77 career conversation starters for employees, bosses, networking professionals

If you know how to spark meaningful career conversations, you’re a lot more likely to be successful. 

Why? Opportunities can be found anywhere — only if you talk with the right person. 

Over the last decade, I went from being a third-world country kid — with zero connections, zero skills, zero pedigree — to doing the following:

• Partnering with an Inc. 30 under 30 entrepreneur and building his business brick-by-brick for close to eight years
• Collaborating with top entrepreneurs and experts, including the first marketing director at Paypal 
• Screening thousands of job candidates and hiring the very best of them

A large part of my success is due to my ability to start conversations and build relationships. 

In this article, I will share a list of my favorite career conversation starters.

When and how to use these questions 

No hard rules per se, but here are a few suggestions:

• Ask one question at a time. Gauge their response before going deeper. If they seem disinterested in the topic, switch to something else instead.
• Balance between asking and talking. Make sure that you share your answer to the same question, or comment on their answer, so that the conversation doesn’t become an interrogation 🙂 I’ve been guilty of that.
• Most importantly, modify the questions and brainstorm new ones based on what sounds/feels most natural to you.
  
  Why is that important? Different people have different ways of saying things. The more you can tailor the conversation starter to your tone of voice, personality etc., the easier (read: less awkward) you will find using it.To make this more usable for you, I’ve tried introducing variations of the same question 🙂

Career conversation starters at the office 

Office chitchat is a great way to get to know people at work!

Here are 7 ways to start a conversation with your colleague and make friends at work.

Career conversation starters at professional events e.g. conferences

Asking “what do you do” isn’t a crime, but how do you follow up from there without turning it into a boring business back-and-forth? (Sorry, I just had to alliterate 🙂 

Here are a few questions you could try: 

1. How did you end up in this job? // What made you choose this career over others? 
2. What surprised you when you first started out in your career/current job? 
3. What do you find most rewarding about your job? // What was the most rewarding moment in your job? 
4. What do you find most interesting/fascinating about your job?
5. What do most people misunderstand about your job? // What’s one thing you wish more people knew about your job?

A few things to note: 

• Notice how they are focused on the stories and emotions around the other person’s career, which makes the conversation a lot more interesting.
• If you are particularly curious about their career journey, check out the career journey questions above.
• For more ways to start conversations, check out my other article: How to talk to strangers at a conference

Career conversation starters at social events e.g. parties

Given that the typical intent isn’t business, I prefer asking fun or imaginative questions — keeping it “business casual” 🙂 

These questions aren’t party-specific, you can ask ’em at informal family and friend gatherings. 

Small talk 

1. What do you do for a living? // What’re you working on these days? 
2. What are you building these days? (This is a great question if you know that your family member/friend is entrepreneurial) 
3. How’s work coming along today/this week/month? 
4. Anything interesting/crazy at work today/this week/month? 

Deep questions 

1. What’s the craziest thing that happened to you in your job? // What’s the most memorable thing that happened to you in your job?
2. If you could wave a magic wand, what would you change about your career? 
3. If money wasn’t a concern, what career would you like to try out?
4. If you could be in any career for a day, what would it be?
5. Would you rather work for money or work for passion? Why?  

Note: If the conversation takes a more serious turn — I certainly have had deep career/business conversations after a few drinks — check out the professional event Qs — they will help you transition from lighthearted to thoughtful.

Career conversation starters with your employee

These are best in a 1-on-1 meeting where there’s time and space to hear your employee out. 

I like asking this every week or month, so that I can get a pulse on how they feel about their work and the company.  

Role 

1. How do you feel about your team/manager so far?
2. How do you feel about your progress in <project/task> so far?
3. What do you enjoy the most about your work? 
4. What do you hate doing? (Note: not every employee is comfortable sharing about this, since they might worry about not performing up to standards. 
5. What do you find most challenging about your work? // What’s your #1 challenge in your job? 
6. Where do you feel stuck in your job?
7. How do you prefer receiving feedback?
8. What feedback do you have for me as your manager/boss?

Motivation 

1. What motivates you at work? // What gets you up in the morning? 
2. What do you value the most: money, prestige, vision, autonomy, or something else? // What do you care about the most and why? 
3. What makes you feel appreciated at work? Why? // Tell me about a moment when you felt especially appreciated at work. 
4. What are your top one to three professional goals? What support do you need the most? 
5. What are your top one to three personal goals? What support do you need the most? 
6. How do you think about your learning and growth in your role? (This is a solid alternative to questions #5 and #6, since not everyone might be goal-oriented.) 

Career conversation starters with colleagues

I’ve organized these to go from small talk to deep questions. You can also ask the motivation questions above.  

Environment

1. What’s your ideal work environment? // Where do you get the most work done? 
2. What’s your ideal workweek/day and why? 
3. What’s the favorite part of your workweek/day and why?

Collaboration 

1. What method of communication do you prefer the most/least? 
2. What would you say your communication style is? 
3. How do you typically give feedback? 
4. How do you prefer receiving feedback?
5. How do you resolve conflict at work?  

Career journey 

1. How did you end up in this job? // What made you choose this career over others?  
2. What’s your career journey? 
3. What was your first job like? 
4. How did you go from <X role/industry> to <Y role/industry>?
   (Career transitions are fairly common these days, and you can often uncover great stories from this angle. This is a good follow-up to #2)  
5. What accomplishment are you most proud of? // What’s the biggest win of your career? // What’s the highlight of your career? 
6. What was the biggest challenge in your career? // What was the toughest moment in your career? How did you overcome it? 
7. What’s the most valuable/important lesson you’ve learned from your career?
8. If you were to give career advice to your younger self, what would you say and why? // What do you wish you’d known when you started your career? 
9. What’s the most helpful piece of career advice that you’ve ever gotten? 
10. Who made the biggest difference in your career and why? // Who are you grateful for in your career and why? 

Career conversation starters with your manager/boss 

These questions help you understand your boss better — especially when it comes to what they think about your work. I wished more of my employees or freelancers had asked me these questions 🙂 

This gives you important intel that you will need to negotiate a raise or promotion. 

If you’re having a casual chat, say over beer, you can also ask the career journey questions above. 

Role 

1. What’s the #1 piece of advice you have for me/my role?
2. What would you say are the top three qualities of any employee?
3. What would make someone trustworthy in your eyes? (Note: you can also ask the opposite.) 
4. I have XYZ responsibilities (name a few of them). What responsibility do you see as most important/critical to the company’s success? 
5. We’ve worked together for <X months/years>. What would you say is my #1 strength and #1 weakness/area of development? 
6. Let’s say we’ve worked together for one year. What would make my role a success vs. failure? 
7. How can I make your job easier? How can I help you save time/be more productive?

Vision 

1. What’s your most important goal and why? 
2. What do you hope to see happen in our department/company?
3. Where do you see us going in the next 3/6/12 months? How does my role fit in?
4. What is your biggest problem and how can I solve it? (Credit: Lori Goler, former marketing director at eBay)

Career conversation starters with your mentor/mentee 

In the last decade, I’ve been a mentor and mentee to more than a dozen people. 

Here are a few questions that I find most valuable in building a successful mentor-mentee relationship. 

If you’re the mentor

1. What do you enjoy doing and why? // What are you most curious about? What do you seem naturally drawn towards? (Note: this can also be a good question if you’re talking to students or younger people.)
2. What’s your #1 career/personal challenge right now? 
3. What are your goals in the next 3/6/12 months? 
4. What kind of support do you need from me? // What support would be life-changing for you? 
5. What do you hope to learn from me and why? 

If you’re the mentee 

1. What would make this a meaningful mentor-mentee relationship for you? // What would make mentoring fun for you? 
2. Given what you know of me, what’s the most important thing I should be learning and why? 
3. What’s the one piece of career/life advice you would give me? 
4. What do you wish your mentee(s) ask about you? // What do you wish your mentee(s) know about you?
5. Given that you’ve mentored me for <months/years>, what would you say is my #1 strength and #1 area of development?