Done Right, 1:1s Are a Secret Weapon

I think it’s a common misconception in startups that constant proximity or daily stand-ups cover everything. But for me, casual daily interactions aren’t the same as intentional one-on-one conversations. And to me, this is the important part – intentional conversations. So many conversations at work are transactional – about deadlines, commits, code bases, sales and so on.

It’s too easy for intentional dialogue to get sidelined.

Early-stage startup teams are often described as being like a small family. You know, everyone working in the same room (or Slack channel), constantly chatting and problem-solving together. In such a tight-knit environment, formal one-on-one meetings (1:1s) might seem redundant or “too corporate.” But the reality is that even if you’re all working side by side and talking every day,  1:1s should still be happening.

Why 1:1 Meetings Matter. Even in a Startup Team

“We talk all the time, do we really need 1:1 meetings?” I’ve heard this, or a version of this, more times than i can remember.

There’s a whole bunch of benefits to having these discussions, off the top of my head:

• Surfacing Hidden Issues: It’s too easy for team members to suppress personal frustrations or concerns beneath the hustle. Regular 1:1s create a safe space for those issues to come out. As Groove’s founder discovered, without dedicated check-ins, “it’s easy for things to go unnoticed”, an unhappy employee can hide their discontent, and important problems go unsaid. Over time, a culture where concerns stay unspoken can become toxic. Dedicated 1:1 meetings ensure important issues aren’t swept under the rug.
• Building Trust and Openness: Startups run on trust; you need to know your team has your back. One-on-ones are a major avenue to build deep trust between leaders and team members. In a hectic daily grind, you rarely pause to learn what people really think or feel. A well-run 1:1 lets you truly get to know your colleague beyond the code or KPIs – “there’s a difference between ‘working with’ and ‘knowing’ someone, and 1:1s bridge that gap. This trust fuels honesty.
• Engagement and Retention: Startups can’t afford to lose great people. Effective 1:1s strengthen the manager-team member relationship. AKA: the single biggest driver of employee satisfaction and retention. When team members feel supported through regular check-ins, they’re more engaged and less likely to quietly disengage or leave. One study of 4,000 workers found that employees crave more 1:1 time with their managers, preferring weekly 1:1s, and those who get them report higher engagement. Conversely, skipping 1:1s can leave people feeling disconnected and unsupported, which is a surefire recipe for turnover in any company.
• Preventing “Blow-ups” and Surprises: In the whirlwind of a startup, small problems can fester into big crises if unnoticed. Regular one-on-ones act like a radar system for managers. By listening closely in 1:1s, a leader might catch an innocent remark that signals a looming issue – the kind of early warning that prevents fires before they start.
• Alignment on Goals and Strategy: In a small company, everyone wears multiple hats. It’s easy for priorities to misalign as each person charges ahead. Use 1:1s to ensure each team member sees the “why” behind decisions and how their work ties into the bigger picture. These meetings are a chance to reiterate the vision and adjust the course one person at a time.
• Growth, Feedback, and Development: Day-to-day chatter tends to be task or transaction-focused (e.g. “Did you deploy that fix?”). What gets missed is high-level feedback and career conversation. 1:1s fill that gap. These meetings are where managers can help team members grow by discussing long-term goals, giving constructive feedback, and jointly solving problems in a low-pressure setting. Over time, this leads to higher performance and a stronger team.
• Leaders Get Better Too: 1:1s aren’t just about the team member – they’re also a mirror for founders and managers. In a private conversation, a direct report may feel safer to offer you feedback on your leadership. It might take time to build that openness (initially, everyone might say “everything’s fine”), but a savvy startup leader will use one-on-ones to ask “What can I do better as a manager?” and genuinely listen. This kind of upward feedback is gold for a founder trying to grow alongside their company. Remember, in a flat startup culture, titles matter less – learning and improving together matter more.

So, intentional 1:1 meetings provide value that everyday interactions simply can’t match. They create space for honesty, trust-building, personalised mentorship, and proactive problem-solving. It’s no accident that so much of the tech industry has adopted 1:1s as a basic management habit, and teams that do regular one-on-ones are “far more effective” than those that don’t.

Formality vs. Authenticity: How to Keep 1:1s Useful (Not Stuffy & Inauthentic)

One concern startup leaders raise is that formalising 1:1s could introduce bureaucracy or awkwardness. The key is finding the right balance between structure and authenticity. I think that ideally, these meetings should be productive and purposeful, but still feel natural, especially in an informal startup environment.

Here are some thoughts on how to strike that balance:

• Create a Comfortable Setting: Don’t hold your 1:1 in the most formal, intimidating setting possible. If you’re in person, consider chatting over coffee or in a casual meeting area instead of across the CEO’s desk. If on Zoom, ensure it’s a video call where both parties are at ease (maybe encourage headphones and a chat in a virtual “coffee” vibe). The idea is to make it comfortable for your teammate to speak freely. A private, confidential space is essential so they know they won’t be overheard. Some managers even do walking meetings in the park or go out for lunch for a change of atmosphere. When people are at ease, authentic conversation flows.
• Keep It Casual, But Respectful: One-on-ones should feel like a conversation, not an interview or a tribunal. Casual doesn’t mean unprofessional; it’s a friendly discussion. With a purpose. As one guide put it, there should be no doubt who’s in charge, but the vibe must be “casual enough to encourage honest feedback”. Encourage your team member to speak openly, even criticise upward, without fear. That might mean explicitly saying, “This is your time, so feel free to bring up anything, even if it’s about how I or the company can improve.” When employees see you genuinely want their perspective, it builds mutual respect.
• Avoid Stuffy Formalities: You’re not required to have a rigid script. While you might have a notepad or an agenda, explain that it’s for them, not some HR formality. Co-creating an agenda can make it feel collaborative rather than top-down. Research shows one-on-ones are most valuable when both people contribute to the agenda. So you might say, “Hey, jot down anything you want to discuss and I’ll do the same; we’ll tackle what matters most.” The structure (a few bullet points, regular schedule) provides reliability, but the content should be genuine and tailored each time.
• Be Authentic and Human: Remember, a startup is a human venture. Show that in your 1:1s. It’s okay to acknowledge if things are hard or you don’t have all the answers. If you’re having a tough week, you can share that;  it invites team members to do the same. Authenticity breeds trust. On the flip side, listen intently when they talk and validate their experiences. If an engineer says they’re frustrated with a project, resist the urge to be defensive or overly formal; respond like a supportive colleague: “I get it, that sounds frustrating. Let’s figure it out together.” Being real with each other makes the 1:1 meaningful instead of feeling like a check-the-box exercise.
• Maintain Professional Boundaries: Balancing casual and formal also means knowing where the line is. You can be friendly and even joking, but remain respectful and focused on work-related topics. Team members should know that it is about them and their growth at work. As a manager, you’re still the leader in the room & your role is to support and guide. The guidance from HR experts is clear: don’t become so buddy-buddy that you undermine your authority or the meeting’s purpose. Think mentor, not pal. You can care about them as people (and you should), but also provide direction and hold them accountable. In practice, this might look like: warmly asking how they’re doing, laughing about a shared team joke, then transitioning to, “Alright, let’s talk about your goals for this month. How can I help with those?” Friendly and focused.
• Adapt to the Individual: Authenticity means recognising each team member’s style. Some people open up with a bit of small talk; others prefer getting straight to the issues. Some may be shy at first in 1:1s, requiring you to gently draw them out; others might come with a long list of topics. Tailor your approach. For example, with a more introverted team member, you might send questions in advance so they can reflect and feel prepared (reducing any formal “on-the-spot” pressure). With an extrovert who chats with you 10 times a day, you might use the 1:1 to dig a layer deeper than the usual banter (e.g. “I know we talk code every day, but I’d love to hear how you’re feeling about your workload lately”). In remote teams, someone who’s quieter on group Slack might actually open up one-on-one if you give them the space. Meet people where they are to keep things genuine.
• For Remote Teams – Be Extra Intentional: In distributed startups, those hallway chats and quick coffees don’t happen and a lot of communication is highly transactional, so 1:1s carry even more weight. It’s crucial to hold them consistently (likely more frequently, such as weekly) for remote folks. Turn your camera on, minimise distractions, and maybe start with a personal check-in (“How’s life in [their city]? How was your weekend?”) since you don’t see them in person. Remote employees often miss out on the spontaneous interactions in-office teams take for granted, so the 1:1 becomes their main forum for getting feedback, expressing concerns, and feeling connected. Treat it as sacred time to bond and communicate. Also, consider time zones and schedules – show that you’re willing to adjust to make it convenient for them (that shows respect and authenticity too).

So I think that a great 1:1 is part business and part personal. It’s a structured conversation that is still two humans talking. You set a welcoming tone, ensure privacy and respect, and follow a loose agenda that keeps you on track without stifling honesty.

When done right, 1:1s can become something both sides look forward to,  a “meeting” that doesn’t feel like a meeting, but rather like a valuable check-in with a mentor/mentee or collaborator.

If you’re remotely interested in this, and honestly, why wouldn’t you be? Then here is some suggested reading and the sources of some of the data in this article.

• Turnbull, Alex. “How Regular One-on-One Meetings Saved Our Company Culture.” GrooveHQ Blog, on fostering openness and catching hidden issues early.
• Paterson, Kimberly. “One Meeting People Want More Of.” Leader’s Edge Magazine, citing research that employees across levels crave more 1:1s and detailing their ROI in trust, engagement, and performance.
• Chin, Cedric. “Why Conduct One-on-Ones When They Take So Much Of Your Time?” Management for Startups, explaining the critical reasons (preventing blowups, building trust, feedback, culture, retention) that make 1:1s worth every minute.
• Squadra Ventures Blog. “3 Templates for Running Great 1:1s at Your Startup,” by Margaret Roth, offers startup-specific tips like treating the 1:1 as the employee’s meeting and sample question frameworks.
• PRemployer. “The Elements of a Constructive One-on-One Meeting.” (Feb 15, 2022), advising on balancing casual tone with leadership, meeting environment, and tone management for honest dialogue.
• Forbes HR Council (Nicole Roberts et al.). “20 Reasons Why Employees And Leaders Make Time For One-On-One Meetings.” Forbes, Dec 2024 – emphasising one-on-ones as indispensable for trust, growth, and alignment on goals.
• Atlassian Team Playbook & Confluence 1:1 template, for practical agenda-setting and defining the purpose of one-on-ones in maintaining relationships and alignment (referenced concepts in guide).

I could write about the power of 1:1s all day, and given the chance, I probably would. For me, they’re the single most powerful meeting leaders can have.

In one of my old teams, before we did everything on laptops. I used to have a notebook for every team member, and I’d have it locked in a drawer. In every one-on-one, I would write down the things that we were talking about, the notes, the feedback I’d given, and I’d probably give some homework as well. Then each week we’d just get that out and we’d review what we talked about last week, discuss what had happened since then, and just keep progressing.

Good luck, and sing out if you need any help or want to talk further.

This is not a plug. I’m not getting paid for this, but I wanted to let you know that I’ve written most of this newsletter just by talking into my mic using a product called Wispr Flow. I’ll put the link here. You should try it. It might work well for you. https://wisprflow.ai/

I’ll be trying the Apple dictation program next and comparing the two. I’ll let you know how that goes in the next newsletter.

What I learned from Tanya Hyams-Young. Founder, AI Builder, and Curiosity Maximalist

Tanya Hyams-Young isn’t just building AI products — she’s been doing it since before the hype had a name. As CEO and co-founder of SourseAI, she’s seen the mood swing from “that sounds like science fiction” to “can we bolt ChatGPT onto everything?”

What struck me in our conversation wasn’t just her technical clarity, but it was how grounded she is in the messy realities of building and scaling a company where machine learning isn’t a gimmick, it’s the core product. She’s honest about the tension between vision and viability, and the kind of people it takes to build something real when the future’s still fuzzy.

Here’s what stuck with me:

1. Curiosity is the real differentiator in customers and hires. “Some people ask questions to disprove. The best ones go deeper.”

Whether she’s hiring or selling, Tanya looks for curiosity, the kind that doesn’t stop at ‘yes’ or ‘no,’ but keeps asking ‘what if?’ and ‘why not?’ Her best customers are the ones who dig into the data and want to understand the mechanics, not just the marketing.

Same with her team. Early-stage success came from hiring people who saw ambiguity as an opportunity, not a red flag. They weren’t hired to do a job. They were hired to help build a future.

2. Great AI products are built by more than data scientists “One data scientist does not make AI.”

Tanya’s quick to call out the myth of the lone genius. The products her team builds require glue roles like the engineers who think about stability, the domain experts who know the real business problems, and the scary-smart PhDs who can go deep.

AI product-building is a team sport. And if you’re not investing early in strong infrastructure and repeatable systems, you’re just setting yourself up to throw things away.

3. Vision matters — but so does clarity about the business “You can paint a product vision, but the business vision needs to be shared too.”

One of Tanya’s reflections was that early on, she spent a lot of time aligning people around the product — what they were building, who it was for, what the platform could do. But she wishes she’d also brought everyone in on the business journey — revenue levers, market milestones, and the trade-offs of scaling.

Turns out, people do better work when they understand the mechanics of success. Not just the mission, but the model.

Final thought: Tanya leads with empathy, precision, and the kind of hard-won clarity that only comes from actually doing the work. She’s building AI products that drive measurable impact, but more than that, she’s building a culture of trust, flexibility, and shared ownership.

“Fast is good. But fast and right? That’s where the real value is.”

The full pod will drop next week, but I wanted to give you a heads up about it. We had some slight technical issues on this end, meaning it’s not available right now. But it’ll be available for you next week.

But don’t despair, there is Podcast action for you today. But it isn’t really a new one. It’s an old one from lockdown times. Andrew Murphy and I spoke about the challenge of managing remote teams, which was new for most people then, and I think the dialogue that we had probably ties into some of the one-on-one stuff that I’ve been banging on about elsewhere in this newsletter.

You might want to check this one out. It’s a good watch. Andrew’s super smart and a lovely human, so this might be useful to you.

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Simon