When you’re starting a business venture with someone, there are a myriad of questions you need to be asking them to make sure you’re on the same page. “What is your educational background”, “Where do you see yourself in 5 years” or “why did you decide to become an entrepreneur” might be the first ones that pop into your mind, but unfortunately, the more important questions are a little more… uncomfortable. These questions are the ones you should certainly discuss before you find yourself in a position where you need to.

1. How comfortable are you with breaking laws?

Whether it be lying about your kid’s age at the zoo, rolling through a stop sign or committing high-level tax evasion, you need to make sure you know exactly where your partner stands before they do something you don’t agree with. You are putting a lot on the line, and now is not the time to skirt around delicate subjects.

There are tactful ways to approach this subject that won’t put you or your partner in such an uncomfortable position. Read on to find out how The Cofounders Hub will help you.

2. How do you feel about inter-office relationships?

Disregarding local laws and regulations, how does your cofounder actually feel about inter-company relationships? Are they okay with having employees congregating and forming romantic relationships, or is it something they prefer to keep separate from the business? Do they think there should be consequences for disobeying company policy? How about relationships between seniors and juniors, or supervisors and supervisees? And how about one of the cofounders and an employee?

It’s quite a sensitive subject, especially when it comes to your own roles, but it would be more detrimental to not have this conversation than to feel awkward for a few minutes. Make sure you can come to a compromise between both of your opinions before you find yourself in a situation where the issue has already occurred and you are caught unprepared.

3. Where do our shares go?

Wills and testaments, as well as founder insurance, need to be thoroughly discussed before anything is signed. You wouldn’t want to be caught off guard at a time like that. Before committing to anything, ask what the best-case scenario would be for your partner, and then talk to a lawyer about the possibility of making it happen. Remember to read the fine print in any investor relation document, they might want to take your shares if you or your cofounder lose your lives.

4. How do you feel about drugs and alcohol?

A good sense of what your cofounder does and does not partake in is sensible to have, and then it is up to you to find your threshold or dealbreakers. Also, consider what they think is acceptable in the office. It’s not uncommon for “hip” companies to allow their employees to partake in drinks on a Friday afternoon at the office, and having a conversation with your cofounder about how they feel about that will be beneficial. You then can create the company culture you agreed on with intentionality.

5. Is there anything I should be made aware of?

Crime, arrests, illegal activity that was undetected… Is there anything you should know about and be prepared for in case something goes wrong? Ask around and you’ll hear a story or two of a founder whose cofounder was accused of an illegal activity that the founder had no idea about. You’re definitely not in this business to become a cautionary tale!

Don’t forget to extend the question to your cofounder’s immediate family and close friends. Anything that could affect your cofounder could also affect the business, and in turn, you.

6. Is there anything you feel strongly about that might affect the business?

Social causes, political views, conspiracy theories… This is the time you should ask your cofounder if they have any radical beliefs, or even just causes that they would put everything on the line for. Just like a lot of the previous questions in this post, you don’t want to be caught by surprise by these aspects of your cofounder’s personality.

There are other ways to test for personality, belief and behaviour discordance between partners…

7. Now, would you put that in writing?

The Cofounder’s Hub offers you three especially nifty tools that help navigate these awkward conversations and protect both partners in a mutual bond of trust and accountability. Find out what contracts you should sign, what behaviours to look out for from your partner and yourself, as well as a complete list of questions just like these ones that will make sure you’re prepared for anything the entrepreneurial journey may throw at you.