How to Have Difficult Conversations

Apr 25, 2024 | Grant Writing

Image of two women talking over a cup coffee

I don’t know how you handle conflict, be it personal or professional, but my go-to modus operandi is avoidance. I’ve always been a peacemaker, and when things get uncomfortable for myself or anyone else, I will happily change the subject, crack a joke, or simply sweep things under the rug so no one’s feathers are ruffled.

For the longest time I thought I was doing everyone in the room a big favor. Turns out, I was part of the problem. Because when you don’t talk about the problem, it doesn’t go away. Sure, it may seem like you’ve moved passed it, but chances are, it’s still festering. And most likely it will reappear at the most inopportune moment.

Whether you are a grants division of one, work as a solo consultant, or have tons of colleagues, we all interact with others: board members, bosses, elected officials, clients, fellow consultants, and more. Figuring out how to have those difficult conversations is a skill we all need.

Here are a few tools I’ve learned over the past few years to help with difficult conversations.


When you know it’s going to be a difficult conversation, think about the three main points you want to make. Write them down. Don’t be afraid to refer to your notes to keep yourself on track.

It seems simple but it works.


This conversation may go as smoothly as possible. It could also fall off the rails. I find it helpful to think about the likely end results – ranging from a peaceful resolution to nothing being resolved. For me, it helps to prepare for it all.


Find a trusted friend, give them the basics, and ask them to play the part of the other person. This way you can practice using your notes and finding the right words and/or phrases to use. You can even ask the other person to play nice or dig in their heels.


This is a conversation, which means you need to truly listen to what the other person has to say. It is okay to stand firm in your need to have the conversation, but if new information comes to light, it may alter the points you planned to share. And that’s okay.

New information may not change what you came to say. And that’s okay too.


I didn’t figure any of this out on my own. I had help over the years.

I often talk to trust friends and colleagues, especially those who are good at speaking up and standing their ground. Their advice, shared confidence, and willingness to practice with me makes all the difference.

Last year I worked with Charlisa Garg, a professional coach. Over the course of eight sessions, she worked with me on topics of my choosing. We spent time talking and working on time management, putting my focus where my passions like, and having difficult conversations. She taught me the strategy of writing down my main points and doing a practice run. This one-on-one focus was the perfect way to work on exactly what I needed. I love knowing that I can work with Charli again if needed and either pick up where we left off or cover totally new territory.

This year I completed the Dare to Lead training facilitated by Julie Boll. I cannot tell you how much Julie and this cohort of 8 nonprofit women meant to me. Together we wrestled with our own calls to courage, learned to write our own permission slips, and practiced having those tough conversations. I especially loved that the training gave us starters and tools for opening and wrapping up dialogue with others, particularly for those uncomfortable conversations.

Does this mean I’m an expert in difficult conversations these days? Far from it, but I am more likely to have them. Because whether we like it or not, difficult conversations are necessary at times, like when a boss doesn’t understand why you can’t write a federal grant all by yourself in three days, or when a colleague doesn’t meet the internal deadlines set for a project, or when a board sets unrealistic funding expectations, or when a fellow grant professional makes a snarky comment on a social media post.

Not every conversation will end the way I want them to, but I believe they are worth having. And the more I have them, the more courage I have to face the next one.

What helps you have a difficult conversation? I’d love to hear from you:

Amanda Day
Fundraising HayDay

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