My guest today is Jason Knight, the creator, host, producer, editor and promoter of the One Knight in Product podcast, a B2B SaaS product consultant, and fractional Chief Product Officer for companies that have gotten to product market fit and need help scaling their product team. Jason is also the founder of My Mentor Path, an inclusive, accessible and cloud-based mentorship service.
Sandra Monteiro, a Product Manager at SAGE Publishing and a mentee of Jason’s, joined us halfway through to share her own experiences with mentoring, how she found her way to working with Jason as a mentor and what some of her learnings and insights from working with Jason as a mentor have been. She also shares her thoughts on what mentees should be thinking about as they search for and work with mentors.
We explored Jason’s mentorship journey and why mentorship matters to him, the challenges of Industrializing mentorship pairing and productizing the matching of the lopsided mentorship marketplace.
We also touch on how to measure the impact of the work and the subtle and important difference between Mentoring and Coaching. Jason suggests that many people who say they want coaching really want mentoring from someone who has “been there and done that”…and that great mentoring leverages coaching mindsets and skills in a practice he affectionately calls “centering”.
Some fundamental questions we explored were the differences and relative merits of FORMAL vs INFORMAL mentorship as well as working with someone INTERNAL vs EXTERNAL to your Organization
One of the big insights Sandra shared was shifting her expectations on the nature of the mentoring relationship from one centered around SOLVING vs conversations centered around TOOLS (ie, being offered relevant examples, learning materials and frameworks, holding space for emotional distance, and being offered broader context for challenges).
Links, Quotes, Notes, and Resources
https://www.oneknightinproduct.com/bio/
https://www.oneknightconsulting.com/
My conversation on Unapologetic Eating and Living with Alissa Rumsey is here
AI Summary
Part One: Daniel Stillman with Jason Knight
The conversation was about mentoring and the challenges of being a mentor. Jason Knight discussed his experience with mentoring and his idea for setting up a platform for it. The discussion also touched on the differences between coaching and mentoring, the importance of honesty and transparency, and the need for mentors to recognize their limits.
Meeting summary:
(0:22) - Jason Knight talks about his path to mentorship, starting with a call center job where he had a mentor, then doing structured mentoring sessions in corporate, and finally offering himself as a mentor on Twitter and getting overwhelmed with bookings
(4:46) - This experience led him to consider setting up a platform for mentoring
(5:20) - Jason Knight discusses the challenges of being a mentor, including context switching and the importance of knowing someone over time for effective mentoring
(6:57) - Jason Knight discusses the benefits of long-term mentoring relationships and how they can lead to accountability and knowledge accrual over time
(9:29) - Jason Knight explains their two-sided marketplace for mentors and mentees, the challenge of matching, and how they encourage multiple mentorship relationships to address the imbalance between those seeking mentorship and those willing to mentor.
(17:16) - Coaching and mentoring share similarities but have big differences, with coaching being a craft that uses specific skills and techniques while mentoring requires experience in the industry being mentored in
(21:09) - Jason Knight emphasizes the importance of being honest about not knowing the answer and exploring together with the mentee
(22:31) - Jason Knight agrees and emphasizes the need for mentors to know their limits and stay in their lanes, recognizing when real support is needed
Part Two: Daniel Stillman with Jason Knight and Sandra Monteiro
The participants discussed the importance of both formal and informal mentorship, with a focus on qualities such as trust, respect, and open communication. The speakers emphasized the importance of providing tools and resources rather than direct solutions, and recognizing when a mentoring relationship isn't working out. They also discussed the value of paying it forward by being the mentor you wish you had in your career.
Meeting summary:
(28:54) - Jason Knight asks Sandra Monteiro what makes a good mentor, and Sandra Monteiro lists qualities such as trust, respect, unbiased perspective, providing tools instead of solutions, and having a breadth of knowledge and resources available.
(33:23) - Jason Knight summarizes the conversation so far, highlighting the value of both informal and formal mentorship and the difference between internal and external mentors
(34:55) - Sandra Monteiro agrees that having both internal and external mentors can be valuable and shares her experience with a previous mentor who was also her manager
(36:06) - Sandra Monteiro shares that her mentor focused on providing tools and resources rather than giving direct solutions, which helped her develop her own solutions and rationalize her thoughts
(38:00) - Jason Knight emphasizes the importance of empowering mentees to make their own decisions and take action based on experience and resources provided by the mentor
(41:41) - Sandra Monteiro emphasizes the importance of honesty, trust, and openness to feedback in a mentoring relationship
(43:48) - Jason Knight explains that while there is an imbalance in experience, mentoring is still a relationship between equals with open communication and responsibility for one's own needs and goals
(46:21) - Jason Knight emphasizes the importance of open communication and feedback in a mentoring relationship, and the symmetry of responsibility for communicating needs and wants
More about Jason and Sandra
Jason Knight is a 22-year veteran of tech & product who has worked for big corporates and scrappy startups. He has been building disruptive B2B products for years and is completely in love with product management. A pragmatic idealist, he has long since realised that product management isn’t always like the books and is passionate about helping product managers, and product companies, survive in the real world.
By day, Jason is a product coach and consultant who works with startups and scale-ups to help them build great products and build great teams that build great products. By night he speaks to some of the biggest names in and around product management, as well as inspirational leaders, founders and practitioners on his podcast One Knight in Product. He’s also the co-founder of My Mentor Path, a platform that aims to make mentoring accessible to all.
Sandra Monteiro is the product Manager for Video at Sage Publishing, where she helps shape the future of Video streaming services for Higher Education in the Social and Behavioural Sciences, across Sage Video and Sage Research Methods Video platforms. She is also a plant collector, enjoys watercolour painting and urban sketching.
AI Transcript
Daniel Stillman
Welcome officially to The Conversation Factory. We're here to talk about all things mentoring. So I'm really curious how you sort of found yourself on the path of mentorship, like, why it matters to you, why you think it's important.
Jason Knight
Well, it's good to be here and obviously thanks for having me again. We'll talk about the other conversation another day. But it's a really good question, like the whole kind of path to mentorship and as with many of my life choices and general neuroses and all of the kind of drivers that I have, I think I can trace a lot of this back to dropping out of university, back when I was like 19 years old or so.
After one year, I'd worked so hard to get in, got to the bright lights of Liverpool and just realized that university wasn't for me. And going out and drinking and partying and being a heavy metal addict was absolutely my future at that point. I just kind of collapsed under the weight of the educational system and then ended up going back to Maidstone in southeast of England, my hometown, and kind of being a bit lost and not really with anything to do, and ended up taking a call center job. I took that call center job for two weeks. It lasted two and a half years before I got something else. But I was kind of in a bit of a slump at the time. And I was in a slump because really, I kind of felt that I'd failed and I didn't really know what to do with myself. And I was kind of just scattergun applying for any old random job out there. Admin assistant here, other type of admin assistant there. Like, I didn't really have a path or a plan. And the good thing about call centers is that you have quite a lot of diversity of different types of people.
Now, let's just call out we're talking about the southeast of England here, so not that much diversity in certain senses, but there are certainly a lot of different types of people coming through that place on a regular basis and ended up buddying up with a slightly older guy who we'd kind of just hang out. We'd go to the pub every now and then after work. And he'd had a bit of a career before, but then I guess himself falling a bit on hard times. And it really helped me to just be able to kind of almost lay everything out in front of this guy and just say, look, I don't know what to do with my life. I don't know what's good in my career, I don't know what my career is going to be. And he was really like the first, I guess, mentor that I would say I never called him that at the time, but the first experience I had of having a vaguely interested but still fairly neutral and totally uninvolved in many senses, basically friends that I could deal with. Now I don't know what he's doing these days, I'm hoping he's still okay. But that was kind of my first touch point and it really started to get me thinking.
But I'm going to emphasize over a very large number of years, but if we think about then my career, I spent quite a long time working in corporate. I originally was asked as I moved into leadership positions there, if I wanted to maybe do some mentoring within the corporate structures within the company. And I was like, well yeah, sure. I'd been about a bit by that time. There are other people that were more junior than me. And I started chatting to people in fairly structured mentoring sessions to try to help them with their careers and help them thrive and all of that good stuff at work. So that was my first introduction to kind of serious mentoring in the sense that it's actually something that's sponsored by a company and ends up being a real thing.
So I did that a few times for a few people, then moved out into the world of startups. And one of the things I realized, and I realized this in the worst way possible, because what I did was I went online a couple of years ago now, went on Twitter back when that was still a good thing to do. And I basically put a thing up like a tweet that basically said, hey product managers, if anyone fancies a mentor, why not drop a call in into my calendar? Here's my link and you can book me, we'll have a chat, I'll help you with whatever's on your mind.
And I was expecting two or three handful of people maybe give me a pity booking just to make me feel better. But I got 76 bookings from January through to April, like one a day. And I was like, wow, that's a lot.
Daniel Stillman
Now there's a hunger for it.
Jason Knight
Not clearly 100% there's a hunger for it. And I think product management is a very ambiguous role at the best of times. And there's a lot of people out there that maybe feel that they're not doing it right or that they're underperforming or that their company isn't doing it right. And a lot of uncertainty about whether product management is going well or what's okay, what's not okay. All of these things that mentors can help with. So I did a bunch of those calls, helped a bunch of people, hopefully. And that then really started me down the path of saying, well, hey, maybe we should mentor more people. And eventually to the point where I'm like, well, maybe we should set up a platform to help mentor people.
Daniel Stillman
Not surprisingly, you thought to yourself, how might I productize? Well, you have a systematic approach to things, right?
Jason Knight
Well, yes, although not as such. I mean, yes, obviously it turned out to be but at the beginning, it was very much like, wow, I've just helped 76 people, give or take. That was amazing. But I never want to do it again.
Daniel Stillman
It's a lot of context switching. It's not a time of your day.
Jason Knight
It's a lot of contest, which it was only like 45 minutes or an hour out of each day. And I did it around work, like, before work or after work. It wasn't a big burden, but it's a lot. And just seeing that kind of backlog of people into the future of all these different people, none of whom you know, none of whom you have any idea.
Daniel Stillman
So I'm gonna this is a really interesting point because it's a lot, but in a way, it was also not enough, because I love this idea of an interested but neutral party. And I think some of the gold and mentoring comes from not just having one person. I love that scene of you just finally having someone to unburden your like, this is what's going on. And when we all have these nonlinear pathways in work, like, M I okay, just being seen by another person is really powerful. But I think some of the golden mentoring comes from someone knowing you over time. Is that fair to say?
Jason Knight
I think it is fair to say, and I have to call out that maybe, technically speaking, what I offered these 76 or so people wasn't really mentoring, because a lot of them were one offs.
Daniel Stillman
Well, I don't want to take that away from you. I think you can't. Now I sound like a jerk. Oh, my God, thanks for calling me out. One call can have a lot of value, like just being able to just say what's going on. But I think some of the returns accrue because Sandra, who's going to be joining us in about 15 minutes, you've been working together with her for how long now?
Jason Knight
I think I've been working with Sandra for maybe two or three months to check when we actually started out. And yeah, I think that the return there is a benefit to the return. There is a benefit from the accrual of knowledge that you have about someone's situation and also, somewhat selfishly, the satisfaction of knowing that things change over time. Like, obviously, if you're having a one off discussion with someone, you give them the best advice you can, and they go off, and maybe you keep in touch with them, maybe you don't, but there's not like, a longitudinal element to it. Whereas when you're speaking to the same person repeatedly over time, be it through coaching or mentoring, obviously different sort of sides of a similar coin, I guess.
But the idea that you can basically check in and part of that checking in can be about accountability, like, hey, did you do that? But part of that checking in could just be, well, how's it going? How has your situation changed? And I think that that's one of the most powerful things of a more longitudinal approach where you're going back time after time. I don't think it needs to last forever. I think that there's a natural lifespan for mentoring. But at the same time, I think it is important to a have that context. It's like with chat GPT. Right? Like it remembers a certain amount of stuff. If you say things in the same window, then it will remember some of those things until eventually it forgets. But it ultimately can have a kind of a coherent conversation with you based on the stuff you told it before. And it's just that. But biological with mentors, you're sitting there saying, well, I remember that you had this problem last time. How's that going for you now? And oh, did you try these things? Well, maybe we could try this other thing. So yeah, it does compound definitely for sure.
Daniel Stillman
In our previous conversation leading up to this one about mentoring, we talked about one of the challenges being from a sort of platform approach is how lopsided the marketplace seems to be. And I'm wondering what you've done to I guess specifically, it seems like there's more people who say, I'd really love to get some mentoring, versus people who say, I'm going to carve out some time regularly for a person to do this. What have you done to try and equalize or industrialize the matching process? Because it seems like that's one of the one of the one of the barriers to having this happen more often.
Jason Knight
No, 100%, and just to kind of briefly resume like what it is that the platform that I've set up does. So we've got effectively a two sided marketplace of mentors and mentees, as you kind of touched on that's. Been going since about January, very slow burn. We're kind of growing organically at the moment because there's never enough time to put all the features in you want and we want to make sure that it's right. But yes, you've got a problem. Generally speaking, and this is something I saw last year before the platform was even a twinkle in my eye, when I ran a mentoring scheme with a friend of mine based out in the US. And basically what we did was we put a Google form up, basically circulated it in all of our social channels and said, hey, anyone to be a mentor or be menteed or be mentored, sorry. And there was good feedback or good take up of that, but ultimately we then ended up having to semi automatically match these people. I wrote some terrible Python script to kind of algorithmically match people together. And I'm being very charitable when I call it an algorithm, but there was a certain decision tree that was going on to try and get people and you're right, there were far more people wanted to be mentored than there were to do the mentoring. And I think that that's natural because a mentoring is massively beneficial to a mentee, it is also beneficial to a mentor, but maybe not in as many obvious ways, whereas for a mentee it's super obvious.
And also the lower down the career ladder you are, the more likely you are to feel that you don't quite have it all sorted out yet. And maybe a more wise old bird can come and tell me some of the things as kind of discussed before. So I do think it's natural for there to be a hunger, or more of a hunger for people to be mentored than maybe to be a mentor. What we've done with my mentor path, the platform that we're putting together and continuing to develop is we've encouraged people, for starters, to be multiple mentors. So rather than just Daniel stillman signs up to be a mentor and gets one person to be his mentee, great. But actually, if Daniel stillman has space in his schedule for four or five people, or two or three, then Daniel stillman is absolutely encouraged to do that. Because an hour a month or 45 minutes a month or whatever the session length that you decide to go with is that's not too much time. And if you can handle it, we definitely encourage that.
We also do encourage mentees to reach out to multiple mentors because obviously there's a certain there's differences. Like you can get differences from different types of people, different advice, different perspectives. Maybe if you want someone that's worked in your specific industry or certain types of stages of company or something like that, it's good to potentially get various different people kind of matched up with as well.
So we do encourage kind of both sides to search for multiple or make themselves available to multiple. And as far as I can remember, I'd have to check the figures. I think we actually, technically speaking, have more mentors than mentees available at the moment because of that kind of multiple, that suggestion of multiple. So technically speaking, we probably have fewer physical mentors, but because people are generous enough of their time that they maybe take two or three people on, then technically speaking, we have availability for a lot more. Now, obviously another solution to that is just to pour more people into the top of the funnel and get more mentors and mentees. But at the moment, that seems to be working pretty well.
Daniel Stillman
That's really lovely. And I think selling the value to a mentor, what are the challenge with getting people on boarded, saying, yes, this is worth giving your time to? Is there a mental model shift that has to be invited in them?
Jason Knight
Well, I think if we think about it, there's that kind of classic vitamin versus painkiller. I've translated it into vitamin for the American audience. Vitamin versus painkiller. You can use whichever of those you prefer. But in any case, there's this whole idea, and this is something, to be honest, that affects a lot of effectively well being or workplace well being, apps, this kind of idea that I really want to care about this, but at the same time I'm busy and also it's free, or it's free for me, and therefore the commitment is a challenge. Like people easily forget to do these things.
But I think there are benefits that are easy to espouse, certainly for the mentees. Like if you're a mentee, you can find a mentor who has more experience in your industry that's prepared to spend time with you and is prepared to give you the benefits of their experience to help you and encourage you to make progress in your own career. That's a no brainer in many ways. If you can find the time and if you can find the right mentor. I think if you think for a mentor, it could be considered a little bit lopsided, that arrangement in the sense that, well, I'm giving my time away for free probably to someone. Now I can do that because I feel good about that or because I want to pay it forward or because maybe even selfishly, I just want to feel good about myself that I'm helping someone. Like, these are all reasons that people could do mentoring.
But I think that there's also another thing that I don't know if you remember the film Interview of the Vampire or the book obviously as well, but the story of Interview of the Vampire where basically there's this concept that vampires have to kind of somehow stay in touch with the youth or with the zeitgeist to stop fading away. Like they need to continuously update themselves or they turn into fossils.
Now, it's not quite that dramatic. It's not quite that dramatic, obviously, but this idea that there's this kind of concept of reverse mentoring as well, where maybe a mentor, maybe a bit older, bit further in their career, maybe a little bit out of touch. With the day to day concerns of the average worker maybe gets a little bit back as well from mentoring people that are up and coming and sharing experiences and hearing about the problems that people in today's workplace that 1020 years behind them. I think that's incredibly valuable as well. But again, there is generally a there's there's a certain fluffiness to mentoring as well though, which is something that needs to be discussed, this idea that there's not like a concrete output of it often, sometimes there is. If you're sitting there saying, hey, I want to be mentored so that I can get better at public speaking or something like that and I need someone that's done that to help me or whatever, okay, cool. Like maybe if you then go and do a talk or something like that that you don't think you could have done before, maybe that's an outcome, maybe that's a concrete output. But a lot of the time it's more just a sense that things are better than they were before. But how do you measure that? And how do you attribute that to just mentoring versus all the other things that you're doing to develop your career?
So there isn't certain fuzziness around mentoring, but it doesn't mean that mentoring hasn't helped. I absolutely believe that it does. It's just part of the system. But when you're sitting there saying, well, I need to either do this thing that I really need to do or have that mentoring chat, it can be a barrier. I do think that we need to make sure that we enable people as best as we can to have those discussions, even if they have to postpone them, but to at least see that there is value in the concept of reaching out empathizing with people and just sharing experiences and hearing from people that maybe you haven't heard from before or hearing perspectives that you haven't heard from before and using those to develop yourself as well.
Daniel Stillman
It's a human output. It's human input. It's a human conversation. And what's the value of talking to a friend? So we only have a few more minutes before Sandra comes in. If we were to only answer one more question about mentoring, what should we dive a little more deeply into? What layers should we peel?
Jason Knight
That is a very interesting question. I mean, I guess one thing that people often ask about or maybe are unsure about is the difference between coaching and mentoring and where you'd use both of those things. And I think it's an interesting question because coaching and mentoring, obviously you're a coach, I'm a coach. They do share some characteristics.
Nice human discussions, possibly about goals, regular cadence, build up over time. So you've got that context and the kind of attention window from the past and stuff as well. So I do think that there are similarities, but there are also big differences. And I think a lot of the time when you see people talking about coaching online, they're really talking about mentoring. Because what they're effectively doing is saying that you need to have some person who's super credible in a certain space, like a person or a conversation designer or whatever that type of person is hypothetically. And hypothetically, whoever would have that kind of job, but then they're sort of sitting there saying, well, this person's got to come in and kind of share their experience and guide and train and all of these things.
Now, don't get me wrong, there's nothing wrong with guiding and training people, but it's not really coaching in the classic sense of the word. Like, coaching is all about actually using coaching skills to have great conversations and use all of the coaching techniques to reflect those back. And arguably, you don't even need to really be a conversation designer or a product manager to coach conversation designer or a product manager. I think that's an important distinction, whereas I think you'd find it very hard to be a credible mentor if you didn't have experience in the job or the industry or whatever that the person is being mentored in. And I think that's a big difference.
Coaching is a craft. You can think that that would be the thing, that the sort of thing that a coach would say. Sure you can think that, but coaching is a craft. It's a certain very specific set of skills in kind of Liam Neeson terms that gets you to an outcome in a certain way. And of course, there is always a chance for coaching to kind of blend into mentoring as well. I kind of call it centering. It's like the idea that you can kind of take different approaches, like the more directive approach of mentoring versus the less directive approach of coaching and do whatever you can to effectively get someone towards that goal.
Daniel Stillman
So it's like a little bit of a coach and a little bit of mentoring. Not centering with a man and a horse. Centering.
Jason Knight
Well, the original Mentor was actually a mythical character from Greek mythology.
Daniel Stillman
He was! his name was Mentor.
Jason Knight
Mentor was the tutor of Odysseus's son Telemachus. That's where the word originally came from.
Daniel Stillman
That is so true. That is amazing. So in a way, it's interesting because I think this is a very fine line of like, a mentor has to have some. We need to feel like they get us. And yet there's no way that you can have had the exact same experiences. And the industry may have changed a great deal in the intervening decades or whatever. And so there is a line between, well, I don't have the answer. So where is the switch between mentoring and coaching and how do you know when to grab for it?
Jason Knight
I think one of the most important things is if you don't have the answer, if you just don't know, then just call that out and be honest about that. Obviously it's great for a mentor to have effectively the answer to everything or an opinion on everything. But if you literally don't know, I think it's important to call that out and then maybe just explore it together. Now that exploring could be, well, you both go away and look it up and try and form an opinion on it. Maybe you go and ask Chat GPT or maybe between you, you just realize that we've got no skin in this game and I can't make a difference in this area. In which case, again, I think that one of the most important things about a mentoring relationship is that it's based on trust and openness and transparency and adds with coaching as well, obviously. But you should not be in a situation where you're basically lying to your mentee to make them think that you're clever. That's not a good outcome if you don't know the answer or if you're in a situation, as can happen, where the mentee is starting to require some other type of intervention, like maybe they actually need counseling. Maybe they need urgent support or something like that, realizing that as a mentor, you're not necessarily equipped to handle all of these situations and that it's your job in that case to get them to the right help as soon as possible, rather than somehow trying to work something out and potentially making it worse.
Daniel Stillman
We are not therapists. And to recognize 100% one of my past guests, Alyssa Rumsey, who's a registered dietitian and helps people with profound food traumas. There's still a line. We were just talking about it this weekend. Which is why it's top of mind of having a client who really should be in therapy and separate from the food coaching. And so if somebody's just literally in distress, right, some of that can be alleviated by just somebody who's been there before saying, yeah, it's going to be okay, and here's some things you can do. But some of that may need real support, real counseling support. So I think it's really important for us, to all of us to know our limits, which is really good.
Jason Knight
We need to stay in our lanes as best we can. That doesn't mean that we shouldn't experiment and push the limits of our shared understanding and all of those good things like we learn together. But we 100% need to stay in our lanes and realize when basically any intervention that we try to do could end up making things worse and that there are professionals that do these sorts of things for a reason.
Daniel Stillman
Well, speaking of staying in our lanes, I'm going to let defender.
Jason Knight
All right.
Daniel Stillman
Right on time, I believe. Sandra. Welcome to the Conversation factory. I'm so glad you decided to join us. I appreciate it.
Sandra Monteiro
Thank you so much for having me.
Daniel Stillman
Yeah. So I'm really curious if you can share a little bit of your own experience with deciding. Sometimes I think about jobs to be done with people in their lives, like the moment when we decide we need the thing and then the search to go and find it. I'm curious when you decided, you know what, I really need a mentor, and then how you found your way to Jason and working with him.
Sandra Monteiro
Yeah, well, it's a bit awkward, actually. I saw Jason until it took me as a mentee, basically. So when I first wanted to transition from I was a salesperson from sales to product management, I was looking for a mentor. And I wanted I i knew I needed someone that would help me, you know, do this transition, give me advice, how to do this, what should I do? And so basically, this was a few years ago, and I was looking online, how do I find a mentor? What is a mentor, basically? How can they help me? And I remember there were a few platforms at the time, but they were very exclusive. So you can join our platform if you have X amount of years of experience in product management, because we have very few mentors and this is very exclusive and it's not for everyone. So obviously I didn't make it into any platform, so I had to go through things without a mentor. And when I found my first job, I took my manager at the time as my mentor because she was this amazing person, super experienced. She knew everything about product management. So I took her as a mentor. It doesn't mean that she took me as a mentee.
Daniel Stillman
Can you say a little bit more about that? Because I've heard other people say this in the past of just treating someone as a mentor. It may not even be an official relationship. What does it mean to sort of just treat someone as a mentor in that moment?
Sandra Monteiro
I guess that my thing with her was that because she was so knowledgeable about everything and she was very kind with her time as well. So whenever I had a question, she was always there to answer it, and she was always there to help me whenever I came across any challenge that I didn't know how to work around. And I really deeply trusted her and I respected her. And I think that is the basis of any good relationship, is trust and respect between both. And when she left the company, I made sure that I kept that relationship going, even though she was not my manager. But she's still knowledgeable and she's still an amazing person and very experienced. So I think it stays the same way. I think I still look at her as my mentor, but she might not look at me as my mentee, as her mentee. So, yeah, I think that was one of the things. It's just trust and respect and being kind with the time as well. It's not like, come on, come on, we need to do this quickly. Let's set things up.
Daniel Stillman
I love this idea of informal versus formal mentorship. I'm really curious how you decided to how does one stalk Jason? What are the steps to stalking a mentor? Because this is clearly a nontraditional path to mentor acquisition. I think what you're saying is actually what many people do you're like? It's a wooing process sometimes, yes.
Sandra Monteiro
I don't know if that's what Jason would call it or just scary, but basically I was already listening to his podcast before transitioning into PM, and I really like the way that he, you know, the way that he interviews people, what he uncovers within these interviews and how he connects with people, how he's funny. I love that we have this kind of saying silly things and having fun with it. And I saw that he was invited to be a speaker at an event in London, so I made sure that I was at that event. And once I was there, I was just with my glass of wine, just trying to be cool and relaxed while being super nervous all about it. And I just went up to him and I said, Hi, I'm a fan.
Sandra Monteiro
And that was basically it. And I was following him on Twitter, on Link, LinkedIn. So again, stalking him, basically. And once I saw that my mentor path platform was on, I made sure that I was on that platform, and I was tweaking my profile, what can I do to make sure that I am matched up with him? But they have so many mentors available that I was being with a lot of people, and I assumed, okay, so he probably has a lot of mentees, so that's why I'm not being matched up with him. Again, LinkedIn. Chad, hi. Can I be your mentee? Do you mind being my mentor? And I said, fine, let's do it. And that was.
Daniel Stillman
It.
Sandra Monteiro
So stalking sometimes, persistence. Yes.
Jason Knight
I think I've realized why we're 100% matched on the platform now as well. I just thought that was a coincidence. But I think it turns out that you basically chose all the different settings until you were 100% matched. Makes a lot of sense.
Daniel Stillman
It's really brilliant. So, Sandra, what makes a good mentor in your mind, in your perspective? Because you've had a few now, what would you say are the qualities of a great mentor?
Sandra Monteiro
Yes. So this is my first official, proper mentor mentee relationship that has a structure. First of all, again, trust and respect. He is someone that I respected already. I knew something about his career and the way that he approached things and how he talked to people. And then as soon as we started this relationship and making it more formal, I also saw that I could trust him so I can be honest and open with him, and I know that he will be honest and open with me as well. Another thing that it's very important for me is the fact that he is unbiased. So he doesn't know my company, he doesn't know the people I work with. He doesn't know my overall context of things. So he's very unbiased. And especially when he's talking to me about things, I might be a little bit worked up when I have some kind of challenge, and I might be a bit more emotional. And he's very objective and clear and dispassionate about things. And I think that is extremely important because it also creates some perspective on my side, as in, it's just a job, let's be cool, be calm. We can work things through. Another thing that is really that I find really interesting is that he doesn't tell me how to solve my problems, or he doesn't give me the solutions. He gives me the tools so that I can find my own solutions and work my way through my own issues. So he always gives me examples of things that he went through in the past, in his previous jobs situations that are similar to the ones that I'm going through. And that not only, again, gives me perspective on things, but it also makes me realize this is not a me problem, it's not a me thing. This is something that happens with other people as well. So I'm not at fault here. It's just growing pains. And the way that we need to do that, we need to go about our jobs and life overall. And the other thing, apart from his own examples, is there is always material. So here's this book, just read through this, here's this Twitter thread. It's very interesting. Or check out this video because it also has some information around that. So I think that
Sandra Monteiro
the breadth of knowledge that he has and how quickly he is able to access that knowledge and share it with I find it really good and really helpful because it's at the time, it's not something that he will say, let me look through things, and eventually I will send you something that will help you. It's just I have this resources available that you can look through and I think that's amazing. I think that's really helpful.
Daniel Stillman
It's really interesting. There's three things that I've heard so far. One is the difference between and the possibility of informal versus formal mentorship and how both can have a lot of value. The story that Jason told before you came on of his first sort of informal mentor, where it's just someone you feel comfortable telling things to. The second sort of interesting tension you pointed out is the difference between somebody who is in your organization versus someone who is outside of your organization. And Jason hooked me up with his friend Talia, who predominantly builds internal mentorship programs. And it seems like, Sundry, you've had experience with internal versus external mentorship. I think there's a lot of value in having somebody who's internal because they know everything and there's a lot of value in having somebody who's outside of the organization and that they are unbiased and you can tell them more things without, I would think, any risk whatsoever.
Sandra Monteiro
Yeah, exactly.
Daniel Stillman
So in your estimation, is it a both and or is it an either or? If you had your druthers, I mean, obviously if you Jason's, you're forever a mentor, he's your ideal, but you've had internal versus external. If somebody else who's listening to this is thinking about either finding a mentor or being a mentor, which direction do you think they should direct their attention for maximum value?
Sandra Monteiro
I don't think it's an either or. I think it's perfectly fine to have both. And it can work to your advantage as well. Because, again, my previous mentor, she was my manager, so she knew exactly
Sandra Monteiro
I would be going to her for things that weren't directly related to what I was doing at that point and how to approach this problem or how to approach that specific stakeholder, or how to deal with this situation within the company, someone from outside the company. It gives you more of a holistic kind of approach. As in this situation, I would do this and this and that. So that is also something that I can take not just for my day to day job, but also if tomorrow I go to a different job, I can still take those with me because they're much more holistic and they are applicable to other situations. So I think that ideally have both. Why not?
Daniel Stillman
There's another point you made, and it goes to a question that Jason and I were trying to pick at, which is the line between coaching and mentorship and solving versus giving tools, examples, materials. Emotional distance, I think is another tool context in the industry. And yet we do want someone who's sort of been there, who knows, who's been along the path we've been before. So I don't know what my question is here. You are not going to get a solution from Jason. So what is my question then? How do you manage that for yourself? Because I think there is often in a mentee relationship, there's a desire for answers because you're coming with a pain, a problem, frustrations with a process. How do you manage that for yourself, your own expectations?
Sandra Monteiro
Yeah, so that was something that that's how I thought it would be. I thought that I would come up with a situation, a problem, and that he would give me the answer and I would be, hey, so this is the answer. I'm the best. And that never happened. Never. And from the first session that we chatted, he was always, there are these tools, there are this book, there are all these resources that you can look into, where you can find your answers. And there's also my experience, and I was in a similar situation in the past and this is what I did. But also the fact that I have to explain everything to him in the sense he doesn't know, he doesn't have the context. It forces me to bring my thoughts outside and speaking them out loud. So I have to rationalize things. I have to try to get some distance from it as well. And that also helps me create my own solution. So it was very organic. It was not something it said, I will not give you the solutions you need to find them. It was just the way that we built this relationship is the talking, the going through all the steps that I've been through, how I approach them, how he approached them and me seeing the difference between my approach and his approach and just trying to find out that middle term, like, the best for me in my specific to approach the problem again. So I think that was one of the things that I appreciate the most in this.
Daniel Stillman
It's really interesting. Oh, sorry. Go ahead.
Sandra Monteiro
Yeah, it's just I'm not telling you what to do. I'm helping you figuring out what you need to do.
Jason Knight
Yeah.
Daniel Stillman
So one thing I'm hearing, if you were to write a manual for mentees, somebody's thinking about finding a mentor, it sounds like one of your pieces of advice is come with a really specific problem, but also expect to be open about how it gets resolved because it's your job to find a solution.
Sandra Monteiro
Yeah, that is one of the learnings. Again, I know I've said it before, but I thought that he would solve my problem.
Jason Knight
I don't have any solutions. I don't really know anything. But I do think one of the most interesting aspects of and again, talking earlier about mentoring and coaching, which both share similarities and they also have differences, but I think that the sense of empowerment is the most important thing. Like, Sandra is not my puppet, that I can just kind of do the strings and just get her to do whatever I think is the right thing to do. And kind of almost like a father looking at his kids through trying to get them to play football because he can never do it or whatever. That's not the point. I very much see my role and the role of all mentors. That role is really to empower people to make the right decisions in their context and to make the right moves based on a combination, for sure, of experience. As Sandra said, this is what happened to me when I tried to do that. Maybe don't put your hand in that hole, and that sort of thing. But also then there's also some other stuff to back up. Here's some books that people who also got bitten when they put their hand in that hole, and maybe you should read those as well and just try and then inspire people to some extent to take action themselves. I think that's really where the sweet spot is, rather than just sitting there saying, right, Sandra, here's nine things that you have to do. Tell me next week if you've done them. Otherwise you've failed. That's not the goal.
Daniel Stillman
So what haven't we talked about that we should talk about? What's an important aspect of mentoring menteeing relationships and doing this dance between solving and asking, what haven't we talked about that's important to talk about? I'd be open for either of you to offer something.
Jason Knight
Trying to think. Feel free to step in. Sergeant, if you're looking for me to empower you.
Sandra Monteiro
I just want to reiterate that I think that the key to any relationship, any good relationship, is being open and trust, because you need to be able to trust each other if you're going to make this relationship work in the long run. And you need to be honest as well. It makes no sense for me to be talking to Jason and saying, so I've achieved this and I've done that. When it's a lie, it doesn't help me and it doesn't help anyone, basically. So being just honest, I think honesty is very much the key. And also being open to feedback. There was this session that we we had a couple of weeks ago when I was very keen and working and I want to do this and I want to do that, and he just asked me why, and I was like, I don't know. Well, then maybe you should find out the why. And I said, great feedback. Yes, maybe that's something that I really need to work on. So also being open to the feedback and not just taking just thinking that everything is just very nice and perfect, you need to receive the feedback as well for things that you might need to improve and also give the feedback. If something is not working between us, I need to be able to tell him this doesn't work. This is not being helpful in any way so that we can work on that and improve the relationship.
Daniel Stillman
This is a really valuable point, Sandra, because this idea of like, oh, it's just going to be all these endless stream of amazing tools and solve problems with wonderful perspective. And sometimes the reality is you're going to hear something that maybe you don't want to hear or you're going to be asked a question that you don't feel comfortable answering yet and walking into the conversation with that expectation. Jason, do you want to say, it sounds like you were nodding your head? You remember that moment?
Jason Knight
It sounds like, yeah, I do. But I think also there's an even more important point I was thinking about as Sandra was talking, is this idea that whilst there is a certain, I guess Imbalance in a mentoring relationship, in the sense that obviously I'm the one giving, for the most part, the, let's say, advice or the places to look, that it's still very much kind of a relationship of equals. Right. Like, I'm not sitting here as Sandra's boss or her better or anything like that. That's not what mentoring is. Mentoring is all about kind of co creating the future that you want to have whilst obviously accepting that one of the people has in that partnership is more experience in a certain area, which means that they naturally have more to bring to certain parts of the conversation. But it's still very much a conversation between two equals that are trying to get to some kind of goal, which is ultimately one person's goal. Like, Sandra has goals. Those goals are not ultimately my goals. If Sandra decides that she's had enough of me, then she will continue towards those goals and I will not. So it's not up to me to live those goals. It's up to me to do my best in the time that we have together to help her towards those goals and try to inspire action in certain areas and point me in the right direction and give the benefit of any experience that I do have. But again, it's not that I'm either the puppet master or the boss or the superior or anything like that. This is a relationship between two equals where just one person has more context and the other person has maybe more breadth.
Daniel Stillman
Anything you want to add to that, Sandra?
Sandra Monteiro
No, I agree with him. It may come a time where I'm just, hey, Jason, this is not working anymore. Let's stop this. It may not happen either.
Daniel Stillman
Well, in my coaching training, one of the things that I try to hold in the space is this is one relationship where you should never have to guess where you stand, and that openness to feedback that you pointed out. Sandra is something that there is some asymmetry, I think, both in the coaching and also in the mentoring relationship. But the symmetry is that we're both choosing to be here. We can both leave at any time, but we're also responsible for communicating what's going on with ourselves. Right. I think one of the things that people are so ghosting is something that happens on online dating, and it's awful to be ghosted by someone. It's terrible. It feels terrible. And this is a relationship where you don't ghost. You say, hey, this is what I'm not getting, or this is what I'd like to get more of, ideally before you get to this is what I'm not getting. So I think that the symmetry is in the expectation of feedback and open communicativeness of needs and wants and goals. So I think that's really the asymmetry isn't that Jason's problems in the conversation are less important than Saunders problems.
Jason Knight
Right. My problems are generally less important than most people's problems. So we should just accept that.
Daniel Stillman
We just have a couple of moments left. Anything else that we haven't talked about that we should talk about, sandra around what makes a great mentor mentee relationship or how to think about it, especially from the mentees side.
Sandra Monteiro
I don't know what you've covered before, but I think that it's just that it's important for people, when they're looking for a mentor, to be clear on what they are looking for, but also to be patient, because you don't necessarily find the mentor at your first. That might just not be the person that you are looking for for whatever reason. Maybe there's just no chemistry, or maybe it's just the experience that is different, or maybe it's just a personality issue, maybe a million things. Just be patient. And if it doesn't work, it doesn't work. You just need to do what's best for you in relationship and just try and find someone else that might be better for you. And if you're on the side that you're being refused, just don't take it personally. It needs to work for both sides regardless. So I think that is important. If it's not working for you, then it makes no sense to invest the time on it, and it might be better for both parts to just start over.
Jason Knight
Yeah, I had some feedback recently from a couple of people that used the platform that were like, I really don't like that button that says end relationship, because it just sounds a little bit too harsh. And I'm like, well, okay, maybe we can come up with some fuzzier words. But at the same time, Sandra's point is really valid. Like, sometimes even the most matched on paper, two people that have maybe they've worked in all of the same types of companies, they've basically got very similar career paths. They're from the same part of the world. Like, all of these different things, they could look like brilliant mentor mentee relationships on paper. But actually, you look at it and you're like, well, actually, we had a chat. We just didn't like each other. We didn't click, we didn't get on. We couldn't find enough common ground for this to be a productive relationship. And we could kind of just tell. Now you've got two options there. You can either try and soldier on, because, like black mirror, we've been matched together and somehow that's now our future, or you can sit there and say, well, okay, fine, let's move on. As Sandra says, no harm, no foul. It didn't work out. There's plenty more fish in the sea from both sides. You can go and find another mentor. You can go and find another mentee, find someone that's going to help you, and don't be afraid to. I mean, look, you should always give people a chance. Like, if you're halfway through a mentoring relationship, like, maybe you're sitting there three or four sessions in and you're like, oh, well, that last call didn't go very well, then maybe there's something that can be corrected. But if you're just sitting there up front and saying, I just don't think this person gets me, or I don't think there's enough commonwealth, just move on. I think it's important not to get too hung up and feel like you're hurting people's feelings. Sometimes it just doesn't work out. Yeah.
Daniel Stillman
And Jason, if you could place a billboard on the A one to encourage more people to like to to jump into the pool and to start mentoring more, what would you what would you want to put on that billboard? To to get people.
Jason Knight
To be a.
Daniel Stillman
Mentor to be a mentor, to start to start doing it more? Yeah.
Jason Knight
You'Ve probably had a lot of support in your career, or maybe you haven't and you wish you had, but in either case, take a leaf out of the book of the person that you wish you could have been and start to pay it forward to the next generation. 100%. Sure. That scans I kind of made it up as I went.
Daniel Stillman
No, that's really on those lines.
Jason Knight
This idea of being I've literally never said that before.
Daniel Stillman
No. The idea of being the person you wanted to have had, even if we didn't have that person and there's a lot of people who feel like I've just bootstrapped myself. There's a possibility of paying it forward 100%. That's really beautiful. We are at time. I'm really grateful that both of you made time for this conversation. I think the mentor mentee relationship is a really special, very powerful conversation patient that's worth doing well. So I'm really glad you both came on to talk about it.
Jason Knight
Thank you very much for having us. And I'm going to go get that restraining order now for Sandra as well.
Sandra Monteiro
Thank you so much.
Daniel Stillman
All right.
Jason Knight
Thank you, Sandra. Thank you so much.
Daniel Stillman
Jason. Be well.
Jason Knight
Thank you. All right.
Sandra Monteiro
Thanks.