Engaging With Decision Makers

𝐖𝐡𝐲 𝐝𝐨 𝐬𝐨𝐦𝐞 𝐩𝐞𝐨𝐩𝐥𝐞 𝐠𝐞𝐭 𝐩𝐫𝐨𝐦𝐨𝐭𝐞𝐝 𝐟𝐚𝐬𝐭𝐞𝐫, 𝐡𝐞𝐚𝐫𝐝 𝐦𝐨𝐫𝐞 𝐨𝐟𝐭𝐞𝐧, 𝐚𝐧𝐝 𝐭𝐫𝐮𝐬𝐭𝐞𝐝 𝐦𝐨𝐫𝐞 𝐝𝐞𝐞𝐩𝐥𝐲? Of all the topics people ask me about, executive presence is near the top of the list. The challenge with executive presence is that it’s hard to define. It’s not a checklist you can tick off. It’s more like taste or intuition. Some people develop it early. Others build it over time. More often, it’s a lack of context, coaching, or exposure to what “good” looks like. Here’s what I’ve learned over the years, both from getting it wrong and from watching others get it right. 1. 𝐋𝐚𝐧𝐝 𝐲𝐨𝐮𝐫 𝐦𝐞𝐬𝐬𝐚𝐠𝐞 People early in their careers often feel the need to prove they know the details. But executive presence isn’t about detail. It’s about clarity. If your message would sound the same to a peer, your manager, and your CEO, you’re not tailoring it enough. Meet your audience where they are. 2. 𝐔𝐩𝐥𝐞𝐯𝐞𝐥 𝐭𝐡𝐞 𝐜𝐨𝐧𝐯𝐞𝐫𝐬𝐚𝐭𝐢𝐨𝐧 Executives care about outcomes, strategy, and alignment. One of my teammates once struggled with this. Brilliant at the work, but too deep in the weeds to communicate its impact. With coaching, she learned to reframe her updates, and her influence grew exponentially. 3. 𝐔𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝 𝐭𝐡𝐞 𝐬𝐮𝐛𝐭𝐞𝐱𝐭 Every meeting has an undercurrent: past dynamics, relationships, history. Navigating this well often requires a trusted guide who can explain what’s going on behind the scenes. 4. 𝐏𝐫𝐨𝐯𝐢𝐝𝐞 𝐜𝐨𝐧𝐭𝐞𝐱𝐭 Just because something is your entire world doesn’t mean others know about it. I’ve had conversations where I assumed someone knew what I was talking about, but they didn't. Context is a gift. Give it freely. 5. 𝐂𝐨𝐦𝐞 𝐰𝐢𝐭𝐡 𝐬𝐨𝐥𝐮𝐭𝐢𝐨𝐧𝐬 Early in my career, I brought problems to my manager. Now, I appreciate the people who bring potential paths forward. It’s not about having the perfect solution. It’s about showing you’re engaged in solving the problem. 6. 𝐊𝐧𝐨𝐰 𝐰𝐡𝐚𝐭 𝐭𝐡𝐞𝐲 𝐜𝐚𝐫𝐞 𝐚𝐛𝐨𝐮𝐭 Every leader is solving a different set of problems. Step into their shoes. Show how your work connects to what’s top of mind for them. This is how you build alignment and earn trust. 7. 𝐁𝐮𝐢𝐥𝐝 𝐜𝐨𝐧𝐧𝐞𝐜𝐭𝐢𝐨𝐧 Years ago, a founder cold emailed me. We didn’t know each other, but we were both Duke alums. That one point of connection turned a cold outreach into a real conversation. 8. 𝐃𝐫𝐢𝐯𝐞 𝐭𝐨 𝐜𝐥𝐚𝐫𝐢𝐭𝐲 𝐚𝐧𝐝 𝐝𝐞𝐜𝐢𝐬𝐢𝐨𝐧 Before you walk into a meeting, ask yourself what outcome you’re trying to drive. Wandering conversations erode credibility. Precision matters. So does preparation. 𝐅𝐢𝐧𝐚𝐥 𝐭𝐡𝐨𝐮𝐠𝐡𝐭 Executive presence isn’t about dominating a room or having all the answers. It’s about clarity, connection, and conviction. And like any muscle, it gets stronger with intentional practice.

A prospect tells you: "We’re also looking at [Competitor]." Most reps make one of two mistakes: - They panic and start discounting before the customer even asks. - They attack the competitor, thinking that will win trust. The best reps? They guide the conversation...without badmouthing or getting defensive. Here’s how we teach folks to do it at Sales Assembly: 1) Find the gap. Instead of “We’re better because…” ask: “What made you start looking in the first place? What’s missing today?” This gets them to focus on their pain, not a feature battle. 2) Understand their criteria. Instead of “Why are you considering them?” ask: “What’s most important to you in a solution?” You want them defining success in your playing field. 3) Focus on fit, not features. Instead of “We’re better at X,” ask: “What’s been standing out to you in each option so far?” If they highlight something critical you do better, that’s your opening. 4) Help them think ahead. Instead of “They don’t do [X] like we do,” say: “A lot of teams in your space have prioritized [X] because it impacts [Y]. How are you thinking about that?” This frames the conversation around outcomes - not a feature war. 5) Guide the decision process. Instead of “Who’s your front-runner?” ask: “What’s your process for narrowing down options?” If they don’t have a clear decision path, they’re likely to stall. 6) Make the decision feel easy. Instead of “How can we win this deal?” ask: “If you had to make a decision today, what would give you confidence?” This surfaces final concerns...so you can remove them. The goal isn’t to beat competitors. It’s to help buyers feel confident that choosing you is the right move.

Most AEs fail on the phone for one simple reason: They’re cold calling people who’ve never heard of them. In 2025, that’s just lazy. Here’s how I would book executive meetings without sounding like a desperate sales rep: I used to teach cold calling techniques. Tonality. Pacing. Objection handling. And while that still matters... It’s not the reason I consistently get meetings with C-level buyers. The secret? I never cold call anymore. I warm call. Here’s how I do it: Step 1: Start with a personalized, relevant email. Do some quick research. Make it about them. For example, if I’m reaching out to a CRO, I’ll highlight a drop in quota attainment from RepVue and explain how I can help upskill their team in tough times. Step 2: That same day—a few hours later—I call their cell phone. (ZoomInfo or LinkedIn can get you that. No excuses.) DO NOT call the office. DO NOT waste time dialing assistants. If you can’t get a cell, send a LinkedIn connection request with a DM or video message. Step 3: When I call, I say: “Hi, this is Ian Koniak—did you happen to see the email I sent this morning?” If they say no: “No problem. I sent it because I saw your team’s quota attainment is down since 2022. I think I can help based on what I’ve done with other clients. Do you have a couple minutes now, or should we find time to connect on Zoom?” It’s not a pitch. It’s a reference to something you already sent that’s about them. That’s what makes it warm. Step 4: If they don’t respond, wait 2–3 days. Then reply to the original thread with more context: – Mention the training or workshops you offer – Share real results (e.g., 20% increase in quota attainment) – Ask: “Is this something you’d be open to learning more about?” Always lead with interest, not a hard ask for time. Step 5+: Stack 6–8 touchpoints total. Each one builds on the last—adding more insight, examples, testimonials. Mix in: – LinkedIn videos – Client stories – Relevant frameworks Each message = more value. That’s how you break through. It can take 8-12 touchpoints to get a meeting. Most reps quit after 1-3 touchpoints. Or worse—just send the same “following up” message. No value. No relevance. No shot. This process works. It’s not magic. It’s just real sales effort with a real strategy.

Tired of hearing that you should personalize cold emails? "You should personalize cold emails" has become "no sh*t Sherlock" advice. The real challenges you're having: ❌ You end up wasting hours going down a “research rabbit hole” ❌ The exec team is worried about activity levels dropping ❌ You don’t know how to connect personalization to the rest of the email ❌ Your personalization attempts haven’t increased reply rates ❌ Your prospects have very little public information available Personalization increases reply rates by 1,200%+ (Lavender 💜) So let's dig into how to "personalize at scale" It’s all about finding patterns. Without these patterns, you’re going to spend hours looking for something that should take 5-10 minutes tops. It’s what our clients are mastering right now to dramatically cut down on research time without sacrificing quality. Start by finding patterns in these three values buckets: ✅ Accomplishments — What does the prospect or company brag about? Examples: Company awards, personal achievements, customer reviews, case studies, testimonials, charity work, podcast interviews, features in publications, etc. ✅ Education — What does the prospect or company educate their prospects and customers about? Examples: White papers, case studies, ebooks, podcasts, webinars, conferences they host, blog posts, LinkedIn articles, etc. ✅ $$$ — What does the company invest in? Examples: mergers, acquisitions, new products/services, funding, new locations, contraction, new countries, hiring, etc. ~~~ Once you find patterns in the 3-5 most common triggers across prospects, use the attached image to find those triggers. You can also reverse-engineer your best meetings and closed/won deals to find patterns in triggers. Then create workflows for them. Write down the exact steps you use to search Google, company websites, LinkedIn profiles, quarterly reports, etc. Over time, you’ll build a process that eliminates most of the busywork. ~~~ Sales leaders—provide bumper guards and guidelines for reps so they know exactly what to look for and where to find it. You'll see amazing results over time when you can streamline this process. #sales

I was Wrong about Influence. Early in my career, I believed influence in a decision-making meeting was the direct outcome of a strong artifact presented and the ensuing discussion. However, with more leadership experience, I have come to realize that while these are important, there is something far more important at play. Influence, for a given decision, largely happens outside of and before decision-making meetings. Here's my 3 step approach you can follow to maximize your influence: (#3 is often missed yet most important) 1. Obsess over Knowing your Audience Why: Understanding your audience in-depth allows you to tailor your communication, approach and positioning. How: ↳ Research their backgrounds, how they think, what their goals are etc. ↳ Attend other meetings where they are present to learn about their priorities, how they think and what questions they ask. Take note of the topics that energize them or cause concern. ↳ Engage with others who frequently interact with them to gain additional insights. Ask about their preferences, hot buttons, and any subtle cues that could be useful in understanding their perspective. 2. Tailor your Communication Why: This ensures that your message is not just heard but also understood and valued. How: ↳ Seek inspiration from existing artifacts and pickup queues on terminologies, context and background on the give topic. ↳ Reflect on their goals and priorities, and integrate these elements into your communication. For instance, if they prioritize efficiency, highlight how your proposal enhances productivity. ↳Ask yourself "So what?" or "Why should they care" as a litmus test for relatability of your proposal. 3. Pre-socialize for support Why: It allows you to refine your approach, address potential objections, and build a coalition of support (ahead of and during the meeting). How: ↳ Schedule informal discussions or small group meetings with key stakeholders or their team members to discuss your idea(s). A casual coffee or a brief virtual call can be effective. Lead with curiosity vs. an intent to respond. ↳ Ask targeted questions to gather feedback and gauge reactions to your ideas. Examples: What are your initial thoughts on this draft proposal? What challenges do you foresee with this approach? How does this align with our current priorities? ↳ Acknowledge, incorporate and highlight the insights from these pre-meetings into the main meeting, treating them as an integral part of the decision-making process. What would you add? PS: BONUS - Following these steps also expands your understanding of the business and your internal network - both of which make you more effective. --- Follow me, tap the (🔔) Omar Halabieh for daily Leadership and Career posts.

In the high-stakes arena of #B2BSales, particularly when engaging the C-suite and Boards, "back of napkin math" is more than just a display of acumen – it's a potent catalyst for building #trust. Imagine a conversation where a senior leader articulates a critical business challenge, perhaps around CAC payback or share of wallet. The seller who can immediately and fluently grasp the underlying financial equation and articulate the potential impact of their solution, without missing a beat, speaks a language that resonates deeply. This isn't about complex modeling done offline; it's the agility to understand core drivers of their success and perform quick, insightful calculations within the flow of the conversation. For instance, if a Chief Revenue Officer (#CRO) mentions a goal of reducing customer churn, a seller with this skill can instantly frame the value of their solution in terms of retained revenue and lifetime customer value, demonstrating a tangible understanding of the CRO's priorities. This competence signals the seller not only listened - but also deeply comprehends which levers to use to solve the client problem. Why is this so crucial for building trust? Because it showcases several key elements that senior leaders value: Deep Understanding: The ability to perform this kind of rapid analysis demonstrates you've done your homework and truly understand their business model, challenges, and objectives. It moves you beyond being a mere vendor to a knowledge partner. #CustomerUnderstanding Intellectual Horsepower: It signals a sharp mind and the capacity to think strategically about their business. This builds confidence in your ability to deliver real value. #StrategicThinking Efficiency and Respect for Time: Senior executives are time-constrained. A seller who quickly gets to the heart of the financial implications respects this constraint and demonstrates a focus on outcomes. #TimeEfficiency Transparency: By engaging in these on-the-spot calculations, you reveal your underlying assumptions and logic, fostering a more transparent discussion. #TransparentCommunication Credibility: It elevates your status from a product peddler to a trusted advisor who speaks the language of business results. #TrustedAdvisor Think about it: when a seller can seamlessly weave in relevant financial implications – the potential ROI, payback period, impact on key KPIs – it’s not just data; it demonstrates commitment to the customer's success. It shows you're thinking beyond the product/service features and instead - are focusing on their strategic outcomes. To be clear - "Back of napkin math" isn't about being precisely accurate in real-time. It's about demonstrating a strong intuitive grasp of financial levers that matter to the customer and the ability to articulate value in their terms, instantly. This fluency builds a bridge of trust, making conversations more meaningful and impactful. #Gartner

I had a moment the other week where I gave a literal "elevator pitch." On-site with a big account, and a 6-figure deal in my pipeline. (Sidenote: it's always worth the travel to go see a big account.) I spent the day meeting with VP Sales, RevOps, Enablement, a whole group. But the one key person I hadn't yet met was their CRO. Until I was on my way to catch an Uber back to the airport, and he steps into the elevator. (He has no clue who I am or why I'm there at this point.) I say hi, he says hi. Then I mention he's built a sharp team, and I got a chance to meet them all. So naturally, he asks the old, "So what do you do?" question. This is my favorite way to answer that, with a simple framework you can use for your own "elevator pitch." (It's still comical to me we were in an actual elevator.) ______ (1) You know how ___________? ^ setup the situation / problem you focus on. (2) Well, you’re probably doing X, and it works really well. But it can’t Y. ^ you want them to feel like, "Oh man, you're so right" after sharing this. (3) So we let you do X and Y. How are you thinking about this? ^ you did a good job here if you get some version of "tell me more" after, and personally, I like ending with a question. _____ For me, that sounded like: (1) You know how buying teams have to sell you to their own execs, when your reps aren't in the room? (2) Well, you already have a Value Team writing business cases to help buyers in $1M+ deals, which works. But it's hard to scale downmarket. (3) So we let Commercial / MM reps generate these, with exec summaries not just ROI models. Which means you get the win rate you do upmarket — in a process that keeps pace with higher velocity deals. How are you thinking about business cases in MM? _____ Works just as well outside of an elevator too. Give it a shot this week.

Just watched another entrepreneur blow through his marketing budget. $100K conference booth. $250k ad spend. Cold email campaigns. Zero clue which (if any) actually work. How most entrepreneurs approach real estate sales: • Sponsor a $25k conference booth • Pay channel partners $15K referral fees • Launch cold email campaigns Wonder why they don’t know what’s working. The numbers they're missing: • Cost per acquisition by channel • Value of each funnel stage • Which touchpoints actually drive revenue 100% of them are surprised when I show them the funnel math. The systematic approach: Take a $200/month PropTech tool: 2.5 year average customer life = $5,000 LTV Smart entrepreneurs work backwards from LTV to value each interaction: • 1.5% website visitor to lead conversion • 20% lead to demo conversion • 15% demo to close conversion Suddenly every touchpoint has clear value: • Each website visitor = $15 • Each lead = $1,000 • Each demo = $750 Why this changes everything: That $500 cost-per-lead suddenly makes perfect sense. That $1,500 broker referral fee? Easy decision. You stop throwing money at channels that don't convert. The buyer complexity problem: But here's where most entrepreneurs still fail. Real estate has multiple decision makers. Your messaging needs to match the role: Asset Manager: Cares about operational efficiency Pitch: "Reduces operating costs by 15%, increasing NOI" Head of Acquisitions: Focused on deal flow and speed Pitch: "Analyze 3x more deals in half the time" Facilities Manager: Worried about day-to-day operations Pitch: "Eliminates manual processes, reduces staff workload" Development Director: Thinking about project timelines Pitch: "Accelerates project delivery, reduces delays" What separates winners from losers: Winners know: • Exactly what each funnel stage costs and converts • Who the real decision maker is (vs who takes the meeting) • Which stakeholders hold veto power • How to tailor messaging to each role's priorities Losers treat every prospect the same and wonder why deals stall. The bottom line: Start thinking systematically about funnel economics and buyer roles. Track every interaction. Know your numbers. Match your message to your audience. Details for our next workshop in the comments.

If 2024 taught us anything about Cold Email, it’s this: 👇 General ICP Outreach isn’t enough to drive results anymore. With deliverability getting tougher every day, there’s only one way to make outbound work: → Intent-Based Targeting Here’s how we do it at SalesCaptain to book 3x more demos ⬇️ Step 1️⃣ Identify High-Intent Triggers The goal? Find prospects showing buying signals. ✅ Website visits – Someone browsing pricing or case studies? (We use tools like RB2B, Leadfeeder, and Maximise.ai). ✅ Competitor research – Tools like Trigify.io reveal when prospects engage with competitor content. ✅ Event attendance – Webinar attendees or industry event participants often explore new solutions. (DM me for a Clay template on this) ✅ Job changes – Platforms like UserGems 💎 notify us when decision-makers start new roles (a prime buying window). ⚡️ Pro Tip: Categorize triggers: → High intent: Pricing page visits → Medium intent: Engaging with case studies This helps prioritize outreach for faster conversions. Step 2️⃣ Layer Intent Data with an ICP Filter Intent data alone isn't enough, you need to ensure the right audience fit. Tools like Clay and Clearbit help us: ✅ Confirm ICP fit using firmographics ✅ Identify the right decision-makers ✅ Validate work emails ✅ Enrich data for personalized messaging ⚡️ Key Insight: Not everyone showing intent fits your ICP. Filter carefully to avoid wasted resources. Step 3️⃣ Hyper-Personalized Outreach Golden Rule: Intent without context is meaningless. Here’s our outreach formula: 👀 Observation: Reference the trigger (e.g., webinar attended, pricing page visit) 📈 Insight: Address a potential pain point tied to that trigger 💡 Solution: Share how you’ve helped similar companies solve this pain 📞 CTA: Suggest an exploratory call or share a free resource ⚡️ Pro Tip: Use tools like Twain to personalize at scale without landing in spam folders. 📊 The Results? Since focusing on intent-based outreach, we’ve seen: ✅ 3x Higher Demo Booking Rates 📈 ✅ 40% Reduction in CPL (focusing on quality over quantity) ✅ Larger Deals in the Pipeline with higher-quality prospects It’s 2025. Let’s build smarter, more profitable campaigns. 💡 Do you use intent signals in your outreach? Drop me a comment below! 👇

One of the most gratifying parts of my role is interacting with clients and the investors we serve - in addition to Capital Group associates - around the world. Both cohorts make me smarter, inform my outlook for the industry, and help influence where Capital is headed as an organization.    A colleague of mine recently asked me how I prepare for so many meetings, specifically for clients around the globe. I’ll share with you what I shared with him:   1. Over-prepare (and then prepare again): There is no substitute for doing the hard work before you ever step foot in the room. I want to know as much as I can about what our client truly cares about and what challenges they face. Whether it’s an advisor meeting or a large institutional client, thorough preparation opens the door for deeper conversations. I also think doing the prep work is showing respect for our clients’ valuable time. 2. Be present: My focus and attention are on the client and only the client. The definition of a good client meeting is whether or not they found the meeting to be valuable. 3. Be genuine: If you’re reading off a script, you’ve already lost the opportunity to build a real connection. Be open, transparent, genuine, and imperfect. Over-preparedness lets you leave the briefing document behind so you can be in the moment for the client. 4. Follow-Up: Easy to say, hard to do consistently if you’re not passionate and disciplined about doing it.   Everyone has their own process. I don’t claim mine is any better, but it works for me, and most importantly – it’s meant to be impactful for our clients. #CapGroupGlobal