From pitch slap to proper conversation

Date: 24/02/2026
12:00pm GMT (1 hour)

Do cold LinkedIn DMs give you the ick?

You know the ones.

Hi Kim, I loved your profile…

Followed by a pitch that clearly wasn’t written for you, your business, or anyone with a pulse.

You can spot an automated LinkedIn DM from a mile off. And chances are, you delete them just as fast. Or you wake up choosing violence and send a reply…one I sent the other day was ‘I love a good pitch slap, which automation tool did you use?’

So why do so many people still use them, and more importantly, how do you do outreach on LinkedIn without becoming one of those people?

Just because DMs give you the ick, doesn’t mean they aren’t useful – especially for self-employed folk.

So we’re taking the ick out of cold DMs.

This is not about spamming strangers, copying scripts, or pretending to build “relationships” when you’re really just pitching. It’s about understanding what makes a message feel human, relevant and worth replying to, and how to start conversations that can genuinely lead to work.

What we’ll cover:

We’ll break down what actually puts people off LinkedIn DMs, and what makes them stop, read, and reply instead.

We’ll be diving into:

  • Why most cold DMs fail before the second line
  • How to instantly spot an automated or lazy message, and how to avoid sounding like one
  • The 10 top tips for LinkedIn DMs
  • How to personalise without spending hours stalking profiles
  • What to say in a first message, and what absolutely not to
  • How to warm people up before you ever hit send
  • When to move from chat to call, without it feeling awkward
  • How to follow up without giving off desperate or salesy vibes

Who this is for:

This session is ideal for freelancers, consultants and small business owners who want more conversations with the right people, but hate the idea of being pushy, spammy, or salesy on LinkedIn.

About the session host

Kim Ellis is the founder of L&D Free Spirits and Go Ginger Learning Solutions. She helps freelancers build visibility and confidence without losing their personality or their soul. Known for calling out nonsense and simplifying what actually works, Kim focuses on practical approaches you can use straight away.

This session is free to attend live, the recording will be available to Free Spirit members.