Ask HN: Blogs about Being CTO/Head of/Lead Dev?

190 points by ggregoire 5 years ago

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.

wjossey 5 years ago

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!

  • wjossey 5 years ago

    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).

kopos 5 years ago

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.

akurilin 5 years ago

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

  • dewey 5 years ago

    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...

    • usmannk 5 years ago

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

      • goshx 5 years ago

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

    • seattle_spring 5 years ago

      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.

      • Xeago 5 years ago

        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 5 years ago

          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.

          • village-idiot 5 years ago

            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?

      • dewey 5 years ago

        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.

      • IloveHN84 5 years ago

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

tspike 5 years ago

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.

  • mdorazio 5 years ago

    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.

rficcaglia 5 years ago

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 ;)

  • lucasmullens 5 years ago

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

cbisnett 5 years ago

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.

jstanier 5 years ago

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!

  • jellevdv 5 years ago

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

    • jstanier 5 years ago

      A fair point! Fixed.

  • wjossey 5 years ago

    Nice stuff. Thanks for sharing.

afarrell 5 years ago

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

toomuchtodo 5 years ago

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

  • Noumenon72 5 years ago

    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 5 years ago

      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 :)

  • zaidos 5 years ago

    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.

erikig 5 years ago

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 ;)

taurusismysign 5 years ago

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

qin 5 years ago

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.

chapati2301 5 years ago

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

machtesh 5 years ago

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.

royosherove 5 years ago

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

darrenwestall 5 years ago

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

thundergolfer 5 years ago

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.

moyvera 5 years ago

a CTOs slack channel sounds like a way to go !

Would like to join, anybody else ?

  • striker_axel 5 years ago

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

cagenut 5 years ago

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