Best Practices for Engaging Leadership in Kickoff Meetings

If you’re looking to impress senior leadership and get your team’s projects approved—these 6 tips are the way to go about it. 1️⃣ Pre-wiring: Host a prep meeting before the main event. Get feedback from peers in similar industries to ensure it will resonate. This can help you refine your points, anticipate questions, and ensure your content is perfectly tailored to resonate with executives. 2️⃣ Frame topic QUICKLY: Within the first 30 seconds, make clear what your presentation is about. Being on a time-crunch…Executives want to know immediately why they should care and how it impacts the business. 3️⃣ Set clear expectations: Outline the agenda and what you’ll cover right from the start. Let the executives know what they can expect to gain by the end of your talk. 4️⃣ Use an inductive approach: Lead with your main conclusion, then support it with data and reasoning. This gets straight to the point and helps executives grasp your key message quickly. 5️⃣ Balance your time: Limit your talking to 50% of the time. This promotes a two-way dialogue and allows you to adapt based on their feedback. They value conversation NOT monologue. 6️⃣ Be ready to zoom out: When questions arise, step back and address broader issues. Executives are looking for strategic insights, so contextualize your answers to align with overall business objectives. Remember, winning over a tough crowd has specific requirements. → Address the elephant in the room. → Stay focused on your objective & respect the clock. 👉What's your go-to strategy for engaging tough audiences? Let me know below how they’ve worked for you!

Contracts don’t equal access. Execs don’t owe you their time. Lately, there’s been a big push for CSMs to engage executive stakeholders—and while I get the intent, here’s a reality check: Execs won’t engage just because YOU want them to. I get random requests all the time—CSMs asking me to jump on calls simply because I’m an exec. No context. No clear value. Just vibes. It’s wild. Also, can we all agree that “engagement” doesn’t just mean meetings? There are better, smarter ways to get an executive’s attention. If you actually want to engage execs (and not just check a box), here’s how I prefer to do it: 1. Set Expectations Early In your kickoff meeting, ask execs what role they want to play in the partnership. Offer examples of how other leaders stay involved—give them a menu of options. 2. Be Flexible Not every exec wants a meeting (shocker). Try reports, async updates, or a quick summary email. Adapt to their style instead of forcing yours. 3. Share Actual Value If you’re reaching out just to check in, don’t. Execs don’t care about your internal timelines—reach out when you have insights or outcomes that matter to them. 4. Title Matters—Match It Want to engage a VP? Bring in your VP. Trying to reach the C-Suite? Send your C-Suite. Peer-level conversations open doors. 5. Keep It Short No one’s reading your novel-length emails. If your message isn’t clear and compelling in the first two lines, it’s getting deleted. Bottom line: A contract doesn’t entitle you to an executive’s time. Earn their attention. Deliver value. That’s how you win. _____________________ 📣 If you liked my post, you’ll love my newsletter. Every week I share learnings, advice and strategies from my experience going from CSM to CCO. Join 12k+ subscribers of The Journey and turn insights into action. Sign up on my profile.

How I got my projects endorsed by C-suite leaders without battling for attention In 3 Steps 𝗦𝘁𝗲𝗽 1: 𝗣𝘂𝘁 𝗺𝘆𝘀𝗲𝗹𝗳 𝗶𝗻 𝘁𝗵𝗲 𝘀𝗵𝗼𝗲𝘀 𝗼𝗳 𝗮𝗻 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲   – Understand their pain points and priorities. Executives think in terms of strategy, ROI, and risk management. They don’t have time for the granular details—they need to know how the project will support their goals. 𝗦𝘁𝗲𝗽 2: 𝗖𝗿𝗲𝗮𝘁𝗲 𝗽𝗿𝗼𝗷𝗲𝗰𝘁 𝗿𝗼𝗮𝗱𝗺𝗮𝗽𝘀 𝘁𝗵𝗮𝘁 𝗲𝗺𝗽𝗼𝘄𝗲𝗿 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻-𝗺𝗮𝗸𝗶𝗻𝗴   – Present roadmaps with clear milestones, dependencies, and outcomes. The aim is to make it easy for them to connect the dots and understand how the project aligns with business objectives. Simplify without oversimplifying. My number one tool for creating these roadmaps is Office Timeline. 𝗦𝘁𝗲𝗽 3: 𝗗𝗲𝗹𝗶𝘃𝗲𝗿 𝘁𝗮𝗶𝗹𝗼𝗿𝗲𝗱 𝗽𝗿𝗼𝗷𝗲𝗰𝘁 𝗿𝗲𝗽𝗼𝗿𝘁𝘀   – Design reports specifically for executive audiences. Highlight key insights, risks, and wins. Ensure these reports answer: “What do they need to know right now?” Empower them to make informed decisions without wading through excess data. These steps aren't just tactics—they build trust and demonstrate that your project management approach aligns with leadership goals. What’s your go-to method for securing executive buy-in? Share your thoughts in the comments! Like if you found this useful, and follow for more insights on project management and leadership alignment. Don't forget to share this with your network! 👥💡