If there’s one thing I have learned in the few years of mentoring others, it is to not give out advice in a prescriptive manner. It is to start by listening more closely and pay attention what the individual needs.
People oftentimes just need a trustworthy person to lend an ear. In those occasions, the best you can do is to serve as a sounding board as they talk through their problem and untangle it; unless the person explicitly ask for your response, it’s better to reserve your opinion. Pay attention, nod along, and you are already doing a great job.
But people do need guidance in some other times, and hopefully, the mentor possesses the wisdom to differentiate the two.
(The question is: should a person be mentoring others to begin if he or she can’t even perceive that?)
In a way, it is a lot like teaching: you have the great power to enlighten or misguide a person. That’s a huge responsibility. Doing it poorly may lead to a more harmful outcome than not doing anything at all.
Just as there are good teachers and bad ones, I’m sure you can think of at least one case of a smart and knowledgeable individual who’s just terrible at empathizing and listening to others. Having lived a long life or being experienced in a particular field doesn’t automatically make someone a good mentor, but it’s commonly mistaken as such.
My Two Mentors
I attribute the majority of my growth today to the two people I met in college. Rather than going through a laundry list of what they did right or wrong, let me describe how our interactions throughout those years have shaped my thinking and influenced my career.
The first person, Smith, taught me a lot of harsh but valuable lessons — in an unexpected kind of way that many of the “nicer” teachers never did.
In a rough chronological order, he was the first person who:
Introduced me to the field of User Experience
Gave me a paying job related to my field
Invited me to dine at his house (which professors rarely do)
Openly criticized me for taking shortcuts on a class project
Fired me for under-performing at the same job that he had given me
Reprimanded me for being naive and not seeing political undercurrents
Every student in the program knew that he has an unusual personality. He never hesitated to lash out criticisms, but neither did he withhold praises.
I took three courses with him in college, although I wasn’t sure if he had really taught me anything. We’d be given assigned readings, but there were never any lectures on them. Rather, he would use the class time to ask big idea questions that often ended in awkward silences. None of his syllabus had any information about what would be covered in a particular week; there was only description of projects and their respective deadlines.
He takes a similar approach to manage his lab staff, except there’s no onboarding process of any sort; the information on the website was at least five or six years old.
His reputation was appropriately reflected as such: people either thought he was just lazy and was so full of it, and avoided every him in every turn of the corner, or they liked him because because he granted them the freedom in-class or at work. Personally? I fluctuated between the two camps throughout those years and landed somewhere closer to the latter.
All of this should give you a pretty good sense of what Smith was like as a teacher and a boss.
(He later revealed to me that he chose to not feed information to students,because he wanted us to learn how to teach ourselves new things. While this is perhaps the only indispensable skill in today’s fast-moving tech industry, I still can’t tell whether or not his sentiment was a 100% truthful. This whole “free-range” style of education caused a lot anguish, as many of the students including myself came with little understanding of technology in the first place.
But the outcome was evident: those of us who persisted through the program did become quite good at self-learning, and I know we are better off for having done so. It’s therefore ironic to hear that people ask “why do we even need Smith when we could just teach ourselves” in retrospect, because working with him was the only reason that we grew comfortable in exploring unfamiliar subjects.)
Ultimately, I can say that meeting Smith early in my career is a fortune in disguise.
He taught me the important lesson that having good result to show is the only thing that matters in the professional world. Employers and clients won’t care about my disadvantaged backstory when they’re deciding whether to hire me; those stories are only good for your college essay, blog posts, and drunken rant with a friend.
When your work is shown side-by-side next to other people’s work, that comparison is the only thing that the decision makers can see and care about. No matter the differences in upbringing or resources available, the ability to work hard is the only equalizer within one’s control. I’m the only one who could make things less unfair for myself.
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My second mentor, Eva, lacks all the quirks that makes Smith a unique personality to learn from, but she offers the exact kind of leadership that every beginner would be grateful for.
I encountered her just a few weeks after I was booted off Smith’s lab and I was desperately looking to make ends meet (since having a scholarship was the only reason I could afford the tuition in the first place). The job she offered me took care of that and a few other things.
Her team consisted of students from various backgrounds and grade levels, but unlike the no-structure lab I was just in, we were given clear instructions on what needed to be done. It was only then that I realized this: for a total novice like me, having a supportive group of peers and an empathic mentor is a difference between night and day.
(Let me paint you a picture how much the two differed:
When I joined Smith’s lab, nobody told me anything about what people were working on or what I could possibly contribute to. I was expected to figure things out on my own, and then to identify and work on new opportunities that could benefit the lab.
But when I joined Eva’s team, I was told exactly what projects people were involved in and how I could be of help to each and every one of them, then I was immediately given a small task of reviewing and editing a video clip to start out with.
This is not meant to be a criticism towards Smith’s mentorship style. While Eva’s style is better suited for the majority of people, it’d also handicap the rare misfits who would otherwise thrive in an environment of minimal supervision and boundary. I think of it as not so much as which one is better than it is a matter of preference and fit.)
I remained in Eva’s care for the rest of my time in college. I learned a lot and made good friends, but retrospectively, I grew complacent of a comfortable wage and didn’t bother to take more risk — in spite of all the benefits, I can’t help but to feel somewhat regretful that I turned a blind eye on other opportunities that would’ve challenged me more.
The biggest thing that these two experiences taught me was the importance of timing — had my encounters with them reversed, I would be much better off in the long run. I would’ve had develop the necessarily skills in the first place before I was put in a position to have to be self-sufficient.
But such is life.
The Elements of Mentorship
As my stories would tell, a good mentor isn’t someone who necessarily has the closest alignment with your interests. Unlike Smith’s technical background, Eva’s expertise is in business and marketing. On paper, it would seem obvious that I’d be better off working under Smith’s guidance, but that wasn’t the case in practice.
My misgiving towards my first job wasn’t just bad timing — it was also a matter of mismatch. I thought I was looking for technical guidance, so I went to a place that offered that. But as it turned out, I needed someone to teach me the ropes of how to do work with the skills I acquired in classes, as well as an environment for me to fail with minimal repercussion.
(It seems so obvious right now in hindsight, but I doubt anyone could’ve convinced me back then; I was determined to hone my technical skills above anything else. It was only after getting myself burnt that I realized that I misjudged my priorities.)
It has been a decade since then and I have sat on the both ends of the mentorship table several times. And after fumbling it here and there, it struck me how many people are generally clueless about all of this. My theory is that giving advice and asking for guidance is a set of skills that a lot of people just have never developed.
Which brings us to my main point: good mentorship is a matter of good timing and match, an ability for both sides to commit, and one has to be an earnest student while the other has to be a capable teacher. All of those factors have to align at the same time, or else the relationship isn’t going to work out.
Let me elaborate:
Timing. As with many significant events in life that take place too early or late, they will amount to nothing if the timing is wrong. So, what good does an advice do when the mistake has already been made? My stories are a perfect example of this. But the poor timing did more than just nothing — it dampened my motivation and almost set me behind. If the timing doesn’t work, then nothing else matters. (I suspect that late bloomers are especially vulnerable to this.)
Match. This has multiple facets, whether it’s personality, mentorship style, type of help needed, so on and so forth. Earlier, I talked about how people may misconstrue a need of emotional support from a need of guidance. This happens more frequently than it sounds, especially because many people’s default mode of operation is to intervene rather than observe; we are too eager to offer a solution to the problem. A good match is also a malleable concept: for the same person who tends to ask for authoritative advice, a supportive style may be better fitting in certain occasions than others.
Ability and willingness. The conditions to achieve a good match often depends on how skilled the mentor is in perceiving nuances and guiding conversations, as well as how open the mentee is to receiving advice and criticism. While it bears no explanation that the former should be skilled in providing guidance, you’d be surprised how often the help seeker isn’t willing to hear anything that already fits their world view. That said, no matter how good the mentor is, there’s no point if he or she isn’t available to you.
Commitment. A relationship can only work if both sides have agreed to fulfill their commitment. A mentorship could be a one-time thing, or it could be a series of conversations surrounding a larger topic, or it could be occasional meetings that take place over many months or years to come. The long term ones serendipitiously occur and could result into a lifelong friendship, but it only happens when it happens.
A Two-Way Initiative
How do you find a mentor, then? How do you approach someone who could potentially mentor you?
Quality mentorship is a time-consuming endeavor. It’s a huge favor that might not result into any tangible return of investment for the person providing it (aside from maybe achieving a sense of satisfaction and making a new friend).
And experienced people are well aware of this: it’s up to the mentee to take the initiative, so as to prove that the mentorship is worthwhile of their effort. Far too often, people who ask for help aren’t good at making it easy for the other side to just say “yes” — if what you’re asking is unclear or you’re asking for too much, how likely do you expect the other side take up the offer?
If you’re thinking about asking for guidance, particularly from someone you’re not too familiar with, here are some important tips to keep in mind.
Be specific and concise upfront, save the minutiae and contemplation for later. If it’s not someone you’ve interacted with before, explain how you’ve found the person and what mutual connection the two of you may have; people are much less likely to respond to strangers if you don’t seem to have a valid cause or connection. If you’ve already been acquainted, jog their memory first as a reminder of how you have gotten to know each other. Clearly state the reason you’ve reached out, the topics you’re seeking advice on, and a few specific options on when and how the conversations can take place (this is really important: you want to make it easy for them to commit). See my networking post for examples on this.
Have the logistics taken care of. Once the other party has agreed to meet, it’s your job to make sure to have everything arranged and work out the details that lead up to the event, whether it’s reserving a table, sending out a calendar invite, or checking the accommodations of the venue. If it’s an in-person meeting, ask if he or she would like you to send a reminder the day before. Also, be prepared for the unexpected and have backup plans in case if the original arrangement can’t pan out for some reason.
Come more than prepared. If you’re asking for career advice, do some research beforehand, and be informed about the person’s background and recent work; you don’t want to appear clueless and waste time asking about readily available information that you could just find in a few clicks. And as I wrote earlier, be mentally prepared to hear things that you might disagree with or that might bruise your ego, because you aren’t ready to talk yet if you aren’t ready for honesty.
Show your interest, be genuine, and show gratitude. Every good relationship requires a foundation to be built, and that’s only possible if both sides become invested to keep the it going. If the interactions revolve too much around the premise of “what can I get from you”, the other side is going to sense that, which is going to kill off their interest quite quickly. A few words of admiration and showing curiosity in their story will go a surprisingly long way. If you can, also offer to return the favor in some form.
Last but not least, follow through and follow up. There are not many things that leave a worse initial impression than disappearing to nowhere after the other side has agreed to meet — it’s going reflect poorly on you no matter what. (It goes without saying to never to do this, yet I’m surprised whenever this happens, but it does.) Send a thank you note via email or leave a message after a meeting, and if appropriate, summarize your takeaways and what you plan to do. If something great comes of their advice, I’m sure the person will appreciate hearing about the news. You can this use as an opportunity to rekindle the connection, which will help maintain the relationship for the long run.
(I have talked some of these in my networking post. In particular, see the different examples on how to start a conversation. Again, I cannot stress enough about taking an initiative. None of the advice matters if you don’t take the initiative to reach out and stay on top of things.
One pitfall to be aware of is when someone publicly advertises to have “successfully” mentored many and have plenty of review videos and articles vouching for the person. They would start by selling you the idea of prosperity and then — here’s the part to watch out for — mention how they’d like help you achieve the same kind of “success”.
That’s a scam, not mentorship. And some of them have mastered the skill of faking their way to the top.
Much like instant noodles, a generic advice that you can get to get at anytime won’t likely help. Good mentorship is tailored to each person’s circumstances; it cannot be mass produced and cleanly packaged like junk foods can be. You will be better off buying a motivational book for a tiny fraction of the price tag.)
What about the other side of the equation? What should you look for in mentors?
Personally, these are the four behaviors that I have identified on people who I consider to be objectively good mentors:
They can empathize with the circumstances of their mentee, regardless of their own station
They are apologetic when they misjudge or when their advice backfires
They are generous with their time and don’t expect reciprocation
They nudge their mentee to pursue better opportunities
While not always true, if someone displays all of these attributes, then he or she can at least be considered as a positive influence. And it goes without saying that, if you have been or will be serving as a mentor, I’d encourage you to pay attention to actively improve upon these areas.