Scaling up your co-founder conversations

Melissa Rosenthal
4 min readAug 4, 2021


Photo by Calum MacAulay on Unsplash

This week I was asked to provide a co-founding team with some advice on running their regular meetings. They’ve reached the point in their growth that digging deep into day-to-day operational issues is not helping the company progress. It’s starting to hold them back. At the same time, it’s not clear what they could or should be talking about when they come together.

In this situation, conversations may devolve into superficial, token efforts to connect or peter out altogether, overtaken by urgent day-to-day demands. The most tension-filled topics will likely go unresolved, leaving the team vulnerable.

I recommend that co-founding teams make intentional decisions about meeting cadence and frequency to match the pace of their business. There’s no “one size fits all” rule to follow when deciding how often to come together. Start with the reasons why you need to meet and co-design your habits from there.

As you begin to recruit a more experienced team, your meetings will probably transition from a co-founders meeting to a leadership or exec team meeting. You’ll need to clearly outline which hat(s) you want people to wear in each conversation. And don’t forget that the needs are likely to change over time, so it’s worth revisiting every so often to ensure that your system is still working.

When it comes to the topics of conversation for your exec team meetings, I recommend consistently focusing on:

1. Purpose & Strategy

Context is critical for any meeting. In the case of your exec team, talking about purpose and strategy creates the opportunity to ensure that everyone is making the right connections — connecting function to purpose, connecting outcomes to strategy, and connecting each team member to both. A strategy on a page can be a useful starting point to ask questions including:

  • Of the work we’re doing, what aligns with our strategy? What doesn’t?
  • If we’re working on projects that don’t align with our strategy, why are we working on them? How did they get prioritised? Should they continue?
  • What can we do to ensure that everyone in the team stays focused on how their efforts connect to achieving our purpose?

2. Culture

I know that conversations about culture can feel quite slippery and aimless. It can be hard to structure them in a way that feels actionable for the team. I recommend creating space for open conversations about team collaboration, conflict, decision making and prioritisation. As you grow, these are the places where culture adapts, and systems can break down. It’s essential to observe how these adaptations are occurring and manage them carefully. Your collective observations can be brought to light through questions such as:

  • What changes are we noticing in the way our functional teams are working together?
  • What decisions are being escalated to us (that we would expect to be made by members of our teams)?
  • Over the last month, how often have we needed to arbitrate decisions that our teams have been unable to resolve?
  • What blockages do we need to remove?

3. People

Often “people conversations” in exec teams focus on capacity — whether we have enough people to do the job. There’s no doubt that capacity is critical to the sustainable growth of your business — but it’s not all that’s required. There are also questions including:

  • Do we have the right people in the team?
  • Where do we have key-person risk? What is our plan for succession?
  • What does our org design or people map look like six months from now?
  • Should we recruit for our current or future needs?
  • Who do we need to thank for their fantastic contribution? Who needs a little extra encouragement?

4. Performance

When it comes to performance, the specifics and maturity of your business will likely determine your focus. For some teams, revenue and burn rate will be immediate priorities. Other teams will be more focused on customer numbers and the cost of acquisition. Still, others will be looking at production quality and the logistics of getting their product into customers’ hands. No matter which of these tops your list, alignment on metrics will help you all work together to manage the business successfully. You can do this by answering questions like:

  • What are our most important metrics right now? How well are we turning information into insight?
  • What are our thresholds of concern (upside and downside)? For each metric, what is the signal that we need to worry? What is the signal that we need to act?
  • What is our process for working together to address concerns? How do we identify and prioritise opportunities that result from the insights we generate?

5. Team Dynamics

This final category is the opportunity for your exec team to turn a mirror on itself. To consider how effectively you are collaborating. Questions designed to reinforce an open and trusting environment, such as:

  • On a scale of 1–10, how effective was our last meeting? What can we do to increase that number?
  • What are the most significant sources of tension in our team discussions? How is that tension helping us? How is it holding us back?
  • If we could change one habit or behaviour in the team, what would that be?
  • What have we learned over the last <month>?

Have I missed anything? I’d love to include your ideas so please email me and let me know!



Melissa Rosenthal

Executive Coach | Mentor | Advisor | Podcast Co-host Remote Control |