#67 12 Questions to Ask in Mentoring Sessions with Felipe Flores – Founder & Podcast Host

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In this episode, Felipe talks about an aspect of leadership, the one-on-one mentorship and feedback session with people on your team. To start, ask your team member what is on their mind and in general, how have things been going? If they do not have anything pressing they want to discuss in the sessions, Felipe turns to set of twelve questions. The first question is what you are most proud of that you have done since we last caught up? These questions are designed as tools for the team member to recognize the need for self-assessment. What they say is not essential; really, the follow-up questions are more necessary to help them uncover themselves. Next, ask what the team member could have done better since the last time you talked. By allowing them to evaluate and think of improving continually, they can learn faster and become more efficient in their work. 

The next few questions require a broader perspective and ask about the team as a whole. It should be clear that everything is a team effort, and all member’s ideas are respected and heard by others on the team. After the team questions, head back to questions about the person and ask what they would like to work on or improve? Then, the next issue will take a lot of trust and rapport with your team member, ask what is one thing that is true that you think I do not want to hear? Question nine is how I can help you to do better? This question has taught Felipe that he is good at the big picture but needs to focus on the details and how the team might achieve the big picture. Finally, the last three questions are asking what they like best and least about the organization and if they are happy at the moment.

Enjoy the show!

We speak about:

  • [01:35] Open-ended questions

  • [02:15] What are you most proud of that you have done since we last caught up?

  • [03:45] What could you have done better?  

  • [05:30] Questions about the team

  • [10:00] What would you like to work on or improve? 

  • [11:40] What is one thing that is true that you think I do not want to hear?

  • [13:10] How can I help you to do better?

  • [15:00] What do you like the least about the team? 

  • [16:00] What do you like best about the team?  

  • [16:35] Are you happy at the moment? 


Saturday Night Live


  • “One of the best and quickest ways to learn is to evaluate your efforts continually.” 

  • “Understand the human behind the data scientist.” 

  • “You don’t need to be fixing every person’s problem, but everyone needs help every now and again.”

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Felipe Flores is based in Melbourne, Australia.

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