“Every Q&A is a negotiation.”

This insight from Jacqueline Kapur, Health2047’s Chief Financial Officer, captures a fundamental truth about fundraising that many founders miss. When you’re raising capital, you’re not just being evaluated—you should be evaluating your potential investors just as rigorously. Here are several things to ask during the fundraising process.

Ask for their track record

Start by asking questions that probe how long an investor might be committed to funding your company, such as asking what their follow-on strategy typically looks like. “Don’t accept vague promises,” advises Kapur. “Ask for specific examples of how they’ve supported other portfolio companies through challenges. Which companies did they double down on during tough times? Which ones did they abandon? The answers reveal their true commitment level.”

Test their capital deployment strategy

In today’s market, many investors are conserving capital for existing portfolios rather than making new investments, Kapur notes. “You need to know where you stand in their priorities. Are they actively deploying capital or primarily supporting their current portfolio? This directly impacts their ability to lead or participate in your future rounds,” she says.

Get specifics on “support”

When investors promise to help with fundraising, dig deeper. “There’s a vast difference between an investor who shares their contact list and one who actively pitches alongside you,” says Kapur. She suggests asking for concrete examples of how they’ve helped companies raise subsequent rounds, navigate legal challenges, or overcome operational hurdles.

Uncover hidden expectations

“While investors will track obvious metrics like revenue and EBITDA, understanding their qualitative milestones helps you deliver what truly matters to them,” says Kapur. “Ask what non-financial achievements they value—team building, strategic partnerships, technical milestones—so you can align your efforts with their expectations.”

Negotiate like you mean it

Here’s where many founders falter, notes Kapur: they accept terms without discussion. But thoughtful negotiation isn’t just accepted—it’s expected. Your ability to negotiate fairly with investors demonstrates the skills you’ll need when dealing with customers, partners, and future investors.

Consider creative structures if standard terms don’t work, she advises. “For example, if an investor wants 20% but that feels disproportionate at your stage, propose 10% upfront with the remaining 10% as an earn-out based on specific deliverables.”

Calculate the true cost of capital

When investors ask for significant equity, ensure you understand exactly what you’re getting. “A fund that takes 20% but provides hands-on support, board participation, and active fundraising assistance may offer far more value than one taking 5% as a passive investor,” says Kapur.

Maintain a partnership mindset

Lastly, the best founder-investor relationships are true partnerships. By asking tough questions upfront, Kapur stresses you’re not being difficult—you’re laying the groundwork for a transparent, productive relationship that can weather the inevitable challenges ahead.

Your investors are evaluating whether you have what it takes to build a successful company. Show them you do by being just as rigorous in evaluating them. After all, as Kapur reminds us, you’re not just raising money—you’re negotiating the terms of a long-term partnership.