Preparing for Client Meetings with Multiple Stakeholders

The one strategy every product leader needs before attending high-stakes large stakeholder meetings: Ever walked into a high-stakes meeting only to watch it derail in minutes? You're not alone. The most successful executives I know never attend big meetings without doing this first: Shuttle diplomacy, which is all about meeting key players one-on-one before the group convenes. This practice transforms outcomes. Why it works: ◻️ Surfaces objections in a low-risk environment ◻️ Let's you tailor your message to each stakeholder’s priorities ◻️ Builds coalition support before anyone's in the room ◻️ Gives you time to refine your approach based on feedback ◻️ Prevents public disagreements that create lasting friction How to do it effectively: ◻️ Identify 3-5 critical stakeholders (the decision-makers) ◻️ Schedule brief 1:1s at least 48 hours before the meeting ◻️ Present your core idea in their "language" and genuinely ask for input ◻️ Adjust your proposal to address their concerns ◻️ Acknowledge their contributions during the group meeting ◻️ Frame your pitch around company goals so stakeholders see it through that lens This simple practice has saved me countless hours and dramatically improved my implementation success rate. What has saved you countless hours in stakeholder engagement?

You prepped hours for the demo. 10 Stakeholders show up. Then… ghosted. Here’s some ways you can prevent it for next time: 1. Let your Champion summarize previous calls, not you. You want to show you listened, so you recap the pain points. Maybe you even made a hypothesis slide. But you’re the vendor. You don’t have trust yet. Let your Champion reframe the problem in their words. Their team will trust them more than they trust you. 2. Talk to Key Stakeholders directly Asking “anyone else want to add anything?” will always get you: “Nope, all good.” Instead, try asking key roles direct questions with context: “I know Allison just shared some of the challenges we’re planning to address today, but Kim, I assume as the CMO you’ll be less in the weeds and more consuming this data — what type of challenges are unique to you and how can we make sure to use your and the team’s time most valuably today?” Make it easy for them to contribute. Make it about their success, not your product. Leave it open ended to get to the true answer, avoid closed/leading questions. 3. Engage the full team. Don’t just talk to execs and your champ. The best leaders want their team involved and to be valued. If you ignore them, you disrespect the people they trust. 4. Make every second count. That 45-min call? Easily a $2,000+ meeting to their business. Finish early if you can. Don’t waste time. Execs notice. 5. Keep doing discovery throughout the call. Don’t show up with 10 discovery questions. Thread smart questions into the flow of the demo. 6. Bring the right resources. If they brought the full crew, you should too. Be ready to answer anything and try to avoid “I’ll follow up on that.” Ask for questions ahead of time from your champ so you can better predict what will be needed. 7. Keep your Champion after the call. In big groups, real feedback comes after the room clears. Stay back with your Champion to debrief and understand how you did (you should be working for them to build consensus). Plan your next step before you lose momentum. It’s not always about what you say on the demo.. it’s how you prepare, engage stakeholders, and arm your Champion to lead internal conversations.

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.

Last week I watched a rep almost torpedo a $500K deal in real time. The mistake? He walked into a 90 minute CFO demo with his co-founder, multiple departments and zero systematic approach. Just "winging it" with relationship selling. Here's what I told him during our emergency coaching session: Enterprise deals aren't bigger versions of SMB deals. They're completely different animals that eat unprepared reps alive. Most reps panic when they see 8+ people on a Zoom call. They start rambling, lose control of the conversation, and watch their champions get overruled by executives they've never met. I've been in the trenches with enterprise teams for 15+ years. Here's the exact 5 step framework I use to execute complex deals without losing control: 1️⃣ Create the executive battle plan Write an internal executive summary before any big meeting. Include deal context, all stakeholders, identified pain points, and clear success metrics. Your entire team needs to know what's at stake and who's doing what. 2️⃣ Pre meeting stakeholder outreach Reach out to each attendee individually: "Looking forward to our conversation on the 23rd. What are 1-2 specific things you want to see covered to make this valuable for you?" Many won't respond, but the ones who do give you gold. 3️⃣ Pressure test your champion Ask your champion directly: "What's the CEO's stance on this project? How about the CIO?" Most reps never ask this question. Champions often don't know, which tells you everything about deal risk. 4️⃣ The flyover strategy When you can't reach key stakeholders directly, have your executive send a simple email: "Sounds like your team is evaluating X. I'm here to support this potential partnership. Any questions, don't hesitate to reach out." No need for them to call back. 5️⃣ Champion gauging system Track champion strength with specific questions: "When we last spoke, you were 60-40 in our favor. How are you feeling now?" Get them to give you a number. Anything under 70% means you have work to do. This systematic approach separates enterprise closers from order takers. The detailed breakdown with exact scripts and templates is in the carousel below ↓ — Sales Leaders! Want to be a world class sales manager and get your team crushing enterprise level deals? Go here: https://lnkd.in/gfn_qi9E

If you fumble the room, you lose the deal. One of my coaching clients had a big meeting coming up: Multiple stakeholders. Six-figure potential. One shot to get alignment or risk the deal stalling out. Here’s how we prepped: 1️⃣ Mapped the room – Who’s who? What does each person care about? Who’s the real decision-maker, and who just thinks they are? 2️⃣ Built a business case – Clear ROI story, tailored to each persona. Product came last. Their priorities came first. 3️⃣ Prepped for pushback – We anticipated objections and wrote responses they could deliver with confidence (not defensiveness). 4️⃣ Assigned roles – Everyone knew when to lead, when to listen, and how to close strong. 5️⃣ Practiced the open and the close – Because that’s where deals are won or lost. They didn’t just “get through” the meeting. They earned trust. They moved the deal forward. And they walked out with a champion.