Open LinkedIn right now. Everyone's talking about content. Hooks. Formats. Carousel templates. Algorithm change of the week.

Nobody talks about DMs.

That's a problem if you're a solopreneur or business owner using LinkedIn for pipeline. Because there's a pattern that breaks the funnel in two places, and most people don't notice the break until they've been posting for a year and wondering why nothing happens.

Here's the pattern.

Most founders skip the diagnostic step. In their posts, they lead with their offer instead of the problem they solve. In their DMs, they open with a polite question that earns a polite non-answer. Same disease, two surfaces. Both skip the part where they make the other person feel seen before they ask for anything.

I fix this on the content side. And so I invited my friend and LinkedIn coach Sara Royf on the podcast who fixes it on the DM side.

(This is the work I'm doing on the podcast now, by the way. Bringing in the people who deeply understand the surfaces related to LinkedIn growth that I don't so that we can teach the whole game instead of just the content half.)

Here’s the number that explains why this matters more than any individual content tip.

One of Sara's clients came to her with 8,000 LinkedIn connections, posted every single day, and had zero clients. (Yes, really. Zero.) She cut his network in half, reworked his profile, and two weeks later he booked six sales calls.

Six. Two weeks. Same person, smaller audience.

I see the mirror version in my work all the time. A founder hires me because they've been posting consistently for a year and nothing's happening. We look at the posts. They're publishing decent stuff. But every post leads with "here's what I do" or "here's my service." Pitching. Not diagnosing. The reader scrolls past because they don't feel seen. They feel sold to.

Same. Exact. Pattern. Two different surfaces.

On the content side, here's the rule I run with every client.

You don't get to talk about your product until you've earned the reader's permission. The way you earn it is by diagnosing the thing they're already feeling but haven't named yet.

This is encoded in the pillar mix I use with every client: 50% problem posts, 30% playbook posts, 20% proof posts. The proof posts (the client wins, the case study, the offer) only land because the problem posts earned them. Skip the problem, and your proof reads like advertising. EVERY time.

PROBLEM POSTS ████████████████████████████ 50%
PLAYBOOK POSTS ███████████████ 30%
PROOF POSTS ██████████ 20%

Quick receipt. A founder I work with had zero LinkedIn presence when we started. Not low. Zero. Five months later, his posts have done 276K views, reaching exactly the people he wants to be known by. Did one of those posts directly book him a call? No. That's not what content does. What content does is build the recognition so that when his name shows up in someone's inbox, the warm-up has already happened.

That recognition is what DMs convert. And that's where Sara comes in.

Sara calls the DM version the Happy Question Trap.

A happy question generates a happy response. Ask someone "what's the best part of your business right now?" and they'll tell you something genuinely lovely. They're working with founders they admire. They're building something meaningful. They feel lucky.

You will learn absolutely nothing.

Polite questions feel like good networking. They produce no signal. You learn that the person is fine. You cannot help "fine."

The fix is structural, not stylistic. You're giving the other person permission to admit something is hard. Most people, given that permission, will take it.

Stop asking happy questions. Start asking neutral or negative ones.

❌ Drop "how's business going?"

→ Try "how have things been going lately?" The word lately alone changes the answer. It gives them room to mention the project that's been frustrating, the client that's been slow to sign, the launch that didn't land.

❌ Drop "what's the coolest thing you're working on?"

→ Try "I saw you posted about [X]. How's that actually playing out?" The word actually does a lot of work. It signals you're not asking for the press-release version.

❌ Drop "how's your business?"

→ Try "I remember you were navigating [a transition / a hiring decision / a launch]. How has that been going?" Specificity questions feel safer to answer. People will tell you the truth about a specific thing when they can't tell you the truth about "their business."

Then root every message in real context.

You're not allowed to send a DM that could be sent to anyone. (That's the actual rule.) If the message doesn't reference something specific the person posted, said, or is visibly working on, it goes in the bin.

Then run an actual cadence.

Sara's framework is two posts a week and ten outreach messages a week. The ten don't have to be cold. Congratulating someone on an award counts. Replying to a thread they started counts. Emails count.

She told me about a client of hers named Shana. A consultant who'd been in business years without ever using LinkedIn for outreach. Two weeks into Sara's program, Shana sent one message to an accounting firm owner she'd been in touch with for years. Used a script, customized it, and started a real conversation. Buying signals showed up by the third message. Got him on a call the next day. Closed an $8,000 contract by year-end.

One DM. To someone she already knew. The bottleneck wasn't audience size. It was that she'd never asked.

The objection I get every time I bring this up is "won't this feel salesy?"

The architecture is the answer. You aren't pitching in the DMs. You're getting to know someone. The pitch only happens after they share a problem you can solve, and at that point, offering to help is the kind thing to do, not the pushy thing.

Sara was direct about this on the podcast: "We're not trying to pitch your services. We're trying to get to know the person. When we get to know the person, we create the opportunity to pitch."

The other objection is time. "I don't have ten DMs a week in me." Ninety seconds per message, ten times a week, is fifteen minutes. You have fifteen minutes. (You spent more than that scrolling LinkedIn while reading this newsletter. Be honest.)

Two things to try this week. They take ten minutes total.

Pull up your last five outgoing DMs. How many were happy questions?

Pull up your last five posts. How many opened with your pitch instead of the problem your product/service solves?

If most of them did either, that's where the funnel is breaking. Either half is fixable in an afternoon. Both halves together is a system.

Reply and tell me what you find. I'll read every one.

-Christine

P.S. Catch Marketers Do Coffee on: YouTube | Spotify | Apple Podcasts

You can learn more about my work at Orchard Strategy.