25 Questions to Ask When Exploring Your Next Career Move.
We all know how important networking conversations are in a career pivot or job search.
When we work with people, we call them prototype conversations (thanks Bill Burnett & Dave Evans for this awesome framework!). A prototype conversation is conversation with someone who is either doing what you’re thinking about, or has real experience and expertise in an area you have questions about. The conversation allows you to ‘try on’ what it feels like to work in specific role/industry/place. It’s about exploring for the right fit on your search – not getting a specific job.
No matter what you call it, you want to show up with genuine curiosity and ask good questions that will help you find out what it would be like to do that person’s work. If you’re really good at asking questions, you’ll know which path makes the most sense for you right now, and you’ll get a good idea as to where the opportunities might be in the future.
Here’s our list of top 25 questions to ask in these conversations:
GETTING TO KNOW THE PERSON
I’d love to hear about your path, and how you got into the [role/industry] you’re in now.
How did you know this was what you were interested in doing?
What did you expect about your current [work/role/industry]?
What didn’t you expect about your current [work/role/industry]?
What do you wish you had known before you got into this [role/industry/organization]?
What’s the most challenging thing about your work?
Where do you see yourself wanting to move to over the next 5-10 years in your career?
UNDERSTANDING THE INDUSTRY & SIMILAR ORGANIZATIONS
What challenges do you foresee in the next few years in this [industry/company]?
From where you stand, what do you see are the biggest challenges or problems facing [tailor to type of customer] right now? What are the ways companies like yours are addressing them?
What are some of the differences between [company] and other similar organizations?
What does a typical client engagement look like at [company]?
Who does well, and who wouldn’t do well in this industry? Why?
Are there certain degrees or certifications that are necessary to work in this industry?
How would you describe the culture at this [organization] and others like it?
What are 3 adjectives you’d use to describe what it’s like to work in a company like this?
UNDERSTANDING THE ROLE
Could you tell me about a project you’ve worked on that you think really embodies what it’s like to work at [company/organization]?
When you look at 10 other people in similar roles, what aspects of their background do you share? What’s different?
I want to understand the trajectory is of people in these roles. What are some of the places that people have ended up who were in similar roles to you 10 years ago
What abilities do you think someone needs to be able to do well in this kind of role?(Things like: Being extroverted, passionate about x, loving details, stamina)
Are there other roles that have similarities to one that might draw on the same strengths?
Are there experiences or education credentials that are critical to succeeding in this role?
GETTING TO NEXT STEPS
What advice would you have for someone like me who’s interested in getting into this kind of [role/company/industry]?
What’s one step you might suggest I take to learn about more opportunities in this world?
Are there special sites, resources, or groups I should be aware of that might help me connect with others to learn more, or find opportunities?
Your perspective has been so helpful on this [industry/company/role]. I’d love to get an additional perspective – is there someone you’d suggest I talk with who might have a very different perspective than yours and might be willing to share their experience?