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How I Book Meetings on LinkedIn

Steal my secret 5 step system

Chris Ritson

26 Apr 2024

3 mins

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I used to pride myself on my ability to Cold Call.

But buying behaviour changes and we have to adapt.

Does that mean, Cold Calling isn’t important? Absolutely not.

But as sellers we need to be constantly looking for new ways to engage buyers and win their trust.

LinkedIn is one of those channels I rarely see SDRs do very well on.

They connect and pitch.

Then we wait for a response. And guess what?

It doesn’t come so we send some BS ‘‘follow-up’’ message like ‘‘did you see my message above’’.

Buyers HATE receiving them. Sellers HATE sending them. It’s lose:lose. We have to stop this.

In this newsletter, I’m going to share with you my personal 5-step system for dominating in the DMs [with examples]:

Let’s dive in.

#1 - Profile

This part is simple.

Scan their profile for 1x observation you can use in the next 4 steps.

1x ''good observation'' is enough for you to create a lot of messages.

I recommend you repeat the same observation again and again. Why? Won't they get bored of it? No. Humans like repetition. A good observation doesn't stop being good because you've said it once.

Here’s what I’ll look at:

  • Headline

  • Location

  • Current role

  • Tenure in role

  • Achievements

  • About me section

  • Mutual connections

This gives me a good picture of what they are doing and the problems they are likely facing.

From here I will pick ONE observation to include in my first message. For example; they grew their current team from 3-30 reps.

PS. Noticing they are a VP Sales or CHRO is NOT a good example of an observation.

#2 - Get Permission

Now I have 1x Observation I am confident I can use in all my future messages I don’t dive in and pitch.

Instead, I use this template every single time:


Hey X - [My 1x observation]. [Compliment them]. [Ask permission based closed question].


'Hey John - saw you grew the ABC team from 3-30 sales reps. Looks like you’ve built a team that’s going to go on and crush it. I can help you get there faster. Mind if I ask a couple of questions?

Typically, I use this template for prospects who are COLD. My definition for this is they have never engaged at all in my LinkedIn content, viewed my profile etc.

#3 - Personalise the Problem

If I have a prospect who engaged with my content or page I skip straight from Step 1 to Step 3 and use this template:

[it’s similar to Step 2 but with a slight tweak]:


Hey X - [Mention what they did]. [My 1x observation]. [Compliment them]. [Ask open ended question about the problem I solve].


'Hey John - Thanks for liking my content. Saw you grew the ABC team from 3-30 sales reps. Looks like you’ve built a team that’s going to go on and crush it. How’s Outbound going for you?

#4 - Position

Now I have them replying to me.

Rather than pitching them as soon as they’ve responded I do figure out if I can actually help them.

Typically, I’ll aim to ask TWO high value questions before I ‘‘pitch’’…

For example:

Template: ’’Most [insert persona] need [insert problem] to work well to get[insert result they want]. [Insert closed question]

Example: ’’Most VP Sales need Outbound meetings to be consistently booked to get good coverage for pipeline but this so rarely happens. Is this similar for you?

[Pro Tip - I use ‘‘typical statements’’ A LOT…]

Once they reply to this feeling similar I will aim to get really specific with my next question:


‘‘Most VPs I work with also mention [insert common specific issue] is a challenge. Are you in this boat also or is it something else that’s stopping the team from achieving [desired result].


‘‘Most VPs I work with also mention Cold Calling is a challenge. Are you in this boat also or is it something else that’s stopping the team from achieving quota?

#5 - Proof and Pitch

Lets be honest - you need to pitch to get a result on LinkedIn.

The key is timing.

By now, I should have a couple of responses from my prospect and a clearer idea of their situation and problem.

Now, you’ve earned the right to sell.

Here’s how I do it:


The [insert persona] at [insert company] fixed ]insert problem] by [insert how they work with you]. [insert the result]. [Insert how they got to that result]. [CTA]

The VP Sales at XYZ fixed their Outbound pipeline problem by hiring me as a trainer. Their team achieved 130% of Outbound pipeline quota last quarter. They used a combination of internal enablement systems and my training programme. Open to taking this convo to a call?

Note - I MAKE the prospect / my customer the hero. Language like:

‘‘They fixed the problem by doing X’’ makes your prospect think …’’wow, if I just do that I can be the hero here and look amazing…’’

This is the state of mind you want to get your prospects in reading your messages.

#6 - Bonus: How to Chase…

This is where sales reps KILL all their momentum.

Imagine you’ve had a couple of responses from prospects and then they go cold and ‘ghost’ you.

It’s usually not personal. It's mostly timing is off, they aren’t interested at all or maybe they were on holiday and it’s a yes they just forgot to respond.

Whatever the case...

You’re job when this happens is to figure out which one is it?

Most reps use language in their follow-ups like;

  • ‘‘Are you still interested’’?

  • Just following up here…

Instead, this is how I do it:

  • It seems like my timing is off..?

  • It seems like you’re the wrong person..?

  • Looks like I’m off with my messaging here..?

  • It feels like you’re happy with what you have?

Yep, that’s right. I’ll label it. I do this by assuming something isn’t right. It’s not perfect timing for them or maybe they aren’t the perfect person.

By labelling I queue the prospect to correct me and we get the conversation either back on track or I disqualify them.

From there I can move on rather than chasing for weeks on end.


LinkedIn success is like anything else.

It’s about creating a system you can rinse and repeat.

Hope this newsletter helps you book more meetings, folks.

See you next week 🙂 

Customer of the Week:

Arti Brannon [the legend] got my Cold Call course and booked meetings straight away…

If you’d like to learn how to Double Your Meetings Booked in just 2 Hours for £97 [33% OFF until end of April], click here: Cold Call Course 

Hope you find this weeks newsletter helpful. Please feel free to share this with colleagues if you think it can help them.

Or reply with any questions you have to this email 🙂 

Cheers, Chris

Whenever you’re ready, here are 4 more ways I can help you in 2024:

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© 2024 Chris Ritson. All right reserved.

© 2024 Chris Ritson. All right reserved.