Software Defined Interviews

Episode 3: Improvement requires fear, or, digital transformation by crisis and fear

Software Defined Interviews

Show Notes

<p>People in large organizations avoid improving for improving&#39;s sake. They&#39;re very rarely proactive in transforming. Instead, it seems that management in most large organizations only act, and change, when they fear competition and failure. &quot;Everyone&quot; knows this is a bad strategy, and yet &quot;everyone&quot; does it. Perhaps we should embrace that behavior, or at least be empathetic, and figure out how to work with it.</p>

We discuss this problem and things to do in this episode.

Also, we find out why Coté always has bad breath.

Mood board:

(6:30) - The daily, normal fears are going to drive what a business does more than large, one-off crises.

If your inventory is on an AS/400, then you're in trouble.

A chaos monkey for business, or, training for the unexpected.

"When there's not a crisis, every penny is squeezed out of technology."

Outsourcing, but the harmful type.

Hold your customers close, know your evolving storefront.

Now, software is the primary storefront.

To improve, you must have an enemy.

(20:51) "If you're trying to modernize, do this 'digital transformation,' it has to come from a place of an existential problem."

(21:26) To prepare for a major disruption, you have to prepare for a bunch of minor, incremental disruptions. You have to sell [the return] on paying for change.

(25:51) If you want to justify paying for continuous delivery, you have to find a problem to solve.

(27:41) They're bean counters, so just count the beans for them - just give them some beans and they're happy.

(28:58) As technologist, our views on revenue are not considered important or valid.

(29:21) Fear and loss are often easier to quantify, e.g., "if the database goes down, the business halts, and we loose millions a minute." Growth potential is harder to quantify and pitch, so we often ask for money based on fear and loss.

(29:36) "Even though I think about revenue streams, I've never been taken as seriously when I talk about them, as when I talk about fear."

Finding people outside of IT that care about software, like, in "the business."

(32:55) The only reason for technical agility, is business agility.

(33:44) If you do live through a crisis, try to internalize your failure to prepare so you only learn once from crisis, not again and again.

(35:33) The Business needs the fear, and then needs to ask IT to help with some optimistic technology action...cause no one's gonna believe IT.

More from Software Defined Interviews

Oct 22, 2026

Rick Clark is Global Head of Cloud Advisory at UST, and co-founded OpenStack. His argument is that enterprise architecture is nearly extinct, killed off by fifteen years of shifting every decision left, and that this is how one insurance company he worked with ended up running over 50 secrets managers in production. Whitney and Coté push on whether platform engineering was meant to solve exactly that, and on what a modern enterprise architect would do instead - write the rules the platform enforces. The back half is agents: why nobody is ready to run them in production, and the difference between a rule an agent cannot break and one it must not break.

Sep 30, 2026

Viktor Farcic is a developer advocate at Upbound, runs the DevOps & AI Toolkit YouTube channel, and was last on the show back in episode 89. Whitney and Coté start with the animated bedtime stories he has started making - tech history told as fairy tales with a nightmare at the end - which he began after catching sight of himself in a mirror and deciding people should not have to watch that. From there it is what his working day looks like now, with 20 to 50 agents running at once, a coder and a tester and a reviewer who are not allowed to do each other's jobs and argue until they agree, and a private YouTube channel where the agents post recorded tests for him to review on his phone in the morning. The last stretch is money: why he thinks AI is cheap next to what a person costs, why he expects a bloodbath as industries fail to adapt, and a walk through Docker, Chef, Puppet, Ansible and HashiCorp on whether an open source company can ever turn a profit on its own.

Sep 20, 2026

Lin Sun is Head of Open Source at Solo.io, a recent KubeCon + CloudNativeCon program co-chair, and an emeritus member of the CNCF Technical Oversight Committee. Whitney and Coté start with the keynote she gave in Amsterdam, where she flew a drone over 13,000 people so an AI model on her laptop could score how engaged the audience was - it broke twice on stage, and Whitney, who was in the room, remembers nothing else from that day. Lin’s account of why it worked anyway is a checklist: a wow factor, something the audience does every day so they can relate to it, real engagement, and a planted surprise. From there they get into the part of co-chairing nobody sees, where three thousand submissions become about two hundred talks, how the AI-written ones get spotted, and why the CNCF cannot simply run a detector over the pile. The rest is open source as a job - twenty years of it, Istio at IBM through to Solo, and a straight answer to the question her own reports keep asking her, which is whether working on open source makes you less strategic to the company paying you.

Sep 2, 2026

Jason Yee is a Staff Technical Advocate at Datadog and one of three global co-chairs of DevOpsDays, and both jobs turn out to be mostly about getting other people to talk. Whitney and Coté ask him how the DevOpsDays machine actually works - local teams run the events, a global core team advises, and the co-chairs exist as a final escalation point - and what happens to conference sponsorship now that DevOps is mature rather than hot. His answer is that the sponsors who do well have stopped counting leads and started running workshops, on the grounds that a Lego giveaway gets you a list of people who wanted Lego.

Aug 20, 2026

Michael Rishi Forrester does AI workforce transformation at Accenture LearnVantage, after three years at KodeKloud and about thirty years in IT before that. Whitney and Coté talk with him about running tabletop role-playing games with AI. He built his 19-year-old son a homebrew campaign on top of Lancer, the sci-fi mech game, in about 20 hours instead of the 60 to 100 it would have taken him before - and got a website, a virtual tabletop and some Discord bots out of it. What breaks is the interesting part: there was a night when every shot did one damage, because the model had quietly stopped using the dice harness and started doing the math itself.

See all episodes →