From Polite Hellos to Whispered Deals

🔍 You don’t need a big audience — you need better conversations.

✉️ Start with a real message, not a pitch or a link.

🧠 Write blog posts after someone asks for your thoughts — not before.

🗣 Whispering builds trust faster than shouting into the void.

📈 Selling starts when you sound like yourself, not someone else.

So, you’re a veteran SAP consultant branching out on your own. You can debug a complex workflow in your sleep and charm the toughest clients once they hire you. But there’s a catch: now you have to find those clients. That means putting yourself out there — DMs, cold outreach, self-promotion. If that thought makes your stomach do a little flip, you’re not alone. Fear of rejection, the awkwardness of sliding into someone’s inbox, and the temptation to retreat to writing yet another blog post (that nobody asked for) are all too common.

This article is a conversation between two characters: Isard, a SAP guru turned aspiring entrepreneur, and Wiz, an AI mentor with a dry sense of humor and a love for metaphors. It’s a candid, witty back-and-forth about tackling direct messaging (DM) strategies when you’re allergic to anything that smells like sales. We’ll explore three DM approaches — from ultra-polite to bold-as-brass to a new “whisper” method — and figure out what fits a consultant who’d rather solve a client’s SAP issue than sell them on it.

Ready to eavesdrop on Isard and Wiz’s chat? Let’s dive in.

Strategy 1: Graham’s Polite, Low-Risk Outreach

Isard: (grimacing at his screen) I just got a new LinkedIn connection. I know I should probably reach out… but I have no clue what to say that doesn’t feel awkward or salesy.

Wiz: Ah, the classic polite paralysis. You know, the “I hope you’re well, I just wanted to connect and maybe possibly sort of help you if you don’t mind” approach.

Isard: Hey, that sounds like my buddy Graham’s style. He always sends these polite DMs thanking people for connecting. Low risk, sure… but I don’t think he’s ever gotten a client out of it.

Wiz: Exactly. Let’s talk about Graham’s polite, low-risk outreach. It’s like a timid handshake in DM form. Friendly, zero pressure. Also zero urgency.

Isard: Right. Graham usually writes something like:

Example DM (Graham’s style): “Hi [Name], thanks for connecting! I noticed you work with SAP at [Company]. That’s awesome. Let me know if I can ever help with anything. Have a great day!”

Wiz: (raises an eyebrow) Which is perfectly polite. Non-threatening. And easy to ignore.

Isard: Ouch. But true. People say “thanks” or just ghost him. It’s so low pressure there’s no reason to respond.

Wiz: The strength of this approach is it won’t get you labeled a spammer. It’s courteous and keeps doors open. The weakness? It often leads to the friend zone of business. Prospects don’t feel any compelling reason to continue the chat.

Isard: It’s almost like I’m saying “I’m here if you need me,” and they’re saying “Cool, I’ll call if I need open-heart surgery on my ERP system.”

Wiz: Precisely. Polite outreach like Graham’s is comfortable. Safe. But if you stop there, you’re basically writing content no one asked for – or in this case, offering help no one feels they need at that moment.

Isard: So what’s the takeaway here?

• Low Risk = Low Reward: A gentle DM won’t ruffle feathers, but it may not grab attention either.
• Builds Goodwill: It at least sets a friendly tone and shows you’re approachable.
• Needs Follow-Up: If you start polite, be ready to nurture the conversation further; don’t expect the prospect to drive it.

Strategy 2: Wayne’s Bold, Direct DM Pitch

Isard: Alright, what about the other extreme? I’ve seen folks who just dive in and pitch on first hello. Like that guy Wayne from “The DM Edge” you told me about.

Wiz: Ah yes, Wayne’s bold, direct DM sales approach. If Graham’s DM is a gentle tap on the shoulder, Wayne’s is more like a confident clap on the back – maybe a tad hard.

Isard: Wayne’s the one closing deals in DMs left and right, no sales calls, right?

Wiz: (nods) He’s not shy. Wayne might send something like:

Example DM (Wayne’s style): “Hey [Name], I noticed your company’s struggling with SAP rollouts. I help businesses fix those issues fast. I’ve helped companies save six figures in downtime. Interested in chatting details? 👍”

Isard: (whistles quietly) Bold. He’s basically saying “I see your problem, I have the solution, you in?”

Wiz: Exactly. No fluff, no long buildup. Strength? It quickly identifies who’s interested. If they bite, they bite fast, and you’re on the road to a deal. Weakness? It can feel impersonal or pushy. You will turn off people who aren’t ready for that level of directness.

Isard: I’d be afraid of coming off as a pushy salesperson. The kind that makes people hit “Block” or report spam.

Wiz: True, Wayne’s method is a bit of a high-wire act. Done poorly, it’s the DM equivalent of a cold call during dinner. But done well — with research and targeting — it can be effective. Wayne would say it’s about quality conversations over quantity: he targets a small group of ideal prospects and goes straight to the point.

Isard: I’m not sure I’m ready to channel my inner Wayne. It’s effective for him, but it feels… not me.

Wiz: And that’s okay. We learn from Wayne that confidence and clarity sell. You don’t have to copy his style exactly, but notice he’s not afraid to state his value. The guy doesn’t whisper; he shouts (in a helpful way).

Isard: Takeaways for the bold approach?

• High Risk, High Reward: Direct DMs can lead to quick wins or quick rejections. You’ll know soon enough.
• Be Clear on Value: You have to know the pain points and hit them head-on. No waffling.
• Thick Skin Required: Some will ignore you or say “no thanks.” You can’t let that crush you.

Strategy 3: The “Whisper Funnel” – Conversation as a Funnel

Isard: So we have polite-as-pie and bold-and-direct. Is there a middle path? Something that doesn’t feel toothless or aggressive?

Wiz: Funny you ask – I was about to suggest we cook up a hybrid. Let’s call it the “Whisper Funnel.”

Isard: Whisper Funnel?

Wiz: Think of it this way: instead of shouting your pitch or just waving hello, you whisper. Start a low-key, genuine conversation. Gradually, with permission, guide it towards a problem you can solve. By the end, the person invites your pitch without you ever really “pitching.”

Isard: Sounds sneaky – in a good way. How would that look in practice?

Wiz: It might start like:

Example DM (Whisper Funnel start): “Hi [Name], saw your post about your SAP migration headaches. Been there. 😅 Curious, what’s been your toughest challenge with it?”

Isard: Okay, so I’m opening with something relevant to them, showing I actually care about their experience.

Wiz: Right. It’s conversational and permission-based. You’re not dumping your solution upfront; you’re inviting them to share. If they reply and open up (best case, they describe a pain you can fix), you keep the conversation going naturally.

Isard: And then at some point I transition to offering help?

Wiz: Exactly. After a few back-and-forth messages, once you’ve built some rapport and they’ve basically handed you a golden problem on a platter, you might say:

Example DM (Whisper Funnel pivot): “Appreciate you sharing that. You know, I’ve actually dealt with that exact issue for another client. If you’re interested, I could shoot you a quick tip or resource that helped them.”

Isard: Nice. You’re asking permission to give them something of value. Who would say no to a helpful tip?

Wiz: Many will gladly say “Sure, tell me more.” Now you have the green light to share a bit of your expertise — maybe a mini solution or insight. This is where you demonstrate your value.

Isard: And I can imagine after I give the tip, I could mention, “Funny enough, I was thinking to write a short article about this common issue.” Maybe even ask if they’d like to see it once it’s done.

Wiz: Bingo. Now you’re turning this DM conversation into inspiration for content — content that at least one person (them) genuinely cares about. You’re literally writing the content somebody asked for. When you do publish that blog or post addressing their problem, you share it with them:

Example DM (Whisper Funnel follow-up): “Hey, I put together that article on solving [Problem]. Your story was front of mind (don’t worry, I kept you anonymous 😇). Here it is — hope it helps others too!”

Isard: This is clever. By now I’ve had multiple friendly exchanges, provided value, and even created a blog post out of it. All without ever feeling like a sleazy salesman.

Wiz: And the beauty is, at this point, they see you as an expert and a helpful human. Maybe they thank you, maybe they ask another question. Maybe they even say, “Can we talk about how you could help us implement this?”

Isard: That would be the dream outcome — they essentially invite me to discuss business.

Wiz: That’s why it’s a “funnel.” It starts with a whisper of a conversation and gently guides them to a place where working with you is the next logical step. Even if they don’t become a client immediately, you’ve got great content and a relationship.

Isard: Let’s break down the Strengths and Weaknesses quickly: it’s personal and value-driven, but it takes more time and active effort. Opportunities: it can yield content and referrals. Threats: maybe the chat fizzles out or I invest time and they never buy… but then again, I can still use what I learned.

Wiz: You’re catching on. In fact, let’s compare all three approaches side by side before we go deeper.

Comparing DM Approaches – A Quick SWOT

(Wiz grabs a virtual napkin to sketch a SWOT analysis)

Aspect	Graham’s Polite Outreach	Wayne’s Bold Pitch	“Whisper Funnel” Approach
Strengths	– Friendly and risk-free introduction- Doesn’t annoy or overwhelm the recipient	– Gets straight to the point, filters interest fast- Can secure quick wins without drawn-out courting	– Builds genuine connection and trust- Uncovers real pain points (market research)- Generates content alongside outreach
Weaknesses	– Easy to ignore or forget- Often doesn’t progress beyond small talk	– Can appear spammy or too aggressive- Rejections can be frequent and blunt	– Takes longer, requires patience- Not as straightforward to scale quickly- Needs good judgment on when to pivot to business
Opportunities	– Nurture into relationships over time- Low-pressure follow-ups (like commenting on their posts) can gradually warm them up	– Quickly identify hot leads ready to buy- Refine pitch with each attempt to improve success rate	– Positions you as a helpful expert, not just a salesperson- Content created can attract similar clients (one conversation -> many readers)- Builds a reputation through word-of-mouth (people remember the help)
Threats	– Might never convert (stuck in perpetual “nice guy” zone)- Competitors might swoop in more decisively while you’re exchanging pleasantries	– Risk of burnt bridges if tone is off- Could harm personal brand if people share screenshots of a bad pitch	– If mishandled, can become a time sink with no sale- Relying on them to eventually invite your pitch – some may never do so

Isard: Seeing it laid out like this, it’s clear each approach has trade-offs. There’s no one-size-fits-all.

Wiz: Exactly. It’s about aligning with your style and your business needs. Now, you identified with Graham’s gentleness but saw how it stalls, and you admire Wayne’s results but not his style. The Whisper Funnel seems to resonate because it plays to your strengths as a consultant: problem-solving and teaching.

Isard: It does. But I’ll be honest, even the Whisper Funnel sounds like actual work. I mean, it’s easier to just keep writing blog posts behind my screen. Talking to real people… that’s stepping out of my comfort zone.

Facing the Fear: From Consultant to Confident Founder

Wiz: Let’s talk about that. This isn’t just about DMs, is it? It’s about fear and identity. You’ve been a tech wizard for years, but as an entrepreneur you also have to be a storyteller, a connector, maybe even a salesperson. That’s a shift.

Isard: (sighs) Yeah. Part of me still feels like that employee who waits for work to be handed down. Now I have to ask for work, to convince people… It feels like I’m putting on someone else’s clothes. Like I’m an imposter in a used car lot, except I’m selling myself.

Wiz: It’s a common fear. The rejection feels personal because you are the product now. But here’s a reframe: You’re not selling, you’re helping. Your expertise solves real problems. Reaching out is offering to help, not trick someone into something.

Isard: I guess I fear the rejection because it feels like they’re rejecting me, not just a service.

Wiz: True, it stings. But every “no” is also a “not now” or “not this way.” It’s not a verdict on your worth or competence. Remember, you’re still that confident SAP expert. Now you’re just inviting more people to benefit from it.

Isard: It’s an identity shift, but maybe I can approach it as an extension of what I already do: diagnosing problems and offering solutions. Just a more social version of it.

Wiz: Exactly. Think of outreach as an extension of consulting. Instead of waiting for a support ticket to land in your queue, you’re proactively looking for broken systems to fix. You’re still the fixer, just finding the broken things yourself.

Isard: When you put it like that, it feels more authentic. Less like I’m begging for business, more like I’m seeking out folks who need a hand.

Wiz: (grins) That’s the spirit. And with the Whisper Funnel, you’re doing it in a very you way – conversational, helpful, and strategic. No screaming into the void, no fake enthusiasm, just real talk.

The Whisper Funnel Game Plan: Actions to Try

Wiz: Alright, now that you’re mentally prepared, let’s get practical. How do you try the Whisper Funnel method? Here’s a simple action plan:

1. Identify 3-5 People to Reach Out To: Pick a few contacts or new connections who fit your ideal client profile and have recently mentioned a relevant challenge (check their posts, comments, or even job roles for clues).
2. Start a Genuine Conversation: Send a friendly DM referencing something specific – a post they made, a common challenge in your field, or a mutual interest. Ask a question to invite their thoughts. (“I saw you mentioned struggling with X… how’s that going for you?”)
3. Listen and Engage: When they reply, truly listen. Ask follow-up questions, share a quick anecdote of your own if relevant, but keep the focus on them. Avoid jumping in with a solution immediately.
4. Spot the Pain Point: As they open up, identify a problem you can help solve. Empathize with it (“I get how tough that is.”) before offering any advice.
5. Offer Value (With Permission): Ask if they’d like a tip, resource, or insight. Example: “I have an idea that might help with that — mind if I share?” When they say yes, give them a concise, useful nugget of advice.
6. Deepen the Connection: Continue the conversation as it feels natural. You might share a short success story (“I saw this with a client last year…”) without turning it into a pitch. Gauge their interest level.
7. Create Content from the Convo: If the problem is juicy enough, write a short article or post about it (genericized, not naming them unless they’re okay with it). Next time you talk, send it their way: “Remember that issue we discussed? I wrote up a piece on how to tackle it.”
8. Expand or Transition: At this point, if they show clear interest in solving this problem with help, invite a next step. This could be as low-key as “Happy to chat more if you ever want to brainstorm solutions,” or as direct as “Think we should hop on a call to dive deeper?” — whichever fits the vibe you’ve got.
9. Repeat Consistently: Do this regularly with new folks. Not every conversation will turn into a client, but you’ll get practice, content ideas, and maybe some referrals along the way.

Isard: This makes it concrete. It doesn’t sound like a factory cold outreach script; it sounds like me actually talking to people.

Wiz: Because it is you talking to people. One genuine conversation at a time. It’s not magic, and it’s not an overnight lottery ticket. But it’s sustainable and authentic.

Isard: I can do this. I will do this. I already have a guy in mind who commented about a messy SAP integration last week. I’ll start there.

Wiz: Perfect. And remember: the goal is to help, not to hard-sell. Whether or not he becomes a client, you’ve started a relationship and you might get a great topic to write about.

Whisper vs. Shout: Doing it Your Own Way

Isard: You know, I expected you to just give me a pep talk to “be more aggressive” or something. Instead, you helped me find a way that suits who I am. I appreciate that, Wiz.

Wiz: (pretends to polish nails on an imaginary lapel) I aim to please. Or at least to be less annoying than a motivational poster.

Isard: (laughs) Mission accomplished. It’s funny: all this talk about whispering, and I actually feel more confident, not less. Like I have permission to be myself and still succeed at this.

Wiz: That’s the sweet spot — doing outreach your way. Some people win by shouting from the rooftops; others, like you, will win by having quiet, meaningful chats that echo later. Whispering sometimes travels further than shouting because the right people lean in to listen.

Isard: Well said. Time to start whispering and see where these conversations take me.

Wiz: Go get ‘em, Isard. You’ve got the knowledge, you’ve got the strategy, and now you’ve got the mindset. Remember, whether you tap, clap, or whisper, the key is you’re reaching out. And that’s how doors open.