It Depends: Lessons in Technology Leadership

About It Depends: Lessons in Technology Leadership

Kevin Goldsmith brings you lessons and advice from decades in the technology industry.

Publisher

Kevin Goldsmith

Category

business · education · technology

Language

en

Explicit

No

First episode

8 Jan 2024

Latest episode

11 Oct 2026

Latest episodes

73 episodes in the feed.

1. 

   11 Oct 2026

   Slight or Signal: Learning the Game at Work

   A leader is running an initiative, and at an executive meeting his boss gives three of his peers time to talk about it. He gets added at the end, almost as an afterthought. A few days later, Kevin Goldsmith had his own version: a meeting he’d contributed slides to went ahead without him. Both of them were reacting to the small part of the situation they could see. The obvious question is whether the boss meant it. The more useful one is how to read someone whose context you mostly can’t see. That starts with understanding the game, which Kevin defines as a company’s real system and culture: what actually gets rewarded, and how decisions really get made. Kevin draws on eight years at Microsoft that trained him to read every interaction as political, and a moment at Adobe when that wiring led him to badly misread his own boss. He lays out a five-step framework for telling a slight from a signal. It starts with separating what you saw from the story you told yourself, and ends with deciding whether the game is one you want to play. Along the way, he brings in logical empathy and David Foster Wallace’s idea of default settings. The episode also turns the question around. Managers create these moments for their own teams, usually through omission, and Kevin shares a time he got it wrong, and what he does now to close the loops his reports can’t see. It’s for engineering leaders who answer to a boss and have people answering to them. John Godfrey Saxe, “The Blind Men and the Elephant” (1872) Episode: “Every Organization Is a System. Are You Designing It or Just Living in It?” (Mar 2026) Episode: “Values → Culture → Everything: Why Company Culture Actually Matters” (Sept 2025) Chris Argyris’s Ladder of Inference Episode: “Logical Empathy” David Foster Wallace, “This Is Water,” Kenyon College commencement (2005) 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

2. 

   27 Sept 2026

   The Outsider's Audit: Due Diligence on Your Own Org

   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

3. 

   13 Sept 2026

   Paying for Nothing to Happen: Budgeting for Security, Compliance, and Reliability

   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

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

4 ratings

Spotify

5.0 / 5

7 ratings

Podcast Authority Score: 24 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

24

Social presence

0

YouTube

0

Engagement

60