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Re:A CTO should be technical by dijit on Monday September 26, 2022 @05:07PM (#32988423)
I just became a CTO. So, let me bear my thoughts.

Since July of this year I've been CTO for a small games company, I've worked in this industry before in a more specialised role but this is much broader scope.

I've gone from being responsible for 1 person to 10 which will likely become 50 by the end of next year.

I'm terrified.

I'm terrified because I feel like I will let my reports down.

I'm terrified because a lot of the work I'm doing lacks transparency, how do I tell my compatriots about things that may not come to pass, especially deep political things -- and the amount of work necessary to onboard/offboard people, about "strategic partnerships" and why they're taken, or not taken or any of the hundreds of other things which are changing direction 3 times a day each.

I am technical, deeply, passionately technical.

I will not do service to people by being technical, my days are too fragmented, my worries too broad, it's impossible to dig into a small focused problem and give it the treatment it deserves - and even if I could then I'd be dooming one of my colleagues to maintain it forever because I couldn't possibly..

My being technical is good because I know the problems and I know what can make people feel valued; I can give people autonomy and direction and I can understand when help is needed and how to give it.

However, almost nothing in my work is technical, it's all presentations, discussions, breakdowns, timelines, contracts and negotiation.

The most code I write now is to do cost reporting.

My most frequently accessed cloud console pages are the billing sections.

This is not fun at all (and frankly, I didn't think it would be); but I fear what will replace me if I leave.

Re:A CTO should be technical by givemeethekeys on Monday September 26, 2022 @05:32PM (#32988788)
I've reported directly to good CTOs and really bad ones.

The shitty ones:

- Either never built trust or broke trust.

- Were impulsive and reactionary.

- Didn't rely on the expertise and skills of their reports as much as they told them what to do because they already knew everything. Didn't ask questions. Gave orders.

- Literally used the words, "because I said so".

- Believed that they were the only one doing any real work. Used the words, "easy" to describe work that was assigned to their reports.

- Were very insecure - questions were often received as challenges to authority.

- Set in place policies which they were the first to violate.

- Their actions and their words disagreed.

- Lost their best people within a year.

Re:A CTO should be technical by ctothrowaway8 on Monday September 26, 2022 @10:59PM (#32991143)
This comment may have been the tipping point into seriously considering quitting. Deep down I already felt it coming on but seeing it laid out like this hit home. The person currently in that leadership position fits every one of these bullet points and somehow remains in that position.

All their direct reports just seem to accept this lot in life, everyone else does their best to avoid drawing their ire. I imagine that maybe something will happen and they will get the picture and actually grow as a leader. It's growing old though and I miss being on a team wherein this wasn't the day to day morale.

Maybe they'll read this. Maybe it's you. Please take this seriously. You could do better.

Re:A CTO should be technical by jasonm23 on Tuesday September 27, 2022 @02:41AM (#32992162)
Sounds like me 10 years ago, and I wish I took this advice.

If you love technical work, QUIT being an exec, a VP, a manager... do the work.

You WILL have a crazy time getting back into tech work, after 10 years, even if you were hands on the whole time.

Management / CTO and everything in between is best served by people who are technical, and are ready/aware/willing to move into a deeply political and financial driven domain.

I hated it, but it took me a years to really let that sink in and feel it hurting me.

If you can short circuit that wasted time. Do.

Re:A CTO should be technical by jon-wood on Tuesday September 27, 2022 @05:15AM (#32993109)
Absolutely agreed. I'm currently working my notice after 5 years of technical leadership, after which I've got a job lined up where I can get back to sitting down and writing code. The last few years have been great experience, and I have no doubt they'll make it easier to work with management types in the future through understanding the sort of decisions they're having to make, but I have no desire to play politics for the rest of my life while other people go and do the bits that motivate me to get out of bed in the morning.
Re:A CTO should be technical by johnnymorgan on Tuesday September 27, 2022 @08:23AM (#32994440)
I'm a sysadmin background, did CTO for 9 years and then moved to product afterwards from the knowledge I gained.

Being on the other side of the fence has really helped me move around, I still to sysadmin/DevOps type work but mostly moved into product and I've found it really helps.

Too many C level see product as only UI/UX and the teams I manage appreciate my understanding of the pain points for everyone

Re:A CTO should be technical by theteapot on Tuesday September 27, 2022 @02:20AM (#32992047)
> Maybe they'll read this.

Be proactive, send them a link.

Re:A CTO should be technical by bruce511 on Tuesday September 27, 2022 @12:44AM (#32991622)
Interestingly this list covers "bad manager skills". Which emphasises the point that bad managers are bad.

Equally a good manager with average tech skills can do everything opposite to this list with the help of technical advice.

Sure we'd all like a great tech guy who somehow is also a fantastic manager. But let's accept those are rare.

Next best is a great manager (emphasis on good, not bad) who listens well and takes advice regarding pure tech matters. Over time their tech will improve (remember, good manager) but in the meantime IT flourishes.

Only then comes a great tech guy with poor management skills. Frankly poor management will kill a team faster than good tech skills can save it.

So yeah, as the article suggests, a great all rounder would be the best option. But I feel there aren't enough of those to go around. In that case I'll take a good manager over a good techie all day long.

Re:A CTO should be technical by colechristensen on Monday September 26, 2022 @06:16PM (#32989315)
The challenge in technical leadership is letting go of the specifics and delegating them and only in very rare specific circumstances issuing orders.

There are a lot of "person who did everything" types who end up in leadership positions who try very hard to continue doing everything of any importance instead of appropriate delegation and leadership instead of control. I've had that problem, it's hard to let go.

Re:A CTO should be technical by ajmurmann on Monday September 26, 2022 @10:15PM (#32990931)
This is such a good point. And doing this right can result in the technical leader feeling like they aren't providing value, especially if they are used to being great at solving technical problems themselves in the past. The manager dopamine loop is much longer and can at times not exist at all and you are still doing it right. I can see that it might be very tempting to try to get the feeling of accomplishment my stealing it from folks by disempowering them.
Re:A CTO should be technical by hef19898 on Tuesday September 27, 2022 @04:50AM (#32992957)
In defence of "because I say so", it sometimes necessary. And not a big deal in my book, if the person giving the order is also owning all the outcomes, good and bad.

Fully agree on everything else. Additional caveat, I have a supply chain and logistics ops background, so a completely different environment to design and development.

Re:A CTO should be technical by jon-wood on Tuesday September 27, 2022 @05:13AM (#32993094)
"Because I say so" is a terrible way to communicate why a thing is being done. In senior positions it is definitely necessary now and again to pull rank and tell people something is being done despite their protests, but I don't think I've ever found a situation where I couldn't articulate why that decision had been made. People may disagree with that decision, hell, sometimes I've disagreed with the decision I'm communicating, but you owe it to your people to communicate the reasons.
Re:A CTO should be technical by bluefirebrand on Tuesday September 27, 2022 @10:13AM (#32995466)
I had a situation recently where I had a report argue with me constantly over team agreement stuff like code standards and unit test coverage.

I explained every piece of rationale I could come up with for why the team chose to do things the way they did. I offered to schedule team discussions for her to try and convince the team to adopt other strategies, with the understanding that if the team didn't want to do things her way that would be the end of the discussion.

It wasn't the end of the discussion for her though, she kept complaining. Eventually I just had to say "that's the way we do things here so you have to get on board". It's awfully close to "because I said so", and I hated saying it, but I exhausted every other avenue I could think of.

She wound up giving her notice, so I guess we were on the same page because I was working with my manager on letting her go. But if she had been able to keep her head down and do the work we would have kept her for sure. She was a good coder, good systems knowledge, just really didn't like writing unit tests I guess.

Re:A CTO should be technical by mfuzzey on Tuesday September 27, 2022 @03:36PM (#33000066)
Yes but you already gave plenty of reasons before resorting to "that's the way we do things". And I think that's fine. What wouldn't have been fine would have been to skip the explanations.

Most people, given explanations, will accept them even if they don't agree with them. And quite often they will realize that there is more to the issue than they originally thought.

Re:A CTO should be technical by hef19898 on Tuesday September 27, 2022 @07:50AM (#32994136)
Fully agree on giving reasons. And more often than not there is room to discuss them. Also, from time to time, it doesn't matter weather or not we agree with those. And then there are those moments were there is no time to discuss.

Good leaders know to tell those appart, and professionals can accept it. Unfortunately, this combination, good leaders being in charge of professionals, is rarer then I'd prefer.

Re:A CTO should be technical by johnnymorgan on Tuesday September 27, 2022 @08:26AM (#32994462)
Too rare but when you get it, it's gold baby
Re:A CTO should be technical by hef19898 on Tuesday September 27, 2022 @01:32PM (#32998436)
Solid, 24 carat gold.
Re:A CTO should be technical by 29athrowaway on Tuesday September 27, 2022 @12:53AM (#32991658)
Because bad organizations conflate leadership and dominance.

Raw dominance is the dynamic governing primitive social animals.

Chimps are a bit smarter, and would collaborate as a group to beat up alphas that they hate.

Re:A CTO should be technical by nix23 on Tuesday September 27, 2022 @05:32AM (#32993215)
Fun fact, there are nearly no Animals who life in groups with "real" alphas, especially not Wolfs, maybe you can say Elephants where the oldest (most of the time) female is the leader (however that is because she is the most knowledgeable (location of waterholes, food etc)) and not because of her Character or "i want to be a leader" mindset.

There is one exception that comes to my mind with "real" Alphas and those are Gorillas.

Re:A CTO should be technical by jasonm23 on Tuesday September 27, 2022 @02:43AM (#32992174)
Let me rephrase that.

The group is smarter, than an individual's dominant strategy.

They'll collaborate as a group to embarrass and undermine and quit that scene.

Re:A CTO should be technical by samhuk on Tuesday September 27, 2022 @06:09AM (#32993442)
Adding to that list, and somewhat related to your first point: Never built anything technical of any quality.

A coach that never played can't teach.

Re:A CTO should be technical by ambicapter on Tuesday September 27, 2022 @06:31AM (#32993567)
Hard disagree. A good coach only needs to see the players on the field, notice the things that wins game, and figure out the way to motivate their players. Don't need to have played the game, though it helps. I'm thinking of one of the best coaches in the world, who played the sport at an unimpressive level as a teen...but at a young age he watched his father work as an assistant coach. That's where he learned his skills.

As well, the requirement for "must hit X bar of quality", where X is some arbitrarily high level, is nonsensical. If they're so good at building quality products...then why aren't they doing that in the first place. Necessarily, your best builders should be builders, and your best managers...should be managers.

Re:A CTO should be technical by samhuk on Wednesday September 28, 2022 @04:56AM (#33005857)
> notice the things that wins game

> motivate their players

These are made so much easier if you have "played the game" that you pretty much end up back to the original argument of it being a requirement if being "a coach" to remain competitive. There of course will be outliers to this, like your aforementioned "coach that never played", but why deliberately base your point on an outlier?

> "must hit X bar of quality", where X is some arbitrarily high level

Quoting myself, I said "of quality", i.e. something that is reputable and, relative to some reasonable and well-known industry standard software development principles and benchmarks, of quality. I wouldn't say it's totally arbitrary.

Re:A CTO should be technical by wpietri on Monday September 26, 2022 @05:27PM (#32988697)
> I fear what will replace me if I leave.

Right? I've had this conversation with so many techies-turned-leaders. The way I look at it, managing means I've given up my chance at doing the fun work so I can create a context where other people can get shit done in a way that's effective and rewarding.

That does require being very technical, because you have to have a feel for the work and the issues. But it also requires giving up being very technical, because you just don't have the time or the headspace to get lost in a good problem.

It's a conundrum, and it's why Charity Majors' "Engineer/Manager Pendulum" resonates for me: https://charity.wtf/2017/05/11/the-engineer-manager-pendulum...

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @05:33PM (#32988809)
I was a CTO once.

Transparency is not your job. You're job is to keep telling your reports that everything is on track no matter what everything else is just "rumors". If you don't they will start getting anxiety or looking for new jobs instead of pressing on. This could actually be the difference between what makes things fail or succeed. You're job is not to be transparent or honest. Its to make sure everyone stays productive and on track. This will 100% require lying or being non-transparent at some point.

>My most frequently accessed cloud console pages are the billing sections.

Lol yep.

Eventually some of those reports will hate you as well even if you do everything perfectly. Its inevitable from being in charge. You may not find out till running into them years later and they just shrug you off when you try to say hi.

I think I was good at the job, though of course I'm biased but even looking back there are very few things I would change. I really did try and will never feel like I was inadequate even though the company eventually did go under due to bad investments the owner made.

Re:A CTO should be technical by capableweb on Monday September 26, 2022 @05:46PM (#32988968)
> Transparency is not your job.

> You're job is to keep telling your reports that everything is on track no matter what

> This will 100% require lying or being non-transparent at some point.

Following this advice is another way of loosing employees, at least I'd leave a company quickly if the CTO started lying about potential problems not being problems.

In the end, depends on the company. Usually the company I've worked in, have valued transparency, so employees can decide themselves if they want to continue working there or not, when there are potential issues.

Not sure who it'll be good for if things are delayed in a project, you might be able to ship a good product but then the executive team is all like "Noooo, what you're hearing is just rumors, everything is fine and all will be good when we release".

Re:A CTO should be technical by NegativeLatency on Monday September 26, 2022 @06:04PM (#32989166)
> I'd leave a company quickly if the CTO started lying about potential problems not being problems

Absolutely. In the case of someone saying a clear problem is not a problem, we have a few cases:

The first, they're lying to me, in that case they're dishonest and I dont want to work there, they're probably just covering it up to make some money and then move on when things fall apart.

The second, they're incompetent and actually don't realize it's a problem, why would I want to work for someone who's bad at their job.

Probably others but I can't think of them

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @06:35PM (#32989504)
>all will be good when we release

Well I've literally been in the position where this was true to close a deal so we could stay in business. What would be the best option in your opinion? Risk a critical person leaving right then and loosing the customer and then losing everyone job? Or lying and telling them we are all ok just keep on doing your job and don't listen to rumors?

You are espousing false virtue/armchair quarterback. Real life is complex and lying can save many people jobs.

Re:A CTO should be technical by warent on Monday September 26, 2022 @07:01PM (#32989737)
"Things are tough right now, but once we close this deal then we'll be in a much more comfortable position. Your role on this is critical to our success."

Is this not a reasonable way of approaching it? It seems to be simultaneously honest and empowering. What lie is necessary?

EDIT: slight revision

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @12:27PM (#32997554)
I wasn't trying to write a business book but what you wrote is fine usually for the senior level employees that get how business works and probably took the job with the understanding of the weight of their position. However you will also have fickle entry/low/mid level employees that don't have the maturity to accept the realities of the business world.
Re:A CTO should be technical by random314 on Tuesday September 27, 2022 @01:47PM (#32998644)
> However you will also have fickle entry/low/mid level employees

You need to read that sentence again. Your comments are very revealing about you and not about CTO level work as you are imagining.

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @05:10PM (#33001166)
My comments are very revealing about the reality of the work world at mediocre aka most companies.

If you get a big enough group of people there are going to be some people with machiavellian tendencies or at least some that read bad advice on the internet about how to get ahead at work and try to apply it with clumsy gusto. You will look like a real fool to your boss the CEO if you are giving information to these type of people and they try to use it for their benefit.

I may be painting too dark a picture due to the focus the comments have on a single sentence. Overall I had good relationships with the vast majority of people that worked for me. I know this because I still have contact with most of them even though we have almost no chance of ever working together again. You are deluding yourself if you think there are no bad apples out there or that people having problems in their personal life may try to pull manipulation at work to get ahead or however they see may solve their problems.

Re:A CTO should be technical by random314 on Tuesday September 27, 2022 @08:38PM (#33002982)
> You are deluding yourself if you think there are no bad apples out ther

Please don't put words into my mouth.

Re:A CTO should be technical by random314 on Monday September 26, 2022 @08:19PM (#32990334)
Compulsive liars cannot change their habits.
Re:A CTO should be technical by sahila on Tuesday September 27, 2022 @03:46AM (#32992591)
And gasp you may have to reward your worker because they truly are that valuable instead of reaping all the benefit for the cto.
Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @05:19PM (#33001266)
Thats mostly a CEO trait. Remember CTO,CFO,COO,CIO, ect are all just jobs. You ultimately report to the CEO, whom ultimately reports to the investors,stakeholders, capital partners, b2b relationships and so on.

For the record I gave 100% of bonuses I had awarded to my staff and 0% to myself the entire tenure.

Re:A CTO should be technical by random314 on Tuesday September 27, 2022 @08:39PM (#33002989)
Who awards bonuses to themselves?!
Re:A CTO should be technical by kelnos on Monday September 26, 2022 @07:48PM (#32990118)
> You are espousing false virtue/armchair quarterback. Real life is complex and lying can save many people jobs.

I'd rather my job disappear than still be there because someone with employment power over me lied to me. This isn't false virtue or armchair anything. No exceptions, or I don't work with you ever again. It's not hard. Learn to communicate effectively, and learn to treat your employees with the respect they deserve.

Re:A CTO should be technical by skipidarink on Monday September 26, 2022 @09:07PM (#32990588)
Consider that you're advertising yourself as the type of person who absolutely must be lied to in order to maintain morale.

I've been close to situations where the ICs did their absolute best and it was a total waste because of politics outside of their control. Do you tell them that so-and-so highly-respected person was shit-talking them because of an unrelated agenda and invalidated all of their work? Or do you tell them good job (it was a good job) and not get into it?

Re:A CTO should be technical by comex on Monday September 26, 2022 @11:37PM (#32991324)
> Or do you tell them good job (it was a good job) and not get into it?

Personally, I’m okay with not being informed about everything that’s going on. I work at a big enough company that I couldn’t possibly know what goes on all the way up the management chain, but even if I worked at a small startup, I could understand if management didn’t want to be fully transparent. I don’t need to know; it’s none of my business. But I won’t stand being lied to – even about small things, or things I don’t even care about in their own right. I see lies as a breach of trust and as a sign that I can’t trust that person, moving forward.

So it depends on what you mean by “not get into it”. If you really stick to truthful statements, and if there isn’t a high enough prior expectation of transparency to make it amount to a lie of omission, then leaving it at “good job” is perfectly fine. But if you do lie… well, if I find out, I’m probably leaving.

Re:A CTO should be technical by warent on Monday September 26, 2022 @09:16PM (#32990642)
Frankly if this actually happened, I would do neither. Just tell my IC "I'm not sure why your work was invalidated. Let me look into it for you." and then address this as a grievous issue on behalf of my IC with the leadership.

If leadership doesn't fix the problem then just resign in protest.

EDIT: It's now occurring to me that there's probably different schools of thought here. Yes, I've resigned in protest on behalf of my workers before.

If my team is getting fucked, then I've either failed my team, or my purpose is meaningless. Either way, get me out.

Re:A CTO should be technical by skipidarink on Monday September 26, 2022 @10:10PM (#32990905)
> Just tell my IC "I'm not sure why your work was invalidated. Let me look into it for you."

And so you take your first step down the path.. "I'm not sure" is a lie here.

Re:A CTO should be technical by warent on Monday September 26, 2022 @10:22PM (#32990973)
Why do post mortems happen for production issues, when you could just open up "git blame?"

Are you lying to the team when you say, "we're not sure how this happened" rather than just quoting the git blame?

Well, no. The problem is much more complicated than a buggy commit. It's a wider problem with the system. So you say "we don't know, we have to look more into it" and do a post mortem because that is the honest truth.

The same principle applies here. So-and-so highly respected person committed a real-life communication bug that got merged into this IC's production career. But the problem is much more complicated than that. You don't know what the actual problem is until you address it with the leadership team.

Re:A CTO should be technical by skipidarink on Monday September 26, 2022 @10:32PM (#32991011)
I hear you on all of that, I'm just saying that leadership gets complicated. Sometimes the lie is better for all involved, especially the IC. You recognized this with your first instinct on how to communicate it.

As far as the rewards for poorly-motivated actions, we've always got the long term.

Re:A CTO should be technical by light_hue_1 on Monday September 26, 2022 @11:29PM (#32991282)
> Well I've literally been in the position where this was true to close a deal so we could stay in business. What would be the best option in your opinion? Risk a critical person leaving right then and loosing the customer and then losing everyone job? Or lying and telling them we are all ok just keep on doing your job and don't listen to rumors?

Well I've literally been in this position too.

Lying to people is ineffective. It literally leads to the rumors you want to avoid. And even if your lies pay off, people aren't dumb. They realize how close to the edge they were and that you are a liar. Next time it will just be worse!

It's much better to be honest. Explain the situation. Explain what it will take. Use it to motivate people and build them up. People love a challenge, they want to feel like they're the hero of a story.

You literally took a situation where your employees would have come out stronger and more motivated to work for you, and you turned it into one where they walked away with mistrust.

> You are espousing false virtue/armchair quarterback. Real life is complex and lying can save many people jobs.

It has nothing to do with virtue! Even if you don't give a damn about being a good human being, this is a terrible way to manage people.

Re:A CTO should be technical by Nuzzerino on Monday September 26, 2022 @06:58PM (#32989714)
In real life, some people are human lie detectors, or at least better at detecting lies than you are a liar.

But I can acknowledge there are cases where transparency is simply not an option.

Re:A CTO should be technical by kelnos on Monday September 26, 2022 @07:43PM (#32990079)
> Transparency is not your job. You're job is to keep telling your reports that everything is on track no matter what everything else is just "rumors". If you don't they will start getting anxiety or looking for new jobs instead of pressing on.

Gross. I worked at at company where the CEO and CTO were hiding important things about the company from employees. When we found out, we felt lied to and betrayed, and there was a mass exodus. The company folded less than a year later.

I'm not saying leadership should be telling employees every little tiny thing. (And certainly some things just cannot be talked about in early stages of the deal, like funding rounds and being acquired.) But employees should have a pretty good handle on the health of the company and what's going on at a high level.

If employees get anxiety or start looking for new jobs because the executive team is being truthful, then either a) the company is doomed, and only an asshole executive would lie to keep employees around, or b) the company is just in a difficult spot, but leadership is not doing a good job of communicating the solid, likely-to-succeed plans in place to get things back on track.

I refuse to work for leadership teams who are not transparent. If they don't think they can trust me to act well in the face of difficult information, then I don't see why I should trust them to run the company that's responsible for my paycheck and livelihood.

Re:A CTO should be technical by warent on Monday September 26, 2022 @05:49PM (#32989006)
> Transparency is not your job.

> You're job is to keep telling your reports that everything is on track no matter what

> This will 100% require lying or being non-transparent at some point.

I've only been performing roles of director / vp to small/mid size companies so far, so maybe there's some secret CTO sauce I'm still missing.

To me this advice seems toxic and destructive. Vent upwards, yes. Manage expectations, yes. But you're hiring brilliant people who will eventually know when youre lying or concealing info from lack of trust. good luck with loyalty at that point.

Re:A CTO should be technical by 0x457 on Monday September 26, 2022 @08:28PM (#32990376)
There is only so much you can hide. Do you have BI? Well, they know numbers better than you, guess what? They talk to the rest of the company.

Do you have metrics available somewhere? Doesn't matter real-time or N days report - people can connect the dots: signs up are flat, but we keep hiring.

You can't meet requirements without marketing pushes? Well, shit, I wonder if a company spends 2 dollars to earn 1 dollar.

You can lie and bullshit all you want, but your reports and their reports will know.

I worked in a company where the analytics team suddenly decided to leave, all within days of each other. Month later - layoff. They weren't told that things are bad, they were the one who told you that things are bad.

Re:A CTO should be technical by random314 on Monday September 26, 2022 @06:02PM (#32989147)
Exactly what I thought. This is a view of employees as mindless drones whose only function is to make themselves busy. A very toxic management style. The advice that it is ok to be hated dogs the ditch further.

This is also an implicit permission to the employees to lie to the CTO. This is pretty standard narcissistic behavior, where your lies to employees are just doing business, while employees lying to the management is a grave offence that calls for job termination.

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @06:55PM (#32989691)
>employees as mindless drones ... very toxic management style.

I agree.

Re:A CTO should be technical by random314 on Monday September 26, 2022 @10:42PM (#32991054)
Did you just agree that you are a toxic manager?
Re:A CTO should be technical by stormbrew on Monday September 26, 2022 @05:48PM (#32988990)
> You're job is to keep telling your reports that everything is on track no matter what everything else is just "rumors".

Sometimes your employees can tell things aren't going well, and you bald face lying to them like this will make them leave even faster.

This is also a great strategy to fuck people over, where if they believe in the stability of the company right until the day layoffs are announced they might have just bought a house or something else that will make the next few months for them excruciating, if not disastrous.

So please don't take this advice to the extreme imo. I'm not saying you shouldn't be positive, or give every detail. But you should be realistic. Save the rose tint for the investors and just make sure people have what they need to do their best work, within your power.

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @06:13PM (#32989279)
I actually wrote several responses and realized I was rambling on because of just how difficult it is to explain the reality of being in a decision making role. Rumors and politics are far far more prevalent than any acutal problems that will affect your people.

It is not your job to be responsible for other peoples personal lives, you are not the messiah. All you can do is fight to get them the pay they deserve. What they do with the money you have no control over anyway.

Layoffs at non Fortune 500 companies generally have less warning than anything can be done about anyway. Sure if its budgeted at Pfizer 6mo in advance your an ahole for not telling people. However its usually more like 2-4 weeks that the people in charge even know beforehand. ALso remenber we are talking about CTO. Its the CFO that knows the truth about the finances and may be hiding it from you as the CTO.

Re:A CTO should be technical by warent on Monday September 26, 2022 @06:49PM (#32989631)
There seems to be quite a lot wrong in this post in my humble opinion... In brief, this reads as:

  * Allowing rumor/politics to become malignant through deceit rather than healing through truth
  * Dismissing responsibility for other people's livelihood because "hey its not my fault they didn't save money in case I throw them in the guillotine"
  * Using lack of information as a reason to lie, rather than just telling your workers that you don't know the answers.
These are definitely the antithesis of "good" leadership. "Good" from an empathetic, humane perspective, and "good" for business and profit. It's true we have to make unpopular, hard, sad decisions. Yet it is absolutely imperative that we remain mindful and diligent to our team as individual humans.
Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @07:31PM (#32989984)
You are ignoring a hard reality. Other people probably want your job. If you look weak/uncertain/outofloop it will encourage them to come after you and give them ammo against you. Making your job at best more difficult or at worst a full blown power struggle.

Sorry but the reality of human nature is tough.

Re:A CTO should be technical by kelnos on Monday September 26, 2022 @09:17PM (#32990648)
If you truly think that a person can't be honest and trustworthy, while simultaneously being strong and confident, then I really don't know what to tell you. Disclosing hard truths doesn't mean being "weak and uncertain".

I know workplaces aren't democracies, but there's no question that I'd vote for the straight shooter (even if their own position in the company is weakened by that trait) over someone who plays the political game well but lies to their reports.

Hell, I would vote, with my feet, if I had to.

Re:A CTO should be technical by warent on Monday September 26, 2022 @07:45PM (#32990098)
That is certainly one way to operate in the world! It is just not how my world works though.

If someone is actually better suited for a role than I am, then let them have it. I'll find another role and keep growing. Where is the problem?

If some team makes the mistake of confusing trust and openness with weakness, then good riddance, I'm better off with a different team.

Re:A CTO should be technical by my_usernam3 on Monday September 26, 2022 @07:38PM (#32990047)
> All you can do is fight to get them the pay they deserve

You can also be honest with them so that they can make informed decisions for themselves. The best CTOs I've worked for have been honest people who give you the bad and the good news together.

> However its usually more like 2-4 weeks that the people in charge even know beforehand

I'm guessing you're not referring to public companies with significant revenue. There's almost always warnings well before the 2 week mark.

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @07:45PM (#32990093)
>I'm guessing you're not referring to public companies with significant revenue

>Layoffs at non Fortune 500

Yeah Literally what I said in my comment.

Re:A CTO should be technical by kelnos on Monday September 26, 2022 @09:16PM (#32990640)
"Non Fortune 500" != "non-public companies"

There are many public companies not in the F500, and I agree with the grandparent that every executive will either know, or have a really good idea that a layoff is coming, well before 2-4 weeks prior, even if the internal finance/HR process hasn't quietly, officially started yet.

Re:A CTO should be technical by jklp on Monday September 26, 2022 @07:31PM (#32989990)
I see a lot of responses to this comment, especially these lines:

> Transparency is not your job.

> You're job is to keep telling your reports that everything is on track no matter what

> This will 100% require lying or being non-transparent at some point.

To add my 2 cents I kind of agree. When I first got into management, I didn't realise how many fires they were, or priorities I needed to balance. Initially I thought "there shouldn't be this many fires" but I soon realised that that was my job, to put them out, escalate when required, etc all while making sure the ship is steady and doing it with a smile on my face.

Some examples include:

- News that a sales person has sold a huge project which will save the company, but we can't deliver or build with our current backlog / resources

- One key team member has been taking a lot of doctor's appointments recently - and suspect they might be quitting / job hunting

- There's a very obscure security issue which could be fatal if discovered, but is a huge task which will disrupt a project which is already delayed and over budget

If I ran into any of these when I first started I would have freaked out - and that would have disrupt my team as they couldn't be productive with that anxiety over their heads.

Instead I just had to be confident that I could put out those fires, or put in place strategies to mitigate them, and let the team know it's all under control.

Of course if something was too big to handle I'd escalate, or if something blew up I'd take responsibility etc - but I think job #1 in management is to shield the team from distractions and let them do what they're best at doing.

Re:A CTO should be technical by kelnos on Monday September 26, 2022 @09:08PM (#32990603)
I hope that's what the original poster who you quoted meant, because I don't see all that much wrong with the examples you mention. No, there's no need to engage people in discussions about things if it doesn't really impact them, or they can't really jump in and help the situation.

However, in the absence of some legal requirement to keep quiet, if some employee got wind of one of those situations, and came to you and asked you about it, I really do hope you'd be honest and forthcoming. Because otherwise I think that's when you'd cross the line (for me at least) into being untrustworthy.

One thing to mention though: in the case of your first example, if that huge deal really is going to fall through, no question, and the company is going to fail because of that, no question, I would lose all respect for an executive who didn't pro-actively have the hard talk with employees about that situation. Yes, some people will leave. But that's life, and your employees have entrusted their livelihood with you; you owe them that level of honesty.

> I just had to be confident that I could put out those fires, or put in place strategies to mitigate them, and let the team know it's all under control.

Which is fine! Because if you truly did put out those fires, or at least put in place some mitigating strategies, then you were absolutely telling the truth that it was under control.

> I think job #1 in management is to shield the team from distractions

The difference is that some "distractions" can have a material impact on those employees' lives. An executive who hides those things and lies about them to employees is not worthy of respect. For "distractions" that truly are just distractions, sure, fine, no need to broadcast.

But I think a key question is: if a bit of news could make a reasonable employee, thinking logically about the news, decide to quit, then... you absolutely should be disclosing that news. Anything else is just a betrayal of the implicit trust an employee must have in their employer.

And yes, I know all this might seem pretty idealized, and I know there are a lot of companies and executives who won't get these things right. But that doesn't mean I want to work for those people.

Re:A CTO should be technical by jklp on Monday September 26, 2022 @09:36PM (#32990752)
Yeah for sure completely agree. Tbh I didn't think too deeply about the scenarios, they were more to put context around what I meant by "fires", and how not mentioning them (which some might consider lying) is necessary sometimes to steady the ship (though if a team member asked I'd let them know what's happening).

I do think scenario #1 is interesting to talk about though.

I.e. If I was that manager receiving that news, I wouldn't outright tell the devs and say "it could be crunch time for the next 6 months", which might cause a panic and devs will start looking for other jobs.

Instead I'd call a meeting with leadership / sales, see what was sold and if there's any flexibility on deliverables with the client. If we need more resource, is it worth finding funding to hire more staff, or maybe postpone another project to get this higher priority one done.

Once that's resolved then I can think about delivering the news. Maybe it's a non issue (e.g. a new team is spun up to handle the project and someone gets a promotion to head the team), maybe it's crunch time (in that case it's time to have a difficult conversation with the team), or maybe the client is flexible on delivery (so it's business as usual).

Again, I could see how some managers would be uncomfortable not telling their team everything (and potentially cause unnecessary panic) - but I think that's part of management, knowing what level of detail your team are happy with, knowing what you can / cannot handle, and knowing how to delivery good / bad news and sometimes having to be the bad guy.

Re:A CTO should be technical by light_hue_1 on Monday September 26, 2022 @11:36PM (#32991314)
I would add including the team once the path is clear.

What scares people is uncertainty. Not uncertainty of outcome (50% chance this will save us). It's uncertainty of what the options are, what the roadmap might be. That's the job of a good manager. Insulate the team from uncertainty and politics. Figure out the space of options, what the outcomes can be, negotiate it with leadership, and present a reasonable and clear plan to the team. That won't cause panic.

Show the team the plan, its rationale, and what needs to be done. What the upside will be. Let them take ownership of it. Let them make the lower-level decisions of how to split time, of what to prioritize, of what edges can be cut. With your feedback.

People generally don't bail when faced with a challenge. They like challenges. You just need to define the challenge clearly and set the path for overcoming it.

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @11:18AM (#32996456)
>I hope that's what the original poster who you quoted meant

Yes I did for the most part. I was replying to another persons wording though so many people have gotten out their pitchforks.

Re:A CTO should be technical by drc500free on Monday September 26, 2022 @08:09PM (#32990266)
At this point in my career, I think the #1 responsibility for everyone above VP is to maintain everyone's fantasy of a stable paycheck in exchange for stable work.

Once you peek behind the curtain of where your firm's cash comes from and where it goes, you have to live with a deep existential fear that you could mess up a bunch of people's lives... and you don't want others to have to live with that.

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @11:23AM (#32996545)
Finally someone that seems to actually have some real life mgmt experience replying.
Re:A CTO should be technical by stormbrew on Tuesday September 27, 2022 @12:12PM (#32997326)
It's very convenient to believe that everyone replying to you who disagrees with you has no management experience, and the one lone voice giving uncritical agreement is the one person who does.
Re:A CTO should be technical by pvorb on Monday September 26, 2022 @05:59PM (#32989116)
> Eventually some of those reports will hate you as well even if you do everything perfectly. Its inevitable from being in charge. You may not find out till running into them years later and they just shrug you off when you try to say hi.

Maybe they simply found out that you kept lying to them?

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @06:15PM (#32989302)
That was not the reason.

I know its hard to understand if you are never in such a role. People can be very irrational and will look to blame someone in charge when bad things happen. Even if they are the cause of those bad things.

I had one guy that got obsessed with crypto and was doing crypto trading instead of his work, not showing up/logging in, not making deadlines. He went off on me for like 30 min when I fired him and never spoke to me again despite warnings and discussions about the problem before getting fired for one example. In his irrational opinion I was holding him back from getting rich by expecting him to do his job.

Re:A CTO should be technical by squeaky-clean on Monday September 26, 2022 @06:59PM (#32989723)
I've been on the reverse side, where it was obvious the CTO and CEO were hiding things. It's annoying for a while and then eventually there's some proverbial straw that breaks the camels back.

Word spread pretty quickly through various cliques in the company. Some teams had no idea what was happening, other teams lost literally all their developers and and couple managers over the course of 30 days.

During my exit interview I mentioned the dishonesty and they just doubled down that I was imagining it.

Re:A CTO should be technical by kelnos on Monday September 26, 2022 @09:28PM (#32990714)
> I had one guy that got obsessed with crypto and was doing crypto trading instead of his work...

I think we are all very obviously not at all talking about the kind of situation you describe.

I left a company a little over a decade ago where the CEO and CTO (both co-founders) were lying to us about the company's situation for the better part of a year (which was longer than half the company had been employed there). I fortunately haven't had the chance to run into them since then, but I would absolutely give them the cold shoulder if I did. And that's because of what they did. I put in 80-hour weeks (including many weekends)[0] for over a year at that place, and they repaid me with a middling salary and worthless equity (after all common stock got wiped out less than a year later when the company got sold to one of the investors for peanuts and scraps).

Anyway, the one "nice" thing I can say about that CTO is that after they had a layoff (half the company), and I didn't get laid off, I went to the CTO and volunteered, and he let me go with the 4-week layoff severance package, which gave me a much-needed month off while I found another job.

(Speaking of startup equity, I'm just glad I wasn't quite out of college during the original dot-com crash, when colleagues I would meet a few years later ended up underwater on the loans they were encouraged to take out in order to exercise their company stock options. I can totally imagine wide-eyed 22-year-old me falling for a garbage scheme like that.)

> People can be very irrational and will look to blame someone in charge when bad things happen.

And sometimes blaming the person in charge is correct and rational.

[0] All stuff I will never again do for any company after that experience...

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @11:31AM (#32996648)
>I think we are all very obviously not at all talking about the kind of situation you describe.

Not really. My words were some people will hate you even if you do everything right. This was an example of a situation that was handled right but the person ended up hating me and slandering me for years afterwards. Just because I would not allow the company to fund their get rich quick scheme instead of their job.

I've even found people that I did not manage that got fired blamed me sometimes. Like all of mgmt was some evil cabal that conspired together to fire them cause thats what we really want instead of making the company money so we can all get out paychecks.

What people are doing is going off on a tangent of how they don't agree with how I handle the grey area stuff. There is a great deal of Silicon Valley worldview going on as well. The majority of the working world has lots of politics and pettiness going on along with power struggles and backstabbing. You cant be S.V. idealistic and keep your MGMT job in the middling business world.

Re:A CTO should be technical by my_usernam3 on Monday September 26, 2022 @07:40PM (#32990055)
> People can be very irrational and will look to blame someone in charge when bad things happen.

Isn't that what you did?

> Even though the company eventually did go under due to bad investments the owner made.

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @11:28AM (#32996615)
That was a factual statement, so no. I think I get the personal attack you are trying to make at me though.
Re:A CTO should be technical by colechristensen on Monday September 26, 2022 @06:03PM (#32989159)
>You're job is to keep telling your reports that everything is on track no matter what everything else is just "rumors".

When you've been lied to enough you stop believing the lies, a leader who can't be relied on to tell the truth unless it's positive might as well not say anything at all or be there in the first place. Having to doubt and read between the lines for each and every message from leadership is a waste of my time and leads directly to me A) no longer caring and B) not trusting my leadership.

This kind of manipulation only works on stupid or inexperienced people.

There is a big difference between putting a hopeful spin and always fighting for the best outcome and straight up saying everything is fine until there's nothing left but ashes.

Re:A CTO should be technical by baby on Monday September 26, 2022 @06:11PM (#32989264)
> Transparency is not your job

I would argue the opposite: transparency is one of the biggest part of your job. You're not in a leadership position, and it's your choice: do you want an opaque company where politics drive individual success? Or do you want a transparent company where employees respect their leaders and where the best insight wins?

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @06:17PM (#32989335)
Real life is not fair.

If the company initiative is to be transparent then sure you can be. However that is the vast minority of companies. Though people on HN may have a skew to thinking the opposite.

Re:A CTO should be technical by baby on Monday September 26, 2022 @10:20PM (#32990953)
I've actually quit jobs because of this, so your employees actually don't have to put with toxic management.
Re:A CTO should be technical by warent on Monday September 26, 2022 @06:28PM (#32989421)
Curious to know where the statement "real life is not fair" is coming from / what it's referring to.
Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @06:53PM (#32989671)
> do you want an opaque company where politics drive individual success >you want a transparent company where employees respect their leaders and where the best insight wins?

The comment I replied to has very startup company silicon valley skew to it naive of the majority of the world. Very few of us are in any position to determine or change the political/cultural/driving forces of a company we have to work at. Usually the best you can do is adapt to whatever is already there and try to make the best of it.

CTO is not a powerful position at most companies.

Re:A CTO should be technical by kelnos on Monday September 26, 2022 @09:36PM (#32990755)
> CTO is not a powerful position at most companies.

This I do agree with. Many CTOs don't actually have the entire engineering organization under them in the reporting chain (at a reasonably-mature company; not talking about a startup where the CTO is often one of the co-founders and runs engineering), so they have no real power to get other people to do what they think should be done.

At best they have an "Office of the CTO", or perhaps run the company's software architecture group (if the company even has one), and then they just have a tiny army of people who try their hardest to convince other teams to do things that aren't in their roadmap and would mean pissing off their bosses if they took them on. Not fun!

Re:A CTO should be technical by mianos on Monday September 26, 2022 @11:53PM (#32991399)
Yet in some companies, the CTO has the ear of the top executives. If some scheming non-technical career climber can get their way into the CTO's position, they can get to the top of the tree.

A lot can be achieved by aligning themselves with successful projects and crapping on others at the start or just at the cusp point of success or failure.

Re:A CTO should be technical by jcheng on Monday September 26, 2022 @07:03PM (#32989752)
What part of the world are you from?
Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @07:41PM (#32990063)
USA East coast.
Re:A CTO should be technical by random314 on Monday September 26, 2022 @08:10PM (#32990271)
Which company do you work for? I am making a list of companies to avoid.
Re:A CTO should be technical by random314 on Monday September 26, 2022 @06:03PM (#32989157)
> This will 100% require lying or being non-transparent at some point.

Are you ok with employees and reports reciprocating by lying to you as well.

Re:A CTO should be technical by citizenpaul on Monday September 26, 2022 @06:18PM (#32989340)
Yes. FYI They will lie to you regardless.
Re:A CTO should be technical by light_hue_1 on Monday September 26, 2022 @11:43PM (#32991354)
> Yes. FYI They will lie to you regardless.

If you create a culture where you lie, then people will lie to you.

If you create a culture where you are honest, people will be honest back to you.

There's nothing more powerful than going to your team and saying "Look, I fucked this up. I need your help". Honesty is disarming.

I'm in a field where I manage scientists. If people start to lie to me or even start to bend the truth a little, we will waste years chasing ghosts. The people that work for me are very savvy at figuring out what I think might be true and they can always present just the right data to make me happy. I had to learn early on that I need to be really explicit: we need to do good work, it doesn't matter if I'm right or wrong, it doesn't matter if they're right or wrong, all that matters is progress.

So no. Your employees don't need to lie to you. Mine come to me regularly and explain what went wrong. Judgement-free. And we do deep dives to prevent problems in the future.

You are causing the problems, not them.

Re:A CTO should be technical by tonyarkles on Tuesday September 27, 2022 @10:28PM (#33003615)
> So no. Your employees don't need to lie to you. Mine come to me regularly and explain what went wrong. Judgement-free. And we do deep dives to prevent problems in the future.

I had a junior EE come and find me while I was on a smoke break to immediately inform me that he had mixed up two connectors and had accidentally put 48V into a piece of kit that could only handle 12V, resulting in $10k worth of blue smoke. That’s what a high trust engineering org looks like. He could have lied about it, I didn’t see it happen, “I dunno I went to reboot it and it didn’t power back on”.

That’s what I want to see. He was open and honest with me because I don’t feed him bullshit.

Re:A CTO should be technical by random314 on Monday September 26, 2022 @08:16PM (#32990310)
My reports have lied to me very rarely, and I have never had to lie to my reports. For the reports that lied to me, I managed them out of my team irrespective of their work performance.

I have quit jobs where my manager lied to me. It is really really easy to tell when someone is lying.

You seem to live in some alternate dystopia where everyone lies to each other. How many of the companies that you have worked at have gone under?

Re:A CTO should be technical by kelnos on Monday September 26, 2022 @09:39PM (#32990768)
Yeah I'm really confused about this guy. I get that the world is not black and white, and conditions aren't always ideal... but I absolutely do not put up with the kind of dishonesty he's seemingly advocating. Perhaps not everyone has the luxury to be so picky, but... damn, I really have not gotten the impression (in my experience, and in the experience of friends and acquaintances) that this sort of bullshit is that common. At least not at successful, healthy companies.
Re:A CTO should be technical by matwood on Tuesday September 27, 2022 @06:34AM (#32993578)
> This will 100% require lying or being non-transparent at some point.

I've been CTO/equity partner/division director/tech lead/IC/etc... and this is terrible advice. The one thing you need as a leader is trust - your people need to trust you and you need to trust them. Treat people like the adults they are, tell them what's happening to the best of your ability, and people will work their asses off to accomplish the goal.

Re:A CTO should be technical by rektide on Monday September 26, 2022 @06:47PM (#32989610)
This is the job for 80% of corporations, the same 80% of corporations ruled by non-technical highly-political spin-based organizations, that dont really grok what they are up to.

Having technical depth in the leadership ranks, having real competency & belief & understanding in what you are doing, is, alas, not common. But wow, what a difference it makes for an org.

Re:A CTO should be technical by uvesten on Tuesday September 27, 2022 @06:12AM (#32993455)
I had a CTO like you once.

Totally destroyed morale, made the best people leave, and created a toxic work environment where there was no trust in management at all.

If that’s your goal, good work I guess.

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @11:43AM (#32996851)
>I had a CTO like you once.

Then you didn't have a CTO like me. I'm still in regular contact with most of the people that used to work for me. One actually just texted me this morning to ask how I was doing. Even though our lives will almost certainly never intersect again.

Re:A CTO should be technical by lawgimenez on Monday September 26, 2022 @08:42PM (#32990448)
Wow is this straight up lying though? When shit hits the fan, what is your plan B?
Re:A CTO should be technical by 29athrowaway on Tuesday September 27, 2022 @12:56AM (#32991670)
> "You're job"

I could not even finish reading this comment. As a C-level leader in an organization, communication should be your strong card. It's unacceptable that you don't even know the difference between "you are" and "your".

If as an employee I get an e-mail from a "CTO" consistently getting confused with such elementary, trivial shit, I would fucking resign immediately as that makes it evident that the organization is led by illiterate people and has absolutely no future.

Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @12:08PM (#32997235)
Good point, I agree.

I do know the difference though. I probably copy/pasted part of the comment around and missed that I changed the context. Shame on me for not proofreading my internet comment though. You should probably erase me from existence for my lack of vigilance as punishment...

Re:A CTO should be technical by 29athrowaway on Tuesday September 27, 2022 @01:47PM (#32998637)
Attention to detail is a big part of technical work.
Re:A CTO should be technical by danwee on Tuesday September 27, 2022 @05:45AM (#32993297)
I wouldn't judge so quickly, this kind of mistakes happen sometimes among non-native English speakers. In any case, CTOs don't do much, so the future of a company is not tied to the IQ of its CTO.
Re:A CTO should be technical by citizenpaul on Tuesday September 27, 2022 @12:09PM (#32997262)
You do a solid job of feigning niceties for someone that seems to hold themselves so highly.
Re:A CTO should be technical by fisherjeff on Monday September 26, 2022 @11:52PM (#32991391)
Sounds like you are making the technical to leadership transition extremely quickly. I think you will find that it’s the speed of that transition, rather than the transition itself, that is giving you difficulty.

One thing that has helped me, and may be helpful to you as well, is to look at your new role as an engineering problem. Logistics and process may not feel technical but they 100% are, and if you approach them with the same problem solving mindset and intellectual curiosity as, say, a coding task, you will enjoy them a lot more, and may even find that you become very successful at them.

Re:A CTO should be technical by spit2wind on Monday September 26, 2022 @05:50PM (#32989010)
Thank you for sharing how you feel. It's incredibly brave.

> I fear what will replace me if I leave

I admire the respect and dedication you have toward your reports (I assume the fear comes from what a successor may do to your reports rather than what a successor may do to the company).

However, if it falls on your to protect your reports from the company, then it may be worth considering how well the company's values align with your own. A terrible outcome would be to compromise your integrity for the sake of the company. If you leave, it's still possible to help those currently under you. Whether or not they would still want your help depends on your integrity.

Re:A CTO should be technical by ksec on Tuesday September 27, 2022 @07:11AM (#32993802)
I really like the model Apple are using is C grade only for CEO, Operation and Finance. The others are SVPs. There is no need for a CTO.

The first job of an SVP is to stand up to the CEOs when they are pushing for impossible deadlines.

The second job of the SVP is to stand up to CFO when they want layoffs. Or fight for more resources when they are pushed to the limit.

The third job, arguably the only thing that is technical, is to stop your sub coordinate pushing for what ever that is hyped in the industry to be used within your company.

It may sound easy in a small startup, doing the above three things in a large company is easily a full time job.

Re:A CTO should be technical by viridian on Tuesday September 27, 2022 @07:33AM (#32993972)
The biggest problem I've seen with this in implementation is that rolling the technical part of any organization under operations is usually disastrous, because ops will generally aim to keep their footprint as small as possible, and do the absolute bare minimum to try and retain talent. It's a model that heavily encourages thinking of technology as a cost center, developers (with domain knowledge) as easily swappable or replaceable units, and vendor SaaS as a preferred solution in almost every instance.

Personally I think having a CIO makes a lot of sense, even if you ditch the CTO, CISO, CDO, CAO panel that is generally subordinate to the CIO anyways.

Re:A CTO should be technical by throwawaymaths on Monday September 26, 2022 @08:27PM (#32990373)
You need to be technical enough to say no to a partnership, acquisition, or technical strategy that is bullshit. Most of the time, the Spidey sense to make that kind of a due dill judgement only comes through having been a technical employee. (Though having been a technical employee by no means guarantees that, either)
Re:A CTO should be technical by phphphphp on Monday September 26, 2022 @08:30PM (#32990390)
You’re leading with fear and anxiety, you’re letting that fear and anxiety trap you. There’s a great deal of value in thoughtfulness, in kindness, in using your passion to lead, but that value is often lost when the motivation for these behaviours is anxiety. A leader is as much what they signal as what they do.

There’s a variety of options available to you, options that can deliver the best outcome for the business, your reports and yourself — many of which can be fantastic outcomes for all.

Ultimately, building a business is a relay and you will at some point have to pass on the baton: if you fear that inevitability, that needs to be an immediate focus. What can you do to ensure that you can pass the baton on with confidence?

Positioning yourself as not “the CTO” but rather “the person establishing the business’ approach to technology” (which is achieved by utilising the CTO role today) can be a very powerful shift in attitude: you’re setting the technology organisation up for the baton to be handed over to the person ready to lead the next stage with confidence.

If I were in your position, I’d be talking with the other leadership in the business and clearly communicating that you don’t want this role indefinitely, I’d put a plan together for the next 12 - 18 months that involves bringing someone in to replace you, someone for you to pass the baton to.

A bad outcome for the business would be you spending the next 12 months silently stewing in your own anxiety and fear and then have a breakdown and disappear without any notice and the business is thrown into chaos.

As a leader, you don’t need to be perfect or a brilliant jack of all trades or a genius or even the smartest in the room, but you do need to operate with confidence though. If you don’t have confidence in something, focus on getting the confidence.

(For what it’s worth, the shift from where you are now to where you need to be is almost exclusively in attitude, it’s not some insurmountable challenge.)

Re:A CTO should be technical by definitelyhuman on Monday September 26, 2022 @08:42PM (#32990453)
If your org is 10 moving to 50 in a few months then you have a BIG change ahead. The good news is that you are responsible for how your team operates. You've identified problems, and now you get to fix them - not by coding, but through leadership & culture. This isn't to say it's easy, it's a massive challenge, but it is yours to solve and does require technical knowledge and skill.

No first time CTO's had it figured out either - continue to show the courage to ask advice (as you've done here) and figure it out bit by bit. Nobody has made your org before - there's no playbook only prior work.

The flip side is if that is of zero interest, you're likely in the wrong role. No shame, depends what motivates you.

Re:A CTO should be technical by xedrac on Monday September 26, 2022 @09:18PM (#32990655)
The worst CTO I ever worked for thought he was the expert because he "cut his teeth on assembly" in college. He indirectly micro-managed everyone with a "goal setting" farce. You had to submit very specific goals each quarter. He would then revise all of your goals for you, and give them back. They were a curated list of tasks that you had to accomplish. You would then be graded on those tasks and publicly shamed. He was so proud of his acronym "SPEED" and believed he was a great culture shaper. I've never worked in a more toxic environment, and never in a less productive one. We would have been 10x more productive if we didn't have a CTO at all.
Re:A CTO should be technical by baby on Monday September 26, 2022 @06:09PM (#32989231)
If I can give an advice quite different from the other comments: don't sweat it. You're not becoming responsible for the success of your team or your company, you're just taking a different role. Things would probably work fine without you. Hell, companies can run for months and years without CEOs (one of my previous company did).

What you can do is two fold: be technically involved (this is the topic of this thread) and be a good leader. The latter means a lot of things, but IMO it also means transparency. I'm really sad to see other comments saying that your role is to not be transparent, I totally disagree.

Re:A CTO should be technical by lawgimenez on Monday September 26, 2022 @08:39PM (#32990434)
Congratulations for becoming a CTO but also it terrifies me to think that my CTO is terrified of his/her work. Of course as IC I will never know this but I just don’t get it. I feel like CTOs has been in management jobs at some point before becoming part of the Cs. I feel like in your narration you went from IC to CTO directly. I may be wrong.
Re:A CTO should be technical by zerr on Monday September 26, 2022 @06:47PM (#32989616)
That's why becoming a CTO shouldn't be treated as promotion or "next level". And there should be the same compensation level for individual contributors.
Re:A CTO should be technical by brightball on Monday September 26, 2022 @05:19PM (#32988581)
If you have that much chaos that you’re insulating your team from, it sounds like you need to try to set some barriers. I’m not sure how anyone could be expected to function in the environment you’re describing.

*I have never worked in games.

Re:A CTO should be technical by austinjp on Monday September 26, 2022 @09:05PM (#32990578)
I'm curious about why and how you've become a CTO?

Presumably, you don't have to do it if you don't want to. If that's true, be nice to yourself and remember that on a regular basis :)

What you've described is pretty much the way many CTOs would describe the job. Don't worry. Treat it like any new discipline. Seek out expertise and learn from it. Make notes and crib sheets and read them regularly (they might be about financial management, or about people management, whatever you need).

Find a mentor if you can.

Don't burn out.

Don't be a jerk (ignore the more outspoken comments in this thread, you are clearly not well suited to sociopathy, congratulations).

You will not be able to please everyone all the time. You can't be everyone's friend all the time. But you can probably be decent to everyone nearly all the time.

Lying is shitty. Really, really shitty. Think about it.

Doubt is normal, but check yourself for imposter syndrome on the reg.

Ask yourself: what do you want?

If you don't like who you're becoming, move on.

Good luck :)

Re:A CTO should be technical by dijit on Wednesday September 28, 2022 @03:11AM (#33005071)
Apologies for not responding sooner.

The reason I became a CTO is three-fold:

Firstly, I was recommended for the position by the managing director of a large (the largest?) Swedish games company, so I figured it was a once in a lifetime opportunity.

Secondly, I asked my old CTO if it was a good fit for me as I’d been a manager before and I felt I preferred IC, I also have an abrasive way of communicating which worried me greatly, his response was that the abrasive parts of my communication style will melt away because it is bore out of frustration.

Finally; I have worked in meritocratic cultures but only when there was significant external political pressure from the publisher. Theoretically I could replicate that culture but without the political cruft; additionally I would be in a position to set the company up with long-term technological investments and partnerships: which I was trying to do before but managers are usually focused on short term goals.

> Find a mentor if you can.

> Don't burn out.

> Don't be a jerk (ignore the more outspoken comments in this thread, you are clearly not well suited to sociopathy, congratulations).

> You will not be able to please everyone all the time. You can't be everyone's friend all the time. But you can probably be decent to everyone nearly all the time.

This is good advice and I appreciate it greatly, I will wear these words going forward.

Thank you. :)

Re:A CTO should be technical by insane_dreamer on Monday September 26, 2022 @07:36PM (#32990032)
Maybe the question is what is (or should be) the role of the CTO. A lot of what you describe sounds more like Chief Product Officer (or Head of Product) rather than CTO.
Re:A CTO should be technical by vasco on Monday September 26, 2022 @05:26PM (#32988683)
> but I fear what will replace me if I leave

So you'll never retire or die?

Re:A CTO should be technical by dijit on Monday September 26, 2022 @05:28PM (#32988740)
I’m not very old, healthy enough and if I die then there’s not much more I can do, can I?
Re:A CTO should be technical by pvorb on Monday September 26, 2022 @06:07PM (#32989206)
That's a bit too extreme, isn't it? The situation simply might change in one way or another.

A skilled replacement might just appear at some point or the parts of the executive level they're fearing the most might leave. I've never seen a company without any changes in management personell over a decade.

Re:A CTO should be technical by Minor49er on Monday September 26, 2022 @07:08PM (#32989802)
Doesn't seem extreme at all to me. I used to work at a place that would stress the importance of keeping implementations easy to understand and documentation up to date in case "[team member] gets hit by a bus tomorrow and we have to replace him." (Some people apparently thought this was too macabre so they would try to change it to "they won the lottery and quit instantly," but the engineering team thought this to be a less likely scenario than getting hit by a bus)
Re:A CTO should be technical by dicriseg on Monday September 26, 2022 @10:44PM (#32991070)
Is this your first time managing people as well?
Re:A CTO should be technical by dijit on Tuesday September 27, 2022 @02:50AM (#32992214)
No, but first time for so many, I’ve had 3 direct reports before and in my last company I had 1
Re:A CTO should be technical by CallMeJim on Monday September 26, 2022 @06:11PM (#32989262)
This reads like a LinkedIn post.
Re:A CTO should be technical by dijit on Tuesday September 27, 2022 @02:49AM (#32992211)
The real CTO was the friends we made along the way.