Here’s the #1 COMPLETELY PREVENTABLE mistake I see good founders make when fundraising:

They are not ready for investor questions.

Their pitch is tight, slide deck is polished, business is solid…and they stumble over the follow up questions.

And not only to do they miss a chance to further reinforce the awesomeness of their business and leadership with good answers, it is a red flag for investors:

“Ah, they were well-coached for the pitch but not actually good at selling, fundraising, strategy, thinking on their feet. In other words, the things you need to be a good startup CEO and leader.”

But like I said, it’s COMPLETELY PREVENTABLE with good preparation!

Here are the 6 strategies to bring your A game to the follow up questions and win the hearts (and wallets) of investors everywhere!

1. It’s the same questions.

Investors are boring business robots creatures of habit. They’ll ask the same questions over and over again. Yes, you’ll get variation. Different firms focus on different things. But you’ll quickly start to see patterns and common topics.

It’s like a job interview. There’s only so many different ways you can ask about someone’s biggest weakness (“caring too much” of course) and why they want to work here (“free snacks” says everyone to themselves but never aloud).

A.T. Gimbel gives a good overview here!

2. Investors will hone in on your weak spots.

Whatever you don’t want to talk about, that’s what investors will ask you.

It’s actually on purpose. Part of an investor’s job is to sniff out the mortal wounds, I mean, risks.

• Where could this business fail?

• What is the founder not saying?

• How much is still unknown/unproven?

It’s tempting to avoid the hard stuff.

Instead, practice that the most!

3. Most things have a positive spin.

A few examples:

• Did it take you 5 years to get to $100k in revenue? → What incredible resilience! You learned so much about your customers and what (not?) to do in that time.

• Do you have 1 very large customer and lots of small ones? → Your product solves a problem that affects companies of all sizes.

• Most of revenue come from partner sales? → Cost-effective and low-overhead GTM strategy; closing deals through partners while building playbook for an in-house sales team

• Slow sales cycle? → Low churn because companies rarely change vendors; when you win them, it’s a customer for life!

• Much smaller than competitors → more nimble to adjust to customer and market trends

Now, I’m not saying that if you have a positive spin, you will definitely raise money. Investors may not be swayed or may still pass.

But turning a negative into a positive is an evidence-backed strategy to raise 14x more money!

And, having a great answer to a hard question is a confidence builder and makes pitching fun. You internalize your positive answers, your outlook is contagious, and you may help an investor see things in a different light!

4. Use this AI prompt.

Here’s the thing about lists of possible investor questions. It’s a long list. And investors will usually pick 2-3 questions from that list.

Investors tailor their questions based on:

• your specific business

• their investment thesis (stage, what they look for, what their expertise is)

• what you did/didn’t talk about in your pitch

So there’s no universal list of questions but this list of 30+ questions is a great starting place.

Here’s the AI prompt to get you started:

I am building a startup to <short company description>. I am fundraising to raise <$ amount or type of round>. What questions will investors ask me?

If you have answers prepared for these questions, you’re in a good spot!

I’d also prompt AI for investor questions about <this part of my business that I’m nervous about or feels like a weak spot>.

And of course, ask AI to give you several options on how to answer those questions too!

5. Practice aloud.

Prep your answers. Take notes, write out sentences, use ChatGPT, whatever.

And then…SAY IT ALOUD.

Ideally, with a trusted question-asker who will give you real feedback.

The key to a great answer is not just content. It’s also delivery.

Confident, smooth, concise.

If you are great at those things naturally, congratulations and please message me about writing a guest post. 😂

If you are like the 99.9% of the rest of the world, a few run throughs will make a huge difference!

You still want to meet with your “worst” investors first to further practice and refine, but scheduling time to do several run throughs of Q&A (aloud!) before those first meetings will make a huge difference.

6. Don’t add more to your pitch.

It’s tempting to try to proactively answer questions by including more information in your pitch deck.

FOR THE LOVE OF EVERYTHING, RESIST THIS URGE.

You will go too fast. You will run out of time. It’s confusing. Slides have too much text. It undermines your credibility, the clarity of your message, and your overall ability to communicate.

I once got this great advice about presenting:

If you have an hour to present, plan material for 15 minutes and let the rest be Q&A.

Here’s why:

• The “audience” (whether it’s a keynote speech or a 1:1 sales meeting) can lead the conversation to what interests them.

• It’s more efficient, no boredom, no wasted talking!

• It creates a relationship; it’s a two-way conversation not you talking at someone.

• You better understand what the audience cares about.

• People feel special, listen more carefully, and have more buy-in when it’s *their* question.

• Questions mean learning and engagement. You can’t “zone out” when asking a question.

• Spoken answers feel more authentic and therefore more trustworthy than a scripted slide deck.

Pay attention the next time someone gives their 4 word elevator pitch. It almost always leads to a follow up question — which is FANTASTIC! Now you can customize the information based on that person’s expertise and interests.

But, Kathryn!?! What about this amazing slide that explains <very complex thing>? The visual helps people understand it so quickly and investors ALWAYS ask about it.

A picture is worth a thousand words.

As a preparer, I love having a slide ready.

Behold: THE APPENDIX

Not your kidney-shaped organ, it’s the catch all section after your pitch where you add slides that may be helpful during Q&A.

Approved by The O’Daily: (quickly!) pulling up a relevant slide from the Appendix during Q&A to better answer a question.

Did you practice answering questions before you pitched? What other tips would you share? Any questions that surprised or stumped you?