The biggest mistakes teachers make when teaching pitching
Five common mistakes that quietly sabotage pitch lessons, and the simple fixes that turn results around fast.
May 3, 2026 · 2 min read
Q: What are the biggest mistakes teachers make when teaching pitching?
The biggest pitch-teaching mistakes are: starting with slides instead of structure, over-coaching charisma, grading by gut instead of rubric, calling on volunteers (always the same students), and skipping peer judging. Fix any one and results jump. Fix all five and the unit transforms.
Running this with a class? SideHustle is free to play, needs no student accounts, and fits a class period. Get the game and the printable rules - we email you the link.
The story
Teachers who teach pitching well aren't necessarily the most charismatic; they're the most structural. The five mistakes that consistently sabotage pitch units are starting with slide design (slides are the last 10%, not the first), over-coaching charisma (which excludes shy students by design), grading by gut (which feels unfair and is), only calling on volunteers (which calcifies the same dynamic), and skipping peer judging (which leaves students dependent on the teacher's reaction). SideHustle® LIVE Labs avoids most of these by structuring the 60 to 90 minute Labs format around teams, rounds, and Funny + Fundable scoring. Professors and student groups at universities have independently adapted and played the free SideHustle® game in their own classrooms. For the foundational teaching method see how to teach pitching to high school students. Structure beats charisma in teaching just as it does in pitching.
What it means
If your pitch unit is producing the same three confident students every year, the problem isn't the kids; it's the structure. Audit your unit against the five mistakes. Fix the worst one first. Repeat next semester. Within a year you'll have a different set of students raising their hands. For the full educator playbook, see the educator guide to teaching entrepreneurship through play.
Try it
- Play free at playsidehustle.com
- See us live: Oct 1 at Pershing Hall in Austin. playsidehustle.com
Try SideHustle® free with your students
SideHustle® is edutainment: students pitch funny and fundable business ideas and learn to think on their feet, no slides and no worksheets. It runs in a single class period and scales from a handful of students to a whole grade. Opt in to play free and bring it to class this week.
Frequently Asked Questions
Should beginners ever start with slides?+
No. Slides are the last 10%. Spine and structure first.
Is peer judging too harsh?+
Not with a clear rubric. Peers are often kinder and more specific than expected.
What is the single biggest mistake when teaching pitching?+
Giving students preparation time. A week to prepare produces read-aloud slides and hides who can actually think on their feet. One minute produces real pitching.
Is it a mistake to have students pitch their own real ideas first?+
Usually, yes. A student defending their own idea has ego at stake and will play it safe. Invented, absurd businesses remove the risk and get better reps in early.
Should the teacher be the only judge?+
No. Rotating the judge role teaches evaluation, which is half the skill. Students who have had to justify a score pitch differently the next round.
Is it a mistake to skip the debrief?+
It is the most common one after over-preparation. The rounds generate the material; the five-minute debrief is where students learn what separated the winning pitch from theirs.
Do teachers over-focus on confidence?+
Yes. Confidence is downstream of structure. Praising charisma tells quiet students they cannot win; praising a well-built pitch tells them exactly how to.