Career Advice
December 22, 2021

5 types of Mentorship Questions To Ask Your Mentor

5 types of Mentorship Questions To Ask Your Mentor

5 types of Mentorship Questions To Ask Your Mentor

Yaay! Your mentoring program sessions are booked. Go you! If this is your first mentoring session, you might wonder about the types of questions to ask your mentor. Asking questions to your mentors is important as the answers could inspire and guide you in your current or future careers. These five types of questions might help you to achieve a meaningful and successful mentorship program.

Learn the tips to find a mentor here.


1. Ice Breaker Questions ( For getting to know your mentor)

Meeting someone for the first time is nerve-wracking. You have no idea what they are like, whether they are going to like you, whether they could tolerate your questionable sense of humor or whether the program is going to be a success as you plan it to be. Do not worry so much, dear courageous mentees!

You have the power to control the present. Perhaps visualizing the first day of a mentoring session would create some confidence in you. Set a friendly virtual space, where you start to get to know your mentor ( and they get to know you too!). Even if the mentor seems to have a non-interest in the beginning, start with simple icebreaker questions such as “ How are you?”, “How’s your day”, “Oh, you have a cat too?!” -when you see the mentor’s cat suddenly jump onto their keyboard. You can use the surroundings as conversation starters too such as the mentor’s nice outfit, the picture in the background, or the current weather. 

Both you and your mentor need small chats to feel relaxed, and at the same time, establish a  good rapport.

Below is a list of questions to ask your mentor (examples) :

  • How did you start your design career? 
  • How did you get to where you are today? 
  • What aspect of your job excites you the most?
  • What is your typical day like as a designer/manager ____ (mentors’ job title)? 
  • What do you wish you had known before taking your first design role?
  • What is/are the goal(s) you are currently working towards? 
  • Why did you decide to be a mentor?
  • What is your preferred way of communication? 



2. Career Setback Stories ( To mentally prepare for similar obstacles in the future)

Rejections or obstacles play a huge role on the road to success. You can never know what does not work if you do not fail. Successful people, including your mentors, have encountered multiple setbacks before being who they are today. It is not an overnight success story. We heard about the blood, the tears, and the sweats. But what do they mean by that? Ask your mentors to spill the tea 😬. Get to know the inside scoop of their hardships when they are at their lowest point in life. 

As someone relatively new to the industry, knowing what might come your way would be helpful. So that you are mentally prepared and have some ideas on ways to overcome the issue. You, my friend, might have just discovered the secrets to critical issue management at an earlier stage. 

Phewwww. 😌😌😌

Below is a list of questions to ask your mentor (examples):

  • How was your job searching experience for your first design job? What were your job searching strategies and how you would improve them?
  • Was there a time that you messed up and felt like you would fail? How did you overcome it?
  • What is the most important lesson you have learned when you was a junior designer? 

3. Career Inspirations (Books, people, other types of resources)

Now that you have known their struggles, it is time to get to know their magic wands! 🪄

Salagadoola mechicka boola
Bibbidi-bobbidi-boo
Put them together and what have you got
Bibbidi-bobbidi-boo!

No, not that one 😆. In reality, magic wands are the tools that inspire your mentors to work harder, work smarter and succeed. Find out the books they have read, the people they follow on Twitter and other social media platforms, the videos or movies they have watched, their rituals (waking up at 5 AM, food to win, or the types of video games they are into). 

Get inspired! 

Below is a list of questions to ask your mentor (examples):

  • How do you keep up with the UX/product design trends? 
  • What are your favourite career/UX design resources?
  • Do you follow any industry experts on social media?  
  • Do you have any suggestions for continuing education courses?
  • Can you recommend any good books that will help me enhance X skill?



4. Receive Constructive feedback (Highlighting your weaknesses and strengths)

Non-honey-coated comments are sure a stab to your heart ( and multiple unmerciful slaps to your ego 😵‍💫). But deep down inside, you know you need them as the seeds to your career growth and development. Gather your courage and ask your mentor about your weaknesses and strengths.

You have spent some time with your mentor, and they have gotten to know you (briefly) for a few weeks. Keep an open heart and listen to their feedback. Evaluate and reflect on those feedbacks. How can you improve based on the comments? How can you maintain your strengths? 

This is your chance to gain honest insights about your present achievements, your present personality, and how you can succeed in the industry. 

Below is a list of questions to ask your mentor examples:

  • Would you please offer feedback on ways to improve my portfolios and resumes? 
  • Do you have any advice on how I can approach UX portfolio presentation / salary negotiation? 
  • What new skills do I need to move ahead if I want to achieve X (your goal)?



5. Cross-checking career goals (Share your future career plan with your mentor)

Your mentorship program is almost over. Only a few sessions left. Grab this opportunity to cross-check your future career plan with your mentor. For examples:

  • “I plan to study A in 2022. Will this course still be relevant by then?”
  • “As a beginner at animation, will tool X be able to assist me?”
  • “Will my career plan take me where I want to be in 5 years?”


Bear in mind that your mentor (too) is still learning and adapting to the rapidly changing industry, but from their years of experience, they could advise you on what works and share suggestions on how to assist with your career development. Take their advice into consideration.

Below is  another list of questions to ask your mentor (examples by our mentor):

  • Do you prefer to do short-term mentoring or long-term mentoring? 
  • How often can we meet? 
  • How can I better prepare for our next meeting?
  • Can we review our goals for this mentorship together? 


Note: The list examples of questions are shared by our mentor Janus Tiu, a UX Designer at Critical Mass.

Download this worksheet by Janus on Preparing for your first meeting with your mentor and if you want to know more great tips on UX, subscribe to Janus Tiu Youtube channel.

Now there is no reason to attend your mentoring sessions unprepared 🤓.