Meeting someone new can be challenging, especially in a professional context. Not only is there pressure to ask the right questions, communicate clearly, and show your professionalism, but there’s also the sometimes awkward dynamic of trying to get to know someone in “work mode.”
That being said, it helps to prepare for meeting someone new with specific questions –which is why we're giving you 15 great questions and conversation starters that you can use during your first meeting to find some common ground.
These interview questions are designed specifically for a meeting with someone new in the context of mentorship. That being said, many of them can be applied to any sort of professional meeting– peer to peer, a formal interview, or a networking opportunity.
One final note: Though you might have arrange a meetup for this kind of connection, it’s likely that you’ll in fact be having these conversations via a “virtual coffee chat,” or a video call. In an age of rapidly growing remote work–due to distance, convenience, and growing need for safety–more professionals are meeting “virtually” than ever. All the more reason to be prepared, as video calls demand a higher degree of attention, focus, and intentionality than in-person meetings.
In any case, these questions can help you enter any meeting more confidently and create meaningful conversations...and most importantly, help both parties get the most out of the interaction.
Coffee Chat Questions About Work History & Personal Development
First, you’ll want to establish a general context for your mentee. Understanding a bit of their personal work history will help you to ask more intelligent, targeted questions down the line...and give context to their answers.
That being said here are a few coffee chat questions that you can ask upfront, to get your virtual chat off on the right foot.
How did you get started in your career at this company?
Asking a mentee how they got started on their career path at your company can help inform your understanding of their training, goals, and skill sets. Your mentee may have had a long-term goal to work in your industry...or they may have ended up there by accident. Either way, they bring something valuable to the table. Just because someone “stumbled” onto a career path doesn’t mean they’re unmotivated or can’t be extraordinarily successful.
Tell me a little bit about your professional background.
This gives your mentee an opportunity to share about other professional experiences that may add context to their current position, skill set, or goals. This also lets your mentee know that you value their entire professional history, and are invested in their work history outside of your specific industry or company.
What’s been one of your most positive professional experiences–in this company or in a role at another organization?
This question gives you an opportunity to dive deeper into what makes your colleague feel accomplished and fulfilled. For one person, it may be a leadership position on a major project; for another, it may be developing a positive work relationship with a former boss. In any case, learning what they're passionate about can be a valuable tool in helping them to develop and reach goals.
Asking personal questions, when done appropriately, can help break the ice in a meeting, make your mentee feel more valued, and help create a healthier, more enjoyable interaction for both parties. Not only that, but personal questions can help to build rapport & connectors – key for a productive mentorship relationship.
How are you doing?
It’s an obvious question, but asking your mentee how they’re doing outside of the context of work and engaging in small talk helps them to know that you value their overall wellbeing as well as their professional growth. This question has been more important than ever during the coronavirus pandemic, creating an enormous amount of uncertainty and stress that may affect your mentee more than you may know.
How is your family?
Expressing interest in the wellbeing of your mentee’s loved ones helps build the relationship and acknowledges their interests and attention outside of their job. And, if they’re going through something difficult, it can help set them at ease–even if they don’t choose to share details.
What do you do for fun?
Asking about hobbies and interests brings some fun into the conversation, and helps give you more of an idea of your mentee’s personality. It also gives your mentee an opportunity to share a passion or area of expertise that helps make the interaction with you a bit less intimidating.
“Problem-Solving” Coffee Chat Questions
The next set of coffee chat questions will focus on hurdles, areas of conflict, or general issues that your mentee is facing at work. This is where you’ll start to dive into the “meat” of your relationship with your mentee, and help them begin to problem-solve.
What hurdles are you facing right now in your job?
Give your mentee an opportunity to tell you about hurdles they’re currently facing in their particular role. This could be a lack of time or resources, poor communication about a particular project, a difficult client, or a general feeling of stagnancy in their position.
How are your relationships to your colleagues and to leadership?
Although this can be a sensitive area to address, it’s important to ask a mentee about their relationships to others. Unhealthy relationships in the workplace not only decrease employee satisfaction, but they can damage a colleague’s ability to be productive–and even result in churn.
Do you have any other concerns that may be addressed?
If your mentee is dealing with an issue that doesn’t fit into any of the above categories, then give them an open-ended opportunity to share their concerns. They might be dealing with a mental health issue, a fear about an upcoming project or deadline, or a non-work related issue that’s affecting their ability to thrive. In any case, give them an opportunity to share–and let them know you’re there to listen.
Questions About Goal-Setting
Helping your mentee set and reach their professional development goals is one of the most important parts of mentorship. Question-asking is a key part of this, as you give your mentee the direction they need to think through their goals and how they plan to achieve them.
Where do you see yourself in 1 year?
Asking your mentees about their one-year vision helps them to think through short-term goals that can help them to work towards a new line of work, develop a new skill set, or launch a new initiative or project. Starting from the end vision and working backwards will help your mentee to set goals they actually want to achieve...not just goals they think they should want to achieve (like gain a new job title or start a side hustle).
Where do you see yourself in 5 years?
Stretching the timeline from 1 year to 5 years helps your mentee think even “bigger picture.” It’s at this point in the conversation where you may discover your mentee has some surprising goals and aspirations–like starting their own organization, developing an entirely new skill set, or creating a podcast. This question can also help mentees set additional short-term goals that may help them to achieve their bigger dreams, and allows you to step into the role of career coach to help get them there.
What are some personal goals you’d like to work on?
Your mentee may have more general personal goals that they’d like to work–such as better focus, more confident public speaking, or greater self-discipline. Remember that as a mentor, you’re not just helping your mentee to develop in specific ways as a professional, but to grow as a more successful human.
Questions About Strategy
Finally, you’ll want to be strategic about follow-up. What are coffee chat questions you can ask to make sure that your meeting produces action, and not just good conversation? Here are three ideas.
What are you going to do this week to improve at ______?
Circling back to one of your mentee’s short-term or personal goals, ask them how they plan to take immediate action in order to begin meeting those goals. This compels them to create some actionable steps to which you can hold them accountable.
Are there any hurdles that may prevent you from achieving your goals?
Help your mentee troubleshoot and problem-solve hurdles before they allow them to damage their plans for growth.
How can I help you grow in your career?
Finally, give your mentee a chance to describe how they envision your mentorship relationship evolving over time. They may be looking for specific insight and advice from you that you hadn’t thought of; here’s their opportunity to tell you what they’d like out of your relationship, perhaps by helping them in a job search or providing referrals.
Plan Your Next Virtual Coffee with Ten Thousand Coffees
Virtual coffee can be an engaging, effective way to develop productive mentorship relationships between colleagues–which can ultimately increase employee engagement and make your organization stronger.
That being said, you’ll want to implement a strategic program to make sure that virtual mentorship is realistic, convenient, and measurable.
Ten Thousand Coffees is a talent development platform that:
- Matches mentors and mentees using strategic algorithms
- Syncs with your existing tools and systems for easy communication and onboarding
- Measures engagement and adoption to keep mentorship accountable
- And ties directly to your business goals
To learn more about how you can use Ten Thousand Coffees to develop talent, increase engagement, and build a stronger professional network at your organization, get in touch with one of our experts, today.