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Ask HN: Blogs about Being CTO/Head of/Lead Dev?
190 points by ggregoire on May 21, 2019 | hide | past | favorite | 54 comments
Mainly interested about retrospectives, feedbacks, tips, etc., from CTO/Head of… or Lead dev of 10+ teammates, about growing teams, people management, project management, tech decisions, processes, etc.



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

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!


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).


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.


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


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...


fwiw, rands (Michael Lopp) is the VP of Engineering at Slack


And the author of the first book I bought on the topic: "Managing Humans: Biting and Humorous Tales of a Software Engineering Manager"


Great, insightful book and a fun read. Highly recommend

The blog is great too! http://randsinrepose.com


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.


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.


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.


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?


Old content in Slack is not available through search if you are not on a paid plan but I was more referring to the public open web and people trying to find answers through search engines.


If you use the other plan, old resources are not accessible anymore. Is it fine enough?


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.


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.


Camille also has a blog at http://www.elidedbranches.com. I second the recommendation.


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 ;)


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


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


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...

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.


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

I shared my experience going to their conference:

http://redgreenrepeat.com/2019/03/08/conference-debrief-mana...

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


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...


I hate self-promotion, but I write on 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!


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


A fair point! Fixed.


Nice stuff. Thanks for sharing.


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


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


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.


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 :)


The Modern CTO podcast by Joel Beasley is a great resource for this (https://moderncto.io/). Lots of insight from tech leaders across many industries.


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/ (He founded StackOverflow.com along with the previously mentioned Joel Splosky)

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


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


Would highly recommend Irrational Exuberance! by Will Larson of Stripe engineering: 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.


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


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


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



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/

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.


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


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


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.



CTO craft has a series of interviews called "Zero to CTO" - 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).


Engineering Impact from GitPrime.



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...


a CTOs slack channel sounds like a way to go !

Would like to join, anybody else ?


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


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


Sure. But it's hard to keep up. I have once created a WhatsApp CTO group and it didn't turn out well.


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


I also hear Wordpress is great for this.




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