Whether you are the Chair of an association board of directors, or the chief staff officer (Executive Director), facilitating tough conversations at the board level isn’t always easy. The best way to handle tough conversations is through open and transparent dialogue and, whenever possible, by arranging face to face meetings.

The chair of the board and the Executive Director or CEO should actively invite all directors to participate in the conversation. The worst thing that can happen with a challenging situation is for someone to feel like they weren’t heard before making a decision.

Often, discussion of issues or concerns will start over email before moving into formal discussions during a board meeting. The challenges with email correspondence can include:

  • Confidentiality
  • Balance of voices
  • Tone perception
  • Legal concerns


Board member should keep in mind that even when outside of a board meeting, discussions via email should remain confidential. Since email messages are easy to share verbatim with those outside of the board, keep confidential conversations to a minimum.

Balance of Voices

A board is a diverse group of individuals with varying areas of expertise and varying personality traits. A diverse board can consider more perspectives on more scenarios. This means that some directors will likely be more eager to speak up, while others might prefer to take a step back in potential conflict situations. When  some directors fall into the group of people who are keen to reply instantly to every email message, others may not want to weigh in at all via email. Finding the right balance and inviting people to appropriately participate in email discussions is important.

Tone Perception

When corresponding over email, it is difficult to portray your intended tone. The tone of email messages often comes across different from how it would face to face or over the phone. It is easy to misinterpret the tone of an email or to be unsure of the intention of the writer; too often email messages can be misconstrued. More worrisome is the fact that some people become more combative over email since they are not faced with looking others in the eye. For these reasons, it is best to keep most tough conversations in the board room.

Legal Concerns

Email correspondence, like all other documents, amongst directors and association management could be subject to “discovery” during legal proceedings. Consult legal counsel to understand the risks and ensure conversations stay on track and not defamatory, offensive, or anti-competitive.


Despite these challenges, I believe boards can be required to discuss items or vet ideas by email since there is not always enough time during formal meetings. An association’s leadership should work together to create an environment where everyone feels heard and all directors actively listen and participate in discussions.

We have recently had two association clients dealing with tough questions around perceived or real conflicts of interest. In both cases, concerns have been raised about the actions of some or all board members. Board members being questioned act (in their opinion) in the best interest of the organization and their profession. However, that isn’t always enough. Unfortunately, perceived conflict can sometimes be worse than real conflict. Here are a few articles from myself and a colleague on this topic:




Managing difficult conversations, whether by email or in person, is like many other challenging situations, it is about clear communication. When a tough situation arises the best thing an association leader can do is to encourage open and transparent dialogue in a safe space where everyone can openly share their opinions.