How to incentivize your mentor to keep mentoring you
Those who know me know that I do a lot of mentoring of other designers. As I always say, I have no idea why I do this, but I do know that I feel mostly mixed feelings about it — some of this is necessarily because I have not always liked the way the relationships unfold. As a result, I’m changing my level of commitment to it (i.e., ratcheting down my efforts significantly).
I have been debating about whether or not I wanted to write this opinion piece, as I have a real policy against telling people what to think, how to talk, and what to say. But I wondered if there wouldn’t be mentees out there who could benefit from hearing the mentor’s perspective.
That said, every individual is different — what one person finds impolite, another person will find plucky and likable. Therefore, a mentor’s decision to pull back from mentoring may not even be a response to anything you’ve done (or not done). There is no way to control the behavior of others, so one can only try one’s best to do right by others.
Putting the throat-clearing to one side, I do think there could be an argument made for (maybe) a general set of guidelines for doing right by your mentor, which is why I write this. But I think this depends on the kind of mentor you have.
Moving right along
Every mentor is a unique individual, but I think there are mentors that have different motivations for mentoring. It’s hard to say what all of them could be, but I think there could be said to be three kinds of mentors:
A mentor that is motivated primarily by some obligation to help. It’s possible they recall how hard they had it, and they feel sorry at the thought that anyone could be experiencing the same level of negative emotion they experienced. Mentors mostly motivated by this might be more likely to have longterm relationships with you, where they invest in you at not small costs to their own time. For example, you have an interview in a few days, and so this is the person who might first come to your mind when you urgently need to practice whiteboarding — you know they will actually be amenable to spending several hours with you over the next few days doing this, and also at no cost. Sessions with these mentors tend to be longer. You are likely the only one getting anything out of these sessions — your mentor isn’t getting much in return.
A mentor looking to grow their career. Some call this “thought leadership.” They might do this because they feel that mentoring creates renown in the eyes of recruiters, hiring managers, other designers, and others in the tech industry, which can make one feel authoritative and respected, and that can feel good. They might be looking to generate thought leadership as a way to create social proof, such that they would increase their probability of generating leads in future job searches. Mentors mostly motivated by this might be more likely to give more general advice, and they might not be likely to want to plan for ongoing meetings with you. They are probably not the kind of person you feel comfortable reaching out to if you urgently have a whiteboarding session coming up and are scared about. Sessions with these mentors tend to be shorter. Your mentor is probably getting more out of these sessions than you are.
A mentor looking to start a mentoring business. They either are trying to build experience, renown, and clientele to start charging later, or are currently charging for their time now. Depending on how they choose to run their business, they may behave more like the first example, or more like the second. Ideally, both parties benefit equally in this arrangement.
I don’t think responding to any of these incentives is inherently good or bad, and most people probably are responding to a range of them at any time (even ones not listed here). That said, for the purposes of this article, I’d like to focus on how to be a good mentee to mentors in the first camp (so the ones mostly motivated by a sense of duty).
Here’s the part you could actually start reading at
Mentors who just want to help (and aren’t charging for their efforts) are doing it for free — but only sort of. As we all know, no human relationship is unconditional. But we do tend to have certain (usually unspoken) expectations that we probably believe most humans generally understand.
Naturally, all humans are different, and so expectations about behaviors in relationships do have natural variations — this is normal. Nonetheless, these (unsaid) differences can crop up, and sometimes miscommunications happen along these jagged edges. But this is just the name of the game in human relationships — people don’t generally need to be explicit about their expectations, otherwise we’d be here all day. Generally, people deal with miscommunications as they come up, and hope that every individual is mostly on the same page about most things to start.
Right, so here are some things I think these mentors might generally expect of you.
If you can, be friendly and grateful
Probably obvious, but I’ll be explicit: if you can, please be nice, and express gratitude! I think any mentor — the first kind that I’m focusing on, but also every kind — would appreciate this.
More specific to the first kind: they aren’t asking for money in return, but they are likely expecting “payment” in terms of a positive encounter, where you make it worth their while. I would recommend engaging in behaviors that most humans agree demonstrate gratitude and interest (e.g., look like one is listening, seem excited, offer bodily or verbal feedback of acknowledgement after they share a thought, demonstrate reciprocative behaviors like responses to things they say, etc.).
If they have volunteered to have a longterm relationship with you (meeting weekly, helping you build software, etc.), it is generally understood (I think) that the polite thing to do is to also express interest in their lives as the relationship evolves, strike up conversation, etc. Ideally, you sincerely like the mentor as an individual and, therefore, you naturally feel inclined to ask about their lives and express interest in them, as a human being, and your conversations feel friendly and natural without effort.
Truthfully, when mentees are ungrateful, it can leave one feeling like a human slot machine. Every mentor is different but, personally, these are the relationships I do not maintain. That said, if you can’t find a way to be thankful for what they’re doing, or you don’t think they deserve it (hey, we all value different things!), I would recommend getting off the call and exiting the relationship.
If you can, please don’t be argumentative
On the real here, we totally get it: honest assessments about the quality of your work can be painful. There’s not any one of us who hasn’t experienced this, so we really do feel you.
But, if you can, consider it from our side: your mentor just did something that probably feels very uncomfortable for them — they were (1) honest with someone that is mostly a stranger to them, and (2) honest about something that is obviously likely to stir strong feelings within you. This is probably an awkward thing to do for most human beings. So you’re definitely not the only one feeling uncomfortable and somewhat tense here — it’s weird for both of us.
But, with a mentality of gratitude, one might be able to see the that there is a silver lining here: for one thing, the fact that your mentor can see what’s wrong with your work means they are likely skilled (or, at the very least, more skilled than you are), which means you found the right person to help you increase your quality of life. And they’re doing it for free. It also means you found someone who is truly in your corner — someone who has your best interests in mind. You are very lucky to have them.
It might feel like the right thing to do is to argue with them about their standards (e.g., convince them that their standards are too high, or that they just “don’t know what you’re going for,” and other such things), and succumb to that anger you’re feeling. It might feel like the right thing to do is to think of them as a “gatekeeper,” or that they are “privileged” and just don’t understand you, or something similar to this. There are multiple problems with these narratives, like:
We are actively comparing your behavior to the other mentees we’ve said these exact same things to — and we are noting that you are not emotionally disciplined enough to handle it the way they did. You, like them, have a choice to give in to your anger response. They simply chose not to. Depending on your choice here, we might lose respect for (and interest in) you.
Giving you the information you need to enter the industry reliably is, definitionally, the opposite of gatekeeping, so this doesn’t logically hold up.
They also struggle(d) to get jobs, just as you do — definitionally, you guys are experiencing/have experienced the same job searching pain. Except they did it without someone holding their hand and giving them the secret sauce to get jobs more reliably. They did it alone. You are, by definition, being given opportunities they didn’t have. This is the fundamental reason why they are doing this level of mentoring: because they remember what they went through, feel sorry, and want to help.
There is a chance the mentors’ assessment of your work is wrong, but the probability of that is somewhat low. They see things that you don’t see. To give you a sense of what I mean, here are two analogues: have you ever heard a tone deaf person sing? In their mind, they are singing the tune correctly. But people who are not tone deaf hear something that the tone deaf individual can’t — that they are completely and utterly off-key. Another example: if you’ve ever tried to learn to draw, you might look back months before at drawings you previously thought were beautiful, only to see them for what they really are: totally awful. The probability that this is that time is very, very high.
If a mentor mentions that your visual design needs work, it’s probably not worth retorting with: “I’ve been told my visual design is good, though,” or “my design program says UX designers don’t do UI design.” This is one of those times where you have to understand that you got lucky, because you found a mentor with good enough visual design to see the problems in yours.
What’s more, there is no such thing as picking between these two. Your job is to make software that makes sense, but also software that looks professional. Your design program doesn’t understand this because they are operating on a very dated understanding of the market. The people with the reliable information are not professors who haven’t (ever) practiced. If you don’t want to listen to people who were just fighting for jobs you want on the market six months ago, but rather want to hear from people who theorize about those jobs for a living, then it sounds like you shouldn’t be on this call.
If a mentor tells you that your case studies are not realistic, — as in, the software you’re proposing isn’t solving a real problem on the market — it’s probably not worth returning with a response like: “I got a few interview leads, though, so I think it’s working,” or “that’s not what my design program advised.”
There are low quality workplaces that are willing to take on low quality candidates, as they know they can’t attract skilled talent, and that they can’t afford it. The higher quality customers (the ones we all want to work with) won’t accept your work, won’t reach out, and won’t get back to you. Your mentor wants to help you reliably and repeatably get leads — if you can optimize your portfolio for the highest quality customers, you can get the lowest quality ones. The reverse is not true, however.
We do not want you fighting for scraps that a few low quality customers throw your way, competing among other low quality candidates. If you don’t want our help, please do not ask for it. If you want to do what your design program advises, then it sounds like you don’t need the help of a mentor, which is fine, but it’s best to end the relationship, if so.
This section is, therefore, similar to a previous suggestion above, which would be to practice gratitude, and remember that you do have reasons to be grateful for them.
That being said, your mentor should always be professional and clearly deliver the feedback in ways that indicate they respect you as a human being. If they are not doing that, if they’re rude and disrespectful, make fun of you, or otherwise engage in any other belligerent behavior, you should exit that relationship. This kind of non-normative behavior is not the kind I’m assuming is true of your mentor for the purposes of this opinion.
If you can, just be direct when you need something
If you need something, please just say it! I think this one is probably one where people might be more split on but, personally, I would prefer a message like:
Hey! I recently saw the article you posted, and it strongly resonated with me. I could totally related to what you had to say. I feel like your perspective is refreshing and unusual. Do you think we could have a video call sometime and chat about what I can do, in your view, to improve and get better leads on the market? I’m a bootcamp grad and am feeling lost.
Or, from a mentee that I’m already working with:
omg hey girl so like i was working on adding that new part of the flow we talked about last week…...but idk if i did it right, can u take a look and lmk???
Over, for example, something like:
This is the same “hi” where you are expecting me to respond — waiting on me to say “hi” in return, only for you to drop the request on me then. Please don’t make me work for your request — in my view, this is rude. Send me your request and let me decide whether I want to commit to it and respond. Let me know what I’m walking into. It’s totally possible to upfront the request in a way that isn’t rude or demanding. To me, the “hi” message feels more rude and demanding than the two other messages, which do not feel that way at all.
As a side note, I tend to prefer casual conversation with my mentees (as shown above), but I’m sure there are some people who don’t. I don’t have strong opinions about this. In my view, casual conversation is more efficient and wastes less time, and I don’t ever view this as impolite. It’s possible another mentor might feel differently, but I’m not sure. I guess, as a mentee, you just feel it out and match their energy.
If you can, please don’t be demanding
Similar to that which is suggested above, I would exercise gratitude and try to appreciate what your mentor is doing for you. I understand that it can be frustrating to be desperately looking for job — other than literal children, there’s probably about a thousand people on earth who’ve never, ever had to look for employment. It is terrifying, especially when bills are due.
But your mentor knows this firsthand, too. They feel — and have felt — the same pain. So please don’t use language that is intended to be demanding, as if we don’t know what it feels like to be in your shoes. If you want to be mentored by us, give us a reason to want to — please don’t cold message us with things like “hi, please can you give me assignments” or dump a copypaste of what’s obviously an interview prompt, saying “with your experience, can you please advise.” Personally, I would not talk to someone this way, as it seems like most people would find this to be rude, demanding, and far too assuming. I expect the same treatment in return.
If you’re interested in talking to us, please talk to us like we are human, rather than dogs waiting at your every beck and call. The best way to do this is to understand that, truthfully, we are extending you some charity — and only because we feel emotionally moved to. At any time, we can stop performing this service for you. Please remember that we are doing you a favor.
If you can, please don’t be entitled
I talk about this frequently, but getting into tech is hard. I understand that design programs misrepresent this, and do not disabuse students of the misunderstandings they cause, and I’m really, sincerely sorry to hear that. I wish they were incentivized to provide better services to their customers.
As it stands, they teach students that designers sit around “mapping” stickies all day, making “competitive analysis” charts, generating fake information to put in “persona” posters, and other nonsense. If you’re honest with yourself, I’m sure you realize there is no way this is a real job. Secretly, it feels too good to be true, doesn’t it?
That’s because it is. This is a severe distortion created by people who are not designers, selling theory about “how design is done” from decades old books written by liberal arts academicians. There is nothing wrong with decades old books written by liberal arts academicians, but you’re not going to find a lot of great information in there about how to compete on the market for a software job from a liberal art academician from the 1940s. Please keep in mind that you might have less information than you think you do.
Your mentor is trying to help you, and they have to decide if they think you can handle hearing these truths that, if you went through a design program, you paid a lot of money to avoid. We are in a really awkward situation where hearing the truth means you’re going to realize that you just lit fifteen thousand dollars on fire.
For a real life example, I was on LinkedIn and saw an individual who I was connected with (through an early career Discord server I helped in) post something that I felt really sorry about. The individual spent money on a course, and remarked that they were desperate, willing to “do anything” to get a job in design — that they are a single parent to a child, a veteran, and facing hard financial times and that, if anyone had any leads, to please let them know.
Obviously, I saw that post and felt horrible for the individual. I reached out, letting the individual know I was so sorry, and found their situation painfully relatable, and that I wanted to help them get industry-ready, if the individual was open to that. Weeks prior, I’d reviewed this individual’s portfolio on their request — it was clear to me that that the visuals and content demonstrated in their portfolio were leaving them in a situation where they were completely unhirable. I don’t think the individual saw that.
The individual responded, saying only “do you have a job for me?” I remarked, “I had in mind 1:1 mentorship,” to which the individual responded “ok.” That was the end of the conversation, from my perspective.
This is what I mean about not being entitled: the individual claimed that they were willing to do “anything” to get a job — except doing what is required to get the job.
Another anecdote, different individual: a mentee booked me after reading my articles on the value of design programs. I essentially restated everything they read in the opinion piece they booked me over, and they remarked: “so you want me to start over?” Please keep in mind that your mentor doesn’t want anything from you — we don’t get anything out of this relationship. This is all a favor we are doing for you, and we simply ask that you show some gratitude, and not feel entitled to a six figure job because you believe you deserve it.
If you don’t want the help, please don’t book us. If you don’t want to work hard, please don’t pay someone ten thousand dollars for a design program that makes tech seem easier than it is. These are six figure jobs — I’m not sure what about earning a ton of money would lead someone to believe that there isn’t going to be a ton of work to get there. Please be realistic.
Another anecdote: an individual booked me after reading my articles, and I repeated everything I said in the article, and then the individual remarked: “on top of everything I have to do for my bootcamp, I’m not sure that I can find time to work on my portfolio on my own.” That’s fine — six figure careers are hard to build, it’s true. The upfront cost requires a lot of effort be put in. Not everyone is interested in doing that. But, if you don’t want to work hard, please realize that before booking us.
If you can, please realize that we can’t give you a job
We understand that you want a job — given how many people in tech have been laid off in the last few months, alone, we also feel your pain. However, we can’t conjure up jobs for you. Most of us are just regular ICs and managers at companies and, while I’m sure most of us would love to help, we’re likely all just as disposable as anyone else, as the recent recessionary responses have shown. Most of us don’t have the power to force our team to hire you — a CEO or VP could do something like this, but this is also extremely atypical. So not even they really “have” the power to do this. It’s hard to knock you for asking, I suppose.
At times, I’ve had ex-colleagues ask me for my recommendation when hiring on their small team, but most of us will only recommend people who we sincerely would succeed on that team, and be an asset to that company. Regardless, this isn’t the most common situation to find yourself in, anyway. Besides, we can’t make someone hire another person — just like you, we still have to compete for jobs, too.
We’re not “gatekeeping” or otherwise withholding jobs from you. We just can’t do anything for you right now. We’re not sitting on a list of “designer who’s who”s, and intentionally making sure you’re not on it. We are regular people, just like you. Our relationship does not have to be adversarial.
If you can, please only talk to us if you’re truly interested in us
As mentioned, we almost would never find ourselves in a situation where we could somehow make you get hired somewhere. That’s not how tech companies really work.
I understand that, at least for me, I work on a super fancy product. I totally understand why someone would want to work on said fancy product — I work on it and, I, too, want to work on it. However, I hope you’re interested in talking to me for more than just being able to tell friends and family that you talked to someone at The Bird Factory LLC or The Instant Gram App Company or whatever else.
Please keep in mind that, at least for my part, I’m a random person making software at a company. I also sometimes write stuff on the internet. We’re all just people here.
As your mentor, and as human beings, we’re going to, at times, say things that you may agree with, and also things that you might not agree with. Ideally, you want to build a relationship with us not to collect a Pokemon card, but to actually hear what we have to say, and determine if our counsel is right for you.
I feel like I have more in mind, but this has gotten so long, so I’m going to end it here. I feel like, when anyone verbalizes those unsaid expectations, they can sound kind of high maintenance. I promise that’s not my intent! I’m not trying to be funny or anything, it’s just that I encounter (what I believe to be) extremely entitled, rude, and otherwise argumentative behaviors so frequently in mentees that I’m starting to wonder if it wouldn’t be beneficial to share these views.
Me, personally, when I encounter a mentee like this, I actually stop investing in the relationship. I don’t know that the mentees engaging like this are generally aware that their entitled behaviors and self-limiting mentalities are what could be playing a significant role in the lack of opportunities they see on the market. I think that, with an attitude adjustment, it’s possible to make changes that result in a higher propensity for hard work, grit, and humility, which I think are important traits towards building a successful, expensive career.