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Krithika Chandramouli
Krithika Chandramouli

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10 Questions and Prompts for Your Next 1-on-1 with Your Mentor

I previously wrote about mentoring and being a mentee, and how it can really help accelerate your career by giving you insights into many topics ranging from your blind spots in your trajectory to perspective on an incident that happened with you.

As a mentor I’ve worked with junior engineers who walk into a meeting with me without much idea on what to talk about and end up winging it. At that point I take it upon myself to navigate conversations with them to make 1-on-1s productive by asking a series of questions to understand what takeaways they are looking for.

In this post I shed light on some of these insightful pointers and prompts that can help mentees who have identified a great candidate for a mentor get started on building a long term relationship with them.

I classify them loosely on two axes. The first axis is questions about mentors vs questions about mentees. The second axis is broader career related questions that are longer term vs questions about incidents and behaviours that pertain more to the near term.

10. How did you get into mentorship?

It’s interesting to know what motivates other people in general. But with someone who is mentoring you, it might be great to get an insight into to their beginning story and journey.

9. What is next in your career?

Your mentor may be a little ahead of you in their journey but knowing how they are going to navigate their career just like you’re trying to will give you some perspective on continuous learning, and give you a sneak peek into things you currently don’t quite know but will learn eventually when you’re at the level that your mentor is at.

8. What does your day to day look like?

When I was a junior engineer, I would always be curious about all the meetings that some of the more senior members of my team would attend, or if I would see calendars blocked out for some of them. But I never had a chance to ask. With a mentor you have that chance! Get curious about what they’re up to day-to-day to help you paint an image of what you’re growing towards in your career.

7. How did you go from level n to level n+1?

It might be tempting to ask “How do I go from my current level to the next”. But your mentor might have have too many answers for you there if they lack context on your work and how you operate. A better question to ask is how they go to their current level or how they got a certain promotion. They journey can serve as a great example to you when thinking about your own promotion. More importantly, their mistakes could help you get a sense of what not to do when aiming for your next promotion.

6. How can I get more visibility in my team/org/company?

One of the important factors in our growth is perception management- how to manage how people perceive you. Getting visibility for the work that you’re doing might be an essential step in this, and might be a great topic for your next 1:1. There is always a certain level of visibility that could help boost our confidence and positively reinforce the good work we’re doing.

5. Can you help me talk through my strengths and weaknesses?

This is a great exercise to do with your mentor, and a personal favourite. By using your mentor as a sounding board you’re able to put yourself under the microscope and be your own critic. Bonus question: which weaknesses do you think will hold me back in the long run?

4. How do I get better at a certain skill or adopting certain behaviours?

Whether you’re intimidated by code reviews, or speaking up in a meeting, or anything in between- your mentor might be able to guide you through navigating these skills that you are looking to improve but find no real guidance outside in your team. While it is great to emulate people around you, it is good to also keep in mind to bring in your own authenticity when developing soft skills and behaviours.

3. At this point in my career what should I focus on?

Your mentor would likely have passed through the very same stage in their career as your are right now, and might have a healthy point of view on what is next in line for the team/org/company. Your mentors opinions here on whether you should be focusing on honing your skills or learning a new technology or leading more projects might help you understand where to put in work to grow.

2. I was in a meeting when a co-worker said this (to me)…

This one is a bit more situational, and not necessarily in a bad way. We all have workplace interactions with our co-workers that we sometimes need to unpack especially when it directly applies to us. Your mentor may not have been present in the meeting but your mentor might be able to talk through a workplace incident with you in a judgement free and safe way.

1. I’m stuck on an issue in code and I can’t move forward…

There are large long term questions about your career to be pondered over, but some days you just have to get stuff done. If your mentor works on the same technologies as you do, chance is they might be able to help you with whatever you’re stuck on so feel free to utilize them as a resource!

If you found this article interesting here’s another story in the mentorship series: 5 Key Aspects of a Mentor-Mentee Relationship. I hope you found a valuable conversation starter for your next 1:1. Thanks for reading!

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