
Ask HN: Blogs about Being CTO/Head of/Lead Dev? - ggregoire
Mainly interested about retrospectives, feedbacks, tips, etc., from CTO&#x2F;Head of… or Lead dev of 10+ teammates, about growing teams, people management, project management, tech decisions, processes, etc.
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wjossey
Also not a blog, but I run a free mentoring service for managers. Mostly meet
with folks from HN and Twitter, and I do daily sessions.

[https://freemanagermentors.com](https://freemanagermentors.com)

While there are tons of great resources out there, one thing to keep in mind
is that general advice is often bad advice, when it comes to teams and people
management. Be careful about over-correcting for certain advice that on the
surface seems helpful, but misapplied to the wrong context is detrimental.

One example is that a lot of the people I talk to have been attempting to
apply Radical Candor to their culture, with fairly mixed results. There's a
lot to love about the intent of RC, as an example, but misapplied to the wrong
personality types can be disastrous, demoralizing, and counterproductive to
the receiver.

I'd highly recommend as you try to level up any management skills, you talk to
someone who has attempted to put something into practice and get a sense for
the failure modes. This might help you adapt it to your culture and team so
that the downsides are mitigated and the upsides are still there.

Hope that's helpful!

~~~
wjossey
The response to this has been really wonderful, and my calendar is now almost
full all the way out for the next four weeks.

If you have something urgent you'd like to discuss, please email me directly.
My email is in my profile. If I can make time for a quick call, I will.
Otherwise, I'll do my best to respond quickly over email, or refer you to
another mentor that has offered up their time in the event I get overload
(which isn't always the case but is the case at the moment courtesy of the HN
hug).

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kopos
Please read 'High Output Management' by Andy Grove.

There has never been a when I kicked myself in the head for not having
discovered the book earlier. My better part of 6 years moving into a hazily
define leadership role which was a mix of de facto CTO, technical architect,
product manager, product development, hands-on developer, people management,
project management - had me running in a high-stress environment for ~ 6
years. I think a lot of mismatch of expectations, could have been avoided had
I followed the lessons earlier.

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akurilin
The Rands leadership Slack is great for this purpose:
[http://randsinrepose.com/welcome-to-rands-leadership-
slack/](http://randsinrepose.com/welcome-to-rands-leadership-slack/)

~~~
dewey
To me it’s really sad that apparently great resources are being created
entirely in some silo (Slack) that’s not preserved or accessible by everyone.

The section about “if you have a new topic just create a channel” sounds like
the perfect user case for a normal forum software...

~~~
seattle_spring
Who is it not accessible to? Just because you choose not to create a Slack
account doesn't mean it's not accessible to you.

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Xeago
Slack does quite poorly on accessibility, so anyone using assistive measures
from their operating system or separate application (voice instructed
navigation, screen readers etc) will have a much harder than the average blog
post or mailing list.

~~~
seattle_spring
Based on the context, it's pretty clear to me that the parent comment was not
referring to accessibility in the a11y sense, but more of the "Slack is a
private company and therefore inherently closed and evil" slant.

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village-idiot
I personally find Slack to be utterly abysmal at actually keeping information,
stuff that scrolls up beyond the fold is effectively lost. Maybe that's what
GP meant?

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tspike
Not a blog, but if you haven't read the book The Manager's Path by Camille
Fournier, I highly recommend it. Has eased my experience considerably, and it
is very specifically targeted toward modern software development.

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mdorazio
I also support this recommendation. If you want a one-stop shop for practical,
actionable advice on going from mid level to CTO level on a tech/product
track, this book is the best I've found.

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rficcaglia
[https://www.joelonsoftware.com/](https://www.joelonsoftware.com/)

Be like Joel. Whenever I am in a quandary, I ask “what would Joel do?”

Though he would probably be reviewing code right now, not reading HN ;)

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lucasmullens
I honestly think that for someone in his position, reading HN might be more
useful than reviewing his team's code.

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jgrahamc
Realize that I'm talking about myself but I wrote about my time at Cloudflare:
[https://blog.cloudflare.com/helping-to-build-cloudflare-
part...](https://blog.cloudflare.com/helping-to-build-cloudflare-part-1/)

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cbisnett
The Gusto co-founder describes his role and changes as they grew to 100
engineers in this blog: [https://engineering.gusto.com/how-my-role-as-cto-has-
changed...](https://engineering.gusto.com/how-my-role-as-cto-has-changed-as-
weve-grown-to-100-engineers/)

I found it reassuring I wasn’t the only founder who still felt they could
provide more value by helping build and architect the product than just simply
managing budgets and recruiting.

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acl777
Manager Tools has been my favorite resource since leading a team and being
able to work better! The podcasts are free:

[https://www.manager-tools.com/all-podcasts](https://www.manager-
tools.com/all-podcasts)

I shared my experience going to their conference:

[http://redgreenrepeat.com/2019/03/08/conference-debrief-
mana...](http://redgreenrepeat.com/2019/03/08/conference-debrief-manager-
tools/)

Please ask me if you want to know anything specific that I don't cover.

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eries
I wrote about this more than 10 years ago, I can’t believe it’s been so long:
[http://www.startuplessonslearned.com/2008/09/what-does-
start...](http://www.startuplessonslearned.com/2008/09/what-does-startup-cto-
actually-do.html)

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jstanier
I hate self-promotion, but I write on
[http://theengineeringmanager.com/](http://theengineeringmanager.com/) which
might also have some interesting articles for you.

There's a Management 101 section which I wrote for people becoming a team lead
for the first time, and then the Growth section expands into wider things.

I'm VP Engineering @ Brandwatch. Feel free to get in touch if you want to chat
more any particular topics!

~~~
jellevdv
VP of engineering but can't install a simple SSL cert! /s

~~~
jstanier
A fair point! Fixed.

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afarrell
Different medium, but the conference series Lead Developer has many good
youtube videos about this on the channel White October Events.

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toomuchtodo
Don’t look for blogs, seek out people in these roles and ask them for their
advice. People naturally want to be helpful.

~~~
Noumenon72
I feel like asking for generic career advice when there's so much out there is
wasting people's time. Also, the blogs are going to be much less off the cuff
-- more time put into bridging the inferential distance and finding good
examples. What are the odds that someone random person you met is going to
have as good of a perspective as the most insightful blogger's perspective?
You're probably going to get a lot of platitudes and bragging.

~~~
wjossey
Maybe! I’m biased because I run free sessions on this sort of stuff, and I
like to think I don’t do too many platitudes or brag. Hard to say :)

The advantage of talking live with a human on this stuff is context. There are
dozens of frameworks you can use for any different situation, but
understanding when not to use one is as powerful as knowing when to use it.

Blog posts rarely capture that nuance. A lot of times they can’t for
confidentiality reasons. Talking live with a manager with a decade of
experience can help you to short circuit a challenge much quicker than trying
to sort out the best online resource.

Not saying online stuff isn’t great! It is. Just defending live chats too :)

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erikig
I'm pretty sure most visitors here are familiar with both of these since they
are almost part of HN canon but I'll include them here for completeness:

Jeff Atwood's - Coding Horror -
[https://blog.codinghorror.com/](https://blog.codinghorror.com/) (He founded
StackOverflow.com along with the previously mentioned Joel Splosky)

Paul Grahams - Essays -
[http://www.paulgraham.com/articles.html](http://www.paulgraham.com/articles.html)
(Technically not a blog, just a series of essays organized in a chronological
order ;)

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taurusismysign
Been talking to leaders in the space on building and run great teams,
including interviewing process, retaining culture and other wide range of
topics. Here is the link to the podcast where a brief summary of the episode
is also available for quick read -
[https://podcast.nurture.team](https://podcast.nurture.team)

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qin
Would highly recommend Irrational Exuberance! by Will Larson of Stripe
engineering:
[https://lethain.com/tags/management/](https://lethain.com/tags/management/)

He’ll be a publishing a book on this soon (An Elegant Puzzle) if you’re
especially curious.

Disclaimer: I work with Will at Stripe.

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qrush
There's LOTS of great content from The Lead Developer conference. Definitely
try to attend one soon. Lots of talks published here:
[https://www.youtube.com/channel/UCmM3eCpmWKLJj2PDW_jdGkg](https://www.youtube.com/channel/UCmM3eCpmWKLJj2PDW_jdGkg)

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chapati2301
I love the softwareleadweekly.com newsletter, the author also wrote a book
called "Leading Snowflakes" which helped me when I first transitioned into a
leadership role: [http://leadingsnowflakes.com](http://leadingsnowflakes.com)

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johnb
[https://devtomanager.com/](https://devtomanager.com/) is a good one,
especially for those just making (or about to make) the transition.

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ggregoire
About management:
[https://news.ycombinator.com/item?id=17238135](https://news.ycombinator.com/item?id=17238135)

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machtesh
Not a blog, but if you end up needing specific and ongoing advice about people
management from experienced coaches, we offer an unlimited coaching service
for managers of technical teams:

[https://leadingup.co/](https://leadingup.co/)

One thing that I think is important that you won't find in blogs is that you
have to change your behavior as well as your teammates' behaviors in order to
actually see change. Regular discussions with a coach about specific
situations will help make sure these behavior changes are consistent.

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royosherove
I maintain a blog about tech leadership at 5whys.com (turned it into a book
later on called "notes to a software team leader")

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darrenwestall
I don’t have any blogs but happy to chat on anything specific you may need -
feel free to connect on LinkedIn.

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thundergolfer
erikbern.com is the blog of a previous engineering manager of the ML team at
Spotify who is now CTO of Better Mortgage, a tech startup in NYC.

His blog post regularly show up at the top of HN, and a good number of them
are directly related to the thinking behind how he does his job.

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joelx
[https://joelx.com/](https://joelx.com/)

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jamescrowley
CTO craft has a series of interviews called "Zero to CTO" \-
[https://medium.com/cto-craft/tagged/interview](https://medium.com/cto-
craft/tagged/interview) which might be interesting for you. They also have a
Slack community.

(disclaimer: I was one of the CTOs interviewed).

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mersenne
Engineering Impact from GitPrime.

~~~
cotsog
i.e. [https://www.gitprime.com/engineering-
impact/](https://www.gitprime.com/engineering-impact/)

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lkrubner
I wrote of my experiences here, as a cautionary tale, and an antidote to the
often over optimistic hype about startups:

[https://www.amazon.com/Destroy-Tech-Startup-Easy-
Steps/dp/09...](https://www.amazon.com/Destroy-Tech-Startup-Easy-
Steps/dp/0998997617)

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moyvera
a CTOs slack channel sounds like a way to go !

Would like to join, anybody else ?

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ctocraft
We have circa 800 CTOs chatting in the CTO Craft Slack group, fill in your
details here and I'll get you added:
[https://ctocraft.typeform.com/to/XXRNqV](https://ctocraft.typeform.com/to/XXRNqV)

~~~
moyvera
Cool, I'm sending my info, happy to join

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cagenut
based on most of the links to it my understanding is that medium.com is such a
blog

~~~
seattle_spring
I also hear Wordpress is great for this.

