Pitching Up? Ask These 5 Questions First.
It was a great idea. And it completely fell flat.
I remember the meeting clearly. I was pitching a portfolio move, recommending we divest one of our businesses. The analysis was strong. The logic made sense. The strategy was sound.
But I walked out with nothing. No decision. No traction. No clear next step.
Not because the idea was wrong. But because I didn’t frame it right.
I hadn’t thought through what really mattered at the C-suite level.
I still remember that feeling afterward, that gut-punch deflation. But looking back, I wasn’t actually ready to lead that conversation. Not because I wasn’t capable, but because I hadn’t done the real prep: the strategic, executive-level thinking that earns a room’s attention and trust.
You’ve Got a Big Idea. Now What?
It’s smart. It’s strategic. It could move the business forward.
But before you pitch it to the C-suite, a board, or even your boss, pause.
Because a good idea isn’t enough.
You need clarity. Confidence. And a point.
After years in executive leadership, here’s one thing I know for sure: the fastest way to get a “no” is to walk in unprepared for the questions that matter most. The ones that don’t show up on your slides but show up in every decision-making room.
If you want your idea to land (and stick) ask yourself these five questions first:
✅ 1. What Problem Am I Solving?
Not: “What makes this exciting?”
But: “What pain point, inefficiency, or gap is this fixing?”
Executives are wired for impact. Start with the problem make it real, urgent, and specific. Bonus points if you can quantify it. This isn’t about energy. It’s about relevance.
✅ 2. Why Now?
Timing changes everythingMaybe the market has shifted. Maybe a customer is asking. Maybe waiting would cost us more.
Make the urgency undeniable. A good idea with bad timing gets shelved.
A great idea with great timing gets funded.
✅ 3. What’s the Upside and the Risk?
This is where many promising ideas lose momentum. Excitement without a view of the trade-offs feels naïve.
Show you’ve thought it through. What’s the upside? What’s the cost of doing nothing? What are the risks if we do move forward?
You don’t need all the answers but you need to show you’re asking the right questions.
✅ 4. What Would It Take to Win?
Budget. Time. People. Support.
Paint the path. Leaders want to know how we get from pitch to performance. Be crisp. Be clear. You’re not just selling an idea you’re proposing a strategy.
✅ 5. What Will Success Look Like?
Don’t leave your pitch open-ended.
Define the finish line. What will change? Who will benefit? How will we measure it?
A great pitch starts with purpose and finishes with focus!
🎯 The Real Goal? Confidence, Not Convincing.
❌ Senior leaders don’t need drama.
✅ They need direction.
❌ They don’t want perfection.
✅ They want clarity, accountability, and action.
❌ They’re not grading your presentation skills.
✅ They’re evaluating your leadership mindset.
And when you ask these five questions before walking into the room, you walk in not just as a messenger but as a decision-maker.
Your Turn
Got an idea you’re thinking about pitching?
Before you send the invite, block 15 minutes on your calendar.
Run through these five questions. Better yet, ask a trusted peer to push back on your answers.
Because when you pitch with intention, you don’t just get heard.
👉 You get momentum.