LS #59: Why LinkedIn outreach still fails in 2025 (3 new mistakes everyone's making)
LinkedIn outreach used to be simple. But that playbook is dead. Buried. Cremated...
Hi there,
I look at what works on LinkedIn to help you craft content people engage with.
In this issue, you'll find:
The 3 high-performing LinkedIn posts this week
Why LinkedIn outreach still fails in 2025 (3 new mistakes everyone's making)
The 3 high-performing posts this week
1. What a business model.
Why this post went viral?
This post went viral, receiving almost 310 likes in a day. It received 25-38 more engagement and views than James's posts this week.
This post hit 3 things people love: finding out about easy money, seeing the real math behind a business, and learning about a cool new sport. Everyone enjoys discovering that a simple business they see around town actually makes tons of money. James sounded genuinely curious instead of trying to sell something, and admitting he was bad at the sport made him seem like a regular person. Plus, padel is getting really popular right now, so people were already wondering if it could make money.
BREAKDOWN
Simple admiration hook: "What a business model." - understated amazement that draws people in
Clear pricing structure: "~£50 per court per hour, 5 courts" - immediately shows the revenue potential
Back-of-napkin math: Shows his thought process calculating revenue step by step. "16 hours a day" and "70% usage" - realistic business projections. "£2k profit per day" and "£60k a month" - gets to the money quickly.
HOW TO CREATE YOUR OWN POST:
Start with understated amazement: Use simple phrases that show you're impressed without being over the top
Show the math publicly: Walk people through your revenue calculations so they can follow along
Make realistic assumptions: Don't use perfect scenarios - show what 70% capacity actually looks like
Get to the bottom line: People want to know the actual profit, not just revenue
Ask for insider knowledge: Show you want to learn more from people who actually know
POST IDEAS FOLLOWING THIS TEMPLATE:
"Car wash business model breakdown - the math is incredible"
"Mini golf course revenue - never thought about this before"
"Dog daycare economics - £30 per dog per day adds up fast"
"Self-storage facilities - the margins are insane"
"Escape room business model - £25 per person, 6 people, 1 hour"
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2. A few years ago, someone pointed at Forbes magazine on the table.
Why this post?
Another post that went viral this week—it got 585 likes in 3 days and performed 3.5-14 times better than Amanda’s other posts this week.
WHY THIS POST WENT VIRAL
This post worked because it showed the huge gap between where someone starts and where they can end up. People love seeing proof that impossible dreams can actually happen, especially when the person was young and doubted themselves. The Forbes 30 Under 30 list is something many entrepreneurs dream about, so seeing the real journey from laughing at the idea to actually making it happen was inspiring. The photos from the summit made it feel real and showed she truly belonged there, not just got lucky.
BREAKDOWN:
Humble origin story: "A few years ago, someone pointed at Forbes magazine on the table" - starts with casual moment
Self-doubt setup: "I was about 19 or 20" and "just hoped it would survive" - emphasizes how young and uncertain she was
Honest business state: "few thousand subscribers" and "hadn't even started monetizing" - shows humble beginnings
Achievement reveal: "landed on the Forbes 30 under 30 2024 list" - delivers the big news
HOW TO CREATE YOUR OWN POST:
Start with a small moment: Find a specific memory where someone suggested something that seemed impossible
Show your past mindset: Explain why you laughed off or dismissed the suggestion back then
Reveal your actual situation: Be honest about how small or struggling your business really was
Include struggle periods: Don't make it seem like smooth sailing - mention the hard times
Build to the achievement: Make people wait for the big reveal of what actually happened
3. The right moment never comes.
Why this post?
This post performed 3-100 times better than Hanna’s other posts this week.
WHY THIS POST WENT VIRAL
This post attacked the most common excuse people make for not pursuing their goals - waiting for the "right time." The handwritten message on concrete made it feel authentic and urgent, not like typical polished business advice. People could instantly relate to being stuck in the same place as last year, and the simple 10-minute starting point made change feel possible instead of overwhelming. The raw honesty about feeling terrible some days made it realistic rather than motivational fluff.
BREAKDOWN:
Brutal truth opener: "The right moment never comes" - destroys the biggest excuse people make
Perfect visual: Handwritten message on concrete that looks raw and authentic
Powerful quote: "Scariest place to be is the same place as last year" - fear-based motivation
Practical breakdown: "Start with 10 min today. 10 minutes tomorrow" - makes it feel doable
HOW TO CREATE YOUR OWN POST:
Challenge the biggest excuse: Find the most common reason people give for not starting
Flip responsibility: Show them they have more control than they think
Use raw visuals: Handwritten notes or street art feel more authentic than polished graphics
Give tiny first steps: Break the big scary goal into something they can do today
Acknowledge the struggle: Don't pretend it's easy - admit there will be bad days
LinkedIn Guide
Why LinkedIn outreach still fails in 2025 (3 new mistakes everyone's making)
LinkedIn outreach used to be simple.
Send a connection request. Wait 2 days. Send a pitch. Book a demo.
That playbook is dead. Buried. Cremated.
Yet I watch founders still using 2020 tactics in 2025, wondering why their response rates are 2% instead of 20%.
The game evolved. The players didn't.
The 2025 LinkedIn Reality Check
What changed in the last 3 years:
LinkedIn algorithm prioritizes engagement over connections
Buyers became immune to traditional sales sequences
AI tools flooded inboxes with even more generic outreach
Trust became the new currency (and it's harder to earn)
The result:
Average response rates dropped from 15% to 2%
Connection acceptance rates fell 60%
Sales cycles increased 40%
Buyers actively avoid "salesy" profiles
Meanwhile, smart founders adapted and are still booking 15-20 demos per month from LinkedIn.
The difference? They stopped making these 3 new mistakes.
New Mistake #1: The AI-Generated Outreach Trap
What Everyone's Doing Now:
Using ChatGPT and other AI tools to write "personalized" outreach messages at scale.
Example of AI-generated outreach: "Hi [Name], I noticed your impressive work at [Company] and thought you might be interested in our innovative solution that helps companies like yours achieve better results. Would love to schedule a brief call to explore how we can help [Company] reach new heights."
Why it fails in 2025:
Recipients can spot AI-generated messages instantly
Everyone's using the same AI prompts
Generic compliments feel robotic
No actual personalization or research
The Fix: The Human Signal Strategy
Instead of AI-generated messages, use the "Human Signal" approach:
Step 1: Find a specific, recent post or achievement
Step 2: Reference something only a human would notice
Step 3: Add a personal experience or genuine insight
Step 4: Make it about them, not you
Example of human signal message: "Hi [Name], saw your post about the challenges of scaling customer success from 100 to 1000 customers. The point about maintaining personal touch while automating workflows really hit home - we went through the exact same struggle at [Company] when we scaled from 200 to 2000 users.
The solution we found (hiring CSMs by customer segment, not just territory) might be relevant to what you're navigating. Happy to share what worked if you're still experimenting with approaches."
Why this works:
Shows you actually read their content
Demonstrates genuine understanding of their challenge
Offers value based on real experience
No immediate sales pitch
New Mistake #2: The Content Creator Confusion
What Everyone's Doing Now:
Posting motivational content and business advice to "build authority" before doing outreach.
Example of creator-focused content: "5 lessons I learned as an entrepreneur:
Persistence pays off
Focus on customer value
Build a strong team
Embrace failure
Stay hungry"
Why it attracts the wrong audience:
Gets engagement from other entrepreneurs and content creators
Doesn't attract your actual buyers
Creates an audience of people who will never buy
Dilutes your message to decision-makers
The Fix: The Buyer Magnet Content Strategy
Create content that attracts people with the problems you solve:
The Problem-Results-Method Framework:
Step 1: Share a specific business problem you solved
Step 2: Show measurable results you achieved
Step 3: Hint at the method (but don't give everything away)
Step 4: Ask who else faces similar challenges
Example of buyer magnet content: "How we reduced our customer acquisition cost from $150 to $45 in 6 months:
The problem: Our conversion funnel had a 2% signup rate on our landing page.
What we tried first (that didn't work):..."
Why this works:
Attracts founders with CAC/conversion problems
Shows specific, relatable results
Demonstrates problem-solving capability
Comments reveal qualified prospects
New Mistake #3: The Connection-First Mentality
What Everyone's Doing Now:
Still focusing on getting connections before building relationships.
The old approach:
Send connection request
Wait for acceptance
Send follow-up message
Pitch your service
Why it fails in 2025:
Connection acceptance rates are at all-time lows
People connect but ignore messages
No trust built before the ask
Feels transactional from the start
The Fix: The Engagement-First Strategy
Build relationships before asking for connections:
The 7-Day Engagement Sequence:
Day 1-2: Like their last 2-3 posts
Day 3-4: Leave thoughtful comments on their posts
Day 5-6: Share their content with your perspective added
Day 7: Send connection request referencing the conversation
Why this works:
Builds genuine familiarity before connecting
Shows you're paying attention to their content
Creates reciprocity (you've added value first)
Connection request feels natural, not forced
The 2025 LinkedIn Outreach Framework
Phase 1: Research and Qualification (15 minutes per prospect)
Review their recent LinkedIn activity
Check company news and funding
Identify specific challenges they've mentioned
Qualify fit using BANT criteria
Phase 2: Value-First Engagement (7 days)
Engage with their content meaningfully
Share relevant insights from your experience
Build recognition and familiarity
Position yourself as a peer, not a vendor
Phase 3: Connection and Conversation (Ongoing)
Send contextual connection request
Continue providing value through messages
Share relevant resources and insights
Let them bring up business challenges
Phase 4: Soft Transition to Business (When appropriate)
Reference their specific challenges naturally
Share relevant case studies or results
Offer to discuss their situation in detail
Move to phone/video when interest is shown
What Works in 2025: The New Outreach Playbook
High-Converting Message Templates:
The Insight Message: "Hi [Name], your post about [specific challenge] reminded me of something we experienced at [Company]. We found that [specific insight] made a huge difference. Not sure if you've tried this approach, but happy to share more details if it's relevant to what you're working on."
The Resource Share: "Hi [Name], saw you mention [challenge] in your recent post. I actually just wrote about this exact issue based on our experience solving it at [Company]. No pitch, just thought it might be useful given what you're dealing with. [Link to relevant content]"
The Introduction Offer: "Hi [Name], noticed you're working on [specific challenge]. I know someone who just solved this exact problem at [similar company]. Would an introduction be helpful? No agenda on my end - just think you'd have a good conversation."
The 2025 LinkedIn Outreach Formula
Human-Led Personalization (not AI-generated) + Buyer-Focused Content (attracts the right audience) + Engagement-First Approach (build trust before asking) + Value-Driven Messaging (help before you sell) = Outreach that actually works
Stop using 2020 tactics in 2025. The buyers evolved. So should you.
That's a wrap for today.
See you next week! If you want more LinkedIn tips, be sure to follow me on LinkedIn (link).
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Your compadre,
Anton "LinkedIn growth strategies" Cherkasov
Even with low outreach on LinkedIn, the organic distribution via content is still better than any other platform I've been on. Plus the calibre of leads is 10x anywhere else