Creating Support Systems for Your Leadership Team

Leadership teams in charities face a curious paradox. While most are brilliant at creating supportive environments for their beneficiaries and frontline staff, they often struggle to provide that same support for each other. 

This pattern appears across the sector – a disconnection that exists not because of individual personalities, but because of the structure of organisations, often creating isolation exactly where connection is most needed.  

It's a challenge that rarely gets discussed openly but can affect charities in profound ways. The question isn't whether charity leaders care about supporting each other – of course they do. It's about whether the structures and cultures we've created actually enable that support to happen. 

When Leadership Teams Function as Islands 

Think about how most charities are organised. We have directors of services, finance, fundraising, HR – each with their own targets, budgets, and teams. On paper, they form a leadership team. In reality, they're often a group of people who happen to attend the same meetings. 

The barriers between them develop naturally: 

The packed diary: when calendars are filled with back to back meetings, those casual conversations where relationships actually develop simply disappear. ‘Let's grab coffee’ becomes something you say but never actually do. 

The unspoken rules: there's often an implicit understanding that you should arrive at leadership meetings with everything sorted and under control. Admitting that there are challenges can feel like confessing failure. 

The clashing priorities: whilst you’re all working toward the same strategic plan, it can feel like priorities clash. Operations are busy delivering the services, whilst Comms wants case studies urgently, whilst Finance wants to reforecast the budget, and the Data team need to get the reporting done for the funders. 

The pressure to succeed: and because the outcomes for the charity are so important, admitting mistakes, or not having the answers can feel vulnerable and risky, when everyone on the team seems to have it together. 

Throughout my career, leadership team meetings sometimes felt like the loneliest meetings in my calendar – sitting together for hours, giving updates, solving immediate problems, but leaving knowing very little about how anyone was really doing. 

Why This Matters (Beyond Just Feeling Better) 

When the work can be difficult, when you’re all facing huge pressures, and the system around the charity so challenging, it’s clear that supportive working environments are important for the wellbeing of the leadership team. But here's the thing – this isn't just about wellbeing (though that certainly matters). It's about effectiveness. 

When your leadership team operates as separate islands, your charity suffers in very practical ways: 

You miss crucial connections. Most significant problems in charities don't sit neatly within one department. They live in the spaces between fundraising and finance, or services and HR. When directors don't truly collaborate, these cross-boundary issues fall through the cracks. 

You duplicate efforts. I've seen charities where different directors have separately tasked their teams to solve the same problem, unaware of each other's work. That's double or triple the resource for a single issue – something no charity can afford. 

You lose collective intelligence. A genuine leadership team is smarter together than individuals working separately. Without trust and connection, you never access that collective wisdom. 

Your resilience weakens. When a crisis hits, isolated leaders break rather than bend. There's no support system to distribute the load. When we're all frantically baling water from our own boats rather than figuring out together how to patch the holes, the whole organisation suffers. 

What Gets in the Way of Real Support 

Most charity leaders aren't cold or uncaring people – quite the opposite. So why do leadership teams struggle so much with supporting each other? 

Part of it is simply how we structure things: 

Meeting agendas that are packed with operational updates leave no space for connection. When your standard agenda is fifteen items in sixty minutes, deeper conversations never happen. 

The focus is on the problems because there is so much to fix and to get right. But by missing the successes, and noticing each other's achievements, we get caught in a cycle of negativity. 

Away days often focus on strategy or team-building exercises, but rarely create space for honest conversation about real challenges. And without actually facilitating honest conversation, the team-building activities are ineffective. 

The language gap – many leadership teams lack shared vocabulary for offering or asking for different kinds of support. "Can we talk?" might mean anything from "I need advice" to "I need to vent" to "I need you to take on some of my work." 

And then there are the more subtle barriers: 

The charity mindset that celebrates overwork and self-sacrifice makes asking for help feel almost selfish. 

Fear of mistakes – in a sector where demonstrating impact is everything, making mistakes can feel risky, instead of an opportunity to learn, grow and improve. 

Creating a Team That Actually Functions Like One 

The good news is that transforming how your leadership team supports each other doesn't require massive organisational restructuring or expensive away days. Often, it starts with small but intentional changes in how you work together: 

Make space for real check-ins. Begin meetings with a genuine check in on how everyone is, and what there is to celebrate. 

Make mistakes ok and asking for help the norm. This is going to require you as a leader getting vulnerable first and leading by example. 

Distinguish between different kinds of support. Sometimes you need practical help, sometimes you need advice, sometimes you just need someone to listen. Being clear about what you're asking for makes supporting each other simpler. 

Create reflection partnerships. Pairing each senior leader with a partner who they know less well can create safe spaces for processing challenges and finding new perspectives. 

Establish confidentiality boundaries. Be explicit about what stays in the room and what can be shared. Trust develops when people know the rules. 

Model from the top. CEOs who demonstrate appropriate vulnerability create permission for others to do the same. This doesn't mean sharing everything, but it does mean being honest about challenges, and when you don’t have the answers. 

Create informal spaces. Sometimes the most important conversations happen over coffee, not in formal meetings. Make time for these connections. 

Get outside perspective. Consider bringing in external facilitation for initial conversations about how your team wants to work together. 

The journey from silos to a genuine leadership team doesn't happen overnight. But each step toward more honest, supportive relationships strengthens not just individual wellbeing but your charity's effectiveness. 

After all, the people you serve don't benefit from directors working themselves to breaking point in separate silos. They benefit from a cohesive leadership team that combines their strengths to navigate challenges together. 

Want to find out how I can help you bring your team together, get in touch.