How to Find a Mentor and Become One: Mentoring Strategies for Tech Careers | Rahul Jain
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Show Notes
Struggling to find a mentor — or wondering how to become one — in a fast-moving tech career? In this episode, Rahul Jain, a senior solutions engineer and data/AI leader with 15+ years driving enterprise data transformations and a career arc from mining engineering to data engineering and leadership, walks through practical mentoring strategies for tech professionals. We define mentoring (purpose, scope, types), explore early models like Thoughtworks’ sponsorship, and show how to find mentors through networks, platforms, and cold outreach — with concrete outreach best practices: specificity, background, and follow-up. Rahul covers preparing mentoring sessions (goals, agendas), mentoring formats (one-off advice vs long-term relationships), and how to start as a mentor using simple first steps and platforms. Topics include benefits of mentoring, transferable workplace guidance, developing people skills (empathy, listening), balancing technical work and leadership, tackling imposter syndrome, coaching vs managing, setting boundaries and paid mentorship, and maintaining development plans. Listen to gain actionable steps, templates, and mindset shifts to both secure meaningful mentorship and build a sustainable mentoring practice in your tech career.
Today we’re discussing mentoring with Rahul Jain, a technical leader with about 20 years of experience building and running software products. He currently leads the Business Intelligence and Data Engineering units at Omio, a ticket-booking company, and mentors engineers and managers through The Mentoring Club.
We covered:
- Background and journey
- What is mentoring?
- Experiencing mentoring
- Finding a mentor
- Benefits of being a mentor
- Mentoring beyond your domain
- The Mentoring Club
- Preparing for mentoring sessions
- Common mentoring challenges
- Learning people skills for mentoring
- Balancing tech and leadership
- Q&A from the Audience
Background and journey
Q: Could you walk us through your professional journey and share how you got to where you are today? What were the key turning points in your career?
Rahul: Sure. I grew up in different parts of northern India and graduated in mining engineering in 1999—not data mining, but actual mining. By the time I graduated, I realized I wasn’t interested in a mining career and was more drawn to computers. Luckily, the global IT boom was happening, so I joined an Indian IT services company in Bangalore and spent about seven years there as a Java programmer. Back then, Java was like Go or Rust today—the cool thing to do. I worked across domains, mostly finance.
After that, I moved to Singapore and joined Credit Suisse, an investment bank. That was my first real foray into the data world. Most products and technologies there were data-related—though we didn’t call it “big data” yet. I worked on a team called Market Data Ingest, essentially doing ETL, though we didn’t use that term then either. I spent six or seven years there, starting as a back-end engineer and later becoming a team lead.
Then I joined Thoughtworks, a consulting company known for its deep engineering culture—Martin Fowler is there. I worked across domains again but stayed close to data. About three years ago, I moved to Berlin to join Omio (formerly GoEuro), a ticketing company. If you’re traveling in Europe—and now also in the US—you can book tickets on our portal. I was asked to lead the BI and Data Engineering team, and that’s what I’ve been doing since. It’s funny how I started with mining and now do “data mining,” though today we call it data science.
What is mentoring?
Q: How would you define mentoring, and what role do you think it plays in professional development? What makes mentoring different from other types of professional relationships?
Rahul: Traditionally, mentoring is a partnering relationship with someone who knows more about a topic than you do. You reach out, build a supportive relationship, and get help answering questions. I define it more loosely: it’s reaching out for a different perspective—on a problem, a challenge, or a career decision—and getting input from someone whose viewpoint might help.
In tech, this is especially important. Unlike fields like food, retail, or law, we don’t have a strong apprenticeship tradition—those first years working closely with someone who guides you. So having someone to reach out to becomes crucial.
Q: Does mentoring always need to be a long-term commitment, or can it be more flexible? What are the different types of mentoring relationships?
Rahul: It depends on your needs. I recommend having a long-term mentoring relationship, but people often have small, specific questions too—and that’s totally fine. It can be as simple as: “I’m a Java developer and want to move into data analysis—is this the right move for me?” That’s also mentoring.
Experiencing mentoring
Q: Looking back at your career journey, what role did mentorship play in your professional development? When did you first experience mentoring?
Rahul: For my first ten years, it didn’t play much of a role—and that gap is part of why I got into mentoring. I didn’t even know what mentoring was. That changed when I joined Thoughtworks, which has a rich culture around mentorship—every employee has a sponsor or mentor. That’s when I started having both mentors and mentees.
Q: Could you tell us more about how Thoughtworks structured their mentoring program and what made it effective? What were the key components?
Rahul: You’re encouraged to find a mentor yourself; if you can’t, the people team can help. Typically, your mentor isn’t from your immediate team. The idea is to get impartial guidance, so it’s better if the person isn’t your manager.
Finding a mentor
Q: What advice would you give to someone looking to find a mentor outside of formal mentorship programs? Where should they start?
Rahul: That’s often the hardest part. You want someone with relevant experience who can offer actionable advice—and who can actually play the role of a mentor. It’s iterative: don’t spend ages searching for the “perfect” person; try a few. Ask in your network. If your company has a program, use it. Otherwise, personal networks and platforms like The Mentoring Club make it easier. I’ve also seen people reach out directly on LinkedIn. It may take a few tries before you find the right fit.
Q: Do you have any advice for reaching out to potential mentors you don’t know personally? What makes for an effective cold outreach message?
Rahul: Building a relationship first helps. Participate in communities—meetups, Slack groups like DataTalks.Club—so people see how you contribute. Then reach out. But don’t be afraid of a well-crafted cold message either. Be specific: who you are, what you’re struggling with, what you’ve already tried, and what question you need help with. Share some background. Vague “can you help?” messages are hard to respond to. Specificity and authenticity go a long way—and don’t be discouraged if someone doesn’t reply. Keep trying.
Benefits of being a mentor
Q: From your experience as a mentor, what are the main benefits you’ve gained personally and professionally? How has mentoring impacted your own career development?
Rahul: There are several. First, helping someone and sharing experiences is rewarding—it’s a way to pay it forward. It’s also made me a better listener; mentoring requires careful listening. As a team lead, mentoring gives me perspective on my own leadership—when someone brings me a challenge, I can reflect on whether I’m creating similar issues for my team. Finally, it’s expanded my network; through The Mentoring Club, I’ve connected with many other mentors.
There’s another subtle benefit: pattern recognition. Five people may bring different problems, but you start recognizing common themes underneath—imposter syndrome is a big one. You become sensitized to these broader issues and start noticing them in your own team and environment.
Mentoring beyond your domain
Q: Is it possible to effectively mentor someone outside your area of expertise? Can you share examples of how you’ve navigated situations where you weren’t familiar with the mentee’s domain?
Rahul: Absolutely. People reach out from marketing, construction—fields far from my background. At first it feels like there’s no overlap, but simply offering a listening ear is part of mentorship; sometimes that alone helps them clarify their thinking. Many workplace issues are universal. I might say, “I don’t know your environment exactly, but this sounds similar to something I’ve seen; here’s what I did.” You look for connections you can make.
The Mentoring Club
Q: Could you tell us about The Mentoring Club? What is it, how did it start, and how does the platform work for both mentors and mentees?
Rahul: It started earlier this year in Berlin, founded by a few of my (now ex-)colleagues. The motivation was simple: reach people who need career mentorship or coaching. It’s grown to around 300 mentors and roughly a thousand sessions (if not more). It’s completely free: you book a session with a mentor and then it’s between you and them. Mentors come from product, tech, marketing, sales, design, entrepreneurship—many are CXOs across Europe and beyond.
Q: What are the specific areas or topics you typically help people with in your mentoring sessions? What kinds of challenges do people bring to you most often?
Rahul: Career navigation: workplace challenges, career decisions, switching tracks, whether to pursue higher education. I also cover technical topics from my recent background in data engineering—e.g., data stacks for startups.
Preparing for mentoring sessions
Q: What advice would you give to someone preparing for their first (or next) mentoring session? How can mentees get the most value from their time with a mentor?
Rahul: A common pattern: first, contact the mentor with context—your background and what you’re looking for. Take time to reflect: what do you want from the session—one-off idea-bouncing, validation of a decision, or a longer-term relationship? Don’t over-prepare; it’s not a job interview. Share the basics and let the conversation flow. One common misconception: people expect very specific, definitive answers. Often there isn’t one. A mentor’s job is to offer pointers, probe deeper, and plant seeds—to help you think. It’s a process; understanding that helps set realistic expectations.
Common mentoring challenges
Q: Based on your experience, what are the most common challenges or concerns people bring to mentoring sessions? Are there recurring patterns you’ve noticed?
Rahul: Imposter syndrome—more than half the people who reach out feel “not good enough.” Another big one is tech vs. management. After five or six years, people are nudged toward leadership and worry it’s a binary choice: people management vs. hands-on tech. And of course, career moves: which company, whether to do a degree, and so on.
There’s no single answer to imposter syndrome. Imposter feelings have different root causes. My process is to go deeper: what’s underneath? Often it’s a perception shaped by external factors, sometimes internal ones. We scratch the surface, question beliefs, and try to define the feeling more specifically. “I’m not good enough”—what does that actually mean in your context? The “advice” emerges from understanding the root, not from a template.
Learning people skills for mentoring
Q: Mentoring requires strong interpersonal skills and emotional intelligence. How can technically-focused professionals develop these softer skills to become effective mentors?
Rahul: A natural inclination to help is useful, but most people have it. Work is social—even programming and data work are team sports. You onboard newcomers and help colleagues, so you already practice people skills, even if you don’t label them that way. Then there are learnable “tricks of the trade”: be a better listener, avoid becoming the “advice monster” (as a colleague calls it), don’t jump straight to solutions. It’s a skill that grows with practice. If you look closely, you’re probably already doing parts of it—mentoring just takes it to the next level.
Balancing tech and leadership
Q: Many people worry that as they take on more leadership and mentoring responsibilities, they’ll lose their technical edge. What’s your perspective on this, and how do you personally balance technical work with people leadership?
Rahul: I get this question a lot. It’s rare to remain a pure individual contributor forever. As you gain experience, you naturally help others. The myth is that you must choose: people leadership/mentoring or tech. In reality, these worlds converge. I still write code almost every day while leading a team, doing stakeholder management, and joining architecture deep dives. You can shape your day—decide your own mix of coding versus people work. In most companies (and as a freelancer), that balance is manageable. Don’t surrender control of your time; define it.
The key is accepting that a blended path is viable. Once you commit to that, you can design your schedule. The ratio won’t be identical every day, but over time you can delegate more, create space, and keep coding. The first step is the mindset shift: there’s nothing wrong with wanting both, and you can make it work.
Q&A from the Audience
Mentor motivations
Q: Beyond the obvious benefit of helping others, what drives people to become mentors? What have been your personal motivations for taking on this role?
Rahul: Several things: you become a better listener, you start seeing patterns across different problems, and it’s intrinsically rewarding to help. For me, there’s also a personal reason—for my first ten years, I had no mentor. I came from mining, had no software people in my family, no apprenticeship culture, lots of uncertainty, and years of imposter syndrome. My motivation is to provide the support I didn’t have. Everyone will find their own reason, but those are mine.
Long-term mentoring and finding mentors
Q: What are your thoughts on long-term versus one-off mentoring relationships? And is it better to find a mentor within your organization or look externally?
Rahul: I have a few long-term mentees—from Thoughtworks and the club—but it’s tricky. Time investment matters, and sometimes long-term mentorship becomes a paid relationship. Many mentors do it professionally. One-off sessions are fine; for long-term relationships, align on expectations—sometimes that includes a fee. I recommend longer relationships because you can’t grasp the full context in one call. Getting to know each other over time makes the work more productive.
As for finding mentors within your company—not necessarily. If your organization has a program or people you can approach, that’s great. Otherwise, external mentors can be equally (sometimes more) unbiased and helpful.
Q: There’s often confusion about the distinction between a manager and a mentor. Can your manager effectively serve as your mentor, or should these be separate roles?
Rahul: Managers run 1:1s and handle delivery and career topics, but their role isn’t fully neutral. It’s advisable to also have a mentor who isn’t your manager—they can be more unbiased (they can even say “quit this job,” which a manager likely won’t). Also, don’t limit yourself to one mentor. Build a small “personal board of directors” for different needs (e.g., domain guidance, leadership, identity-related perspective).
Q: Long-term mentoring relationships can be wonderful but also complex. What advice do you have for setting healthy boundaries and expectations on both sides?
Rahul: Start with clear expectations. Paid setups often make boundaries easier—both sides commit and know what to expect. Even in unpaid cases, I’ll say, “Let’s not meet again unless something changes,” because weekly chats without progress have diminishing returns. I’ll ask, “What’s different from last month?” If the answer is “nothing,” we skip that session. Both sides need to be mindful of this.
Paid mentorship
Q: There’s sometimes debate about whether mentorship should be free or paid. What are your thoughts on paid mentorship, and do you think compensation changes the dynamic or effectiveness of the relationship?
Rahul: Absolutely—it can be more constructive and accountable. Like a gym membership: if it works for you and is fairly priced, it increases commitment and goal clarity on both sides. It’s more common for senior leaders (e.g., CXOs). For early-career folks, I see fewer paid, long-term mentorships, though paid interview prep or tech coaching is more common.
If you provide real value, there’s nothing wrong with charging—just like training in data science or engineering. Paid setups often clarify expectations and boundaries. Some people even do this full-time. If mentees benefit and you deliver value, it’s a valid path.
Building meaningful mentoring relationships
Q: Mentoring works best when it’s more than just a Q&A session. How can mentees cultivate a genuine, reciprocal relationship with their mentors rather than treating it as a one-way advice channel?
Rahul: Treat it like any relationship. Invest over time and be authentic. Don’t treat it like a job interview or a highlight reel—share challenges, strengths, and weaknesses. Periodically run a small retrospective: what’s working, what isn’t, what do you need more of (e.g., book suggestions, frameworks, exercises)? Co-create the approach.
Starting as a mentor
Q: Does your mentoring approach differ when working with junior professionals versus senior leaders? Do you need different skills or techniques for each?
Rahul: Not really. The problem spaces differ, but the depth of struggle is similar. The approach—listening, probing, pattern-spotting—remains the same.
Q: For someone who’s interested in becoming a mentor but doesn’t know where to start, what practical first steps would you recommend? How can they begin their mentoring journey?
Rahul: Start by reaching out to your network, but don’t give unsolicited advice. Offer support as an option: “I’m here if you want to talk through something.” If you want a formal path, join a platform like The Mentoring Club (there are others, like Plato). Skill-wise: lead with empathy, listen more than you talk, and remember that people’s contexts differ from yours. Avoid the “advice monster”; ask good questions first. It’s learnable, and you get better with practice.
Personal development and well-being
Q: Many personal development plans are created with good intentions but end up forgotten. What’s your approach to building and actually following through on a development plan with a manager or mentor?
Rahul: It depends on your goals; format matters less than follow-through. Most plans fail because we don’t revisit them. Review the plan together regularly—weekly 1:1s or monthly check-ins. Keep it visible so it doesn’t gather dust. Planning is easy; practice and process are the hard parts.
Q: This is a bit personal, but many people struggle with feeling overwhelmed at work. How do you personally deal with these feelings, and has mentoring changed your perspective on managing stress and overwhelm?
Rahul: I’d love to say “take a break and reprioritize,” but I don’t always do that well myself. Overwhelm is a mental state; go a layer deeper. What’s driving it—fear of a tough meeting? Too much work? Decisions piling up? Name the source, then break it into pieces you can tackle. Mentoring has made me reflect more on how I handle this and become more empathetic when others face it.
Timestamps
Transcript
The transcripts are edited for clarity, sometimes with AI. If you notice any incorrect information, let us know.
Alexey: Thank you everyone for coming to today's event. This event is brought to you by Data Talks Club, which is a community of people interested in data. We have weekly events, and the ones we usually have on Tuesday are more technical and include presentations. This week we talked about AWS Glue DataBrew, a new service from AWS. We will take a break for a couple of weeks and then next month we will talk about model monitoring and a feature store called Feast. (0.0)
Alexey: We also have live podcast events on Friday like today. These are more like discussions, without slides, and they are usually just Q and A. Today the topic is mentoring. For this type of event we will also have a break and come back in the middle of January with a topic on writing. Then we will talk about a developer advocate role and machine learning operations in Europe. (20.0)
Alexey: If during today you have any questions, please ask them on Slido. Slido is a special platform for asking questions. I will now share the link with you in the chat, and you can click on it. (1:12)
Alexey: We can start. Let me pull up my notes. (1:40)
Alexey: Today the topic is mentoring, and we have a special guest, Rahul Jain. Rahul is a technical leader with 20 years of experience in building and running software products. He now leads the business intelligence and data engineering units at Omio, which is a ticket booking company. Rahul is also a mentor at the Mentoring Club, where he offers guidance and coaching to engineers and managers. This is why I reached out to him and asked him to share his experience with us. (2:00)
Alexey: Thank you Rahul for coming today. It is a pleasure to have you. (2:39)
Rahul: Thanks Alexey for having me. (2:45)
Alexey: Before we go into the main topic of mentoring, maybe you could tell us a bit about your background. Can you tell us about your journey so far? (2:51)
Rahul: Sure. I grew up in India in different parts of northern India, and I graduated in 1999 in mining engineering. Not data mining but mining engineering. By the time I graduated I was no longer interested in pursuing a career in mining and became more interested in computers. (2:57)
Rahul: Around that time there was an IT boom, so I took advantage of it and joined an Indian IT services company in Bangalore. I was there for about seven years as a Java programmer. Back then Java was almost like how Golang and Rust are today, the cool thing to do. I learned a lot and worked in different domains as part of a consulting company, mostly in finance but also in other areas. (3:10)
Rahul: After spending seven years there, I moved to Singapore and joined Credit Suisse, an investment bank. That was probably my first experience in the data world because most of the products and technologies there were related to data, even though we did not call it big data at the time. I was part of a team called Market Data Ingest, where I worked on ETLs, although I did not know they were called ETLs back then. (3:49)
Rahul: I spent six or seven years there, first as a back-end engineer and later as a team lead. Then I joined ThoughtWorks, a consulting company with offices around the world. They are very popular for deep engineering skills, and Martin Fowler is one of their employees. There, again, I worked in different domains but stayed close to data. (4:07)
Rahul: About three years ago, I moved to Berlin to join Omio, which was called GoEuro at the time. We are a ticketing company. If you travel anywhere in Europe and now also in the US, you can go to our portal and book your tickets. When I joined, I was asked to lead the BI and data engineering team, and that has been my journey so far. (4:49)
Alexey: It is an interesting experience, especially starting from mining. (5:35)
Rahul: Yes, absolutely. It is kind of funny because I started with mining and now I am doing data mining, even though it is not called data mining anymore. Now it is data science. (5:42)
Alexey: Today the topic is mentoring, and you are active in this area. You mentor people at the Mentoring Club. What does mentoring mean to you? (6:03)
Rahul: The traditional definition of mentoring is about having a partnership with someone who knows a bit more about a topic than you do. You reach out to them and build a supportive relationship, usually to answer questions or get guidance. For me, the definition is broader. It is about reaching out to someone for a different perspective. (6:16)
Rahul: It could be about a problem you are trying to solve, a challenge you are facing, or a decision you are trying to make in your career. It is about getting an opinion from someone who might have an interesting perspective. In our industry it is especially important because we do not have a strong tradition of apprenticeship like in food, retail, or law. (6:42)
Rahul: For the first few years we rarely work closely with someone who mentors us. That is why it is important to have someone to reach out to when navigating challenges. (7:17)
Alexey: So for you, mentoring does not necessarily mean a long-term activity. It can be reaching out for advice, but it can also be something more formal, like an apprenticeship program at a company that lasts for a couple of years. (7:39)
Rahul: It depends on your needs. Traditionally, and something I recommend, it is good to have a long-term mentoring relationship. But people often have small, very specific questions, and it is perfectly fine to reach out and get advice in that area too. The definition is not strict. It can be something short or something long, depending on what you need. (7:55)
Rahul: If I am a Java developer and want to move into data analysis, I can reach out to someone and ask whether this is the right path for me. That can also be mentoring. (8:11)
Alexey: Was mentoring an important part of your career so far? (8:40)
Rahul: For the first ten years, no. That is the crazy thing. That is probably why I eventually got into mentoring, because I realized how big that gap was. For the first ten years I did not have a mentor. I did not even know what mentoring meant. (8:48)
Rahul: My experience with mentoring, both as a mentor and a mentee, started when I joined ThoughtWorks. ThoughtWorks had a strong culture of having a sponsor or mentor for every employee. That is how I was introduced to the concept and how I started having mentors and mentees. (9:02)
Alexey: How does it work? The moment you join, do you get a mentor who stays with you throughout your time at the company? (9:25)
Rahul: They experiment with different formats, but that is typically how it works. You are not always assigned a mentor; you are encouraged to find one yourself. If you cannot, the organization or the people team will help you. (9:31)
Rahul: The mentor is usually not from your team because the idea is to get mentorship from someone who can offer an unbiased opinion about your career. It is advisable to have someone who is not your immediate manager, maybe someone from a different team. (9:45)
Alexey: If you want to find a mentor, it is great when a company has a mentorship program. Having someone to talk to about your problems is very useful, especially because there are things you do not want to discuss with your manager. How can you find such a person? (10:18)
Rahul: This is probably the most difficult part. You want someone who has relevant experience and can offer meaningful advice. You also want someone who can actually play the role of a mentor. Just because someone knows a topic does not mean they are good at mentoring. (10:51)
Rahul: It is an iterative process. Rather than spending too much time up front searching for the perfect person, you may need to try a few people. You can ask around in your network, join a formal mentoring program if your company has one, or use your personal connections. (11:03)
Rahul: There are also programs like the Mentoring Club, which make finding a mentor easier. Some people even reach out directly through LinkedIn to someone they know or have heard of and ask if they have time. But it takes a few iterations to find the right person. (11:54)
Alexey: You mentioned reaching out to your network. I sometimes get messages like “Can you help me with this?” and I often cannot because I do not always have the required expertise. Sometimes it feels like people send the same message to everyone, hoping someone will respond. I think there is a better way to target a message to a specific person. How would you recommend doing this? (12:25)
Rahul: It is similar to building a relationship. Cold messages are unpredictable because the other person does not know you or whether they can help. Investing a bit in the relationship first is better. Join a meetup group, participate in a Slack community, or engage in discussions. The other person gets to know you a bit, and then you can reach out. (13:04)
Rahul: If they have seen how you work or participate, they may be more open to the conversation. But I would also say do not be afraid to reach out if you have a good reason. Sending a thoughtful, specific message can be effective. And do not get discouraged if someone does not reply. (13:29)
Alexey: Speaking of messages, sometimes I get cold emails that are really good. How should such an email look to increase the chances of getting a response? (14:22)
Rahul: Being specific helps. If I get a message that says “Can you help me with something?”, I do not know whether I can help. It is more useful when someone explains who they are, what they are struggling with, and what they have already tried. Showing authenticity and effort makes a big difference. (15:02)
Rahul: Sharing a bit about your background and explaining how you are navigating the challenge can also help. (15:38)
Alexey: This experience as a mentee at ThoughtWorks at some point you also became a mentor yourself, right? First, you were a mentee, someone was helping you, but you spent quite a while there. At some point, you had enough experience to actually mentor somebody. What did this do to your career? Was it helpful at all, and what were the benefits for you as a mentor? (15:57)
Rahul: There are quite a few benefits that I have seen over the last few years. First and foremost, just being able to help someone or share your experiences is a reward in itself because it is a way of giving back. I also felt it made me a better listener because you have to listen a lot. (16:21)
Rahul: As a team lead, I lead a team, so mentoring also gives me perspective on leading a team and what that means. For example, if someone comes with a problem, I can relate that to my own experiences with my team. Finally, it has expanded my network. Being part of the Mentoring Club, I am connecting with other mentors, which is rewarding. (17:05)
Alexey: If somebody reaches out to you on a topic where you do not have experience, what do you usually do in that case? (17:58)
Rahul: It is simple. I just say I do not know and cannot help in that area, and then try to connect them with somebody who might be able to help. (18:04)
Alexey: Have you ever been in a situation where you did not know how to solve a problem but just by listening and asking questions, you were able to help them? (19:00)
Rahul: Yes, I always try to do that. Quite often, someone reaches out from marketing or even construction. Initially, it feels like there is not much overlap, but giving a listening ear itself is part of mentorship. Often, by talking, people can solve their own problems. (19:12)
Rahul: Also, you can recognize common patterns. Even if they come from a different background, many social problems in the workplace are common. You can relate and say, "This is similar to what I have seen, here is what I did," and start connecting dots between different worlds. (19:52)
Alexey: These people from construction or other industries, did they find you through the Mentoring Club? (20:29)
Rahul: Yes. (20:41)
Alexey: Can you tell us a bit more about this club? (20:51)
Rahul: It was started earlier this year by a few colleagues in Berlin. The motivation was simple: to reach out to people who need career mentorship or coaching. It is grown to almost 300 mentors. I do not have exact numbers, but we have given close to a thousand sessions. It is completely free. You just book a session with a mentor. (20:58)
Rahul: Mentors come from all walks of life. There are CXOs, people from product, tech, marketing, sales, design, entrepreneurs, and lots of different backgrounds. (21:41)
Alexey: Which topics do you help with on this platform? (22:07)
Rahul: I help with career navigation, challenges at work, career decisions, switching careers, or deciding on higher education. I also talk about technical topics like data engineering stacks for startups. It varies. (22:15)
Alexey: If someone wants advice and wants to reach out to you through the Mentoring Club, how should they best prepare to get the most out of the session? (22:50)
Rahul: It depends on what you are looking for. If you have specific challenges, reach out to your mentor first and give as much detail as possible about your background and goals. Do a bit of introspection. Are you looking for a one-off session, validation of a decision, or a long-term engagement? (23:04)
Rahul: Do not over-prepare. It is not a job interview. Share the details and let the conversation flow. One misconception is expecting a specific answer. Mentoring is about pointers, planting seeds, probing deeper. It is a process. (24:02)
Alexey: Can you share an example from a recent session? What kind of problems do people approach you with? (25:03)
Rahul: Some common areas. Imposter syndrome affects more than 50 to 60 percent of people who reach out. They feel they are not good enough. I also get questions about tech versus management, especially for people with five or six years in technology now being asked to take leadership roles. Other questions include career moves, whether to join a company or pursue higher education. (25:17)
Alexey: If someone comes to you with imposter syndrome, what do you usually recommend? (26:15)
Rahul: There is no one answer. Imposter syndrome can happen for various reasons. I usually go deeper into the root cause. Often it is a perception built by external or internal factors. The process is to scratch the surface, question beliefs, and help define the problem more specifically. (26:27)
Alexey: It seems to me that to be a good mentor, you really need to understand people and go deep to find the root cause. How do you learn that as a tech person, like a Java developer? (27:30)
Rahul: It helps to have a natural inclination to help people, which most people do. Early in your career, you spend energy as an individual contributor, but even then you help new team members onboard. Tech and data work are social activities, so you inadvertently develop people skills. You just need to hone them for mentoring. (28:02)
Rahul: Some aspects, like being a better listener or avoiding the “advice monster,” jumping immediately into giving advice, are learned over time. Mentoring is a skill that comes with practice, and you are likely already doing some of it at work. (29:15)
Alexey: So basically, do not be afraid of trying. It is not as difficult as it sounds. (29:56)
Rahul: No, not at all. It is very rewarding. It is not about sitting on a higher pedestal. It is about listening and helping others. (30:01)
Alexey: What are the main motivations for a mentor to mentor someone? You mentioned helping personally, seeing patterns, becoming a better listener, and the reward of helping someone. Is there anything else? (30:20)
Rahul: Those are the main ones. It is also about expanding your perspective and network. You learn through mentoring while providing value to others. (30:40)
Rahul: Personally, for me, as I said earlier, for the first ten years I had no one to work with. I did not know what I was doing. I came from a mining background. There were no engineers or people in software in my family that I could talk to, and there was no culture of apprenticeship or mentorship in the first few years of my career. I struggled a lot. I did not know if Java was the best thing for me. I also went through imposter syndrome for many years. (30:46)
Rahul: For my personality, my motivation came from that experience. Since I did not have guidance, I wanted to provide that space for other people. You need to find your own motivation, but these were some things that motivated me. (31:22)
Alexey: Through this mentoring club, some people just want a one-time conversation, but sometimes people need something more long-term. How often do you have somebody who wants long-term mentorship? (31:43)
Rahul: Long-term mentorship is a little tricky. I have a few people I mentor long-term, some from ThoughtWorks and some from the mentoring club. You need to be mindful of the mentor’s time investment. Some mentors do it professionally and charge a fee. (31:58)
Rahul: Other than that, it is about establishing a clear agreement. If the mentor is interested and willing, long-term mentorship is very valuable because it helps understand the entire context over time. (32:50)
Rahul: It makes sense to find someone in your workplace for long-term mentorship if there is a formal program or someone you can reach out to informally. (33:24)
Alexey: How do you set boundaries for long-term mentorship relationships? (33:48)
Rahul: Sometimes a paid relationship helps create boundaries and expectations. In unpaid long-term mentorship, it is about setting clear expectations. For example, tell mentees it is not meaningful to meet unless there is a change in their situation. Avoid diminishing returns. (34:12)
Rahul: Being mindful from both sides helps. Ask if the extra session will be beneficial before committing. (35:32)
Alexey: What do you think about paid mentoring? (35:46)
Rahul: Paid mentoring can be very beneficial. It can be more constructive and allows better expectations. It creates accountability and motivation from both sides. It is common for senior leaders but less so for early-career professionals. For less experienced people, paid mentorship often focuses on job preparation. (35:59)
Alexey: How can a mentee build a two-way connection with a mentor, not just ask questions? (37:38)
Rahul: Treat it like any relationship. Invest time, be authentic, share challenges, strengths, and weaknesses. Conduct retrospectives over time, discuss what is working, ask for resources, and make it work for yourself. (37:50)
Alexey: How can people join the mentoring club? (38:46)
Rahul: As a mentee, go to the website, search for a mentor, and book a session through Calendly. As a mentor, fill out the enrollment form, and Bastian and Jess will review your application. (38:54)
Alexey: Is there a difference mentoring juniors versus more experienced people? (39:47)
Rahul: Not really. It is about the challenges they face and whether you can provide meaningful guidance. The problem space may differ, but the approach is similar. (40:07)
Alexey: Should managers be mentors, or is it better to have a separate mentor? (41:05)
Rahul: Managers often have one-on-ones that are somewhat like mentorship but are delivery-focused. It is better to seek someone who is not your immediate manager for unbiased opinions. You can also have multiple mentors for different areas of your career. A mentor shows direction but does not make decisions for you. (41:23)
Alexey: How should someone start being a mentor? (43:35)
Rahul: Reach out to your network. Offer mentorship as an option but do not give unsolicited advice. You can join formal programs like the Mentoring Club or others like Plato. Prepare yourself with empathy, listening, and understanding context differences. (44:02)
Alexey: Some people use mentoring as a side income. What do you think? (45:18)
Rahul: If you provide value, there is nothing wrong with charging money. It helps set expectations and boundaries. Some people pursue mentoring full-time successfully. (45:32)
Alexey: What about developers who become mentors and code less over time? (47:00)
Rahul: It is common when moving into leadership. Mentoring is part of people management. It is a myth that you must choose between people management and coding. You can balance your time between coding, management, and mentoring according to your priorities. (47:12)
Alexey: Any advice for someone who wants to keep coding while managing teams? (50:12)
Rahul: Accept that you can manage your time and mix coding with management. Delegation helps create time for coding. The first step is accepting that a balance is possible. (50:23)
Alexey: How can one work on a personal development plan with a manager or mentor? (52:12)
Rahul: It depends on your objectives. Look at the plan regularly with your mentor or manager, weekly or monthly. Plans fail when they are created but not revisited. The format does not matter as much as the process. (52:30)
Alexey: What do you do when you feel overwhelmed? (54:18)
Rahul: I take a break, reduce less important tasks, and try to understand what is causing the overwhelm. Break it down into specific causes like workload or fear, then tackle them piece by piece. (54:26)
Alexey: What are some examples of value you gained as a mentor? (55:48)
Rahul: When questions arise again, you are better prepared because you have navigated similar situations before. It increases empathy toward others. (56:00)
Rahul: This year has been difficult. Connecting with people from different parts of the world, hearing their struggles, and being able to help has been personally rewarding. (56:38)
Alexey: Thank you for sharing your experience as a mentor. (57:23)
Rahul: Thank you. I enjoyed it a lot. Thanks for inviting me. (57:30)
Alexey: Please share the blog post link and the Mentoring Club link. (57:41)
Rahul: I am a member of the Slack group. Listeners can reach out anytime. (57:55)
Rahul: Have a nice day and a nice weekend. Bye everyone. (58:06)
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