CTO Think

CTO Think

www.ctothink.com
A pragmatic podcast about leadership, product dev, and tech decisions between two recovering Chief Technology Officers..


From Manager/Dev to Non-coding Manager
May 19 • 31 min
Right before the COVID pandemic hit, Randy was asked to take on the management of two new teams, which changed his typical role of manager-developer to strictly people management, meetings, and project tracking. Don and Randy discuss the change as it…
Difficult Choices and Hard Conversations
Mar 31 • 43 min
Don and Randy talk about what’s been going on with the COVID-19 pandemic and how it has affected their firms, jobs, and side projects. What does it mean to talk to folks under your wing? What kind of leadership does it take when the real world seems out…
Improving Visual Communication for Remote Management
Feb 25 • 29 min
Randy is making efforts to improve the communication of visual examples via remote video meetings. We discuss his first attempt to achieve online whiteboarding using a Macbook Pro, a Wacom One tablet, and a Google Jamboard.
Security Concerns Keep Coming
Feb 11 • 34 min
In Don’s role as CTO for AspirEDU, he has a number of security audits posed by potential customers and increasing complexity around third-party hosts. Randy keeps wanting to talk about the XFL (Part 2).
Modern Content Management Options
Jan 7 • 44 min
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
Dec 17, 2019 • 41 min
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
Nov 12, 2019 • 33 min
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…
Is Accessibility a Worthwhile Focus?
Oct 29, 2019 • 33 min
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…
How Should a CTO Use Their Time?
Oct 1, 2019 • 32 min
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!
Organizational Train Wrecks explained by College Football Dumpster Fires
Sep 10, 2019 • 38 min
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…
Should Startups Avoid Hiring a CTO?
Aug 20, 2019 • 33 min
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…
Authentication: Buy it or Build it?
Aug 6, 2019 • 46 min
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…
2x CTOs talk about 10x developers
Jul 16, 2019 • 49 min
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.
Post-mortem on Randy’s Job Search
Jul 9, 2019 • 54 min
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…
Ditching Wordpress vs Free-time Driven Development
Jun 18, 2019 • 55 min
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…
From Hands-on Dev to CTO: Jess Szmajda, CTO of Axios
Jun 4, 2019 • 44 min
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…
Stages of the CTO Lifecycle
May 21, 2019 • 54 min
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…
Benefits of Continuous Integration
May 7, 2019 • 41 min
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…
Business Metrics and the Lack of Context
Apr 23, 2019 • 42 min
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…
Writing a Job Description for a Non-specific Job
Apr 9, 2019 • 68 min
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…
Customer Perspectives and Managing Expectations
Mar 26, 2019 • 49 min
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…
Hiring Good Consultants
Mar 12, 2019 • 50 min
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?
Feb 26, 2019 • 41 min
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!
When a Third-Party Service Fails
Feb 12, 2019 • 46 min
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…
Pushing Your Team and Self to the Limits
Jan 29, 2019 • 67 min
Following up on another Elon Musk communication, we discuss the side effects of working too many hours, burning out, and how you might be guilty of causing extra-hour angst with only a simple email sent after work.
Setting Goals for your Team
Jan 15, 2019 • 47 min
Don is setting up goals for AspirEdu for 2019, which takes us into a discussion about how to set up big projects and campaigns for small firms that have lots of small tasks to get done at the same time. How do you get executive buy-in, maintain momentum,…
Brainstorming the Tech, Managed meetup
Dec 31, 2018 • 68 min
As we move into 2019, Randy and Don discuss a new meetup concept they aim to create called Tech, Managed. With goals to build upon the growth of the CTO Think and This Old App audience, the Tech, Managed meetup will create a learning space for managers…
Kubernetes Exploits, Bernie Madoff, and Minimal Skepticism
Dec 18, 2018 • 48 min
Don and Randy discuss a recent exploit that came to light in the Kubernetes container framework that seemed to fade off as a widespread concern. This leads to a discussion about how much diligence is required by technology managers regarding the risks…
Review of the State of JS Survey
Dec 4, 2018 • 65 min
How is Angular doing vs React and Vue? What are the most used and growing back-end JavaScript frameworks. Which strongly-typed flavor of JavaScript is winning hearts? This week, Don and Randy discuss the State of JS survey results for 2018 and review from…
Crossover Episode - The World vs React (Nuff Said)
Nov 20, 2018 • 30 min
The previous two episodes of our sister podcast, This Old App, discussed the rapid development of React and its possible side effects on the development community. For this CTO Think episode, we run our first “crossover” and discuss how tech leaders and…
Should We Open Source This Code?
Nov 7, 2018 • 28 min
Don and his company, AspirEDU, decided to open source a small bit of code for the first time for the Django community. We discuss the various considerations—across proprietary, support, and licensing questions—the company made to push forward the release,…
Adventures in Interviewing
Oct 23, 2018 • 70 min
Randy is moving to Kansas City and exploring new job opportunities both local and remote, which has him in the thick of a variety of interviewing processes. Don and Randy discuss the good and bad about some of the firms’ approaches and how Randy is still…
Build vs Buy and Disrupting Processes
Oct 9, 2018 • 40 min
We’re back after a couple-week break! Don and Randy discuss the ever-debated strategy of building versus buying your software solutions. But they up the ante by discussing how existing workflows and processes are perhaps a bigger consideration than SaaS…
Handling Critical Feature Updates
Sep 11, 2018 • 55 min
Don’s firm recently underwent its first major platform upgrade and we discuss the various ways they prepared, tested, and worked through the changes, all the way up to the dreaded “point of no return.”
Elon Musk and Leading Your Team to Burnout
Aug 21, 2018 • 60 min
Pulled from the media, Don and Randy discuss Elon Musk’s interview regarding the personal toll that his attempt to run three companies, perhaps poorly, is taking upon himself. Moreso, they talk about what it means to be in a leadership position and how…
Debating (Angrily) the Responsibility of Cross-platform Support
Aug 14, 2018 • 61 min
Don runs into a problem with a podcast app as he launches a new podcast of his own, Friday Night Stripes, and wants to deploy his show on Overcast. The issue? Don is not an iOS user and cannot find a way to sign into the Overcast website, which . . .…
Betting on Vue JS with Gregg Pollack
Aug 1, 2018 • 57 min
Covering everything from Rails for Zombies to Code School to Vue Mastery, we talk with one of the original online tutorial creators, Gregg Pollack, and how he decided to invest in the Vue.js community and a new front-end open source project. Gregg also…
When People Don’t Listen to You
Jul 17, 2018 • 53 min
We discuss the inevitable issue of bosses, owners, managers, and clients not listening to every bit of advice we offer up. From ignoring the frustration, the psychological reaction, and avoiding a passive-aggressive response, to the maturation of our…
When Everything’s Going Wrong
Jul 3, 2018 • 51 min
How do you get things back on track when everything from the engine to the caboose is falling off? We discuss steps to take when everything and anything is spiraling downward on a tech project.
Stakeholder Types and Working With Them
Jun 26, 2018 • 62 min
We discuss the various types of stakeholders that a technology leader may need to deal as being part of a company or a particular product. We discuss the various motivations and communication techniques necessary across Executives, Investors, Regulators,…
Thinking About Dependencies
Jun 12, 2018 • 62 min
What are the considerations do you need to make regarding third-party services and software? We talk about relying on Github after the Microsoft purchase, using AWS or Firebase, and the world of JavaScript, Node, and NPM. And Randy talks about his pet…
Learning as a Cultural Component with Griffin Caprio
Jun 5, 2018 • 60 min
We speak with Griffin Caprio of Dante32 about his experiences building trust and psychological safety, accepting failure in a positive way, and creating a learning-based culture on teams from the top-down.
GDPR Pain and Projects Outside Your Expertise
May 29, 2018 • 53 min
We lament about the recent GDPR hullabaloo, our initial reactions to the new regulations, and how we approach projects that we don’t have any business handling in the first place, but still fall onto our shoulders.
Compassionate Coding with April Wensel
May 22, 2018 • 36 min
April Wensel started a company named Compassionate Coding, which aims to “humanize the tech industry.” We discuss why she started the firm and how she goes about making the tech industry a better place to work. We also learn that using the term “soft…
Meetings, Schmeetings
May 15, 2018 • 54 min
We talk about meetings, the negative vibe the tech industry has taken against them, how to best run meetings, or finding ways to communicate without wasting so much time.
Social Media Side-Effects
May 1, 2018 • 49 min
Would you hire Kanye West if he was a great programmer, despite his social media presence? This week, we talk about social media quality control, public personas, and the challenge of being inclusive while trying to maintain a steady team dynamic. We also…
Networking for Introverts
Apr 24, 2018 • 59 min
Having a strong network makes for a huge advantage for career opportunities and learning how to lead. We discuss how to push past shyness and introverted tendencies to grow your own network of relationships.
Choosing a Tech Stack
Apr 17, 2018 • 60 min
There are a lot of factors tech managers need to consider when inheriting or choosing a technology stack. We talk about how we chose specific stacks in the past (or didn’t) and why we’re using a brand new one for a side project.
Identity Heft
Apr 10, 2018 • 48 min
With hacking, data security, and privacy as huge issues in the press, we discuss how we approach identity management on both products and across our teams.
Don’t Be Evil-ish?
Apr 3, 2018 • 52 min
Where do you draw the line on ethics? How do you take a stand when you want to keep your job? This week, we discuss ethical behavior and the responsibility people have regarding it.
Non-Disclosures, Non-Competes, No Way?
Mar 27, 2018 • 48 min
Should you sign non-compete or non-disclosure agreements? Are these kinds of contracts binding? Are they even useful for your business? We discuss everything from saying “heck, no,” to turning the ask into an initial business agreement test.
You’re so vain, you think in-office work is about you
Mar 20, 2018 • 59 min
We discuss our history with in-office and remote work, why junior devs might reconsider working outside the office, and how requiring folks to work in your proximity is a trait of managerial vanity.
Fostering a learning environment with Mark Thompson of Trilogy
Mar 14, 2018 • 55 min
We speak with our first guest, Mark Thompson of Trilogy Education, about his approach to creating a productive learning environment both on the job and in a classroom setting. Mark is also working on a side project named Totally Strong, which is pushing…
Communicating on a roller coaster of uptime and downtime
Mar 7, 2018 • 58 min
Randy and Don found themselves stranded, mid-ride on the Expedition Everest roller coaster at Disney World’s Animal Kingdom. Following their rescue, and during an in-person recording from Orlando, they talk about how a tech manager should handle technical…
Are code challenges a lazy or legitimate method for hiring developers?
Feb 25, 2018 • 54 min
Are code challenges or quizzes a legitimate practice for hiring developers? We debate whether the method of filtering candidates via whiteboarding or code games is plain lazy or a necessary part of the recruiting process for engineers.
Skills for a career in tech leadership
Feb 18, 2018 • 44 min
If a junior developer is looking at the fork in a technology career path of software engineering or management, what kinds of skills do they need for the leadership side?
Developer focus is an excuse not to talk, right?
Feb 10, 2018 • 46 min
Is the call for “developer focus” a selfish complaint from precious snowflake employees? What right do developers have to ruin the design trend of great-looking open offices where collaboration magically happens? This week, we discuss how we feel about…
Your hosting strategy - Choosing from self, managed, cloud, or serverless
Feb 3, 2018 • 40 min
How do you choose the best hosting options for your product or firm? This week, we discuss the thinking in a choice between self-hosting, managed hosting, cloud options, and the new buzz word: “serverless”.
Work-life balance
Jan 27, 2018 • 39 min
We discuss the importance of a work-life or non-tech balance for someone building a career in technology. Do folks need to set aside a specific amount of time, or any at all, not working on things related to their job?
Does a tech manager need to code to be effective?
Jan 18, 2018 • 37 min
Randy is a CTO that codes almost daily. Don has found it difficult to string together multiple days where he’s able to code for his current roles. Today, we tackle the topic of whether a CTO or technical manager needs to be able to code to be effective at…
Antifragile and TDD - What’s the value?
Jan 12, 2018 • 33 min
Don brings up the subject of chaos, based on a book he’s been reading, Antifragile, by Nassim Nicholas Taleb. We discuss the merits of test driven development, unpredictability, and how technical managers can work towards a more resilient product in the…
Risk and Exploits - Dealing with Meltdown and Spectre
Jan 5, 2018 • 42 min
Randy and Don discuss an item ripped from the headlines: What should a technical manager do about the recent Meltdown and Spectre exploits? They move into the CTO modes of research, understanding, translation, preparation, upgrading, monitoring, and, most…
Managing tech debt - When best to work on it?
Jan 2, 2018 • 28 min
Don faced an issue at his education tech firm: When should you slow down forward progress on new features in order to spend time on festering technical issues?
Hiring developers - Who should I hire to build an app?
Dec 28, 2017 • 25 min
Randy was posed a question by a potential client: “I want to build an app. Who should I hire?” and he asks the same question to Don.
Introducing CTO Think
Dec 23, 2017 • 4 min
Welcome to CTO Think, a podcast about how technology leaders think about business, tech, and people problems. Don VanDemark and Randy Burgess, two current and former Chief Technology Officers will discuss the various challenges managers face in a product…