1:1s

Unlocking potential by asking powerful questions

Morpheus and Neo from the Matrix, having their first “1:1” session.

One of my favourite movies is The Matrix, and the scene above sets the stage for the relationship between Morpheus and Neo: that of teacher and pupil. Morpheus is our battle-hardened design manager and thought provoker, and Neo is our young and promising designer / computer hacker.

Throughout the series we see Morpheus acting as a guide for Neo. He pushes Neo’s understanding with powerful questions to make him re-evaluate his reality and view of the world. He makes Neo “think” and draw his own conclusions before providing the secrets of the Matrix, and he “shows” him the ropes before throwing him into the deep end to fight the baddies.

By the end of Matrix, we see Neo transformed into a powerful and wise champion in the war between humans and machines, and we see Morpheus proud of his role in unlocking Neo’s potential, empowering him to “free his mind”.

What can we learn from this duo and apply in our 1:1s with our own teams?

A meeting that feels intimate

In the daily hustle of design reviews, Figma prototypes, or user interviews, I view 1:1s as a precious time to hit pause, slow things down, and reflect with my colleagues by zooming out. As a people manager I’m doubly lucky because I take part in 1:1s with both my direct reports and my own manager. I find being “in the middle” gives me a unique opportunity to view my team both top-down and bottom-up.

The nature of 1:1s is uniquely intimate. It’s two people, sitting down together (ideally over a coffee), free of distractions, with the goal of discussing topics of mutual interest. However, there is a power dynamic between the manager and the employee.

At first, it can be unbearable: “What do I say?”, “How do I not screw this up?”, “Is my boss evaluating me?”, “Does she even want to be here?” These are normal thoughts to have when a relationship between a manager and an employee is starting to take shape.

But as the relationship progresses healthily, we begin to have thoughts like “I’m stuck on this problem and I’d love a second opinion”, “I’m feeling anxious about this project and I want to talk about it”, “I’m not feeling engaged with my work and my manager needs to know about this.”

For this evolution to take place, for the relationship to truly bloom, we need to build a foundation of trust.

How do we build trust?

For me, it all starts with creating a personal connection. I love spending time with my team to understand what’s going on in their lives, inside and outside of work. “What’s the latest book you’re reading?”; “Send me a latest picture of your furry friend!”; “You got engaged, I’m so excited for you, tell me how it all went down!; “How’s the new gym routine going?”;
”What was the highlight of your vacation?”; “What went well last week, what was your biggest win?”

Building trust is about showing up with genuine care, energy, optimism, empathy, and curiosity. I somethings think of it as playing the role of workplace anthropologist. It’s about providing value before asking for value. It’s about slowing down, spending the time, and listening, cutting out all the noise around us.

Building trust takes time, it doesn’t happen overnight. But once a foundation of trust is established, we can then focus the conversations and start challenging each other.

Structuring the meeting

In meetings with direct reports, I strive to break down my role between that of Manager, of Coach, and of Peer. This helps me cover a wide spectrum of topics, and I can flex into a different mindset depending on the agenda.

Manager

My priority as a Manager is to provide feedback to designers on how they’re performing on the job. Here I’m looking at their work on a weekly basis, and coming prepared with 1-2 observations. This can be about how they ran a design review, how they applied a method for user research, or how they’re practicing a soft skill like communication with their teams.

Another area I like to focus on is uncovering concerns or issues. What is happening in my employee’s work life that may be causing lack of motivation, boredom, a lack of engagement, or a feeling of not being heard or included? Here I’m looking for cues to potential problems that might be bubbling up, that I don’t know about, but that I should become aware of. Getting ahead of these issues can open a dialogue to understand and diffuse problems before they escalate.

Coach

As a Coach, my mindset shifts from the short-term to the long-term. Here I’m looking to support my team members progress towards their career goals. I’m interested to learn from my team what expertise they want to level up on or skills they want to improve on. We can review current role and responsibilities, and look for adjacent areas outside of their role they could be contributing in. These types of discussions are great for me to start playing matchmaker, to pair new projects or areas of the business with my employees’ need for growth.

I’m also curious to check in on how much feedback and direction they want from me. More feedback or less feedback? More direction or less direction? Here I try to bring up recent situations and role-play how they could’ve handled them differently, what they would change, and what expectations they have from me going forward.

Peer

As designers we naturally love to talk about the work itself: the design process and artefacts. I spend a lot of time with my team as a Peer in order to make them comfortable to discuss their work, to verbalize their design rationale, and to discuss their plan of action. Here I’m interested to continue fostering a personal connection with my team. If my designers feel they have my trust and genuine curiosity in their work, they can be at ease to discuss challenges they might be facing. There’s sometimes a pressure for designers to have the right answers all the time. My goal is to break that assumption down and say “Hey, it’s okay if you don’t have a solution yet. I trust your process. Let’s align on the goals and work backwards from there”.

Zooming out from the hands-on artefacts, I also like to spend time discussing they “why” behind a particular project, to ensure my designers understand how their work rolls up to business outcomes and are able to articulate this in their own words. This line of discussion is critical for me to ensure our expectations are aligned and we’re working towards the same end goals.

If a designer is stuck on a particular design decision, I also like to spend 10-15 minutes jamming together. Here I let them take the lead and I focus on asking questions, rather than suggesting a solution.

Leading with questions, not solutions

“I can only show you the door. You’re the one that has to walk through it.”
— Morpheus

Jumping back to the Matrix, this line illustrates the dynamic between Morpheus and Neo: the teacher-pupil relationship. Neo as the student must take the wisdom granted by his mentor and apply it in practice in order to grow.

I believe the key to unlocking growth is asking powerful questions. As a manager, my goal is to prep 3-4 powerful questions ahead of every 1:1. This is why having an agenda prepared in advance is important. Even more important is that the agenda is co-created and shared ahead of the meeting. Asking questions helps me understand or clarify a particular topic or challenge, and it creates space for my employee to reflect, build self-awareness, and build self-responsibility. The power of questions is magical! I often find my employees already have the answers to their problems, they just haven’t spent time to think through and verbalize them yet.

During my time at Properly, I was lucky to take part in 3x4 Coaching by Third Factor. Cyndie was an incredible facilitator and coach herself. I learned how to become an active listener and draw people out with the right questions, how to effectively give feedback, and how to challenge and confront individuals and situations. Here are some of my favourite questions that stuck with me that I often use in my 1:1s:

  • Open conversation: What went well this week? What’s exciting you?

  • Focus a conversation: What’s your #1 priority right now?

  • Ensure clarity: What will success look like? What is your next step?

  • Uncover issues: What’s draining your energy?

  • Build confidence: What did you learn? How can you share that?

  • Build accountability: What’s one step you can take today to move forward with this project?

  • Clarifying: Could you give me an example?

  • Reflecting: If seems you are feeling X about …

As a manager, these questions help me stay curious and accountable to my team, and more importantly, they help me create space for reflection where real insights and next steps are revealed.

Avoiding trust-killers

Nothing hurts more than feeling like your manager doesn’t care about you, is not interested in supporting you, or simply doesn’t want to be in the meeting. Here are some outcomes I’ve experienced that left me feeling unvalued, and ones I actively strive to avoid in my own 1:1s:

  • The 1:1 turns into a status meeting: Being put on the spot to give updates that can be done async leaves no space for rich discussion or hidden insights.

  • The 1:1 is always about solutions: If my manager has all the answers, then how am I going to learn by doing?

  • The 1:1 is derailed with distractions: Slack messages, emails, meeting reminders. It’s best to turn those off and focus on the conversation.

  • The 1:1 puts the onus entirely on the employee: The manager and employee have to co-create and own the agenda together. Otherwise the employee is always in the hot seat, and shows laziness from the manager.

  • The 1:1 is cancelled: This one stings the most. It signals “you are not my priority right now”.

It’s about the journey, not the destination

The people we spend time with can have outsized impact on our career journeys and journeys of self-discovery. Looking back on my career so far, I’m extremely fond of the intimate discussions I had with former managers during 1:1s. I know that these folks will always be there for me, a text or phone call away, many years after we worked together. Their care, compassion, questioning, understanding, and culture of support made a difference for me, and these traits are ones I personally strive to provide to my own designers.

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Coaching and managing people is a journey of its own. If you’re also a manager, I highly recommend following these folks that are experts in their domains and have often shaped my own thinking and reflection.