Stop Putting Off Hard Conversations: Courtney Ramsey on Intent

Jul 31, 2025

5 min read

Updated: 5 days ago

Courtney Ramsey's napkin says quit hitting snooze. It is a philosophy she has carried since 2018, born while writing a speech in a speakers academy. She does a lot of public speaking for a living, and she teaches people a process for tough conversations. She describes herself as a slow mover who likes to think things through, sometimes to the point of analysis paralysis. Quit hitting snooze is not about rushing. It is about doing the impactful thing you know you have been avoiding, and choosing courage over comfort. For leaders, the things we snooze on most are often conversations. A conflict with a partner, a problem with a vendor, or a hard talk with ourselves. Courtney's approach has two parts. Ask what the worst that can happen is, either way. Then open the conversation by saying your intent out loud.

https://www.youtube.com/watch?v=b8FDSQLxVQ0

Inspired by Paper Napkin Wisdom Episode 276 with Courtney Ramsey.

Why we keep putting off the things that matter

Courtney likes to choose the perfect time. Often there is no perfect time. When you snooze often enough, you fall into a pattern. I'll do it tomorrow. In her words, "I'll do it one day, and then one day never arrives," and then you have big regrets.

Getting it over with makes life easier, even when it does not go the way you want. At least you know. And you stop spending time, energy and what she calls brain real estate mulling it over in the back of your mind.

I noticed she calls it a philosophy, not a thought. She agreed. It was one of those things you stumble across that changes how you look at life. Three words that put her old pattern into focus.

How to notice when you are hitting snooze

For Courtney, the signal is anxiety. It is the thing that wakes her at 2 or 3 in the morning, when her brain starts spinning the moment she is conscious. It can also be a gut feeling, something weighing on her. Either way, it is a red flag that she is snoozing on something and needs to make a decision.

Other people feel it differently. Stress shows up in different ways for different people, and it helps to know your own sign.

I asked whether she is gentle with herself when the pattern returns. Her answer was that she is working on it. She calls herself a recovering perfectionist, with higher expectations of herself than anyone else would have. She is working toward more patience and compassion, for herself and for other people. Her view is that we are all doing the best we can with what we've got.

Ask what the worst that can happen is, either way

The first step in Courtney's process is a perspective shift. What is the worst that can happen if I don't do this? And what is the worst that can happen if I do? Can I live with that?

Most of the time the answer is yes. She would rather know and have some resolution than spend years spinning like a truck stuck in the mud.

I like that she asks it both ways. Most people only ask what happens if things go wrong after they act, and that stops them. Looking at both sides makes the cost of waiting visible.

She used the same test on her biggest career decision. In 2017 she left a corporate position with JCPenney, a job she really loved, to start her own business. It meant going back to paying herself her starting salary out of college. It was scary. She asked whether she would regret not trying when she was 65, 75, 85. The answer was a resounding yes. And the worst case? She could drive Uber or wait tables again. That was decent money.

I heard the same thing from John Sleeman, who built one of the largest brewing companies in Canada from scratch. His question was what the worst could be, and his answer was that he could go work at McDonald's for a while. Knowing you will be okay is liberating.

How to use an intent statement to open a difficult conversation

The second step is intent. What do I want for myself? For the other person? And in the long term? Then say it out loud before the hard part begins.

Courtney's reasoning is that conversations about conflict often get worse, because the other person assumes negative intent. Saying your intent levels the conversation. It keeps you on track, and it tells the other person you are coming from a good place.

Her example is a business partner who said something that hurt. She might open with this. "I really care about you as my friend and as my business partner, and I know that you and I care about each other, and we want to have a strong relationship. There's something that came up the other day that I'm having a hard time letting go, but I know if we talk about it together we can get through it. Would you be willing to talk about that with me?"

I noticed what she left out. She did not project an assumption onto the other person. She stayed in her own intention, then named what was bothering her. That is vulnerable, and Courtney thinks the vulnerability is what keeps the other person's defense wall down. Once defenses go up, it is very hard to get them back down. Saying you are uncomfortable or nervous humanizes you and helps people stay psychologically safe enough to talk.

Does an intent statement work with people you barely know?

I asked her about vendors, flyers and infrequent customers. Courtney thinks the intent statement matters even more there. People who don't know you have very few data points about who you are. They fill the gaps with assumptions. So with a vendor you have dealt with twice, saying out loud that you care and want to resolve this does a lot of work.

It still matters with the people closest to you. Even a spouse of 20 years needs to know you are coming from a good place.

And for the leader who doesn't want to look weak? Courtney gets it. We are conditioned not to show weakness, and social media only shows the highlights. But admitting vulnerability, even briefly, shows you are not coming in to put the other person in their place. It shows two people who want the relationship to be better. Notice what she did first when I pushed back. She acknowledged the concern. Acknowledging how someone else might feel is an easy way to find common ground.

How to apply this in your business this week

Pick one thing you have been snoozing on and work through it.

Notice your signal. What wakes you up at night or sits in your gut? Write it down.
Ask what the worst that can happen is if you act, and if you don't. Can you live with each?
For a bigger decision, ask whether you will regret not trying, years from now.
Before a hard conversation, write your intent statement. What do you want for yourself, for them, and for the long term?
Open with it. Say that you care, name what you are struggling to let go of, and ask if they are willing to talk.
Use the same steps for the conversation you need to have with yourself. Make quiet space for it first, and speak to yourself the way a best friend would, reminding yourself of the hard things you have already gotten through.