You now have a story bank, a structure for telling stories well, and techniques for pulling new stories out of your experience on an ongoing basis. The remaining question is the one that determines whether any of this generates business: which stories should you tell, and in what order?
Know Exactly Who You Are Writing For
Before you decide which stories to tell, you need a clear picture of the person you want reading them. Answer these questions about your ideal reader:
- What is their title and what does their day look like?
- What is the decision they are trying to make right now that your product or service is relevant to?
- What have they tried before that did not work?
- What do they believe about your space that might be wrong or incomplete?
- Where are they in the buying process: unaware they have a problem, aware but not looking, looking but not ready, or ready but comparing options?
- What would make them stop scrolling and think "this person understands my situation"?
The last question matters the most. Every story you tell should make your ideal reader feel like you are describing their world from the inside. If your stories consistently do that, the right people will pay attention. If your stories are broad enough that anyone could relate to them, nobody will feel specifically spoken to.
Expert Tip: Pick one reader profile and write for them. If you serve multiple segments (say, engineering leaders and go-to-market leaders), alternate between them across posts. But within a single post, every detail, every example, and every framing choice should be aimed at one specific person.
How Different Story Types Attract Different Readers
The five story categories from Chapter 1 (origin, operational, client, industry, failure) do not all serve the same pipeline function. Each one attracts a slightly different reader and builds a different kind of trust.
| Story category | Who it attracts | What it builds | Where it fits in the pipeline |
|---|---|---|---|
| Origin and identity | People who are curious about you as a person. Early-stage followers. Potential referral partners. | Relatability and trust. Gives people a reason to care about your perspective before they evaluate your expertise. | Top of funnel. Gets people following you and paying attention. |
| Operational and decision | People who run teams or companies and are navigating similar challenges. Mid-funnel prospects who are evaluating whether you think the way they do. | Competence and depth. Shows you have thought carefully about the same problems they face. | Mid-funnel. Builds confidence that you understand their world. |
| Client and customer | People who are wondering what it is like to work with you or use your product. Late-funnel prospects comparing options. | Credibility and proof. Shows you have done this before and can describe the results. | Bottom of funnel. Moves people from "interested" to "ready to talk." |
| Industry and market | People who want to stay informed about their space. Peers, potential partners, and prospects who are not yet problem-aware. | Authority and positioning. Shows you see things others in your market do not. | Top to mid-funnel. Attracts people through your thinking, not your product. |
| Failure and mistake | People who are skeptical of polished personal brands. Experienced operators who have been burned before and value honesty. | Trust and differentiation. An executive willing to describe what went wrong stands out from the ones who only post wins. | Works across the funnel. Accelerates trust at every stage. |
- Not enough people know who you are → Lean into origin and industry stories. They cast a wide net and give people a reason to follow.
- People follow you but never reach out → Lean into operational and client stories. You have attention but you have not built enough confidence or proof to move people toward a conversation.
- Prospects get to the sales call but do not convert → Lean into client and failure stories. Prospects who have already seen detailed accounts of how you work and what you have learned from getting it wrong arrive at the call with a higher baseline of trust.
3 Questions to Ask Before Developing a Story
Before developing a story from your bank into a post, run it through these filters:
"Would my ideal reader see themselves in this?"
The story does not need to be about your reader's exact situation. But it needs to describe a tension, a problem, or a decision that your reader has faced or is facing. A story about losing a client because of slow response time resonates with any founder managing a service business. A story about restructuring your pricing after a competitor undercut you resonates with any operator who has dealt with pricing pressure. The reader should finish the post thinking "I have been in a version of that situation."
If the story is interesting but your ICP would read it and think "cool, but that does not apply to me," save it. It might work as a personal-brand post later, but it is not a pipeline post.
"What would this make someone want to do next?"
A well-targeted story should create a natural next action for the reader. Not a call-to-action you bolt onto the end of the post, but an organic impulse. The reader finishes the post and thinks:
- "I want to learn more about how this person's company handles X" (visits your profile, follows you)
- "I have the same problem and I want to know if they can help me" (sends a DM, books a call)
- "I should send this to my co-founder because we are dealing with the same thing" (shares the post, expanding your reach to a warm network)
If you cannot identify what a reasonable ICP reader would want to do after reading the story, the story might be well-written but poorly targeted.
"Does this story qualify or disqualify?"
The best pipeline content does both. It attracts the people you want to work with and signals to the people you do not want to work with that they are not a fit.
A story about firing a client because they refused to give feedback does two things at once: it attracts executives who value collaboration and it tells passive, disengaged prospects that your working style requires involvement. A story about turning down a request to produce low-quality content at high volume attracts people who care about quality and repels people looking for the cheapest option.
This filtering effect is a feature. Every post that repels a bad-fit prospect saves you a sales call that was never going to convert.
Sequencing Stories Over Time
The sequence in which you tell stories over weeks and months matters because your audience is not reading a single post in isolation. They are building a cumulative picture of who you are, what you know, and whether they trust you.
Introductory Sequence (First 4-8 Weeks of Posting)
If you are new to LinkedIn or restarting after a break, your first several weeks of content should answer three questions for any new follower:
- Who is this person and why should I care? (Origin stories, identity stories)
- Do they know what they are talking about? (Operational stories, industry observations)
- Can I trust them? (Failure stories, honest takes on mistakes)
A new follower who visits your profile and scrolls through your recent posts should be able to answer all three within a few minutes. If your first 8 posts are all industry commentary, they know your opinions but they do not know you. If your first 8 posts are all personal stories, they like you but they do not know whether you are competent. The mix makes a difference.
Ongoing Rotation
After the introductory phase, think about your content in cycles. Over the course of a month, your posts should touch multiple story categories and multiple stages of the pipeline.
A rough framework for a month of content (assuming 3-4 posts per week):
| Week | Mix |
|---|---|
| Week 1 | 1 operational story (shows competence) + 1 industry take (shows awareness) + 1 personal story (builds connection) |
| Week 2 | 1 client story (builds proof) + 1 failure story (builds trust) + 1 framework post drawn from operational experience |
| Week 3 | 1 industry take + 1 operational story + 1 personal story |
| Week 4 | 1 client story + 1 opinion or contrarian take + 1 framework post |
This is a starting point. The principle: do not let any one category dominate for multiple weeks in a row. Your audience should see range, because it signals that you are a whole person with depth.
Expert Tip: After 8-12 weeks of posting, you will have data on which story categories generate the engagement that matters to your business. Not likes and impressions (those are vanity metrics) but profile visits from ICP prospects, DM conversations with potential buyers, and mentions in sales calls ("I saw your post about X").
When you notice a pattern, lean into it. If your operational stories consistently generate DM conversations from your ICP but your industry takes generate engagement from peers who will never buy, shift the ratio. Post more operational stories. Do not stop posting industry content entirely (it serves a different function), but weight your calendar toward the category that is producing pipeline.
Connecting Content to Conversations
The final piece is closing the loop between a story you publish and a conversation that leads to business.
Tracking What Works
For every story you publish, track two things:
- Who engaged: Look at the profiles of the people who commented, liked, or shared. Are they in your ICP? Are they adjacent? Are they irrelevant?
- What happened next: Did anyone DM you? Did anyone book a call? Did a prospect mention the post in a meeting? Did someone forward it to a colleague who then reached out?
A simple log that connects posts to outcomes is enough to keep track:
| Post (date + topic) | ICP engagement (Y/N) | DMs or conversations generated | Notes |
|---|---|---|---|
| 6/12, story about firing an unresponsive client | Y, 3 ICP commenters | 1 DM from a Series B founder asking about our onboarding process | DM turned into a call on 6/18 |
| 6/15, industry take on pricing trends | N, mostly peer engagement | None | Good for brand, not for pipeline |
| 6/19, operational story about our hiring process | Y, 2 ICP commenters | 2 DMs, one asking for the full framework | Shared framework, both booked calls |
Over 90 days, this log tells you everything you need to know about which stories are moving your pipeline and which are building your brand without producing business. Both have value. But if you are allocating limited time to content, the posts that produce pipeline should get priority.
Feedback Loop
The tracking log feeds directly back into your story selection. Stories that generated ICP engagement and conversations should inform future content. Not by repeating the same story, but by writing more stories from the same category, about similar topics, with similar levels of specificity.
If your post about firing an unresponsive client generated three ICP DMs, that tells you your audience cares about client management, boundaries, and service quality. Write more stories from that part of your experience. A story about how you onboard clients. A story about how you handle scope creep. A story about the difference between a client who collaborates well and one who does not. The first post that performed tells you what vein to mine next.
Content that is aimed well compounds. Content that is aimed randomly does not, regardless of how well it is written.