’d collect evidence, analyze the possibilities, and come to your own conclusions based on what you knew (and what you didn’t). As a project manager, the skills you developed playing games like Clue are extremely useful. The acting gatekeeper for your team, you’re used to evaluating information and making decisions to benefit your department and the business as a whole. Whether you’re a seasoned project manager or just learning the ropes, knowing how to fine-tune your critical thinking skills will come in handy every single day.

Continue reading to learn: 

• A definition of critical thinking
• The six critical skills project managers need
• Why critical thinking skills are crucial for project managers
• How to work your critical thinking muscles
• Effective critical thinking techniques

Let’s get critical. 

What is critical thinking?

Ask five different people what critical thinking means and you’ll probably get five different answers. But, generally speaking, critical thinking refers to intellectual tactics used to observe and analyze information to draw better conclusions. A key factor in critical thinking is looking beyond the surface of an idea, a concept, or a piece of information. It involves asking questions — to yourself or others — to go deeper and draw better conclusions.

Critical thinking can be used by anyone, in any role, to make their job easier. You can find new insights, optimize an inefficient process, and get projects done faster. Developing your critical thinking means building habits that follow you throughout your career.

Here’s a breakdown of crucial critical thinking skills for project managers — or any other role.

6 critical thinking skills for project managers

Skill #1: Observation

Critical thinking skills starts with being more aware of what’s going on. Working on an important project? Being observant might mean keeping a close eye on comments from collaborators, or just paying better attention during meetings with your data team. Becoming a more observant person means you can identify problems others miss or pick up on context clues that help you solve problems down the road.

Skill #2: Analysis

Spotting problems, clues, and that one important comment in a Slack thread is just the beginning. If observation is how you bring in more information, analysis is how you determine what you’re going to do with it. Having an analytical approach to your problems means knowing what information you have available, knowing how relevant each piece is to the problem at hand, and being able to ask better questions. 

Skill #3: Identifying bias

This critical thinking skill ties in closely with analysis but is important enough to be its own skill. Bias is inherent in everything we do, from collecting data to creating content and solving problems. For instance, because this blog post is being written by a marketer, it might use different examples than a writer from a more technical team. You can spot a bias by asking yourself questions, like “are there elements of this person’s experience or perspective that might be affecting what they’re saying?” Bias can affect every role in an organization.

Skill #4: Inference

This is a fancy term for drawing better conclusions. This crucial critical thinking skill helps you make better use of the information you collect, the questions you ask, and the potential problems you spot. Think of everything you might have done so far as putting ingredients in a stew. You can have the best ingredients in the world, but if you leave the pot on too long, you’ll end up with something closer to charcoal than stew.

One of the quickest ways to improve your inference skills is, ironically, by slowing down. Instead of blurting out the first conclusion that comes to mind, start with a few educated guesses, and compare them to each other. Which one makes the most sense? Which is weakest?

Skill #5: Problem-solving

If inference is how you come to better conclusions, problem-solving is how you put them into action. This critical thinking skill encompasses the tactics and strategies you use to take something that looks good on paper and make it great in practice. Problem-solving includes planning how you’ll solve a problem, but also reacting to hurdles along the way and staying flexible. A great way to improve your problem-solving skills is asking yourself “is this still the best way to solve the problem?” at every stage of your plan. Sometimes, people can get set in their ways, meaning they stick to an ineffective solution long after they should have pivoted to something else.

Skill #6: Curiosity

This is less a skill than it is a characteristic every critical thinker should work to develop. Every other critical thinking skill is helped by broadening having access to more information and more knowledge. For instance, you can be the most observant person in the world, but you’d still struggle to pick out all the problems in a presentation from the data team if you weren’t at least a little familiar with data analysis. Beyond expertise in specific fields, critical thinking — and thinking in general — is easier when you have a breadth of knowledge and experiences to draw from. You can find links that others would miss and learn to think in different ways. Read more books, listen to more podcasts, and approach the world at large with more curiosity.

Why do project managers need critical thinking skills? 

When people hear the phrase ‘critical thinking’, they often picture a negative person. Being a critical thinker doesn’t mean you have a bad attitude or that you aren’t a team player. It’s quite the opposite. 

Critical thinking means questioning processes, projects, and even core business practices that are widely accepted as given. Not to tear them down, but to improve them for the benefit of the entire team. 

The Project Management Institute (PMI) outlines how important this skill is: 

“Corporate leaders have put critical thinking at the top of the list of essential competencies needed by their workers to understand these challenges, explore opportunities, and make good decisions in this new competitive environment.” 

When used in the context of project management, effective critical thinking can: 

• Encourage deeper, more  productive discussions
• Facilitate open communication between team members 
• Resolve issues between team members and stakeholders more quickly
• Develop better solutions to problems 
• Reduce stress throughout a project 
• Prevent repetitive issues
• Achieve better results faster 

Now that you know why critical thinking skills are priority for project managers, it’s time to find out how you can improve yours.

How project managers can develop better critical thinking skills 

There’s one core principle that will guide your critical thinking: question everything. Project managers can’t just approve all requests that come in from stakeholders across the organization — unless they want a stressed-out, overworked team.

A good project manager knows how to prioritize projects according to the business’ overall needs and goals. With every request that comes in, you need to be prepared to evaluate the project’s impact on the business, the necessity of the project, and the why. Building this process — this instinct — into your daily work is how you build and strengthen your critical thinking skills.

For every potential project, consider: 

• Why is this important right now? While most stakeholders will say their project is urgent, you need to find out exactly how true this is. Perhaps the project could be scheduled for a later date that works better for your team’s schedule. 
• Why does my team need to be involved? For example, if you manage the creative team and a request for a sales presentation comes in, figure out exactly what your team will need to do.
• Why is my team’s time better spent on this project than other projects? Does this project contribute more to the business than other work your team could be doing? 

Those are three important questions to ask yourself, but what about the questions you ask others?

When a new project lands in your inbox, you need to know what to ask of the sender and how to delicately frame those questions. There are a few question formats that work especially well for this stage of the project. These include:

• ‘tell me more’ questions (eg. Tell me more about what will be required from each member of my team)
• ‘help me understand’ questions (eg. Help me understand why this project is urgent)
• ‘can you give me an example’ questions (eg. Can you give me an example of the types of results you’re looking for here?). 

These questions allow you to get a better understanding of the project and make sure it’s a good fit for your team. They’re also usually well-received by whoever initiated the project.

Prioritization means making tough calls, and project managers need to be ready and equipped to do so. You can’t be afraid to say no when the project doesn’t make sense from a timing or business standpoint. However, you will also need to be ready to explain the reasoning behind your “no”. The following techniques will help you feel confident in your decisions and authority as a project manager. 

Critical thinking techniques for project managers 

Critical thinking skills are one thing, but when evaluating the priority of a new project, there are critical thinking techniques you can put into practice to boost results and team morale. 

1. Avoid making or accepting assumptions 
2. Identify potential issues (and their consequences) from the start
3. Use the Five Whys to find the root of problems 

Let’s dive into these a little bit more. 

1. Avoid assumptions 

You know what they say about assuming things. When you make assumptions as a project manager, you’re missing out on and ignoring key information that could make or break your project. You can have the best critical thinking skills in the office, but making the wrong assumption can undo all your hard work.

A big part of critical thinking is digging into reasoning and probing for evidence rather than drawing your own immediate conclusions. When you’re pitched a new project — and during the course of the entire project — question any preconceived notions (yours or theirs). Ensure you’re given concrete evidence for the viability of the project, and look for any holes in the process or strategy that could impact your team. 

When challenging assumptions, consider the following questions: 

• Am I assuming all members of this project have all the information they need to complete their tasks?
• What assumptions am I making about each team members’ skill sets? 
• Am I making assumptions about each team member’s time and availability? 
• What are some possible issues that may arise with this project? How can I work backwards and challenge any assumptions in order to avoid these issues? 
• What assumptions have I made about the stakeholder or project creator? What do they need to know? 

Never take anything for granted. When your job is to facilitate and manage expectations, it’s important that you’re questioning and challenging your own assumptions — and those of team members and stakeholders — at all stages of the process. 

2. Consider potential issues 

When you’re questioning assumptions, you’re also working towards another big part of your job: risk management. By proactively questioning what could go wrong, you can prepare for any issues that might arise during the course of the project. Not only that, but you can consider the implications and consequences of when things go awry. 

Consider a cause and effect approach with hypothetical — but realistic — issues. Give yourself an hour to write down any possible issues that could arise with the project, along with a list of consequences associated with each one. For example: 

• Problem: The video editor won’t have enough time to deliver the final file. 
• Consequence: The rest of the project will be held up. Costs will increase and we could miss the deadline.  

In a perfect world, project managers wouldn’t face any problems and all projects would be smooth sailing. Since that’s unfortunately not the case, here are some helpful tools you can use to avoid the escalation of issues — as well as repeating roadblocks with future projects.

3. Use the Five Whys

In addition to the “why” questions outlined above, a proven project management technique called “The Five Whys” can help you explore the true cause or causes of any problem. 

Here’s how ProjectManagement.com explains it: 

“5 Whys is an iterative elicitation method used to explore cause-and-effect relationships underlying a particular problem. The primary goal of the technique is to determine the root cause of a defect or problem by repeating the question ‘Why?’. Each answer forms the basis of the next question.” 

To complete The Five Whys, you simply repeat the question “why?” five times until you come to the root of the problem. Each answer is understood to be a “contributing cause” that impacts the final result. 

For example: 

1. Why did we miss our deadline?
   • Because multiple teams weren’t able to complete their tasks on time (contributing cause). 
2. Why weren’t these teams able to complete their tasks on time?
   • Because their time wasn’t prioritized properly (contributing cause). 
3. Why wasn’t their time prioritized properly?
   • Because multiple last-minute projects were assigned (contributing cause). 
4. Why were multiple last-minute projects assigned?
   • Because other stakeholders didn’t understand the prioritization and project assignment process (contributing cause). 
5. Why don’t other teams understand these processes?
   • Because they haven’t been properly trained or given the necessary information (root cause). 

Once you get to the root of the problem, you can take action to ensure these issues are minimized or avoided in the future. 

For project managers, sometimes taking a moment to just stop and consider all of the possibilities, consequences, and information can make all the difference between a well-thought-out decision and a future regret. Developing and exercising your critical thinking skills is a surefire way to drive positive business results.