Delegate until it hurts: Give work to the capable people

[01:47] Introduction and Welcome

Andrew Murphy: Hello everybody and welcome to another Tech Leaders Launchpad Livestream. I'm Andrew Murphy, tech leadership coach and trainer, and founder of Tech Leaders Launchpad. This is a livestream where we talk about all things technology leadership. Like many of you, I started my technology leadership journey by being the longest-tenure engineer promoted into a leadership position without any understanding of what that meant. Back then, 15 years ago, I had no idea what I was supposed to do. I didn’t understand the difference between being a technologist and being a leader, and there were not a lot of resources out there to help people like me.

So when I got into the situation I'm in, I decided that I would help people like me. I want them not to take the 15 years to learn leadership that I took. I want them to learn it a lot quicker. So Tech Leaders Launchpad Livestream is all about sharing my coaches, my mentors with you, and discussing the topics that I think are important for new and emerging technology leaders to learn.

Today we're going to be talking about "Delegate until it Hurts" with Michael Lopp.

[05:28] Introducing Michael Lopp ("Rands")

Andrew Murphy: Welcome, Michael.

Michael Lopp: Thank you. It's lovely to be here, Andrew.

Andrew Murphy: You have such a storied history in leadership! I was LinkedIn stalking you before this and saw that you've been a leader since Netscape existed because you worked at Netscape.

Michael Lopp: That was job number three. I was at Borland before that. When I talk to an audience, I ask, “How many of you remember Borland?” It’s fewer and fewer hands every year, but Netscape—another great experience in my career.

Andrew Murphy: I was a Delphi programmer for a while, so I definitely remember Borland! That was big in my university time. Since then, you've also worked at companies like Apple, Palantir, Pinterest, and Slack. You've had a huge impact in those organizations, but you also share what you know with the community—your blog, Rands in Repose, you run the Rands Leadership Slack, you're all about giving back, which is amazing.

Michael Lopp: That's correct. That's what I do.

Andrew Murphy: So, you're joining me today to talk about delegation. If you’ve got questions for Michael or me, please post them in the chat, wherever you're watching—Twitch, YouTube, LinkedIn. If you have to drop off early, don’t worry; this is recorded, so you can watch it later. There'll be links at the end for the newsletter and YouTube subscription.

First, I want to clear up—because I'm going to make this mistake during the livestream—you have the online pseudonym “Rands.” Where did that come from?

[07:30] The "Rands" Persona and Having Multiple Work Identities

Michael Lopp: As I’ve mentioned, I've been doing this for a long time. Back in the day, before a lot of the social networks and everything, it wasn’t cool to use your real name online—you had a pseudonym. One day, logging into a chat room with friends at Netscape, every time you logged in, you would make up a new name—something disposable you’d use for a year and never again. Point number one, be careful what name you pick. Point number two, it’s my wife’s maiden name at the time. Point number three, I did not intend it to become the thing that turned into books, blogs, T-shirts, all that.

But it’s a convenience: if you call me Rands, I know it's the Internet guy. If they call me Lopp, it’s the person who works at Apple. Michael—that’s family. Mike—that’s my dad and he’s mad at me. So, I have all these names, kind of early warning systems.

Andrew Murphy: That’s fascinating! It’s like being clear on the persona that the person expects. Do you feel you have a separate persona as Rands versus as Lopp?

Michael Lopp: A little bit. The Rands person is a little snarkier, a little bitter, you know? I was just thrown into leadership, and nobody told me what to do—there were no books, nothing. I was bitter for the first five years, but then I turned around and thought, “Cool, I can be the helper.” There’s that snarkiness, but he’s smarter than me too—part of the writing persona.

Andrew Murphy: I love that you describe Rands in the third person. When I’m presenting publicly, people expect that persona, but when they meet me outside that environment, they realize I’m a demure introvert.

Michael Lopp: Same for me! Public speaking—all hands, conferences—is work. It's a manufactured persona: I know I need to be engaging, nodding, looking in the right spot, but mostly I want to hide under a table and play Zelda. It’s not duplicitous, but it’s literally a hat I wear.

Andrew Murphy: Yes, I wouldn’t say something I disagree with, but I do kind of turn my opinions up to 11. For public speaking, it’s truly entertainment.

[12:05] Setting the Stage for Delegation

Andrew Murphy: Let's segue into delegation. When I invite guests, I ask: "If you could implant a thought into every new tech leader’s mind, what would it be?” You said, “Delegate until it hurts.” Why is that your answer?

Michael Lopp: It’s a rich topic. Becoming a manager/leader isn’t just a promotion, it's a brand new job with skills that are the opposite of what made you great as an engineer. We engineers love control and influence from building things, but as a manager, those habits hurt you—you now have to let go, influence at a distance. Letting go is hard for engineers; that's one of the first three-years lessons as a manager.

Andrew Murphy: There’s also the element that you’re good at engineering, you derive value from it, and now you’re told not to do it anymore. It’s a big mindset shift to do something you may not be good at yet.

Michael Lopp: Even if your instincts are good, something’s going to blow up, and you'll be in fight-or-flight mode. When your team is failing, as a brand new manager, most regress: you jump in, write the code, try to fix things, but this demoralizes the team, blocks them, and confuses them. There’s real downside to that, and the signal and optics matter—even if you save the day, you’re not seeing what your team sees.

Andrew Murphy: You're building a hero culture, which isn’t healthy.

Michael Lopp: Super bad.

[18:11] Leadership Without the Title

Andrew Murphy: There’s another important aspect: you can be a leader without being a manager. Staff and principal engineers are leadership positions, even if they're not management.

Michael Lopp: Leadership comes from everywhere. Yes, manager is a role, but leadership can come from anywhere. I love seeing engineers step into management, then realize six months in that it’s not the right fit—that’s a success in itself. You can go back to being an engineer and still have influence.

Andrew Murphy: A joke I make when training: you can see who the leader is—just break production! Everyone swivels to one person, no matter their job title. (Not advocating you break prod.)

Michael Lopp: That happened at Slack! First or second day, Slack went down, open seating area—everyone looked at Cal Henderson, the CTO. He was the one typing frantically, fixing the problem.

[19:19] Practical Example: Delegation in Action

Andrew Murphy: Back to delegation—can you give an example where delegating elevated the team or culture?

Michael Lopp: At Slack, I built a promotions process, drawing from previous experience. I thought it was good, but the next year, I delegated it to a group of new directors. I really wanted to do it myself, but by delegating, they improved it beyond what I could have done, fixing issues I hadn’t seen. Now the process is theirs and benefits thousands. Even if they only “get a B” the first time, that’s huge, because it’s theirs: they learn, gain trust, and get the experience. It's hard for engineers to let go, but it's critical.

There are also times you have to micro-manage and dive in, so it’s not always “delegate everything.” Sometimes, you have to taste the soup and figure out what's broken, especially when you have to operate at a high altitude.

[23:10] Delegation Decision Models and Assessing Tasks

Andrew Murphy: How do you identify tasks to delegate? What’s your decision model?

Michael Lopp: Depends on the person and where they’re at. For new managers, some still code with their small team—fine. If you want to grow at scale, though, you have to be able to delegate. I assess if someone is capable of delegation—when things explode, do they jump in, or do they pull together the team to solve it? Dive-ins are fine occasionally, but if they always do it for the “hero” feeling, it’s a problem. There’s a diagnosis to see where someone is on their delegation journey.

Andrew Murphy: Sometimes you just feel you’re the best person to handle something. That itself is a signal—maybe you need to upskill your team or reevaluate your perspective.

Michael Lopp: There are scenarios—like with a small team—where hands-on is totally fine; different strategies for different folks.

[26:44] Avoiding Overload Through Delegation

Andrew Murphy: If you love delegation, you can overload high-performers. How do you avoid that?

Michael Lopp: You need to assess task complexity and the person’s capabilities. Ideally, it’s a stretch assignment. If it’s too hard, people will stall or not ask for help, so I check in regularly: “What’s going on?” Offer advice and nudge as needed. Silence is almost always a bad sign. When there’s no progress, it’s time to check in, not to be adversarial, just attentive.

Andrew Murphy: Even if someone is asking questions, that’s good feedback; silence could mean confusion, deprioritization, or fear.

Michael Lopp: Another warning sign is when someone responds, but there’s no substance—restating the problem without progress. That’s as bad as silence.

[29:10] Staying Technical & "Soup Tasting"

Andrew Murphy: Sometimes, even as a leader, diving into the weeds is valuable—like Ben found an environment mismatch by helping a team. How do you view staying technical?

Michael Lopp: It's important as a technical leader for credibility and situational awareness. If you always swoop in, it’s no good, but soup tasting—occasionally testing things yourself—keeps you connected. It's important to show some technical knowledge, even if not deep.

Andrew Murphy: I see it as understanding the puzzle pieces and how they fit, not the intricate command lines. As a director with broad responsibility, knowing the trade-offs and interdependencies is key, not the granular details.

Michael Lopp: Yes, and with delegation, it goes both ways: you delegate, but also expect returns—updates on how things are going, maintaining bidirectional communication.

[34:28] Managing Complex Delegation: Chunking and Communication

Andrew Murphy: For higher-risk projects, what about chunking delegation and setting communication expectations?

Michael Lopp: With big projects, you often have to split responsibilities. The critical trick is not just delegating the pieces but also appointing someone to synthesize everything at the next level up—the “membrane” bringing back the status. Keeping a map of accountable individuals (not just teams) who know and can communicate the state of their “chunk” is crucial.

Andrew Murphy: I like that—focusing on people, not just teams. The leader may not be the manager.

[39:43] How Much Should a Manager Know?

Andrew Murphy: James asks: If a manager can explain implementation details as well as the doers, is that a red flag?

Michael Lopp: It’s situational. With a small team, sure. At scale, not knowing the details can backfire—your team doubts your understanding. But being lost in every detail means you're likely over-managing. Everybody should have defensible opinions about their work.

I divide my job between QA (sniffing out what's broken) and investigative journalism (finding out what’s going on and being able to explain it). The key is to balance being informed with letting go.

[41:04] From Outputs to Outcomes

Andrew Murphy: Leaders should focus on outcomes, not just outputs—on the change they make in the world, not just code produced.

Michael Lopp: Totally agree! Focusing on change and empowering the team is much healthier.

[43:06] Measuring Delegation Success

Andrew Murphy: How do we measure success in delegation? What signals show our framework for delegation is working?

Michael Lopp: Think about two things:

1. Did you truly hand it off? Not jump in mid-way and fix things yourself.
2. Are you still well-informed? Have you built trust so your delegate keeps you updated? You want to be as informed as if you did it yourself.

It's not about abandoning the task—you're still accountable and need to gather context at a distance. Some new leaders think delegation means zero accountability, but that's a mistake.

[46:45] Being Accountable While Delegating

Andrew Murphy: I made that mistake—thinking “manager-of-managers” meant total autonomy for my teams, but you must still know what's happening. Operational support and understanding are core, especially as teams scale.

Michael Lopp: Yes, as a senior leader, you need a communication cadence and contract with all your teams so you can answer what's going on without micro-managing. When a senior exec “soup-tests” you, you need to have the info. If your boss bypasses you, that's an anti-pattern—maybe you’re missing signal, or maybe your boss isn't delegating properly.

Andrew Murphy: If your boss keeps bypassing you to go directly to your teams, that's strong feedback—even if it’s wrong, it's still actionable.

Michael Lopp: I can sense when feedback is coming; over time, you learn to listen, not get mad—just analyze. That’s a senior leadership skill—you get less praise, more feedback, and need to just listen.

[52:20] Mindset Shifts for New Leaders

Andrew Murphy: If you’re a new leader who feels “I can do this job better than my team, delegating is a waste”—how do you change that mindset?

Michael Lopp: Ask yourself: what’s your dream for your job? Why did you want to become a leader? Often, it’s about having more influence, doing more. To scale influence, you must operate at a distance; you must delegate. I personally miss code, but I write to scratch that itch—building product at scale requires empowered teams, which only delegation allows. If you want to scale yourself, delegation is a core skill to develop.

[55:12] Closing and Next Steps

Andrew Murphy: Thank you so much, Michael, for joining! That was an amazing conversation. For everyone watching, our next livestream is in a week with Claire Sudbury on onboarding juniors. The time is rough for Australians, but it’ll be worth it.

If you’re on YouTube, hit subscribe; on LinkedIn, follow me; on Twitch, sign up for the newsletter.

Michael, anything you want to plug?

Michael Lopp: The Rands Leadership Slack! 32,000+ leaders helping each other. Just type "Rands Slack" into your browser to get started. One of the things I’m most proud of.

Andrew Murphy: It’s a great resource, a community with a huge mindset shift. If you want to learn more about me or Tech Leaders Launchpad, follow the links and subscribe. Thank you again, Michael Lopp aka Rands. I enjoyed our conversation immensely.

Michael Lopp: Thank you, sir.

Andrew Murphy: See you, everybody!