Secrets of a Stealth Mentee

by Katherine Wu

In her presentation 'Secrets of a Stealth Mentee' at RubyConf 2018, Katherine Wu, a Senior Software Engineer at Heroku, explores the nuances of mentorship in the tech industry. The talk is structured around recognizing common challenges encountered in traditional mentorship programs and presenting actionable strategies for seeking effective guidance.

Key Points:
- The Problem with Mentorship: Katherine reflects on her experiences with formal mentorship programs, noting a lack of impactful outcomes despite good intentions. She highlights a deficit of skilled mentors in the tech field, which can hinder career development.

Importance of Mentorship: Wu emphasizes that mentorship can demystify career paths and provide insights into what opportunities exist, helping individuals navigate their professional journeys more effectively.
Defining Roles: She distinguishes between mentors, who provide perspective and guidance, and sponsors, who offer opportunities. Both are important for career progression but serve different purposes.
Always Be Mentoring: Katherine argues for an ongoing view of mentorship, where relationships can be short-term and focused on specific goals rather than long-lasting commitments.
Proactive Approach: Instead of waiting to be noticed, she encourages individuals to seek out mentors casually and suggests that mentorship can come from various sources, including informal interactions, readings, and online resources.
Networking: Wu reframes networking as simply making connections without expectations. She advocates for engaging with new attendees at conferences and offering sincere feedback as a way of building relationships.
Initiating Conversations: To engage potential mentors, Katherine recommends making it easy for them to connect by scheduling meetings with their availability in mind and suggesting specific topics for discussion.
Asking for Experiences: Rather than directly seeking advice, Wu suggests that mentees ask mentors about their experiences, as this can yield more actionable insights.
Building Trust: Trust is essential in mentorship. Katherine advises following up with mentors to share progress and show appreciation, reinforcing the relationship over time.
Resource Recommendations: At the end of her talk, Katherine provides a list of additional resources, including articles and books that further explore mentorship and personal development.

Conclusion: Wu’s presentation is an empowering call for individuals to take ownership of their mentorship journeys. By applying her strategies, attendees can cultivate better relationships with mentors and leverage these connections to achieve career growth and fulfillment.

00:00:15.619 Thank you all for coming! I have given a decent number of conference talks over the years and right now I'm going through the moment before every single one of them, where I'm like, 'This was a terrible idea, why did I sign up for this?' It's also a reminder that, while it feels intense, I'm not literally going to die; I'm going to survive the next 30 minutes, probably. It's happened in the past.

00:00:23.010 So, hello! I'm Kay Wu, short for Kathryn Wu, but everyone calls me Kay Wu. I am a Senior Software Engineer at Heroku, and I'm here today to share some things I've learned over the years about receiving good mentorship. The slides should be shared from my Twitter account, which you should be able to find on most of the slides I present today.

00:00:40.680 As for the structure of the talk, I will dive quickly into what I think the issue is, or how I’ve experienced it at least—the usual, 'Why do we care about this problem?' Then, the meat of the talk is, of course, in the solutions and tactics I’ve figured out until now. Finally, there’ll be a fairly extensive list of additional recommended references and resources.

00:01:03.899 In terms of the problem, let’s talk a bit about a typical mentoring interaction that I've often experienced. Often, there is some sort of program where I got matched up with someone, maybe a little randomly. There were definitely good intentions on both sides, but we’re still not quite sure what to talk about. Maybe we go out for lunch a few times. In one case, when I was in college, I had a mentor assigned for all four years. However, at the end, I often felt like nothing was really different—nothing really changed as a result of that relationship. That’s kind of weird, right? It seems that this relationship, which is supposed to be quite important for one’s career development, didn't quite deliver.

00:01:43.640 I have a theory that especially in the tech world, there aren’t many of us who have both the experience and the aptitude for becoming really good mentors. The field overall is quite young, but the potential is definitely there. So, what might this look like instead? Once I felt like I got better at figuring this out, all sorts of things opened up for me. One big deal was getting encouragement from my mentors to consider applying for job opportunities that I didn’t think I was qualified for. I changed careers; I got into software engineering, and I started giving conference talks. Recently, when I joined Heroku, I called up my friend Jounin, who had given a talk about his waffle-making machine earlier. On the phone, unprompted, he made me practice salary negotiation with him for 30 minutes and made me promise I would give it a shot. So, thank you, Jounin; our bank account really appreciates that!

00:02:59.550 I feel like overall my strategies are not necessarily groundbreaking, but they weren’t obvious to me at first. Hopefully, there might be some ideas that are new for you as well. Overall, what I really want to do is level the playing field a bit and have everyone walk away empowered to get better mentoring for themselves and those that they work with.

00:03:59.390 I want to clarify a distinction between mentors and sponsors; both are very important. In this talk, I will be mostly focusing on mentors. The distinction is something that my friend Kate introduced me to in a blog post where she wrote about how mentors give her perspective, but sponsors give her opportunities. You definitely need both at various points throughout your career. Sometimes you will see both roles in the same person, and sometimes they will be different. You could think of the difference like this: a sponsor might think of you when a really cool job or project opportunity arises and say, 'This person would be really great at that' and nominate you, while a mentor might be someone you go to for feedback on how you can improve your approach to searching for a job overall.

00:05:46.370 I just want to clarify these two distinctions because I think they get muddled sometimes, and it can get confusing based on what you are trying to achieve. There are broader caveats; I am here to share what I think has worked for me, but I want to be self-aware that I might be a bit more comfortable than average when it comes to asking for help. I've heard of the 'ask versus guest' culture spectrum, and I am pretty far on the 'ask' side of things. Coming from the East Coast, that probably makes a big difference. I tend to operate under the philosophy that it’s almost always okay to ask for something. Hopefully, people are totally allowed to say no.

00:07:50.240 That said, I recognize that lots of people grow up in cultures where that is not what's done, and there's importance placed on not imposing on others. If this causes discomfort, I have a separate talk that goes into this topic more in-depth. In case some of the tactics I share might feel more uncomfortable than you are used to, I hope to still be polite and respectful. You can definitely adapt these ideas to your own interests and strengths and figure out how they might work for your comfort level. Hopefully, there’ll be time for questions at the end, but you can always find me at the conference to chat and brainstorm.

00:09:30.430 Now let’s discuss why this problem of mentorship matters. If I can be so bold as to disagree with part of Matz's keynote this morning, I would argue that some of us do want to take over the world someday. I wouldn’t want to rule that out necessarily! The characters on the left here are from an old cartoon show called 'Pinky and the Brain.' If you're familiar with this pop culture reference, my brain is making random connections as I'm pulling these slides together.

00:10:22.490 Frankly speaking, I’ve always had the sense that it's important to have mentors throughout your career. However, for a long time, it seemed like something that other people made happen; it felt quite mysterious. For example, one of my college roommates was amazing at applying for grants—she got a Fulbright and had incredible recommendation letters from her professors. Eventually, I learned that she would regularly go to professors' office hours, which had never occurred to me as a strategy. There are plenty of opportunities like this that, when reflected upon, can uncover lots of untapped potential around you.

00:12:27.080 Mentorship can demystify the world around you. If you've ever felt like you missed something that everyone else seems to know, mentoring can help you address that. I was once matched up with a CTO and decided to ask him why even a CTO exists, which I never covered in any textbook. The more I thought about it, the more I realized that no one is born knowing this stuff. People who do know it don't have any ownership claim, so it's okay to ask questions. By doing so, you'll learn more than you did previously.

00:14:21.690 Another benefit of mentorship is seeing what your options are. When you know what your options are, you can figure out what experiments to run or which paths to steer towards or away from—be it a project you want to work on or potential lifestyles and work setups. And please don’t tell my kid this, but learning the easy way is awesome! If you can learn it the easy way rather than the hard way, you should definitely go for that.

00:16:14.740 The reason I included a picture of Ali Wong's 'Baby Cobra' comedy special is because there’s a bit where she mentions, 'I don’t want to lean in—I want to lie down instead.' Honestly, if you take away nothing from my talk today, I urge you to watch her special; it's brilliant. Although it may not be suitable for work, it's something you should definitely watch in your spare time.

00:17:06.760 Now, let’s get into the meat of the talk. I have categorized my strategies into three sections. First, adapting a phrase from the movie 'Glengarry Glen Ross,' which I haven’t actually watched but hear referenced a lot—'Always Be Mentoring.' I’ll elaborate on what that means shortly. Second, find your kindred spirits, referencing 'Anne of Green Gables,' a beautiful childhood book that emphasizes making connections and finding good friends. Finally, borrowing from a slogan I saw in the nineties, 'Keep it Easy, Breezy, Beautiful'— this phrase is hard to say without thinking of CoverGirl, but apparently they don’t use it anymore, so I’ll use it here.

00:18:52.150 First, 'Always Be Mentioning' mentorship means that I believe the process should be viewed as ongoing. I often built it up in my head, thinking it had to be super meaningful and deep, which isn’t always the case. It’s totally okay to have short-term goals and relationships for more specific topics like giving your first conference talk. This can be the focus of a mentorship, and once you achieve that, you may find it naturally concludes.

00:20:11.050 Edmond Lau has an article linked in the references that talks about 'designing a relationship.' He discusses running effective one-on-ones with your manager, but I think the idea can be applied more broadly. When pursuing mentorship, consider what both parties are aiming to gain from it and what their expectations are.

00:21:54.280 Now, who might you receive mentoring from? A common approach involves mentoring programs where you are assigned a mentor. I have had both helpful and less helpful experiences with this setup. The key might be how you approach people you admire. While it’s often tempting to directly ask someone, 'Will you be my mentor?' I believe that the direct approach can lack effectiveness. However, you don’t have to wait around to be noticed. The notion of waiting for someone to pick you feels akin to standing by the wall at a middle school dance, hoping to be asked to dance.

00:23:48.820 This ties back to some of my feelings about Sheryl Sandberg's 'Lean In' book, which seems to place the onus on individuals to progress their careers. I acknowledge the ideas presented in the book, but I disagree with the concept that you should just do good work and wait to be noticed. Instead, it’s about being proactive and not just sitting back and waiting.

00:24:47.600 So how do you reconcile these ideas? One approach is to skip the formalities altogether. People do not have to agree to be your mentor to mentor you. You can learn from others without them even being aware of it. Mentorship can come from various forms—books, articles, videos, and more. For instance, I have had mentors where I would continually ask them questions, and they kept answering. Often, I later told them that I considered them a mentor, and they might not have had any choice in the matter!

00:26:43.080 What does a good mentor look like? Generally, I look for someone whose values resonate with mine—a direct communicator. I admire those who have done a good job of balancing their judgment and kindness. I learn a lot from them. However, it's not just about having commonalities; it's essential that a mentor has a variety of life experiences. The best mentors surprise me with their perspectives, indicating I will learn something new from them.

00:28:30.020 I consider my mentors to include individuals with expertise both technically and in the workplace. I’ve had mentors on public speaking, career transitions, and even parenting. I turn to those I deem successful in areas I want to grow in; I gain insights from them while ensuring I do not idolize them. It’s important to build a relationship based on trust and safety, so you feel comfortable sharing insecurities or uncertainties.

00:29:54.880 Now, let’s move on to networking. Networking is a topic I often hear about but didn’t fully understand until I reframed it as getting to know people and making friends—without expectations. I recently returned to Ruby conferences after a break and enjoyed reconnecting with familiar faces. Setting the groundwork for relationships is valuable and can be as simple as attending conferences or engaging in conversations with new acquaintances.

00:31:49.460 There are numerous ways to go about networking. Since there are many attendees at the conference, it is an excellent opportunity to meet newcomers. A vital part of networking involves giving positive feedback for engaging work. Everyone wants to hear feedback on their efforts, so acknowledging their contributions can foster goodwill. Additionally, make sure to express how their work impacted you and consider sharing it with others.

00:33:22.020 Moreover, take people up on their offers to help. If office hours are available, utilize them! Opportunities are out there, and you deserve to make use of them. I encourage you to embrace the awkwardness of initiating connections. Many people share similar feelings, making it easier to connect over shared vulnerabilities. If you forget someone's name, don't hesitate to apologize and reconnect.

00:34:24.240 Now that you have found potential mentors, what comes next? Perhaps you want to reach out for a quick conversation or to grab coffee. Make it easy for them to say yes! Schedule with their time in mind, offer a convenient location, or if you’re not not in the same spot, suggest a commonly used platform. Conversation is typically easier than a lengthy email chain, as it allows for smoother dialogue.

00:36:02.390 When initiating conversations, give a general sense of topics you’d like to discuss to help them prepare rather than just obfuscating the conversation. Consider keeping your request casual and light. A suggestion from my friend Kara is to ask people to be 'unofficial mentors,' easing the weight of responsibility on them. By being specific about why you're reaching out and expressing your respect for their work, you're more likely to establish a connection tailored to them.

00:37:30.240 It’s common to feel uncertain about what to talk about at first, and that's okay! One effective tactic is to ask for experiences rather than advice. People might lack the introspection needed to identify what helped them most in their own careers. By interviewing them on their experiences, you can gather data, analyze it for patterns, and apply that learnings to your own path.

00:39:42.880 I have a list of specific topics you can explore with your mentor. Engage with them on problem-solving: present any current dilemmas you're facing and solicit feedback. Additionally, understanding decision-making can provide invaluable insights. Whenever decisions arise, clarify the thought processes and factors contributing to those choices. You might also consider asking, 'What could have changed your mind?' to broaden your understanding of potential scenarios in your own future.

00:41:04.210 Finally, the trust and vulnerability in these relationships allow for deeper conversations about personal feedback. After you have spent time developing this rapport, it becomes easier to solicit insight about areas for improvement or focus. Trust that your mentors want you to progress and will be thoughtful about your requests.

00:42:49.220 I also want to emphasize that you don't have to take all the advice you're given. It isn't an all-or-nothing situation. It's essential to evaluate recommendations and determine their alignment with your journey. That way, if you find that all the advice seems mismatched, it might indicate that this isn't quite a mentoring relationship.

00:43:48.400 In summary, you can stand out as a mentee and become someone others feel rewarded to help. Sometimes it's dysregulated—when I go for coffee, I prefer to buy my own drink as I don’t want to impose on someone who may need to watch their finances. But once you build relationships, small gestures, like thank-you notes referencing your discussions, can be delightful and impactful. It demonstrates gratitude and reflection on the conversation.

00:45:35.980 Specifically, from the perspective of building relationships with trust, it's crucial to follow up and check in with mentors. Convey how you've utilized their advice, and be proactive in rekindling the connection occasionally. I maintain a monthly reminder to reach out, which fosters long-term relationships. Generally, people love hearing from you even without asking for something—it's a positive gesture!

00:47:22.620 Building relationships built on trust is essential in obtaining honest advice and guidance—this support can make the journey of mentorship incredibly rewarding. Additionally, the significance of mentoring others cannot be overstated; teaching others reinforces your own knowledge. Thoughtbot has even published a guidebook on mentorship, available for further reading, to enhance those practices and connections.

00:48:53.920 Finally, here are some resources: a collection of articles, references, videos, and podcasts that delve deeper into many of the ideas I've shared. Books like 'Deep Work' and 'The Effective Engineer' are especially worth your time. I appreciate your attention, and I'm hopeful that you will apply these ideas as you navigate your professional journey.

00:49:38.960 Thank you!