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Episode 07

How Do We Mentor the Next Generation of IT Leaders?


Show Notes

New tech graduates enter the workforce every year. What generational differences and unique challenges will these younger professionals face? Mentorship is essential to make the transition into enterprise IT, regardless of where a person worked before. But it’s not always clear what mentees need, or what would be most beneficial for them. 


In this episode, we speak to people about what makes a good mentor, how learning can go both ways, and what is most meaningful in mentoring relationships.


00:02 - Kim Huang 

Angela, do you have a mentor?

00:04 - Angela Andrews 

So I have two official mentors, one that I talk to pretty frequently, the other one, not very much. And then I have a, I guess, unofficial mentor who I talk to at least once a week.

00:19 - Kim Huang 

How about you, Brent?

 00:20 - Brent Simoneaux

I would actually consider my current boss a mentor, absolutely. I also have, I guess, a more official mentor and that is really wonderful because one, he's not my boss, but two, he works in a completely different area. So he's able to have a lot of good perspective on my career, on challenges that I'm facing. So I have lucked out with some really great mentors. What about you, Kim?

00:51 - Kim Huang 

I have not had a very good experience with mentorship. I'll be honest.

00:55 - Brent Simoneaux 

Oh no.

00:56 - Kim Huang 

Yeah. I probably have quite a few people I look up to, but for me, mentorship is kind of nerve wracking.

01:04 - Brent Simoneaux 

Why is it nerve wracking for you?

01:05 - Kim Huang 

Well, for me, it's like, I'm always in fear of people judging me. So it doesn't really matter if that person's my boss or not. I'm always fearful of being judged or critiqued for my performance and the things that I'm doing or not doing.

01:19 - Angela Andrews 

I think we carry those insecurities when we expose ourselves to folks. Right.

01:25 - Brent Simoneaux 


01:26 - Angela Andrews 

And sometimes you have to worry, are they going to judge me by something that I just said? So I don't think that goes away just as a human being. I don't think that really goes away if you do or don't have a good mentor.

01:39 - Brent Simoneaux 

I think in listening to all of our experiences with mentorship, it seems like there's a lot of variability: who your mentor is, how often you meet, what you talk about, and even whether it's valuable or not. And I don't know that I've ever really thought about what makes a good mentoring relationship.

02:04 - Kim Huang 

You know what Brent, I had the same question. So let's find out together.

02:11 - Brent Simoneaux 

This is Compiler, an original podcast from Red Hat.

02:15 - Angela Andrews 

We're your hosts.

02:17 - Brent Simoneaux

I'm Brent Simoneaux.

02:18 - Angela Andrews 

And I'm Angela Andrews.

02:20 - Brent Simoneaux 

We are here to break down questions from the tech industry; big, small, and sometimes strange.

02:27 - Angela Andrews 

Each episode, we talk to people working in the tech industry, including Red Hatters like us.

02:33 - Brent Simoneaux 

Today's question. How do we mentor the next generation of IT leaders?

02:41 - Angela Andrews 

Producer Kim Huang dug into this topic. Here she is.

02:45 - Kim Huang 

I decided to speak to a couple of people about the topic of mentorship, people who have kind of been on both sides, right?

02:53 - Brent Simoneaux 

Oh yeah.

02:53 - Kim Huang 

So I started off speaking to Hugh Brock. He helped craft the mentorship program that Red Hat has with Boston University. And he talked a little bit about how the program started.

03:08 - Hugh Brock 

I had the opportunity to come over to Boston and open up the office there and also launch our first ever real research relationship with a university, which was with Boston University. On the one hand, dealing with professors and university research and developing an intern program more or less from scratch and all of the other things that go along with that, I was for sure making it up as I went along.

03:36 - Kim Huang 

Hugh talked a lot about the students that he works with in the program and how they view things like open source, for example. He says that while there is an attraction to open source, it's sometimes a really hard concept for people to grasp.

03:52 - Hugh Brock 

When I talk to undergraduates, I talk to prospective Red Hat interns, or Red Hat employees. And I tell them, "We work in the open. Your work remains your own. We don't tell you which upstream projects you can contribute to." I think that really resonates with people, but at the same time, I think it's also hard for them to understand working in the open. What does that mean? Does that mean everybody's going to criticize, going to be able to critique everything that I do? And the answer is yes. So there's a large element of support that goes along with that.

04:25 - Kim Huang 

In some cases, meeting a mentor like Hugh might be their first exposure to technologists, to the way they work, to the way they think. Before this, a person may have been learning to code on their own, through videos or books.

04:41 - Brent Simoneaux 

Angela, I'm curious about the moment in your career when you switched from learning from a book to learning from a person.

04:52 - Angela Andrews 

Oh gosh. So that was the way you learned.

04:56 - Brent Simoneaux 


04:56 - Angela Andrews 

That transition to learning from people was very gradual. You usually learn from the people around you that are the closest, your colleagues, your boss, and that circle tends to get a little bit bigger. You go to conferences, you go to some sort of training, you learn from as many channels as you can.

05:19 - Brent Simoneaux 


05:19 - Angela Andrews 

Think about it. Back in the nineties, there was not this YouTube, there was not all of these online learning platforms.

05:26 - Brent Simoneaux 

I think maybe one really great thing, but also really bad thing, about books and YouTube and other things like them is that they don't talk back.

05:40 - Angela Andrews 

Yes. Yes. You have a point, you have a point there because feedback is really important in anyone's learning process and that's what's missing in those methodologies.

05:51 - Kim Huang  

I definitely agree with that.

05:55 - Brent Simoneaux 

So going back to what Hugh was saying about his work at Boston University, one of the troubles that he pinpoints is that some students have trouble opening themselves up to critique. Is that right, Kim?

06:10 - Kim Huang 

That's right. Think about it. If you're learning how to code on your own, if you are mostly studying in a program, you're not necessarily working with other people. You're in a very solitary learning environment. And then for the first time you're opening yourself up to critique, doing like code reviews and code comments, and things of that nature. So that can be a little bit of a shift that a lot of these younger tech professionals are not accustomed to and have not encountered before. It's not necessarily a bad thing. It's just that it's something that's very new.

06:46 - Brent Simoneaux 

Yeah. It's scary and also unpredictable.

06:48 - Kim Huang 


06:48 - Angela Andrews 

Especially when you're young and you're starting out. Feedback, if you're not used to receiving constructive feedback, it can feel like a criticism.

06:59 - Brent Simoneaux 

Oh yeah.

06:59 - Angela Andrews 

So the delivery in which that information is coming is so important. And of course the deliverer, the person delivering it is really important because otherwise you might not be able to hear it.

07:13 - Kim Huang 

I wanted to talk to someone who was on both sides of the mentorship spectrum. So I decided to have a chat with Oindrilla Chatterjee. She's a data scientist who works at the Red Hat AI Center of Excellence. Oindrilla was a mentee in the program at BU and since then she's become a mentor herself. I asked her about the role of mentors and a person's development. And she started out by talking about the unique position a mentor can have in being a safe space for a young tech professional to express their thoughts and concerns.

07:47 - Oindrilla Chatterjee 

The core duty of mentors is to create that safe environment for mentees to ask questions that they wouldn't necessarily ask their managers. And it gives an opportunity for those people who are coming into the tech industry to get support from someone apart from your direct team members who are analyzing you, grading you, or directly responsible for your performance.

08:15 - Kim Huang 

The pressure to perform, plus generational differences, can result in a mentee needing very different kinds of nuanced things from their mentors. Oindrilla says that today's mentees are no different than any generation and that they could benefit from that type of empathy.

08:35 - Oindrilla Chatterjee 

Checking in, having conversations about what the mentees are working on, or just empathizing with their situation, that they might be really struggling hard to prove themselves, or get a job done by themselves without asking for help.

08:51 - Kim Huang 

Getting a job done without asking for help. That was a really big thing that stuck out to me.

08:55 - Angela Andrews 

Yeah. There's really no specific part in your journey that this doesn't apply to. Not for just the new students and new people just entering tech, but this is for anyone along their tech journey. You really do need that space where you can benefit from that type of empathy. Because again, not for your team, not your boss, not anyone in that chain, but someone outside of it that can just give you that space to be is really important.

09:24 - Brent Simoneaux 

And it seems like Oindrilla is the perfect person to help us out here because she's been on both sides. She's been a mentee and a mentor. I'm curious, Kim, how does she create empathy in a mentorship relationship?

09:41 - Kim Huang 

I asked her exactly that.

09:43 - Oindrilla Chatterjee

As a mentor myself, I like to set these 30 minute check-ins at the start of every week, a time where the mentees can come and talk about what they did over the past week and just discuss any of the challenges that they faced and just plan forward for the next week. And remember, this is very different from a general team's sprint planning or sprint demos. This is very conversational. This is a time where we can really talk about how could we have done something better, or what are some things which as a mentor I can help you with to accomplish your goals.

10:23 - Brent Simoneaux 

So she's talking about the importance of having someone outside of your team, right?

10:29 - Kim Huang 

Yeah. And that person creating time and space for you.

10:32 - Brent Simoneaux 


10:32 - Kim Huang 

That's not something that I think mentees are positioned to ask for directly. So it's really important that it's offered.

10:39 - Brent Simoneaux 


10:41 - Angela Andrews 

That's a hard ask, right? I mean, we can ask for someone to mentor us, but this little benefit that Oindrilla is providing, we wouldn't know how to ask for something like that. We wouldn't know that we could.

10:55 - Brent Simoneaux 

Yeah. There's something I found really special about instead of the mentee scheduling time with the mentor, sometimes having the mentor schedule time with the mentee.

11:05 - Angela Andrews 


11:06 - Brent Simoneaux 

That feels like a gift and it feels really special.

11:10 - Kim Huang 

At first I approached this story thinking about, all right, people that are coming to tech for the first time, they may be freshly graduated from a computer science program. I was thinking along the lines of what their identity is and what their concerns are. So I talked to Hema Veeradhi. She is a software engineer at Red Hat. And I wanted to know about her experience in the mentorship program at Boston University as well.

11:42 - Hema Veeradhi 

I feel everybody who comes out of college, you're sort of confused. I don't know if it's everybody, but I can say that for a lot of people, because there's so much there. There's so much, you have opportunities to take and it is confusing. It can be overwhelming as well. You're trying to make the right choice because this is something that you want to pursue in the future. And this is, you have your own goals.

12:05 - Kim Huang 

So a little bit of background about Hema. She did go to Boston University, but she did her undergraduate study in her native Bangalore, India. So in order to go to the program at BU she had to leave her family behind in India. She came here alone, separated from her family and that introduced a lot of different concerns and worries and obviously a lot of stress, right? You're separated from your family, everybody that you know, trying to transition into a different world basically.

12:36 - Hema Veeradhi

I think coming from that to an industry where you have a diverse bunch of people with tons of experience, there are super senior people in the company, super talented people, but there are also a lot of your own peers as well, who may have been older or younger. So it does get intimidating. I think that's how I felt. There are so many people. There are so many great people that sometimes you wonder what you are able to offer.

13:06 - Brent Simoneaux 

Angela, take us back to your early career. Does this resonate with your experience?

13:12 - Angela Andrews 

I wasn't leaving my family and my home place. But from where I grew up, moving into this space of higher ed and then moving into this space of corporate America, it was really a culture shift. It was a different type of diversity than I was used to. Everybody didn't look like me. So it went from being very comfortable to now having to stretch yourself because you have to make sure that you can communicate with folks that aren't like you. You know what I mean? They don't speak your language. And to her point, probably very literally they don't speak your language. And you get the people who've been around longer than you. So you still have on your training wheels, they don't. So you, there's that little bit of intimidation. Is this right for me? Am I doing this right? I'm not really sure.

14:04 - Angela Andrews 

And in your defense, as someone in this space, you have to believe very strongly that you belong there and you have a place. So that's what gets you to the next hurdle, that gets you to the next project, that gets you through to the next assignment. Imposter syndrome is real and it can be couched in so many different things. But knowing you belong there really does take you where you need to go.

14:32 - Brent Simoneaux 

I think for me, it actually took someone saying, "You belong here."

14:39 - Angela Andrews 


14:40 - Brent Simoneaux 

Quite explicitly. I think it's like, there are so many opportunities it's kind of scary, but then also you look around and I work with a lot of really talented people. Yeah, like you said, imposter syndrome is real. I feel it.

14:57 - Angela Andrews 

I bet you, it didn't end there.

14:58 - Brent Simoneaux 

No, Uh-huh (affirmative),

14:59 - Angela Andrews 

I bet you, you probably had that thought once, twice, a couple more times. You have to keep reassuring yourself, always, that you belong. So it's a struggle.

15:12 - Brent Simoneaux 

The value of having a mentor, right, especially someone who's been around longer and maybe someone who is really successful or someone that you can see yourself being in some ways, saying that back to you, it's almost like a future self saying it back your current self that you belong here and you can do this. Man, that goes a long way.

15:38 - Angela Andrews 

That means so much. Yes. Thank you for saying that. It means so much.

15:44 - Brent Simoneaux 


15:45 - Kim Huang 

Both Oindrilla and Hema came from a really heavy computer science background. They both studied. They both had people and their family and their friends that were already in the tech industry. So they were kind of assured a little bit, at least in their, I guess, belonging. But what if someone doesn't have that?

16:05 - Brent Simoneaux 

Oh yeah.

16:06 - Kim Huang 

What are their needs? Especially in a mentorship program, do their needs change? And what are some of the things that they could teach, maybe, the mentors themselves about how to approach young people who are trying to get into tech for the first time? So we heard from Hugh who created a mentorship program. We heard from Oindrilla and Hema who have kind of seen both sides of mentorship in both roles. Let me introduce you to Cali Dolfi. She's a data scientist at Red Hat. And I spoke to her about some of the needs and the wants that both mentors and mentees have. She says, one of the needs is the need to be vulnerable about what a person knows and what they don't know.

16:58 - Cali Dolfi 

I think a huge portion of breaking down that barrier as well is pretty much just being straight up, being like, you know what? I don't really know what I'm doing completely either. I think it's really a sense of vulnerability as well, necessary on both sides. And I think it's a responsibility of the mentor to show a little bit of vulnerability for the mentee can feel comfortable doing that as well.

17:20 - Kim Huang 

Here's the thing about Cali. She didn't have as much experience as all of her classmates in her computer science degree program. So she said it was a concern that she had to feel comfortable to share things with her mentor who gave her the support that she needed at the time.

17:37 - Cali Dolfi 

I can say that it can be really intimidating. And I would say that my technical expertise was actually something that I was very insecure about going into my internship at the beginning and I had a really great mentor in Oindrilla who was constantly like, "Oh, you don't understand this. Let's get on a call and let's figure this out together."

17:58 - Kim Huang 

Oh yeah, that's right. Her mentor was Oindrilla Chatterjee.

18:01 - Angela Andrews 


18:01 - Kim Huang 

Who we heard from earlier in the episode.

18:04 - Brent Simoneaux 

I see what you did there, Kim.

18:08 - Kim Huang 

Yeah. So remember when Oindrilla was talking about generational differences?

18:12 - Brent Simoneaux 


18:12 - Kim Huang 

Cali says that those differences can present in more than just a frustrating kind of way. They can also present unique opportunities.

18:23 - Cali Dolfi 

When people can start to break down their walls and figure out that they can learn from both directions is when you actually start to get somewhere. I found with all of my mentors at Red Hat, their excitement towards talking with me and hearing what I have to say. And just something that I was constantly hearing about is the energy that the newer people bring in and the new ideas. You need both sides of it.

18:47 - Brent Simoneaux 

Oh, okay. I see what she's saying.

18:52 - Kim Huang 


18:52 - Brent Simoneaux 

So she's saying that it's not just about the mentee, the person who is mentored learning from this is getting very confusing. I need to...

19:01 - Angela Andrews 

We need a cheat sheet.

19:01 - Brent Simoneaux 

I need a cheat sheet. She's saying that a mentor can learn just as much from their mentee.

19:12 - Angela Andrews 

Oh for sure.

19:13 - Brent Simoneaux 


19:14 - Angela Andrews 

I agree. I mean, in that relationship, it definitely goes both ways. The mentee is definitely learning from the mentor, but think about how much the mentor is learning from this person. So in Cali's case, think about it. She came from a non-tech background, maybe different than some of her counterparts. She didn't have that technical foundation and curriculum before she got to college. So she was learning on the fly. So having a mentor that could listen to her and empathize with her in that relationship, it probably made for such a great symbiotic relationship between the two of them. And I think she mentions that, that was a really good relationship. So both ways, for sure.

20:03 - Brent Simoneaux 

It seems like a less valuable mentorship relationship is where the mentor is like I have all of this knowledge and experience. Let me bequeath that to you.

20:18 - Angela Andrews 

Yes, exactly. And that's not how it works.

20:21 - Brent Simoneaux 

Or let me make you into a miniature version of me.

20:27 - Angela Andrews 

Oh, wow.

20:28 - Brent Simoneaux 

I would put that on the bad side.

20:29 - Kim Huang 


20:29 - Angela Andrews 

Yeah. That's definitely not a win-win in the mentor-mentee relationship.

20:37 - Kim Huang 

I think that a lot of people approach mentorship from the dominant side being the mentor, the seasoned professional. Just as you said, Brent, kind of like, "I'm going to pass on my experience to you," kind of like passing some kind of ancient kind of knowledge or something. I think that's the prevailing, maybe it's a prevailing belief, but the ideal mentorship experience is insightful for both the person who's being mentored and also the person who's doing the mentoring.

21:11 - Brent Simoneaux 

And what a gift too. I feel like that's another way of saying you belong here. It's another way of saying you have something to offer because you have just taught me something.

21:27 - Kim Huang 

Cali walked into a program like this with less of a foundation than the other people in her program. So it was important to see her for who she was and the things that she cared about.

21:41 - Cali Dolfi 

I had a lot of people who took chances on me because they knew I was passionate about my work and passionate just as a human being. And so I just think that's why I enjoy working in open source because it's so much about the people and that's the same that you can kind of get with mentorship. And your personal impact can go so much farther if you choose to invest in others.

22:05 - Brent Simoneaux 

Kim, you have talked to a lot of people for this episode. What I want to know now is what you have learned.

22:14 - Kim Huang 

I think that mentorship should not be a kind of copy paste situation. I think that mentors should approach mentorship as a very nuanced kind of relationship with the person that they choose to interact with or they choose to mentor. Not all mentorships look alike and they shouldn't.

22:43 - Brent Simoneaux 

All right. Can we try a challenge?

22:45 - Kim Huang 


22:45 - Angela Andrews

Sure. What's that?

22:46 - Brent Simoneaux 

Here's what I want us to do: I want the three of us, and I'm also going to challenge the rest of the audience to do this as well, but we're going to start it, the three of us, we're going to try to find some new mentors. So here's my question, Angela. If you could have any mentor in the world, who would you want to be your mentor?

23:10 - Angela Andrews 

Oh my gosh. If I could pick a mentor, it would have to be Cree Summer.

23:15 - Brent Simoneaux 

Who is Cree Summer?

23:17 - Angela Andrews 

She is a voice actress and I've been following her since she was on A Different World, a TV show many, many years ago. And she pivoted into voice acting. I would love to be a voice actor. That's my secret thing that I have going on in my head. So, I would love if I could be mentored by Cree Summer. That would be insane.

23:40 - Brent Simoneaux 

What about you, Kim?

23:41 - Kim Huang 

I think that my dream mentor would be Missy Elliot, the hip hop artist and producer.

23:48 - Brent Simoneaux 


23:48 - Angela Andrews 


23:49 - Kim Huang 

Yes. She came from a very similar background as me. She's from the same state as me. And she has always been kind of irreverent to whatever is contemporary or in style. She kind of set so many different kind of standards and so many different trends. And I think that that's so strong and so cool. And she always puts out amazing work because of it. And that's who I would pick in a heartbeat.

24:17 - Angela Andrews 

That's a good one.

24:18 - Brent Simoneaux 

That is a good one. I love it. All right. So here's what we're going to do. We are going to shoot our shots. Are we going to do this? Are we making a pact?

24:30 - Kim Huang 

Yes we are.

24:31 - Angela Andrews 

Yes we are. Wait, you didn't tell us; who would be your mentor?

24:35 - Brent Simoneaux 

Oh. So I think that I want Jad Abumrad to be my mentor. He hosts this show and created a show called Radiolab. And I think that he is brilliant.

24:48 - Kim Huang 


24:49 - Angela Andrews 

All right.

24:49 - Brent Simoneaux 

All right.

24:50 - Angela Andrews 

That's awesome. Let's do this.

24:51 - Brent Simoneaux 

So we're going to make a pact and listeners, we want you to do this as well. Even if you don't even think it's possible, tag them on Twitter. Shoot your shot. Let's make this happen.

25:02 - Angela Andrews 


25:03 - Kim Huang 

I love it.

25:04 - Angela Andrews 

That's fantastic. I'm so excited.

25:07 - Kim Huang 

I know.

25:10 - Angela Andrews 

And that does it for this episode of Compiler.

25:14 - Brent Simoneaux 

Today's episode was produced by Kim Huang and Caroline Creaghead. Victoria Lawton is the mentor of our dreams.

25:23 - Angela Andrews 

Our audio engineer is Kristie Chan. She was helped on this episode by Elisabeth Hart. Special thanks to Shawn Cole. Our theme song was composed by Mary Ancheta.

25:34 - Brent Simoneaux 

A big thank you to our guests: Hugh Brock, Oindrilla Chatterjee, Hema Veeradhi and Cali Dolfi. Another big thanks to Boston University for their help with this episode. If you want to know more about how Red Hat works with universities, check out

25:53 - Angela Andrews 

Our audio team includes Leigh Day, Laura Barnes, Claire Allison, Nick Burns, Aaron Williamson, Karen King, Boo Boo Howse, Rachel Ertel, Mike Compton, Ocean Matthews, and Laura Walters.

26:08 - Brent Simoneaux

If you like the show, please follow for future episodes and tell your friends about it. That is the best way to help our show. Angela, you said you wanted to be a voice actor one day. Would you read the last line in your best cartoon voice?

26:28 - Angela Andrews 

Sure. Why not? Until next time, see you soon!

26:37 - Brent Simoneaux 

Angela, hats off. You can't see me, but I am standing and I'm applauding.

26:42 - Kim Huang


26:43 - Angela Andrews 

Wow. That was funny.



Featured guests

Hugh Brock

Oindrilla Chatterjee

Hema Veeradhi

Cali Dolfi

We were so excited about our episode on licenses—so we have a special project that we want to share. Our Compiler theme song is now under a Creative Commons license. Add your own special touch to our theme. Remixes have the chance to be featured on a future episode.