Magical 1:1s

Every week, leaders across the tech industry sit down for their 1:1s. These meetings should be transformative moments where careers take shape and leaders emerge. Instead, they often devolve into status updates, technical debates, or worse, they become dreaded obligations that both parties endure rather than embrace.

While I've previously written about the importance of 1:1s in managing remote teams, today I want to focus on what makes these conversations truly transformative. After a decade of both running and receiving 1:1s, I've seen three anti-patterns emerge again and again, each more damaging than the last.

The first pattern starts innocently enough. “Let’s just quickly go through your tickets,” the manager says, diving straight into implementation details. Twenty minutes later, both parties leave feeling like they just went through a shorter, less efficient version of a daily standup. The real conversations - about growth, challenges, aspirations - never happen.

Another common pitfall emerges when technical managers can’t resist solving technical problems. The 1:1 transforms into a debugging session or architecture review. While technical mentorship has its place, using these precious moments for code review misses a crucial opportunity for deeper development. It’s like using a chef’s knife to open mail. It is possible, but entirely missing the tool’s true purpose.

Perhaps most insidious is when 1:1s become stealth performance reviews. Every discussion carries an undercurrent of evaluation, creating an environment where vulnerability and honest dialogue become impossible. People stop bringing up challenges for fear of judgment. Growth opportunities wither before they can take root.

These patterns don’t just waste time. They actively prevent the development of both leaders and their teams. Think of personal growth like compound interest. Small, regular investments yield exponential returns over time. A single great insight in a 1:1 can alter someone’s entire career trajectory. A new perspective on leadership, a crucial piece of feedback, or simply the confidence boost from being truly heard - these moments compound.

When these moments never occur, the engineer who could have become a great tech lead stays stuck in implementation details. The product manager with executive potential never develops their strategic thinking. Week after week, month after month, potential remains untapped.

From Status to Growth

Most managers approach 1:1s with good intentions. They want to help, to solve problems, to keep things running smoothly. Yet this solution-focused mindset is precisely what holds them back from creating truly transformative conversations.

The shift begins with accepting that your job isn’t to solve problems in these meetings. Your job is to develop the problem-solver sitting across from you. This means learning to sit with discomfort, to resist the urge to jump in with solutions when you hear about a challenge. It means trusting that your team member can find their own way forward, with your guidance rather than your direction.

I learned this lesson the hard way. Early in my management career, I prided myself on being the person who could untangle any technical challenge. My 1:1s were debugging sessions where I’d dispense wisdom and watch my team diligently take notes. I was helping, or so I thought. What I was actually doing was creating dependency, stunting growth, and missing opportunities to develop true leaders.

Think of it like teaching someone to fish versus giving them fish. When you jump in with solutions, you’re giving them fish. When you ask thoughtful questions that help them discover their own solutions, you’re teaching them to fish. The first approach feels helpful in the moment. The second approach changes careers.

The beauty of this mindset shift is that it doesn’t just transform your 1:1s - it transforms you as a leader. You start seeing development opportunities everywhere. Your questions become more powerful. Your impact becomes more lasting. And perhaps most importantly, you create the kind of environment where people can grow into their full potential.

A Framework for Transformative 1:1s

After years of running and receiving 1:1s, I’ve found that the most powerful conversations follow a simple but flexible framework. It starts before you even enter the room.

First, flip the ownership. The meeting belongs to your report, not to you. This means they set the agenda, they drive the conversation, they own their growth. Your role is to create the container, to hold the space, to guide rather than direct. When I first share this with new managers, they often worry about losing control. But what actually happens is they gain influence.

The framework itself rests on three pillars that help create this container: The Present Moment, The Near Future, and The Horizon. Think of these not as a rigid structure, but as areas to explore together.

While your report drives the conversation, your role is to ensure depth in these explorations. Sometimes this means sitting in silence. Other times it means asking questions that open new doors. The questions I share below aren’t a script - they’re examples of how to gently guide the conversation deeper when needed.

Start with The Present - not with status updates, but with energy levels and current challenges. Simple questions like “What’s on your mind this week?” or “Where are you feeling stuck?” open doors to deeper conversations. The key is to listen not just to the words, but to what lies beneath them.

From there, move to The Near Future. This is where you explore opportunities for growth and impact in the coming weeks or months. But instead of prescribing solutions, ask questions that help them discover their own path. “What would make the biggest difference in your current project?” “Where do you see your team getting stuck?” The goal isn’t to solve problems, but to develop problem-solving muscles.

Finally, look to The Horizon. This is where careers are shaped, where aspirations take flight. Too often, we save these conversations for annual reviews. But real development happens in small, regular conversations about the future. “What skills do you want to develop?” “What kind of leader do you want to become?” “What are your current career goals?” These questions plant seeds that grow over time.

If this seems like a lot to pack into a single meeting, you’re right. I rarely try to focus on all three pillars in the same conversation. Instead I portion them out so that The Horizon talk happens about every six weeks, The Near Future about once a month and the rest of the conversations deal with The Present Moment. This way whatever comes up in The Horizon talks should inform The Near Future which informs The Present Moment.

The framework also isn’t rigid. Every member of your team is different, so each conversation needs to have its own pace and style. Some months you’ll spend more time in one area than others. The key is to maintain the balance over time. That way you ensure that both immediate needs and long-term growth get attention.

Wrap Up

Whatever pillar I am focusing on with my team member, I always make sure to end the conversation with asking for feedback. You might not get it the first time, or even the fifth time, you ask. But stay with it and eventually your team member will realise that you too are looking for ways to improve.

Running great 1:1s is a skill, and like any skill, it develops through practice, reflection, and continuous refinement. The journey from good to great isn’t about adding more techniques or memorizing better questions. It’s about having the confidence to sit in uncertainty, to trust the process, to let solutions emerge through conversation rather than prescription.

You’ll know you’re on the right track when your team members start bringing bigger challenges to these conversations. Not just technical problems or project updates, but real questions about their growth, their impact, their future. When that happens, your report moves beyond sharing information. They’re offering trust.

The impact of these conversations often reveals itself months or years later, when you see someone step confidently into a challenge they once thought impossible. And that, more than any technical achievement or business milestone, is what great leadership is all about.

If you’re looking to transform your 1:1s from status updates into career-defining conversations, I’d love to hear from you. Schedule a free call with me using THIS LINK to explore how we can level up your leadership through better 1:1s.