How to find a great Mentor

Nikhyl: Hi everyone. My name is Nikhyl Singhal and I'm your host of The Skip podcast. As all of you know, The Skip podcast is really designed to help you get ahead in your career.

And one of the most common questions that I get and many of you are asking is around mentorship. What does it mean to me from a career point of view? How do I find the right resources? How do I navigate career with other people? And in some cases even, how do I become a mentor? It's a great topic.

It's a complicated topic. In fact, I've gone through a few revisions of this episode and hopefully this one sticks. But, I think it's one of the most important topics because it connects with people that are looking to get ahead. You know, if you're asking about mentorship, it means that you really do desire someone to help you in that sidecar position through one of your most important assets, which is your career.

This episode is structured a little differently. I'm using kind of a Q and A format.

The questions aren't actual real people, but they're representative of all of the different conversations I typically have on this subject, and it'll keep things moving a bit. And we're gonna cover three big topics.

One topic is just how to navigate the resources from paid resources, free resources, communities that are out there, content that's out there. The second, and probably the most important part of this podcast is just how to be coached and how to ensure that your coach is doing a good job. I think that these are both skills, they don't come naturally. And then the last is sort of tips and tricks of things to avoid or lean into as you're navigating mentorship.

So without further delay, let's take some questions.

Okay. The first question is, my manager is really experienced and we have a great relationship, and I'm fortunate to work at a company with a learning and development program, but every year I feel like I'm not doing enough to advance my career.

Now this question comes up because I think that there's this conflation historically between what you need to advance your career and what the company and the manager provides for you.

And this is worth spending a moment on it because I believe that you have to take control of your career. You cannot leave that to the company or your manager, and mostly because the manager in your company have a different incentive than you do when it comes to career. The company wants to make sure that they are succeeding, they are driving the right value for their customers, and when it might not be connected with your career needs, your career learning, your career ambition, the company is not going to turn its direction in favor of you.

That makes sense when you think about it, but it also means that if you're just outsourcing your career to the performance ladder or to the manager and their feedback, and then you're connecting your success or failure and advancing within the company as your success and failure with career, you're doing the wrong thing.

You need to advocate for yourself. Now, this wasn't always the case. It was the case in the past when growth was not moving as quickly. Pre-internet people would go to conferences or go to their company or go to their manager, and they would stay at companies many, many years. But today, I think all of you know that tenures are short.

The internet has made growth much, much quicker. Technology has really transformed all of these different industries that we work in. And as a result, the breadth of skills needed are much, much greater than ever before. Succeeding in one company doesn't mean that you'll succeed in a different company.

And so what I love about this question is this idea, this anxiety that, hey, I think I should be doing more towards taking control of my career. I should be investing in my own resources. And naturally we're gonna use the rest of this episode to really figure out which resources and how to do that depending on your situation.

But I do want all of you to recognize that the way that your say, parents' career navigated isn't the way that you need to.

Okay, so next question. I am not in a position to spend money on paid resources. I'm trying to hustle and reach out to people, but my LinkedIn requests go unanswered. My friends aren't that experienced, and the few leaders I do know aren't that interested in helping. What can I do?

This might be the most common question that I tend to get. I do get a lot of inbound requests on LinkedIn of people that are looking for coaching. I think that generally, you know, in a coaching relationship, the coach has to have some incentive. There has to be some reason to invest in you.

And so my number one piece of advice is to ensure that you are reaching out and trying to connect with people that are somewhat known to you, that are cheering for you or that have a reason to advocate for yourself.

So for me, I tend to coach people that I directly know or have encountered in the workplace, or that I get referred to by someone that I really trust. And that would be your first goal, is to find people that you either directly know. Or find people that can refer you to those individuals who you think can really help.

I think you want to avoid the blind emails because there isn't a clear incentive and we'll talk about the types of things you can be doing instead. It really comes down to two buckets.

One are the paid resources, the executive coaches, and eventually we'll talk about the therapists. But I think that the other pool are those that are just really interested in helping you. And now of course the question is, well, how did you connect with those folks and who might those be?

So four buckets of people that I stayed in touch with over the years.

My first is ex managers. You know, these are folks that know your work. and today your manager will one day be an ex-manager. So though I don't suggest that you solely work with your manager on your career, I do think that they have an important signal to provide.

And interestingly enough, as they go their way and you go your way, it's actually very powerful to stay in touch because they can understand how your career might be evolving better than others because they have context. And oftentimes your manager might be going places and so staying in touch can actually be very, very powerful.

I mean, that's especially true when they leave the company because they can say things that perhaps they weren't as comfortable in saying before because they don't have any concern. They can say that, yeah, you know, though, we were trying to develop this one area, I have to say you were in a really tough situation.

Or they can say, you know, though you were being promoted, you know, it was very thorny to move you forward because of this area that frankly, I didn't really speak to you about because it wasn't part of our company culture. So stay in touch with your manager. Go find your ex managers.

The second group are the ones that are just a click away. These aren't your current managers, but these are the folks that are perhaps peered with your managers, maybe in another function or working in another team. They have visibility into your work. They obviously want to see perhaps the project or the company or the product area succeed. They know how things get done, and again, a little less encumbered by the challenges of managing you directly. Now, in both of these cases, your ex-manager and a peer manager, these folks don't need to be in weekly conversations with you.

They might be connecting with you as infrequently as annually because the goal is to just give them a sense of where you're trending, how you're doing, and how you're evolving, and get their advice on how to pull you forward. After all, they're managers, so they spend a lot of time thinking about these tools, development area, and how to unlock people's career.

And the third group might be not so high up in the organization. It's less about looking up and maybe looking sideways. Think about the peers you have, your colleagues. They're also gonna go places. And more importantly, they are very interested in seeing you potentially succeed.

And frankly, you might have a lot to offer them. And so connecting with your peers, asking them and openly discussing some of the challenges you might be facing and some of the wins that you do have, talking about how you think about career, and then listening to other people that are at the same place and how they're navigating it is incredibly powerful.

And lastly, don't forget the personal relationships that you encounter outside of the workplace. Friends of yours that might be, again, senior in another organization or might be doing something similar to you, but in a different company, different setting, are great people to talk about career with. All of these folks would do it for free.

Some of them are more interested in investing because they're incented in the same way the company's success or the project success. And some of them because they're friends or because they're peers, you might be able to build quite a relationship with in a natural and organic way. But in all cases, talking career with people that are in this focus area is dramatically better than trying to reach out to a so-called professional on LinkedIn or in some email that they've never heard because these folks have incentive, while those don't.

So maybe a framework that I use for this is I want all of you to have a board of directors that are helping you in your career. Board of directors implies not just one or two people, a whole set of individuals. Those that might be offering contradictory advice might be at different levels of seniority and have different context that they can share with you about your work.

I've talked about careers as being managed like a product, and for the product managers out there, I really like this idea of reverse engineering your next step like you would reverse engineer the next version of a product. But in this case, I'm actually thinking that maybe we expand that so it's less about

building a product for your career, thinking about your career, almost like it's a company where it has a board of directors and it is giving you advice but not necessarily telling you what to do. Your job, of course, is to synthesize that advice and find the right signal. Now, you might be asking me that, boy, you know, that's a huge amount of time that you're asking me to put into this.

You're telling me that I need to spend time finding a whole set of board members to work on my career by connecting with people that are in my current orbit. And that seems exhausting, let alone like, where am I gonna find the time? It'd be so much easier if I could just pay someone.

One person that can be with me where I can just convince someone who might be really skilled to just engage with me. And my sense is that's a bit of a red flag, because when we're talking about mentorship and career, you are telling me that you're looking to invest. In something today that will pay off in the long.

Now, if you have a specific spot concern, hey, I need to make a decision on leaving versus going, your ideal situation is you have that board of directors. You can bounce it off of those that come to me and says, I don't know who else to talk to. I'm like, well, you know, you could have thought about the fact that you are gonna have a long career and lots of questions and lots of transitions that'll be in your future.

Why didn't you build your board of directors if you spend 30 minutes a week, which is one meeting? Think about the different types of people that are in your orbit and connect with them. Not in the form of networking, but in the form of genuine conversation, friend finding. Hey, love to share with you some ideas that I have and get your take.

People love talking about themselves, listen to what they've done successfully in their career. Understand how they've navigated, understand how they're thinking about navigating the future. Share with them, your thoughts. Talk about the challenges you might be facing development wise, but do it with people that are incented and then stay in touch with them.

That's the key part, because if you spend 30 minutes a week over the course of a year, that's 50 conversations. If you do that for 10 years, that's 500 conversations across dozens to hundreds of people. And that drives a lot of luck, a lot of connection, and a tremendous board that you can then call upon when you need to ask a question or when they need you to help them. You can be there with them.

In the end, this is a skill and this is something that's a time commitment. You have to prioritize it. But my hope is that with this investment and knowing that it's a bit of a numbers game, you'll have the free, unpaid resources around you that can be advisors for the rest of your career.

Okay, so next question is, what do I do if I just can't find folks to invest with me? So I made this statement that there's a lot of people in your orbit that you should connect with, but I also recognize that a number of listeners are just not in a position to have those professional relationships around them.

Now, in the past we used to say, well, they would go to conferences, you know, oh, maybe you should get an advanced degree. And those aren't necessarily bad things, but they're just highly inefficient. When you think about the conferences that you went to or even the things that you learned in school, not a lot of those apply to questions like, should I stay? Should I go? Or, I'm having this thorny relationship at work. So it's a tricky one to use this as the only way to career advance so this is one area where Zoom has really helped, or video calling in general. Now, staying in touch with say your ex-boss is just so much easier, because you're in a position to do that over video, regardless of how busy you might be.

I think that being able to stay in touch is a skill, but certainly doing that over quick calls or phone calls while you're taking a walk and they are too, is just possible than it wasn't before.

I also think there are startups that are more and more emerging trying to connect mentees and mentors together because there's a lot of people that want to expand their career by coaching others, many people have that desire. And in fact,

I am an advisor to one of these called Meander. These companies are all trying to crack the code virtually on connecting people together, and so don't give up if you feel like there's just not someone in your orbit and you don't have a lot of cash. There are ways to use [00:15:00] marketplaces and networks and startups to be able to connect you to people on a one-on-one basis,

But the big piece of advice that I have for folks that don't have one-on-one resources available to them is to look at the free content on social media. I think it's tremendous. Now, that's not just because I happen to have a LinkedIn presence and I like pushing on Skip and the podcasts and the newsletters that are out there, I've been noticing are just getting better and better over the years.

Lots and lots of professionals are trying to scale and give back, and the way they're doing that is by composing content. And by doing so, you might find some of the best advice that you might ever receive in some free nugget, in some post that a Shreyas or a Lenny posts that I think is worth not only seeking, but really spending 30 to 60 minutes every week, prioritizing time to go through career content that's on the internet that could be valuable to you.

I think the signal from that is so much greater than an advanced degree because you're in a position to see someone solving a specific challenge, a specific problem that might apply to you today or tomorrow.

Now as content has really advanced over the few years, there's an emerging trend that's coming up called community. Now I'm a huge fan of community-based learning. I think for the vast majority of folks who haven't been able to connect with enough professionals on a one-on-one basis, they haven't connected and created a board of directors, and they may not be in a position to seek paid resources. Community building is incredible.

What do I mean by community building? It basically means a group of people that are in the same or relatively similar area of expertise that are also at similar stages of career. Talking openly about the challenges they're facing and the solutions that they have. Now, I built two of these, one, which we're launching in the fall called Skip Stars, and one called The Skip CPO Community that's almost three years old.

And what we did is we identified a small number of people that can be part of a Discord community, an email list, some meetups Zoom calls or content conversations or therapy sessions. And what we find is that learning really happens when you're able to be yourself and talk openly about what's working and what's not with other people that are really in a similar position.

And so community building, especially with the internet, is so much more powerful than it ever has before. And my guess is that if all of you found yourself in the right community, whether it's in your company, whether it's in your local area, whether it's in your industry, whether it's something that you create and go find folks to join. That'll be the number one ingredient to your learning going forward.

So pausing for a second, I think make sure that you're spending 30 to 60 minutes a week finding the right content that you can read that applies to you. And seek a community. Don't just give up. If you don't have that quote unquote board of directors today, those two resources, community and content can be transformative to your mentorship needs.

Okay, next question talks through paid resources. As a leader, I know what got me here isn't what gets me there. And I also know that I need more than my manager and the company performance management system. So much of the work here seems art far more than science. I'm willing to spend money and so is my company. How should I think about the available resources?

Now, this question comes from this gut feel that increasingly it's less about the knowledge and more about the soft skills. It's not what you're doing, it's how you're doing and coaching soft skills or areas that are much closer to the heart require a level of emotional intelligence that is hard for folks that are untrained to provide.

This is where a lot of my conversations go, where I'm looking at private, personal, emotional challenges that people have in almost reinventing themselves or their mindset, to go after something new. You know, examples might be how to manage burnout or how to deal with a cultural mismatch with a company or the boss, or how do you think about discrimination and whether it's a perception or real or how to partner with a peer that isn't really working out or that has values that are very different from your own.

These are really tough problems. Most managers are ill-equipped to just answer the question, which is why there are resources available to help you. And I think that if you're asking this question, you almost have concluded that it's probably inefficient to use trial and error. You know that you need an expertise beyond just trying things out or talking to your friends.

And so my suggestion for all of you who are senior in career is to have a paid professional in your life, helping you on career challenges. Now that could be a therapist or that could be an executive coach, and we'll tackle both of them here in a second. I don't think it's a critical need when you're earlier in career.

I think the content that's out there can very much apply to you. And I actually think that a lot of the peers and the managers and your peer managers can be very, very effective because they have context. But as you get further along, the context may not be as necessary as the skill in helping you navigate.

And that's the reason why I think all of you that are senior need to have this professional and hopefully you're able to afford it either because you work at a company that wants to invest in you or you do have an additional amount of income and it's a very good return on your investment.

Now with both executive coaches and therapists, there's two things that I immediately call out.

One is that they're professionally trained. Unlike myself, there are folks that have actually gone to school in many cases, have PhDs or they've built an expertise over perhaps decades to ensure that they understand how to provide coaching in a formal way. They have the psychological training, they have the understanding of how to partner with clients that I think you'll very rarely find in an average person that you just encounter in the workplace.

And the second thing is that they can provide structure. They can pull information out of you and hold you accountable. And a lot of people that ask for mentorship, they should ask themselves is what you're looking for knowledge, or is what you're looking for structure, and the answer could be both.

There might be cases where the structure that the person provides, the accountability of helping you think through things is actually very powerful because you find yourself so tired, so unable to invest that you need someone to kind of keep you on track. That structure for executive coaches can actually be some powerful tools.

If an executive coach comes to you through your company, they may have a lot of data that they can share with you around other challenges. Anonymously, of course, that other people at the company are facing. And that's incredible data that maybe your manager or others don't have. They can share with you feedback that you might be able to get, that they can go and acquire. 360 feedbacks and being able to say, hey, we really want to invest in this person.

What do you think is really going on? What's their strengths? What's the weaknesses? Again, the punitive damage of telling a manager of a peer, that the person has a development area many people they recoil from, that they don't want to damage the career of their peers by giving them a harsh feedback.

But in a setting where an executive coach is asking, you know that it's confidential, you know that it's not gonna be used by the company in some way that could hurt your peers. And most people want to see their peers succeed. So this level of detail, structure, feedback is incredibly powerful for many people to unlock development areas that are really hard to identify.

And lastly, their expertise often comes because they've worked with people at your stage for years. So they can share with you patterns that I think are really powerful, but they don't know your function.

So an important member of your board of directors, if you can afford them, but not a substitute for all the other resources that we need to bring to bear on your career.

Now, the big unlock for me and for many of you, is to actually work with a therapist, which is different from an executive coach. Executive coaches are really professionally focused, although they have oftentimes some overlap to the psychology of work. I think that a therapist starts with you and looks at you from a personal setting.

Often the company is completely disconnected from any therapist that you might be talking with, those healthcare plans sometimes do cover some of the costs associated with therapy. Now there's a social stigma, particularly in the US where people are reluctant to say, hey, I'm working with a therapist. Well, I use a therapist, and the therapist that I use helps me on three areas. One is they help me reconcile and translate feedback that I don't understand. They help me understand the quandaries between heart and head filled decisions, and they always check in on the sort of collision between personal and professional life.

Most people that I know that have effectively worked with therapists feel like it's the number one resource in their board of directors. They're that powerful. So if you can get by the cost, the stigma, and frankly the amount of time it takes to find someone and invest, because it's a dating exercise, you meet a few, some, you'll hit it off, some you will just not connect with.

But once you find someone and can meet with them on a regular basis, they'll have context. And with that context comes an advancement of your soft skills and an advancement of retraining your mind to help you unlock professional boundaries and obstacles.

Okay. Now that we've covered some of the resources Let me move to the second phase of this podcast which is the skill around being coached, being mentored.

And you know, the question that people ask me is that, well, can everyone be coached? And my answer is no. Having talked and worked with a lot of people, I find that it takes just as much skill to be coached as it does to do the coaching.

So let me explain what that means. I'll start by something very simple, which is efficiency and communication, especially when you're trying to connect with people who aren't being paid, who aren't professionals at pulling information out from you. the fact is that everyone's really busy, and if you're not in a position to quickly organize your thoughts and tee up a specific thing that we can talk through, it becomes very difficult to maintain a relationship, particularly a professional one.

My biggest piece of advice is that you need to ensure that if you're going to embark on connecting with lots of people, don't start out with like, hey, you don't know me. I'd love for you to be my mentor so that we can just talk, where I can just spend an hour, tell you all the things that are on my mind, and then you can somehow figure out how to advance me.

That's to me so unstructured that you're never gonna get a hit rate. But if you were to change your mind and you were to say, look, before I go out and talk to someone I'm gonna send a quick note. And I'm not going to use something like help me with my soft skills.

I'm gonna say, hey, when we catch up, I really am working on how to be a better listener. That's the soft skill that I really need help on developing. I'm curious as to what's worked for you and how do you think I'm trending in this? Or maybe what I did in the past. Did you feel like I had strength, weakness, or development in this arena?

Similarly, when people come to me and they say, should I take this offer? The first question I'll ask them back is that, well, I can't answer the, should you take the offer, but I can answer, is the framework you're using for the decision, a good one. And we can go through that framework.

So if you share that ahead of time and say, hey, I wanted to have a conversation specifically around the framework I'm using to make this decision. It's much easier to react to and I can have a very successful conversation with you and feel like I'm adding value and also feel like I'm getting to the core of the information very quickly.

Similarly, I don't agree with my manager's feedback is replaced with, here's the feedback my manager gave me that doesn't match this other data I've received, or I need someone to help me grow in my career. Is something different than I'm trying to prepare myself to be a good manager? What are the starting points that you use?

Again, specificity and clarity of what you're asking is a key part, providing context. And obviously you can make the other error, which is some people are so efficient. That they don't provide enough context so that we can have a normal conversation. And this isn't just with a senior career mentor. This is just with even the friends and the acquaintances and the colleagues. If you're gonna have a quick conversation with someone.

And if it's not purely social, if you're trying to get at someone's professional life, or you're trying to basically share a decisioning or something that's on your mind, you just have to make sure that you get good at presenting just the right context. And sometimes it helps to write things down, even if you don't share it ahead of time, because then you can take a moment, take a breath, look at what you really are trying to communicate, and with that structure, really provide some value for yourself and for the other person.

And if you're relationship building, the goal of a first conversation is to have a second conversation. And so if it goes well and the person feels like they added value and then there's chemistry, there's a good chance that they'll keep the door open for the next conversation. And similarly, if you not only take, but you give, that also leads to that second conversation and moves things forward.

The second area is to discuss the courage it takes to listen to feedback. Now, I can't tell you how many people sit down with me, work through a specific area. And then I just don't see them take any of the advice. Now, I'm actually fine with people who make their own decisions. I'm not expecting people to make a decision based on what I've suggested, but I do think that there's a lot of people who hope that the mentor will say the same thing that they were planning on saying.

And in many ways, what I'm actually trying to do is not only be provocative, but actually to ensure the person is thinking through things long term. And I'm looking for you, is to be efficient in your communication, but also have the courage to listen and absorb and challenge yourself.

And most importantly, your goal here is to have a diverse board of folks that are interested in your career that can challenge you and disagree with some of the directions you're going. And then put you in a position to decide on what signal to pay attention to, what signal not to pay attention to, but not do it because you're afraid of change or you're afraid to open up and talk to people.

It's actually reversed. Openly, get as much signal as you can and then charter course. Sounds a bit like products where your goal is to talk to as many people as possible about your potential product or the product you have in market. But it doesn't mean to do everything that they say because everyone knows that if you do everything the customer tells you to do, you probably won't build the right thing.

You'll build what the customer thinks is right. Not everyone's gonna have the context about your situation, but the more signals you get, the more patterns you see. But it requires you to have a ton of courage to absorb this feedback and then make the right next step.

And lastly, the thing that I wish people did more of, and I would say 95% don't, is beyond just having efficient communication and the courage to take feedback. The third is to run an efficient process, and what I mean by that is make sure that you are scheduled.

Make sure you give context ahead of the meeting. Make sure that when you have the conversation, it's effective. Follow up. I love seeing the emails that say, hey, we had a great chat, really love this piece of information I pulled, here's what I'm interpreting. We talked about, and by the way, let me know if I can help you with X or Y that we discussed as well.

Now, for folks that I don't know very often I want to stay in touch with people and I want to see how they're trending because it helps me understand, did the advice that we talked about land and so an annual or a six month note that says, hey, here's how I'm doing, isn't actually selfish.

It isn't actually bother, it's the reverse. It's, oh, well, I really wanted to help you. I spent some time, we had a conversation. I'm sure some parts of it didn't resonate and some did. Now I'm curious as to what's the next part of the story. And if I hear that, I'm like, oh, that's great.

Maybe I'll drop you a quick note or maybe we can grab lunch and we can talk through what might be next. This is what I mean by relationship building, is this process of being clear, being courageous, and ultimately following [00:33:00] up so that there is accountability, is the type of relationship building that leads to a tremendous board of directors.

But it's a skill. It is not that everyone starts out this way, and so when you don't have the paid resources to go after the top notch folks, or you're not in a position that people are interested in investing. When we now talk about, look, there's great content, there's great community.

We're in a position where you might be able to build the skill to be mentored effectively, and then you can connect and friend find around you. And with community, we have a very rich definition of mentorship that is very different from just randomly pinging people on LinkedIn.

People ask me like, can I get better at being coached? And I would say that the idea of having courage and the idea of running a process is actually more of a mindset and effort. It's a prioritization. Self-awareness, concise communication is not easy for everyone. Those are things that people can develop, and this is my point that I would say paid professionals tend to be very good at working with folks that perhaps don't have the concise communication and they don't have the self-awareness, and they can pull that out.

That's a lot of what their training is designed for. So when you find yourself in a situation where you're mainly working with free resources or ad hoc resources, you really have to have much more of a skill to be able to mentor yourself. But on the other hand, if you're further along in your career, you're busier, you need someone to be accountable, and ultimately you're struggling a little bit with self-awareness or concise communication.

You're not quite sure what to work on. Well, that's where the dollars really end up helping you.

But maybe the last piece of the puzzle to build better coaching skills is maybe the most unobvious, which is to be coached. It really helps to also coach others.

I believe you need to spend five to 10 times more in coaching others than in being coached. Coaching others just improves your skills in being able to quickly understand a situation, process it, provide feedback, understand the context in a quick way. Look beyond what is actually being presented and look around the corners. These are all important career skills for yourself.

And so when you find yourself mid to late career seeking others, see if you can spend some time giving back to the world, because what you'll find is not only do the people that you spend time with, really appreciate being mentored and coached and advised, but what ends up happening is you end up getting a bit of rhythm on how to have these styles of conversation.

You end up creating patterns that make sense to you, and then it allows you to tee that up for others when it comes to your own situation. I can't tell you how many times I've given a piece of advice, and then I've sat for a second and I listened to it and I said, huh, that applies to me as well. But I never really teed it up.

But that is incredibly helpful. And so my wish is when you want to skill build for all of you seeking mentorship, make sure it's an even trade. Make sure you're putting as much into the world as you can, and ideally far more, because I think it'll be just as career additive, frankly, than finding that perfect mentor.

Okay, this is my favorite question, which is, how do I know the advice I'm getting is any good?

And I am maybe a little bit curmudgeony on this one because I think coaching's a skill. We've talked about the skill of being coached well, obviously to be able to coach is quite a skill. I find that most companies have mentorship programs that they've set up, and I only ask the question. I'm like, well, it's great that people are connecting with each other and being mentored.

How do we know the people that are doing the mentorship or actually giving good advice? More importantly, those that are oftentimes the first in line to do the mentorship thing actually have a lot of time because they aren't particularly hardworking or they aren't on important projects. And so you start to wonder like, uh, you know, this mentorship thing isn't just you finding time to talk.

It's actually a skill in and of itself. So this is perhaps a little too opinionated, but I feel that, too many people in our networks are struggling to be successful operators. They're like, look, I don't love the grind of delivering for this company, so let me just become a coach. I'll take a training session and then I'll become a paid coach and I have this, this skill that I can help people in their careers.

And I don't think that that's a guaranteed miss. I think there are plenty of examples of athletes who became coaches who were not effective, and coaches in sports who are very, very good, but never can play the game. I don't think that all coaches need to be successful ex-professional.

But I would say that if you're seeking advice from someone and you're trying to understand how to manage something within your company and they haven't had that direct experience, you should just be cautious. I much prefer to ensure that you're holding the bar very high on the type of advice you're getting from any professional that provides it to you.

Especially those that have not seen a lot of success to date and are perhaps just finding coaching to be an easier path to a professional career. I think the second piece of advice, and this was something that I spent a lot of time in my early years thinking about, is to be aware of extremists and contrarians.

I see these all the time in people's friends and family. You know, this is the "Quit your job" "Money doesn't matter." "Take crazy risks when you're young." You know, I think that this idea that you should take an unnecessary risk or do something that maybe the person wished they did is a very important cautionary tale. Oftentimes there's these extremists because they like to antagonize. They're a little older. They look back to the younger generation. They think about risks that they didn't take, and then they tell everyone that they should do the things they never did, which I respect.

I think that comes with wisdom. But don't just conclude that, hey, this person was really successful and they told me I should take an aggressive change Just ask yourself, well, what did they do at that stage of career?

And also just chew on what's their motivation? Are they really motivated to help you and who you are today? Or is it more prodding you to think in an extreme way and add that to a signal to your board of directors. And in fact, in board of directors, actual company, board of directors, there's always one or two extremists. That doesn't mean the company goes in the direction. It just helps to have that counter to maybe the company, which is perhaps a little too conservative.

And the last thing that I always ask people to be cautious of is beyond just making sure your coach is an expert and making sure they're not an extremist. But also to make sure that they're not just copying advice of things that work for other people, perhaps even themselves. What worries me is if you copy an advice, oh, this worked for your cousin, you should do it.

Oh, this worked for me and your mom. I worry a lot that it doesn't apply to your situation. Every one of us has a different career path, and I think that oftentimes advisors are not really thoughtful about, Hmm, your career path would end you here, which others in this similar situation would end up in a different spot.

Instead, they just want you to do the thing that is a successful pattern, and I think not personalizing the advice, making sure that it's qualified and making sure. That you're considering it amongst a satellite of other points of view, and then making decision is the skill that you need to have when you're pulling feedback. But also, I would say if you're a coach, ensure you're [00:41:00] not falling into any of these three traps.

Now, the biggest piece of advice that I have on this arena is making sure that any advice that you receive is coming from someone who's listening and understands you first. I cannot emphasize this point enough.

People all the time, ask me for 15 minute calls. What they're asking for is, look, I would love to get your counsel and I want to take the minimum amount of time necessary because I don't want to intrude on your calendar and we know we're busy. Well, I never accept because I've never been able to achieve anything in 15 minutes in terms of listening and learning, unless I'm gonna just take some piece of advice that I've given for someone else and just cookie cutter it, it doesn't really work. What I would rather do is spend the time to really understand your situation, and often it'll take 20, 30 minutes in the best case scenario to listen to how is your career journey different from all the other folks that I might have encountered prior to this.

So this is a very helpful point in that if you're talking to someone and they don't have context and they are just spouting advice with relatively little information, well take it for what it's worth.

Okay. So as we wrap up, a very common question that people ask me is that, you've been doing this for over 20 years. Who's in your board of directors? I have a pretty rich set of resources that I'm able to, to call on when I do have career questions.

I have a manager at my current company. and then I have the company providing a lot of structured performance. And I love it because, you know, it's rare when someone has incented to be able to provide feedback and help you, but I don't look at it as career advice. I look at it as job advice for the role that I have.

Then I have three to five past executives who really have superpowers other than my own, and that I've stayed in touch with over the years. But it's probably the case that I wouldn't speak with them more than once, maybe every year or two. So pretty infrequent. And I keep them updated and they do the same. And I ask them feedback, and sometimes I'll just signal what's new and what's going on. But I try to build those relationships.

But I know that they'll be with me. When I have time of need. But I also recognize that there are folks that are, you know, different stages of career, so they don't have a lot of time. And I've built those relationships mostly because they were ex-coworkers of mine. They were leaders that I encountered that I really liked. And when I got to know them, I can maintain the relationship.

Then I have a dozen peers that I've also encountered, either because they were at school with me. Or there were folks that I met socially. Some cases there are people that I've coached that have turned around and helped me, in my careers, these dozen, maybe twenty folks or peers that I've collected.

And and those, I do stay in touch, which I see them, maybe a few times a year, maybe once a quarter, and we'll catch up, or I'll do a zoom call or we'll have dinner and we'll just talk through what's going on in both of our lives and maybe something will come up professionally.

And what's really powerful about that is its a great way to be seen, but also just to watch other people's career stories unfold, and being able to connect it to your journey and listen to how they're managing family, or how they're managing their boss, or how they're managing a challenge in the workplace. It's powerful learning.

And of course I have friends that I think are also in the same category where we often don't talk purely about work, but work is such a big part of our lives. It ends up blurring the lines between peers and friends. And now my group that I'm describing is up to 30 or 40 people over the course of the year that I'm essentially staying in touch with, maybe through just text messaging or maybe through monthly dinners.

Now as far as paid resources are concerned, I have one which is my top flight therapist that I work with, and she's incredible and I try to see her, once a month. I used to see her more often when I was in transition, but as I've been in flow, I see her once a month and we talk through things and I don't prepare a lot for those. I noticed that a couple of days before. I always have something that I think is top of mind, and then she's good at pulling out what's the real signal to maybe something that might be early and not quite formed in my head.

And of course, I have the hundreds of folks that I coach that I also catch up with maybe once every few years, all the way down to pretty frequently if they're in transition And so yes, you look at the number of resources it's a lot, but they all provide me value. And so I'm prioritizing.

I like leaning into this because I feel like I'm getting something and I'm giving something up. And it's changed as my family situation has changed as I've gotten older and as people's needs have changed. But it's a broad spectrum is the point I'm trying to raise. In addition to the communities and the content that I consume, this is how I've been able to build my career. And some version of this is something I hope that you pull on as well.

Now, I didn't directly answer the question of, I, I've been trying to get in touch with you. I would love to see if you're open for a conversation, a Zoom call. I'd love to see what your rates are. Um, just to be clear with all of you, I would love to spend more time coaching and maybe one day I'll put more time into coaching and community and all the good stuff that I've been doing on the side, but it's not today.

And what I found when I built The Skip podcast is it was in direct reflection of just my inability to scale. I couldn't meet with all the people that I want to meet, and so I ended up writing and doing this podcast to kind of share as much wisdom as possible. So I politely decline nearly all opportunities to coach or to spend time with folks except for those that come through referral or that are people that I know directly.

I've never been paid for my coaching. My interest is seeing the industry evolve and seeing people that I believe could really change our industry for the better being in charge and finding career unlocks that'll help accelerate their way.

There is one idea I've been playing with and that is [00:47:00] to do live coaching on The Skip podcast. The concept is that if you have a specific thing that you'd like to tee up and you think it might be generally interesting to the audience.

I might be open to doing a call with you, what I would do in this case is I'd record it, and then what we would do is share the conversation to the audience so that not only would we have a chance to understand each other and see if there's an opportunity for me to provide value, but we can benefit the community as a whole.

This fits into my mantra around scaling, but also providing as much coaching and content as possible and being more concrete than perhaps I have been in some of my prior episodes. I would anonymize the conversation so that you would be able to be fully transparent and fully open.

And I'm gonna run some pilots and I've gotten a few folks to, to bite, but this is something I'm really interested in trying and so if you're open to it and you have a specific thing in your mind particularly those that aren't super timely, 'cause I think it'll take a little bit of time to, build this structure

I'd love to hear from you. Drop me a line on LinkedIn or drop me a line on Twitter, and just tell me how I might be able to help.

Okay. To wrap up our conversation on mentorship, I think you know that there's no magic bullet. I think that you really need to organize a board of directors and ensure you have the right skills to connect with the right people that are around you and build an effective conversation.

Successful mentorship is usually a balance between the structure you need, the time you can spend and the money you can spend. My hope is that for those of you frustrated because you don't have the right mentors in your life, change that into ensuring you're spending 30 minutes connecting with the people around you and 30 to 60 minutes consuming all the great content and finding a community out there.

You can do that for free can just transform your career and solve much of your mentorship needs. be specific when talking about mentorship. The more specific you are, the more it'll be easier to find the resources and add value. Connect with the people who want to see you succeed. They have incentive.

And boy, there's more of those folks out there than you may realize. And then also make sure you're giving back, help others because it creates a skill to be able to be coached when you coach others. And lastly, I would love to see if any of you are interested in joining one of my Skip coaching calls.

That experiment could be very helpful and we could transform mentorship together. So thank you for listening to The Skip podcast. My name's Nikhyl Singhal, and I look forward to hearing from you.

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