Asking the Right Questions is a Superpower: Get as Curious About Your Career as You Are About Your Clients

Before my career in sales and business development, I was a reporter. I worked at a small paper in rural Washington State and my editor told me that you can ask most people anything and they will answer you. I had a press card and a small notebook and, except for public officials, people did answer any question I put to them.

Asking questions is a superpower. So, why don’t we all ask more questions? Or, if we use questions skillfully at work, why don’t we employ them as effectively to get curious about our professional growth and development?

Most of you already know how to ask the right questions at work. You can’t build a bid or proposal, or close a deal, without asking skillful questions. But have you thought about the value of asking questions about your career path? Recently, I presented at the APMP Women’s Virtual Summit about mapping your career as you age, and how important it is to have a plan for the future. Questions can help you build that plan.

First, ask questions of yourself. Some of us set a career goal in the past but don’t check in on how valid it still is and if we’re on the right path to achieve it.

Step away from the day-to-day and take some serious consideration:

• Is this work satisfying to me, or can I see a path to a time where it will be reasonably fulfilling?
• Is this what I want to be doing five years from now?
• Does this job give me the time and money to support the life I want? Do I have enough time with my family?
• Can I save for retirement or other long term financial goals?
• Do I have relative psychological safety at work and am I able to show up authentically? Do I enjoy some of the people I work with every day?
• Do I need meaning in my work and does this job provide it?

You may be surprised at the answers. Is your goal clearer? Has it changed? Hopefully, your curiosity will guide you to the career moves necessary to get to the kind of work that will serve you best. If you find that your job or current career track isn’t a fit, honor that and commit to more in-depth examination.

Next, make sure you have a clear idea of your strengths and weaknesses. You’d be surprised at how many of us carry old, outdated notions of our abilities or limitations. Understanding your gifts and challenges accurately is necessary to create the right path for growth.

Don’t just be curious about your weaknesses or opportunities for development. You also need to have clarity about your talents.

I’ve had many clients underestimate their strengths, assuming everyone could do something that came relatively easily to them. But, in many cases, what came easily to them was a unique talent. If we don’t understand our value and worth to an organization, we might not ask for that raise or promotion or consider leveraging specialty skills to move to a job that is more rewarding to us.

Who do you ask about your abilities? Some organizations prioritize reviews and feedback, others do not. You may need other input if your company is perfunctory about reviews. Ask trusted peers, mentors or friends to give you honest feedback about your strengths as well as opportunities for growth. Here are some sample questions:

• What am I best at? (It’s always good to start with something positive.)
• Where could I build skills?
• Is there a story or example of how I work that seems representative of me as a leader or colleague?
• If you had a magic wand and could change one thing about me, what would it be?

Now, you understand your goals, the strengths you can leverage and any skills you need to build. If your current workplace is a good fit for you, the next step is to ask questions of your organization about your growth there so you can see what your workplace can do to move you towards your goals

• Do they have a plan mapped out for you? How will they support you? Do they provide training, conferences, coaching or tuition subsidies for ongoing education?
• Do you have a clear understanding of what milestones you need to pass to get to the next promotion?
• Does your organization provide the support and skills-building to move you to where you want to be?

Most of us exercise or pay attention to our health at some point every week. I’d like to invite you to spend at least 30 minutes a month on the health of your career. Use these questions of yourself, your organization, and a trusted mentor or coach to boost your career using the superpower of asking the right questions.

Stephanie Peirolo is a board-certified executive coach who works with creative leaders. She writes about work at The Consigliera Papers on Substack, and has a podcast with Eugene S. Robinson called The Bad Boss Brief. Her book “The Saint and the Drunk; Building a Practice of Intentional Decision Making” will be published in the spring of 2025. Contact Stephanie at [email protected]