From AI-powered job platforms to professional career coaches, there are countless online resources you can use to access career advice. Yet, nothing beats getting insight from the people closest to you, especially if you have fond memories of talking, laughing, and learning with them over the years.
It makes sense that a plurality of women (25 percent) prefer to get career advice through conversations with friends and family, and 44 percent of women regularly talk to their friends about their jobs. In addition to providing emotional support and a sense of belonging, those closest to us can help us reflect, plan next steps, and carve out a more thoughtful career path.
This is your guide to doing just that. By speaking with your closest confidants about their career highs and lows, you can enhance your career development while deepening your relationships. These 15 questions will help you grow with intention.
Questions for unexpected career insights
1. Tell me about a moment in your career when things took an unexpected turn.
Some of your most pivotal career moments are those you don’t expect—the same may be true for your family and friends. Ask your loved ones about times when they had to adapt to something new or unexpected and how it affected their careers. You may find that their accounts of being laid off, having to take a career break, or starting a business can inspire you to embrace change in your own career.
2. What’s something you thought you knew about the workplace that actually turned out to be different?
You may already know about common rules and norms at work, like being punctual and completing work on time, but there are unwritten rules, too. For example, most people won’t tell you how important self-promotion is, but the people closest to you can advise on why and how you need to promote your achievements at work, along with other things they thought they knew about before gaining more experience.
3. Is there a skill or strength you’ve ended up using a lot that you never thought would be important?
Jobs are often nuanced, with various companies, industries, and sectors all interpreting them differently. As a result, you may end up using skills you didn’t expect to use. Hearing from your family and friends about skills and strengths they’ve unexpectedly used at work can help build your sense of resiliency and empower you to think outside the box when considering new career opportunities.
4. Have you ever stumbled into a job that completely changed your path?
Whether you come across a great job opportunity or land something that leaves much to be desired, you gain useful information about what you like (and don’t like) at work. Ask this to understand how to navigate happenstance in your career and use it to move forward.
5. If you could talk to your younger self about one career lesson you’ve learned, what would it be?
Sometimes, the hardest lessons are the ones you need the most. Although hearing about your relatives’ life lessons and career challenges can’t keep you from avoiding your own, it can help shorten your learning curve, save time, and improve your focus.
Questions about personal definitions of success
6. How has your definition of success changed over the years?
Everyone defines ‘success’ differently. By asking the people closest to you how their definition of success has evolved, you can better define your own version of success. Their feedback can also remind you that it’s okay if your idea of success shifts as you have new experiences, change your goals, and mature in life.
7. What makes you feel like you’re doing meaningful work?
Many people—including 44 percent of women who participated in a recent InHerSight survey—will only hustle for meaningful work. For some people, meaningful work is any job that allows them to provide for their families. For others, it must align with their personal values. If doing work that feels purposeful is a priority for you, talk to people you trust to figure out what meaningful work means to you and how to pursue it.
8. Do you think you’ve reached your version of success?
Some of your family members may feel like they have been successful in their careers, while others may still be working toward it. You might even find that the people you ask don’t yet have an answer. Talking about career success can bring up a lot of different feelings, including happiness, regret, and indifference. But having these conversations can bring you closer together, while giving you key insight into how to create your own version of success.
9. Is there a moment in your career so far that has made you feel proud?
Reflecting on moments of pride and fulfillment is a great way to learn and an even better way to bond. Your friends’ career achievements, big and small, can inspire you to reach your own goals and give you a chance to celebrate someone else’s success. This is especially helpful during turbulent times in the world, when talking about career wins evokes much-needed feelings of joy, hope, and nostalgia.
10. If you had to define success in one sentence, what would you say?
Get creative when asking your loved ones questions! By challenging them to capture their current version of success in just one sentence, you encourage them to deeply reflect and come up with a statement that is insightful, clever, or downright funny.
Questions for unveiling hidden career regrets
11. Is there a path you wish you’d explored but didn’t? Why or why not?
Sixty-six percent of people have career regrets; half of those workers wish they’d chosen a different career. Getting your friends’ and family’s feedback about the careers they wish they had explored can be especially helpful if you’re feeling stuck and need motivation to pursue the career you want.
12. Was there ever a job you left that you still think about?
People leave jobs for a lot of valid reasons, ranging from ineffective leadership and low pay to poor job security and lack of growth opportunities. Still, nearly all your family and friends could likely name at least one job they wish they hadn’t left. Asking this can prompt honest reflection and help you navigate your own stay-or-go scenarios.
13. Looking back, is there something you wish you’d done differently in your career?
Hindsight is truly 20/20. Asking this uncovers lessons learned that aren’t always obvious in a typical career path. Common things people wish they had done differently in their careers include:
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Leaving a bad job sooner
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Maintaining better work-life balance
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Not taking a job just for the money
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Pursuing a career based on personal interests instead of other people’s expectations
14. Do you ever wonder what your life would’ve looked like if you’d taken a different direction?
While it’s empowering to know you have agency over your career decisions, it can also be intimidating. You may wonder how to choose the right direction for your career when there are so many possibilities.
Your inner circle can explain how their lives would look if they had gone in a different direction, which tells you which factors to consider when picking a new career path or changing your current one.
15. What’s one piece of advice you’d give someone to avoid making the mistakes you made?
This is one question that always gets people thinking, so it makes perfect sense to ask your family and friends—between their unique experiences and how well they know you, your community can offer authentic, personalized advice about how you can avoid making the same mistakes they made.
