February 24, 2021

How to coach your leadership team to greatness

Founders, as your company shifts from startup to scaleup, you need to change your leadership style. Here's how.

Gillian Davis

8 min read

As a company grows and evolves, a founder’s leadership style must evolve alongside it. The behaviours that make a great founder at the startup phase do not always scale well. 

One key step a founder of a scaleup must make is shifting from being the performer to being the coach. There was a lot of noise when Netflix released Michael Jordan’s documentary The Last Dance, and many founders shared how much they related to Jordan’s approach, but too few recognised the power of Phil Jackson, the coach of the Bulls at the time. 

As a founder grows their leadership team, they must learn to create the environment for a high-performing team, not just role model it. The inability to do this well can be the end of a founder’s ability to lead their company as CEO. 


So, how can you be more Phil?

Start early, start small

The validation and energy we get from building something from nothing is addictive, but we have to make sure we check ourselves out of that process. Founders that see validation from working in the business and not on the business can unintentionally stagnate growth by not enabling their teams to have autonomy. 

As a founder, recognise your own limitations and delegate quickly and early. Sure, at seed stage it’s all hands on deck, but as we move into Series A+, you should have key players around you to shoulder the growth. For starters, double down on where you know you will win and hire around you to build up a dynamic team that plays well together. Hiring executives can be challenging, but developing them is a whole other ballgame. 

Be open with your team that you are intentionally making the shift and what you expect of them and what they should expect from you. This transition is a team effort, so make sure you seek feedback to validate your progress. 

You are there to make sure the work gets done, not to do the work.

As a leader of a high-performing team, you want to be able to understand the skill set each player brings to the court and ensure you’re creating the space for them to thrive. You are there to make sure the work gets done, not to do the work. 

But this doesn’t mean giving them full rein; I have often witnessed founders giving away too much power to over-eager experienced execs who haven’t fully got to grips with your product, culture and clients. Founders then have to sort out the damage later on.

Where to start? 

  • Start by listing out everything on your plate including both things to do (now) and things you’d like to do (later)
  • Go through each one and highlight the ones that only you — as a founder — can do and can’t be outsourced to a team member (ie. raising money, board relationships, press)
  • For everything left, highlight who on your team could support you in either taking ownership of it with your guidance, or take responsibility for part of it

Imagine the goal is to eradicate you from the operations of the business. This is the growth mindset that enables you to let go of things early, hire smart and coach your team to their full collective potential. 

Imagine the goal is to eradicate you from the operations of the business.

Leadership is about setting clear expectations and company culture, calling out bad behaviours like; how they treat their team, when they underdeliver on expectations, or even how they talk to you, early and often so that your leadership team should be clear on what it means to lead at your company. Be firm on what kind of company culture you are committed to building and have a set of values (behaviours that drive your strategy) at hand as a reference point. 

The space to lead

Staying on top of our self-awareness takes time so I often recommend founders block out a weekly hour, at minimum, to check-in on their leadership approach to developing their teams. 

Ask yourself: 

  • What signals are my team telling me that I’m doing things right? 
  • Have I received any direct/indirect feedback that I’ve rejected; what could I learn from that situation?
  • What would I have done differently last week? 
  • What growth opportunities do I see for my team members in the coming quarter/year that would align with their potential and capabilities? 
  • What leader do I want to be and which behaviours do I need to role model? 
  • What does each team member need from me right now?

Unfortunately, there’s no silver bullet or purchasable playbook to leadership. Consistent leadership is about adapting our approach to each of our players in any given situation. And to do that well, you have to understand everybody’s individual motivations and triggers. Get to know your team by asking about their communication preferences, observe how they respond to challenges and know why they are working for you over anywhere else. 

Good leadership also means staying out of the details so you have the headspace to look ahead.

At this stage, good leadership also means staying out of the details so you have the headspace to look ahead. 


Too often, I have had leaders share their discomfort when they have “nothing to do” i.e. their teams are getting shit done. That’s exactly how things should be, because that’s when real strategy happens: the space to create connections, set priorities, look for partnerships and stretch their teams by supporting ‘not doing’. 

Build a team, not several silos

Let’s be clear, a high-performing team is not a group of high performers. You can’t throw smart people into a team and expect them to operate effectively. 

Your role as a leader is to help build cohesive team dynamics by enabling them to work better together. This means helping them to solve their own problems together, instead of being the go-between. Keep energy and confidence up by celebrating small victories and recognising good behaviours.

Avoid creating silos.

Your team is collectively responsible for the business performance so avoid creating silos in your goal setting. The leadership team should be working together as one, and your role as a founder is to ensure they are actively supporting each other, not working against each other: 

  • Set leadership team OKRs that are a company focus instead of departmental — i.e. every leader is responsible for diversity and inclusion OKRs, not just HR. This helps breed the priorities of your business in each employee. 
  • If team members come to you with challenges they are having with other departments, don’t listen; instead coach them to give that feedback to their peers directly and not through you. If necessary, join as a mediator. 
  • Recognise small wins weekly and call that out in front of your leadership team to instil confidence and commitment.

Google has done tonnes of research on psychological safety and its studies prove how teams that work better together drive up revenue. As a team, you should feel comfortable arguing and feel safe admitting mistakes. The easiest and cheapest way to start is to role model. Acknowledge to your leadership team when you’ve mucked up and what you’ve learned in the process. Encourage them to do the same by asking in your team meetings, ‘Who’s got a fuck-up to share and what can we learn from it.’ 

Take the discomfort out of failure by bringing it to the open because if we can’t talk about it we can't address it. 

I’ve worked with countless teams who — direct quote — “like each other too much to disagree,” driving dissent outside of the room where it matters most. I’ve also worked with teams who love to argue but can never make any progress in committing to a course of action. 

An aligned team signals confidence in your employees, an underrated metric in times of uncertainty, therefore communicating as ‘one team’ is key, especially in remote settings when we can’t catch misunderstandings quickly. Take the time necessary to get your team aligned and working off the same page; this can look like creating a collaborative document with FAQs about strategy, processes and responsibilities to tease out any misunderstandings. 


Leading a strong team is a key business imperative; Apple’s CEO Tim Cook said his team’s strength, as a team, in part led to stronger than expected business performance in 2020. 

As a founder growing your leadership team, your focus should be to bring teams together through providing clarity, alignment and focus, whilst maintaining pace and resilience. This is a skill that many founders have to learn as they evolve in their journey. What makes a great individual performer doesn’t necessarily translate to being a great team coach.  

Jordan’s story is no doubt inspiring, but for founders that recognise they need to start playing coach, I’d recommend digging into Jackson’s book, In Sacred Hoops: Spiritual Lessons of a Hardwood Warrior. Or, for the short of time, remember this quote from The Jungle Book that it opens with: “The pack is the wolf, and the strength of the wolf is the pack.”