While no mentee-mentor pair is ever the same, here are some general strategies that Program Coordinators can employ to have productive conversations with both mentors and mentees.

Preparing for the conversation

• Focus your efforts by only working on one issue a pair is having at a time. Pick the one that’s affecting their relationship the most (e.g. they’re not communicating) to work on first—it will usually help resolve smaller issues, too. Don’t try to get the pair to write AND meet AND talk about family finances all at once.
• Use people who know the mentee to provide context on behavior or for ideas on engaging mentees. These include friends, counselors, teachers and school administrators who have been around for a while. This also helps you build valuable relationships at the school.
• Check your anxiety and discomfort before entering a difficult conversation. Fully preparing will put you in a great place to engage, but if you are still uncomfortable, practice the conversation with your manager. 
• Make sure you can give the mentor or mentee your full attention before entering the conversation. This will require significant focus on your part if the conversation is happening at an event or during a class session.

Opening the conversation:

• If the mentor/mentee has requested the conversation, always state your appreciation: “Thanks for reaching out to me. It shows that you really care about your commitment to X.”
• Regardless of who initiated the conversation, also thank them for taking the time to talk and remind them that your ultimate goal is to support them to have a meaningful and productive relationship.

Assessing the situation

• Ask lots of open probing questions to fully understand what the mentor or mentee is experiencing. For example, “How are you doing? How are you feeling? What have you experienced? Why do you think this is happening?”
• Try to zoom out from a specific situation into larger context when a mentor/mentee seems really fixated on something specific. E.g. “how does X seem to be doing at school and home generally?” or “does this behavior line up with other things Y has said?” This can be especially useful when someone is taking something personally because it can move the conversation from an unproductive rant to a useful discussion.

Responding in productive ways

• Acknowledge how someone is feeling explicitly, through body language or words.
• Normalize the experience (“a lot of mentors/mentees feel this way at this stage”).
• Use your experience as a PC to contextualize and normal experiences. E.g. “I see about 10 students writing to their mentorwithout my reminders, and your mentee is one of them” or “It takes most pairs at least a few months to really start opening up to each other; you two seem to be on track.” This can also be used (tactfully) to add positive peer pressure “Most pairs have met 5 times this year, so let’s figure out how we can get you two to catch up to them.”
• Share your observations using a neutral tone and language, whether those observations support or contradict the mentor/mentee’s views. This can be especially difficult when you’re trying to empathize--it’s especially important to make sure you’re not heightening a mentor/mentee’s feeling of being wronged. E.g. go for “Your mentee has been a little distracted in class lately. Do you have context on why that could be?” vs. “It makes a lot of sense that your mentee’s messages have been shorter since she’s been distracted in class—I can’t get her to sit still, let alone write!”
• Move the conversation away from people-blaming language to situation-examining language to avoid making the mentor/mentee feel defensive. Instead of saying “I think your mentee might be hesitant to attend because you didn’t attend the last event,” try “your mentee seems hesitant to attend this event. Can you think of any reasons why?” or “Your mentee might still feel upset that she didn’t get to see you last time.”
• When a mentee is feeling like her mentor doesn’t care, ask her to recall what the mentor has said or done to make her feel this way. Empathize, and then ask her to recall what the mentor has done or said in the past that made her feel like her mentor cares. S/he can write these down if s/he doesn’t want to say and look through old messages to help with this exercise. If s/he can’t think of any, share your own positive observations as a trigger. You can also share your own experience of letting negative actions/words trump positive ones in your relationships to demonstrate the importance of not letting one bad experience stain your entire relationship.
• Remind mentors and mentees of the small successes they have had.

Brainstorming solutions

• Relying on the mentor’s and mentee’s expertise on each other is a great way to reinforce your partnership with them. For example, “how do you think X would react to this, based on how you’ve seen him/her behave in the past?” or “what does X enjoy doing? That sounds really fun--suggest doing Y activity with him/her and let’s see how s/he feels about it.” Another way to do it is by using “we” language, e.g. “There are a couple of things we can try.”
• If the mentee/mentor is having trouble coming up with solutions to a problem despite coaching questions, try suggesting things that have worked for you. E.g. “I’ve found that cracking jokes when X is down doesn’t help. Instead, I give her some time to herself and let her know that I’ll be back to chat in a few minutes.”
• Encourage pairs feeling distant to reconnect on things they have clicked on in the past. Sifting through early ‘get-to-know-you’ messages and notes can help dig these up.
• Tell mentors/mentees what you as a PC have done and will do to help with a situation, and ask them if they think that will help.

Making recommendations

• End the conversation with one or two takeaways or tactics generated by the conversation.
• Set concrete deadlines for milestones. Avoid saying “ASAP.” Coach mentors and mentees to set their own deadlines as much as possible (“when can you do X by? Great, I’ll check back in on [day after].”)
• Now that the mentor or mentee has shared their feelings with you, if appropriate, encourage them to share their feelings with the other. Don’t be tempted to share on their behalf (unless they fail to do it themselves consistently). You want them to get comfortable expressing themselves to one another, so ask them which medium they want to use (writing/in-person meetings/phone calls or text) and if they can use their next interaction to express their concerns. Suggest or model language they can use if they seem to be struggling.
• Provide specific examples and language when making suggestions (“tell your mentor how you feel about not getting a message from them, for example ‘I was a little sad when I didn’t see a message from you.’”) Do this only after the mentor/mentee has expressed to you how s/he feels so you’re not putting words in anyone’s mouth.
• Frame your requests to mentors/mentees in terms of their other half’s needs, not as your own requests. E.g. “Your mentee/mentor is waiting for your RSVP to make plans,” versus “please RSVP so I know who’s coming to the event.”
• Remind mentors/mentees of their commitment to one another by thanking them for it.

Following up

• Set an explicit time/day for follow-up, and mark it on your calendar with what you need to follow up on. Then, follow up on that exact day.

Using the GROW Model

• Use the GROW model -- especially when talking to a mentor or mentee with whom you are tempted to jump to prescriptive language. Make sure you are aware of the situation the mentor/mentee is in (Reality), where they need to go (Goal), how they might get there (Options), and the clear next steps (Way Forward).
• Ask the mentor/mentee questions that help you and them to get this information. Most often, they will start expressing what they need to do to move forward if your questions are helping them to identify obstacles and options. Some probing questions: “what have you seen?”, “why do you think that is?”, “what did X do to make you feel that way?”, “what have you tried?”, “what else have you thought about doing?”, “what does Y respond well to?”, “how do you want to approach this?”

For a quick introduction to the GROW Model, watch the following video.

Have another strategy you have found useful? Leave it in the comments below.