4 Pitching Mistakes That Sabotage Your Success—And How to Fix Them Fast

We are creatures of habit. And not all habits serve us well.

Some bad habits are harmless, like jaywalking. Others are harder to ignore, like a poorly structured pitch.

The good news? Almost any bad habit is kickable—if you know what to look for.

After running a series of pitch training workshops last year, we identified some of the most common habits that hold people back. If you recognise any of these, your mission this year, should you choose to accept it, is to eliminate them before they eliminate your opportunities.

1. “I’ll just use what I used for…”

Recycling an old pitch might seem like a shortcut, but it’s often a red flag.

It can mean your head’s not in the game.

Your next big idea, new client, or career-defining opportunity deserves more than a retread.

Start with your structure. Define the outcome you’re after. Once you’ve done that, you’ll likely see gaps that require original thinking and problem-solving.

Once you know where you’re headed, then you can draw on previous work. But never before.

2. “I’ll wing it. They’re too busy to answer my questions…”

Too many pitchers assume decision-makers are too busy to answer a few pre-pitch questions.

This is self-sabotage.

Yes, reaching out to someone you don’t know—especially in a leadership role—can feel uncomfortable. But consider the upsides:

• The worst they can do is say no. That’s on them, not you.

• If they say yes, you gain key insights into their needs.

• You build rapport before the pitch even starts.

Most subject-matter experts love talking about their expertise. If you ask the right questions, they’ll often tell you exactly what they need from you.

Great start, Maverick.

3. “I’ll get to it tomorrow.”

Procrastination is a pitcher’s worst enemy. It robs you of time, weakens your preparation, and sets you up for failure.

If you catch yourself putting off your pitch preparation, do two things:

• Prioritise. Decide how important this pitch is compared to everything else on your plate. Allocate time accordingly.

• Diarise. Block out time in your schedule and break it into manageable chunks.

Use your structure to stay on track, define your key points, gather supporting evidence, and then rehearse.

Your future self will thank you.

4. “This is how I’ve always done it.”

W. Edwards Deming, the father of continuous improvement, once said, “Every system is perfectly designed to get the results it gets.”

The same applies to pitchers.

If you were happy with your results, you wouldn’t be reading this.

Ask yourself:

• Am I using a strong structure?

• Do I truly understand my content?

• Is my team aligned on our goals and messaging?

• Are we collaborating for a compelling outcome?

If the answer to any of these is no, there’s room for improvement.

The Bottom Line

Pitching doesn’t have to be risky business, but it does require leaving self-sabotaging habits behind.

Clear structure. Thoughtful preparation. A willingness to challenge how you’ve always done things.

That’s how you stop sabotaging yourself and start winning more opportunities.

Happy pitching.