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Difficult Conversations and Asking Follow-up Questions

This article provides screeners with strategies for asking follow-up questions during the mentor interview. The mentor interview is an opportunity to learn more about the applicant for matching purposes but, most importantly, it is used to assess whether or not the applicant will be a safe, appropriate and consistent mentor. Sometimes applicants will have vague, conflicting and confusing responses to questions asked during the interview. Screeners should ask follow-up questions to determine the true intent of the applicant and get the most thorough and reliable information possible.

What does listening for safety, appropriateness and consistency mean? 

  • Listening for explicit and implicit biases carried by mentor applicants that may negatively or unfairly impact a student of any identity   
  • Listening for inappropriate behavior – does the applicant have appropriate boundaries? Appropriate social skills for a mentoring relationship with a minor child? Does anything stand out as unusual or predatory?
  • Listening for appropriate motives for mentoring- does the applicant believe in equity and human potential and, in that spirit, wants to support a student? Does the mentor applicant have a savior complex or are they looking for a way to enhance their resume?  
  • Can the mentor applicant commit to the program requirements as outlined for the duration of their match?

Strategies for getting more information:

  • PRO TIP: If you’re ever unsure about an applicant’s response to a question, feel free to ask “can you say more about that?” This simple tool allows you to get more context and gives you time to formulate helpful follow up questions as needed. If there is any tool you take into interviewing, let it be this one. Additionally, there are suggested prompts for following up in the interview script.
  • Ask a direct question for clarification.

Ex: “So you’re saying you travel Mon-Thurs 3 weeks/month. Is your schedule flexible enough to make our monthly weeknight events?”

  • Rephrase the question and repeat as necessary. 

Ex:  Say an applicant is confused by the following interview question- "reflecting on your own experience and potentially those of a teenager in our program, how would you build a relationship with a student who may have had different experiences than you?" You could rephrase it as "What are some skills you rely on for relating across difference?" or "What helps you to relate to people who have different backgrounds and experiences than you?" 

  • Rephrase and repeat their answer and ask the applicant if that is what they meant.  Ex: “What I’m hearing you say is that you would not be comfortable mentoring a student if they weren’t interested in college, is that accurate?” or “When you say you’re a rule-follower and believe that anyone who is undocumented should pursue proper legal documentation, that means you’re in disagreement with undocumented people being in the US and attending college?”
  • Ask a leading question. A leading question is a question that prompts or encourages the desired answer. We are not trying to feed anyone answers per se but we are trying to inculcate mentor applicants on program expectations.
     Ex: we ask mentor applicants how they would support their mentee if their mentee were undocumented. The implicit message is that we expect mentors to be in support of undocumented students while also providing screeners with key information about the mentor’s worldview and mentoring strategy.
  • Ask an open-ended question. Open-ended questions are unstructured questions in which possible answers are not suggested, and the mentor applicant answers in their own words. Open-ended questions require a lot more expounding and can’t just be answered with a yes or no.
     Ex: we could ask “what else can you share with us that will help us to set you up for success in your match?” The closed version of this question would be “is there anything else you’d like to share with us that will help us to set you up for success in your match?” Asking the closed form of this question would elicit a less helpful yes or no response.
  • Feedback sandwich. This is a bolstering and effective way to deliver constructive feedback or ask a difficult question. Start with a (genuine) positive/compliment, deliver feedback/pointed questions, end with a positive/compliment.

Ex: “Your background as a low-income student of color who put himself through college is relatable and something we appreciate in a role model. We are concerned about your ability to commit, given your 100-hr work week and wonder if a structured program like ours would be tenable. Can you say more about how you plan to make this work with your schedule? We are interested in potentially working with you and wants to make sure our program fits your life as well.”

  • Connect mentor applicant’s answers to each other. A great strategy for building rapport and understanding people better is to link their responses to something they said earlier. Good conversationalists and judges of character do this instinctively – they listen intently, and tie what they hear to something said earlier in the conversation.
     Ex: Ask something like, “Oh, yes, you’d mentioned being a perfectionist in high school… do you feel that’s followed you into your professional life?” or, “Is that what you meant earlier when you mentioned how important giving back in college was to you…?”. This not only allows you to understand the applicant better but communicates that you are really listening, not just hearing.

**If in doubt- your manager is happy to talk over any scenario you encounter. People never fail to keep it interesting so remember to enjoy the conversation too!  

FURTHER RESOURCES. You may rely on these pointers and your instincts for asking the most effective follow-up questions. If you need helpful prompts for follow-up questions, please refer to our interview guide or our probing questions bank.  Further examples of applicant responses that require follow-up, and examples of how to structure your follow-up questions, can be found in this Follow-up Questions training document.