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The Prospecting Playbook: Turning LinkedIn Connections Into Clients

The Prospecting Playbook: Turning LinkedIn Connections Into Clients

Updated 22 April 22



LinkedIn is a powerful platform.

But when it comes to prospecting, most people use it terribly. They spam horrible connection messages, fake interest, and come across as needy weirdos.

Have you ever had someone reply to your LinkedIn message with the following:


“I get sales messages like this all day. You’re all robots anyways, stop messaging me!”’


I'll put my hands up - I used to get this a lot.


Eventually, it forced me to reevaluate my approach. I tested THOUSANDS of connection requests (15k+), follow-up sequences… I even tried sending links, PDFs, and everything in between.

In this document, I’m going to reveal my findings and thoughts on how to best approach LinkedIn from a lead-gen perspective.

It helped me generate 10-25 calls each month last year and was the platform that helped overcome the $5k/mo hurdle in my startup.

I found LinkedIn works best for anyone who can directly approach and engage with their niche. But like any social media platform, you need to nail down the basics to make it work:

Niche → Problem → Offer

And to generate consistent results without making this a full-time gig, you'll need a system you can execute with as little time/effort as possible. 





Building Authority

DM chat

Discovery call

Rockblocks I Experienced And How I Overcame Them

3 Examples of my LinkedIn strategy in action

Gareths 10 commandments 


1. Positioning

Your LinkedIn profile can make or break your results.

Whether you’re cold connecting with a lead, engaging in a DM chat with a prospect, or demonstrating authority with relevant content. Here's what will happen... People will check out your profile. They'll qualify you and look to answer 3 simple questions:

1. What does this person do?
2. How can they help me?
3. Should I trust them?

If they feel you can add value, they may reach out directly (more on this below). But your profile needs to be built in a way that’ll get your market excited about what you do. Here are a few pointers:

  • The ‘Headline’ is key as it's one of the first things prospects see when checking you out. A simple “Helping <niche> solve <problem> using <mechanism>” OR “Helping <niche> achieve <ultimate desire> using <mechanism> will work.

  • Your header image can be used to make you look professional. A snap of you speaking to an audience will also add credibility. If you don't have one, knock something up in Canva with your company branding.

  • ‘About’ section only shows the first couple of lines so make sure it’s snappy enough that people will want to read the rest. Describe the story of your market so they can read about their pain points and the transformation on offer from working with you.

    ‘Featured’ section is ideal for video client testimonials. If you don't have any yet, then a quick 1 minute video introduction of the benefits you have to offer them. In other words, why they should want to connect with you.

    The ‘Experience’ section can be used to explain what you do and the results they can expect. Finish off with a clear CTA such as “Shoot me a DM here on LinkedIn” OR “Book a call using this link”.

Once you’ve got this part sorted, it’s time to move on to…


2. Connecting

The best way to view LinkedIn is as a marketplace you can leverage into a sales funnel. At the top of the funnel, you'll want to build your audience.

These are people from your niche who go from being a stranger → to being aware of you → to then trusting you.

There are a few ways to do this which I used to generate results.

a) Going in cold
Using Sales Navigator, I find my niche using filters then send them a connection request. You can also automate this process by utilising either a VA or an external tool.

If using a tool, take a look at MeetAlfred (use this link and receive a 21-day trial). It's a cloud-based platform and has a way of getting around LinkedIn’s connection request limit.

Keep in mind that when connecting this way, if too many people click the link which states they don't know you, LI will suspend your ability to connect for several hours or days.

And if you’re suspended on multiple occasions, they'll stick you in ‘Linkedin Jail' by permanently restricting your account. You’ll then need to appeal and grovel to their customer service team.

My advice is to start off using this method until you’ve built up an audience. It’s at that point you’ll be able to connect solely with warm leads.

b) Leads who visit your profile
LinkedIn tells us who has visited our profile (and when). I always connect with prospects who have visited my page. When connecting, I do it with a personal note detailing the fact they checked me out.

Many of my clients came like this. They'd check me out, I'd send a connection request and they'd then tell me they needed help.

c) Leads engaging with my content
These are my warmest leads and I've been using the same process as above.

I send them a personalised connection request and make sure they remember that they liked/commented on my post.

d) Leads engaging with other people's posts
My niche follows other people on LinkedIn. I've been using that by finding 5-10 people who share my niche but solve a different problem.

The trick is to find influencers with large audiences (100+ likes per post on average) and add value in the comments. Then connect with people who have responded to your replies.


3. Building Authority

The majority of people in our niche aren't ready to buy today. But that doesn't mean we should only look for the 3% of buyers who are shopping for a solution now.

I've been warming up the rest through content until they give me a signal (usually checking out my profile or engaging with one of my posts).

You'll want to write 1 post per day (multiple posts on the same day cannibalise your first post visibility). Right now, people on LinkedIn engage best with personal stories which tie in what we do.

For example, you could write about the day you quit a well-paid job to start your own venture so you could solve problems for your market.

Images and videos do help with engagement (the algorithm favors posts which have them).

I recommend using personal images (stay away from anything generic or too wild) and videos under 2 minutes (make sure they have subtitles because some like to consume without sound on).

As stated in point 2, you can also do this by engaging on posts from bigger influencers in your space, but who solve a different problem.

After time, you'll start capturing their audience which is also your market.

4. DM Chat

My goal is to start 20 conversations per day, all warm.


In other words, they’re either people who’ve checked out my profile, engaged with my latest post, or replied to one of my comments on a post from someone who shares the same audience.

If I don't have enough, I'll use Sales Navigator to cold connect, making sure to personalise each outreach message.

For example, if I were looking for startup founders, I could congratulate them on launching their business.


My goal is to qualify those and see who's a good fit for my offer. I segregate those people into 3 categories here:

1) Not in my target prospect → Drop them politely or point them in the direction of someone else who can help

2) Target prospect, not ready → Enter them in my CRM (Pipedrive but you can use Hubspot) and set a reminder to follow up

3) Target prospect, ready -> Enter in CRM + book a discovery call

20 → 3 → 1


My daily goal is to make 3 offers to go to a discovery call and have one person agree. This gets me 20 DC which 80% turn into a sales call. Over time, hitting those numbers becomes easy as the funnel grows with prospects to follow-up on.

Opening → Qualifying → Progressing

My LinkedIn conversations are short and to the point as people tend to be more in-and-out on that platform than on Facebook.

I use a casual tone and write as I would speak (pretend you’re writing these getting in and out of an Uber).

I ask no more than 3 questions to decide if I want to advance them to a quick chat where I'll finish the qualification process.

I stay away from open-ended questions such as "Tell me more about your business". No one has time for that and you’ll only trigger sales pressure.

Instead, go straight for a non-friction question where they are given a “this or that” option to answer with (kind of like how a chatbot works).

The only thing I sell at this point is 15 minutes with me to see if I can help them or not.

I'll reduce their resistance by offering value and avoiding words that trigger sales pressure. For example, “Not sure if you’d be interested in this or not, but might have some ideas which could help you solve this problem”.


5. Discovery Call

When someone agrees to a quick chat (discovery call), I will book for the following day or two days away at the latest.

Past that, I experience a higher no-show rate.

The discovery call is there for me to complete the qualifying process and build rapport. By checking out their LI profile and pre-qualifying through DM, most are.

After those 10-15 mins, I know if I can help them or not and know if they are serious about solving the problem I have the solution to.

I then ask them if they’re open to having a second call where we can dive deeper into fixing their problem.

Some prospects will want to continue the call there and then, but I always push for a second session 24-48 hours later.


Not only does it build more trust because you’re showing you’re not desperate for the sale, it gives you more time to prepare for the consultation.

On that call, I will recap their situation, where they want to go, why they can't get there by themselves, and make sure I understand everything on a deep level.

Then I dive into explaining how I'll help them and how much the investment will be.

Rockblocks I Experienced and How I Overcame Them

This process is something I've stuck to for the past couple of years. I've gone from pitching my services back in 2019 to focusing on creating content and attracting people in 2021, when LinkedIn restricted connection request limits to 100 per week.

Here were my biggest roadblocks:

1) Getting people to respond back to my DMs
I was making it too generic. People are busy and have other crap to do than explain to strangers "how their business is doing".

2) Getting the right people to see my posts
LinkedIn isn't like Facebook. The day I wrote content for LinkedIn is the day I saw an improvement in my post engagement.

3) Converting DMs into quick chats

For the longest time, I was either pitching or chatting. Both are wrong. I figured out what I needed to ask and then found the CTA that worked best for me: "Would you be comfortable having a quick chat to see if I can help you with that?"

BONUS: 3 Examples of My LinkedIn DM Strategy In Action


LinkedIn Messages

So here are a few years of LinkedIn experimenting for you. Hopefully, this will help accelerate things for those of you trying to make that platform work for your business.

P.S. If you’d like me to audit your profile or outreach messages, shoot me a message.



Gareth’s Ten Commandments For Using LinkedIn

1. Thou shalt not be needy. No one wants to work with a desperate weirdo.

2. Thou shalt not send links, or files without prior approval. People do this all the time, and it’s a huge turnoff. It never works.

3. Thou shalt remain conversational and keep messages as short as possible. Before you send a message, record yourself saying it. If it sounds weird, start over. If it sounds smooth and conversational, send the message.

4. Thou shalt ask questions which reveal questions about a prospect’s situation. In other words, questions which a) help you determine if a prospect is qualified and b) lowers their sales barrier

5. Thou shalt offer value without expecting anything in return.

6. Thou shalt not trigger sales pressure. People don’t want to be sold to so choose your words carefully. Use indirect language and never say you can “definitely” help someone.

7. Thou shalt limit questioning to three. Anymore, and the prospect might lose interest. Like a fish, you need to jig the rod a few times. Jig too much, and the fish will slither away. Ask a few questions, see if they’re a fit, then suggest the call.

8. Thou shalt follow-up. Only 3% of the people you target are ready to buy today. 50% will never buy. And the remaining 47% will buy tomorrow or within the next two years so you MUST follow up. If you’re not following up, someone else is. The secret to follow up is offering value (e.g. mini lead magnets, invitations to webinars, case studies), and NOT messaging them every week saying “Hey Gareth, just following up. How are things going?”. I’ve followed up with prospects for 1+years before they pulled the trigger and became clients. Test various messages, and set up your sales CRM to notify you to follow up every month, quarter, etc.

9. Thou shalt post or comment at least 1 time per day. This will keep you in your prospect’s newsfeed. You’ve got to stay top of mind.

10. Thou shalt use VIDEO. Sending video DMs is one of the biggest hacks on LinkedIn. It builds trust and breaks resistance. Don’t be afraid to send a video message, but keep them under 1 minute in length, and don’t be a weirdo.




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