Critical and Strategic Thinking for Force Multipliers

Executive Assistants and Chiefs of Staff can make an even bigger impact on their leaders and organization when they constantly level up their thinking skills. Learning to make decisions, anticipate issues, solve problems, communicate effectively, ask powerful questions, and think critically and strategically are all important parts of being a great Force Multiplier and strategic partner.

Critical thinking and strategic thinking are two of those terms that career coaches, executive trainers, business podcasts, leaders, and professionals throw around as important skills for a successful career. I’m guilty of it too. Recently, I was conducting a training and realized that as much emphasis as I put on thinking strategically and critically, I hadn’t taken the time to define what that actually means and why it’s important.

So here goes.

What is Critical Thinking?

Much of our thinking is biased, and we often lack most of the information we need to think critically about a topic. But if the quality of our life is based on the way we think about the world, about ourselves, and about others, then wouldn’t we want more information and different perspectives in order to make the best choices? If our thinking is subpar, then so too will be the quality of our lives. Conversely, thinking big and thinking differently will enhance our decisions and ultimately our lives. That’s where critical thinking comes in.

Critical thinking is the way in which to think about anything—a problem, a new topic, an article—where the thinker is improving the quality of their thinking by analyzing, assessing, and breaking down the issue. Critical thinking is self-driven and aims to explore topics from different angles. The thinker questions their biases and previously held beliefs, conducts self-inquiry, and gathers additional information if needed.

Here’s an example: Your Executive has just presented you with a scheduling and logistical nightmare challenge. You immediately dive in and start making changes. That’s not a bad approach, but there is a better way. Do you take a step back and look at the big picture? What is your Executive’s main objective here? Are you clear on why these changes are even necessary? Do you touch base with their spouse or Chief of Staff to gather more information? How will these changes affect other projects or meetings that are going on? Is there a way to make it all work? Is there more than one option to consider here?

How to Think Critically

Critical thinking is essential when solving problems, no matter how big or small. What you decide could impact your Executive and potentially have a ripple effect in their life or throughout the organization. If you don’t look at the issue from multiple angles, you may not fully understand the impact of your decision.

The best part is, you can improve your critical thinking. This Inc.com article outlines 7 mental exercises that will make you a better critical thinker:

  1. Express yourself in multiple mediums. Work through your thinking in writing, verbally, or via a slide deck. Being able to clearly communicate your thinking helps build this skill.
  2. Talk to a 6 year old. If you can explain your thinking to a 6 year old, then it’s an indication that you have a full understanding of the issue.
  3. Understand and challenge your biases. Constantly question your assumptions and beliefs.
  4. Work backwards. Understand the end goal or product and think through how you or the team came to that conclusion.
  5. Ask other people to explain their thought process. This is a great way to learn how others think, gives you the opportunity to ask questions, and ultimately strengthens your own critical thinking in the process.
  6. Expose yourself to new content and new creators. Your output (thinking, creating, questions) is only as good as the quality of your input. Challenge yourself to read or listen to content that challenges your previous held beliefs or argues the other side of an issue.
  7. Experiment with brain teasers and ethical dilemmas. Pose hypothetical problems to yourself and think through how you might solve them.

What is Strategic Thinking?

Strategic thinking is defined as an individual’s capacity for thinking conceptually, imaginatively, systematically, and opportunistically with regard to the attainment of success in the future.

Why is this important? Strategic thinking allows you to have a broad view of a situation, while also allowing you to zoom in on the details when necessary. It means you are both thinking abstractly and using concrete examples to communicate and make decisions. Strategic thinking means you are embracing alternatives and uncertainties, and thinking in bets to make effective decisions in order to achieve an over-arching goal.

Here’s an example: You are mapping out the year ahead with the Executive Assistant to the CEO. There are regular internal meetings that need to be accounted for. However, your company is going public this year, and there will be a plethora of additional obligations, ranging from fundraising trips, public appearances, interviews, international travel, as well as her son’s wedding mid-year. In addition, there are 3 other major initiatives on the Executive’s agenda that will require her time and energy over the next 18-24 months.

Understanding the CEO’s primary objective here is key. From there, you’re able to look at the big picture and start organizing, communicating, and delegating projects and plans, while mapping out the best use of your CEO’s time over the next year. You have all the pieces of information, you’ve thought through them critically (see above) and now it’s time to put the puzzle together to achieve the goal.

How to Think Strategically

Strategic thinking allows you to create a plan of action designed to optimize results.

Just like critical thinking, strategic thinking can be learned. The Harvard Business Review offers four different ways for improving your strategic thinking:

  1. Know—Observe & Seek Trends
  2. Think—Ask the Tough Questions
  3. Speak—Sound Strategic
  4. Act—Make Time for Thinking & Embrace Conflict

The Main Differences Between Critical and Strategic Thinking

Critical thinking is usually applied to a specific topic or problem happening in the present. It could be a discussion around hiring talent, time management, a morale issue, or risk mitigation.

Strategic thinking uses a variety of thinking frameworks and mental models in order to achieve a goal in the future. This might look like creating a hiring plan for the next two years, planning board meetings and retreats for the year head, creating an employee appreciation program, or implementing a new system for making decisions across the organization.

When used together, critical thinking and strategic thinking are a recipe for better decision-making and better leadership.

Critical and Strategic Thinking for Force Multipliers

Being a Force Multiplier means utilizing (and demonstrating) your critical and strategic thinking skills regularly in your role. You do this by bringing a distinct viewpoint to the table, challenging other people’s perspectives and sharing your own, asking powerful questions, having the courage to voice your ideas, your strategic insights, or critical observations, and then being able to take those ideas and bring about change. A tall order? Perhaps. But that’s what leadership is!

While this quote is from an unknown source, it sums up a lot: “Our job is not to make up anybody’s mind, but to open minds and to make the agony of the decision-making so intense you can only escape by thinking.” I think that is what great leaders and great Force Multipliers do. What do you think?

Original post shared on October 21, 2021. Updated for 2024.

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