My favourite question to ask founders during a first introductory call is: what were the pivotal moments in your startup journey so far, and how did you deal with them?

This gives me, first of all, most often an interesting story to listen to, but it also shows progress and learning capabilities of the founders and it gives some signs about how resilient they are.

So what are good questions to ask an investor? Probably the first meeting is all about getting to know each other a bit better. The investor might have already seen your pitch deck, so you can expect that he or she is prepared (although some will just open your deck 2 minutes before the meeting starts). I think it’s important to let that first meeting be a two-way street, instead of a monologue by the founder, perhaps fueled by question-after-question by the investor.

Most investors will tell you they are “hands-on”, and have a great network and expertise to share. As a founder I would be curious: can you make the “network” or “expertise” part more concrete? Can you give examples of how you supported portfolio companies?

Another great question is: what did you like most about our proposition and where do you expect our challenges will be? This gives insights on how the investor assesses your company, if they understand where you’re heading and if they can give solid advice that actually makes sense. Very good to know if you’ll be working together for some years!

What are your best questions to ask investors?

Read more insights in Startup Funding book, the book about investor readiness, fundraising and deal terms that I wrote together with venture capital lawyer Sjoerd Mol to help founders to nail their fundraising process. Order it via bol.com, Amazon or your local bookstore.