7 People: Gardening Your Teams
This chapter is currently in draft form.
People management sits third in the hierarchy of leverage, but don’t mistake that for low importance. While strategy and structure create the framework for delivery, people execute within that framework. Get the people lever wrong, and even perfect strategy and structure won’t save you.
Before diving into hiring, development, and performance management, let me start with the most practical advice I can give you: cultivate a relationship with HR. I don’t care what you think about HR personally. We in technology have this extraordinarily stupid idea that HR is the enemy. They’re not. They’re not going away. And that relationship drives what you can accomplish everywhere else in people management. Without it, you’ll be hindered at every turn. With it, you’ll be supported when you need to make difficult decisions.
7.1 The Garden Metaphor
My general philosophy for people management is simple: think of your teams as a garden. You’re constantly growing, fertilizing, watering, and also pruning. Both activities are necessary for a healthy garden, and both are necessary for a healthy team.
You grow the people you can. You prune the people you can’t. This is a constant process, not an annual event tied to performance review cycles.
Which side you lean toward depends on your organizational context. If you’re leading a team of five people in a startup and your people are performing well, you won’t be pruning very often. If you’re managing 150 people in a larger organization, you’ll be pruning regularly. But you should always be growing.
The garden metaphor matters because it reframes difficult decisions. Pruning isn’t punishment; it’s maintenance. A gardener doesn’t prune a branch because they hate it. Some branches take resources without contributing to growth. Others grow in directions that harm the whole plant.
7.2 Growing People: Situational Leadership in Practice
For CTOs, growing people means growing managers. This happens through delegation: giving your direct reports ownership of meaningful work and coaching them through the experience using radical candor. Real growth comes from progressively handing over responsibility for systems, teams, and decisions that matter to the business, then mentoring them through delivery with frank, unambiguous feedback.
Delegation serves dual purposes: it develops your managers while returning bandwidth to you. Every responsibility you successfully delegate is capacity you regain to focus on higher-leverage work. But delegation without coaching is abdication. You must stay engaged through honest, direct conversations about what’s working and what isn’t.
7.2.1 Matching Your Approach to the Person
Effective delegation requires matching your approach to where someone sits developmentally. Hersey and Blanchard’s situational leadership model (Hersey and Blanchard, 1977) captures this: leadership style should vary based on the person’s competence and commitment for the specific task at hand.
A new manager facing an unfamiliar challenge needs direction: clear expectations, frequent check-ins, explicit guidance. You might delegate implementation planning but retain architecture decisions. As their competence grows, you shift to coaching: challenge directly, care personally, tell them when they’re making mistakes, ask probing questions, provide context. They might own team performance conversations with your active support.
Once they’re competent but still building confidence, you step back further. You’re available when requested, encouraging their decision-making, but no longer driving. And eventually, you reach true delegation: they own the outcome completely and come to you only for major decisions.
The mistake most CTOs make is treating delegation as binary: you either own something completely or hand it off completely. Effective delegation is graduated, moving through these stages based on the person’s development level for each specific responsibility.
Development opportunities emerge constantly: new teams need leadership, critical systems need ownership, major projects require coordination. Match the opportunity to the person’s development needs. The real leverage comes when your managers adopt the same approach with their teams. Make your managers effective at situational leadership, and that capability cascades through the organization.
7.3 Pruning: The Necessary Discipline
Firing isn’t optional in healthy organizations. It’s necessary maintenance. If you’ve never had to let someone go, either you’re incredibly lucky with hiring, or you’re not maintaining the garden properly.
This is where that HR relationship becomes critical. When you identify performance issues (and you will if you’re coaching actively), bring HR into the conversation early. Not to start a termination process, but to create a development plan with clear expectations and timelines. Your job is to decide whether to grow someone up or grow them out.
The mistake most technical leaders make is waiting too long. They hope problems will resolve themselves, or they work around poor performers instead of addressing them directly. This is unfair to everyone: the underperformer doesn’t get the feedback they need, the team carries extra load, and you burn political capital managing around the problem instead of solving it.
When pruning becomes necessary, do it quickly and cleanly. Drawn-out performance improvement plans rarely work and create anxiety for everyone. Help people transition out with dignity and support.
I still haven’t learned to do this well. After years of practice, I’m still trembly and useless after letting someone go. I schedule these conversations for late afternoon and take the rest of the day off because I know I won’t be good for anything else. I do it because it needs to be done, but most of the time I hate it. If you find firing easy, something is wrong with you. If you find it hard, that’s the appropriate response to ending someone’s livelihood.
Your ability to execute this depends on your organizational culture and your relationship with HR. Some organizations support quick, clean transitions. Others require extended documentation processes. Work within your constraints, but understand that prolonged performance management rarely benefits anyone.
7.3.1 When You Can’t Prune: Building Around Constraints
Sometimes, however, you’ll encounter people you simply cannot touch. Leadership may have explicitly or implicitly put guardrails around certain employees for political, historical, or relationship reasons. In these cases, getting angry or continuing to push for termination wastes your political capital and accomplishes nothing. Instead, you must adapt your organizational design to work around the constraint.
I once managed someone who was an excellent individual executor but had limited ability to influence others or scale their impact. Give them a clearly defined task and they would deliver solid work. But as the organization matured and the bar for senior engineers shifted toward influence and team impact, they became less able to meet expectations. They couldn’t mentor junior engineers, couldn’t lead technical discussions, couldn’t drive cross-team initiatives. These were capabilities that had become essential for their level.
Under normal circumstances, this would trigger either intensive coaching to develop those skills or a transition out of the organization. But this person was protected due to their relationship with leadership. The path forward wasn’t to fight that constraint; it was to design around it.
I crafted a specialized role that maximized their execution strengths while minimizing their need to influence others. They became our go-to person for complex, independent technical work that required deep focus but limited collaboration. I restructured team interactions so their work fed into the broader system without requiring them to drive consensus or mentor others.
This approach had real costs. Other engineers noticed the different standards. Some questioned the fairness, and they weren’t wrong to ask. It required difficult conversations about why different expectations applied. There’s no good way to handle those conversations; you handle them as best you can. But fighting an unwinnable political battle would have cost far more while achieving nothing.
The reality is messier than any framework suggests. You’ll recognize these constraints when you hit them. Leadership makes it clear through their actions, if not their words, that certain people are off-limits. Once you recognize that reality, redirect your energy toward what you can control: craft roles that contain the impact, design workflows that minimize dependencies, and focus your development efforts on the people who can grow.
These situations are frustrating. Accepting the constraint doesn’t mean you have to like it. But dwelling on what you can’t change depletes energy you need for the work that actually moves your organization forward.
7.4 The Balance of Growth and Pruning
The right balance depends on context. High-growth startups can carry some underperformers temporarily because roles are fluid and hiring is fast. Mature organizations need higher performance bars because there’s less room for passengers.
Context changes, and your approach must adapt. The engineer who thrived in startup chaos might struggle as the organization matures. The manager who excelled with a small co-located team might falter with distributed teams across time zones. This doesn’t make them bad employees. It makes them people whose fit with the organization has changed. Your job is to optimize for delivery, which means recognizing that what the organization needs evolves constantly.
Your technical organization never fires anyone. Your CTO claims they have excellent hiring judgment and strong team performance.
It’s probably not a sign of exceptional leadership; it’s more likely avoidance of difficult personnel decisions. Technical leaders often avoid firing, hoping problems will resolve themselves or working around underperformers instead of addressing them directly.
Ask your CTO about their approach to performance management. Look for clear processes, regular feedback cycles, and evidence of difficult decisions when necessary. If they can’t point to examples of people they’ve helped transition out, dig deeper. The goal isn’t arbitrary firing, but ensuring your technical leader understands that team health sometimes requires difficult decisions.
The people lever requires more emotional intelligence than the others. You’re dealing with careers, livelihoods, and human dignity. But approached thoughtfully, it becomes one of your most powerful tools for building delivery capability. You’re not just managing individuals. You’re cultivating the human system that executes your strategy within your structure.