: Thanks for having me, and I appreciate the time to share thoughts on mentorship. I know that two of the questions that came from the audience are: how to find a good mentor and what kind of advice should a mentor give, but I'd like to add some questions that I think it's important to create context for the whole thing. Let me rhetorically pose a half dozen questions, and then we can address them all. I think it will still get where you want us to get. And obviously I'd welcome any thoughts, Emily and Kevin and anybody else, in terms of all of this, if these will seem logical to you.

I think one is what can mentors even offer in a way it's asking what is mentorship, but I don't want to be quite that philosophical, but literally, what is it that a mentor could offer? Another question would be why can't it just be anybody? Why couldn't you tap somebody on the shoulder on the street and say, could you help me? The third thing is, when do you need mentorship? When in your life, what situations call for mentorship? The fourth question might be, how many mentors might you need? That may seem like a surprising question, but mentors, first of all, they don't come one at a time in real life. Secondly, it seems to me unlikely that one person that could truly do all the things that mentors, might be able to do.

A fifth question would be, who are they, what are the types of things that a mentor can help you solve? And then what types of people, almost a six question would be, how do you find them? A seventh question would be, as a mentor, how do you give feedback? What's the best way of doing it? Finally, it doesn't have to be the last question, but it's the eighth that is on my mind. What might you avoid? what are things, in a dialogue that would probably not be productive? So those are some thoughts for us to discuss.

: I believe that Nirvana exists, in life and relationships and careers. When you can somehow find yourself at the intersection of three things, what I'll call passion, aptitude, and need, what do you want to do? What do you do well? And what do people need for most of my life, I was an investment banker. I worked for one of the large accounting firms, and then I worked for a family controlled investment bank. What I did was I helped people with companies, make their companies more valuable or more liquid, or figure out what their companies were worth. I think I did that pretty well, and it was exciting, but it wasn't necessarily the most meaningful thing I could do in the world.

The reason that mentorship matters to me, that I'm enthusiastic about it is that it's an opportunity to help somebody change a life. By the way, it's not always the mentee whose life has changed. Sometimes it's the mentor. It's just feeling like you're having an impact.

: I wasn't aware of it at the time because people like you didn't provide me the opportunity to even think about it. But, I'm going to pose the question back to you and to Kevin and to Emily, which is, what person or persons in your life would you automatically assume might be a mentor? Who are the most likely people to be a mentor in your life?

: Right? I'm not saying everybody's lucky enough to have parents who can truly mentor them, but the natural position for a mentor might be a parent

: I think, as Kevin pointed out, parents would be theoretically in a good position to provide mentorship. Might be a spouse or a life partner, possibly, even a child. I know it sounds strange, but remember at my age, my children are in their thirties and there are times when they can mentor me. Now, I do think there's a high correlation between good mentorship and wisdom. Wisdom is not to be confused with intelligence or smarts. Wisdom is the combination perhaps of intelligence and experience. You're more likely to have that when you're my age than my kids who are half my age. I should also preface this by saying, when I look at my own life, why do I care about mentorship in terms of where I've been?

I told you that, I feel like I was doing interesting things, exciting things that I was good at, but they just didn't have sufficient meaning for me. I've had a chance to be a mentor for my kids. I've been living for nine years in one of Yale's colleges as a resident fellow. That means I've been living literally really among the students, which by the way, makes for noisy Friday nights. It also means that, I've had the pleasure, the privilege really of getting to know generation after generation of students and providing help. So, for me, whether I realized it or not, I was exposed to mentorship as a mentor now for quite a while.

: I'll just mention a few things. One is holding up a mirror so you can see yourself better. You know, I'll call that personal insights. Another, which might be the opposite is helping you network you, and maybe there's simply, maybe you just don't feel like you have natural networks and a mentor could help you either point you toward networks or lend hers or his, to you.

Another thing could be as mundane as reviewing a resume or practicing interviews. And, what about, coming to a fork in the road, whether it's a career decision or a life decision could be a divorce, could be a marriage, could be, whether it's start a family or buy a house, could be changing jobs, looking for a new job. That's an area where mentorship might matter. Finally, and again, this may seem mundane to you, but some mentors can simply help you with a process. Literally, what are the steps that I need to think about in order to do something? And so, these are all the kinds of things that mentors can offer and you can already see how very unlikely it is that one person would be your mentor for two reasons.

One is there are so many different things I just mentioned, and the other is your life changes as you go through the passage of time. And so your needs change.

: I can actually build on that. So, yes, an advisor might have an angle, although, you can find objective advisors. Part of your question Pianpian is advisors may not be empathic. They may not have empathy. They may be really smart, or knowledgeable on something, but there's this magic sprinkled dust that, perhaps you have, if you can actually almost step into your mentee shoes and feel how they feel. There's that there's, that may be lacking in an advisor, or a coach. I can do the same thing with a coach. I think a coach can be a great cheerleader by the way, a mentor can be a cheerleader too, but in my mind, a coach is relentlessly upbeat almost to a fault.

They're trying to pull a performance out of you. They, so in a way they have angle, it's a good angle, but they have angle. I'm not sure that I believe that's a necessary condition for a mentor to they're just relentlessly optimistic or relentlessly trying to pull performance out of you. They are trying to convey wisdom, but that's different. There's a lot of intersection, but I do think they're different in that way.

: Why doesn't that work? Now that may seem like an obvious answer, but let me tell you six things that I think I want to say, tell you, I want to suggest six things that I think might be embedded in a good mentor and the odds of finding that person on the street randomly, or like winning the lottery in California. One is, somebody who knows you and is upbeat. Somebody who has a generally a positive view of life and knows you. A third thing might be somebody who is objective. Also somebody who's accessible. A fifth element of a good mentor would be somebody who listens well. That's of course, related to being empathic, to having empathy. A sixth thing would be somebody who cares about you. That is empathy. Finally, in addition to knowing you, being upbeat, being adaptive, being accessible, being a good listener, caring you, this will seem obvious is having the particular skills or perspective to help you with the thing you're trying to work out. All of those other things are helpful, but they're not enough if the mentor doesn't have that particular skill.

: I really think it's lifelong at different stages. You need different kinds of things. Maybe very early on your parents might be enough. I think you need mentors when you face risk or uncertainty and or when you need to talk something through safely, by the way, I didn't read that somewhere. This is literally, I'm pulling this out of my ears right now, but when you face risk or uncertainty, making decisions in the face of uncertainty is actually a sign of leadership. Again, there is such a thing as personal leadership, a mentor who can make you a better personal leader leading your own life on purpose. You know, that's a pretty good mentor. Dealing with risk or uncertainty or wanting to talk something through in a safe space, notice those aren't quite the same as each other. When you play tennis and you use a tennis racket, you get very attached to it. You play on and on, but the strings are gradually getting old. At some point, those strings are going to break and it actually makes sense to take that racket to a pro or to a story and get the rackets restrung every once in a while. The third time when you need a mentorship is maybe when you haven't had a mentorship in awhile, even if you don't know for sure that you need somebody, maybe I'm making up a timeframe here, but every six months or a year or two years, you should have that kind of dialogue, even if you're not sure you need it.

: So here's where it gets tricky. Of course you can't have everything. I think I was probably one of them who feel like, I don't even know where would I find a mentor? How would I do it? I just don't naturally know who. You may not always be able to find a mentor, no issue. I think it's going to be immensely easier for that person to be a good mentor if they do know you beforehand, otherwise you need to invest some time, at the beginning.

: One is look at your existing and past routines and social structures. What's the routine of your day, week, month or year? What are the social structures you live in? Of course, there's family and friends. There may be an office environment, pre pandemic and post pandemic, which is another social structure. There may be, and I'm not, this is not a judgmental comment, but there may be faith related places where you have a social structure, like going to church, for example. I'm a racket sports nut. I played tons of tennis and tons of platform tennis. I say, Oh my gosh, I'm so lucky I'm going to make a late life friendship just because I've been hitting balls with that person over here. We have in common and I liked pickle ball. It's fun. So, these are places where you can find people and finally, I would mention friends and let's also make sure that we realize that it might not be current friends. My very best friend when I graduated from Yale was Pete Marwick. At KPMG, when I first went there, my very best friend was a guy. His name is Ron waters. I hadn't spoken with Ron and almost a decade. This morning I woke up at 4:30. I couldn't get my mind to stop working. I sent him an email because I just realized I missed talking with him and, he's calm and he cares about me and he knows me from admittedly decades ago. But, there's a past friend who could easily become a mentor or maybe the other way around. Maybe I ended up as a mentor for him. You need to look, there's this time machine you need to take sometimes to look at your friends, not only present, but also past.

: First of all, empathy doesn't grow on trees. You know, it's hard. Can you develop empathy over your life? Yes. You can, you actually really asked two questions, Pianpian, but how do we know if somebody has empathy. If you're really listening carefully yourself, of course you want a good listener, but if yourself are listening carefully, you'll realize that the questions that she's asking you are customized to who you are, or customized to what they just heard to reflect the pain that she sees, sees that you're feeling about something. It's almost embedded in the question, an intonation or a connotation that otherwise wouldn't be there. An advisor might not be tailoring the question.

A coach probably is going to tell her the question, but the coach is going to be telling her the question to maximize in your peak performance. An advisor might not, a great advisor actually would be empathetic, but, so the answer is, not that there's one answer is feeling that the questions are tailored to you, but not only the Pianpian of the moment, but also the Pianpian of the feeling somehow.

: I think it's important to listen, really, listen, not just hear the words, but, be listening to the words and listening to the feelings of somebody. Like it's hard to train empathy, but it does take time and patience.

: By the way, I think that's an immensely important question. I know part of the reason you ask it is because you picked up on what I said earlier. I really think, empathy is not a necessary condition for everything, but, it tends to be an important trait for leadership. It tends to be important trait for good communication, I think it helps move the world forward. So I'm glad you asked.

: It's interesting the way you asked the question, I almost would reword the question away from mentorship. You're saying people would like to find a role model, that's a few more years along and has arrived at a certain position. Of course, you'd like to find out how that person got to where she or he is. I don't necessarily view that person as being an ideal mentor if you're at a company. I joined KPMG and two years in, I moved from being a traditional auditor to what was called basically corporate finance. It was a back order, a little tiny thing back in 1976 in a large firm. Everybody who knew me said one of two things, they either said, you should, go talk to Goldman Sachs or Morgan Stanley. If you want to do corporate finance, don't do it at an accounting firm, or they said, don't do it at all. Stay in audit, 10 or 12 years from now, maybe you'll make partner and that'll be great. There were a couple of people at KPMG who said, give it a try. One of them is Jim Smith, who was a partner at the firm who did take me under his wing. It's funny. I never really viewed him as a mentor. I certainly viewed him as a protector and a a godfather. He really did help me become a partner over the next eight or nine years.

But, you could of course develop mentorship relationships at a company. I'm not sure that your mentor should be up the same chain that you want to go. I think your mentorship relationships should be a sideways relationship within the company. There's a little bit more objectivity.

: To me, so that's perfectly laudable. I think that's great that, I wish I had thought that strategically of finding people and saying, that's the person I'd like to become, business wise or personality wise. I think when you find those people, that's when you should go to your mentor and start a dialogue about how do I become that person, or how can I step into those shoes? I actually don't think that person becomes your mentor.

: Really good point. It was thinking, like mentor could be like your someone appear closer to you instead of someone like, that you're aspire to, it might be more distant from you, right?

It could be, but, the reason I'm sounding cautious is it could also be somebody who's a rung or two up from you, but just not directly up, maybe one or two up at another company or in another department of your company, something like that. Cause I want to go back to remember some of those characteristics that are so important, and mentors’ objectivity, for example, of separation doesn't mean emotional separation, but it does mean a different kind of separation.

: I don't want to miss anything important here.

: I don't really know the answer to that, but the next thing I'm going to say is going to sound like a cliche. Cause people have said it before, but think of mentors as almost your board of directors, your personal board of directors and, do companies have one director? No, they don't have one director. They almost always have somewhere between 3 and 10. I mean, some boards are even bigger, but that's ridiculous. When it comes to personal mentorship, there's some number of mentors that you need it, in a perfect world at any one point in time, it might between two and seven different people that you need. By the way that the board just like boards change.

To the mentors that you need to change to, which you might say, okay, let's be a little clearer about

: I can think of at least four categories of mentors. You will need networkers. I know I mentioned that word already, strategists, where do you want to be in 10 years? And like, what are the skills you're going to need to get there in 10 years? And what resources will you need? And things like that. Those are sort of strategist. The third is logistician.

Doesn't worry about rejection. Just do outreach and outreach to multiply the number of relationships you have, because I think we would all agree that relationships are really a very important aspect of a meaningful life. Networkers, strategists, logisticians, meaning literally they really nailed the process. Very few strategists are also good logisticians. Very few strategists happened to be good networkers. Occasionally they are.

A fourth thing would be personal development wise people. I know, I'm not saying that very well. I don't quite mean psychoanalysts. It’s people who, recognize who you are as a person and recognize or listen to you, when you say where you think your shortcomings are and can help work with you to change. Address those weaknesses and leverage the strengths. I think that personal thing is different than being a strategist or a logistician or a networker. I'm sure I've left out things, but those are four interesting categories.

: Yes. It means that their aptitude and passion are in one of those areas. I'm not saying you can't find somebody who has more than one of them, but I am saying that it's highly unusual to find somebody who's truly, really good at more than one of them. For example, because if you really want to be clever, you could poke at me right now and say, Hey, Steve, what do you think you're best at? as a mentor. I'll punish myself by answering my own question, of those things. I am not a good networker. Although as you get older, by the way, the world shrinks, it's a weird thing that happens. More people in the world feels smaller. I guess I'm doing better as a networker than I used to. I'm definitely not a logistician. I am just, I've never been a detailed person. I think I'm, it's either strategy, thinking 10 years, where do you want to be, kind of asking the right questions to draw that out, or it may be recognizing or listening for somebody's personal strengths that you can build on or areas for improvement that you can address. You know, so it's one of those.

: Yeah. How do you break the ice? A lot of times it's helpful if there's a go between, to make an introduction. I'm not saying you can't do it directly. I think most of the time people do it directly, but isn't it nice when there's an E introduction of some kind.

The way that you can get close to somebody who could become a mentor is I just don't think it's a great idea to walk up to somebody, even if you're sure they're a perfect mentor and say, would you start a mentorship dialogue? It's like, Whoa, time out. That was, you were in my space. It might be trying to find common ground. That was a very long way of getting to the answer, which is either an E introduction or a real introduction through a go between, or we're finding common ground.

: Yeah. Or maybe you end up helping them in Dutch. I don't know how to speak Dutch by the way, a tiny bit of German, but no Dutch, there's a phrase that has to do with being aligned or collaborating or seeing things we would say eye to eye. They actually do nose to nose. There's some phrase that has to do with noses pointing in the same direction. Now I need to go find it now, of course. But, this is what you're talking about and what we're talking about right now is just finding some easy, low-maintenance kind of commonality and letting some chemistry develop around that commonality. Maybe that person gets to know you better that way too.

: Yes, but not on probably day one and possibly not on day three. I'm about to tease you Pianpian. This is a micro alert since this is being recorded. One of your endearing qualities has always been in the almost decade that I've known you is that you actually, you're very direct. If there's something on your mind, you just say it or ask it. I am saying that when it comes to developing that kind of relationship, sometimes there needs to be two or three intermediate questions. It's a great skill to have when you're doing what we're doing right now, recording a session that needs to fit into an hour. It is important when you're mentoring though, to somehow it's not exactly sneak into it, but ease into it.

: Yeah. I think it almost always starts with something else other than mentorship. It's have you tried this pizza in New Haven since we actually are the pizza capital of the world? A bar pizza just opened up four years ago, have you ever been there before? Let's go there, and just talk and just see where it leads. I understand that sometimes time is of the essence, and that may be frustrating because, I I'm making this seem so natural. Yet what if you really want advice, in the next three days, and you don't have a month to develop that relationship? I don't have an easy answer for that question. I wish I did.

: And I'm going to be literal. I mean, not what you say as a mentor, but how you say it, right? Cause what you say is gonna depend on what your mentee needs, right? Do they need, resume, practice or interview practice. They need to, somebody hold a mirror up to them. It's really, it's how you give feedback. I think there are at least three elements. One is don't give that feedback unless not only have you listened, but your mentee knows you've listened. It's not quite the same thing. Just listening and making sure that your mentee knows you've listened.

Why? Because your advice will have more credibility and impact on your mentee if you've listened. Especially if they know you, listen, they're going to believe you more than if you just pop right in with that advice. This is for the Steve blum of a 10, 20 or 40 years ago. This was a bigger problem than it is now. It used to, cause you can tell I'm a high energy person and that can get in the way sometimes, boom, I want to jump right in and show how enthusiastic I, sometimes I have to shut up and listen for a minute.

The second element of giving feedback is, it's two things combined. It's being direct and being gentle. And you can do both. I mean, they're not contradictory.

If you're not direct that either the dialogue gets complicated because perhaps your mentee isn't good at hearing indirect. I happen not to be good at hearing and direct. One of the reasons Pianpian and I can be friends for the last decade is she is direct, says something, I get it. Kind of going circuitous lead doesn't work as well with me. It's just important to do that. One is the complexity of not being direct in the other is you could lose your credibility. Somebody could interpret indirectness as not exactly dishonesty, but just not being completely there.

Then, the gently, I guess, goes without saying, once you get to know your mentee pretty well, there are mentees who can take tough love. But, I would say the safer way of going at it is, it's doing it in an encouraging way. The third element, so one is listening, the other directness and generalists combined.

On days when you and your mentee can both be mentally fully present. What if you didn't get a good night's sleep? What if, on Tuesday's Kevin's day with the kids, they're, there are things I'm teasing you now, but you get the idea is it really helps if the feedback can be given at a time when both people can kind of be mentally present and that can have to do with getting enough rest, it can be location. It can be day of the week. It can be months of the year could be seasonality. Thinking about that sounds like logistics, but it's pretty darn important. Logistics is you're not always going to be able to do that, but it would be nice if the setting was good.

: One is, try not to make this too much ad hoc. What I mean by that? Spontaneous isn't necessarily the bad, but I think that a good dialogue should have some cadence to it. It should have a rhythm to it doesn't mean that every, two weeks on Tuesday at noon, California time, 3:00 PM,, we should talk. Somewhere in between, there should be some rhythm, I think, to make a dialogue work better. Not having any rhythm makes it harder.

The second thing is this relates to what I had said before. I think times when the mentor or the mentee are both tired or distracted, that's a hard time to have the dialogue. So that's something to avoid.

The other thing is maybe information overload. So, perhaps the mentor has accumulated quite a bit of information. Maybe it's not a good idea to download all of that on the mentee at the same time. Conversely earlier in the dialogue, it's up to the mentor, I think to say to the mentee timeout, you just gave me 18 pieces of information. Whoa, can we just do three for now? so that the information overload can come from either direction.

: Yeah. Again, I apologize if this sounds cliche, but we all need reminders of things. I think the way to do it is to phrase it as an opportunity. Hey, I see something here that could really, move you forward toward the decision you have to make, or, it's like that it's framing it as an opportunity. We all know that famous phrase is the Greek word for crisis is apparently, synonymous with opportunity, crisis opportunity. It's like that it's, even if something seems like a big challenge, it's Hey, I think we can break this log jam, I have some ideas for that. So then it becomes a positive discussion.

: Instead. It might be ideas if that's what the mentor's being asked for. It might be perspectives, you see there's a subtle difference between ideas and perspective and idea might be something out of the field that the mentor, maybe that is something a mentor should do. We, we didn't say that before. That could be a fifth category. Mentor is an idea generator. It's an innovator in your life. The idea is something perhaps entirely new, perspective might be taking what you've heard from your mentee and letting her see it in a different way.

: Somebody asked a question about icebreaker questions. What is a good icebreaker when you encounter somebody for example, at a conference and, it's, it strikes you that you'd like to get to know them better. One, these may seem very obvious, but one would be what brought you here? Who, what, when, where, how, as opposed to the yes, no. So, what drew you here? What was it that intrigued you about this conference? It's something about the environment of that person or what got the person there just to start a discussion? I don't know. I know it sounds like I'm struggling with it, but it's so contextual, depends how you encounter that person. Don't think it's normally going to be, the clothing they're wearing, or the color of their hair. It's going to be something more profound than that. There's been a particular news item that isn't religious or political, there could be some news item that would be relevant to everybody who's at that conference. Of course, you might say, gosh, did you hear the news? what about that? Just as a way of having something to talk about.

: Great question, should have asked that question earlier. What can the mentee offer back? And actually there, I'm going to bifurcate that question into two things. One is, how can the mentor, how can the mentee feel like it's not a chore for the mentor? How can the mentee feel like it's okay. The other is what can the mentee offer back there related? A great mentor is always learning just from having the dialogue, perhaps feeling engaged. Why do Yale alumni mentor Yale students? Partly it's a way to give back to Yale. Maybe the mentor isn't inclined to do something that requires hours and hours, but they do feel like they're doing something giving back to the institution by helping the students. So, the mentee just by having the dialogue is actually giving something to the mentor. I know that doesn't fully answer your question, but what can the mentee do? That's more concrete. One thing I'm saying is the mentees should psychologically feel, realize that a really good mentor probably is getting a lot out of the dialogue and just is inspired by having a chance to talk to maybe a younger person or somebody to help solve a problem. Maybe they feel pretty good.

They don't need to solve a problem. As far as what can you give back? Well, as you get to know your mentor, you're probably going to find out that the mentor has, I don't want to say deficiencies, but areas where they know less. Maybe, more of the classic of course, generationally is, the younger generation knows more about tech, so maybe the mentee can provide the mentor, some technology that the mentor didn't already have.

: Great question. Not one I expected, I think in the political arena, my instinct is that if we had, different ways of creating mentorship, in our political structures, we might have different outcomes than the very difficult outcomes we've had lately. It would be nice if those mentorships could exist across political boundaries. They used to, there used to be people who truly got wisdom from people who weren't from the same party. Can I give you an interesting, this is going to sound like a digression, but I'm not sure it is.

There was a study done a few ago of the political correlations of marriages back in 1970 versus the political correlation of marriages in, 2010 and 2015, 45 years later. Back in 1970, the correlation of marital parties was almost random part is that is to believe you could almost roll the dice and the husband and wife, could be whatever parties we all know that's not true. Now, the correlation is incredibly high democratic Democrat, Republican to Republican. So, and mentorship unquestionably exists in some ways within, marriages. So, I guess I'm extending your question. I don't, that's a really dicey one to how do we, how can we create those kinds of relationships that cross party boundaries and that have a mentor aspect. I think it's greatly needed in our political world and it may, in fact, we needed even in our marital world.

: It was my pleasure Pianpian. Thank you for inviting me.