Choose Investors Who Ask the Hard Questions

Choose Investors Who Ask the Hard Questions

When you're raising capital, it's easy to be blinded by term sheets, valuations, and big brand investor names. But amid the nervousness and excitement, there's one subtle signal that can tell you everything about an investor’s value: the questions they ask.

If your prospective investors aren’t asking hard questions—especially about your cyber security posture—you should be asking yourself why.

Cyber Security Isn’t Optional—It’s Foundational to Every Business, yours Included

Startups are prime targets for cyber-attacks. Whether it’s customer data, proprietary code, or third-party integrations, your digital assets are your business. Any investor who doesn’t probe into how you’re protecting them is overlooking a fundamental operational risk.

The best investors know that a data breach can destroy trust, derail growth, and strip a company’s valuation. That’s why they dig deep into your security practices—not to trip you up, but to help you build a cyber resilient foundation.

What It Means When They Don’t Ask about Cyber Security

An investor who skips cyber security due diligence may also be:

• Unfamiliar with operational risk

• Focused solely on short-term returns

• Ill-equipped to support you through cyber incidents

• Blind to cyber regulatory and reputational responsibilities

That’s not just a missed opportunity—it’s a liability.

What the Right Questions Sound Like

Great investors will ask you questions like:

• “How do you manage access to sensitive systems?”

• “What’s your cyber incident response plan?”

• “Are you aligned with any security frameworks like ISO 27001 or NIST”?

• “Have you conducted a recent penetration test?”

These aren’t pass fail/questions—they’re signs of a partner who’s thinking about the long-term.

You Deserve a Partner, Not Just a Cheque

The best investors aren’t just capital providers. They’re collaborators, advisors, and safety nets. When they ask tough questions, they’re showing you they care about your future—not just your next round.

So, when you’re choosing who to bring into your investment eco systems don’t just look at the money. Remember, great investors ask hard questions.

Final TPCS Thoughts

In a world where one cyber security incident can undo years of progress, cyber security is a boardroom issue. Founders who want to build enduring companies need investors who understand that—and who aren’t afraid to ask the hard questions.

Because the right cyber security questions today can save your company growth tomorrow.