It Depends: Lessons in Technology Leadership

A CTO needs to hire more engineers, and the numbers are working against the argument. Engineering spend has fallen as a share of revenue because the company grew faster than the team, so on paper it looks like efficiency. In practice, one resignation could sink the roadmap. Kevin Goldsmith's advice was to stop arguing from within and examine the organization as an acquirer would. Kevin has led due diligence as an acquirer at large companies and startups, and he's been examined as a target through acquisitions and investor rounds. From both seats, the same pattern keeps showing up: the organizations that come through well are the ones whose leaders already know where the problems are and have a plan for them. The catch is that the longer a leader has been in an organization, the less its workarounds look like problems. The framework here is the Outsider's Audit, four questions anyone doing diligence will ask, turned on your own team: Worth, Dependencies, Flow, and Risk. Kevin walks through each one practically, including building spare capacity at the org level so a resignation doesn't cancel a quarter of work, tracing a single ticket to find where work actually stalls, trading audits with a peer, and handling the people side, right up to the moment the team starts wondering if the company is being sold. The episode is aimed at CTOs and VPs who may face funding or acquisition diligence someday, but the approach works just as well for a director or engineering manager who needs to make the case for their team with evidence rather than instinct. Due Diligence in Funding & Acquisition, A CTO's Guide Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com) The theme song artist: Answers to April

A vendor the security team wanted, budgeted two years in a row, and never actually bought. When Kevin Goldsmith finally tried to spend the money, his CFO asked what the ROI was, and he didn't have an answer good enough to win the argument. Not long after, a new board arrived and told him he was underinvesting in cybersecurity. Same company, same customers, same risk, completely different verdict. Every technology leader owns budgets where the best possible outcome is that nothing happens. Security, compliance, reliability, backups, disaster recovery. They're the easiest money in the company to cut and the hardest to defend, because success looks identical to having never spent the money at all. This episode is about how to decide how much to spend, and how to defend the number when finance asks. Kevin lays out four price tags that other people are already attaching to your risk: the deal price your customers set, the insurance price your insurer sets, the compliance price regulators set, and the survival price you have to estimate yourself. He compares three companies where the right answer ranged from a large security team to a fraction of one person, revisits COVID as the disaster recovery test nobody scheduled, and covers the failure modes that show up again and again, including the raided line item and the backup nobody has ever restored from. Useful for CTOs, VPs of engineering, and directors heading into a budgeting cycle who need a defensible number rather than a benchmark, and for anyone who has been told in the same year that they're spending too much and not enough. Becoming a Business Leader: https://itdependspod.com/episodes/becoming-a-business-leader/ The Google SRE book, free online at https://sre.google/books/ Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com) The theme song artist: Answers to April

A developer builds a working replacement for an internal platform over a weekend using AI tools, then asks leadership why they can't ship it on Tuesday. The code is clean, the architecture is real, and the team is confused about the holdup. Kevin Goldsmith explores what happens when AI-powered development speed outpaces the organizational guardrails that once kept teams aligned. This episode explores the tension between team autonomy and organizational coherence in an era when building software has become dramatically faster, but deciding what to build has not. Kevin draws on Spotify's aligned autonomy model, his own experience watching founder-speed culture collide with a growing engineering team, and a practical framework he calls the Blast Radius Test: three questions that help teams determine whether a decision is theirs to make or requires a wider conversation. The episode also tackles the blurring line between prototypes and MVPs. When an AI agent produces a prototype with clean architecture, test coverage, and error handling, the output can look identical to a first production implementation. Kevin makes the case that the distinction now has to come from intent and organizational readiness rather than code quality, and shares a story about handing a team his own prototype only to watch them spend weeks trying to ship his throwaway code. This is for engineering leaders trying to figure out how to give teams room to move fast without losing organizational coherence. Henrik Kniberg's Aligned Autonomy video It Depends Episode: Every Decision Makes a Policy It Depends Episode: Fail Safe, Fail Smart... Succeed! Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com) The theme song artist: Answers to April

The spreadsheet says building is cheaper now, and the spreadsheet isn't wrong. A vendor's annual license on one line, a couple of developers and some tokens on the other. What that comparison leaves out is that building has always had two costs, and AI only made one of them smaller. Kevin has spent most of his career firmly on the buy side, with a mantra he gave his teams for years: don't invent things that already exist. This episode is him revising that position rather than abandoning it, and being specific about how much smaller the revision is than the enthusiasm in the industry suggests. He walks through a four-question test to run before agreeing to build something that already exists, covering blast radius, ownership cost, differentiation, and whether there's an exit path. Along the way: where building genuinely does make sense now, where it still doesn't regardless of how cheap it has become, the license cost trap that catches CFOs, why supply chain risk has started cutting in both directions, and the version of this decision that shows up in headcount instead of software. Two stories anchor it: an auth decision that gave back every dollar it saved and came within about a month of being much worse, and a build made deliberately with an exit already planned. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com)

Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022 In this episode, we discuss my experience building an exercise to better understand what is important to me in a role or company, and how I used the results to prepare for job interviews. I also discuss some of the mistakes people make when interviewing for roles during a downturn, particularly in how they present themselves. If you're currently looking for a job, or think you will in the future (we all will), this episode will be helpful. Some links: It Depends book information: https://itdependsbook.net Newsletter: https://kevingoldsmith.substack.com Questions/contact (I'll answer them in the podcast or newsletter): [email protected] Living in an Employer’s Market as a Developer article: https://blog.kevingoldsmith.com/2020/03/31/living-in-an-employers-market-as-a-developer/