Asking investors the questions that matter

Asking good questions gives you a behind-the-scenes look at what a prospective investor is looking for, accelerates the fundraising process, and cements you as a savvy and proactive operator. If you have multiple offers, they'll help you select the best fit; if you don't, they will still prepare you for the partnership you are about to enter. And sometimes, the intelligence and confidence that good questions signal can be the final clincher that gets a deal over the line.

Ben Christensen is founder and CEO of Cambium. In the first of our series in partnership with Unreasonable Impact, we sat down with him to break down the questions you should be asking investors, and what to do with the answers you get.

Why asking questions matters

You’ll likely be one of 20 calls the investor will take this week, and they're probably jumping into yours five minutes late, still mentally wrapped up in the last conversation. An unexpected, memorable question, especially at the beginning of the call, can pattern interrupt and snap them out of autopilot. 

Questions also give you a chance to evaluate the investors, which is good for two reasons. First, it helps you decide whether they’re someone you actually want to work with. Second, they also show the investor that this conversation is a two-way street, and you’re assessing fit as much as they are.

At the same time, your questions have to come from an authentic place: you can’t just ask a question for the sake of it being interesting. You need to actually want to know the answer – and know how to use it.

Three types of questions to ask

1. Questions that uncover what the investor wants

What are the goal posts?
Take control of the conversation from the get-go. Once you've exchanged pleasantries, ask about the investor’s goal posts – fund size, check size, ownership targets, and what a perfect investment looks like for them.

If what they outline doesn't seem like a fit, suggesting as much will often trigger a psychological effect where they’ll start talking themselves into why it could still work. But if it is a great fit, you now know exactly which buttons to push.

What's really moving the needle?
Follow up by asking what separates the companies they like from the ones they actually invest in. Their answer will give you the three to five points you need to hit in the rest of the meeting.

2. Questions that evaluate the investors

Investors are used to being the ones asking the questions. By making it clear that you’re also evaluating them as someone you want to work with, you shift the power balance. Rather than coming across as an eager-to-please founder, you’re checking whether the conversation is even worth your time. Again, this stance will make them work to convince themselves that they do in fact want to be there.   

Do they share your core values?
Early on in the call, make it clear that you care deeply about who you work with and want to make sure there’s a good fit. Pick a core value that genuinely matters to you, then find a question that reveals whether or not they share it. If you value self-reflection, ask about their process for learning and growth. If you value honesty, ask about a time they were wrong.

How do they deal with conflict? 
All companies go through ups and downs. Ask the investor what the founders they've worked with would say about how they act in hard times. You can't expect to get the full truth, but you'll see a huge difference in how people respond – specific examples are a good sign they'll follow through, while general, handwavy responses are a big red flag.

What does operational excellence look like for them?
Ask the investor to walk you through how they'll actually work with you. How will they make sure they have enough context to stay up to date and create real value? 

Beyond giving you a window into their process, this question also has the benefit of demonstrating you have relentlessly high standards, and only want to work with people and firms who share them.

Whether to walk away
In fundraising, having more options on the table is always a good idea. Even if you don't like the answers you're getting, it can still be worth keeping the conversation going – it may result in a term sheet you can leverage, even if the investor isn’t someone you’ll end up working alongside.

3. Questions that establish the right dynamics

Here, your questions aim to create a sense of pressure and FOMO, signaling that investors need to work to be part of what you're building, not the other way around. 

What do the best companies do right?
Ask what they've seen the best founders do to successfully scale from Series A to Series C. Their answers will give you some unique and useful ideas, as well as showing that you’re focused on the long term. 

What’s going to get people excited? 
Ask what will get their partners most excited about this deal. What makes it a great fit for their firm? The call then closes with them preemptively pitching your company.

When should we talk again? 
Towards the end of the call, let them know that you’re trying to be selective and that you only have a small window of time, because things are moving quickly. To best manage your time and resources, you can ask for a follow up call there and then or suggest both sides follow up with questions by email.  You can even ask for a founder reference on the spot – you’ll get a softball, but it helps expand your network. 

If they’re happy to continue the conversation, this will speed things up, but if not, you can move on quickly and save time. However, note that this doesn’t always work – some investors won’t appreciate being rushed.

Ben founded Cambium with a vision to build people-first climate solutions rooted in material reuse. Under his leadership, Cambium has scaled nationally, grown to 8 figures in revenue, and become the largest salvaged wood company in the U.S.—while helping bring AI and modern software infrastructure to a legacy industry. He holds an MEM from the Yale School of Forestry & Environmental Studies and has spent nearly a decade working across climate, forestry, and carbon systems. Before founding Cambium, Ben worked on the Natural Infrastructure team at the World Resources Institute, was a backcountry guide, and conducted nanochemistry research at Sandia National Laboratories. 

Ben is a Forbes 30 Under 30 honoree, and Cambium has been recognized by TIME as a Best Invention and by Fast Company as one of the Most Innovative Companies. He is also a TEDx speaker and has shared his insights on stages across the US. Outside of work, Ben is an ultramarathoner who complete races across the Sahara and multiple 100+ milers.