Important Conversations

Do you face difficult conversations head-on?


Michael Daly, President and Board Chairman of The Orange Duffel Bag Initiative, discusses how to deal with difficult people or situations by initiating important conversations. From his experience in working with non-profit organizations, Michael feels that when you're faced with partners or volunteers who may not be on board with the vision, it's critical to back up and provide everyone with an opportunity to understand the founding mission, expectations and "who we are." Michael also offers clear steps for leading positive discussion and addressing issues head-on.

As you can imagine in any new organization there are going to be times where people may have crossed your path, wanted to be involved, and perhaps didn't want to follow the plan or the direction and found themselves in an antagonistic situation. With any good leadership you have to be able to identify the barrier and remove the barrier. That can be anything that's going to stop the momentum and the direction of a plan.

So when it comes to difficult people, or it comes to those you have to part ways with, the way that I've always approached it is to help them understand that this choice that's about to be made is really their choice. That what they're struggling with, what they're angry with, what they're frustrated with is because it's something about them, not the fact that something has happened to them. So good leadership is helping the person understand that this is not a right fit for them, not that you're not a right fit for me.

How I help them see that is I take them to the point of where they started. I walk them through the journey of what they knew and what was communicated and what they feel was not communicated. And it becomes very clear as you have the dialogue that the decision of change or resistance or concern was really self motivated. I've learned through our coaches and our coaching that all decisions are really made from a place of either fear or trust. If you find yourself wondering why you feel or you're concerned about a particular situation or person, you stop and ask yourself, "Am I in a position of fear or am I in a position of trust?" Then you'll see that you're part of that whole role of what's building within yourself.

In the nonprofit world, you're governed by the board. You have partners. You have volunteers. You have passion for the mission and for the work. You are sharing that passion. So for a board member or a volunteer, if things aren't working out, we do have agreements that we set up with each of them so that they understand that here's our expectations and here's who we are, and here's our culture. And they subscribe to that, but this kind of work, you have to want to do this. You have to feel it. You have to have the desire and you have to have the passion. If that starts to wane in any way, even with a board member, then we'll usually call a meeting and we'll have an open discussion. So good leaders address those things head on and do it in a very careful and thoughtful way, but they address them. Through that discussion either we'll reignite that desire or they'll understand that this really isn't for them at this point in time. So we're very careful and thoughtful about how we approach that. But if you don't have the desire, you don't have the passion, then it will not benefit our students, and it will not benefit the work. So it's better not to be involved than to be involved. So those who don't really approach it or handle it very directly become stagnant, and their culture becomes very fragmented.


Michael Daly

Michael Daly, President and Inaugural Board Chairman of The Orange Duffel Bag Initiative, has had more than two decades of successful professional experience with renowned organizations such as AARP, Smithsonian Journeys, The History ...

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