How to Choose the Right Coach as a Founder

Jeevs Mahil decides which coaches get put in front of Octopus Ventures' portfolio founders, and after years of those introductions she has a clear, slightly uncomfortable view on why so many founders pick the wrong one.

James and Jeevs get into why "ex-founder" tells you almost nothing useful about whether someone can actually coach you, the one question to ask before your first session that most founders skip entirely, and the real ROI behind getting this call right versus wrong. Get this one wrong and it costs a lot more than the coaching fee.

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Transcript

SPEAKER_01 0:04

Hi, I'm James Johnson, founder and CEO coach. Welcome to Peer Reflex, the podcast where your peers will tell you what's unlocking their 10 million plus business. In today's episode, Jeeves and I explore how to choose the right coach for you. Remember to hit the subscribe button before we get started. And now on with the show. So, Jeeves, welcome to the show.

SPEAKER_00 0:26

Thanks, James. Great to be here.

SPEAKER_01 0:29

So, I mean, this is this is you deal with founders all the time in your role of VC. Like what first of all, before we dive into what we're going to talk about today, what got you to this point? What's your origin story?

SPEAKER_00 0:42

Um, so yeah, I have the privilege of working with founders all day, every day in my current role. So I'm currently um working the people in talent uh platform role at Octopus Ventures, uh, whereby I support primarily our B2B software and AI businesses, all the way from kind of C stage up to Series B, Series C, so wide range, and kind of supporting the founders along that journey on all things people and talent related. So, what we found the biggest value add there is making sure they get the right people in the right roles, get the right roles scoped out first, and then get the right people in at those kind of leadership levels. And a lot of the work is also around supporting our leaders and our founders to be the best leaders that they can be. And that may look different at Steve stage to obviously kind of later stage, kind of being there along every step of the way and getting them ready for the next fundraise is kind of uh how we look at it. Um uh previously, prior to this role, uh, I've always been in an operator uh position. So I was at a B2B payments um unicorn company, kind of from pre-Series A, uh looking after the talent acquisition there. And had a bit of a dabble with Founder Life myself prior to that, uh starting up a recruitment company, not VC back.

SPEAKER_01 1:59

But if that must give you quite a super at least an appreciation of what founders are going through.

SPEAKER_00 2:04

Yes, from a at a very kind of grassroots level, absolutely. There's so many kind of different pressures and expectations that come, obviously, once you've got VC backing. But I feel like actually having been on the other side, actually, probably more from my operator role within this kind of scale-up that I just mentioned, um, kind of seeing pre pre-invest pre-kind of outside funding to post-outside funding, how that changes the dynamics internally and the pressures that can put on the leadership teams as well. So here to support them on all of those kind of things while still working kind of through the lens of the VC as well at the same time.

SPEAKER_01 2:38

Do you find it's kind of you you guys reaching out proactively on the leadership side, or do you find a lot of the founders are coming to you going, what can I, what can I do?

SPEAKER_00 2:47

Yeah, so I mean, you know, you get kind of a range here because you've got some founders who have been there, done that, founded a successful company in the past, or not successful, but got the war wounds and all the lessons, and then you have really, really fresh green founders. I think something that, you know, a lot of founders realize right from the beginning is the value. They've probably done this through hiring someone really great or getting a co-founder on and all of the things that that can unlock and the time that that can save them. I think when we're doing our due diligence kind of pre-investment, I do try to spend time with the founders, at least one of them, if there are multiple, to see the kind of questions that are coming up and ask them what are your top top of mind kind of queries at the moment or things that you're trying to solve in terms of people and talent, and you can get a gauge on how they're thinking about it. I think quite rightly, a lot of the time founders are just heads down trying to get stuff done. And so a lot of the people and talent and leadership things can feel kind of on the scale important but not urgent until they are, and you're in crisis mode. So I think that's where we can be more proactive and say, hey, we've worked with other companies at this stage. The pattern is that normally this starts to crumble at this stage. Let's help you get ahead of that. Um, and that's not, you know, I wouldn't expect founders to always kind of have that in mind when they're trying to do a million other things on the ground that are urgent today. Um, but you'd be surprised. I think even kind of very early stage, kind of fresh founders do really understand the value often of the people around them. I think that there are some some kind of patterns that we see more recently. I've kind of started noticing of, for example, you know, hiring people who kind of have a have done this before and and and can kind of come in and like not need too much training and not need too much handholding and things like that, as opposed to bringing people in just kind of for a good attitude and they'll just get it done. Because a lot of the times founders obviously probably built their business with like bringing friends in or bringing family members in, and everyone kind of mucks in, and actually, how do you kind of professionalize from that? Um, is one of the things that we really kind of proactively try to look at as well.

SPEAKER_01 4:54

You're clearly more persuasive than me. I I find that founders most of the times I work with are kind of six months into the whatever pain they're looking to solve, and you go, I wish I'd done this six months ago, but if you talk to exactly the same person six months ago, they go, I haven't really experienced the pain enough here to truly appreciate the help that I need.

SPEAKER_00 5:11

100%. And I think another thing is also by the time a founder comes to me, and like if we're talking about coaching, says to me, I think I need a coach, I'm kind of like, oh, sir, like alarm bells, because they're probably already passed, you know, it's probably because it's such a pain already. I think quite rightly again, you know, they they have limited time and limited resources. Having a coach or bringing that kind of um that that kind of support in, same as kind of reaching out to me and asking me for kind of like nice to have support, just doesn't even register because they're trying to do all the urgent stuff and fight all the fires right now. Um, so that's probably why, James, by the time they get to you, you know, they should have actually started working on it six months before. But you know, it's always kind of in hindsight, it's 2020, isn't it?

SPEAKER_01 5:54

Yeah, sort of I I don't have time for it right now. It's both like the biggest signal that it should they need a coach right now and and often the reason why they don't choose to do it at that moment.

SPEAKER_00 6:06

Exactly that. Yeah.

SPEAKER_01 6:08

So so we're gonna talk then a bit about like how you choose a coach. Because I think this is a question that comes up for you quite a lot, is that right?

SPEAKER_00 6:15

Yes, that is right. Yeah.

SPEAKER_01 6:18

So how is that something that you're sort of portfolio asked? Or is that something that you sort of you're thinking about yourself?

SPEAKER_00 6:24

So um, as kind of we're we're very big on kind of encouraging founders to get coaches at Octopus. Um, it's something I'm very proud of, actually, and you know, the whole team kind of rallied around that. Um we did actually even have it as part of our term sheet. I think I mentioned this to you before. So it's not an every single term sheet, it kind of depends on on the deal. But we had stipulated that once you kind of receive funding from ourselves, you know, you've got the capital then. But actually, almost an insurance policy for us is let's make sure you've got the support to not burn through that cash straight away and to have the support, you know, outside independent, outside of your board, outside of your um people in talent person, you know, someone who is just for you as a founder. So stipulated a percentage or a small, you know, very kind of nominal amounts of the investment that would be um should be invested in coaching in the first six months of being in the portfolio. Um so we kind of start the conversation about have you got a coach right near right from the beginning, kind of proactively from our side, but then it is very much from the founders like how would I even know who the right person is? Like anyone can call themselves a coach these days, you know, it's so unregulated, da-da-da. Totally fair points. So, one kind of rule of thumb, and I think you know, this is pretty standard, is that I would always say speak to kind of three coaches and get a feel for it. Because if you've never worked with a coach before, or even if you have previously, but now your needs have changed and the kind of support you want has changed, speak to as many as you can and have that kind of first intro chemistry call. But I think you know, founders might just like jump on and have a 20-minute call and then be like, yeah, they seem nice. So actually, I try and prep them of like, what are you actually trying to work on? Like, what is the support you need? Because I think if you're trying to become a better CEO, say, or if you've got a very specific founder conflict that you want to work through, you might want a different type of coach. So, what is exactly the support you need is something that I'd always prep them on to be thinking about. And then when you come off the call, how do you feel? Not just like, did you like them and did they feel comfortable, but did they like look challenge or assumptions on that call? Did they talk to you, you know, did they make you think a bit differently? I think coaches, the best coaches that I've ever worked with, they don't provide certainty, but they kind of provide you have some clarity in the in the moments and in the hours and days following the session, right? There's actually like really reflecting on that. I don't think you can choose straight after the call. You need to see kind of what it's got kind of going inside your own mind.

SPEAKER_01 9:00

Sounds like the benefits of it feel like it's it it can write. Sounds like it depends on the problem you're trying to solve, is almost step one.

SPEAKER_00 9:09

Yeah, exactly. Exactly that. And I think like so often, this happens a lot. A founder will come to me and say, Oh, geez, do you have anyone in your network who I could speak to? So I'll say, Yeah, let's talk about like what are you looking for support on? And actually, what they're describing is they needed a mentor or they need an advisor. So I'm thinking about how to structure my series A. Okay, cool. Like actually, we've got loads of people, I've got loads of people in my network who have done that, but they're advisors or their mentors. Um, that's not specifically a coach. Whereas if they're coming to me for something like, I just really want to get out of my own way, I need to become a better leader, or we've had loads of attrition recently, and the feedback has been that my management style isn't, you know, isn't working for the team, or I'm rubbing people up the wrong way, then perhaps I would introduce you to a coach. And I think that's one of the biggest education pieces. Um, a lot of the time. And sometimes I only realize it once I've come off the call and I go out to my network to be like, oh, this is what they're looking for. And I'm like, they're describing a they're describing an advisor there because of the kind of profiles that are coming to my mind and not a coach, um, it is more of a mentor and an advisor. I think, and we've spoken about this obviously previously, but there is education to be done on what exactly a coach can provide as opposed to an advisor and a mentor. And if we're trying to find all of those things wrapped up in one green unicorn person, then potentially they're not going to be the best at all of those things. And actually, what I really encourage founders to do is like elite athletes, is have a bench of support. And on that bench, should absolutely be a coach. Doesn't mean it needs to be the same coach throughout your whole journey. Probably not, you know, probably a coach for different times and you know, we all change, we're all evolving. But with that coach, make sure it's someone that you don't just feel comfortable with. They're supportive, but not necessarily comfortable, right? They're gonna help you grow to be the best that you can be. But on that bench, also absolutely have advisors for different things that you need to do. So if it's gonna be another fundraise and you need an advisor for that, get that person, and they can advise you on what they would do, right? And then maybe you need a mentor for something as well. I think something that like what I always kind of come back to, and what I've been saying to our founders is I think mentors and advisors can give you their map, but the job of a coach is to help you read the train and build your own map.

SPEAKER_01 11:26

So it's okay.

SPEAKER_00 11:28

And that is the distinction. Um, and you need that both of those things are valuable. And I think a lot of our founders, and I'm not kind of boo-booing this because I think there is value in this, and a lot of the coaches I do introduce just happen to be ex-founders themselves. But a lot of our founders really over-index on picking coaches that have successfully exited a business or have successfully grown a business to kind of 20 million upwards ARR because that's our next stage, and that's what I need, and that builds like instant credibility with our founders. And they think you've walked in my shoes, you get it, you have a shared like lived experience. But actually, there's so much, and I'm sure we'll delve into this a little bit more in the chat, but you know, there's so much around that, which is like absolutely that coach can then sometimes put on their mentor hat or their advisory hat and say, This is what works for me, but at the risk of it becoming a bit of a disservice because no two people are the same with it, and no two people have the same limitations, no business is the same, no market is the same, right? Even if it is in the same market, it's a different time. Um, so just really kind of being cognizant of that and trying to trying to guide founders to understand actually maybe someone hasn't been a founder in exactly your shoes, but they might be an exceptional coach, and that's actually going to be the unlockable.

SPEAKER_01 12:50

Yeah, so the example that came to mind is kind of like ex-professional footballers. I mean, there's not there's historically an over-indexing on like, oh, they've been a great player, be a great manager, and I think there's plenty of examples where that's doesn't hold. I mean, doesn't mean there aren't some great managers who were great players, yeah. But like there are a lot of man great managers who were not great players. Yeah, for example. Yeah, yeah. Um, and I think I think I definitely think having that experience can help, as you say. Like if you've been in the environment, you understand shorthand, and you can there's some empathy or just questions you don't need to ask, but potentially you're too much, you're too close to it. Yeah. And I think just yeah, what what what is the role that you need? What is the support that you need?

SPEAKER_00 13:38

Exactly. And getting really, really clear on that, and that will change as well, obviously, right? So, you know, then perhaps that coach won't be the right person, but I think being really, really clear of that at the beginning, and a good coach will know you know, will communicate, should communicate whether they can help you or not. You know, they might not be the right person to help you at that certain stage, or if it is something very tactical, such as I don't know, I keep using this example, but I don't know how to structure my series A, or I don't know how to do X, or I want support on this, they should be able to signpost you to, I'm not the right person to support you with this, but you know, I've got these great mentors or advisors or anything. So I think as long as again, it's like I think also, and this kind of goes throughout the whole coaching journey, the founder can't just expect you to turn up, the coach fixes them, and then they leave the session. Like it's got to be very much driven by the founder, and that starts right from the first chemistry call for being really clear about what they want, and then kind of figuring out with the fat coach whether they're the right fit.

SPEAKER_01 14:37

I think there's definitely a danger of people coming, like, oh you hear the chat, like, oh, I'm good at coach, it's really good. Well, therefore, I'm successful. I need a coach to be successful. Like, all successful families have a coach, therefore I need a coach. I had one guy came to me and was like, Well, I was at this event, I I met someone that knows you, and I don't I don't really think I need a coach, but he he was like, I thought we could try it. And actually, what he was looking for, we had one session, it was like he'd actually look more for a consultant. It was more like, what's the solution? Well, I said, Okay, well, here's the solution. It's like, oh great, that's that's what I needed. Yeah, that's not really that's not really coaching, you just just learnt on my business experience. Yeah, or why like my coach, I had two coaches for quite a long time. One was I had the same coach for six years, and he came from HSBC in the sales background, no founder experience, but like super smart. I trusted him, he asked good questions, he would challenge me. That helped me a lot. And then I also had a sort of a running coach who became kind of like a personal coach around personal habits and stuff with no no real business background, but I took lots from from from both, so I agree, I don't think it has and we both like through FCN, you know, some and Varjex Change, both of them some amazing coaches that don't have that founder background, but are but are brilliant that's focusing on certain aspects.

SPEAKER_00 16:03

Absolutely, and I think there's two things there as well. I think also one you you mentioned about one of your coaches, well both of your coaches you trusted and you respected them, and you you know, I think that is something that can absolutely like cannot be diminished in terms of how important that is, because a coach might have a really impressive CV and have exited all these companies, but if you get on that chemistry call and you don't you don't actually connect with them, you know, you have to be able to have this relationship of trust and both ways, right? And so that's what I think that's something that found you know, founders all of our founders they love data, they love like what makes sense on paper, but it's like there is actually just something that's like intuitive and and more subjective, and you're only gonna know that once you put maybe in the chemistry call, or you know, you might get it wrong and after a couple of sessions it doesn't work out, and like that is also fine, and that's what I always say. You know, again, a good coach isn't gonna force you to be there because you know they want to be adding value as well. Um, so I think that is really, really important. Um, and then my second point, oh, I've totally skipped my mind, it'll come back to me.

SPEAKER_01 17:05

Well, I'll I'll throw a point onto the pile then if I can now. I think that that chemistry, I would go back to that being important. I I really think it's important because I think you need on both sides to be excited about it, and you both need to be. I I think a coach is the only true peer relationship that you have in your life. Because I think every other relationship you have, there is some element of a power game going on. That's not really a bad thing, it's just how it is. Even with like family members or a partner, there are some things you don't want to share, you want to present. But with a coach, you almost need to give your whole self to it. Absolutely. And if if you're not feeling that sort of emotional engagement, like safety, respect, enjoyment, excitement, it's not really gonna be I think it's very hard to bring your best self to that on on both sides. So I think if a co if a coach feels that they're not bringing value, they should recuse themselves, or or not enjoying it. Like if they can't bring that kind of unconditional positive regard, they should they should be removing themselves from it as well. And that and that's fine.

SPEAKER_00 18:12

Absolutely, and I think also for for the founder themselves, they should really be analysing kind of after every session, like well, if they're clear on what they want support on and what success would look like in six months, if they were to work with this coach for six months, actually kind of coming out of each session and being like, How have I come away feeling from that? Like, how am I thinking differently? How is this showing up? And you know, beyond that, don't just kind of turn up for the session every week or every other week, whatever it might be, and then just like, oh, you know, because then you can actually see how it's progressing. Um, I think that is particularly difficult for um founders that haven't had coaches before, because after a few sessions, they're like, Oh, don't feel any different. It's a bit like, I don't know if you meditate, James, but you know, like when you start meditation, you're expecting this like, whoa, I'm gonna be so different, like something massive is gonna click for me, and then you're doing it for a couple of months and you're like, nothing's happening. I think it's actually just being really clear on like tactically how you would be wanting to feel different or think different or react differently to things, and that's what you're working on with your coach, and kind of being able to almost quantify that um so that you feel confident that you are working with the right coach. I've remembered my other point, by the way.

SPEAKER_01 19:18

Go for it. Let's start, let's go, let's get back to point two.

SPEAKER_00 19:21

I was gonna say, um, there's that other point of like if the CV is really impressive and you're working with this coach who has coached, I don't know, all of the unicorn founders in the UK and Europe over the last half many years, and they've built this really successful empire. I think you mentioned kind of that peer-to-peer element, which I think is so important. I think you can really tread into dangerous territory if there's a bit of like hero worship going on, or kind of like my coach, you know, that there is that power dynamic, and I've actually seen that play out in in some ways. Um, and then you just become like the coach, everything the coach says is just right, and then you, you know, you totally lose. And actually, I think the best coaches help a founder to really connect with like they have built this business from scratch, they are the only ones that know all of the context and know their own limitations, and enabling them to kind of you know be their own like guide, uh, but with that peer-to-peer support instead of I know better, I've done it before, which a good coach would and that and that's when you start drifting for from coaching into mentoring.

SPEAKER_01 20:22

If you ask like, what do you think I should do on a regular basis and like any of you getting the answers? You are drifting away from a coach relationship. I think I I do think this idea of the purity of coaching, not getting answers. I don't think edge current experience is true. I do think at times you do have an opinion, you do have to share a start few. You you can have a point of view, it's just if that's a regular point, it's becoming like your game plan rather than their game plan. Which going back to your lap thing, it's kind of if it's not founder-centric and it's not about having the founder be the best version of them, then that's just starting to drift away from coaching.

SPEAKER_00 21:00

Yeah, that's spot on. You can also just you can contain it quite easily as a coach, you know, say, are you happy for me to share, you know, what what I've done in the past and put on your mentorship hat, mental hat, and then take it off again and get back into into coaching. James, I'm I'm curious, like, I think, you know, when I'm saying this to founders, they're like, Yeah, but you know, if I could have someone who could also give me advice, then obviously that's going to be more valuable. If they're also a good coach. So how how have you had these conversations before and kind of like how have you managed that?

SPEAKER_01 21:32

So I suppose I have I do have the founder background and I do so I think the journey for me has been I I started off with going, oh well coaching is pure like questions. Don't offer anything.

SPEAKER_00 21:45

It's how we're trained.

SPEAKER_01 21:46

It is how we're trained, and I think it's a really good training because it's not a muscle that you use, and when you come into it, you're so pre predisposed to give a c to give an opinion or give an answer. So I think removing that for three years is a really good. Yeah. Practice. But I think at some point it is helpful to know when to go in. And the the frame framing that I was taught generally like is the idea of it's called invisible coach, but I forget the four different levels. You've got you go all the way from invisible coach to visible coach. And you can go a bit into each, but you want to be spending like maybe 80% of your time invisible coach, and maybe like 5% invisible coach, like in the most extreme, like I think this, like I think you'll make a mistake, or can I offer that this is this is a bad idea, or and I think you need to build up capital and trust to deploy it, but I think if you deploy it too often, you start again crushing the so I I think I think to answer your actual question, I think that the uh in my experience what people think they want out of coaching and what that actually helps them is different. And I definitely think in terms of that building credibility, that initial kind of like, can I help you? Being able to say, I've done this myself, it's helpful. But I now talk more about what I've done for my clients and what I've done for myself. I think that is more relevant, but I've been doing it for like six years. So I have more like case studies to show like I've helped this person do this. But I think allowing founders to discover for themselves what coaching is quite helpful. So I suppose I'm not already answering it, I'm not sure, but I do think in terms of that selection, having that that background is credible, I wouldn't actually use that background as much as a founder would think I would during coaching, because I don't think that's helpful. But I wouldn't even have that conversation up front because I just let them see the impact after the first three months. And then, oh, I'm making progress, and they wouldn't really think about how much. But I have given myself more permission as I become more experienced to deploy other client experience, my own experience challenge, and step more easily into advisor or mentor um or something in provocator.

SPEAKER_00 24:10

Yeah, no, absolutely. And I think sometimes actually, yeah, almost not giving the advice would be a disservice, or not or like not giving the data of what you've seen before or what you're seeing with other clients and kind of that pattern recognition or you know things that have worked and haven't worked. Sometimes not sharing that data feels more of a disservice. So I kind of try to say, like, okay, this is the training. But actually, I do think in this instance I'm gonna ask whether they want to know kind of what other people have been working with or what I've seen across the portfolio, whatever it might be. But yeah, I I think that actually what I find, you know, I've been a founder, but not in like a tech-based VC back company, but a lot of the the really useful nuggets that I have or kind of quick unlocks that might like tactical unlocks are from my experience of now coaching lots of other leaders and lots of other founders in similar in similar positions and different uh similar stages. Um, but I also I think there's times when you know the training goes out the window and you just want to jump in and be like, I know the answer to this, and actually holding back and holding space for that silence, which becomes less and less uncomfortable, but I'm still working on it. And then suddenly, like in the next five minutes, you see like the biggest unlock, and I'm like, thank goodness I didn't speak. I would have cut it, you know.

SPEAKER_01 25:24

I think that's like I think I know the answer. Often you don't have all the density you need for that necessarily to be the answer. So the answer they, I mean, two things. Sometimes the answer they come to is different to your answer, which is fine, and sometimes it's the same answer, but it lands so much better if they come to if a client comes to it themselves. Like I'm sure we we've all thin examples where we've told the same thing like a hundred times by our parents, our friends, whatever, and then we go, we suddenly experience the pain. Oh, we should well that's how it works. Everyone around you're going, we've been saying that for like the last three years.

SPEAKER_00 26:02

Yeah, yeah, yeah. No, absolutely. Yeah.

SPEAKER_01 26:06

Um but I think I mean I think founders are one of the jobs of a coach is just is just to help founders see how amazing they are. Because I think there's so much like negative, like narrative around it. It's so much pressure on themselves, it's like I need everyone else first, and this is such this has to be such a tough journey. I think just provide a safe space for founders to think and reflect and like not give their first thought to someone else and just share if they're having a really tough time. Like, I think even from a non-strategic point of view, yeah. That peer relationship is so valuable because you're giving so much energy to other people so much, just have someone that's actually focused on you.

SPEAKER_00 26:53

Yeah, I couldn't agree more. I think kind of obviously I'm kind of in my mind thinking of the split between my role as the people in talent kind of um portfolio support and partner at Octopus, and I do find like I'm in a really privileged position because I build real relationships of trust with the founders, but also very aware that they are still very aware that I'm employed by the VC. So how open that relationship can be is kind of you know, but but we do get really into it, and I think it is a very special relationship that perhaps an investor director wouldn't be able to have because they're on the board. But then I really also like cherish my coaching, like pure coaching relationships, because I think that is a space where, as a coach, exactly as you says, like our role is to come in and see the coach, see the founder or see the client as the best that they can be, um, and then bring them to that through, you know, like kind of come with that energy because they might come in and they've had the worst week and like everything's falling apart, and we have a container that actually is like, we're not gonna meet you there. We'll meet you here, and then we'll bring you bring you to where we are. So I think, yeah, it's such a kind of nuance, and that's not something you're gonna necessarily get from a mentor or an advisor, right?

SPEAKER_01 28:05

That's not their job, it's not their job, and it's it's like I don't think as a manager you can be a coach, you can bring coaching skills to a relationship, but if you can fire someone, you can't be their manager, you can't be their coach. That's likewise of sometimes VC partners go, I can I can coach them. You can't coach them, like again, that's not a peer relationship, like and that's not their job.

SPEAKER_00 28:24

Yeah, exactly.

SPEAKER_01 28:25

That's not their job, you're you're not there to coach them.

SPEAKER_00 28:28

Exactly. You wouldn't be able to see your job properly as a a part, you know, as an investor director if you're if you're if you're genuinely their coach. I see it quite a lot. Um, a lot of chair people kind of how a founder will describe their chairperson is like they're also my coach. I'm like, they they just like by the very nature of it can't be. So they need to choose whether they're your coach or they're you know, they're chairing your board because the two things just don't, you know, they are actually mutually exclusive exclusive. Of course, in any relationship we have, we can coach each other, right? You know, you can ask the right questions, and but it's exactly as you're saying, it needs to be that pure peer-to-peer relationship and dynamic for there to be that trust, and yeah, no, yeah, you you shouldn't be able to be fired by your coach, exactly. I think that's a really good starting point.

SPEAKER_01 29:14

Um then before we go back to like well, how do you choose one? It sounds like so. One is being clear what you're looking for, two, checking chemistry, three, looking for stuff which is I suppose not over-indexing on previous on a previous experience match. Yeah, which I suppose almost goes back to hiring, doesn't it, in some ways? Like I think when we hire we over-index on proof's experience, yeah. And that's it's much more about values alignment, underlying competency, like all of that stuff, and experience is just like a sometimes a poor indicator of fit.

SPEAKER_00 29:52

Exactly. Or like the big logo is sometimes a poor indicator of fit, right? But it's a quick way for your brain to be like, ah, trust, you know, and credibility. Don't get me wrong, I do think, of course, like I know many, and I often recommend many kind of ex-founder coaches, including yourself. Um, and I think that there is obviously intrinsic value in that. Um, it's a certain type of person, they've got that grit and determination, they have walked in similar shoes to a founder. So I I totally get that. But I do think, yeah, it's the over-indexing part. Um, and I also equally work with and recommend phenomenal coaches who have never been a founder themselves, but have worked with many, many different. I think that's that's more of an indicator. You you know, who have you worked with? I think that's a better question.

SPEAKER_01 30:35

I think it's a great question.

SPEAKER_00 30:36

What types of clients do you work with? Do you have testimonials on them? What types of unlocks have you been able to achieve with them? I think that is a lot more important. We should be asking even ex-founder coaches those exact same questions because that's what will actually determine whether someone's a good coach or not, you know, more than kind of say CV.

SPEAKER_01 30:55

I think it's a great point because you again, it's not to say that people who are all ex-founders can't make good coaches, but it's people who ex-founders do make good coaches. What have you done as a coach that leads me to think that you can do this again?

SPEAKER_00 31:10

Exactly. And I think the value of coaching shouldn't be measured by how great the coach's ideas were in a session, but instead how much the client has kind of been able to improve their way of thinking or kind of like got to an answer themselves in a session, if you're looking at it kind of on a micro session by session kind of success metric.

SPEAKER_01 31:34

That clarity. I think the very much you raised quite early on. Like, what what is the problem that you're trying to solve? Because I mean, we both like there are certain people I work with as coaches, like when it comes to co-founder dynamics, I know some I know some coaches who are like that's what they focus on. They just take it to a depth which is just like wow, it's kind of like you're doing this all the time, you think about the theory around this, you're experiencing it on a regular basis, like you understand this to a depth that I don't. And it's not to say I can't do it, but like just just the the rigor and the and the patterns and thing, like or it could be mental well-being or balancing like so with a young family, or like I think do you think as well, one thing we're interested in doing like founder coach network is just working with other very experienced coaches and just understanding actually those you can fragment even founder coaches into, and it's not just by stage, it's by what they really, really care about. Like for me, that's probably like management and execution of what that means, like founder management team, which which also like his previous experience brought into coaching. But when you really talk to someone about if you're clear on your problem, you go to find, they should be able to say, Okay, I had I had a client call with someone on Friday, and they had found me through like an um some online recommendation, and I was just laughing as they were susspots, but smiling as they were talking about stuff. I said, I'm gonna show you something in a second when you when you've finished outlined this, which is gonna basically mirror all the things you were just talking about. Like it's almost like what like I have this problem and this problem, this is and it was, it's just like that. That's not to do necessarily previous founder. That's just like really that is you really understand what your sweet spot is.

SPEAKER_00 33:34

Yes, exactly.

SPEAKER_01 33:35

So I think if you can really define your pain point, then a coach should be able to really show how their sweet spot matches your pain point, and that's not about background necessarily.

SPEAKER_00 33:46

Absolutely, it's um it is that repetition, I think. You know, actually finding, and I again like get it in my in my role at octopus, but also in my coaching, the same patterns that come up and all of those things which help me to be better at octopus because I can then proactively be like, this is gonna come up probably, so we should get ahead of this. Um but yeah, and I mean it should be context kind of agnostic in terms of coaching, right? So even if you have been a founder, you you could you could very successfully coach a founder who is now kind of exiting at Series D and da-da-da-da, or going you know, going public, because actually that's not the point. Um, it is more about kind of understanding them as a person, their own limitations. Uh, and if you work for them with for a while as well, you kind of you really do get to understand kind of under the hood what those people are battling.

SPEAKER_01 34:33

The under the thing's important because I think as a coach, I think one of the things you people don't back on coaching is how much of the self-work or deep work they probably need to do. It's often the business problem is a personal problem, the personal problem is a business problem, and if you can't build that relationship and trust, you're not gonna open up on some of that personal stuff, and therefore you're not gonna get the massive ultimate impact. You can really change stuff.

SPEAKER_00 34:59

Yeah, yeah, yeah. I think another thing I would say is I'm thinking about a specific coach that I know, and she is phenomenal, and she hasn't been a founder herself, but she's now worked with like hundreds of Series B plus founders. She's worked with some people in our portfolio, and this the amount of trust that these founders have in her is really kind of promising and really great because initially, when I was kind of looking at all the different coaches out there speaking to Lows and Nows, I was like, Oh, you know, I don't know how I would kind of position this to our founders because you don't have any kind of operator experience at that level. But what really helps is that founders really trust other founders, like a recommendation from another founder goes a lot further than a recommendation from anybody else, and I think for some coaches, there's also now like a bit of a FOMO, like, oh, well, my peer, this other founder, worked with this coach, and they've just like, you know, that you can see the change in them, and they are, you know, operating in such a different way, and their business has gone from X to X, X to Y, sorry. Um, and I think that that that is another way, also, I think, as a coach, building that portfolio of like testimonials and references that you can easily rely on because it is so subjective. Obviously, that doesn't mean then that it's gonna be the right person for another founder because there is all the other elements, chemistry, etc. etc. But I do think being an ex-founder opens the door more quickly and credit, and like in terms of credibility, like that's probably gonna get you that first call. But post that I think everyone's kind of on a level playing field if a founder really understands what they want from a coach.

SPEAKER_01 36:32

Yeah. I suppose so there is there is, I would all think there is some responsibility on the family to do what's right. It's like that there's not a magic bullet of just going, I'll just go and ask your EC or go and ask your peers, or yeah, yeah, 100%.

SPEAKER_00 36:48

Ask Claude. Ask Claude, exactly. I um, or Claude can be your coach actually, who needs coaches. But I think what's most disheartening for me is when I feel very passionately that someone could really, like, well, I think we could all um really do with coaching. I'm always working with a coach myself or or multiple coaches. Um, but you get a founder in front of a coach and they kind of just go into it because they've been recommended by their VC that they should, and then they have a few sessions, they're like, I actually don't rate coaching, and then you know that they're not going to be an advocate for coaching for their leadership team, and it's just like you actually just need one person to become an advocate for it, and you know, maybe even kind of add it as a benefit to their employees or whatever it might be. But when people come to me and they're like despondent or a bit like negative about coaching, having had some sessions, it's like you went into those sessions not knowing what you wanted, and it's not for the coach to make sure that you've had a wonderful session every session, like you do have to drive this, and you can you'll you'll get out of it what you put in. I think that for me is worst-case scenario because then people actually become detractors of coaching, and I think it's like actually that prep before and making sure that people are really bought in before you know you suggest that they go and have the chat.

SPEAKER_01 38:01

I mean it's a good point because I'm not sure you can convert people into if they're doing it because they feel they ought to or they've been told to. I'm not sure they're in the mindset to take ownership of the journey.

SPEAKER_00 38:16

Absolutely.

SPEAKER_01 38:17

And if they don't if they won't take ownership of it, like you as as as a co I suppose there's different sports coach and a business coach, like maybe you go to a sports coach, they're gonna sort of as every mate Hollywood sort of training montage really push you, push you and hold accountability and like but that's not a peer relationship. That is a that is something that's like a teacher or a trainer rather than a coaching thing. And I think I do find sometimes you'll come to coaching with a almost use coaching as a as a procrastination tool. It's like, oh, when I fix this, then I'll then I can be great. It's like no, you you you do need to take action now. This is not just a talking thing, it's like you will have reflections, but you do need to do stuff. And if people are not willing to take ownership of that, I think that's the thing I probably find the most frustrating is coaching. Like I work very well with action-oriented founders, I'm very good at helping them get clarity, then they take action. Yeah, I think some coaches might be better at like really helping people drive forward. I just really strongly feel like that is not my role.

SPEAKER_00 39:27

Yeah, yeah, yeah.

SPEAKER_01 39:29

Um so yeah, I think probably worth in this asking yourself as a founder, are you doing this because you really believe in it and want to, or doing it because you feel you ought to? And someone says, Yeah. Are you looking for someone to fix you?

SPEAKER_00 39:41

Yeah, exactly that. Or are you looking for to fit like to to grow yourself and to get some support from someone who can kind of be your partner in that and be your peer in that? I think this is something that I kind of um tooed and froed with a bit um when we were building out our coaching hub, Outsports. Um, because some VCs do uh provide um investment for founders and they will pay for uh X number of coaching sessions. We don't do that. Um, it is very much that you need to invest it in it yourself financially from the funding. Um but I do think that actually for me, I'm fine with that. Um, because it does mean that then people, you know, founders have to decide whether this is worth how much they're gonna pay the coach for them, instead of just kind of like you literally it is being paid by someone else, you've got no skin in the game, and you just turn up. I think that really kind of changed the dynamic dynamic of the whole thing. Um, and they're less likely to just turn up and waste their own time and the coach's time if they're having to pay for it.

SPEAKER_01 40:43

Coaching is an investment. I mean, it isn't, it is not for a good coach, it's not you should make insignificant money. But if you find the right coach, you're you can make your year payment back like in a session. It's kind of like you make a difficult decision quicker, you've saved a person's salary for a month, or you made a better decision, or you've kind of you grow faster, and we find a new client. Like it can really point to sessions, like, okay, well that's just that's just paid for the year then. That's like that's up enough time to like actually in terms of you're getting from I don't know, let's say a business worth 10 million to 100 million. Like that and and and probably quite importantly, actually enjoying the journey and not feeling isolated and not feeling burnt out. Yes, that's actually probably worth a lot more money than you are actually paying. So I think coaching can either be very expensive or it can be very cheap, if depending on uh finding the right match.

SPEAKER_00 41:38

Yeah, absolutely. And and that whole point on the ROI of it, I think, again, very data-driven founders, um, wanting to know, okay, if I do six sessions and what's the R ROI on that, you know, like this is a big investment, and and actually like some of it is like not quantifiable in terms of as you just said, getting to your next milestone, but feeling better, feeling not burnt out, feeling like you weren't isolated in that, you were supported, being able to react better to stresses, being able to manage people better. How do you kind of put a number on that? And I'm not sure if you've kind of worked out the like the magic equation, James, but that is something that I often get pushed back on from founders, and it and it's a fair point. You know, they want to make sure that they're if they're gonna invest this time and money, that they know exactly what they're gonna get out of it, which is kind of so nuanced.

SPEAKER_01 42:27

I mean, there's so well research on this, but the stats say it's 600, it's a six times RRI on on coaching, on the the last study. I think it was done like 10 years ago. Um, and there's only one big study that's having done on it. Uh instinct that I think is high. Like I think, particularly a team like Series A, Series B founders at least. The the value of getting to that next milestone is so high in terms of amount raised, the valuation you get. Like it's not just getting to the next milestone, it's getting to the next milestone in a good shape because otherwise you're squeaking your next raise or you're blitzing it. And even just the difference in that is millions, like tens of millions. Like if you're spending 20k, 30k a year on coaching on a on a two-year thing, let's say you spent 60k on coaching and additional support, and you your next raise is 10 million pounds more 20. Like those are not crazy multiples in terms of what what the difference that you see, or it's not hitting at all that that support.

SPEAKER_00 43:33

Yeah, exactly. It's the like where would you be if you hadn't had the coaching? You know, like what would you not know? You kind of don't know what you don't know until you start it, right?

SPEAKER_01 43:41

Well, that's often what we're coming to like almost that six months in, but she's like, Oh actually, I can now see. I've got enough data to see I'm not on track. I've got enough data to see if I continue this path, I'm either gonna squeak my next raise or I'm gonna miss it. I need to fix this.

SPEAKER_00 43:57

Yeah. Yeah, yeah, yeah. Can you fix me?

SPEAKER_01 44:02

Yeah. Where can you start?

SPEAKER_00 44:04

Yeah, exactly.

SPEAKER_01 44:06

Right. Um okay, so it feels like just to summarise, we've got be clear what you want. Don't be blinded by the experience. Get testimonials and ask for like relevant case sort of examples of of people through a similar situation. Um, what else have we got?

SPEAKER_00 44:29

Find someone who is supportive as a coach but not necessarily comfortable.

SPEAKER_01 44:33

Yes.

SPEAKER_00 44:34

You don't just need you don't just need like a cheerleader pep talker, that is part of it. You need someone who's gonna help you grow.

SPEAKER_01 44:40

Yeah, actually one of my clients was only the famous his favourite Session ever was when I told him he was talking bullshit because he he had this narrative with his head around you couldn't hire great people. And I was like, you are amazing, like you you you've raised great things, you've you've like you can persuade people to almost do whatever they want to do. Why does that not apply to hiring? Yeah, and actually the next two hires are amazing and locked, like and it's like I'm so glad like I almost accepted that feedback from no one else, yeah, yeah, um and that's the trust right that's the trust. That's a year and a half's worth of sort of relationship, allowing you in a moment just to go, that is a nonsense.

SPEAKER_00 45:19

Yeah, exactly. Um, so yeah, so uh chemistry, chemistry, and I think kind of following on from that is like not being not being worried to kind of pivot and be like this isn't working after I don't know, give it a good go, but that's fine as well, you know. Then try another thing. Like, don't let yourself just hate coaching or think it's a waste of time. You know, there's there's plenty of coaches out there, you will find the right match.

SPEAKER_01 45:43

Yeah, amazing. Well, Jeeves, thank you so much. I loved uh talking this through.

SPEAKER_00 45:49

Yeah, me too. Thank you so much, James.

SPEAKER_01 45:53

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