How to Coach CTOs 👑 — with Joel Chippindale - podcast episode cover

How to Coach CTOs 👑 — with Joel Chippindale

Mar 21, 202545 minSeason 3Ep. 5
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Summary

Luca Rossi interviews Joel Chippindale, a full-time CTO coach, about the role and benefits of coaching in the tech industry. They explore how coaching differs from mentoring, the advantages of both one-on-one and group coaching, and delve into the most common challenges CTOs face, such as feeling isolated, effectively integrating with the executive team, and communicating the value of technical initiatives. Joel shares insights from his work, emphasizing the importance of building trust, understanding business priorities, leveraging individual strengths, and mastering delegation.

Episode description

Today's guest is Joel Chippindale!Joel is a full-time CTO Coach and one of the coaches-in-residence in the Refactoring community, where he runs monthly mastermind sessions and other community events.So with Joel, we dived into what coaching is, the difference with mentoring, one-on-one versus group coaching, and what are the top challenges that CTO faces today, based on the work that Joel does with his coaches.02:34 Introduction03:40 Joel's journey in tech05:21 Finding a definition of coaching07:25 Mentoring and coaching roles10:22 One-to-on and group coaching12:53 The "hows" of coaching15:12 Is coaching a widespread practice?18:35 Top CTOs challenges21:43 Right support for right challenges26:08 Advocating for technical work31:53 Commonalities and uniquenesses in CTOs challenges34:20 The platonic ideal of CTO36:49 Choosing what to focus on39:48 How to delegate properly

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Transcript

Intro / Opening

I think there's a real danger of being a CTO that you imagine that there's some sort of platonic ideal for a CTO out there. And all CTO roles are different, but also as CTO, you have a lot of control over how you develop your team. and what the shape of that role looks like. And you reminded me there, part of your work is to understand your own strengths and weaknesses and think about the team you build around you.

Episode Introduction and Topics

and the people you support around you in order to make you whole as a team rather than as an individual, as it were. Hey, Luca here. Today's guest is Joel Chippendale, who is a full-time CTO coach. and is also one of our coaches in residence in the refactoring community, running our monthly masterminds and many of our community events. So with Joel, we dived into what coaching is.

the difference with mentoring, one-on-one versus group coaching, and what are the top challenges that CTO face today based on the work that Joel does with his coaches. So let's dive right into it. after a short word from our sponsor. This episode is brought to you by WorkOS. If you're building a SaaS app At some point, your customers will start asking for enterprise features like same authentication, scheme provisioning, and fine-grained authorization. That's where WorkOS comes in.

making it fast and painless to add enterprise features to your app. Their APIs are easy to understand, so you can ship quickly and get back to building other features. WorkOS also provides a free user management solution called AuthKit, a complete out-of-the-box user management system that's free for the first million users. It's a drop-in replacement for Auth0 and comes standard with useful features like domain verification, role-based access control, bot protection, and MFA.

It's powered by Redix components, which means zero compromises in design. You get limitless customizations as well as modular templates designed for quick integrations. Today, hundreds of the fastest growing startups are powered by WorkOS, including ones you probably know, like Cursor, Vercel, and Perplexity. So check it out at workos.com to learn more. That's workcos.com. Hi, Joel, and thank you so much for being here with us today. Thanks for having me, Luca. I'm looking forward to it.

Yeah, so Joel, we know each other very well because you are one of the coaches in residence of the refactoring community and you run, together with Melinda, our monthly mastermind sessions. But of course you don't work full time for refactoring mainly because I wouldn't be able to afford that.

but you are indeed a full-time CTO coach. So I'm biased, but I think the work we do together is awesome. And the work you do is really, really interesting. And I think not everybody in tech is really aware of how coaching works, what are the opportunities for CTOs and also other people in tech. So I asked you to come on the show to tell us more about coaching, how it works and the challenges possibly that CTOs face today. But I will take a step.

Joel's Path to Coaching

back and before we dive into it i will ask you just what has been your journey in tech so how did you even end up working as a full-time coach where to start so i i think So after I left university, my dad said this internet thing, it's probably going to be interesting. And this was back in 1994. And I went to an internet cafe and I browsed the web for about 20 minutes.

and said this is rubbish it'll never catch on fast forward a few years later i was a maths teacher and all my students were spending their lunch time this high school students on hotmail messaging one another and it was that point I really got it I think and I got into programming then

Left my job, set up a small startup in EdTech. Failed to make any money, but we taught lots of people. It was fun. And I learned a lot about programming. And from there, I really focused my career on technology. And quite quickly... shifted from seeing the most interesting problems as being technology problems, being people problems, and getting into managing teams, etc.

and then the last 10 years i say of my career 10 15 years were mostly a cto at various startups and i got coaching as part of that and got trained to be a coach and found that incredibly powerful and in the end i decided i wanted to drop all my other responsibilities and just do coaching and so the last four years where i've gone

Solo, working as a CTO coach, have been an experiment in seeing whether that's possible. It turns out it is. So I feel very lucky. Love this. Love this story. So if you had to define it.

Coaching vs Mentoring Defined

what what is coaching for you so maybe i'll talk about mentoring first because this comes up a lot yeah and many of the people who talk to me initially are thinking about mentoring So mentoring is where you get to speak to someone who's got different experiences than you, and you can learn from those experiences. And that can be really valuable for accelerating your learning.

coaching on the other hand comes from a slightly different place coaching comes from a place of assuming that you're a capable and resourceful person and therefore most of the answers to your challenges are already in your head somewhere they just need help getting out and so in that in that way coaching is a thinking partnership to help you become clearer about yourself

and the situation you're in. Maybe challenge some self-limiting beliefs that you're holding on to and then examine the options available to you for change and support you to commit to one of those. when i work with clients i do a mixture of coaching and mentoring but we always start with coaching and that's the majority of what i do because it tends to get better outcomes for my clients builds their self-confidence

It provides them with solutions that work for them rather than for me. So you said mentoring relies more on the fact that the other person can help you directly. possibly because they had experiences that you don't have as the mentored person and these experiences are relevant to you because maybe you have a challenge you're facing and the mentor.

is somebody who can help you directly providing a solution or direct help while the coach is more of an indirect relationship the way you put it right that's right yes

Internal vs External Support

And so both mentors and coaches are like relationships that you can have either inside your own company or working with a professional or how does it work like in the industry? Yeah, I think you can get mentorship and coaching both from within your company and outside the company. Most of the people I work with are the most senior technologists at a startup or scale-up.

And so often there is no one who can provide them with useful mentoring within the company. It can be really valuable to look for a mentor outside your company, someone perhaps. who is also maybe a CTO, but is a bit further on their journey than you. Coaching again can be complex from within the company. In order for coaching to be effective,

You need to be able to share your thoughts and feelings with your coach and they need to be able to support you in your goals. And that can be complicated within a company. Perhaps.

Your CEO is offering you coaching if you're the CTO. And that's complicated. Perhaps one of your issues is your trust in your CEO, for example. You may not want to expose all your thoughts and feelings to someone who... is essentially evaluating your work at the same time so that can be complicated and so i think for both those reasons for more senior people it can be really valuable to have an external mentor or coach rather than one internally

Who Benefits Most from Coaching

yeah so do you think that people who benefit from coaching are mostly CTOs or executives or senior leadership or this is beneficial even for middle management or maybe senior individual contributors what do you think so bill gates says everybody needs a coach and i would definitely agree with that coaching can be valuable for everyone that said I do think it is more valuable for people in more senior positions.

when you're the cto as you get more senior there become less and less people that you can turn to for advice and support and to run your ideas by and so there's there's greater value in having someone external for that also if you are able to change your behaviors as a senior leader you have a much greater impact on your team and your company than perhaps someone who's more junior

and so it can be more valuable even to have that external coach or mentor yeah makes a lot of sense and i know of course that you run both

One-on-One vs Group Coaching

uh one-on-one coaching and also group sessions and group coaching mastermind sessions like you do with the refactoring community so what is the difference between uh one one programs and group programs in terms of um who are these four what are the type of challenges that they're helpful with and so on so there are some similarities

but i think so one-to-one coaching where you have your own coach and you have individual sessions with that coach on a regular basis enable you to focus on what you need at the pace you need and they enable you to go as deep as you want the coaching is all about you and what you need it's also easier to build trust with one individual coach than maybe a group of people that you're working with and so it can be easier to share

perhaps some of your fears and challenges with that coach. And I think one to one coaching is particularly valuable for periods of transition. Maybe your company is changing. Maybe your role is changing. Maybe you're changing companies and you're having to form a bunch of new relationships. And so you're going through very rapid change during those periods.

one-to-one coaching really focused on the change you need is particularly valuable working in groups and being coached as a group you're supporting one another and as a group learning coaching skills in order to do that and this exposes you to a much wider range of perspectives it generally requires less budget and as lower intensity and i think it's really valuable for that ongoing development

to make sure that you're continually re-examining and developing your skills and it's a useful point of challenge a useful space to get new ideas to check in on your existing ideas. It's also valuable for just feeling like you're not alone. Meeting regularly with a group of other senior engineering leaders, other CTOs reminds you that the challenges you face, you're not facing alone.

Everyone is facing very similar challenges and worrying about similar things and that in itself can be really powerful in building your confidence in yourself and enable you to perform at your highest ability.

How Group Coaching Works

Yeah, love this. And do you, when you create these groups of people, for example, when you create these programs for groups, are they created around? some come on specific challenge that participants need to be facing or it is higher level just based on the role maybe people are having their company and so this is like a broader personal development how does it work so there's all sorts of different ways to run group coaching but the the groups that i run get a group of

maybe six or seven CTOs together and we meet monthly for a year. Yeah. And in each monthly session, uh, individuals within the group share challenges they're facing at the time.

and the rest of the group support them in that challenge that means we've got the same group of people meeting again and again and again in order to build trust and knowledge with one another and i select people who i think will complement each other in terms of their skills and background and experiences and so there's no set what's the word it's not like a curriculum

uh as it were and every individual within the group will have their own goals it's a group rather than a team but they're supporting one another in those journeys yeah so in these cases i guess the role of a coach like yourself is more that of a facilitator in the conversation rather than working directly on the issues with the with the coaches absolutely and you know i will support people to have those

more coaching conversations with one another yeah and to offer not just advice but insightful questions and challenges to people's assumptions and again I can also take part in that. So if I think there's something the group is missing, then I can share that perhaps from my experience or perhaps from that challenge or perception of what might be going on. for the individual who's brought a challenge along. Yeah. And do you think that coaching either one-on-one or in groups context is...

Coaching Adoption in Tech

sufficiently widespread in the industry or do you do you find resistance within companies in in supporting this kind of support for their for their senior executives because from my i'm asking because from my perspective kind of from the outside because i'm not a professional working on this all the time. I feel that it's still not so widespread or so I wouldn't say well received, but not so common yet, even for CTOs or founders.

who instead, it's obvious the kind of benefits that you get. Yeah, I mean, it's an interesting question, really. And I think it is changing over time. I think coaching is becoming more and more normal.

but if i think if i think back to my own experience of developing as a cto i just wasn't aware of the possibility it wasn't something people around me talked about as a way of getting support and i i felt like i needed to face all these challenges and developments on my own which in retrospect i don't know what i was thinking if i could go back and tell my earlier cto self one thing it would be get a coach

um as a result i think i learned to be a coach what i call the expensive way yeah it's learning through trial and error with the cost of my mistakes being borne by myself and my own mental well-being But also those of my teams and the companies that I worked for. And it's not that coaching will mean you avoid making any mistakes, but it will enable you to accelerate your learning and learn much faster in that environment. And so...

I think there is an assumption that people learn to be CTOs just by being CTOs. And although there's some truth in that, I don't think it's enough. And I think it's... There can be a huge return on investment for companies in terms of investing in the development of their most senior leaders. So they perform better. Everybody wins, as it were.

and it is becoming more normal but still the vast majority of people that i coach have never been coached before and the reactions within companies are very different the one thing i really notice is where if in a company where the ceo has received coaching in the past they are almost always really supportive of their ctos getting coaching in fact the cto asking for coaching often avoids that difficult conversation where the ceo is worried that

if they offer coaching the cto will somehow feel like they're being criticized in some way and being told they're not good enough yes so i'm yeah i think it is changing slowly but there's a lot of awareness i think yeah

work on. I can totally relate with your younger self thinking that they had to face this struggle alone because as a young CTO myself i mean first of all i think i never really thought this was a possibility so as you said because again probably back then in 2012 2013 it was even less widespread especially in Italy, which is such a small ecosystem. But then again, I probably even thought that my own challenges as a CTO were so peculiar and unique.

that you couldn't possibly get mentored or coached successfully, but that's of course a complete fallacy. But I guess it takes more experience to see that.

Top CTO Challenges Today

So I wanted to ask you, by working with so many CTOs, what are the top CTO challenges that you get, that you receive, that you get from your coaches?

That's a really good question. I think the central challenge is really that of not knowing who to turn to for support. I think our roles as CTOs are... i think we're really lucky to have them in many ways it's a really exciting role to have you have a huge degree of autonomy you've got new challenges coming up every week and that can be really rewarding um but it

also comes with as we said that sort of idea that you have to face all of this alone that you feel like there's no one around you to support you when you're stuck and so I think primarily that's why people reach out to me for coaching i'm a big fan of i don't know whether you've seen lara hogan's article when your manager isn't supporting you build a voltron and what what she says in the article is that

your manager will never be able to support you in all the ways you need support it's not necessary that they're a bad manager it's just that's not possible and that's even more true i think as you become maybe a cto where your ceo is often really focused on just making the company work making sure there's funding for the company etc managing the board and you are left much more to your own devices than perhaps

you've been used to in previous roles where there's always been someone more senior than you who is in a similar discipline ready to support you. And so I think it's really important to build up that group of people who are going to support you in the ways that you need.

And one of those ways is with a coach. Yeah. So it's kind of this loneliness feeling. And I think if I think back at myself, I think I felt... like two types of loneliness because one is like inside the company because of course it's kind of a lonely job which faces challenges that It's hard to turn to someone else at the company, even your CEO or your peer or others to understand what you need to do, whether you're doing right or wrong and so on. But also.

one challenge that I personally faced is that I knew other CTOs at other startups for example some of them at similar stages than us but uh it felt like they were facing different challenges and were not in conversations with them were not always helpful and and so the the was loneliness also outside

let's say yeah absolutely and also we're very busy and you know those relationships with ctos outside your company it's very easy for those to remain very superficial because you feel you don't have time to invest in them Yeah. So I recognize that loneliness too. Yeah. And so if CTOs had these peers and this kind of support, what type of challenges?

CTO as Executive Team Member

that they will need the most help with in your experience. There are a whole bunch of challenges that come up. Think seeing yourself as a member of the exec team. can be a real challenge for people who are early on in their career as cto's i certainly found that lesson very hard to learn at one it's not that i'm

My primary team is the engineering team and I'm there to support them and fight their battles in the leadership team. It's more that I'm a member of the leadership team. My engineering or technology team is my secondary team. it's the team i support afterwards and that shift in thinking and building trust and influence within that leadership team can be a huge challenge when you're new to the role yeah i love this angle so

I have this rapid fire follow up question. Maybe it's what you were already saying, but so what's the difference in terms of like core behaviors between a CTO? who really feels that his primary team is the exec team versus one who feel more of a duty to support his engineering team first. So I think it's how they approach the rest of the exec team.

and i think it's you know a cto who's really seeing the exact team as their primary team is investing in those relationships with different members of the executive team they're spending time with them to understand the challenges that they're facing in their teams what's what's the biggest challenge is for the person who's leading on sales or leading on marketing or leading on product

or leading on customer success or leading on finance what's the biggest challenges that your ceo is facing and your first thought is how am i supporting them with their challenges rather than how am i supporting my team because there's little point in supporting your team if the company is not going to be successful when i have been a cto in the past who's not seen myself as part of that leadership team i see

Conflicts appearing, me not trusting other members of the leadership team. Oh, that salesperson's just signing that contract because of their bonus.

they don't care about the success of the company if they knew what i knew they'd know that was on you know all those things and you see that playing out in your teams as well and the different teams so arguing over these unresolved conflicts and not holding one another to account and not trusting one another so it's really that work there that i see is the biggest change yeah so basically the mindset shift is coming into your

executives' conversations with the mindset of gathering their own challenges and problems and figuring out how you can help with those as opposed to focusing on... 100% on bringing your engineering team problems to the table, like we have this tech depth, we have this, we have to implement this technical strategy, I don't know, and just advocating for your own work.

Advocating for Technical Debt

Yes, but you still need to advocate for your work, not in the sense of putting it above the needs of the company, but remembering that you need to hold your exec team members to account also.

for the commitments you've made to one another and that may mean the commitments they've made to you and your team as well as the commitments you've made to them yeah and i want to follow up with i think one of the the most evergreen topics of conversation also on the newsletter that is advocating for this kind of technical work, as you said, which is always hard and always controversial sometimes.

uh either if it's repaying tech debt or making technical investments so do you think these things have to work as a separate swim lane with respect to other like product investments or the business roadmap or Or is this something you discuss altogether with other executives based on the opportunity of doing such technical work? I mean, how do you have these conversations which are hard and are very technical?

many times so i think i think the first thing is to go back to that earlier point which is it's all about building trust and i think this is something i underestimated when i was early in my career i thought if i bring the right logical arguments Everyone will agree with me and will make the decision I need. But it's very hard for people to listen to you if they don't trust you. So I think that first job is really about building that trust for the rest of the exec team.

trust that you care about them and their areas and the success of the company that you are sincere that you mean what you say that you're reliable that you do what you say and that you're competent and until you can do those things you will have very little influence and that takes even if that's small steps that's where you need to start yeah once you have that trust

think it's really important to think about priorities rather than good ideas. One of the dangers we slip into is imagining that we should do every good idea. And in a company of 30 people, I guarantee you there are a thousand good ideas. There's no shortage of good ideas.

So what you're really thinking about when you're advocating for technical work is why this work and why now? Yeah. I think that's the first thing. It's not that it's good. It's that it needs to happen now. And then the second thing.

Framing Tech Needs for Business

I think it's really valuable to do is really put yourself in the shoes of the CEO. If you were the CEO, why would you be choosing to do this work now and prioritize it over other things? And I think if you can answer that question in terms that makes sense to the CEO and the rest of the leadership team, then you're on to a winner. And if you can't, maybe it is stuff that you should not be doing. Yeah.

And just to give you an example, you know, technical debt comes up a lot when talking about advocating for technical work. I think, and again. I tend to speak about me in these because I keep the work of my clients very confidential. And actually all of these situations have parallels in my own development. So I remember arguing that.

we should we should slow down our technical work so we could work on technical debt and make the developers in my team happier and unsurprisingly that fell on deaf ears you know think about it as the rest of the leadership team listening to this slow down the product people are going to be unhappy because they've committed to a road map to everyone the customer success people are going to be unhappy because

they you know they're talking to customers who are wanting all these new features the sales team are going to be unhappy because they're waiting on these features to sell for customers yes the customers are going to be unhappy so developer happiness

feels like a small win compared with all of this unhappiness that you're asking people to take on but if you think you know the reason developers can be happy is because they can do better work more work in future they can accelerate their work if they've

uh got rid of some of this technical debt and so if you can talk about it in those terms how much faster we will be able to go once we've we've made this investment how quick will that return on investment be what will it look like to the rest of the company then it's a whole different discussion. Yeah, and I guess this comes down again to what you said earlier, that is to understand what are the challenges.

from other people in your group in your peers among executives and try to find a way to present the work that you want to do in a way that speaks to those challenges i suppose i'm speaking to challenges that do not really understand and they're not their own i think the other thing that comes out of this is also not bringing things up to them that they don't need to be involved in

There's lots of small improvements you can make that the exec team never needs to hear about. If they trust you, it's the right decision to make. If you're thinking from that point of view, if I was the CEO, I would want this to happen, then you're away. So again, it's...

you know deciding where where you need their buy-in where it's really going to impact them perhaps negatively in the short term yeah yeah i agree and and possibly i'm even thinking when you're you're making your argument you should probably stop a moment before and think how would i react if one of my other executive peers made the same argument for their own team right and exactly would this resonate with me you mentioned developer happiness and while you you were speaking i was thinking

let's say the head of finance came into the conversation and said we have to optimize the happiness of finance people because of this and that and i didn't understand the word that yeah that's that was would probably be another great pitch for my years so yeah exactly you all need to find out fill out timesheets because it's going to make the finance team happier

for example, it's unlikely to go down well with you. Yes. I mean, it's so obvious when you try to shift perspective, but then it's not obvious at all when you're the one. uh trying to to make the arguments and i i wanted to ask you because i asked you the top cto challenges uh but are there even some do this even exist that is Can you find a lot of commonalities among the various CTOs and coaches that you work with in terms of challenges and things that have to go through?

Or the CTO role is so unique that it's an endless long tail of different things that you have to deal with? So the answer is it's both, I think. So there are very familiar themes that come through.

Common Challenges, Strengths, and Role

yeah and almost everyone i coach has got very good at almost everyone i coach has come back through a software development background and they've got very good at teaching themselves about software development And so the challenges tend to be around people in relationships. So that building trust, having influence, advocating for technical work. So these topics come up again and again, but they're also different.

for every person and every company everyone has different strengths has different ways that they feel comfortable working uncomfortable working one of the things they often talk about is is working to develop your strengths rather than just cover all your weaknesses it's about making you unique what what bring what do you bring uniquely to the role of cto and that's not just making you average you know that's about leaning into what you're really good at

And so every CTO role is different. Every company is different. Everyone and their teams are different and their exec teams. And I think that's part of the value of coaching over, for example, some sort of CTO course. It's really about meeting you where you are. and the challenges that you face and how you're going to resolve them for you and so it's also yeah it's the same but it's unique if that makes sense yes

Yeah, no, that makes totally sense. And I love your advice on strengths and weaknesses. As a matter of fact, one of the best advices that I got once from an investor was exactly about that because for a long time. As you said, I tried to improve on my weaknesses, right? Because I thought I had to be a well-rounded CTO and professional, but instead I got advised.

to double down more my strengths and possibly on many of my weaknesses just delegate that and or hire people for which those areas were strengths instead.

because we have strengths and weaknesses and of course we can work on them but there are things that make us unique which are going to stay there and it's probably better investment to focus on this and i think it was a great advice i don't know if that's what you meant absolutely and i you know it reminds me of a few other things that come up commonly so one is

I think there's a real danger of being a CTO that you imagine that there's some sort of platonic ideal for a CTO out there. And all CTO roles are different, but also as CTO, you have a lot of control over how you develop your team. and what the shape of that role looks like and you reminded me there part of your work is to understand your own strengths and weaknesses and think about the team you build around you

and the people you support around you in order to make you whole as a team rather than as an individual, as it were. And I think that's supporting people to lean into their strengths and remembering that... you know this is another shift i think as you move more into leadership is you know remembering your impact is the impact of you and your team not just you

and your job is to find where you've got the biggest leverage as it were to change that impact rather than to do all the things and be the best at everything or be the best technically or whatever it is that goes on and so absolutely leaning into your strengths and making sure your team be it your leadership team or your engineering or technology team can can support you to fill in some of those gaps

Yeah, I agree. And I, I think it's really hard and probably the, one of the things that makes it hard to, to work intentionally and the right way on that.

Managing Time and Focus

break down between strength your strengths and weaknesses is that sometimes it's hard i mean i'm thinking of myself as a cto so this is like a sneaky coaching session for myself that i'm that I put in here, but it was often hard for me to figure out what my role was exactly about and what I had, how I had to spend my time. what I had to spend my time on versus letting my team, my engineering team, for example, go with it.

uh and and also all the answers to these questions uh obviously change it with time so it was never i mean maybe i found something good for now and then six months from now it changes so Is this a topic that comes up frequently, like how CTOs need to manage their time or choose what to focus on? Absolutely. And that bigger question, as you said, is also in there that what is my role?

even yes you know it's it's very rare you will get a clear job description from your ceo as a cto and say well this is exactly what you need to do and that's part of the joy of the job you want that autonomy and to be able to be skeptical if you see that yeah exactly but it doesn't mean that that work doesn't need doing but maybe that work needs doing by you you know you need to

to be able to describe what does success look like in your role and that's a that's a conversation between the you and the ceo rather than the ceo knows exactly what that is you have to help them see them and if that's what success looks like okay well then where should you be spending your time and so both of those questions come up and then if you know where you should be spending your time

the next question is why aren't you spending it on that which is almost always the case you know and all three of those come up regularly in coaching back to that you know there are regular themes and the answers to them are always different But I work with people on all of those. I realize we've opened up the territory. Where would you like to focus? No, no, I think it's fine. And actually, I think there is a common thread.

across the various topics we have talked about uh so far it's like i mean one of the one of the best pieces of advice so far i think it's really focusing on your executive team from which I think probably is where the definition of success comes from, right? And then you turn to your engineering team to implement that definition of success.

And you have to figure out what's your role in that. I mean, what is that you bring to the table? What are your strengths and what are your weaknesses and how you delegate and empower? people on your team to implement that. If I had to tie together the things that you have said so far, does it make sense? Yeah, yeah, I like it.

Delegating and Growing Your Team

It's a mini framework that I'm going to steal for a refactoring article. So that's the right mindset that sneaks in. So as part, another challenge that I would like to discuss. I think that comes naturally when it comes to working with your engineering team and figuring out your role versus what your team should work on is how to delegate your work properly and how to grow people on your team versus what to keep for yourself.

And that was a big struggle for me as a growing startup CTO where you have to hire, but you have to figure out what to hire for and what not to hire for and how to really empower people who work on engineering. Uh, is that also a common challenge and you have any advice on that? Hmm. So I think that follows on nicely from that, you know, where, yeah.

We could talk loads more about managing your time, et cetera, and designing your role and what success looks like. In a senior leadership role like this, there's always far too much to do. You never get to the end of the week and go, i have finished everything i've done the job of cto it's all over i'll wait for new work to come in next week

and and so with managing your time the first thing to do is realize that you are going to be dropping things every single week guaranteed and the important thing is to decide and be in control of that Make sure it's you deciding what's getting dropped rather than feel circumstances and context is just battering. But once you've done that, decide what's really important for you to focus on, what you and your team really need to do.

So you can choose what stuff gets dropped. Then you know, then you can work out what you need to spend your time on, at which point you have loads of things to do that you don't have time to do. sometimes the right thing to do is just let those drop but the other times the right thing to do is delegate them to members of your team and it's really useful to remind yourself that part of what you're delivering for the company

is a better team next year. You're always thinking about how am I developing my team? How am I giving them opportunities to grow? And I think anything that you think you're the only person in the company who can do this. yeah and so you can't delegate it i think that's a really interesting question to challenge yourself on what is it that you've got that your team don't have yeah that means you're the only person who can do this

And how are you going to bridge that gap? How are you going to support them to make that change? Support them to take it on for you. One of the things I talk a lot with my coaching clients about in this is really thinking about task relevant maturity. which is a phrase which comes out of uh andy grove's book high output management and he said be really careful don't think of your senior people as senior and everything when you ask them to do something new

Remember, they might be senior in that new thing, but they might be really junior. And think about how you delegate with respect to their maturity with the task you've asked them to do.

if you're asking them to come up with a technical strategy for their area of the business and that's not something they've done before they'll probably need a fair amount of hand holding otherwise they'll be lost yes another things that they've done many times before you can delegate just assume they're doing it and everything in between yes no it makes a lot of sense it's true sometimes we just think

He's a senior engineer. He's, you know, in everything. And, and I also, it also made me think when you said figure out what is it that you should not delegate because. it's your area of unique strength and kind of brings me back. You remember when there was the whole controversy about the founder mode discussion around founders needing to be more hands on or more hands off.

And I remember hearing that the whole Branchesk interview and I felt that if the founder feels it's got too detached from work and too little hands on, it's probably because they had. they had delegated things that they had not to parts of their unique strengths that they kind of forgot and and instead delegated that as well that's what i thought thinking even

at myself in the past. I don't know. I think that's good insights, Luca. So, Joel, thank you. Thank you so much for this chat. I feel like... uh i had a coaching session myself by talking with you and i really would have loved to to get this kind of support when i was a cto but it's still nice to to get this chat as a as a podcast host so we can share it with everybody. So thank you so much for, for being with us today. Thank you, Luca. It's been a pleasure. Thank you so much for listening.

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