25 Questions to Ask When Starting a Business with a Friend

Let’s paint a picture. You’re sitting around with your best friend—maybe you’ve just finished binge-watching a show, or you’re griping about how your jobs suck the life out of you.

One of you gets that lightbulb moment: “Why don’t we start our own business?” 

Who better to hustle with than someone who already knows you inside out? No awkward meetings or trying to figure out if you both hate pineapple on pizza (a real litmus test for friendships).

While it might sound like the dream team collab, you need to hit pause before diving into the venture with your buddy.

Get real with yourselves first and ask some tough questions. Trust me, you don’t want your business to tank and lose a friend in the process.

Why Should You Bother Asking Questions?

You might be thinking, “We’ve been friends for years; what could go wrong?”

Let me stop you right there. Friendship is great, but business? Whole different ball game.

In a friendship, you can brush off annoying quirks or the fact that your friend is always late for lunch. But in business? That “I’ll get to it later” attitude can mean missed deadlines, lost clients, or worse—bankruptcy.

You’ll be dealing with real money, real stress, and real consequences.

Asking the right questions upfront helps you see if you’re both on the same page—or if you’re about to step into a partnership built on quicksand.

It’s all about setting expectations. Sure, it’s going to feel weird having a serious convo with someone who knows every dumb thing you’ve done since high school, but these are the grown-up talks you have to have if you want your business and friendship to survive.

Questions to Ask Before Starting a Business with a Friend

If you’re not aligned with you’re friend when you start that venture, things are going to get real messy, real fast. Before you sign any paperwork, make sure you’ve hashed out these must-ask questions to ask when starting a business with a friend:

1. What’s the Vision for the Business?

This one’s huge. You and your friend might both be excited about starting a bakery, but are you on the same page about what kind of bakery?

Are you aiming for a small, local shop where you know every customer by name, or do you want to scale up and have a franchise in every major city? 

One of you might be thinking “cozy and charming,” while the other is dreaming of world domination. If you’re not in sync about the end goal, it’s only a matter of time before resentment sets in.

2. How Will You Divide Responsibilities?

Just because you’re great at brainstorming business ideas over drinks doesn’t mean you’re both going to be great at running the day-to-day.

What are you actually good at? And what’s your friend’s skill set? Be honest here—if one of you is all about the numbers and the other’s a marketing genius, fantastic.

But if you’re both trying to handle the same thing or, worse, avoiding tasks neither of you wants to do, the business will sink fast.

Make it crystal clear who’s responsible for what before things start slipping through the cracks.

3. How Do You Handle Conflict?

If you’re both super chill and non-confrontational, this might feel awkward, but you need to talk about it. Because guess what? Conflict is coming. It’s not a question of if—it’s when.

Will you tackle issues head-on? Or will one of you sulk and hope the other picks up on your passive-aggressive signals? The way you handle disagreements will make or break your partnership.

Do yourselves a favor and have a game plan for those inevitable moments when you want to strangle each other.

4. What Happens if One of Us Wants Out?

Not every business partnership lasts forever. Life happens—people grow, priorities shift. What happens if one of you wakes up one day and decides this whole thing isn’t for them anymore?

You need to establish an exit plan from day one.

Does the person leaving get bought out? Do they keep a percentage of the business? Figuring this out early will save you from a major fallout later.

5. What Are Our Financial Expectations?

Are you both on the same page about how much money you’re willing to invest upfront? What about how much you need to make to quit your day jobs? Do you have a timeline in mind for when you want to see profits?

If one of you is prepared to tighten their belt for the next two years, while the other expects to be sipping margaritas in the Bahamas by next summer, you’ve got a serious disconnect.

Get this sorted before you start draining your savings.

6. How Will We Make Decisions?

You’re not always going to agree on every little thing, and that’s fine. But how will you make decisions when you’re at a stalemate? Will you flip a coin? Bring in a third party?

You need a strategy for when both of you feel strongly about different directions.

Otherwise, you’re going to waste a lot of time arguing—or worse, not making decisions at all.

7. What’s Our Work Style?

Are you a morning person? Is your friend a night owl? These things matter more than you think.

If one of you is up at 6 a.m., ready to tackle the world, while the other doesn’t roll out of bed until noon, you’re going to run into problems.

You also need to figure out how you work best—do you like to plan everything down to the minute, or are you more of a “wing it” type?

These small differences can add up over time, so get clear on how you’ll work together efficiently.

8. What Are Our Strengths and Weaknesses?

You and your friend need to be brutally honest here. Just because you both think you’re super capable doesn’t mean you have all the skills to run a successful business.

Are you good at handling clients, but your friend is awful at social interaction? Is one of you amazing at organization while the other can’t even keep track of their own phone?

Identify what you both excel at and what you absolutely suck at, then divvy up responsibilities accordingly—or hire help if both of you are lacking in critical areas.

9. How Will We Handle Money?

Money—cue dramatic music. If you think starting a business with a friend is tough, wait until you’re trying to figure out how to split profits, pay yourselves, and reinvest into the business.

You need to have a clear understanding of how the finances are going to work. Are you splitting everything 50/50? Will one of you contribute more capital upfront and expect a bigger share later?

And let’s not even get started on paying yourself a salary—when? How much? Do you deserve it yet?

Have these conversations now, not after you’ve already started making money (or worse, losing it).

10. How Will We Handle Legal Issues?

This is the part where your brain says, “I’ll deal with that later,” but don’t.

Legal issues have a way of sneaking up on you like a bad hangover. You need to establish the legal structure of your business—are you forming a partnership, an LLC, or some other entity?

More importantly, what’s the legal agreement between you two? What if one of you accidentally signs a horrible contract or gets the company into legal hot water? You might love your friend, but that’s not going to protect you from lawsuits.

Be smart and get everything in writing, no matter how awkward it feels.

You don’t want to find out you’re personally liable for a bad business decision down the road.

11. Are We Prepared for the Sacrifices?

Running a business is like adopting a needy, 24/7 pet—it’s going to demand your time, energy, and attention, sometimes more than you bargained for. Are you and your friend both ready to sacrifice your weekends, evenings, and sleep to keep the business afloat? What happens when your friend wants to take a two-week vacation, but there’s a deadline looming? You need to talk about what you’re both willing to give up for the sake of the business. And remember, just because you’re besties doesn’t mean you’ll have the same level of commitment. Make sure you’re aligned on how much sweat (and tears) you’re willing to put in.

12. How Do We Define Success?

Success isn’t one-size-fits-all, and this is where things can get tricky.

What does success look like to you? Is it raking in cash? Is it having a flexible lifestyle? Is it growing the business into a massive enterprise, or are you happy keeping things small and manageable?

If your definition of success is different from your friend’s, you’re in for a world of tension down the road.

Sit down and define what “making it” means for both of you, so you can work toward the same goal without one of you feeling frustrated.

13. What Happens if One of Us Can’t Pull Our Weight?

Life happens—someone might get sick, have family issues, or hit a major burnout. What happens if one of you just can’t keep up with the work? Will you hire someone to help? Will the other partner pick up the slack?

And what if it’s not a temporary situation, but one partner consistently doesn’t pull their weight?

You need a plan for how to deal with this, whether that means adjusting roles, renegotiating equity, or—worst case scenario—letting someone go.

You love your friend, but if they’re not pulling their weight in the business, you need a way out.

14. How Will We Communicate?

This might seem like a no-brainer, but communication can be tricky. When you’re just friends, you don’t need to talk every day or give each other updates on your every move.

But in a business partnership, communication is everything. Will you have weekly check-ins? Will you email, call, or use Slack? How do you want to handle conflicts when they arise?

Having clear expectations for communication will keep things running smoothly and prevent small issues from festering into big problems.

15. What’s Our Plan for Growth?

Okay, so you’ve started your business—what’s next? How do you plan to scale? Are you thinking of expanding into new markets, hiring more staff, or launching new products? Or are you content with maintaining the status quo?

Having a clear plan for growth (or lack thereof) ensures that you both have realistic expectations for the future. If one of you wants to hustle for rapid expansion while the other is happy coasting, you’re going to clash.

Make sure you’re on the same page when it comes to how fast you want to grow.

16. What Are Our Personal Boundaries? 

When you’re starting a business with a friend, those personal boundaries can get blurry real fast. Will you be okay with late-night texts about work, or do you need a strict no-work-talk-on-weekends rule?

Is it okay to talk shop over some drinks, or do you need clear separation between business and pleasure? 

Establishing personal boundaries from the get-go will save your sanity and ensure that your friendship doesn’t dissolve into endless work talk.

17. What’s the Exit Strategy for the Business?

I know, it sounds pessimistic, but you need to think about how you’re going to get out before you even get in. What’s the long-term vision here? Do you plan on selling the business someday? Do you want to pass it down to your kids (assuming you’ll have them)? Or are you just looking to run it until you both burn out?

Having an exit strategy isn’t necessarily planning for failure; it’s being realistic.

If you don’t have a shared vision for how this all ends, things can get ugly when one of you wants out and the other wants to keep going. Make sure you’ve discussed every possible exit scenario.

18. How Will We Handle Failure?

Here’s the thing no one likes to talk about: failure. It’s not glamorous, but it happens more often than you think. Businesses fail all the time, especially startups.

If your business tanks—yes, I said “if,” because it’s a real possibility—what’s your plan? Are you going to split the losses and move on? Will one of you keep going while the other jumps ship?

Failure isn’t strictly financial; it’s also emotional. You need to know how your friend handles setbacks and whether you’ll both be able to look each other in the eye if things don’t work out.

Make a plan for how you’ll handle the fallout if everything goes sideways.

19. Are We Ready for the Emotional Rollercoaster?

One day, you’re on top of the world, and the next, you’re questioning why you ever thought this was a good idea. Are you and your friend ready for those highs and lows?

More importantly, can you deal with seeing each other stressed, anxious, and frustrated? Because that’s coming. You’ll see a side of your friend that you never saw before, and they’ll see the same in you.

How will you support each other emotionally?

Sometimes, the stress will bring out the worst in both of you. Make sure you’re ready for the emotional weight of it all.

20. What’s Our Plan for Delegating?

When it’s just you and your friend running the show, it’s tempting to think you’ll both do everything. But trying to split every task equally is a fast track to burnout and frustration.

Who’s handling marketing? Who’s dealing with customers? Who’s ordering office supplies because you’re down to one sad-looking stapler?

You need a clear plan for delegation. And no, “we’ll figure it out” isn’t a plan.

If you’re both trying to do the same thing, you’ll either step on each other’s toes or let important tasks slip through the cracks.

Have a sit-down and decide who’s owning what right from the start.

21. How Will We Adapt to Change?

Businesses change. Markets evolve. One minute you’re the hottest thing on the block, and the next, you’re scrambling to stay relevant.

How will you and your friend adapt to the inevitable changes that come with running a business? Will you be open to pivoting, or are you both too set in your ways?

Flexibility is key, and if one of you is resistant to change, it’s going to create friction.

Have a plan for how you’ll stay nimble and adjust to whatever life throws at you—whether it’s new competition, changing customer needs, or even shifts in your own priorities.

22. How Will We Protect Our Friendship?

Look, your friendship is the foundation of this whole thing, and if that crumbles, the business will probably follow.

So how are you going to protect it? Are you going to have “friend time” that’s strictly non-business? Will you promise to keep your personal lives separate from work?

This is one of those questions most people don’t think about until the friendship is already on life support.

Protecting your relationship means setting boundaries and making sure you don’t become business robots that forget why you were friends in the first place.

23. What Are Our Non-Negotiables?

Everyone has their limits, and you both need to lay them out. Are there things you absolutely won’t compromise on, no matter what?

Maybe your friend values creativity over profit, and you’re more bottom-line focused. That’s fine, but you need to know where each other stands.

Define your non-negotiables upfront—whether it’s how you treat customers, how much risk you’re willing to take, or what kind of culture you want to build.

When you know each other’s deal-breakers, it’s easier to avoid unnecessary conflict.

24. How Will We Handle Burnout?

Burnout is real, and if you think you’re immune to it, think again.

So, what’s the game plan when one of you hits that wall of exhaustion? Is it okay for your friend to take a break while you pick up the slack, or do you expect them to power through no matter what?

You need to have an honest conversation about what happens when one of you is running on fumes.

Maybe you can alternate taking time off or hire extra help when you both need a breather.

But you have to plan for it, or burnout will sneak up on you, and it won’t be pretty.

25. How Will We Handle Personal Drama?

Life is going to throw personal drama at you.

Whether it’s relationship issues, family stuff, or just general “I hate everything” days, personal problems will affect your business.

How will you handle it when one of you is going through a tough time and can’t focus 100%? Will you be understanding, or will it lead to resentment? 

You need to be prepared to support each other through the rough patches—without letting it destroy the business.

If you can’t be there for each other during life’s inevitable curveballs, you’re going to have a hard time making this partnership last.

Conclusion

Starting a business with your friend can be amazing. It can strengthen your bond, make work more fun, and create a shared sense of purpose. But it can also be a disaster waiting to happen if you don’t lay the groundwork upfront.

The key to making it work is brutal honesty—about your expectations, your weaknesses, your money, and even your potential exit strategies.

Friendship and business operate on two completely different wavelengths, and it’s easy to blur the lines between them.

If you don’t ask these hard questions now, you’ll be forced to confront them later when things get tough (and they will get tough).

By having these conversations early, you’re protecting your business and your friendship. And in all honesty, friendships like the one you have with your bestie are worth more than any business venture.

Now, if you’re ready to take the leap, get out a notepad, sit down with your friend, and start hashing out these questions.