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CTO Think

Author: CTO Think

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A pragmatic podcast about leadership, product dev, and tech decisions between two recovering Chief Technology Officers.
61 Episodes
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Don and Randy discuss content management options from the old-school Full Stack apps, WYSIWYG SaaS, and Headless + Static Site Generator options
Automation vs Programming

Automation vs Programming

2019-12-1700:41:49

Don describes his work on moving his company to Microsoft and his use of Power Apps. This leads to a discussion of the automation vs programming strategies and how this might be the future for all non-coding employment.
Switching to Services

Switching to Services

2019-11-1200:33:44

Randy is part of a team focused on building a Service Oriented Architecture with Go. Don figures out he has always been using services, but the SOA acronym seemed to involve more than simply work. Randy explains further the use of messages, queues, and other approaches to request buffering.
Domino's Pizza recently lost a lawsuit regarding the lack of accessibility features for their online ordering platform. Don and Randy discuss the ramifications of the decision and whether accessibility is worth the time and effort product managers might put into making their products more inclusive.
When a CTO is juggling multiple responsibilities, people, and projects, what is the best use of their time? Randy, once again, tells Don to put down the keyboard and quit coding stuff!
In honor of the second week of the college football season, Randy and Don discuss three programs, UCLA, Tennessee, and FSU, falling into disaster scenarios and compare each with CTO failures at technology firms. We keep the football/sportsball strategy discussion to a minimum, but we do eventually call out Tennessee as the "Steve Ballmer" of college football schools. Go Rocky Top?
A recent blog post by Philip Thomas of Moonlight titled "Startups Should Not Hire a CTO" sparked a conversation about why blanket statements like "Startups Should Not Do X" that are clickbait and should probably be avoided as good advice. Instead, we discuss letting your needs to drive your hires, instead, and the kinds of people you probably do want to hire to lead technical efforts. Randy's cats don't like anything about the recording, in addition to the article.
With hacking stories dropping on a seemingly daily basis, the question keeps coming up about application security: Should you build your own user authentication or use an external service? This week, Don and Randy discuss the Buy vs Build debate around auth, and whether the high costs of outsourcing outweigh the high risks of rolling your own.
In reaction to a Twitterstorm about the concept of a 10x engineer being important for any startup, we discuss the downfalls of such a thing and what positives exist.
Randy is about to start a new job and has a number of opinions about the job search, hiring, negotiation process he recently went through. Don tries to play Devil's Advocate as the employer/hiring side, but Randy's not hearing any of it! Don uses coconuts as the example of currency and Randy somehow manages to quadruple the asking price for labor in the Hawaiian produce marketplace Don tried to set up.
The show begins discussing setting up a product roadmap for AspirEdu, but things devolve when Don mentions he is considering swapping Wordpress for the marketing website with a static site builder. Randy thinks adding more developer dependencies is a bad idea and coins the term "Free-time Driven Development" (tm) and can't wait to make T-Shirts and Medium posts promoting the brand.
We have an exceptional guest for our 50th episode in Jess Szmajda, CTO of Axios, and we cover a whole lotta ground: From building "horrible PHP sites", to constructing retail tech teams from scratch, we then tackle the subject of taking on the role of CTO of a fast-growing media firm, being a trans CTO, and promoting a more diverse community in technology. Whew! We start out discussing the difference between a CTO and Director/VP of Engineering, title creep, and whether the idea of a "software architect" has any relevance at all. We then cover wider ground with managing small vs large teams, the adoption of Spotify squads/pods in team management, and adding new business (TV) that is vastly different than the core company product (online publishing). The subject matter covers a vast amount of ground, but it's all valuable in today's tech community.
Stages of the CTO Lifecycle

Stages of the CTO Lifecycle

2019-05-2100:54:071

This week we review an old, but good, blog post by Andy Skipper named "Looking at the life of the CTO through the stages." We discuss our own experiences across these stages and the ones we haven't reached, yet. Randy also continues his rant on tech developer/manager hiring practices, so no surprise there!
Over the past two decades of working in tech, the use of Continuous Integration (or CI) has become a mainstream approach to product development. Randy and Don discuss the systems they used before (or lack thereof), what they use now, and why Continuous Integration meets the hype.
We discuss business metrics, reporting, statistics, and how many of the numbers, without context, lack much value. Can your business deliver the Five Nines? Does it even need to? What kind of performance can you guarantee when upstream providers are involved?
Don's firm is looking to hire a non-senior Python developer to help spread the workload of the engineering team. We discuss how he's writing up the job description, who he's really looking for in the role, and what kinds of skills the person must have to be effective in the role.
A customer claims the service provided didn't meet expectations despite them choosing the more “economical” solution. Another client’s manager felt a contractor “yelled” at them, but the contractor felt they barely raised their voice. This week we talk about the human side of handling different opinions and trying to prevent problems like these in the first place.
Hiring Good Consultants

Hiring Good Consultants

2019-03-1200:50:39

This week we talk about how we’ve hired consultants in the past, where we’ve failed, and the perspective of consultants that might help tech leaders understand who they’re hiring.
CTO, CIO, CDO, WTH?

CTO, CIO, CDO, WTH?

2019-02-2600:41:29

This week we discuss the various C-Level titles in the tech world: CTO vs CIO vs CDO vs others. What do folks with those titles tend to do and do the titles really matter? Also, Randy talks about his newest hobby: Kitten pictures!
Don's company ran into problems when their email provider, Mandrill, suffered a significant outage. Randy and Don discuss how they handle outages, prepare for switching to other providers (before or after failures), and how to go about communicating those issues to clients. Don debates whether using a scooter rental requires a helmet and Randy tells him to ignore his mother's advice. References are made to Matthew McConaughey, and we apologize, in advance.
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