FounderFuel: Using better one-to-ones to boost your team

When we’re busy churning out deliverables and focused on working through the to-do-list as founders and startup leaders, it can be really easy for one-to-ones with our direct reports to just turn into task-focused status-updates. Or worse still, slashed from the week altogether. But this can create a deep disconnect. Goal-orientation can dwindle, progress can stall, and direction is lost. Multiply that across the whole team and you can see why so many scaling founders swear by effective one-to-ones.

By elevating one-to-ones to a priority position in your week and maintaining a clear focus for them, they can unlock team productivity, free up your time, and as a bonus, really build a genuine relationship with your people too. This makes team retention a natural by-product of the process – in fact employees who meet regularly with their line-managers are three times more likely to be engaged in their job (Gallup).

As always, we’ve been crowdsourcing ideas and hearing what works from those in our #FounderFamily. What’s clear is that effective one-to-ones are absolutely critical to that delicate balance we have as founders of relinquishing control, but still feeling fully connected as the team grows. So it’s worth the investment and we have a simple guide to make it easy.

The headlines:

The why

Better productivity, better prioritisation, better relationships = boosted team performance

The who’s who of one-to-ones

These meetings are all about them! It’s time for your direct-reports to air whatever is on their mind and get support and direction as they need it. As such, it’s worth keeping in mind that your direct reports do most of the talking and own the meeting. Your job as a leader is to nurture the relationship, coach them through any challenges and support their career development. To get started, there are some tried and tested structures for doing one-to-ones effectively which we cover below, then you can collaborate together to refine it to suit you both over time.

Put your coaching hat on

The true power of effective one-to-ones comes to life when we shelve that ‘doing’ hat we all wear so well and swap it for our coaching-leader hats instead. Team members view this time as their key opportunity to get valuable time with you to share their views and get feedback, so go into each session ready to engage those active listening skills we practise in FounderCircles and utilise those coaching questions. This is a mindset shift – in fact, many say it’s worth not even thinking about them as meetings at all – but having the mindset that it’s a time to get to know and support each of your direct reports instead. This really helps you get to know their strengths and development areas, which in turn helps you work with them.

The cadence

In short, 30-45 mins weekly or fortnightly for one-to-ones with fully on-boarded team members – ideally at the same time each week so it feels routine. Monthly means you’re spending less than 6 hours a year with a person – which is no time at all to build a genuine relationship and invest in the person that you want to stay in your team. Not only that, but weekly helps you steer priorities to match the rapid pace of change in a startup environment – keeping everyone in sync and avoiding resource waste. Plus, most founders find weekly one-to-ones result in fewer “I’ve got a question” distractions during the rest of the week too, freeing you up to focus on your own deliverables.

The structure:

Connect and check-in

Always start with connecting at an individual level – teams that do this perform better together, so commit to showing your interest in each of your direct reports as a person – finding out about hobbies / life outside of work etc. This is also a great chance to do a wellbeing check-in or a “personal weather report” – which then allows you to understand what might be driving a gloomy or sunny day. A few questions you could kick off with would be:

  • What would be your personal weather report for this week?
  • In the past month, what have you been happy about?
  • In the past month, what have you been less happy about?

Hot topics

Kick off the structured stuff by asking for what’s top of mind for them, so that this can shape the time you have. This really gives them the chance to air frustrations too and you get a genuine pressure check. 

The PPP:

Progress (or wins!)  

Perhaps the most important! We all know how we forget to take stock and celebrate what we’ve achieved in a fast-paced startup environment, and it’s no different for our teams. So starting here means they get chance to highlight any wins, progress on their goals and things they’re proud of from the last week. It helps you get a holistic picture on their contributions to the team, and feeds their motivation and resilience too.

This is also a great time to ask coaching-style questions about what they’ve learned – which nurtures a self-aware and proactive growth mindset in your team. Here’s a few coaching-style questions to utilise:

  • What have been your wins this week?
  • What are you proud of from the last week?
  • What’s been your biggest learning recently?

Priorities (or plan)

With the last week reviewed, shine a light ahead by hearing their plan for their week ahead. You can adopt coaching-style questions to explore if these priorities are inline with key goals and help them allocate their time effectively.  Given things change so quickly in a startup, this also gives you the opportunity to re-steer priorities for changing contexts and keep everyone in-sync and productive.

  • Talk me through your priorities for the week ahead
  • Looking at your commitments for the week, are these priorities realistic / how will make time for these priorities?
  • What areas of development are you planning to work on?
  • Is there anything I can do this week to help you achieve your goals?


Your role as an enabling leader is to help your team break down barriers and identify solutions, so this section is prime time for your coaching-style practise and the Empowerment Cycle. It also helps you identify holistic process and people challenges that you could improve at an organisational level.

  • What problems can we work through together to help you this week?”
  • What roadblocks are holding you back right now?
  • What is coming up that is concerning you for your priorities this week?
  • Is there anything that is slowing you down?


Creating a culture of ongoing feedback can start with your one-on-ones: Ask for feedback yourself, explicitly recognise great work done and progress made by your direct reports, and share ideas for their additional development too. This really keeps their career development front of mind, which shows you care about this to everyone in your team. It’s a good idea to intermittently get feedback on your one-to-one sessions too, in order to keep the format collaborative. Here’s a few questions to try:

  • What feedback should we cover today?
  • What can I do better?
  • What could I do or stop doing that would make it easier to work with me?
  • A positive thing I’ve noticed you doing recently is… the impact of this is…
  • How are our one-to-ones working for you?
  • What would make our one-to-ones better for you?

Team check-in

This could be a monthly addition for direct reports with no team, and a critical weekly addition for senior direct reports who have a team themselves. It’s all about you keeping your finger on the pulse of team dynamics. Exploring this with all your direct reports allows you to see the holistic challenges and opportunities at a cultural level. It is also a key opportunity to cover hiring and team changes with those that are line-managers too. Questions to use include:

  • How would you describe the team’s weather report this week/month?
  • What frustrations or barriers are holding the team back right now?
  • How can we make things better?

Quick questions

These could be all the random questions that they wrote throughout the week, important updates, or personal AOB items. Direct reports should lead, then you as line manager can share any additions that the direct report needs to know about. Some founders like to do this after the Check in at the start of the session, or here as an AOB-style wrap up.


Of course, wrap up every one-on-one by going over action items and takeaways – this would be led by your direct report to emphasise their ownership of their own role, but doing a 2-minute review at the end can catch any misalignments. Many of our founders keep track of these notes and actions in a shared Drive doc or Notion page which makes it really easy for referring back and preparing next week – but try to avoid typing these in the session as you lose the rapport-building conversational flow in your valuable time together.

The monthly bonus time

With fast-paced change, and ambitious team members, it’s key to keep a sense of career progression front on mind– not just something that gets looked at every 6 months. Studies show that 82% of people would feel more engaged at work if their manager showed greater interest in their career progression. So once a month, boost the one-to-one time to an hour and calve out time to include this. Here’s a few questions to choose from:

  • Where do you feel you’ve had the greatest impact this month on your projects / team / the company?
  • How have you made progress on the skills / behaviours you’re working?
  • What is getting in your way?
  • Are there any projects you’d really like to work on?
  • If you could improve one skill in the next three months, what would it be?
  • In the next month, what would you like to do differently from last month?
  • What would you like to learn?
  • Is there anything I could do to invest more in your growth?

Monthly check-ins can also inform your bigger-picture thinking too and inspire innovation ideas from everyone:

  • What do you feel is the biggest problem of our organisation?
  • What would you change about our product?
  • If you were me, what would you do differently?
  • Are there any aspects of our culture you wish you could change?
  • What can I do to make your work life better?

For all FounderCircle members, we’ve just launched the one-to-one template in the Toolkit – have a look here.

Written by Christina Richardson, founder at weare3Sixty
Founder coach & trainer | Startup exec-team coach | FounderCircle® creator & head-coach. Passionate about sustainable founder performance, wellbeing and the leadership transition from founder to C-suite.

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