Top 10 questions to ask potential investors – from industry experts

Benjamin Debonneville
Founder & CEO
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In the fast-paced world of startups, we're often so prepared to field a volley of tough questions from potential investors that we forget the power of flipping the script.

Don't get me wrong, acing the answers is crucial, but have you ever thought about the questions you should be throwing their way?

Sure, they're opening their wallets, but are they the right fit for your business journey?

Think of securing an investment as akin to finding a life partner. Would you say "I do" before delving deep into knowing them? No? Then why take a backseat in understanding your investor?

After all, it's not just about cash, terms, and valuations. The magic lies in the rapport you share with your investors.

So, ready to roll up your sleeves and get to know your potential financial soulmate better? Let's get started and dig deep into 10 potential questions founders should ask investors.

Remember: when it comes to your startup's future, no question is too big or too small.

Uncover the Ideal Investor: Dive Deep into Your Research

Before diving headfirst into the pool of questions to ask your potential investors, let's slow down and grab a snorkel first.

Why, you ask?

Because you've got a deep dive ahead. You're on a mission to uncover the ideal investor, the one who aligns perfectly with your business ethos and industry.

This is no ordinary scavenger hunt. It's the precursor to a successful fundraising round and a long-lasting relationship with your investor.

Let's be honest, you're not searching for a fleeting fling here. This is more akin to a treasure hunt, and what you're after is nothing short of pure gold.

Take your time, arm yourself with patience, and get ready to put on your Sherlock Holmes cap. Research, analyze, cross-check, repeat.

The journey to find your investor match is a winding road that demands a fair share of your time and energy.

But, believe me, when you strike gold, it's worth every bit of the sweat and grind.

10 Questions to Ask Investors

After diligent sleuthing, you've found your potential investor. Now, it's showtime!

Remember, a successful founder-investor meeting isn't just a Q&A session for you. Flip the narrative and throw your hat into the ring with these 10 must-ask questions.

Ready to turn the tables? Let's dive in!

What Motivates You to Support Early-Stage Startups?

Kick things off by understanding what fuels your investor's passion for early-stage startups. It's about more than just figures on a balance sheet.

Peel back the corporate layers and delve into their motivations. It’s like dating - you're seeking a connection that runs deeper than just business.

Are they inspired by innovation? Do they get a kick out of nurturing budding entrepreneurs?

Remember, your investor needs to share your enthusiasm for your venture. By uncovering what makes them tick, you'll be able to assess if there's a shared spark.

So, don’t shy away from getting personal. This first question can pave the way for a fruitful business relationship.

Ready to take the plunge? Let's dive deeper!

Do you Lead Rounds, fill-out rounds/co-invest, or both?

You've ignited the conversation, now let's step up the game.

This one's a game-changer. Why? Because, like a master conductor leading an orchestra, a lead investor can set the rhythm for your fundraising symphony.

But wait, don't put all your eggs in one basket! The investor who prefers a co-lead role or filling out rounds can also be a valuable player on your team.

The key is understanding their preferred role. Will they take center stage or share the spotlight with other co-investors? After all, you're assembling your dream team here, and each player has a unique part to play.

So, are you ready to delve into the intricacies of your potential investors' roles? Let's hit it!

How much of the Funds are for “primary” vs. “follow-on?

Let's talk numbers! When it comes to investments, it's important to know the VC's reserve strategy.

Picture it like this: They make an initial splash, then set aside funds for future rounds or to rescue startups in need. It's like having a secret stash for a rainy day but with a twist.

The reserves are often expressed as a ratio, like 4:1. So, if they put in $1 million in your seed round, they theoretically have $4 million reserved for your future needs.

But here's the catch—don't assume they'll always dip into that pool, especially if you hit a few bumps on the road.

Knowing the follow-on investment percentage is like having an extra ace up your sleeve. So, are you ready to uncover their financial magic tricks?

Let's do the math!

What Would You Like to Get from This Investment?

Now, let's get into the nitty-gritty: What does your investor hope to reap from this deal?

Is it purely about the financial return, or do they crave something more? Are they hunting for a quick exit or inspired by your company's vision for a positive impact?

Think of this as a reality check. If they're picturing a high-speed car race, but you're cruising in the slow lane, the match might not be as perfect as you thought.

Being clear on expectations from the get-go saves you from a bumpy ride later.

So, before you hit the accelerator, make sure both of you have your eyes on the same finish line.

How Many Investments have You Made in the Last Six Months?

Want to know if your investor is the real deal?

Ask about their investment dance card! Understanding their recent investments gives you a peek into their current interests and focus areas.

Consider this as the investment world's version of social proof.

Do they have a winning streak with successful ventures? Are they hailed as a guiding light by other entrepreneurs they've backed? Don’t be shy about asking for references, either.

Remember, you’re not seeking a passive financier but an active ally who's in the thick of things. Pitching to a dormant investor is as futile as a Wi-Fi-free laptop!

So, before you start your pitch, make sure your potential investor is ready to play the ball.

Do you Typically Take Board Seats?

Here's the big question: Does your investor prefer a courtside seat, or are they happy cheering from the stands?

In simpler terms, will they seek a seat on your board? If yes, who's their chosen delegate? This question isn't just about power dynamics—it's a probe into their commitment.

Sure, money talks, but time and reputation? They shout volumes about how much they value your venture.

Keep in mind, an over-involved investor can feel like a micromanaging boss, while the right guidance can be a boon.

Gauge their expectations, and ensure your philosophies align. After all, it's your game to play, but it's always wise to know who's coaching from the sidelines!

Let's dribble on!

What is the Investment Decision-Making Process?

When it comes to securing funds, not all investors pull the trigger at the same speed. Their investment decision-making process can be an intricate dance.

So, what's the tune they sway to? Is the decision a solo act or a full-fledged performance involving a crew?

Unmasking their decision-making mechanism can provide valuable insights into their evaluation criteria and due diligence. Expect them to dive deep into your financial health and seek solid references.

Remember, the higher the stakes, the deeper their probe will go.

So, get acquainted with their rhythm early on - it could make your fundraising saga a harmonious ballet rather than a clumsy foot shuffle.

How Often Should We Expect to Meet After Funding?

Got the check? Great! But how often do you get to catch up with your investor post-funding?

You see, money isn't the only currency flowing between founders and financiers—communication is equally vital.

Some investors might be fine with quarterly tête-à-têtes, while others prefer annual PowerPoint parties.

Don't confuse 'investor' with 'intruder,' though! It's about ensuring a steady stream of interaction, not an overflowing inbox.

Asking this question also serves as a litmus test for their commitment. If they're open to regular chats, it's a sign they're in it for more than just the financials.

So, are you ready to set the meeting rhythm? Let's sync our calendars!

How Do You Handle Potentially Competitive Situations?

Ready for a glimpse into your potential investor's crystal ball?

This question seeks to tap into their industry insights and how they foresee potential speed bumps on your sector's horizon.

It's a fantastic opportunity not just to pick their brains but also to match your understanding of your industry's outlook with theirs. Do they know the terrain well enough to ride the waves of risks and challenges?

Moreover, don't forget to ask how they navigate the tricky waters of potential competition within their investment portfolio.

Remember, the perfect pitch might need some tuning based on their feedback.

After all, isn't adaptability the entrepreneur's middle name?

In terms of Exits, What's Your Investment Lifespan?

In the high-stakes game of start-ups, an 'exit' isn't about heading for the door; it's about sailing into the golden sunset, all aboard the good ship or perhaps being whisked away by a big industry player.

But when is your potential investor planning to disembark?

This vital question helps chart your shared journey's course and timelines. The investor's exit expectations can shape your growth strategies, ensuring you shine as a beacon to prospective buyers or become the belle of the stock market ball.

Remember, each investor's journey has a different lifespan, and it's crucial to align yours to navigate the exciting path to start-up success!

Be Judicious With Your Questions

Hold your horses! When it comes to firing off these questions, timing is everything.

While "Do you lead?" deserves a front-row seat in your debut meeting, the rest deserve a more strategic approach.

Think of it as a sprinkle of seasoning—add them gradually via email exchanges, subsequent meetings, and moments of mutual interest. Let curiosity be your guide, and let the conversation unfold naturally.

Remember, building a solid investor relationship is like crafting a delicate dish—it requires finesse and careful seasoning.

So, be judicious with your questions, and let the flavors of your conversation simmer to perfection.


Congratulations you've reached the finish line!

Armed with a newfound understanding of the power of flipping the script, as the seeker of funding, it's time to embrace your role as the questioner, the one who assesses if the investor is truly the perfect match for your business journey.

Remember, it's not just about securing the funding but finding an investor who shares your vision, and values, and can provide more than just capital.

The human connection between you and your investor is a vital ingredient for long-term success.

From uncovering motivations and investment philosophies to navigating industry risks and communication expectations, your questions weave a tapestry of insights that guide your decision-making.

So, be judicious with your inquiries, timing them thoughtfully to build a genuine rapport.

Now, equipped with your arsenal of ten essential questions, you're ready to dance with potential investors, finding the perfect rhythm that propels your startup to new heights. Go forth, founders, and let the right questions pave the way to your entrepreneurial dreams!

Benjamin gave great tips to my start-up Blend for polishing and optimising my pitch deck, refreshing perspective. Recommend!