By Kath Rosen, CEO, The Orchard Project
We know that the relationship we have with our chairs is one of the most important ones to land. When it works well, it steadies us through difficult decisions and gives us the confidence to lead. When it doesn’t, it erodes our authority, drains our energy, and ultimately harms the organisation. It is also a relationship that is far harder to leave than you might expect once you realise it is not working.
I have been the CEO of The Orchard Project for 15 years, and I have worked with five chairs in many different forms, including founder chairs, co-chairs and chairs from very different sectors. Some were deeply supportive and helped me do my best work. Others were, frankly, disastrous. One experience so corrosive that I seriously considered leaving the organisation to protect my mental health. That experience changed how seriously I take chair recruitment and how cautious I am about decisions made under pressure. I no longer believe in committing just because someone says yes. Enthusiasm or familiarity are not a basis for long term commitment.
Being a charity CEO is a stressful and isolated job with limited peer support. The relationship between the CEO and the chair is the heart of how well a board functions and how psychologically safe a CEO feels. As the external environment gets tougher each year for charities, the last thing we need is someone inside our organisations making it harder for us too.
A weak chair slows decision making, amplifies conflict and leaves the CEO carrying far too much emotional and organisational weight. A strong chair does the opposite by helping us think clearly, backing us publicly, challenging appropriately and strengthening the organisation as a whole.
Over time I have come to believe that a chair’s background, sector or formal credentials matter less than we think. What looks impressive on paper does not always translate into being effective in the role. Faced with pressure and fatigue, it can be tempting to choose someone already around the organisation simply because it feels easier. Much like dating, convenience is not the same as compatibility.
It is easy to be dazzled by a strong CV or senior title in the same way you might be charmed by a great first date. Red flags are easier to ignore when you are relieved that someone capable has said yes. Scarcity plays a powerful role – you tell yourself it will probably be fine and stay longer than you should because extricating feels disruptive, uncomfortable or costly.
What we actually need in a chair is that rare mix of chemistry, strength, commitment and emotional intelligence. We need someone confident without being domineering, challenging without being undermining, and committed enough to put serious time and care into the role.
What frames my thinking is less about technical competence and more about trust, power and grit. The kinds of questions I am quietly asking myself in the background alongside the standard trustee interview ones are:
- What genuinely motivates them to do this role.
- What work have they done on themself and their leadership style.
- Why did their last leadership role end and what part did they play in that.
- How do they understand their own power and privilege.
- And for male chairs in particular, how are they actively reflecting on their role in the patriarchy and how that shows up in leadership.
These questions matter because power dynamics always surface in chair and CEO relationships whether we acknowledge them or not. Avoiding them does not make them disappear and they simply show up later in more damaging ways.
Over the years we have tried multiple ways of recruiting chairs and senior trustees for The Orchard Project.
Recruiting from within the board often looks sensible and low cost. In my experience it rarely works and can leave lasting damage when it fails.
Word of mouth is quick and reassuring but tends to reproduce the same profiles, reduce diversity of thinking and create echo chambers.
Running an open process ourselves brings interest but places a significant emotional and administrative burden on the CEO.
More recently, we have used a recruitment consultant. This cost around five thousand pounds for our most recent chair. It felt expensive but I believe it was an essential investment because chair recruitment should not be driven by scarcity. Getting it wrong or making do is far more expensive in the long run. I have lost huge amounts of charity time dealing with the fallout from a toxic chair. I have seen other trustees leave, my own energy drained by emotional labour, and actual money out the door spent on mediation.
(And a jaded note on mediation – in my experience, this only works when power is genuinely shared. The situations that force you into mediation are often those where that willingness to share power is not present thus rendering it draining and useless.)
A good recruitment partner can bring huge reach, structure and choice. They help produce candidates with the skills, networks and lived experience we actually need. And crucially, they provide an external sounding board for the CEO and impartiality to reassure the rest of the board. That kind of support is rare and I have found it really helpful. This comes alongside a deep distrust of feeling that “external” consultants are the solution to internal charity issues.
Happily I can say that the chair I have now brings out the best in me. She has complementary skills and networks, treats me with respect, listens, challenges me appropriately and puts serious time into the role. It has been a long road to get here, but the difference it makes has been transformative.
Much like dating, chair recruitment suffers when driven by fear of being alone or fear of not finding anyone better. That mindset leads to compromise in all the wrong places.
Before your next chair appointment , intentionally pause. Be honest about what you need, ask better questions, budget properly and don’t be shy to get help. And remember that while being a CEO can be lonely, being undermined from inside your own organisation is far far worse.
We deserve a chair relationship that builds and resources us rather than drains our energy, much like with a dating partner!