Avoiding Common Business Messaging Mistakes

Look, cold call pick-up rates and landing in spam are NOT the reasons why outbound isn't working for you in 2025. How do I know? We've worked with thousands of reps in the last few years: - I see all the sh*tty emails - Hardly any reps leave voicemails - People are afraid to call cell phones - Leaders are afraid to set call activity targets - Product pitching like crazy So why isn't outbound working for you? Messaging. I know. Messaging isn't a sexy topic. But poor messaging is likely why outbound doesn't work for you. Common messaging mistakes: ⛔️ Creating outbound messaging in a silo Mistake: A lone BDR leader, sales exec, or marketing exec creates all the cold call talk tracks and email sequences by themselves. Impact: Messaging sounds generic and has too much personal bias. ⛔️ Marketing or product creating outbound messaging Mistake: A PMM or marketing leader writes all the outbound messaging Impact: Since they've had little (or zero) conversations with real customers, the messaging is super generic ⛔️ Product voice: feature heavy messaging Mistake: Messaging focuses on how the solution works, specific features, etc. Impact: This might work on a webpage, but not in a cold email. Messaging feels super salesy and isn't appealing to execs. ⛔️ Not "chunking up" to business outcomes Mistake: Messaging addresses all of the pains of the user, not the decision-makers Impact: Reps get delegated down to product users and struggle to start sales conversations at the exec level ⛔️ Not leveraging customer conversations Mistake: Not using recorded customer conversations to inform messaging Impact: Messaging doesn't use the customer's language and feels generic. What to do instead: ✅ Build a messaging team Get no more than 10 of the best people together to build common messaging. This should include a few of the best AEs, marketing, customer success, sales leaders, product specialists, etc. And make sure to assign a single person to own messaging. ✅ Live workshop messaging by persona/vertical Run live workshops to work out messaging together. At a minimum, messaging should be created for each specific persona. For enterprise, messaging should be created by persona AND industry. A healthcare security leader speaks a different language than a SaaS security leader. ✅ Build a messaging matrix This is what the end product should look like: Personas → Priorities → Current Solutions → Problems/Impact → Desired Outcomes Now you have something that can easily be repurposed into talk tracks and emails. ~~~ If 2025 H1 pipeline looks thin—and outbound isn't producing results—get back to the basics and start with great messaging. Marketing should NOT own sales messaging. Sales needs to own sales messaging. And everyone needs to collaborate together for great messaging. Agree or disagree? 

I received this message from an individual repping AI consulting to help companies drive pipeline. It’s wrong for a variety of reasons… “I am interested to explore if we can work together. I’d be happy to grab a virtual cup of coffee or just chat. Always happy to network either way, let’s chat at your convenience.” Nice? Sure. Clear? Not even close. Effective? Nope. Here’s the problem: “Interested to explore if we can work together” — This is vague and passive. What kind of work? Why me? Why now? I share enough content and talk on enough podcasts you should have better research. “Grab a virtual cup of coffee or just chat” — This is the cold outreach version of “wanna hang out sometime?” If you’re selling AI strategy, lead with something more intentional. “Happy to network either way” — This is filler. And worse, it sounds like you’re just collecting connections. If you’re in the AI space (especially consulting) you have to assume you’re not the only person in my inbox pitching “exploration.” Differentiate or be ignored. Especially if I believe I can use AI to write a better email. How to fix it: ✅ Be specific about why you’re reaching out ✅ Show that you’ve done your homework ✅ Lead with value, not vagueness ✅ Make the ask clear and easy to say yes to Example: “Hey Kyle - I’ve been following how you’re structuring your marketing team around AI. I work with companies like X and Y to automate content workflows and reduce campaign time by 40%. Would you be open to a quick chat next week to swap notes?” Short. Personal. Clear. Relevant. If you’re not sending messages like that, you’re just adding noise. And nobody has time for more noise. Nobody.

🎨🖊️ "Draw two circles under a rectangle…" "Now, make the circles connect to the rectangle" - some of the instructions that were given to me by our Head of Architecture during a recent offsite. We engaged in an exercise that underscored the importance of clear and effective communication. Each participant paired up, with one partner facing a screen displaying an image and the other facing a blank wall with a pen and paper. The challenge? The partner facing the screen had to guide their teammate in drawing the image using only directional and descriptive language. This exercise was a powerful reminder of how crucial it is to be clear, descriptive and thoughtful when sharing requirements, feedback or instructions. In the world of technology, we often fall into the trap of using complex language, acronyms, and omitting details we assume are "obvious." This can lead to confusion, misunderstandings, rework, and ultimately, wasted time. The key takeaway? Being specific doesn't always mean being overly detailed or long-winded. There's a beautiful balance between being specific and descriptive. It's about conveying the right amount of information in a way that's easily understood. Here are some common pitfalls to avoid when striving for specificity in communication: - Overloading with Details: Focus on the most relevant information to avoid overwhelming your audience. - Using Jargon and Acronyms: Consider your audience and provide explanations when necessary. - Assuming Shared Knowledge: Provide necessary context to ensure understanding. - Being Vague: Use precise language to prevent misunderstandings. - Neglecting the Audience's Perspective: Tailor your communication to the needs and understanding of your audience. I am reminded of a quote by Mark Twain: "I apologize for such a long letter - I didn't have time to write a short one." Concise communication takes time and effort, but it's always worth it. In our fast-paced world, mastering the art of effective communication is essential. It not only enhances collaboration but also drives efficiency and innovation. #Communication #Leadership #EffectiveCommunication

Keeping your messaging simple is crucial, because messaging resembles a game of telephone. It's not really about what you said to Joe, but rather about how Joe retransmits that message internally. The more complex and nuanced your message, the lower the fidelity during retransmission. Conversely, a simpler and clearer message ensures higher fidelity. This principle applies to various contexts: - Product messaging through sales into customer champions, their decision makers, and ultimately into their whole organization. - Strategic partnerships, where corporate development teams communicate your words to business leaders. - Financing meetings, where VC investors will retransmit your messaging to the firm's partners and investment committee. - Even internal meetings where questions like "so, what did sales think of the proposal?" will be answered with statements that will be retransmitted with in the executive staff. Building all messaging with this second-order approach in mind is essential. It helps you avoid the temptation to create overly complex or nuanced messages. As the old expression goes, keep it simple, stupid (KISS). Or more amicably, keep it short and simple. Why? Not primarily because you will be better understood by your receiver, but more importantly because they will retransmit your message with higher fidelity. It's all about the retransmission.

Companies don’t fail because their product is bad. They fail because their messaging is unclear. So every marketing dollar underperforms. You feel it long before you see it in the numbers: • Rising CAC • Lead quality dropping • Teams working harder without producing more • Campaigns that “should work”… don’t That’s not an execution problem. It’s a messaging problem. And it quietly drains budgets every single day. I learned this across the two agencies I've built. (And the one I'm building now.) Every time growth stalled, it was the same root issue: We were speaking clearly to ourselves, but not to the market. Recently, a B2B tech client came to me after burning through $42K in paid spend  without generating a single sales conversation. Within 90 days of correcting their messaging, their: • CPL dropped 53% • Sales cycle shortened from 74 to 29 days • Pipeline grew 2.5X Another founder-led company doubled inbound opportunities. Not by increasing budget,  But by clarifying what the problems they were solving. Same marketing channels. New narrative. Different outcome. Here’s the philosophy that consistently stops the waste: 1. Fix the message before you fix the marketing. If people don’t understand what you offer, no tactic can save you. 2. Align every channel to a single narrative. When your website says one thing, your ads say another,  and your sales deck says a third. Buyers disconnect. 3. Turn messaging into a decision-making system. A message isn’t a tagline. It’s a filter that guides every campaign,  every conversation,  every piece of content. This is why clients stop losing money so quickly. We remove guesswork. We replace it with clarity. And clarity compounds. If your marketing isn't working, no amount of ad spend, content volume, or internal meetings  will fix misaligned messaging. You don’t need more tactics. You need a partner whose process starts with clarity... and stays anchored to it. That’s Right Angle. If you want to know whether messaging is the real bottleneck, start with the Clarity Checklist. It’s the diagnostic we use at the start of every engagement to uncover where money is being wasted  and where momentum is hiding. (Link in comments.) B Randall Willis Right Angle

I can learn more about your brand from three of your emails than from your entire marketing portfolio. And for most companies, that’s not a compliment. Before you get fancy, get good. Too many brands skip the unsexy basics so they can chase the shiny thing. Right now, AI is Exhibit A — being bolted onto processes that are presently broken and calling it innovation. Let’s talk about one of my biggest pet peeves: email. I’ve worked with thousands of companies. I’ve read the emails from their call centers, sales teams, executives, even those auto-generated out-of-office replies. I’ve reviewed customer service exchanges word for word during audits. And yes, I judge them all. What do they usually have in common? Sloppy writing. Off-brand tone. Poor syntax. Abrupt phrasing that comes off as unintentionally rude. Lacking Manners. Here’s the truth: Every single message you send is an ambassador of your brand. It telegraphs your standards, your personality, and the care you provide. It sparks a split-second judgment in the reader: Are you capable? Are you respectful? Do I matter to you? That moment happens millions of times a day, and most brands fail it without even realizing. Think it doesn’t matter? Think again: in hundreds of customer focus groups, the topic of communication is raised every time - every customer is critiquing every email they receive. I have a checklist for great communication, and it applies everywhere: email, text, chatbot scripts, even the AI agents you’re training. Today, look at every email your company sends. Are they polished, timely, personalized, brand-consistent in vocabulary and tone? Do they exhibit manners? If not, no tech upgrade will fix the impression you’re creating. From my ERP and CRM implementation days, I’ll leave you with this: Garbage In, Garbage Out. Get exceptional at the basics before you layer anything on top. Whether you have ten employees or 100,000 employees, consistent execution of your standards really matters. #customerexperience #employeeexperience

Your emails say more about you than you think. 👇 Here’s how to make every email polished and professional. Acknowledge Delays Gracefully ✘ "Sorry for the late response." ✔ "Thank you for your patience." Be Clear with Requests ✘ "Let me know what works for you." ✔ "Could you confirm if this works for you?" Own Your Mistakes ✘ "Sorry, I missed that." ✔ "Thanks for pointing that out—I’ll fix it right away." Close Emails Effectively ✘ "Let me know if you need anything." ✔ "Feel free to reach out if you have any questions." Make Follow-Ups Professional ✘ "Just following up on this." ✔ "When can I expect an update on this?" Show Respect for Their Time ✘ "Can we talk about this soon?" ✔ "Would you have 15 minutes this week to discuss this?" Be Confident, Not Tentative ✘ "I think we should consider…" ✔ "Here’s what I propose we do." Avoid Wordy Explanations ✘ "I spent a lot of time rewriting this to make it perfect." ✔ "This email outlines the key points—we can discuss more in person." Offer Solutions, Not Problems ✘ "I’m not sure what to do here." ✔ "Here’s what I suggest as the next step—what are your thoughts?" Set Clear Expectations ✘ "Does this make sense?" ✔ "Let me know if this aligns with your expectations." Be Polite When Asking for Help ✘ "I need this ASAP." ✔ "Would you be able to assist me with this by [specific deadline]?" Keep It Professional When Scheduling ✘ "What time works for you?" ✔ "Are you available at [specific time and date]? If not, let me know what works instead." Emails reflect your professionalism. Get them right, and you’ll always leave a great impression. ➞ Start today by refining your communication style. -- Think this could help someone? Share it to improve the way they communicate. ♻️

Excellent tips here illustrating how a subtle change in tone can have a massive influence upon how your message is received. 1) Acknowledge Delays with Gratitude "Sorry for the late reply…" "Thank you for your patience." 2) Respond Thoughtfully, Not Reactively "This is wrong." "I see your point. Have you considered [trying alternative]?" "Thank you for sharing this—I appreciate your insights." 3) Use Subject Lines That Get to the Point "Update" "Project X: Status Update & Next Steps" 4) Set the Tone with Your First Line "Hey, quick question…" "Hi [Name], I appreciate you. I wanted to ask about…" 5) Show Appreciation, Not Acknowledgment "Noted." "Thank you for sharing this—I appreciate your insights." 6) Frame Feedback Positively "This isn’t good enough." "This is a great start. Let’s refine [specific area] further." 7) Lead with Confidence "Maybe you could take a look…" "We need [specific task] completed by [specific date]." 8) Clarify Priorities Instead of Overloading "We need to do this ASAP!" "Let’s prioritize [specific task] first to meet our deadline." 9) Make Requests Easy to Process "Can you take a look at this?" "Can you review this and share your feedback by [date]?" 10) Be Clear About Next Steps "Let’s figure it out later." "Next steps: I’ll handle X, and you confirm Y by [deadline]." 11) Follow Up with Purpose, Not Pressure "Just checking in again!" "I wanted to follow up on this. Do you need any additional details from me?" 12) Avoid Passive-Aggressive Language "As I mentioned before…" "Just bringing this back in case it got missed."

Some everyday phrases can do real damage. Start speaking like the expert you are. How we speak to clients either builds trust or weakens it before we’ve had a chance to help. I've made the mistake of saying the wrong thing before. Some of it was leftover habits from corporate. Some of it was insecurity I hadn't fully shaken off. But I learned that either way, it was fixable. If you've ever self-edited when talking to a client, this post is for you. Here are the phrases you ought to avoid, and what to say instead: Instead of: “I think this might work…” Say: “Here’s what I recommend based on similar situations.” Instead of: “Just my two cents…” Say: “From my experience, here’s what I’d suggest.” Instead of: “Let me know what you’d like me to do.” Say: “Here’s the next step I suggest we take.” Instead of: “I’m probably wrong, but…” Say: “This may challenge the current approach, but it’s worth considering.” Instead of: “This might be a dumb question, but…” Say: “I have a clarifying question.” Instead of: “Sorry if this doesn’t make sense.” Say: “Let me know if I should explain that differently.” Instead of: “That’s not really my area.” Say: “That’s outside my scope, but I can recommend someone who handles that.” Instead of: “Hopefully this works.” Say: “Let’s test this and adjust as needed.” Instead of: “I’m just a solo consultant.” Say: “You’ll be working directly with me. No delays or middlemen.” Instead of: “Everyone’s doing it this way.” Say: “That’s the common approach, but let’s decide what fits your situation best.” The right language positions you as a guide, not just another vendor. If your messaging already feels solid but you're not sure where the gaps are, I built a quiz that can help. It shows you your consulting archetype, biggest blind spot,  and gives you a roadmap for your next growth stage. Take it for free here: https://lnkd.in/gve8CjUu 📨 If you're ready to book a call, send me a DM with the word "ready." ♻️ Repost this to help out your network. ➕ Follow Dale Gibbons to turn your genius into a 7-figure consulting business.

"Our product is better, but customers aren't buying." The problem isn't your product—it's your messaging. After analyzing 1,000+ companies, I've discovered most have products that address unmet customer needs but fail to communicate those advantages. The 4 messaging mistakes killing your growth: 1. Feature-first messaging - Talking about your features instead of outcomes 2. Generic value propositions - Using the same tired phrases as every competitor 3. Solution-focused - Describing your technology instead of customer outcomes 4. Assumption-based positioning - Guessing what matters instead of knowing The solution: Outcome-driven messaging that directly connects your product strengths to underserved customer outcomes. Coloplast discovered their wound care customers weren't primarily concerned with "faster healing"—they wanted to "prevent complications." One messaging shift drove them from stagnant growth to double-digit growth in 6 months. What un-messaged strengths are hiding in your current offerings?