Hi Reader,

At a recent Fractional Water Cooler 🚰, one of the questions was this: I had a good call with a prospect. I followed up. She said it wasn't relevant right now, maybe in the future. Should I reach out again, and when, without becoming the person who keeps nudging?

It wasn't the only question that day about a message like that.

What I'm noticing

Our guest was Sara Royf, who coaches consultants on LinkedIn. She spent the session on how to get from a conversation to a booked call, and the questions people asked kept circling the same worry.

One person wanted to reach out to former colleagues he hadn't talked to in years, "without looking like you're coming with your hands out."

Another had the harder version: he was the one who'd said "I'm slammed, not right now," and now going back felt weird.

And one from the chat: how do you know when to let it go?

All three assume the other person is exactly where we left them, still remembering the awkward part, still saying no.

Sara's line for this: time has passed, not paused. Their situation has changed since you last talked, and so has yours. So treat it as a new conversation.

Your next move

Three things to try this week:

1. Make your list from the inside out. Old leads that didn't go anywhere, past clients, people you used to work with. Sara said most of the consultants she coaches never need to message a stranger. Still in a job? Start with former colleagues. You don't need leads for this. Your AI can help you build the list: who you talked to this past year and haven't heard from since.
2. Ground the first line in something real. One way Sara suggested getting past the "hands out" worry: "I was recently talking to [name] and it made me think of you." It gives the message a reason that isn't you. If you keep call notes, your AI can pull up the last thing you two talked about.
3. Ask about now, not then. Instead of "do you still need help?", try "When we last talked, you were focused on X. How's that been going?" Sara's rule is no pitch until they've told you about a problem, and at least two curious questions before you get there.

Your homework: five messages, same as Sara assigned that day. Wait about a week before a second nudge, and if it's quiet, try a different channel (a text instead of LinkedIn, an email instead of a DM).

My own commitment that day was to go through my pipeline the same way. I did, and then I automated it: every Sunday my AI flags who I've gone quiet with and drafts a first note to each. I review every one, and some don't go out.

The remembering and the first draft are automated. Who hears from me, and what I say, is still mine.

Life beyond the screen

A couple of weeks ago, at the end of a work trip in Munich, I messaged a friend I hadn't talked to in a while. Turns out we were booked on the same flight home. We caught up on the train to the airport and the whole way to the gate.

If I hadn't sent that message, we might have been on the same plane and never even known.

Same as with clients: the hardest part is the first line, and the other person is rarely keeping score the way we may think.

A question for this week: Who's the one person you'd message today if it didn't feel awkward?

Want help working through your own list? Outreach is a big part of the Fractional Kickstart: we work together over two to three months to turn what you know into a consulting offer and land your first clients, including who to reach out to and what to say. If that sounds useful, hit reply and we'll find a time to talk. (More about it here: https://www.chillaborate.com/fractional-kickstart)

Come to the next Water Cooler 🚰 Thursday, November 19 (9am PT), Alina Schenk joins us on why "we're too small for a CRM" is a myth: how a simple system keeps leads from going cold, even for a team of one. Save your spot: https://luma.com/y3x2rncb​

Let's Chillaborate,

Dina

Founder, Chill Labs

PS: Know someone with a message they keep meaning to send? Forward this to them. 💙