https://leegold.com/tags/leadership/ Recent content in Leadership on Lee Goldsworthy Hugo en-au Tue, 01 Sep 2026 18:00:00 +0800 https://leegold.com/posts/2026-is-the-year-of-feeling-like-youre-falling-behind/ Tue, 01 Sep 2026 18:00:00 +0800 https://leegold.com/posts/2026-is-the-year-of-feeling-like-youre-falling-behind/ I’m calling it: 2026 is the year of Feeling Like You’re Falling Behind™. “Who thinks they’re falling behind right now?” I asked on Thursday. The room was comprised of tech folks: A mix of CTOs, VPs of Engineering, Founding Engineers, and Senior Engineers. They all had prior experience doing AI Engineering, yet every single one of them (including me) put their hand up. The better question is “What are you going to do about it? https://leegold.com/posts/why-arent-we-shipping-faster-with-ai/ Tue, 16 Jun 2026 18:00:00 +0800 https://leegold.com/posts/why-arent-we-shipping-faster-with-ai/ “Why aren’t we shipping faster with AI?” is the dominant question I’ve seen up-close from 13 (and counting) Boards and Executive Leadership Teams to CTOs of software scale-ups this year. “If tomorrow we were to go twice as fast with our current setup, we’ll have twice the Sev1 incidents, twice the bugs, and twice the undiscovered security vulnerabilities” is the completely reasonable pushback I see, but turning that pushback into a constructive leadership conversation about resource allocation is what I’m interested in. https://leegold.com/posts/the-bottleneck-just-moved-to-the-leadership-team/ Tue, 24 Mar 2026 18:00:00 +0800 https://leegold.com/posts/the-bottleneck-just-moved-to-the-leadership-team/ Over the next 1-4 months, every Senior Engineer can have output equivalent to a whole team in 2025. This moves the bottleneck to Product/Engineering Leadership and the CxO team. We’re going to need organisational change; Level 4 Agentic Orchestration is just shining an even brighter light on what we’ve always known was central to success: Clarity of purpose, and shared understanding. Yes, there’s still real work to do in Engineering teams to embed the L4 Orch tech, but it’s now obvious to me there’s even more change required in Senior Leadership / Executive teams to get traction with all this new horsepower, otherwise it’ll just be a lot of spinning tyres. https://leegold.com/posts/how-i-run-zero-inbox-as-a-fractional/ Mon, 24 Nov 2025 18:00:00 +0800 https://leegold.com/posts/how-i-run-zero-inbox-as-a-fractional/ As a Fractional, my Attention Management has to be brutal, and a friend recently asked me to describe how I run my Zero Inbox. it’s a blend of Eisenhower Matrices and recurring Ceremonies I use to manage the noise from working with 4-6 startups at a time (often with inboxes, calendars, chat and project tools for each), so I figured I’d share it here. Core Principle: “I should only see things I need to do that Hour, that Day, or that Week (in that order), everything else should resurface at the right time without me thinking about it” https://leegold.com/posts/a-30-second-risk-check-before-you-click-i-accept/ Mon, 06 Oct 2025 18:00:00 +0800 https://leegold.com/posts/a-30-second-risk-check-before-you-click-i-accept/ I get FOMO when looking at the promised productivity gains from all these amazing-looking new platforms I hear about every week (each bearing enticing promises of automating this or that generic administrative task), but I find myself regularly holding back from using them against the backdrop of not opening myself up to unreasonable security and privacy risk. Here’s a practical example of how I did a 30 second risk sanity check for one I was about to try out earlier today that wanted access to my inbox, which is a big red flag for me: https://leegold.com/posts/being-wrong-out-loud/ Mon, 18 Aug 2025 18:00:00 +0800 https://leegold.com/posts/being-wrong-out-loud/ When you’ve (recently in my case) been objectively wrong (and publicly so), do you get the most out of the opportunity? I was hanging out with my in-law’s over the weekend, and I said (with a lot of conviction) something at Saturday lunch I was confident was true. Upon reflection the next day, I realised I had learned the relevant “fact” so long ago that it was prior to me having usefully developed standards of evidence. https://leegold.com/posts/curiosity-is-the-job-security/ Mon, 30 Jun 2025 18:00:00 +0800 https://leegold.com/posts/curiosity-is-the-job-security/ Your knowledge worker job will likely evolve significantly in the next 5 years. You’re probably fine if you’re the curious type who constantly experiments with your workflow. If not, I reckon you’ll struggle. The most effective people I know are more productive now than ever, many leveraging LLMs. But their curious mindset would drive progress even if ChatGPT didn’t blast onto the scene in November 2022. This echoes a core tenet of the agile frameworks: Continuous Improvement. https://leegold.com/posts/from-why-are-we-doing-this-to-how-we-measure-success/ Tue, 25 Mar 2025 18:00:00 +0800 https://leegold.com/posts/from-why-are-we-doing-this-to-how-we-measure-success/ There’s a progression in a Software Engineer’s career, but the job title doesn’t really help us to understand the broader journey. Jnr/Mid SWE is about Applications and Infrastructure Snr/Staff SWE you add People and Delivery HoE/CTO you add Strategy, Culture and Risk There’s a through-line in all of these, that grows in intensity through the progression: As a Jnr/Mid, we learn to ask “Why are we doing this?”. You know, “Tell me about the problem we’re solving, or the benefit we’re hoping to get”. https://leegold.com/posts/two-hours-two-days-or-two-weeks/ Tue, 04 Feb 2025 18:00:00 +0800 https://leegold.com/posts/two-hours-two-days-or-two-weeks/ “Can we drop what we’re working on and focus on this URGENT thing please?” …is a phrase all Engineering Managers and Tech Leads hate hearing. The reflex is to say “We don’t have time / we’re too busy for that”, but it’s an antipattern. The strong pattern looks like this: “Here’s three approaches to what you asked for: 2 hours (20% of the value), 2 days (40% of the value) and 2 weeks 80% of the value). https://leegold.com/posts/effort-size-and-fidelity-three-definitions-to-agree-on-day-one/ Tue, 17 Dec 2024 18:00:00 +0800 https://leegold.com/posts/effort-size-and-fidelity-three-definitions-to-agree-on-day-one/ When I land in a new startup/scale-up, I want to have fast and deep conversations with their product and engineering teams, and have everyone walk away with a highly converged understanding at the end of the chat. In service of this, there’s a few types of information I always find useful to get a handle on right at the start: Their internal naming conventions for foundational concepts that product and engineering rely on every day. https://leegold.com/posts/break-the-rewrite-cycle/ Tue, 29 Oct 2024 18:00:00 +0800 https://leegold.com/posts/break-the-rewrite-cycle/ Been there, rewritten that. Every software engineer has imagined an amazing rewrite that breathes new life into a legacy codebase/stack, but let’s be honest: Some rewrites feel destined for a repeat – the Groundhog Day of software dev. What’s the Cycle? Tangled legacy code tempts engineers to start fresh, followed by a lack of stakeholder buy-in, rosy estimates, and scope creep leading to half-baked rewrites that become the next rewrite target before they’re even shipped. https://leegold.com/posts/non-tech-leaders-champion-security/ Mon, 27 May 2024 18:00:00 +0800 https://leegold.com/posts/non-tech-leaders-champion-security/ Park your car in a bad suburb, leave your laptop on the passenger seat, leave your keys in the ignition. What happens next? The above is akin to what I often see in tech-enabled early-stage companies with respect to their security and privacy practices: Dangerous sh*t that’s going to result in loss and sadness if some changes to skills and awareness aren’t made. Here’s a real-world example of what I consider to be some of the best “everyday security culture” being put into practice by a non-tech leader at one of my clients: https://leegold.com/posts/cancel-your-performance-reviews/ Mon, 05 Feb 2024 18:00:00 +0800 https://leegold.com/posts/cancel-your-performance-reviews/ …or shrink them into insignificance Link to heading Having a spectacular manager early in your career is a kinda profound experience. They somehow see you, understand your goals, weaknesses and likely some of your neuroses too. What they never do is learn those things while you are both awkwardly filling out Likert scales and quibbling over Key Results in the HR-supplied Annual Performance Review template. Nobody likes peformance reviews, and for many folks they’re straight-up anxiety inducing. https://leegold.com/posts/hard-feedback/ Wed, 11 Oct 2023 18:00:00 +0800 https://leegold.com/posts/hard-feedback/ It’s all about trust Link to heading I came across this Julie Gurner quote today: “People can take hard feedback if they know you are in their corner” The first thing to note here is that praise needs to be a tool in your toolbox. If none of your feedback is praise, then you should read Radical Candor by Kim Scott asap. Assuming that you’ve got that nailed down, sadly not all your feedback can be praise, but the trick to getting good mileage from the critical kind of feedback is a symptom of how much trust you’ve built in the preceding months and years.