Thinking Critically on the Career Path: Why it matters & how to do it (and do it well)

Critical Thinking is a semi-elusive skill you’re supposed to have down pat at some point in college (and if you’re lucky, in high school). It’s in my rubric for grading papers, within the title of the occasional assignment (Critical Thinking Papers when I can’t think of a catchy alternative) and sprinkled liberally throughout my syllabi and course materials. For the most part, students catch on and begin to think critically about the world around them which is an academic way to suggest they step outside their shadows to notice that they are not, as many mistakenly think, terminally unique.

A working definition of critical thinking is the strategic engagement of one’s cognitive skills to reach a specific outcome. That’s the digest version; as a Sociologist invested in strategic outcomes, I would add that critical investment has to include understanding your audience so that your ideas will be heard, so that you will be understood, and so that you project that you’re interested enough in something to engage in a dialogue even (and especially) when you disagree about something. If you know nothing about a topic, that’s even better because thinking critically about what you don’t know enables you to open your mind to learn.

Diving deeper, critical thinking is, in its purest form, intentional. It’s the sort of thinking that takes you from “Yeah, I liked that book, it was good,” to “What I liked so much about Waldman’s A Really Good Day is that it resonated with me, as I also suffer from debilitating mood swings. The book made me step back and look at how my mood impacts my daily life and those around me.” (BTW, I highly recommend her book, I just finished it, and it was great. I just told you why.)

Applying Critical Thinking Skills

Wherever you on the career spectrum (new to the job search, midcareer, third career, unemployed, underemployed, post-academic, running a small biz, etc.), always apply critical thinking skills to your endeavors. In doing so, you’re showing up fully and with intention. This is how you stay alert and accountable. And it’s how you can develop your documents and measure your social interactions (online and in person) when it counts.

My clients work on this by applying the Who, What, Where, When, Why, and How method. Who is involved? What is at stake? Where do you need to be to best respond/write/think? Why do you want to execute this move? Why are you the best person for this job (or client)? How will you plan out your milestones to reach the goal you’ve set?

For example, when most of us apply for a job, we focus on the job title, paying little attention to the actual description. It’s also not uncommon to skip to the minimum qualifications section, decide you meet those qualifications, and hit “send” to apply. I encourage you instead to parse the sentences in job calls and really, anything you need to respond to on your career path. That includes evaluative materials, your résumé as you update over time (these are, I like to say, living documents), and your onboarding materials for clients if you use these in your small business. Any document used along the career path (really, any and all) are items you want to deeply understand — particularly if you’re writing them — so that you can always be at your best and always be present. This is thinking critically.

The key to having a critical thinking approach to career development is to be fully present in the process. Many of us keep a personal distance to our careers because we assume that to affect an appropriate live-work balance, we must keep our personal lives and our work lives separate. While I tend to agree to some extent, what can also happen is that one or the other takes a backseat and becomes an afterthought. But you needn’t discount or dismiss one to uphold the other. To be critically invested in your work life simply means you’re paying attention to the cultural and personal nuances of your actions and the actions of those around you.

Be Your Own Cheerleader

Another key ingredient to a critical thinking approach to career development is to remember you’re often in this endeavor alone. You might have a coach, partner, coworker, or pal(s) that are rallying for your cause but looking for a job, negotiating for a raise, starting your own business, or moving into a new realm of labor is often a lonely venture.

If critical thinking is intentional and goal-directed, then think about how that applies to you, inwardly, as you make decisions in your career. Because critical thinking is rooted in problem-solving, making decisions, and calculating possible outcomes, you can use these skills in just about any setting (critical thinking: it’s not just for college!). When we engage in the process of thinking critically, we are precise about how we evaluate outcomes, how we consider decisions before we make them, and how we can best approach a challenge.

You do have to rally for yourself, avoid seeking too much advice, and learn to depend on yourself to make decisions. The more you learn to come to your own conclusions, face challenges for which you’ve designed the approach, and create documents for self-representation, the more confidence you will build. Sure, hire a career coach to guide you, but any career coach worth her salt will get you to do the work as she stands on the sidelines and watches your (often unparalleled and surprising — to you) success.

Tips from a Career Development Strategist

I’m an academic by trade, and it’s a radical pedagogical approach to coaching that sets me apart from other career coaches. It doesn’t make me better; it makes me different. No, I don’t have clients read scholarly journal articles or write essays. I use my methods of teaching, my teaching philosophy (which is rooted in radical thought — which simply means stepping off the expected path) to get people to slow down and think deeply about the decisions they make along their multi-varied career paths.

Here are some of the ways I get my clients thinking critically about their choices:

· Understand the language you’re using. This seems basic but if you want to stand apart from every other schmo on the block, use easy to understand and thoughtful terminology right out the gate.

· Cultivate a habit of advocating your ideas, how they work, for whom they work, and why they work. It’s one thing to have a good idea but quite another to understand the core of that good idea. Don’t just present it, explain it.

· Avoid ambiguity in your writing. Always.

· Get clear on your expectations, in whatever you’re doing. How do those expectations match up with the task or challenge at hand? How do your expectations present your capability?

· What skills, knowledge, and interests are you bringing to the table and how do they match up with your desired outcomes (and expectations, as above)?

· Always understand the content with which you’re engaging. For example, if you’re applying for a raise, understand the history of other people successfully getting raises. Do more than just say why you deserve one.

· Always have a backup plan. For everything. Understand circumstances that might call for said backup plan so that your backup plan will make sense.

· Understand what’s at stake and assess risk in everything you do. It’s worth taking risks, but you have to know their value. What’s the cost-benefit analysis?

· Develop a habit of being strategic in your decisions. Go back to the Who, What, Why, When, How.

· Finally, assess your decisions. What worked? What didn’t work? Why? This is where you might consider getting feedback from others, say, if you plan to do any Informational Interviews.

Make a Toolkit

Give yourself some feedback for each step. So, you do this after you’ve selected and reviewed job announcement after you’ve drafted (and polished) your résumé and cover letter, and after you’ve jotted down some questions to ask in an interview (pro-tip: always questions prepared when you go for an interview). The feedback stage is where you also need some critical thinking skills because when you are thinking critically about your material and your actions, you’re being self-reflective. Self-reflection at its core is the skill you need to effectively grow both personally and professionally (and I assume these to be intertwined, always).

Being thoughtful about your decisions is how you begin to develop a toolkit for yourself of best practices in your professional life. Ask yourself:

· What works? Why?

· What doesn’t work? Why?

· What did I do well?

· What am I not yet able to do?

· Is that a skill I need to develop? How will I do it?

· How does my work compare with what I’ve done previously? How can I measure that?

· And the last question: How can I do better?

Your toolkit will build over time and can be applied during and after your job search. The point is to evolve, professionally. Be more thoughtful. Invest in Yourself. See, grasp, and take hold of innovations you have to offer.

When you focus strategically, and it becomes a habit, something cool happens that I like to call, Accidental Reflection. You’ve likely experienced this; some people call it an “Ah-Ha Moment.” You realize something that you didn’t notice before, but this is a bit more special because you’ve reached the sort of milestone that is self-developed. You’ve trained yourself to think more deeply.

In the end…

This method can freak people out but don’t be daunted. Critical thinking can scale up any experience because you are training yourself to habitually refuse to take anything at face value and you’re also shoring up your confidence. Applying critical thinking to everything that you do in your professional life will set you apart from other people in (often, surprisingly) unexpected ways.

So go forth and think, reflect, question, and assess. I promise you, it works, and it’s the best personal and professional development skill you can build. For free.