Ask these 5 powerful questions to direct your next career move 

Indira Gandhi couldn’t have been more right when she said, “The power to question is the basis of all human progress.” As India’s first female prime minister, her focus was at a societal level, but the message holds on a personal level, too. Bringing this mindset—plus a flexible, repeatable process—to career planning empowers professionals of all types to make great career decisions, no matter what life throws their way.  



The need for such a model is greater than ever. Gone are the days of marching up the same career ladder as everyone around you. Professionals today know that no path is a sure thing—and their career paths show it. Indeed, the average person spends less than three years in a given job .  



Professionals also know that life experiences and events will occasionally force them to reevaluate all their choices. Life experiences such as a global pandemic, for example. 



And they know that the top of the proverbial career ladder may not be the meaningful, satisfying pinnacle they once thought. 



Creating your career path 



The career ladder doesn’t work because we are not monolithic groups of attorneys, physicians, accountants, designers, coders, and [insert any professional here]. That ladder doesn’t flex to account for what matters most to you, whether that be building your own business, building a nest egg for those you love, or raising a family. 



That’s why I created what I call my Hip Pocket Questions. These questions are designed to enable people to think differently about career decisions, ground them in their personal priorities, and create a bespoke ladder designed just for them.  



Five questions to guide your career decision-making 



What matters most to you, personally and professionally, at this age and stage of your life? 



This first step is really about knowing yourself. And start to think differently about your career choices. There are often multiple answers to this question, and there are no wrong answers.  



Your responses may involve your career, but they could also be more personal. Some answers I have heard include: 




Picking up my children from school every day 



Having a regular date night with my significant other 



Getting a promotion at work 



Increasing my overall income 



Building a new business 



Having time to garden 



Reconnecting with friends 



Writing a book 




Remember, there are no wrong answers. And there is no correct ratio of work to personal items. There are only your answers. The thing that most often surprises people when I ask them to do this exercise is that their most important items are often personal rather than professional. But it depends on the season or stage of life where you find yourself. The way you answer this question will serve as a touchstone for your career decisions moving forward, not to mention giving you a new set of metrics you can use to measure career success.  



Who are the people in your life with a stake in the decisions you make, and what matters most to them? 



Imagine you get a job offer that requires you to move to another state—or around the world. Such a decision, exciting though it may be, will have a significant impact on certain people in your life. A spouse and other family members are prime examples, but these are not the only stakeholders to consider. Anyone who will be affected by your career choices is potentially a stakeholder, and I have even known people to list pets as stakeholders. And they may be affected by a major move, so why not? 



Make your list, then revisit the first question, but with a twist. What matters most to your key stakeholders? Ultimately, the goal is to think about how their wants, needs, and goals might shape your decisions. When it’s right and if you choose, you can allow them to weigh in and consider their priorities to potentially influence your plans. If you do ask them to make their list, keep your lists private until you have both completed them, and only then discuss them between or among you. 



What do my organization and its leadership prioritize, and what are their stated and unstated goals? 



This question is about alignment, and it will be especially helpful when you think about whether you are ready to look for a new professional home. If you’re not sure how to figure this out, look to the company website to start. Mission or values statements may be a helpful starting place, though you’ll want to consider how faithfully that mission is being met. 



An example may help. Some organizations are characterized by an always-on culture. This may be because leadership is heavily motivated by the bottom line, so much so that vacations are discouraged or perhaps people are expected to be available by phone 24-7. This may work great for some people, but it’s not for everyone. Clarifying this organizational priority could help someone who places a premium on time with family to decide on their next move.  



If you are between jobs, try applying this question to prospective employers as you work through your job search. 



What is the alignment between my answers to the first three questions in this process?



Now, look back on your answers so far. What matters to you, what matters to your stakeholders, and what matters to the organization you work for (or hope to work for)? Where do values and priorities line up? If the ability to travel matters to you and your spouse, and you have clarified that your company’s global expansion is likely to keep you on the road with the ability to bring your spouse, you may identify some nice alignment.  



Conversely, if what matters most to you and your children is time with family, and you travel around the world working for that same expanding company, you may see misalignment.   



The way you answer this question will determine the fifth question. 



How do you want to learn and grow from a place where you are currently thriving and there are no misalignments?   



Or



What are you ready, willing, and able to do about any misalignments you have identified? 



Identifying a high degree of alignment doesn’t mean you should just set these questions aside and revisit them when a problem arises. It means you may not need to pursue a different opportunity to thrive, but you’ll still want to ensure you are growing in a healthy direction and striving to bring more of what matters most to you into your life. Consider whether some additional training or a stretch assignment might fit the bill. Building a new skill or becoming visible as an expert on a particular topic may help you prepare for the next step on your bespoke career ladder. 



Identifying misalignment is a bit different. This may mean it’s time for a change, like a new job. But not always. Sometimes we stay in jobs where we feel misalignment for good reasons. For example, if you need another year to become vested in your retirement plan before starting your own business, you may be unwilling to do anything about any misalignment you have detected, at least for the next 12 months.  



What’s important here is developing a mindset of intentionality. Often, we feel like we don’t have choices, but the truth is we do. Staying in a job you don’t love to become vested in your retirement plan is a choice, and may very well be a good one. It may also feel better when framed around what matters most to you and if your healthy retirement will make that possible. 



The art of asking over a lifetime 



I call these the “hip pocket questions” because they are best used regularly—at least annually, potentially quarterly, and undoubtedly whenever the unexpected happens. Curveballs of life—the good and not-so-good—often shift our priorities and clarify misalignment.   



There are lots of ways to approach career planning, but I like this one because a one-size-fits-all approach won’t work for many, if any of us. And we are long overdue for a career model that empowers people to create a career that works for them and their priorities. Only you know what matters most to you. I can’t answer that for you, but I can ask the question that helps you find the answer and run with it.