Informational interviews can unlock valuable insights into potential career paths and open doors to exciting opportunities.
Yet many people hesitate to reach out, unsure of what to say or ask.
As a seasoned professional, you know informational interviews are a powerful tool for gathering intel and building connections.
But to make the most of these conversations, you need to come prepared with thoughtful, engaging questions that encourage your interviewee to open up and share their wisdom.
Questions to Ask in an Informational Interview
Ready to dive in?
Here are 10 essential questions to guide your next informational interview and help you gain the knowledge and confidence to advance your career.
1. What does a typical day in your role look like?
Asking about someone’s day-to-day responsibilities provides a realistic picture of the job. You might phrase it as “I’d love to get a sense of what your average workday involves. Could you walk me through a typical day in your role?”
Understanding the nitty-gritty details – the meetings, the projects, the ebbs and flows – helps you envision yourself in that position. Do the daily tasks align with your skills and interests? Does the rhythm of the role suit your working style?
If their days are packed with client meetings and you’re an introverted type, that could be a red flag. On the flip side, it might be an ideal fit if they describe a collaborative, team-oriented culture and you thrive on social interaction.
Please pay attention to how they describe the pace and intensity of their work. Do they seem energized or overwhelmed? Are you excited or burnt out? Their tone can reveal a lot about the true demands and rewards of the job.
2. What are the most rewarding and challenging aspects of your work?
Every job has its ups and downs. Asking about the highs and lows gives you a balanced perspective on the role. Try phrasing it like, “What parts of your job do you find most fulfilling? And what are the biggest challenges you face?”
If they light up talking about the rewarding parts – the creative problem-solving, the team camaraderie, the sense of impact – that’s a good sign. It means there are meaningful motivators beyond just a paycheck.
But don’t shy away from the tough stuff. Asking about challenges shows you’re not naive about the realities of the role. It also allows you to gauge how well you’d handle the inevitable obstacles and frustrations.
Maybe they struggle with work-life balance or difficult clients. Maybe the role requires a lot of tedious paperwork or red tape. Knowing the downsides upfront can help you decide whether the job aligns with your priorities and dealbreakers.
Just remember, every challenge is an opportunity for growth. If they frame the hard parts as chances to learn and adapt, that reflects a healthy, resilient mindset. And those are the kind of colleagues you want in your corner.
3. How did you get started in this field? What was your career path?
Asking about someone’s career journey can yield valuable insights and inspiration for your path. You might say something like, “I’m curious about your career trajectory. What led you to this field, and how did you end up in your current role?”
Learning how they navigated their early career – the detours, the lucky breaks, the defining moments – can help you envision your way forward. What stepping stones did they take? What skills or experiences proved pivotal? Their story might surface new possibilities you hadn’t considered.
If their path was a winding road, that can be reassuring. It’s a reminder that careers often unfold in unexpected ways, and there’s more than one “right” way to get where you want to go. Embracing that flexibility can open you up to promising opportunities off the beaten path.
On the other hand, if they had a clear vision and followed a linear track, that can be instructive too. It shows the power of setting goals, acquiring key credentials, and doggedly going after what you want.
Chances are, their journey involved a mix of planning and happenstance, strategy and serendipity. The key is staying open to the twists and turns, while still being proactive about your professional development. And if you hit a dead end or need to pivot? That’s just part of the adventure.
4. What skills or qualities are most important for success in this role?
To gauge whether a role plays to your strengths, it helps to know what it takes to thrive. Consider asking, “In your experience, what skills or attributes are essential for excelling in this kind of work? Both the technical competencies and the soft skills?”
Their answers can help you identify which of your talents might transfer well, and which you may need to develop. Do they emphasize hard skills like data analysis or coding languages? Or soft skills like communication, creativity, and adaptability?
If the must-have skills align closely with your existing abilities, that’s promising. It means you have a solid foundation to build on. You can probe for examples of how they’ve applied those skills, and envision yourself doing the same.
If there are key skills you lack, don’t panic. Instead, get curious about how you might acquire them. Are there courses, certifications, or stretch projects that could help you build those muscles?
Remember, skills can be learned. What’s harder to teach are the innate qualities like drive, integrity, and empathy. If they emphasize those core character traits, reflect on whether they ring true for you.
Of course, no one checks every box perfectly. The goal is to get a realistic sense of the key requirements and assess whether you have the aptitude and appetite to grow into them. With the right combination of ability and hustle, most skills can be mastered.
5. What are the most pressing challenges or trends in your industry right now?
Staying on top of industry developments is key to future-proofing your career. Try asking, “What are the biggest issues or changes happening in your field currently? And how are those trends reshaping the skills needed to succeed?”
Their insights can help you understand the competitive landscape and anticipate where the puck is headed. What are the disruptive technologies or shifting consumer habits that are transforming their work? What new regulations or geopolitical forces are they grappling with?
If they describe a field that’s evolving at warp speed, that can be both exciting and daunting. On one hand, rapid change creates opportunities for those who can adapt and innovate. On the other, it can be stressful to constantly update your skills and knowledge.
If they paint a picture of an industry that’s relatively stable, that has pros and cons too. While there may be less pressure to reinvent yourself, you also risk getting too comfortable and stagnating in your role.
Ultimately, the key is to find a field and function that ignites your curiosity and passion for ongoing learning. Whether you’re energized by pioneering new frontiers or incrementally refining your craft, staying engaged and proactive is what will keep you ahead of the curve.
And don’t just take their word for it. Use this intel as a jumping-off point to do your research on industry trends and forecasts. The more informed and attuned you are to the changing tides, the better positioned you’ll be to navigate them with agility and purpose.
6. What are the common career paths in this field? What options for advancement exist?
Understanding the typical trajectories in a field can help you envision your growth potential. Consider phrasing it as, “Could you give me a sense of the usual career progression in your line of work? What do the advancement opportunities generally look like?”
If they sketch out a clear ladder of roles and responsibilities, that can be heartening. It suggests there’s a structured path for rising through the ranks, with increasing impact and rewards along the way. You might probe for specifics on the key competencies and experiences needed to springboard from one level to the next.
If their field has a flatter structure with fewer linear paths, that can be liberating in its way. It may mean there’s more wiggle room to shape your role around your evolving interests and strengths. You can ask how others have charted unique paths by taking on stretch assignments or moving laterally across functions.
Whatever the shape of the career landscape, the important thing is that it aligns with your values and ambitions. Are you energized by the idea of deep expertise in one domain, or do you thrive on exploring new territories?
Also, consider how you feel about the scope and speed of advancement. In some fields, it may take many years of dues-paying to reach higher altitudes. In others, standout achievements can catapult you quickly up the ladder. There’s no right or wrong answer, only what meshes with your temperament and timeline.
Of course, career paths are rarely a straight line. They often have detours and switchbacks as you gain new skills, interests, and priorities. The key is staying open to unexpected turns, while still being proactive about your development. And if you ever feel boxed in? Remember, your trajectory is yours to design.
7. What advice would you give to someone hoping to break into this field?
Asking a seasoned pro for their hard-won wisdom is a surefire way to gather valuable nuggets. Try saying, “Knowing what you know now, what guidance would you offer someone like me who’s eager to get a foot in the door?”
They might share tactical tips on crafting a standout resume or acing a technical interview. They might suggest professional associations to join or thought leaders to follow to stay current on industry happenings. Or they might advise on the soft skills and interpersonal strategies for making a positive first impression.
If they recommend a specific credential or experience as a key door-opener, that’s a clue to prioritize those in your career prep. If they tell a funny anecdote about a rookie mistake they made, that’s a gem to tuck away and avoid yourself.
Sometimes the most impactful advice isn’t about external tactics, but internal mindsets. They might share hard-earned lessons on resilience in the face of rejection, or the importance of advocating for your growth. Those pearls of emotional wisdom can be just as valuable as any technical tip.
Of course, what worked for them won’t necessarily be your exact recipe for success. But hearing their seasoned perspective can save you some trial and error as you find your way.
The beauty of informational interviews is the chance to gather a range of viewpoints. The more people you talk to, the more data points you have to triangulate your path. Take what resonates, leave what doesn’t, and keep honing your instincts and expertise.
8. Is there anyone else you would recommend I speak with to learn more?
One conversation often leads to many more. Before wrapping up, consider asking, “Is there anyone else in your network you think I should connect with to keep exploring this path? I’d welcome an introduction if you’re willing!”
This is a chance to keep widening your web of contacts and gathering new perspectives. Maybe they know someone who took an unconventional route into the field, or who works in a different sector or geography. Each conversation adds another color to your canvas of career possibilities.
If they’re willing to open their rolodex, that’s a testament to the positive impression you’ve made. It means they see potential in you and want to help nurture it. Accept those introductions graciously, and be sure to circle back with a thank you.
Even if they don’t have a specific contact to share, you can still tap their wisdom. Ask if they know of any upcoming industry events, or if they’re part of any online communities where you might lurk and learn. The goal is to keep expanding your knowledge network.
Remember, building your career community is a long game. Not every conversation will yield an immediate nugget or next step. But every exchange plants a seed that may sprout into something fruitful down the line.
Stay curious, stay open, and keep nurturing those budding relationships. You never know which conversation may be the one that changes everything.
9. Looking back, is there anything you would have done differently in your career journey?
Hindsight is a powerful teacher. Asking someone to reflect on their past choices can unearth valuable lessons for your path forward. You might pose it as, “With the benefit of experience, is there anything you wish you had done differently in your career? Any decisions or moves you would have made sooner or later?”
Their answers may surprise you. Maybe they wish they had taken more risks early on, or been bolder about asking for stretch assignments. Maybe they stayed too long in a toxic work environment or passed up a big opportunity out of fear.
If they express regrets about not investing more in their skills or network, that’s a nudge to prioritize your professional development. If they wish they’d been more proactive about seeking mentors, that’s a reminder to nurture those guidance relationships.
Sometimes their hindsight reflections may be about work-life tradeoffs. Maybe they wish they’d set firmer boundaries around their time, or been more present with family. Those insights can help you think deliberately about your definition of success, and how to craft a career that honors your whole life.
Of course, their hindsight is filtered through their unique lens. What felt like a misstep to them may be the right risk for you to take. The key is to extract the underlying lessons and apply them to your context.
And remember, even the best-laid plans can go awry. The goal isn’t to plot a mistake-proof path but to cultivate the resilience and resourcefulness to navigate the inevitable bumps. If you can learn from others’ detours and stay true to your north star, you’ll be well-equipped for the journey ahead.
10. What keeps you engaged and excited about your work? What gives you a sense of purpose?
Work is about more than just a paycheck. It’s a chance to make a meaningful impact and express your deepest values. As you close the conversation, consider asking, “What aspects of your work bring you the most fulfillment? When do you feel most alive and purposeful in your job?”
Their answers can shed light on the intrinsic motivators that fuel their best work. Maybe it’s the thrill of cracking a complex challenge or the satisfaction of mentoring rising talent. Maybe it’s knowing their efforts contribute to a cause larger than themselves.
If their sense of purpose resonates with your own, that’s a strong signal of fit. It means you share a similar worldview and set of values. You can dig deeper into how they’ve shaped their role to align with their passions and imagine yourself doing the same.
If their version of fulfillment feels disconnected from yours, that’s important intel too. It might be a clue that this particular path won’t light your inner fire in the long run. You can reflect on what does bring you alive, and start steering your career in that direction.
Ultimately, the goal of work is to honor your unique gifts and make a positive dent in the universe. When you tap into what gives you a sense of meaning and mastery, that’s when you do your best work.
So keep exploring, and keep listening to your inner compass. The more you understand what makes you come alive, the better you can craft a career that feeds your soul and serves the greater good.
Wrapping Up: Vital Questions to Inform Your Career Path
Informational interviews are a powerful tool for gathering intel, forging connections, and charting a career path that aligns with your values and ambitions.
By asking these 10 vital questions, you’ll gain a richer understanding of potential roles and start building relationships that can open new doors.
Remember, every conversation is a chance to learn, grow, and refine your career vision.
Stay curious, stay open, and keep seeking out diverse perspectives.
The insights you glean will be the building blocks of a career that is both fulfilling and impactful.
So go ahead, and reach out to that person whose work you admire.
Come prepared with thoughtful questions, and genuine enthusiasm.
Listen closely, take good notes, and always follow up with a heartfelt thank-you.
Your dream career is out there waiting to be discovered.
One conversation at a time, you’ll find your way to work that matches your talents and feeds your soul.
The adventure is just beginning!