Why You’re Not Getting Conversations (Even with a Great Network)

You’re following the advice. You’ve got a decent profile. You post. You comment. You even send messages. But let’s be honest, the conversations aren’t happening. And if they are, they’re not moving anywhere meaningful. That’s not on you. It’s the system you’ve been taught. A system that glorifies visibility without intentionality. A system that treats AI as a magic bullet instead of a power tool. A system that focuses more on activity than impact.

The truth is, random acts of social selling lead to a random sales funnel. And no amount of automation or AI alone will fix that. But when you combine a trust-based strategy with the right AI prompts, designed to sound like you, for your audience, with your intent, you flip the script.

What follows is your roadmap. A way to create more conversations with the right people. To show up consistently without sounding canned. And to actually feel good about how you’re selling. Let’s go.

The Real Problem with LinkedIn for Sales (and Why AI Alone Won’t Fix It)

Most people get LinkedIn wrong because they’ve been taught to use it like email: send messages, drop links, and ask for time. But that’s not what buyers want.

Here’s what’s broken:

-Connect and pitch behavior ruins trust before it has a chance to grow.
-Generic content gets ignored. Buyers don’t want inspiration. They want insight.
-Resume-style profiles position you as a job seeker—not a resource.
-And AI used without strategy just scales the same ineffective tactics faster.

The key? Train AI to sound like you. Align your profile and content with what your buyer actually cares about. And make your outreach feel like a conversation, not a cold call.

Quick Win: Take your last outreach message and run it through ChatGPT. Use this prompt: “Rewrite this message to sound like someone offering genuine insight, not someone asking for a meeting.”

You’ll immediately feel the difference. So will your prospects.

Transforming Your Profile from Resume to Resource

Your profile is not your resume. It’s your storefront. Your credibility signal. Your conversation starter.

If your profile still reads like a job history, it’s time to change the narrative.

Above the Fold Checklist:

–Headline: Say who you help, how you help, and the results you drive.
-Banner: Visual message that reinforces your expertise and offer.
–Headshot: Approachable. Professional. Direct eye contact.

About Section Framework (5-Part Formula):

–Their Challenge — Open with the problem your buyers face.
–Your Insight — Share a belief or point of view that reframes the problem.
–How You Help — Explain your offer clearly, with outcomes.
–Call to Action — Invite connection or conversation.
–Contact Info — Make it easy to take the next step.

Using the CRISPY™ Prompt Framework to Train AI to Sound Like You

AI won’t write like you unless you train it. That’s where CRISPY comes in:

Context: What’s the goal of the prompt?
Role: Who should the AI act as?
Inspiration: What’s your unique point of view?
Scope: What kind of format or depth do you want?
Prohibitions: What tone or phrases should it avoid?
You: Answer AI’s questions to fine-tune its output.

3 Proven Prompts:

–“Write a connection request that references the buyer’s recent post and starts a natural conversation.”
–“Draft a headline for a profile that positions me as a resource for [target audience].”
–“Write a comment that adds value to a prospect’s post and invites follow-up.”

Social Listening and Thought Leadership That Converts

You don’t need to post every day. You need to be present in the places your buyers already are.

The 10:1 Rule: For every 1 piece of content you post, engage 10x more with your network. Commenting, asking questions, and reacting meaningfully all build familiarity and trust.

When You Don’t Know What to Say:

–Share a post and say: “This challenged how I think about X. I’m curious how are you approaching this?”
–Comment: “This resonates. We see clients facing this exact issue in [industry]. Thanks for sharing it so clearly.”

Turning Your 1st-Degree Network into Sales Conversations

You’re likely connected to hundreds, if not thousands, of people you’ve never had a real conversation with. That’s your biggest missed opportunity.

The CPR Method:

–Clients: Who do you want referrals from or upsell?
-Prospects: Who hasn’t replied, but might with a value-first re-engagement?
–Referral Partners: Who can introduce you to 3+ ideal prospects?

Tactics to Re-Engage:

-Congratulate on a new role.
-Engage with a recent post.
-Send a light-touch reconnect message: “We haven’t caught up in a while—if it makes sense to reconnect, I’d love to explore how we might support each other.”

AI for Pre-Call Planning and Strategic Outreach

You can train ChatGPT to be your pre-call assistant. All you need is the profile, the company site, and a good prompt.

Prompt Example: “Act as my sales prep assistant. I’m meeting with [Name] from [Company]. Here’s their LinkedIn profile and website. Identify who they serve, what problems they solve, and possible points of alignment with our offer.”

What You’ll Learn:

-Their target audience
-Strategic initiatives
-Pain points and language you can mirror

Content + Conversations = Pipeline

Content alone isn’t the goal. Conversations are. But content sparks them—if you do it right.

Three High-Converting Campaigns:

–Poll: Ask a simple, relevant question. Use responses to spark follow-ups.
–Curated Article: Share and say, “This made me rethink [problem]. Curious what you think.”
–Mini Interview: Ask a few experts one smart question. Publish the roundup. Tag them.

The Ask-Offer Ratio and Earning the Right to the Call

If you’re always asking for something (a meeting, a call, a reply), your message gets tuned out. Instead, offer something meaningful first.

High Offer-to-Ask Ratio Examples:

-DM a relevant template or checklist before ever asking for time.
-Share feedback or insight that’s useful with no strings.
-Then say, “If it makes sense to explore this further, happy to hop on a quick call.”

Putting It All Together (and Where to Go Next)

What you’ve built so far:

-A profile that positions you as a resource.
-AI prompts that sound like you.
-Content that earns attention.
-Messaging that feels natural.
-Outreach that respects time and adds value.

Now the key is consistency. Build routines. Systemize your engagement. Batch your content. And always, always lead with value. You don’t need to sell harder. You need to show up smarter.

Author: Brynne Tillman (assisted by askSSL.ai)

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