049: Navigating Career Growth: Expert Mentoring Strategies with Ritendra Datta

00:00 - 00:33 | Ritendra: In selecting a mentor, you also want to not feel bad or not feel low about yourself in the process. So you really need to know like what do you want to get out of it on the emotional side of things. Yes, you spend some time, you learn something very technical, something very precise, and you move on. You don't need to care too much about their personality, but if it's a more broader relationship you're trying to establish, find a mentor who makes you feel good. Because ultimately, more than half the people I mentor are not happy. And why subject yourself to even more unhappiness?
00:33 - 01:32 | Christopher: Welcome to Tech Careers and Money Talk, the podcast for financially focused technology employees. Are you working for equity? Do you have questions on how your career and money work together? Then welcome. Every week, we discuss strategies and tactics for how to grow your career, build wealth, and reach your financial and lifestyle goals. Welcome to this episode of Tech Career Money Talk live. Excited to be here with Ritendra Datta. You may remember him from episode 31, where we talked about his journey from a PhD to being a team leader and now being head of applied AI at Databricks. Well, we're back together today to talk about a very important topic, which is personal to both of us. We would not be here today if it wasn't for mentors. and if it wasn't for us, understanding how to be good mentees. So that's the topic today that we really want to dig into. And so Ritendra, number one, welcome back. Good to see you.

01:32 - 01:43 | Ritendra: Thank you so much for having me, Christopher, again. I mean, I'm so glad to be back chatting with you in person. It's it feels like it feels more three dimensional than the last time.

01:43 - 02:11 | Christopher: It really does. I got so much from the last conversation, but I always appreciate doing something like this live. And you and I are so passionate about mentorship. And to start that journey, I think the biggest question I get is, how do you position yourself as a mentee? So thinking back in your career and maybe the transition when you were starting your internship at Google, how did you start positioning yourself to find mentors?

02:11 - 04:05 | Ritendra: Yeah, I mean, first of all, I wasn't a great mentee to begin with. Becoming a better mentee took years, right? So now if I reflect back on what I did wrong, for example, at the beginning of my career was I did not proactively find a mentee. And that was a mistake. I pretty much now believe that if I had a dedicated mentee or a set of mentees at the early stage of my career, I would have grown faster in my career. So in hindsight, those who are starting out their career, you should get mentors. You should talk to them. You should build relationship. You should be super proactive about it. Now, That's what I didn't do. But if I were to do it again, what I would do is find mentors that can actually help me. I'm going to want to help them help me. So that's something that a lot of early stage mentees don't do. They think, for example, that you'll just find a mentor, the mentor will spend all their time and energy trying to figure out how to solve all your problems. The problems will go away. Someone will serve on a platter the recipe for success. I just follow that and it'll be like they, especially because a lot of people early in their career were students just before that. So in school, they're just going through syllabus, going through curriculum, going through course after course, and then expecting that that's all they have to do. Someone will give me a homework. I'll do the homework. I'll get better. I've graduated. The mentorship at work is quite different. You don't really have people serving you anything on a platter. The first thing a lot of mentors will ask you is, what do you need from me? And then a lot of people turn a blank, like they just don't know what to say.

04:06 - 05:12 | Christopher: That is such an insightful observation. And I remember that from our first conversation is that you observe and watch a lot of little details, which I really enjoy. And you're right, as we transition from university, we're programmed to go to professors for help, to go to the teaching assistants for help. And we're just on the curriculum. But when you're thinking about mentorship, you're going with a very specific ask. You want to be asking a specific question to solve a problem. And I like what you said at the beginning is if you can understand how to help your mentor help you faster, solve your problem, that will start generating momentum. And one of the things that I have found with mentors is that when they are able to solve your problems in a quick cadence, help you move forward faster, and they see you being very proactive in your responses, that momentum generates that nucleus that I think starts deepening the relationship.

05:12 - 06:30 | Ritendra: Yep, exactly. And I think that's exactly how you, so that's one part of that recipe of helping your mentor help you by creating a sort of energy around yourself. Hey, I want to do this. I want to do that. The mentor may not have been ready for that sort of energy. That's right. When you start being super energetic, here's my ambition. I had someone who was asking me, like, this is the beginning of my career. I just want to be the best in the world. Like, that's how they started their conversation with me. And I was like, that really influenced me. So if I was back to my early days of being a mentee, I would be like, this is what I want to do with my life. What can you do for me? But having said that, there's a big difference, because we're talking about university life, and then, you know, work life, and then being a mentee. A big difference between university and mentees, a lot of time when you find a mentor in your company, they're not getting paid for it. Whereas your professor has a bit of a financial incentive to do a good job with the thing, a mentor has much more limited incentive to do a good job of being a mentor. So that's why that relationship becomes much more of a shared responsibility.

06:31 - 07:43 | Christopher: It really does. And I'm glad that you went down that road because when you think about being a good mentee, there's a lot of value that you can bring to a mentor. And I was actually thinking about this on the drive over here is that one of the ways that I would always help my mentors when I was younger is just check in on them. And I know you're passionate about this, too. Sometimes it's just empathy. Like, how are you doing? You know, is everything going okay? Is there something that you have that I can help you with? Do you think, you know, when you are a mentee and you're trying to lean into your mentor and you're trying to ask for help, there's a great opportunity there to start adding value to them. That doesn't always come at first, but look for those little opportunities because, again, if you're bringing energy If you're coming with clarity of this problem that you want them to solve and then you're able to start helping them in some way, maybe it's just feeling better about the day, maybe they're not having a great day at work and you're able to be the person who is that empathetic ear, some of those small things add up to creating this momentum.

07:43 - 08:01 | Ritendra: Yep. Yep. And in fact, I think you meant to talk about the mentor asking the mentee, how are you doing? I would even turn it around and say, the mentee should also start to be concerned about the mentor. Hey, how was your day? No, that's what I was talking about.

08:01 - 09:15 | Christopher: No, because one of the things, and this is where I sometimes I guess we have to skip ahead in the conversation. One of the things that I do today that I keep in touch with my mentors is I realize now because we're all, a lot of us are dads or, you know, we're deeper in our careers. To keep in touch with my mentors today, I call and just check in on them. I mean, I will just, you know, I call it health checks. Like, how are you doing? Like, I'm here, like, let's just have a fun, maybe outside of work conversation. And actually maybe that is something of value that I realized right away is I'm somebody who I just, I'm a curious person. I'm just curious and I can, and this is why I love being a podcast host, because I get to know, really know a lot of different people and ask lots of questions about them. But, I can easily understand what somebody enjoys and just ask questions. Oh, did you did you cook that meal that you wanted to cook? Or did you go to Tahoe and do your skiing and just have a moment with my mentor to get them out of that headspace? That was one of the ways I realized that would start building momentum with my mentors when I was younger is just, you know, helping them, you know, have a nice day.

09:16 - 10:14 | Ritendra: Yep, yep. And I think that is something that sort of, it reminds me that very few times have I, as a mentee, asked my mentor, how are you doing? And very few times as a mentor, I have been asked the same. Because I think that relationship tends to be a lot more like one directional. What can you do for me? What can you do for me? But what can I do for you? It doesn't come naturally because there are many procedures. We don't ask this to our professors. When we are kids, we don't ask enough of that question to our parents. So whenever there's a hierarchy, we expect there is a one-directional relationship. So I think because the incentives are not that aligned in the mentor-mentee relationships, you have to do this a little bit differently. Definitely that's because then then it's a lot of times. They're just doing it, you know further for because they want to you know Help you out.

10:14 - 10:56 | Christopher: You have to do something to make them feel valued and this is one way to feel valued 100% and I do think that in let's formalize this right now is as you're moving from University and you are in industry and you're working to create momentum in, you know, mentee mentor relationships. Look for ways that you can lean into them. Look for ways that you can make it bi-directional. You may not always find it at first, but I think that those ways are there. Now, I think one of the other aspects of being a good mentee is, is looking and identifying mentors. So what is, what's some of the criteria that's important for you?

10:56 - 13:35 | Ritendra: Yeah, I think this is a great question. And it's something that's on top of a lot of people's minds. Like, what if every hour that you spend with the wrong mentor, you're both wasting time? Yes. Right. So I think what you're saying is like, how do you sort of optimize the mentor mentee time that you have on in both directions? Yes. So my, my general advice is to really study the, especially this is career mentoring. Study the career trajectory of the person you're targeting to be your mentor. Do you like where they went from where they are now? Do you like how they led their life as best as you can from their LinkedIn or from their resume or from their website or portfolio? Whatever it is that you're looking, is this someone you idolize? There could also be some specialty reasons to pick a mentor, which is, let's say, a person made a very specific career switch. Even though the rest of their life and career is quite different from yours, a very specific, like a classic one I've been seeing a lot is, a lot of people want to move from infrastructure engineering. I'm an engineer, so I think a lot about engineering. I talk to a lot of engineers. they're moving from infrastructure or product engineering to AI because AI is so big these days. Everyone's like, how do I pivot to that? So they would look at some of our profile and think, hey, you made the pivot. Usually, if they tell me that, I usually say, no, I did not make a pivot. I was always an AI person from undergrad. or even earlier as I was tweaking, playing around with this stuff. But there are others for whom that switch happened and it looks successful in terms of their career path. So that's one special reason. But if you want to have a more long-term mentor-mentee relationship, pick someone for whom there's more in common, not just that one career switch. They took a career break, they became financially independent. I would idolize you as someone like, someday I want to be financially independent and not have to work. I hope my bosses are not listing. But it's a great, I mean, looking at your personal success story, if that's something that appeals to me, by the way, financial independence, I hear that all the time. Everyone wants financial independence. They don't know how to get there. So they look for mentors who have been there. So even you are a great example of a mentor for someone who's looking for it. I wonder if you have anything to add on that.

13:36 - 16:02 | Christopher: Yeah, I do, because I, you know, I always go back. One of the things that you always like to share is where did you fail early on that led in that direction? And when I was working for Accenture, there was somebody who, you know, because when I look at mentors at first, the first thing I focused on was their skill, because I really wanted to build deep technical skills because I knew that when I had those, then I would have leverage. And there was somebody who I admired. And so I approached them. We had conversations and I started helping them on a project. And I started realizing that while they were incredibly technically gifted, they were somebody that was just not nice to be around. They weren't that well-rounded person. We've seen this, right? And it's out there. And so that was really, you know, and I ended up sticking with that person for a good year, year and a half. And it was one of these, I was, you know how it is when you're young in your career and you don't know what good looks like. You can stay in these points of pain and frustration and you don't understand why. And then I started picking up a second mentor because I wanted to become a better leader and a better manager and this person was incredibly empathetic and this is somebody who is a mentor to this day. And he just shared with me, he said, You don't have to be a mentee to somebody forever. You can learn something from them. And if you've experienced it in that season, you can move on. So number one, I realized I had the permission to move forward. And then from that mistake, what I realized, Ratendra, is that I needed to look at that holistic picture. Who is that person as a technologist? Which is very important. There's so many things to learn from people on the technology side. And then who are they as a person? How do they present themselves in the world? And then there is this aspect of who are they as a leader, right? And sometimes it can be an individual contributor, but they have high influence. But those were the things and those are sort of the three factors that I continue to look at to this day because I think that mentorship is truly an accelerator to your career.

16:04 - 17:55 | Ritendra: That makes complete sense and yeah that's a great segue into like one of the things that I was thinking of which is how nice the person is, should be a factor and it should be related to how long you expect to be in a mentor-mentee relationship with that person because If they're not nice to be, you should be careful. That's why it might make sense to make an early judgment. You don't know how much depth you'll get out of them, but you can tell if they're going to be nice to you. They're going to make you feel better or not. But there are times, I think this is all a trade-off, like everything in life is a trade-off I learned from a colleague of mine. The trade-off here is there could be some genius who can teach you something and you can tolerate them for a small period of time, but then you have to move on like what you said. So in selecting a mentor, you also want to not feel bad or not feel low about yourself in the process. So you really need to know what do you want to get out of it on the emotional side of things. If it's purely technical, someone is the only person in the world studying some nano fabric or whatever. Yes, you spend some time, you learn something very technical, something very precise, and you move on. You don't need to care too much about their personality. But if it's a more broader relationship you're trying to establish, find a mentor who makes you feel good. Because ultimately, more than half the people I mentor are not happy. And why subject yourself to even more unhappiness? I didn't mention that, but you brought that up. How nice are they? Test them out. Spend some time and be prepared to just walk away and say, I don't think this is working out.

17:55 - 18:32 | Christopher: Well, and I think it reminds me of that old adage as we're talking, they talk about friends, you're friends for a reason, you're friends for a season or you're friends for life. And I've found the same thing with mentors as well, right? There is that reason. And I also think that there is sometimes a season. Maybe you're at a company and you're working together at a company during that period of time. And then there are those special mentor relationships where you know you're going to be talking to them and sometimes you don't talk for a year or so and then you touch base with them and it's just you pick up where you left off. And those are super, super valuable.

18:33 - 18:57 | Ritendra: Yep. Yep. Agreed. Totally. So, how do you, like, when you became, like, experienced, right? I have a question back to you, right? Sure. 15 years, 20 years into your career or whatever, when you got really good at it, do you continue to build new mentors? Like, that's a question I have, like, do you sort of, is there a budget? Like, how many mentors can you have?

18:58 - 21:34 | Christopher: Well, I do, I think that there is a, as far as like active mentors, I think that there is a little bit of a budget because it takes time and commitment on both sides to really have that deep relationship. And I think that as I have continued to grow as a person, as I've continued to grow in my career, I do, I always seek mentors. And I think I was influenced because when I was younger I had my maternal grandfather live next door to us and he taught in high school basic arithmetic and carpentry and shop and he was always just taking me under his wing and showing me things and I just realized that my life was so much more rich because of the things that he taught. And so now, so now I'm seeking mentors who are on the boards of companies or mentors that are very experienced venture capital investors, you know, things that, you know, I am in my nascency and I'm moving forward and trying to experience more or experienced private equity investors where, I mean, that's where I spend, you know, time on the investment side. And I think probably five to seven is really – I think seven is stretching it from a mentorship perspective but I think having around five. And I also think now also as a father I've changed some of the dimensions so it's not just all industry specific but people who are further ahead on the on that journey as well. But I do, and I think I look around, and I look at where I am, and I, one of the things that, and I think this is a component of it, that even going back to the beginning of our conversation, is the clarity, is where are you headed, what do you want to learn, and where do you see your deficiencies? Like, I just don't know this, or I haven't had that experience. I think that helps me look around. And then now, as I vet the mentors, I do a lot of looking online and trying to understand if I can see visibility and profile. And then, and to your point, I will go in straight away and try and, you know, vet and understand fit. Because as we've been through this process before, I mean, I'm sure, and I'll turn this question back to you in a second is, as you're looking and finding mentors today, I'm sure that your process of vetting them and understanding, you know, if there's going to be a fit is probably a much shorter timeframe.

21:34 - 23:19 | Ritendra: Yeah, it is for me. Yeah, yeah, yeah. I think like the fit for me at this point, like, The mentorship, finding a mentor and finding out if the mentor is going to stay on for a long time happens very quickly. It's because we've built the instinct around what works, what doesn't work, have I exhausted learning everything about this person. Right now, I have a mentor who is much older, but was very successful in the startup environment in the Bay Area. And at this point, he is primarily, one of the things he does is he actually mentors a bunch of people and encourages them to take their companies public and so on. He himself took two companies public. his career and he's always like, it was really surprising. Day one, I was chatting with him through some connections and like day one, he told me some things I hadn't heard for the last 10 years. Like, hey, you're not being ambitious enough. No one had told me. Everyone's like, oh, you're doing so well. And he's like, no, no, no. you can do way more. Like someone who takes, who just changes your very assumptions about yourself is usually a very good mentor because, and this is just a prelude because if that's the day one, date seven will look even more interesting because they'll learn more things about me. I'll learn more things about them and they'll tell me, here is how you can do it. First, they'll say, okay, you're not being ambitious, but I know that there's more coming. Okay, let me tell you, here is how you do it.

23:19 - 24:19 | Christopher: Wow. So I think that is a very, very important point that we need to tease out is that, If you're in a relationship, good relationship with a mentor, you're going to feel uncomfortable. And that's what we seek. We're at this stage right now that we want people that are going to do two specific things, for me anyway, is look in my blind spot. What am I not seeing? I want to give you all of the data around who I am, where I'm trying to go, what I've accomplished and done, my skill set. Help me understand my blind spot. And then tell me some of the things that people may not be telling me. Because it's easy when you experience success that you do get a lot of attaboys, but you do find working with mentors that get you uncomfortable and have you challenging your own thinking, it's an incredible growth place to be.

24:19 - 25:46 | Ritendra: Yeah, yeah. And they have to balance it out with compliments, right? They can't just be like, you're nobody. That's right. That's right. You are somebody. The thing is, you set a baseline by appreciating the person. And then you say, yes, you're great. You need to be greater. I want to make a somewhat interesting, controversial point about when this because I do think that there are some cases where you, and this happens all the time in music for example, right? You have a, you're a disciple of a musician like, and you're sort of learning, learning. This could be any other kinds of like long form like, you know, art that is, that lasts for a long period of time. You have a you have a guru, there is many, many documented histories about disciples getting better than their mentors or teachers. And that's creating a sort of rift and a sort of a complexity that is unanticipated at the very beginning. And so that's one thing to watch out for. What if you start to become more successful than your mentor? Yes. How do you deal with that? What can you expect? I think it's an interesting one. It has not happened that many times. But when it happens, it creates a lot of unease, a lot of discomfort, a different kind of discomfort.

25:46 - 26:48 | Christopher: It does. No, it creates a different kind of discomfort. And I know I had some relationships like that or it's interesting I mean so one of the things I think that's interesting you know from my perspective is I've had some relationships change over time because I had some some people that were career mentors and now that I chose this other path to seek the financial independence and now I've stepped outside. Now they've come around with great respect in a very complimentary way saying, OK, now I'm looking for help over here. And they've sort of flipped the script, which I'm very, very open to do. But I do think that I do remember a couple of points in my career when I started making some progress and other people were sort of had been my mentors, were sort of Not left behind, but their career wasn't moving as fast. There were definitely some awkward conversations.

26:48 - 27:21 | Ritendra: Yeah, and I think that requires the mentor, this is a mentor question, but it requires the mentor to not have ego. To switch sides, you have to be comfortable. being on the other side, right? A lot of people are not… So this doesn't come naturally to everyone. It doesn't. It's a really good point you made, like, you know, those who are able to, like, say, you know, I helped you, now you help me, and I'm totally fine with this. They're probably also good mentors.

27:21 - 29:00 | Christopher: That's right. They are, because, well, and it goes back to the whole conversation of, You know when you select a mentor I think for me one of the key things is finding somebody who is self-aware, right? Who understands and knows themselves and if they do they're going to have an internal survey of strengths and weaknesses and completely understand that. Oh, now you're developing in this area over here that I don't have the strength in. Okay. You know, hey, I could use some help in that area. Would you be open to questions and all this stuff? Of course. Happy to reciprocate. But I think we've spent… this first half of the show on what it takes to be a mentee. I think we've covered a lot of good points. What we're gonna do is we're gonna take a short break, we're gonna be back, and then in the second half, we're gonna really focus on what it takes to be a good mentor. Okay, and we are back with part two here, Tech Careers and Money Talk. Ratendra Datta, being a great mentor. I want to start off because one of the impetuses for this podcast, and I was coming up to the Bay Area and I saw a LinkedIn post. of it looked like people just that you posted that you were talking about some mentees talking about horrible mentors. And it just made me realize, like, so many people don't understand how to do this right. And so what helped me understand, bring out, you know, what were you hearing from people? And what do you see right now is potentially some of the issues here that we should talk about?

29:00 - 31:16 | Ritendra: Yeah, I think like Most of them don't call their managers mentors, but I think most of them are complaining about their managers. But managers are mentors, right? They are. In some sense, these folks are complaining about a certain type of, a special kind of mentor, which is your manager, and your skip-level manager. A lot of the aren't in a great relationship with their managers and skip-level managers, so in the sense that they're not doing their duties of being a good mentor. And the most important thing that's common between any mentor and a manager is empathy. Step one is listen with empathy to your report or your mentee. So as a mentor or a manager, I don't think it matters. I just interchangeably use mentor and manager because I think they're related. You have to intently listen to what problems your reports are facing. Too many managers are basically saying, I don't have time for this. We need to do this. Oh, you have a problem? I don't have time for that. This is not important. I don't have enough bandwidth to help you out. Oh, here's a little sort of a, let me throw you a bone and maybe that'll solve the problem. But all they had to do was listen intently to their problems, seek to understand. Again, I go back to Stephen Covey. first seek to understand, then to be understood. So again, we come back to our friend. It's impossible to give your inputs before you have listened. And that's so basic. It doesn't cost anything. That's what I was saying. My post was specifically about the absolute basics of, does my manager even listen to my problems? Does the manager understand step two? Does the manager plan to do anything about it? And step four, do they actually succeed at doing that? I mean, step one, I'm stuck in step one. That's right. Yeah, the other ones could be hard for various reasons. But how about just listening and nodding your head like this is not hard. Even that seems to be not that common.

31:17 - 34:08 | Christopher: Yeah, I mean, this is such a challenge in technology. We move fast. We do. And I also think that there is there's a lot of skills that are not taught to first time managers. And it's so hard that once you don't have these skills, I think it's hard to recover as you start growing and scaling. I think that people aren't taught, you know, managers aren't taught how they need to protect and manage their own time so they can be effective managers. And I think to be clear, what our experience has been in our career is that if you want to be a great manager, you have to be a mentor, period, full stop. And I think it's important that people understand that as your career ascends, if you are not a great manager, two things are gonna happen. Number one is there's gonna be a reputation that people don't wanna work for you. all of a sudden you will start getting a drag on your career that you're not getting these great positions because it's hard to hire because you have a name and reputation. And then on the flip side, when you get to director and above, it's not just your manager who decides on your promotion, it's all the other executives. And so if they hear about how you're not a great manager, that again is going to create downward pressure on your career. And so I literally, the episode that is going to release before this one is a woman named Erin Deal who wrote a book, Radical Empathy, that was sort of an offshoot of Radical Candor. And the simplest thing she said is that if you want to show empathy when somebody says what they're experiencing, you just literally just read back the problem in sort of the I statement. So you sort of say, I am feeling this, like you're just literally trying to read it back. Just that simple step can make that person feel understood, release that level of pressure. And I think people don't always understand, they think that, again, you've drawn something out for me in this conversation that will now influence my writing going forward, I'll let you know, which is the fact that we get programmed by university. We do, and university is, there's financial motivation, there's more of a intellectual transaction, but when you get into industry, feelings are involved. Feelings are involved, like if I'm gonna put money in your pocket, you're gonna feel incredibly happy. If I'm taking money out of your pocket, who knows what you could feel, angry, sad, frustrated. But all along the part of that journey is helping you manage your career, which means that we need to build psychological safety and emotional trust. And I think empathy is definitely the foundation.

34:08 - 35:59 | Ritendra: Yep, yep, absolutely. And I think the thing that you just mentioned about how, like my step one was to seek to be to understand this, I think there's a step 1.5 there of reflecting back so they know that you you're understanding this. So I missed that step, and the lady you're talking about, I think that's a fantastic idea. Repeat back, and do it in a way that they really feel like you're embodying their pain. And that's real empathy, because you can always repeat, or even just the use of the word I. saying it from your perspective is even more real. It's like, okay, you're embodying my situation, and now you see things from my point of view. So now I can trust you to solve my problem. Because when I've started mentoring, one of the things I observe is the first 5-10 minutes, my mentees keenly evaluating me. That's right. trying to understand if I'm any good, if I'm going to add any value to them or not. And when I am able to repeat their problem and it's accurate, that's when they start to trust me. Before that, they're like, you're here. You have some credentials. You're here to just give me some lecture about how to do things. And they realize I'm not interested in impressing anyone. I'm not interested in lecturing anyone. I'm just here to solve your problem. That's how I start every conversation as a mentor. And that's where I end. I don't talk about myself except absolutely necessary to map to something that they might be facing. When I fail to do that, that's when I lose my mentee. So I think that's a fantastic input.

35:59 - 36:59 | Christopher: Yeah, I really think that radical empathy, it really stuck with me and I was trying to look for what is something clear and concise of how you can just generate that. Because, and this goes back to, so I think we're really on the topic of what makes a really solid mentor, and it is creating that emotional relationship where somebody can feel safe to share with you. Because a mentor, and this is where, let's dispel some myths here, like a mentor relationship You're not just teaching somebody a skill, you're walking with them alongside their career. And I think they're going to get much more value when they know I can trust you and they know that they can bring anything to the table. than if they don't, if it's just this very sterile, oh, I'm teaching you how to do X, Y, and Z. Yeah.

36:59 - 39:15 | Ritendra: And actually, that made me think about something. There is a risk. Here's my fear of becoming a bad mentor. When I've seen enough different cases, there's a risk of in those first 5, 10 minutes of meeting someone, to map their situation to one of the situations you've seen in the past. Let's say, oh yeah, I've seen this, here's what you should do. I've had a lot of bad mentors who are not officially mentors, people who love to give me advice, who very quickly jump to a solution. Like, hey, here, oh yeah, I've seen this. I've seen in this past, oh, I know some people, here's what you should do. This is where they lose me. That's right. Or I lose them. I don't know which one. People are lost. My biggest fear is that I'll become that kind of a person where I've seen enough density of different variants that I'll no longer. But so my counter to that is I firmly believe, and already in that 60, 70 people that I've talked to in the last two weeks alone, there's so much variance, even within a cluster of very similar problems, that you really need to pay attention to the details. Because otherwise, as a mentor, you will start to map very quickly to some other person or some other situation, and you'll give the wrong advice. So listen to completion, and at some point, you'll be like, no, no, no, this is interesting, this is different. This is slightly different and that slight difference in this person's situation is hard. One very simple thing I've started doing, take a pause. If I take a pause, it's like AI model. I'm taking new input. Every single input is valuable in and of itself. I'm going to take it and absorb it. I'm going to take some time to imbibe it in my neural networks. and then give advice. Take the pauses both figuratively is a good thing in that you're listening intently, but it also gives you time to process what you just heard. So you don't do that mapping thing, because that mapping thing is very dangerous. You're going to end up giving some vague advice, some generic advice to a person who's dealing with a very specific thing.

39:15 - 39:35 | Christopher: And I agree 100% and I think that, you know, people want to know that you're solving a unique problem for them. Number one. Number two is people don't like just canned, you know, not that we'd be unsolicited, but they just don't want canned advice. Right? They want to know that you're really understanding them.

39:36 - 39:54 | Ritendra: And in fact, that is why they're even seeking a mentor. Because if it was generic, they would have read it in a book. They would have heard it in some lecture. Maybe they'll just listen to this video and be like, oh, now I know everything. The generic advice only goes so far.

39:57 - 40:31 | Christopher: Well, and this is where I think that as we're talking about being a great mentor is really, you know, you're helping people sometimes navigate this intersection, right? As knowledge workers, we have all this knowledge, but it happens in our brain and work involves so many emotions as well. And we're helping them navigate that I guess you could call it a minefield. But that very challenging puzzle sometimes to solve, to get people to progress. And there's a lot of unique patterns. There's a lot of snowflakes out there.

40:31 - 41:17 | Ritendra: There really are. There are. And then you start to, at some point of time, you start to see the periphery of all the different types of situations you've never seen. That's when you actually benefit as a mentor, where you learn something. The situation is so unique. a mentee can teach you to handle a situation. And so here's an interesting one, right? So someone describing to me this situation, and I'm like, okay, here's what I would have done. And then they say, before I could even say that, they'll say, and here's how I handled it. Like, that's better than what I would have told us. Yeah. Suddenly, like, it's a nugget. of knowledge that I learned from the mentee, the first conversation, first 20 minutes of the first conversation. That's amazing. Like there's something for the mentor too, right?

41:17 - 42:05 | Christopher: Oh, there is. I mean, this is where, you know, touching back on our earlier conversation, right, where we are encouraging mentees to look at it as bi-directional. But the reality is, is that for mentors, being a mentor does provide tremendous value because it allows us to, if you're mentoring outside of the people you manage, you're then getting a broader pool of data and you're gonna be able to be a better manager because you've seen a lot of different scenarios to deal with. Number one, you're also gonna have much more practice. You have much more repetitions. That's gonna help make you better too. and you then get this constant feedback and you get ideas.

42:05 - 43:03 | Ritendra: Yeah, that's a great point you made, which is like the mentor has a more diversified perspective than your manager, if they're not the same person. Because they're talking to so many different people, the manager working with the same set of people over a long period of time could actually be stuck in a local maxima in what advice they can give, what solutions they can provide. The number of times I've heard people say, oh, this is new. I had never thought of it like that. You have a manager. You're talking about a manager problem. that manager has not told you something that this mentor told you within 20 minutes. That is the diversity at play here. I'm not taking credit. It's just simply talking, like working at different, this is why experience matters. It's the same thing. As a mentor, the more experience you develop, the more useful you're going to be at but randomizing in a good way the thought process of a mentee.

43:03 - 43:27 | Christopher: Then it's also the value of diversity as well. Going and saying, I'm going to support different groups and I'm going to mentor into different groups that may come from different ethnic backgrounds or multicultural backgrounds. All of that stuff is just phenomenal input that makes you a better mentor, which can lead to being a better manager.

43:27 - 43:53 | Ritendra: Right, right, exactly. And I think that there's no shame in if you have shared ethnicities or shared socioeconomic backgrounds, to leverage that as a mentor to be more relatable to the mentee. I think there's nothing wrong with that. We all sort of come from different backgrounds, and we have strengths. And it's a bit of a specialization, but it still is something that is not to be ignored. If you know something, share it. 100%.

43:56 - 44:05 | Christopher: So moving off of the empathy, sort of the emotional side, what are some other characteristics that you think help make a great mentor?

44:06 - 49:01 | Ritendra: Yeah, I think just the knowledge, knowledge is a very big part of it. I think, for example, if you don't know what you're talking about, it's such a simple statement. If you don't know what you're talking about, the mentee will know that you're making stuff up. So be very direct and honest about the boundaries of your knowledge and experience, and talk within those boundaries. Don't talk about things, because I'll give you a classic example, AI. Everybody on LinkedIn, since we are both on LinkedIn, everybody is an AI expert right now on LinkedIn. Everyone is saying, oh, the cloud is better than Antropic, is better than GPT, is better than blah, blah, blah. Oh, what times we are living in. I love those conversations. Just for fun, I sometimes go into these detailed things. these people have 100,000, 200,000 followers. They call themselves, they're self-proclaimed AI experts, and then somebody publishes them as top minds in AI. So that sort of reinforced each other. And then when I look in depth at their conversations, and I see gaping holes in their understanding of what they're talking about. So knowledge, especially in fields that are emerging and exciting, don't fool your mentees into believing that you know what you don't. Just be honest and direct. I don't know why, but I think we underestimate the intelligence of people around us. I think people just assume that they can just fool people. But I've noticed that even on LinkedIn, over periods of time, people are very good at gleaning Genuine, authentic knowledge versus like, I read something somewhere and I'm regurgitating it here, use JAN-GPT ironically to make it look like well-formed sentences on a topic. Just don't do that. So that's one. So knowledge is a big one. The other one is, I think you already covered diversity. You should diversify yourself as a mentor. Talk to different people, different backgrounds, different ethnicities, different countries. I was saying, I've talked to people from four different continents, probably 10 different countries, all sorts of companies, big, small. companies at different stages of their success, people with different backgrounds, tech typically because that's the bias that exists in people who come to chat with me. So that diversity, you can take it to the next level and really proactively create diversity for yourself as a mentor. If you have only so much time to give to mentees, don't accept mentors who are too similar. You can say, maybe you can learn from somebody else. You can build your skills as a mentor by just talking to different types of people, different types of backgrounds. That proactivity, I've never heard anyone say that, but I found that to be a useful one because it also makes those conversations interesting. After a while, if you just see the same pattern, hey, I'm in this thing, I want to be AI. After a while, you get bored. If you get bored as a mentor, that's the end because you will not be a good mentor, you're going to lose. So keep it interesting for yourself. So diversity is one way, the other way might be like, you know, take on new challenges of mentoring people. I have mentors, I have mentees now, who are much older than me, who have much more experience than me. They're coming and I'm like learning from them, but then I'm able to help them in certain parts. But at the same time, learning from them and I'm seeing what kind of resilience some of these people have. It's amazing, right? You know, they've been They've been tolerating bad companies, bad relationships, bad managers for so long. And I would have given up so much more easily, but they did it for their family or whatever other constraints they had. So those are some of them. I don't think I have a full structured list, but if I were to repeat it, right? Of course, empathy, knowledge, the diversity of opinions and thoughts. And then, you know, be keeping it interesting. So those are the energy. Oh, yeah. I think energy is a good one in and of itself. Right? Don't be a mentor if you don't have energy. That's right. It'll just drop the energy of the conversation. And people will perceive that as, this person is not interested in helping me. So it's problematic if you have empathy, but you don't have energy. So then, I want to help you, but oh god, I need to go to sleep. So that's something to avoid.

49:01 - 50:42 | Christopher: No, you do need energy. And I think, you know, and when I think about, you know, the functions of a mentor, I think the goal is you're trying to help people understand and guide them along this path and lets them know what works and what doesn't. So I think being transparent about the things that didn't work for you, being transparent about the things that didn't work out and why. I think that builds trust as a mentor. And I know that this is something that you're really good at, right? Is when you go into examples, I wasn't the greatest at first. Let me walk you through why that didn't work. Let me now show you how that's a lesson learned. and here's how I chose to move forward. Just reciting that back, that's one of the things I think about in mentorship is being able to articulate those stories and about here's what worked for me, here's the lesson that I learned. And you're telling it from this eye perspective. versus you should do that, I did this, you should do that. When you're telling it from that first person perspective, it makes it very personal. And our jobs and the role of mentor is really to share our personal experience, the lessons that we learned from it, the strength that we got from it in our personal way, and then asking, what did you get from that? And asking the questions, what can you take away in a very, conversational way, I think that's something that I found when you're able to mentor in that perspective in some of the capacities that you just talked about, I find that that's very, very, very helpful.

50:42 - 52:38 | Ritendra: Yeah, I just remembered that's a really good point. And I also remembered one other thing, there is a bit of a generalization of some of the things you said, which is by your own bias as a mentor, you're going to come in with your own biases. That's right. And especially the unconscious biases, you have to like be extremely self aware. By the way, that's related to empathy and everything else. But self awareness is very important. Like, where are you coming from? What are your biases? You just looked at this person resume? Where did you judge this person? How can you fight your own judgment of this person? For example, you think someone is being way more ambitious than you think they will get to. How do you not be biased by that? You've made a snap judgment that this person is shooting for the moon, they won't get there. If you have that sort of thing, you're probably wrong because you should never underestimate your mentee. So how do you sort of leave your biases, and also other kinds of biases exist. We have all kinds of biases in our head and we're approaching the person with those, but how do you leave those outside? That's number one. So how do you fight your unconscious biases? Number two, I use this a lot, sample size one opinions. It worked for me, or it worked for Steve Jobs, or it worked for Satya Nadella, so it should work for you, or anyone. It should work for anyone. Any one or two data points is almost never useful. how do you fight that small sample size bias that we all have? We just saw this one instance of success or failure. So I'm inclined to tell you that don't do it because it might happen to you. But if you have sound statistical judgment, you will not do that. So funnily enough, a mentor needs to know basic statistics.

52:41 - 53:04 | Christopher: Well, we've gone through a whole list of a lot of things that mentors need to do, which I think is so important. I think people need to hear from us that we've had a modicum of success with this and this is something we're passionate about and continue to do. But let's sort of bring it home by talking a little bit about what are the benefits that you get personally from being a mentor?

53:04 - 56:48 | Ritendra: Yeah, so I think like for people at my stage of career, financially, it doesn't make sense, usually, right? Because, you know, if I just spent that amount of time doing my day job, I would, it's, it pays way more, right? I think if So maybe at some point or at some level, some people have reached a stage where it starts to make financial sense. That's not for me. It's not why I'm doing this. I just felt that building a legacy around sharing what I know is what I'm after at this point. So if I can help people like that moment of seeing the change in someone's face from Oh, I did not think this way. That's very interesting. That by itself is worth it. Because a lot of people are struggling so much to just develop clarity about their own career. and not getting anyone to tell them. When I tell them, so here's an example, a simple example. Someone says, just talking to me about the details of this, this person said this, this happened, this happened. And after listening to them for like 10 minutes, I said, I think you're in the wrong team or wrong company or some dramatic thing. And they're like, I hadn't thought of that. You're right. So that's it. That is when I feel like, and I'm assuming that I'm right about it. I don't want to like, assuming that I'm right about it, that is what I get the most out of it. Then there's, of course, learning. I learn from mentees a lot because they have so much. Lots of them have more experience than me. They're nicer than me. They're smarter than me. There's so much I can learn from people. That relationship is purely based on some specific things that they thought I was better at them for. But there's so many other aspects to a life. I can learn so much. I'm inferior in probably every other way. So I can learn from that experience. And also, I think there's a little bit of feeling good about doing something good, which I think overlaps with what I just said, but it's just like, I'm not doing social service. I'm not actively doing social service while I'm Employed full-time. This is the closest to social service. I can do for some subset of this the community I'm not you know this I'm not helping the poor or the lady in that sense But I'm helping people who are clueless and there's they're like emotionally. They're completely many of them are extremely drained out and And I give them a little bit of energy boost by chatting with them for some time. And that to me, like genuinely, that's it. That to me is the most important part of it. Like nothing else comes even close to the value of feeling like I changed someone's thought process a little bit. Because I know that that creates a ramp, and then they'll take it from there. They're smart. Most of the people I talk to are really smart. They get it. When I tell them, they get it. They're not struggling to understand what I'm telling them and why I'm telling them what I'm saying. They get it. They process it. They're going to also, by the way, know where I'm wrong in my advice. They'll be like, yeah, he's like 80% there. I'm going to take that 80%. I'm going to ignore 20% of what he just told me to do. But that alone is good enough for them to get better because they're not going to 100% listen to me because they're smart enough to know I'm not 100% right most of the time.

56:50 - 57:59 | Christopher: But they need that going forward and I think, yeah, mentorship, I think number one, you know, and I just, I'm going to read back what you said because I personally believe this too. I personally believe this too. I know you do. I know, this is where we're kindred spirits here. In our community of technology employees, many of us, we didn't come from anything. I mean, obviously we have the ability to have these great careers, generate great income from working from technology, but I know plenty of people who immigrated to this country and had nothing. and now are doing very, very well, and they have mental health issues because this industry, as sexy as it looks from the outside, can be brutal and unforgiving because we're expected to, you know, depending on the role, you think about like reliability engineers, you can have a 24 by seven lifestyle, depending on the size of your company, you know, and customer expectations are high, competition is high, we move at speed, we solve difficult problems, and those are just the table stakes.

57:59 - 58:01 | Ritendra: And we had 40,000 layoffs this year.

58:01 - 59:45 | Christopher: Yeah, exactly. And you don't even know what's coming, right? You have layoffs. You have financial uncertainty on top of all that other stuff. Then you also have home life. And then on top of that, you're expected to then navigate your career through something that is constantly evolving. So I believe and this is why I started this podcast is I want to create a space where we can talk about the fact that we need to take care of each other's mental health. We need to provide advice and this is what I get out of mentoring too. And it's just the reality that when you see somebody get unstuck, and I just think recently I had a mentee who had moved to a new company. She's really aggressively pursuing a director level role and I was really trying to help her get ready for an audit committee presentation. And she just needed some run through, she just needed some confidence. I mean to your point, incredibly smart, skilled, but she just needed somebody to take some time, give her the confidence, give her some pointed feedback, tuning, so that she could go in there. And when you get the note, oh my gosh, it felt amazing to be in there. I saw their eyes on me. I knew they understood what I was saying. I felt all this, the things that she always wanted to feel. It's that moment where it makes it worth it. You know what I mean? And it's not about, I appreciated that, you know, she obviously, you know, thanked me and was very generous with that. But for me, seeing her succeed, seeing her navigate through and realize that she's got a lot of that stuff.

59:45 - 59:51 | Ritendra: Yeah, I mean, I think that's the heart of it. Everything else is sort of noise.

59:52 - 01:00:45 | Christopher: Well, it is and it isn't. I mean, let's talk a little bit because when you are doing that, let's say as you're managing a team, I mean, there is a, I mean, and sometimes I think, you know, talk about bias. We can get biased because we've been mentoring, we're passionate about it, we love to do it. And I've created lifelong friendships around mentoring, but there are tangible benefits to your career. If you are a great mentor, if you're a manager and a mentor, you will attract people to you. They will follow you from, talent will start following you. And if you are able to create that environment, that will help your career ascend. I, you know, and I'd be curious to, but you know, the managers and the people that are out there that attract great talent, they can then go and move to different companies and do great things because they know that they're going to be able to assemble a team in no time.

01:00:45 - 01:01:18 | Ritendra: Yep, exactly, and I'm benefiting from that right now as we speak. I've had people from Facebook and Google where I used to work now work with me at Databricks. That's a privilege because I think somehow my mentorship as a manager kind of worked in the past. they trust that I will take care of them, and I'll support them, and I'll help them grow. So that's the trust with which they've come along on the ride. So yeah, I completely agree with you.

01:01:18 - 01:02:09 | Christopher: And then when you build also, when you build a strong team that's very, very well mentored, like they take care of each other. Yes. Right? And then you get into this situation where a lot like When I think about the teams that I ran, and I think about Splunk specifically, just because I was having a reunion with some colleagues, is we would make sure each other got rest. We would have those conversations. Hey, where are you on the scale? Why don't you go take three days off? We've got everything. Don't even worry about it. Go take a mental break. We would make sure that we created this environment that we would take care of each other's mental health. And I think you know, teams that are mentoring and nurturing and caring for each other can, you know, help protect each other in these types of harsh environments.

01:02:09 - 01:02:27 | Ritendra: They start repeating the mantras, the messages. You know, if one of them likes a message or a way of thinking, then they start repeating. You don't even have to be in the room. What would this person have done in this situation? Now the spirit is in the room without you being in the room.

01:02:28 - 01:03:24 | Christopher: It is and I think one of the one of the greatest joys of mentorship is when you see one of your mentees become a leader and then they they are they may not repeat these things in the same way but they're building teams in the same way because this is ultimately why we do this right is to continue to create a very healthy culture doing the thing that we love. We love technology. Front row seat to the future, right? On the bleeding edge, right? We talked about that last time. And if we can mentor people well and create good and healthy teams that support each other in the midst of all this, then I think that, yeah, who knows what we can achieve. Cool. I think that's our mic drop moment. I also think that you're going to be turning into a pumpkin. So do you want to give people just a quick update on your mentor program?

01:03:24 - 01:04:49 | Ritendra: Yeah, I've been overwhelmed with mentoring requests. But I'm still, you know, I mean, depending on the situation, I think really like the judgment call I'm making is who needs my help the most. and prioritizing people like they get to our mentor crews. I'm on mentor crews and I've had many, many people talk to me. I love the platform and I love the fact that it's got a well-supported set of tools so you can apply, you can give your situation. I'm making a judgment call because my time is fine limited. I'm doing it on nights. So there's only so much night time I have. But if you have a situation where you really think you can map your situation to someone like me parsing that situation and being able to help, please write over there and I'll do my best to help. A lot of the mentorship is one-off. That's good enough. You don't need a long-term mentor. You just need one conversation, someone to tell you differently. That I think I can scale up a lot more because then I don't have to keep talking to the same person. I just, you know, chat with you. I have this one good, meaningful chat, and maybe it helps you. Maybe it doesn't, but you can give it a shot. And I think I'm much more open to, like, one-off chats because they're, you know, they're sort of more scalable. And given the time I have.

01:04:49 - 01:04:54 | Christopher: Great. Well, I'll make sure and put that link in the show notes. But thank you so much, Ratendra. I appreciate your time.

01:04:54 - 01:04:57 | Ritendra: Thank you so much, Christopher. Thank you. You're welcome.