As I get ready for a new year with new possibilities, I’m being presented with a lot of new projects to play in. In the past, I’ve done the projects that picked me until someone dropped from exhaustion. Today, I’ve learned to ask a few key questions to see if a project is in alignment before I start.

21 Questions I Learned to Ask the Hard Way, so you can have it easier…

WHAT ARE THE 3-MONTH AND 1-YEAR GOALS FOR THIS PROJECT?

The more collaborators on a project means the more people with their own idea of what they want to do. Weak project leaders will add everyone’s goals to the pile, promise everyone what they want, and get none of it done. Ask for goals with timelines for the projects that you’re walking into. If the goals of the project haven’t been defined, ask how goals will be prioritized. If your project has more than 3 major goals, it’s unlikely to happen.

ASK TO SEE THE BUDGET.

It’s all well and good for project leaders to say that everyone’s ideas will be incorporated but the budget will tell you what’s actually possible with the resources available.

Are the project leaders saying that Black Lives Matter? Then look for the AntiRacism training budget. Are the project leaders saying that they want an equal number of male and female leaders? Then look at the staff budget and see if they can pay living wages to their female leaders.

Some leaders will say anything to get you on board but knowing where the money goes will tell you what the real priorities are.

FIND OUT WHO OWNS WHAT. FOR REAL.

No matter what collaborative structure the project leaders have chosen, at the end of the day someone(s) will own and direct what the organization does. Ask what legal entity they have chosen to operate as and…

ASK TO SEE THE INCORPORATION PAPERWORK

The incorporation paperwork will tell you legally who owns the project and what happens if something goes wacky. What you’ll want to know before you agree to collaborate is…

1. Who owns the project and its assets?

2. Who owns anything I create while working on this project?

3. Who is currently on the board and how do those people get switched out?

4. Who are the current managers of this project? If I’m being sexual harassed by a manager, who can I report it to? (This is a common snag in small companies when the only person to report harassment to is the person harassing you.)

5. Where does the liability fall if someone dies while on this project? (This is an extreme example of liability but will help you figure out if they have the proper insurance to cover the company.)

6. How can this company be unincorporated (dissolved) and what happens to the company assets afterwards?

HOW IS THIS PROJECT FUNDED?

The difference between a hobby and a company is funding.

How your project gets funded will determine A LOT. Whoever funds the project is your real customer. Meaning that no matter who are you trying to help, the majority of your energy will be spent on who gives you the money. (This is why most philanthropy fails to help the people who need it most.)

• If the project has no funding, get clear on how they plan to raise money and if you’ll be involved. Get clear on what happens if the money runs out. Do they own any work you’ve contributed if the project dies?

• If the project has a membership base, ask tough questions like–how many members do you have? How long do they remain members? How much are they paying?

• If the project is being funded personally by someone, know that the project will be subject to the whims of the person who funded it. No matter which collaborative structure you’ve chosen, I’ve never seen a management team tell the project funder no.

• If the project is being funded by an investment group or Venture Capitalist, know that it's unlikely your work will see the light of day. Your work is now only as good as it enriches your investors. What enriches your investors (like getting bought out by SalesForce) is often the opposite of what helps your customers.

ASK THE HARD QUESTIONS BEFORE YOU COMMIT

If the leaders that you’re interviewing have challenges answering these questions honestly and authentically, it’s a red flag 🚩How they answer these questions is a lot more important than what they say in my experience. If just being asked about any of these topics triggers the leader that you’re interviewing, just imagine what will happen when these scenarios actually come up.

• Can you tell me about the last time someone disagreed with your leadership style and how you handled it?

• Can you tell me about your last experience with sexual harassment in the community and how it was handled?

• What is your personal practice? How do you keep yourself aligned to lead?

• How do you know what’s yours to lead and what’s not yours?

• What was the most surprising thing you've learned in the AntiRacism training you’ve done? What AntiRacism training is planned for this project?

• Tell me about the last time two team members had a serious conflict and how you handled it.

• What would the last person who quit this project tell me about their experience?

• Can I speak to three people from previous companies you’ve managed?

• Who is sleeping with who on the team? How are sexual relationships handled within the company?

Again! Ask the tough questions now because conflict will come up later and you want to get a preview of how they will handle it.

BECOMING A CO-FOUNDER IS MORE COMPLICATED THAN GETTING MARRIED.

Choosing to co-own a company with someone(s) can be harder to get out of than a marriage. When you incorporate a company and declare yourself co-owners with others, you are stuck with those partners until you can sell (or give up) your ownership.

That doesn’t sound too hard at the beginning of a project when you assume everything will go well and your part of the company will be super valuable. But what happens when the company is out of money and you can’t find anyone to buy you out? You will have to carry ownership of this company until you give up your ownership or the entire company is dissolved. Until then, you will be financially and legally responsible for everything about that company, even if you’ve stopped being involved in the management. In my experience, getting out of a company can be more expensive and take more time than a divorce.

I now treat potential cofounders like potential spouses. I take my time getting to know them. I try small projects before committing to a big one. I invite them to do psychedelics with me and see how they do with intensity. As I told the UCLA Business School, you’re more likely to meet your best cofounder at AfrikaBurn doing LSD than business school.