Outreach Playbook

Takeaways

In this playbook, I'm going to give you 7 simple steps to help you:

1. Find prospects without having to scrape lists or cold messaging required.‍
2. Track and manage outreach in a simple pipeline so no opportunities slip through the cracks.‍
3. Create LinkedIn messages that actually get responses using a proven structure.‍
4. Handle different types of replies and naturally guide the conversation toward a call.‍
5. Follow up the right way to increase response rates without being annoying.
6. Automate use AI to scale up without spamming or burning your pipeline‍
7. Use best practices for ongoing success and turn LinkedIn into a steady source of sales calls.

Reading time: 15 minutes

Introduction

Most outreach on LinkedIn fails.

Messages go unread. Conversations don’t start. And even when someone does respond, it’s usually just a polite "no, go away."

I've been there.

In 2024, I spent weeks firing messages into the void and got absolutely nowhere.

It sucked. No wait, I sucked. It was hard, embarrasing at times.

It took me months of trial and error before I finally cracked it.

The problem wasn't LinkedIn.

The problem wasn't because "outreach is dead".

The problem was I was treating LinkedIn like 99% of GTM teams - like an email list, sending generic, templated messages to anyone who fits their ideal customer. Which worked, once upon a time. Probably.

But not anymore.

Here’s what I had to learn (the hard way - as a result of getting it wrong):

LinkedIn isn’t an email inbox. It’s a social platform, and people expect something real, more authentic. If you're like me, you're beyond saturation point with ‘cold pitches’ and getting 'pitch-slapped' by every Tom, Dick and Harry.

There's good news though. There’s a better way.

And that's what this playbook is all about.

So you can learn from my mistakes, avoid wasting time guessing at what to do, and actually get results.

I'm going to show you how I generate 5-10 conversations everyday, how I booked 22 high-ticket sales calls last month using this very system.

It’s the same system that got one our clients 105 sales calls in just 6-8 weeks.

In fact, here's the email that Simon [our client] wrote referring us to an associate ↓

Instead of firing cold pitch after cold pitch to complete strangers - you  warm them up first.

We'll be covering how to take a cold lead and make them warm, and how you can focus on the people who have ‘already shown interest’. People who have engaged with your content, viewed your profile, or followed you, and so on.

The warmer the lead, the more likely they'll respond, start a real conversation, and ultimately book a call, sign up or subscribe to what you offer.

I’ll break down a structured, repeatable process you can use to:

• Find the right prospects without scraping lists or relying on bad outbound automation (though I’ll touch on that too)
• Start personalized conversations that actually lead to calls or signups
• Qualify leads without making them feel like they’re being interrogated (and burning a bridge)
• Book more sales calls without sounding ‘salesy’, pushy, desperate, or finding it cringey

If you’ve been feeling stuck, struggling to turn LinkedIn conversations into booked meetings, I’ve spent a long time testing, troubleshooting and falling flat on my face on your behalf.

I hope this single playbook can save you hours of wasted time, so that your efforts start giving you a measurable ROI.

Let’s get into it.

Why warm outreach works better than cold outreach.

Most LinkedIn outreach fails because it’s cold and impersonal.

People are bombarded night and day with copy-pasted connection requests and endless, lazy cold pitches disguised as friendly intros. The bar is on the floor where "personalization using AI" is concerned.

So people have learned to ignore all messages that feel automated, or even remotely scripted.

The issue with cold outreach is that it forces you to convince strangers to talk to you. That’s hard. Even with a killer message. Warm outreach does the opposite. It leverages existing engagement to start conversations with people who already know who you are, to some degree. And that’s much easier.

The difference (in a nutshell)

Cold outreach:

• Sending messages to people who have never heard of you
• Relying on generic templates that could be sent to anyone
• Getting ignored 99% of the time

Warm outreach:

• Messaging people who have already engaged with you in some way
• Making every message personal and relevant
• Getting a much higher response rate because they recognize your name

But where to start?

Where to find warm prospects on LinkedIn

We’ll get into this in more detail shortly, but your best leads are ‘already interacting with you’, you just need to know where to look.

At a top level, here’s where to find them:

1. Profile views – These people took the time to check you out. They saw your content or searched for you directly. Either way, they already have some level of interest. (This is largely the result of optimizing your headline - more on that soon).‍
2. Likes and comments on recent posts – If someone is engaging with your content, they’re aware of you and your expertise. That makes them a natural person to start a conversation with.‍
3. Recent followers – When someone follows you, it means they find your content or offer valuable. Even if they haven’t engaged yet, they’re paying attention.

I always start with profile views first. These are the warmest prospects because they actively looked me up. Then, I move to engagement on my content, I check my recent followers, and then I warm up a qualified list of my ideal buyers.

Instead of wasting time on pitching completely cold prospects, I focus on people who are already somewhere in my orbit. That alone massively increases my odds of getting responses.

Here’s how:

Step 1: Finding the right prospects

Remember, the goal here isn’t to build and blast a massive list of 1M+ ‘ideal prospects’. Believe me, the 'spray and pray' approach is as effective as doing this:

“Surely one went in!?”

“Surely we’ll get one sales call… surely!?”

No.

You won’t.

It doesn’t work.

You’ll never get leads this way.

At best, a hand-full of unqualified calls.

If you’ve tried the spray and pray approach before, you don’t need reminding of the frustration you felt. And if you’re thinking of trying it, I’m about to save you hours of headache (and heartache).

The goal is to identify a focused group of high-quality prospects, people who are already aware of me and are most likely to engage in a conversation.

So, let's take a deeper look at the three primary sources:

1. Profile views

The best place to start is with people who have viewed your LinkedIn profile. If someone took the time to check out my profile, there’s already some level of curiosity.

In my case, they might have seen my content, saw a comment I made somewhere, heard my name mentioned, or searched for a solution I provide.

To find them:

1. Go to “My Network” on LinkedIn.
2. Click “Who’s viewed your profile.”‍
3. Scroll through and take note of anyone who matches your ideal client profile (ICP).

How to qualify profile viewers:

• Do they match the industry, job title, or company size I typically work with?
• Are they decision-makers or influencers in the buying process?
• Have they engaged with my content before?
• And so on… (based on however you qualify your ICP)

If the answer to any of these is ‘yes’, they go on my prospect list (we use HubSpot), and then I prospect them.

2. Engagement on recent posts

If someone has liked or commented on my LinkedIn post, that means they’ve already engaged with my ideas. That’s a strong signal they might be open to a conversation.

To find them:

1. Open my latest posts.
2. Click on the reactions (likes, claps, etc.) and scroll through the list.
3. Check the comments to see who’s actively discussing the topic.
4. Identify who fits my ICP.

How to qualify people who engage with my content:

• Is their comment thoughtful, or are they just leaving generic engagement?
• Have they engaged with my content more than once?
• Do they fit my ICP based on their profile?

People who comment are usually more engaged than people who only like a post. So I prioritize them first, before those who just liked my content.

3. Recent followers

When someone follows me, they’re signalling interest in my content or what I do, and have shown they want more (they want me in their feed). Even if they haven’t engaged yet, they’re paying attention.

N.B. Nearly all booked calls come from LinkedIn's "silent" users. These people quietly read and watch content but never engage, they simply follow. In fact, some of my ‘lowest performing’ posts (low impression count) brought in the highest ticket leads.

To find them:

1. Go to “My Network.”‍
2. Click on “Followers.”‍
3. Scroll through the list and check profiles to see who fits my ICP.

Since these people already made the choice to follow me, they’re much warmer than a completely cold lead.

How to qualify new followers:

• Did they follow me after a specific post?
• Do they match my ICP in terms of industry, role, company size, and so on?
• Have they followed similar people in my space?

As I mentioned, even if a follower hasn’t engaged yet, they’re still a good candidate for outreach. Sometimes, they’re just passive consumers of content, and a direct message is what gets the conversation started.

4. Using Sales Navigator

Sales Navigator is unlike any other tool on any other platform. Why? With paid ads on Facebook, for example, you can only get in front of groups of people who might be the right fit - it still works, but you’re targeting audiences, not individuals.

With Sales Navigator, it’s the opposite. You can pin-point specific decision-makers. And finding them couldn't be easier. It lets you build a list of exact people who match your ICP, one by one, instead of hoping the right person happens to see your ad.

Here’s exactly how I use it:

1. Set filters for my ICP. I create a tight search in Sales Navigator so I’m only looking at people who are highly likely to buy (role, industry, company headcount, geography, etc.).
2. Send 20–30 connection requests a day. I send these requests without a message attached. Most templated intros feel like a pitch and get ignored. A clean connection request has a much higher acceptance rate.
3. Turn connections into warm prospects. Once they accept, they automatically become a follower by default.

That means:

• They start seeing my content in their feed
• I can engage with theirs
• We both build familiarity before any direct conversation starts

Done consistently, this keeps my pipeline full of fresh, relevant prospects. Every new connection is a silent “yes” - an opening to warm them up over time.

And yes, I’ll show you how you can automate parts of this without risking your LinkedIn account being shut down (more on that a bit).

Prioritizing outreach: Warmest to least warm

Not all warm leads are created equal. Some are hotter than others, and it makes sense to prioritize them in the right order.

I break my outreach into three levels:

1. Hottest prospects: Profile viewers‍
2. Warm prospects: People who engaged with my content (commenters first, then likes)‍
3. Lukewarm prospects: Recent followers who haven’t engaged yet (including any connections from sales navigator)

Having tested this a while, here's something interesting - connection requests that get accepted will often cause to the prospect to check out your profile -which makes them a much warmer prospect. Why? Because when you send them your first message, you're not a complete stranger.

I always start with the hottest prospects first before moving down the list. This increases my chances of quick wins and keeps my pipeline filled with high-quality conversations.

Before moving on to the next step, I aim to gather at least 20-30 high-quality prospects to prospect that week (around 5 a day). This gives me enough volume to work with without overwhelming myself.

(And yes, there are ways we automate this process - we’ll get to that)

Next step: Now that I have my list, it’s time to record and track everything.

Step 2: Recording prospects in a pipeline

Once I’ve identified my prospects, the next step is tracking them properly. Keeping my outreach organized prevents leads from slipping through the cracks, helps me stay consistent, and makes follow-ups much easier. And let's face it - LinkedIn DMs aren't the best user experience. It quickly gets messy - so we need a system.

A scattered outreach process leads to missed opportunities. Without a system in place, it’s easy to lose track of conversations, forget who I’ve already messaged, or fail to follow up at the right time.

Choosing the right tool

I use Flow's CRM for tracking my LinkedIn outreach, but any CRM, Notion database or spreadsheet will work. The important thing is having a simple way to:

• Record prospects before reaching out
• Track who I’ve messaged and when
• Update their status based on their response

The tool itself doesn’t matter as much as the process of staying organized.

You can download our free Notion pipeline template, if it’s helpful.

Why tracking matters (without stating the obvious)

LinkedIn is messy.

The interface is actually quite clunky compared to most other platforms.

So keeping a clear pipeline ensures that any efforts across multiple open tabs don't get lost. There’s nothing worse than realizing you haven't responded to a lead and missed a potential sale.

I’m not telling you to suck eggs - this is, I’m sure, very familiar given your expertise and line of work.

But without a pipeline, outreach on LinkedIn quickly becomes a guessing game - it’s not quite the same as managing cold emailing in Apollo.io and prospects deal stages updating automatically.

For me, conversations get lost in my inbox, follow-ups get forgotten, and the bottom line? I end up just wasting time, needlessly.

By recording and tracking everything, I:

• Always know exactly who I’ve reached out to and when
• Can follow up strategically instead of randomly
• Have a clear view of my progress and response rates

I know this seems obvious, but have witnessed it even in high-performing GTM teams.

How to track prospects automatically

I mentioned earlier that I use Flow’s CRM - it’s available for most of our customers too, and I love it. It automatically tracks conversations with ideal buyers and nudges me to follow up using smart logic based on buyer intent, ICP-fit, time since the last message, and so on.

Personally, I’ve always hated this side of prospecting - the boring admin work. Flow takes that completely off my plate. It frees me up to focus on what actually matters: starting conversations and booking sales calls. And the best part? I never have to worry about missing a lead or leaving money on the table.

Whatever tool you decide on, with my pipeline set up, I’m ready to start creating my first outreach message.

Step 3: Defining an outreach question that works (with examples and screenshots!)

Now we get to the part you've been waiting for.

Here’s the formula we’ve used to get as high as a 50% response rate for specific campagins. This is a typical week, give or take ↓

(Of course, these results depend on having key elements in place: like a compelling offer, the right message, well-defined target audience, authoritative content, and so on).

Now, important thing to remember - most LinkedIn outreach fails because it’s either too aggressive, too ‘salesy’, too jargon-y or AI-sounding, or too vague.

Some messages jump straight into a pitch, which turns people off immediately. Others are so open-ended that they give the prospect no reason to respond.

A good outreach message needs to do two things:

1. Make it easy for the prospect to reply - the simpler the question, the better.
2. ‍Lead naturally to a sales conversation - without making the prospect feel like they’re being sold to.

The best way to achieve both is to ask a qualifying question that uncovers a goal or pain point.

The structure of a good qualifying question

N.B. this step (step 3) will only work if it’s paired with everything in step 4 - so keep reading. A good qualifying question is only half the fight.

Now I use a simple formula for my outreach question:

“How’s [goal / outcome you provide] progressing - is it going well / proving fruitful?”

This question works because:

• It’s easy to answer – It’s a yes/no question, which removes friction.‍
• It quickly reveals if they have a problem – If things aren’t going well, they’ll tell me.‍
• It naturally leads to a follow-up conversation – I can continue the discussion based on their response.

Examples of effective outreach questions (with real-life screenshots)

The specific goal I reference depends on what I help clients with. Here are a few examples:

• If I help companies with lead generation:
  “How’s LinkedIn lead-gen going for you and the team - is it going well / proving fruitful?”

• If I help executives with leadership coaching:
  “How’s team performance been lately for you as [title] - are they smashing it?”

• If I work in AI and automation‍
  “Mind me asking how AI has been impacting you - is it proving fruitful / been easy to implement?”

The goal is to ask a question that makes the prospect think, “Actually, things could be better…”

• If they have a problem, they’ll likely mention it.
• If they’re doing well, I can pivot the conversation by asking about their next goal (which I’ll cover in the messaging step).

Here’s the qualifying question I typically use:

Why this works better than generic outreach

Most outreach messages either:

• Go straight into a pitch (“We help companies generate more leads. Our company is [very prestigious], and we’ve helped [all these clients]. Let me know if you’re interested.”)‍
• Are too broad to spark a conversation (“How’s business going?”)

A good outreach question sits in the middle, specific enough to be relevant, but open enough to encourage a reply.

Once I’ve defined my outreach question, I’m ready to create my ‘icebreaker’.

Step 4: Creating the ice-breaker

Now that I have my list of prospects and a strong qualifying question, it’s time to create the first message / aka. ‘icebreaker’. This is where a lot of outreach goes wrong.

The goal isn’t to sell or pitch immediately. It’s to start a genuine conversation that can lead to a booked call.

What the first message should accomplish

The first message needs to do two things:

1. Break the ice with a personalized compliment – this shows the message isn’t copy-pasted and makes the prospect more likely to engage.‍
2. Ask the qualifying question (which we covered in the previous step) – this moves the conversation toward discovering a potential pain point or challenge.

Writing a personalized compliment (the first part of your message)

A personalized compliment makes the message feel genuine and shows that I’ve put thought into reaching out. It should be specific, short, and relevant to the prospect.

Why?

Without this personal touch, you're violating a fundamental, age-old rule that most modern-day sales professionals have completely forgotten about.

I think it was best put by Earl Nightingale from ‘Lead the Field’ (circa ~1950). And I quote…

“Have you ever stopped to think of this. Every human being on earth is the most important human being on earth, as far as he or she is concerned. You may never get anyone to admit it, but it’s a fact. There’s nothing in the world that men, women, and children want and need more than the feeling that they’re important, that they’re seen, validated, needed and respected. They will give their love, their affection, their respect, and their business to the person who fills this need… ”

In recent years, quotas, 'signal' data and balance sheets have taken precedence over some very basic fundamentals. It plagues most sales and marketing teams today.

By forgetting the basics, teams have become distracted and now rely on gimmicks to win attention (we even had an enterprise client who used to givew away gift cards just to get people on a call - expensive and innefective)

We’ve all been on the receiving ends of outreach.

That's why the majority fail to cut through the noise.

So, where to find something to compliment:

1. Recent content – If they’ve posted something interesting, highlight it.‍
2. Their profile – Look at their About section, experience, or any awards/achievements.‍
3. Their product or service – If they have strong offer, cool features or great branding, mention it.‍
4. Common ground – If I see something we share in common (e.g., industry experience, mutual interests), I’ll reference that.

In my honest opinion, these aren't the best ice-breakers I've written (I'd say they're pretty average), but you can see that simply acknowledging prospects triggers a completely different response, when done right.

All you have to think about is - how do I make this specific person feel seen, feel recognised, or significant?

Guidelines for writing a good compliment

1. Be specific – Instead of “I liked your post,” say, “I loved your take on [specific topic]. Especially what you said about [xyz].” If it can be copied and pasted for anyone, it’s likely going to have less impact.‍
2. Keep it short – A couple of lines are enough. Long compliments can feel forced. I try to stick to a rule of max 2-3 lines for both my ice-breaker compliment and qualifying question.‍
3. Make it relevant – Compliment them on something they likely care about (e.g., a founder will care deeply about their product, not their favorite TV show). Always relate it to professional topics that matter most to their role as CEO, VP of Marketing, etc.‍
4. Avoid being overly formal – This should feel conversational, not like a corporate email. Use simple language, no jargon or clunky corporate speak. ‘8th grade-level English’ will get much better results (… works great as a ChatGPT prompt too).

Examples of good compliments:

Bad example: “Hey [Name], nice profile!”

Good example: “Hey [Name], I enjoyed your recent post on scaling teams. I think we all wish we'd learned the "hiring slow and firing fast" principle sooner :)”

---

Bad example: “Hey [Name], great job on your branding.”

Good example: “Hey [Name], the branding on your site it killer. Just watched your video on [provide specific reference]. Congrats :)”

Putting it all together

Now that I have my compliment and qualifying question, I combine them into a simple, conversational message.

Template for the first message:

“Hey [Name] - [compliment] :)

How’s [goal] going Is it going well?”

This message feels natural, opens the conversation, and leads the prospect toward discussing a potential challenge or goal.

When you’re new to warm outreach, it always involves a bit of trial and error, and sometimes leading with a compliment alone is enough to open the conversation:

Avoiding common mistakes

1. Don’t make the message too long – The prospect should be able to read it at a glance.‍
2. Don’t jump straight into a pitch – This feels pushy and turns people off, always. Save the pitch for the sales call.‍
3. Don’t use overly formal language – LinkedIn is a social platform, so the tone should be conversational.‍
4. Don’t send generic compliments – If the message feels copy-pasted, they’ll know, and it’ll likely be ignored.

With my first message sent, the next step is knowing how to handle different types of responses.

Step 5: Managing Replies

This is the bit people often find hardest. Once I send the first message, the real work begins.

Outreach isn’t just about sending DMs, it’s about managing responses to fully qualify the prospect and then guide the conversation toward a call. This is where most people either get stuck or come across as too pushy.

I break responses into two categories:

1. They have a problem (ideal response) – Move toward a call.‍
2. They don’t have a problem (or they say things are “going well”) – Dig deeper and shift the conversation.

How I respond depends on what they say, but the goal remains the same: keep the conversation moving and get them on a call.

Here’s a top shot of what the workflow looks like:

If they signal “it’s not great” (Path 1)

This is the best-case scenario. If someone says they’re struggling with their goal, they’re opening the door for a deeper conversation.

How to respond:

1. Acknowledge what they said – This makes the conversation feel natural instead of transactional.‍
2. Offer a call to help them solve the problem – Keep it low-pressure and framed as a conversation, not a pitch.

Acknowledge: “I hear you Mohsin :) LinkedIn can be incredibly adbundant, but has quite a few moving parts, so to speak.

‍Ask for call: Wondering if I can help fill your pipeline - is it worth us jumping on for 20 mins and I can show you a proven system we use for clients?

If they signal things are “going fine” (Path 2)

Not every prospect will immediately admit to a problem. Some might say things are fine, even if there’s room for improvement.

Instead of ending the conversation (like the majority do), I shift the focus to their next goal.

How to respond:

1. Acknowledge what they said – This keeps the conversation natural.‍
2. Ask about their next goal – Give them multiple options to make it easier to answer.

Example response:

This works because it gently nudges them toward thinking about areas where they could improve. If they share a goal that aligns with what I help with, I can transition to a call.

The angle here is that “I’m helping them hit that goal faster”.

If they throw me a ‘curve ball’… (less common)

In the case above, it was a perfect fit (right timing, ideal customer profile, etc.). However, there will be times when prospects raise objections, or are on to you - and will simply ask you to "pitch it."

In the following example, I was asked exactly that after my outreach question. Dimitris didn’t answer the outreach question, but instead came back with: “What’s your offer?”

In this example, I’m still using the formula:

1. Acknowledge what they said – This keeps the conversation natural.‍
2. Ask a question – Give them multiple options, or to make it easier to answer.

As a general rule of thumb, if you end any message with a statement instead than a question, 9 times out of 10 - the conversation dies. Always round off your replies with a question that keeps the conversation moving towards the call.

(Imagine you’re a doctor ‘diagnosing the patient’. You ask questions to uncover pain so that you can provide the appropriate solution or followup question).

Remember, people love to talk about their problems, and they appreciate you being a listening ear.

You'll find that after a few weeks you'll be reusing many of the same talking points, as most conversations will be slight variations of the same thing.

Step 6. If they don’t respond (try these followups!)

Sometimes, a prospect will read the message and not reply. That doesn’t necessarily mean they’re uninterested, people are busy, and messages get buried. Despite us living in a golden era of tech, most of us have never been so time-poor.

I follow up once or twice.

How NOT to follow up.

The following approach worked for a time, but it won't anymore:

1. Old way: First follow-up (2–3 days later):

“Hey [Name], just bringing this to the top of your inbox, would love to hear your thoughts.”

2. Old way: Second follow-up (if needed, 5–7 days later):

“Hey [Name], totally get that things get busy. If now’s not the right time, no worries, just let me know.”

It doesn't work because it's not providing that person any value - you're asking for their attention (and time) without first earning it.

Here's how to follow up

To recap, "Nudge, nudge!" or "Tom, thoughts?" scream low-skilled, pushy salesman.

The best way to follow up is to ensure conversation never closes. So avoid any followups that go "do I have permission to close your account?" - it's missing a trick. Instead:

1. Engage meaningfully with their content. Provide value by driving significance and adding to the conversation in the comments - this is a great way to nudge a reply. "Ah, yeah - need to respond to that DM of theirs...", and so on.
2. Send a followup DM about their content. Leave a valuable comment of their post, then after a few hours (or when the comment gets read or replied to), compliment the prospect on the content. (This can also work well as an ice-breaker too)

I usually give it about week between followups. Slow, steady and consistent wins the outreach race. Too eager can come across as needy, desperate. And effects your credibility and authority.

Here's one of the best followups I've recieved, sent around two weeks after I ignored their first DM (I was the prospect in this instance):

Other followups to try

• Try sending a voice note - they're so rare and the human touch goes a long way
• Send a video - get your face on camera (nothing feels more personalized that a video)
• Provide them an asset or playbook that gives them (the why, what and when - you implement the how)
• Reference a post you wrote or a podcast episode that provides them more insight on what you do (it showcases authority too)
• Or, send a simple follow up that speaks to the outcomes you provide

I cannot emphasize enough how important follow-ups are.

The reality? People are busy, and chances are they simply haven't gotten around to responding yet.

Here an example of prospects that took a month to respond:

If totally dead in the water, I move on and update their status in my pipeline.

Step 7. Positioning a call

Once a prospect has shared a problem or a goal, the final step is booking a call.

How to offer a call:

• Make it low-pressure – It should feel like a conversation, not a commitment.‍
• Give a clear next step – Instead of “Let me know if you’re interested,” I ask if they’re open to a quick call.

Example call invite:

If they agree, I send them a link to book a time.

If they say no, I keep the relationship warm for future opportunities. (There’s literally no harm sending “Wishing you all the very best for the coming weeks. Bye for now.”)

We also teach our clients proven techniques (if you don't already use them) that create urgency, scarcity, and motivate prospects to take action,  without being pushy.

Can you automate this?

Short answer - yes.

Doing this 25+ times a week won't cost you anything – but it's exhausting, and it will burn you out (unless you love doing it or you're a full-time SDR). And you may not even have the time to begin with to do this manually. Doing this at scale requires the right system, and the right tools. But most individuals will use a tool like HeyReach and spam a list of leads with the same blanket message.

I use an Agent Maya.

How Agent Maya works:

1. Maya sends out those first outreach messages to get conversations going.
2. Once they reply, she jumps into your messages and guides it toward a call.
3. She'll read your profile, understand your offering, check out who you're prospecting, and suggest the perfect replies.

All while following this proven playbook to get you from that first icebreaker to a sales call.

And if you want to keep control, you can tweak her suggestions before hitting send.

See how in 90 seconds

Managing responses in my pipeline

As I mentioned, I use Flow's CRM to track all of this automatically. But if doing it manually after each response, I'd then update my Notion pipeline to reflect the next step:

• ‍If they book a call → Change their status to “Meeting Booked.
• If they’re interested but not ready yet → Change their status to “Future Follow-Up.
• If they aren’t interested or don’t respond → Change their status to “Not Interested.”

And so on.

This ensures I always know where each conversation stands and never lose track of potential opportunities.

(Must read!) The 8 rules of LinkedIn outreach

Outreach works best when it’s consistent, personalized, and structured.

But even with the right process in place, if you begin defying some of these basic rules, it can lower response rates and make conversations feel forced.

To keep my outreach as effective as possible, I follow these best practices.

1. Approach outreach with curiosity, not salesmanship

People ignore sales-y messages because they feel like a pitch, not a conversation - it makes them feel insignificant (remember the Earl Nightingale quote above). Instead of acting like I already have the perfect solution for them, I take a curious approach.

• ‍Wrong: “I’m confident I can help you get more leads.”‍
• Better: “I’d be curious to see if I can help, worth us grabbing 20 mins together next week?”

This small shift makes a big difference.

It removes pressure from the prospect and makes them more open to talking.

2. Personalize every message

People can tell when a message is copy-pasted. If it looks like I’m sending the same thing to 100 people, they’ll ignore it.

I try to make sure every message has:

1. A specific compliment about their content, profile, or work‍
2. A relevant question tied to their industry or challenges‍
3. A natural tone that doesn’t feel robotic

For example:

• ‍Wrong: “Hey [Name], love your profile. How’s business going?”‍
• Better: “Hey [Name], I saw your post about [specific topic], really liked your perspective. Nice job :) How’s [specific goal] going for you - are things progressing well?”

3. Keep messages short and easy to read

If a message is too long, it won’t get read - it's too much effort for then, and looks like a pitch-slap. I aim to keep my first message 2-3 short sentences. The goal is to start a conversation, not explain everything in one go.

• ‍Wrong: “Hey [Name], I saw your profile and wanted to connect / build me network / have nothing else to say. I run a consultancy that helps companies generate leads through LinkedIn - me, me, oh wait, more me! We work with [company type] to create a repeatable system for booking calls. Let me know if you’d be open to chatting to buy our stuff.”‍
• Better: “Hey [Name], [short compliment they’d care about]. Congrats :) How’s [goal] progressing - Is it going well?”

Simple messages get more replies.

4. Follow up without being annoying

People get busy, and LinkedIn messages get buried. Just because someone doesn’t respond right away doesn’t mean they aren’t interested. A well-timed follow-up can double response rates.

Experiment with different followups using the suggestions above to see what lands best for your ICP.

If they still don’t respond, I move on and update their status in my pipeline. Don’t be annoying.

Sometimes they come back to you, but never when you rub them up the wrong way. Hard sells and pushy salesmanship doesn’t work in 2025.

5. Focus on booking calls, not selling in DMs

DMs aren’t the place to pitch or close deals. Did pitch once in the examples above, except when asked to?

My only goal is to start a conversation that leads to a call.

• ‍Wrong: “We help companies improve lead-gen. Want to see how we can help you?”‍
• Better: “I’d love to learn more about how LinkedIn lead-gen has been going for you guys - is it going well?”

By keeping it low-pressure, it makes it easier for prospects to say yes. There are times, however, when asking “Want to see how I can help you?” can work. But a simple principle I follow is to inject some carefully positioned social proof as part of your next question.

For instance, you might say "Yeah, a lot of our clients were experiencing that issue too. Would you be interested in learning the process we use to help them achieve [goal]?"

One I use a lot as it's every effective: "Yeah, LinkedIn lead-gen took us month of trial and error before we cracked it. Can't lie - it's proving a complete treasure trove. Happy to give you our process if it's worth grabbing 20 mins this week?"

It takes the emphasis away from selling and makes it more about education, 'helping a friend out', sharing insights or notes, etc.

6. Ask close-ended questions to make it easy to reply

If I ask an open-ended question, people are less likely to respond because it takes more effort. Instead, I ask yes/no questions to make it simple.‍

• ‍Wrong: “How’s LinkedIn working for you?”‍
• Better: “Is LinkedIn lead-gen going well for you?”

Close-ended questions make it easier for people to reply quickly, which keeps the conversation flowing.

7. Track every conversation to avoid missed opportunities

The best outreach strategy in the world won’t work if I don’t track my progress. Keeping an organized pipeline prevents me from:

• Forgetting to follow up
• Losing track of warm prospects

Every time I send a message or get a response, I update my CRM pipeline to reflect the next step. (Or in my case, I have Flow's CRM do it for me).

8. Be a real person, not a boring corporate robot

People want to connect with humans, not sales reps - we’re hard wired social creatures in desperate need for validation (don't think you're not one of them). Anyone who thinks otherwise is kidding themselves, or enlightened.

The more natural my messages feel, the better my results.

I keep my tone conversational by:

1. Dropping the corporate jargon (“synergy,” “solutions,” “cutting-edge”, "streamline efficiency" or anything that sounds like AI)‍
2. Writing like I talk, short, direct, and conversational‍
3. Injecting some personality if it makes sense (e.g., a light joke or friendly tone). No one died from being charming.

For example:

• ‍Wrong: “Hi [Name], I wanted to reach out regarding your organization’s sales pipeline efficiency and discuss potential synergies that could drive growth.”‍
• Better: “Hey [Name], well done on the recent round.  Exciting (and busy) times ahead for you and the team no doubt. Huge milestone. Congrats :)
  
  Loving your content -btw. I'd imagine you're generating a ton of calls from that - is it going well?”

When my messages feel natural, prospects respond naturally.

Final thoughts

Outreach on LinkedIn is one of the most effective ways to book more sales calls.

Instead of blasting cold messages to strangers, I focus on people who are already engaging with me, making conversations easier and response rates higher.

The biggest concern people have with this is that it’s “not fast enough”, but having been round and round for months on end, you’ll save a lot of time on cold prospecting that feels fast, but produces no results.

You have to learn the rules of engagement - you don't get to dictate them. But you can speed things up and make it way easier with the right tools and systems.

Here’s the full process at a glance:

1. Find the right prospects – Profile viewers, content engagers, and recent followers.‍
2. Track every outreach attempt – Keep a simple Notion or CRM pipeline.‍
3. Create the right message – Personalized compliment + qualifying question.‍
4. Handle responses properly – Guide the conversation toward a call.‍
5. Follow best practices – Stay consistent, track results, and refine the approach.

This isn’t about mass messaging or hoping to get lucky.

Cliché ALERT: It’s about starting real conversations that lead to real business opportunities.

When implemented correctly, this approach generating an average 5-10 natural conversations a day and 2-3 high-quality sales calls per week for clients, without feeling forced. At the time of writing, we booked 22 calls last month with one account using this method.

Whenever you’re ready, here are two ways I can help you:

1. Get started with May free
   If outreach feels like guesswork and you’re struggling to get replies and calls booked, I get it - I’ve been there. That’s why we built Maya. To take away the grind and give you a simple way to book sales calls on LinkedIn. Try Maya free today →
2. Book a call with me
   If your outreach feels stuck and you don’t know how to fix it, the answer might be simpler than you think. Book a time with me and we’ll assess what’s holding things back - then I’ll show you how to turn LinkedIn into a reliable source of qualified calls. Book time here →

🕒 This article was updated about a week ago

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