Surviving a Boss Chair: Practical Strategies for Executive Directors
Nov 27, 2025
Q:
“Thanks for your recent article, “Governance as Gatekeeping: What To Do When Your Chair Takes Over The Board’. The ‘Boss Chair’ phenomenon is such a huge issue, and it really impacts management as well as other Board Directors. You gave some great advice for Board Directors who are dealing with a ‘Boss Chair’, but didn’t mention how to navigate this dynamic as an ED. I’m trying to figure out how to draw this to the attention of a Board Chair who doesn’t think that being ‘Boss Chair’ is a problem, backed up by a Board that doesn’t know any different. Any thoughts?”
A:
While I think that some EDs love a Boss Chair - because they can drive results - most find it to be a challenging and often exhausting dynamic to manage. And if your Boss Chair is the power-tripping type, that can very quickly turn into an unhealthy power dynamic for an ED. So how do you call attention to this dynamic if you’re an ED dealing with a Boss Chair? I think the way to manage this is the same as you would approach any general concerns that an ED might have with a Board Chair’s conduct.
Start With a Direct Conversation
If you can, start by having a conversation with your Chair. So many complex governance problems could be avoided if more people were willing to have uncomfortable conversations! Saying this, I recognize that it may not be feasible in all situations; in the ED-Board Chair relationship, the Chair holds a significant amount of power. Not all Chairs are open to having the kind of conversation where the ED can provide feedback or direction; some Chairs would be outright hostile in a situation like this, and others would go so far as to lash out at the ED in reprisal.
But if you think it’s doable, it’s definitely worth addressing the issue directly with your Chair. You’ll want to find a way to depersonalize the conversation - make it about a governance issue, not a personality conflict. If there is a specific behaviour or incident relating that had an impact on the organization (or you directly), it can be helpful to name it, explain why it’s a problem, and suggest a path forward. Keep things respectful and empathetic, without coming across as judgemental, or making assumptions about intent.
I know some EDs will read this and roll their eyes - like I said, not every Chair would be receptive! - but some really would be. In my experience, Boss Chairs are just as likely to be well-intentioned individuals playing a role that they may not actually want, as they are to be ego-driven power-trippers (I think I used the word ‘arse’ in my last article?). I once advised a Board Chair who was exhausted and overwhelmed by managing everything on the Board, and their approach was causing a lot of tension with the ED. When I told them how important it was for them to give back some power to the board, they were so relieved! And I have had multiple Board Chairs break down in tears during calls when they describe the weight of responsibility on their shoulders. You might be surprised by your Boss Chair; they may be more willing to make the shift than you think.
However you approach this conversation, in addition to considering your Chair’s personality and communication style, it’s also helpful to think about their personal goals and motivations. Is your Chair driven by a desire to strengthen the organization? Focusing on the need for clearer infrastructure, like role descriptions, or a more sustainable Chair role, may make sense here. Is your Chair motivated by a desire to develop their own leadership skills? Framing the conversation as an opportunity for personal development might land well. Maybe your Chair is desperate to improve board engagement? Talking about how to shift responsibility onto other Directors may resonate.
But what if your Chair is ego-driven? What if their goal as Boss Chair is just to feel powerful?
In this situation, you could try to use the conversation as an opportunity to set or reinforce boundaries. But I think it’s important to recognize here that a conversation may not be helpful - and could actually be harmful; in which case, skip the conversation and move on to the next step.
Shift the Culture, Not the Chair
When direct feedback to your Chair won’t land - or isn’t feasible - you can try some indirect approaches to try to shift your overall governance environment instead. One of the challenges of the Boss Chair scenario in particular is that it is often disempowering for other Board Directors, who may consider the dynamic ‘normal’, or feel a lack of agency in addressing it. In my experience, I’ve found that it’s really rare for Board Directors to challenge a Boss Chair. So your goal with indirect strategies is to help shift the Board’s understanding of Director and Officer roles, and, hopefully, to empower them to take responsibility for the Board’s culture and norms. Here are a few suggestions that may help:
- Plan some governance training: Provide some learning and development for the full Board, related specifically to Board Director and Officer roles and responsibilities. If you don’t have the budget for training, set aside some time at a meeting to review and discuss the bylaws and any role descriptions, emphasizing that the Board works as a whole, and all Directors share equal power and equal accountability.
- Conduct a governance assessment: A comprehensive governance assessment can help surface constraints, like a Boss Chair dynamic, in a constructive and non-confrontational way. You can bring in a neutral third party to support this work, or use a published governance framework and DIY.
- Provide feedback through existing channels: If possible, share feedback to the full Board through the Board’s self-evaluation, or the ED performance evaluation process. Granted, these channels don’t exist in every organization (and too many Boards don’t actively solicit feedback from the ED through these processes). If that’s you, start by building up these practices.
Sometimes You Have to Wait it Out
It really sucks to be an ED navigating a challenging relationship with a Chair. Sometimes, no matter how much effort you put in, the Chair cannot or will not shift, and the Board will just avoid addressing the issue. If you have to live with your Chair for the short term, do whatever you can to make that manageable for yourself, and focus on building out better infrastructure so that you can break the Boss dynamic when their term ends. But remember, if a Chair’s conduct becomes a risk to the Board, is affecting your work, or crossing the line into harmful behaviour, you may need to escalate your concerns to another Board Director, or get legal advice for yourself.
Big Takeaways:
- Start with a direct conversation if you can. Some Board Chairs are overwhelmed and well-intentioned; others are ego-driven and unsafe to confront. But if this approach is feasible for your situation, it’s the right place to start.
- Use governance-level strategies to shift culture. Board training, governance assessments, and formal feedback channels can empower the board to reclaim its collective authority.
- Protect yourself and plan for long-term change. If all else fails, you can try to wait out the current Chair. In the meantime, keep working on building better governance infrastructure.
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