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"CTO in training" Danger, Will Robinson! I followed a similar path to the one you now tread. I cofounded, and managed/grew the dev team from me to forty folks

"CTO in training" Danger, Will Robinson! I followed a similar path to the one you now tread. I cofounded, and managed/grew the dev team from me to forty folks. Three years ago (after seven years of just "tech director"), I took the mantle of CTO. Error. CTO is not a technical role. To do it well, you must be technical, but it is in reality a sales and marketing role, both internal and external. I found myself isolated from our tech team in short order, as as CTO one is the public and board level technical face of the company - and that becomes all consuming, and you become the perceived source of all the problems. You become the messenger, who is much shot at, by both clients and your former allies in your technical team. The clients shout at you for bugs. The developers shout at you for pleading that bugs get fixed. You become that which lives between hammer and anvil. You are no longer part of the team. You are the boss. So - unless you want to get out of technology and want to work as a marketeer/apology bot, don't aim for CTO. I did, it broke me. I left my company today, as I started it for the love of tech, and making cool stuff - and at the point of organisational development they have reached, that is not something there's any scope for a CTO to do. Lesson learned.

antjanus 10y ago
Haha yeah, that's why I added that I don't really call myself that but it sounds better for the story. I'm basically a lead dev. I don't mind getting out of tech but right now, I'm here, and I enjoy the tech and I enjoy trying to get a project back on its rails and get to an MVP.
nbclark 10y ago
Sorry to hear this. I've been through a similar transition. 1 of 2 devs 5 years ago, growing a team to 45+ engineers today. I felt a lot of what you describe. I was somewhat aware of the split (as it was happening) between technical creativity and being the face of the team (but not actually building). I realized that building, being creative was something I didn't want to lose. I hired directors and promoted (eventually) one to VP. He and I work very closely, but the clear distinction is he runs the engineering team, and I am responsible for running the architecture group, facilitating engineering culture and leading research. Thankfully my CEO was supportive of the split I defined, and it has allowed me to not lose my identity. But for a good 2 years there, I was struggling to find the right fit. And as for getting yelled at about bugs, that's just part of the job. It's hard not to take personally, but when you realize that CSMs get yelled at so much more about bugs than we do in engineering roles, it helps put the pain into perspective.
- madaxe_again 10y ago
  Yeah, having support within the business probably helps. I was hung out to dry one time too many. I likewise promoted and hired to try to make the situation tenable, but wasn't allowed to change my role to be less client/organisation focussed - by that point I was truly shut out of the dev team. It's also very hard not to take personally when nobody else is willing to take any responsibility - everything ends up escalated, usually with clients making death threats and other such fun. Perhaps I'm just thin skinned, but I reached the point where halving my net worth just to escape was the best option.
  - nbclark 10y ago
    Sorry for the tough situation. Hope all has worked out better since.
    - madaxe_again 10y ago
      Well, it's been a day since I left, and all I've managed is to increment my age by a year! Today I need to go and actually announce my resignation to the team. Only the directors know. Either everyone will cheer, or worse yet, there will be no reaction at all. I made a rod for my own back - it just took me a decade to realise it. I guess I'm just not cut out for this.
  - agibsonccc 10y ago
    I've found dividing up the support among engineers helps this a lot. Lack of empathy is a big factor here. Having engineers understanding customer problems also leads to easy consensus and easier cross collaboration among teams. Would love input contradicting this. I'm still learning a lot myself but this has worked for us.
    - madaxe_again 10y ago
      Nail on head. There was zero empathy from anyone for anyone, except for from me for everyone. Again, part of my problem is that I probably care too damn much. If our teams, our clients, were upset it would upset me, and I spent most of my time feeling like a bloody counsellor rather than a CTO. We actually did pull development into support on a rota - and after a month of me spending two hours a day dealing with angry toxic engineers who are threatening to walk out because they've been made to look in the support inbox, or placating clients who've been brusquely told their issue isn't seen as a problem, we backed down. It turned into out and out warfare, people were naming their damn factions. Does say something that the only technical person in the company other than support to do support was me.
alexbeloi 10y ago
How long were you doing that and how did you leave the company. Meaning, you probably have a lot invested in them and they in you, how do you make that exit as soft as possible for both parties?
- madaxe_again 10y ago
  Nearly eleven years, since I started the business. they invited me to leave. To make it soft for them I'm tied into two years of covenants, and sold my equity back to the business for about a third of its value. For me, that means I have time and money, and no idea what to do with myself just yet. Could be worse - but it feels damn strange to no longer be part of what became my entire identity.
tluyben2 10y ago
I became CTO quite young and I was running around doing technical stuff when my colleague pointed out that was not what I should be doing. I was co-founder of the company, so after I read what I should be doing (which is more like what you say), I appointed my right hand as CTO and I became head of our small R&D dep. That was excellent. Now i'm CTO again; older and wiser and I fit the role now, however, when we grow more that might change. I really do want to keep coding for fun and business.
- agibsonccc 10y ago
  CTO roles at companies vary. Some end up doing "technical stuff" as well as business. How large was your team that this was a problem?
  - tluyben2 10y ago
    300something. I was too involved in the projects themselves (which is what I like(d)).
- madaxe_again 10y ago
  Yeah, my colleagues just found entertainment in watching me lose my wits (they're both stoics, very good at business but not big on the giving a damn scale, and I do worry about long term course in my absence, and think they may go steady-state from here in), and after I took some time out because I was on the brink of recklessness, suggested I leave the business. So I did. I'm pretty sure it's the right call for all concerned.

antjanus 10y ago

Haha yeah, that's why I added that I don't really call myself that but it sounds better for the story. I'm basically a lead dev. I don't mind getting out of tech but right now, I'm here, and I enjoy the tech and I enjoy trying to get a project back on its rails and get to an MVP.

nbclark 10y ago

Sorry to hear this. I've been through a similar transition. 1 of 2 devs 5 years ago, growing a team to 45+ engineers today. I felt a lot of what you describe. I was somewhat aware of the split (as it was happening) between technical creativity and being the face of the team (but not actually building). I realized that building, being creative was something I didn't want to lose. I hired directors and promoted (eventually) one to VP. He and I work very closely, but the clear distinction is he runs the engineering team, and I am responsible for running the architecture group, facilitating engineering culture and leading research. Thankfully my CEO was supportive of the split I defined, and it has allowed me to not lose my identity. But for a good 2 years there, I was struggling to find the right fit. And as for getting yelled at about bugs, that's just part of the job. It's hard not to take personally, but when you realize that CSMs get yelled at so much more about bugs than we do in engineering roles, it helps put the pain into perspective.

madaxe_again 10y ago
Yeah, having support within the business probably helps. I was hung out to dry one time too many. I likewise promoted and hired to try to make the situation tenable, but wasn't allowed to change my role to be less client/organisation focussed - by that point I was truly shut out of the dev team. It's also very hard not to take personally when nobody else is willing to take any responsibility - everything ends up escalated, usually with clients making death threats and other such fun. Perhaps I'm just thin skinned, but I reached the point where halving my net worth just to escape was the best option.
- nbclark 10y ago
  Sorry for the tough situation. Hope all has worked out better since.
  - madaxe_again 10y ago
    Well, it's been a day since I left, and all I've managed is to increment my age by a year! Today I need to go and actually announce my resignation to the team. Only the directors know. Either everyone will cheer, or worse yet, there will be no reaction at all. I made a rod for my own back - it just took me a decade to realise it. I guess I'm just not cut out for this.
- agibsonccc 10y ago
  I've found dividing up the support among engineers helps this a lot. Lack of empathy is a big factor here. Having engineers understanding customer problems also leads to easy consensus and easier cross collaboration among teams. Would love input contradicting this. I'm still learning a lot myself but this has worked for us.
  - madaxe_again 10y ago
    Nail on head. There was zero empathy from anyone for anyone, except for from me for everyone. Again, part of my problem is that I probably care too damn much. If our teams, our clients, were upset it would upset me, and I spent most of my time feeling like a bloody counsellor rather than a CTO. We actually did pull development into support on a rota - and after a month of me spending two hours a day dealing with angry toxic engineers who are threatening to walk out because they've been made to look in the support inbox, or placating clients who've been brusquely told their issue isn't seen as a problem, we backed down. It turned into out and out warfare, people were naming their damn factions. Does say something that the only technical person in the company other than support to do support was me.

alexbeloi 10y ago

How long were you doing that and how did you leave the company. Meaning, you probably have a lot invested in them and they in you, how do you make that exit as soft as possible for both parties?

madaxe_again 10y ago
Nearly eleven years, since I started the business. they invited me to leave. To make it soft for them I'm tied into two years of covenants, and sold my equity back to the business for about a third of its value. For me, that means I have time and money, and no idea what to do with myself just yet. Could be worse - but it feels damn strange to no longer be part of what became my entire identity.

tluyben2 10y ago

I became CTO quite young and I was running around doing technical stuff when my colleague pointed out that was not what I should be doing. I was co-founder of the company, so after I read what I should be doing (which is more like what you say), I appointed my right hand as CTO and I became head of our small R&D dep. That was excellent. Now i'm CTO again; older and wiser and I fit the role now, however, when we grow more that might change. I really do want to keep coding for fun and business.

agibsonccc 10y ago
CTO roles at companies vary. Some end up doing "technical stuff" as well as business. How large was your team that this was a problem?
- tluyben2 10y ago
  300something. I was too involved in the projects themselves (which is what I like(d)).
madaxe_again 10y ago
Yeah, my colleagues just found entertainment in watching me lose my wits (they're both stoics, very good at business but not big on the giving a damn scale, and I do worry about long term course in my absence, and think they may go steady-state from here in), and after I took some time out because I was on the brink of recklessness, suggested I leave the business. So I did. I'm pretty sure it's the right call for all concerned.