Mentoring Matters: How to Be an Effective Mentor

In celebration of our Mentor Community, we recently held “Mentoring Matters,” a Facebook Live event to spotlight a conversation about how to be an effective mentor.

Molly Haleblian, a Chicago mentor, and Sherman Reid, a mentor in NYC, joined to discuss how being a mentor has changed their life, what they’ve learned about supporting their mentees, and how to kickstart a new mentoring relationship. Learn more about becoming a mentor.


Sherman Reid

Hello everybody. How are you doing Molly?

Molly Haleblian:

I'm great. How are you doing Sherman?


I am doing well. Thank you everybody for tuning in. And we want to welcome everybody to this Facebook live event, first ever. How's your week been so far?


Great. I mean, I feel like we've got a new sense of energy around us in so many ways and just really grateful for the new chapter that we're all about to embark on. So feeling really good. How are you?


Exactly. I feel the same way and we're going to get started in a few minutes everyone. Let everybody trickle in. But great week. I don't know, it just feels different. I'm not sure if you've heard it, some of the news press releases. It sounds better, I had to get used to it. I was telling my wife it sounds presidential.


Yes, yes.


Compassion and empathy.


It's so good. It's exactly what we need at this time with everything going on in the world. So I'm feeling good to say the least.


Exactly, exactly. And everybody we have Jamie from the iMentor staff, she'll be monitoring the chat. So if you have any questions, definitely chime in. We want to see if we can get to you, to everything during this session. So welcome. How you feel Molly? I feel a little nervous. I'm a little nervous. Got a little jitters.


No, we're good. We're good. This is fun. This is fun. No, we'll definitely take some time for Q&A at the end, everyone, but definitely want to take some time and just learn about Sherman, your experience, and share our time as mentors.

And hey, it's National Mentoring Month. What an incredible way for us to share our experiences, especially through iMentor, and really just dig in and learn about each other and our different experiences. I'm based in Chicago, Sherman's in New York, although we're connected in the same iMentor program. So it's all an exciting time to celebrate and to be able to provide the support that we do during this wild time in our world.

So Sherman, I think maybe a great way for us to start is just to learn a little bit about you and your mentoring journey. How did you get into it and share a little bit about specifically with iMentor just your experiences.


Thank you for the question, Molly. I started at iMentor through my company. They were having a fair and I joined iMentor because of three different components, important components. The flexibility of the program, the longevity of the program. It was a program where it's a four-year commitment at the time and allowed me to really build a relationship with a young man of color and to really just learn more about him and teach him about my experiences in high school as well as just, I think, what was really great about the program is the iMentor staff are mentors themselves.

So they're not only talking the talk, they also are living it and walking the walk and are fully committed, so that kind of drew me back.

I was like, "Wow, they're not only working in the program and organization and doing a lot of great work in the communities, but they are meeting with their mentees once a month, they're doing the weekly emails." So that actually brought me in and I was sold on that front, but how did you get started, Molly?


Yeah, so in iMentor specifically, I was sent over here by a friend of mine who was a mentor in the program. And it's something that I've been looking to do for a long time. As soon as she started sharing with me about her experiences with her mentee and the relationship that she was building, it immediately resonated with me and I knew it was something I wanted to be a part of.

I've spent a lot of time over the years working specifically with collegiate students, which has been amazing. And although that's been great, I think that being in high school as a student is a totally different ball game. And so, being able to just be another resource for somebody during that time was really important to me. And my mentee is now graduated from high school, but have been with her for the last two years.

Lena has been incredible and she has just taught me so much from a personal standpoint. She's someone that's resilient, has so much grit and our relationship really got to a deeper level than just focusing on what's next for you and where do you want to be when you grow up? We're all figuring that out, right?

So it's been such a journey just to learn about her experience outside of the classroom and how our upbringings were different and not everyone has the same experience. So to be able to just be another resource for her and somebody who she could lean on, on a personal standpoint meant more to me than anything else. And I think that's something that really surprised me about being a mentor too, was just going beyond the next steps in life process.


Exactly. And I think it's also building that friendship. As a mentor, you learn the good, the bad, the ugly about one another and that's, I think, the solid foundation of the relationship.

I first met—and shout out to both of my mentees, Jeffrey and Jamal—I met Jeffrey back in 2012. He was a freshman in high school, very reserved. And I think I hit it off with him because he did remind me so much of my son, Justin, at the time, into video games, very just chill. And as a parent it was like, how are you being so chill? Come on, you need a sense of urgency, but he was very relaxed, got very good grades. He ended up graduating high school and is now actually almost finishing up at Stony Brook College upstate and myself and Justin actually went to go visit him not too long ago last year, had some lunch just check in with him and see how he's doing. He gave us a little tour of the campus, which was fun, so shout out to Jeffrey.

And Jamal is my second mentee. He's a senior in high school and I just found out that he's going to Monroe, so that was great. He was up in the air, didn't know if college was for him, but he got a scholarship and he's going to Monroe, so I'm so excited for him.

He's a little bit opposite, has his own catering business outside of a school, so has his own entrepreneurial thing going on. And that's just exciting to see as a mentor, just to see the growth and the maturity of these young men and women from once we've seen them in high school until they're of age in adulthood. That gives you a sense of pride.

It's like, wow, I had some type of hand in it. I'm not the parent or nothing, but I had a hand in maybe sculpting and just helping this young man or woman to develop as a person, as a human, so that's super rewarding to me.


I couldn't agree with you more, honestly, it is. And especially watching your mentee move from high school to college and just how they transform as a person and you do see so much more maturity come out of them.

And I feel like Lena, especially has really come into her own in the college setting. And although she's doing it all virtually and whoever thought that we would be even talking about that. It's amazing just to see her grasp the schedule and managing her time and just figuring out what work looks like in this world and just managing all the different expectations that are not on her.

And her hand isn't being held as a high school student anymore, she doesn't have as many people looking out and she really has to own it on her own and it's been so impressive to just see her take it on. And yeah, I think that this program in general with iMentor and just the consistency of the support that we have provided to our mentees has set them up for success as they continue on through whatever stage of life comes after high school for them.


Oh, definitely. I second that and speaking of virtual, I think yesterday was actually one year anniversary of COVID, I guess the first case in the U.S. How has your experience been mentoring through this moment, the last 12 months or so? How's it been for you and your mentee Lena?


Yeah, so pre-COVID, Lena was still in high school, so we were still meeting on a monthly basis through the iMentor scheduled programs at her high school and then meeting outside of that as well.

Now that we can't be in person, it's really shifted obviously in a virtual way. And I think it's been overwhelming for all of the students to figure out and navigate this world between school and just personal life. So really our communication has become phone calls and text messages now. Especially as she is in the college setting and outside of the original program through her high school. I think it's hard.

It's really hard because everybody's at a different stage from a mental health standpoint and trying to figure out how to best just manage themselves. And so for me, really just staying consistent in my communication has been key. And I think that's advice that I would give to anybody that's a mentor to others, just make sure that they know you're there and you're available and you're thinking about them.

Overall though, it's been great and I think that our communication has continued to just get stronger because of that consistency. She's crazy incredible and she has a lot on her plate. So just again, continuing to stay consistent in our communication and keeping my door open has been key in continuing to build our relationship. What about you?


Likewise, I think it was important for me to just stay consistent and far as just reaching out to of both of them actually, just, "Hey, how's it going? How are you? How are you feeling mentally? What is your state of mind? How is your family?" Just to check in on them every week, just to make sure that they know whose here.

And what I think I was blown away by was the effort that iMentor staff was doing for the students during that time where everybody was scrambling, educators, students, people, finding daycare or work. The efforts that they went to, the lengths that they went through, just to give hotspots to the children who need it, a wifi connection, any resources for food, especially in transitory housing, things like that.

iMentor would try to move mountains just to help them get by. But again, like you said, it takes a toll on you when you're not used to doing something a certain way, which I think the older generation, I think, helped me as well because I wasn't born in the age of the iPhone, so things that we actually had to do manually helped me a lot to understand that and understand where they're coming from and really be there to help them.

So it was a learning process for everybody, that's the thing. It was definitely a learning process and I just kept positive, kept my faith and just make sure that again, like you said, just stay consistent in making sure that we reached out to our mentees and their families just to check in and let them know that, "Hey, if you need anything come to me and we'll try our best to make it happen or see what we can do. So yeah, that is great. Definitely.

Another question, I guess we touched on it, was how did you pivot your mentoring style, and you alluded to this earlier, just to fit the needs of what was going on? What was some, I guess, if you can have tangible ideas of what you did to pivot? Can you shed some light on that, Molly?


Yeah, yeah. I think at the end of the day, the phrase that always resonates with me is to meet your mentee where they're at. Everybody's at a different stage in their life and especially moving from high school to college and just the transition of time management, I think that it's really just making sure that we're navigating what's the best communication style for our mentees. If that's through an email, if it's through a phone call or a text, it's just working with them and just being very transparent about what they need and not being afraid to ask too, what do I need from our communication too?

It's a two way street and we're here to help each other and learn from each other. So I think overall, just asking them where they are and what support that they need and what you expect in return to with the relationship. What about you?


Yeah, for me, we mainly did our communication through texts. I think we didn't even use the iMentor platform because I thought, again, meeting our mentees where they are, text was the quickest way and most effective way to communicate with him.

But we definitely leveraged the, my program manager, Jason, just to keep the flow of communication open and make sure that again, just checking in on him helping him with his business, trying to give him some creative ideas to keep his business going.

I reached out to a couple of friends just to give him some pointers and that was basically what I thought of and what I could do in terms of just being effective. But again, I had to let him let him be him on his time and not be too pushy.

So I had to learn when to push and went to kind of let him come to me so to speak. But again, adaptation is something that they'll learn and that they have learned throughout this process and again, adaptation is something that you never lose, that you'll keep doing until you're 90, Go willing.


It's true.


We have a question that's in the chat here from Keith Johnson. "How did you break the ice to get the relationship started when there's an age difference and experience difference?" Can you [inaudible 00:17:00], Molly?


Yeah, sure. This was definitely a learning curve for me. I remember when I first met Lena, I'm a high energy person, so I want to know everything about a person. I want to ask a lot of questions and I very much learned quickly that she's the type of person who's a little reserved and there was some trust that needed to be built there before we really got into the nitty gritty.

So I think just not being afraid to take a step back and just overall looking at the state that they are in and looking at the surroundings. Looking at the non-verbals, for sure, have been key for me and just figuring out what her style is, who she is as a person was really important to figure that out.

At the end of the day, though, they want to be treated as a person and the age difference didn't really make a huge matter at the end of the day. We very much found common ground very quickly and areas of interest and just learning about them as a person, I think, yeah.

It's one of those situations where you almost have to take age out of the equation altogether because they want to be respected, they want to be on the same level as you, so not being afraid to just dig in and ask questions that you may ask somebody that you work with or somebody that you meet in a Starbucks. Yeah, you want to treat them exactly the same way that you would treat somebody else. How have you addressed that?


Also, I think I use the acronym TRICK, to be a good mentor or mentoring is trust, respect, independence, collaboration, and kindness. If you approach everything like that in life, I think, good things will come from that, so that's how I personally approach it. So Drew Hobson, he has also has a background in working with college students, his question, "How did you navigate that shift?"


Yeah. Hey, Drew. Drew and I actually went to college together, so this is a fun one. So yeah, I think that in this situation, when I look back at when I first started college and just the amount of freedom that I had, again, going into college and not having teachers who were really looking at me and making sure that I was getting my work done and holding my hand through the process, there was just so much more independence in the college setting.

And when you're working with high school students, they do have more people watching them and making sure that they're following the path and the curriculum that's set out for them. So I think where the shift comes there is that they just have more guidance and just really digging into understand what their relationship is like with the school itself and the faculty and just their friends too.

The people that they're in high school with have been a part of their lives for the last 10 to 12 years of their life. So it's a very different experience than working with college students. There's a lot of history when you walk into a classroom and you look around at the other students as a high schooler. So I think just understanding what their relationship is like again, with the school and the people around them, it just has so much more yeah, history and depth to it. What do you think about that, Sherman?


I definitely agree. The transition from high school to college is much different and in so many different ways. You were a little bit more micromanaged in high school where when you get to college, if you don't do an assignment, that's your prerogative, you don't have to do your homework, but again, there's a consequence for every action that you have.

Where you might have to repeat the same class, but again, in college, you're paying for your classes, right? So that's all part of the tuition and it may set you back in graduation. So if you have a graduation year of 2023, you missing that one class or not passing that one course, it may extend it to the next semester, right?

So you have different ebbs and flows. I know in my college experience, just to be transparent with everybody, I got kicked out. The first year was very difficult and that first year is very crucial, which is why I really think, or give kudos to, iMentor for opening up the post-secondary program to help keep mentor and mentee together, those relationships together after they graduate high school, just to help them with that transition.

Because it could be tough, a lot of students have missing home, they're missing sometimes maybe the food, their family, their friends, it can be very lonely.

And then you can get into mental health and getting depressed, depression can set in just not taking care of yourself. So that's very important, but I got kicked out and I had to reflect and like, wow, this is the consequence of my actions. I got reinstated and then from there, the rest was history. But I had to get that slap in the face and get that kick in the butt, so to speak, to open my eyes.

So that's why this is very important to have a mentor, to have someone that you can go to when you're feeling that any way. So this is exactly why we mentor. I think that's the nail on the head right there.


Definitely. Thank you for sharing that too. I can kick off the next one here from Anne. "Any advice for kick starting the relationship?" She hasn't had too much engagement yet with her mentee. So Sherman, I would love your feedback since you've had two mentees at this point in time.


Again, just stay committed. Because I think when you're coming into this program, a lot of kids have set up the walls, right? And if you reflect back when you were a teenager, seeing an adult, it was just different generations, you didn't just trust somebody.

You had to test them a little bit, see where they're at, see if they're actually really going to do what they say they're going to do. And I would just say, stay consistent. A lot of the mentees are sometimes maybe respond with one word answers, as any typical teenager. I know mine have, but no, stay consistent.

They'll open up. They'll be like, "Oh, she or he is still coming and talking to me and still here, they haven't gone anywhere." Because I find that a lot of students that have faced trauma in their lives early on, so they're probably just not trusting or they just have their walls up and they just are very guarded because they probably had promises made and that weren't kept.

So just stay consistent, keep on being there and you'll see the turnaround, you'll see the turnaround and eventually, she will come and meet you in the middle and you have to just be patient. So patience and consistency. There you go.


I totally 100% agree with you. It ebbs and flows and lives change. We all deal with different things along the way. And I think that's the tricky part too is yeah, we only get to see these mentees in a very concentrated situation through iMentor. And we don't always know what's going on outside of that time period too, whether that's at home or in another classroom. So absolutely stay consistent, do not get discouraged. They will come to you. Yeah, I think that's truly the main feedback that I would also give.


And I think that, just be honest and genuine with them. If you are older, don't trying to be hip, they can sniff that out. Just be yourself and ask questions. I think a young person is like, "Oh, you're interested in what I want to know or, you want to know exactly what I'm doing," or instead of having somebody tell them what to do, if you ask them questions just to get them out the shell, which is a great ice breaker.

But I'm going to get to the next one. Rick is new to iMentor, 2020, and he really appreciates us sharing our practical approaches and experience. So thank you, Rick, and good luck to you on your journey with your mentee and wish you nothing but the best. And if you have any questions for us offline, you can definitely get in contact with us.


Yeah, absolutely. And Sherman, I was going to make a note too, on that last comment you made just about with us continuing to reach out and keeping that consistent communication. I think sometimes “How are you?” can be a difficult question for people to answer, especially during this time.

So not being afraid to just send a funny article or a meme or just something else to help break the ice can just be a welcomed change in the communication style because, yeah, I think sometimes “How are you?” can be like, "Aw man, how am I? There's so much going on, and I'm stressed and I feel stressed now just thinking about how I'm doing."

So what are other ways and other things that you might want to receive from a friend that isn't a how are you too?


And actually, it's funny that you brought that up because I know when I first started in the program, we had to open up our weekly emails with the high of the week and the low of the week. So I think if mentors can continue doing that even in this type of environment, just honest.

Ask that not only of your mentee, but be honest with them as yourself. Be like, "Hey, you know what? I was really struggling, man, my daughter is learning from home, had to make her lunch and this thing and dinner and make breakfast and I just feel very spent."

But also bring a highlight of but I'm thankful to have a job and I'm thankful for having my life. And those are the type of icebreakers or just moments, I think, which is very precious to your mentees can really open up that relationship.

So I think we can probably get back to that dynamic. So Keith Johnson, "Have you found your knowledge about the college process tested and how have you made your insight helpful even if it might be different from your experience to what their experience is?" Ah, that's a good question. That is a great question. Molly, do you have any insight on this? I think I have to think about this a little bit.


Yeah. I think just to keep it brief, I think the one area that I was very challenged on is the financial aid process and just keeping up with understanding how that all works. When I was first asked about it and I was like, "I don't even know where to start." But again, I think that iMentor has set us up for success and has provided so many resources to help us answer those questions.

Yeah, I mean, it looks different now than when I applied for college and went through that whole process too. So not being afraid to also ask for help and being transparent with your mentee too and say, "I don't know, but I'm going to find the answer for you. And we will work through this together." I feel like that's the one immediate thing that comes to mind and yeah, what about you?


Exactly. I think it's a little bit more easier now where a lot of things were manual and everything is online and electronic. So, but again, I leveraged my program manager and would be like, "Hey Jason, I really don't know where to go, how to direct him. Can you point me in the right direction?"

But iMentor is really great about providing us with the resources to go to and just really having those open conversations and also allowing us to reach out to maybe some guidance counselors at the school for extra help as well just to really help us understand that process. But again, my experience is much different. I just try to tell them, enjoy it, enjoy the moment, be in the moment and really take in the experience.

Because you'll look back on this maybe 20 years from now, 10 years from now and be like, "Wow, I had a good experience, maybe I started out a different way," but just enjoy the ride and just be yourself is all I can tell them.


Totally agree. And I think that's a perfect place for us to land here and end this conversation. I feel like we could go on forever, honestly. There's so many things that we could talk about and share, but it's been so nice to just connect with you Sherman and to share our experiences and everyone who joined and ask questions, it means a lot.

So thank you for being a part of this conversation with us. If you are interested in being a mentor with iMentor, please feel free to go to They are regionally in Chicago, New York, Baltimore in the Bay area.

And shout out to our mentors in the Bay and Baltimore area, as well as so happy to have everybody here with us. And if you are a current mentor and are interested in joining any of the racial justice conversations that are happening right now, definitely connect with your program manager. There will be links added in the chat, I believe as well from iMentor staff.

But again, thank you all so much for being a part of this. We are just so thrilled to celebrate National Mentoring Month with all of you and we'll continue to keep pushing and supporting our crew along the way.


Yes, I definitely agree. I second that. Thank you, Molly. And if you are a mentor, a current mentor right now, and you want to do more, you're thinking about how can I make a bigger impact? Please look into becoming a mentor ambassador in your area, as well as a young executive board member as well.

There are a lot of different ways you can contribute on top of just impacting a young life. So definitely check the website, ask or talk to your program managers, anybody that you know and bring in friends, family, connect them to iMentor, show them the work that you're doing and that we're all doing to hopefully make this world a better place.

So we thank you all for joining in and tuning in and thank you so much for all the questions. Molly, I thank you for helping me through this process. Great insight, great conversation and I thank you so much and thank you everybody. Thank you for everybody behind the scenes too.

Watch our video about how one Bronx family in the iMentor community was affected by the pandemic. Read about how a mutual interest in basketball enabled Wayne Sharpe, a mentor with iMentor Baltimore, to support Kyion, his mentee, in planning for college. Learn more about becoming a mentor.