A business partnership is like a marriage. Embrace the courtship.

To cofound or not to cofound? It’s a complicated question many entrepreneurs face, and the search for a partner can feel more like a game of roulette than a calculated business decision. Do you need a cofounder to succeed? Not necessarily. But if you want to build a dynamic duo, there are several factors to consider.
Elizabeth, if you were located in Denver, I’d have you sit down for coffee with Andrew Schremp, a friend of mine and the founder and CEO of Health Sqyre, a patient-oriented online marketplace for medical equipment. He went through a valuable breakup with a potential cofounder—and I say “valuable” because it occurred before anything permanent was arranged. Use his lessons to guide you. “With the long hours it takes to get a startup off the ground, you’ll spend more time with your cofounder than your spouse,” Schremp says. “Create criteria, be patient, and do not cut corners.” And consider your weaknesses.
“So much of finding a cofounder is understanding where you’re not strong,” says Cameron Herold, founder of the COO Alliance, a company that develops and guides “second-in-command” leaders. If you’re a strategy person, find someone to focus on execution. If you’re introverted, find an extrovert. “A cofounder is the yin to your yang,” Herold adds. “They should be doing all the extremely important stuff that drains you of energy.”
Schremp suggests starting with your own network. Talk to friends and acquaintances with successful businesses and see if they would recommend anyone. “Six degrees of separation” is in full effect here—you’re unlikely to find the best person for the job within your inner circle, but you’re probably one or two steps from prime candidates. Referrals streamline the process, helping you avoid folks who will waste your time.
Specify three critical criteria—for example, you could want someone who’s great on small teams, focused on tech, and comfortable with higher equity and a lower salary—and use them to develop an early list of candidates. Then dig deep. Start with three to five references for each candidate, and ask every question imaginable, from work style to conflict resolution to simple personality traits. Basic questions with no apparent correct answer— Does Jane like long or short meetings? Is Mark a beer drinker? How much time does Kevin spend on his personal health?—can provide a window into what it would be like to spend every day with this person. “Intelligence is the most overrated cofounder trait,” Herold says. “If they’re not a good match with the founder, it just won’t work.”
After you’ve zeroed in on your top choice, it’s a matter of trust. Schremp recommends a minimum six-week work arrangement. Have the candidate sign a proprietary information and inventions agreement (so you can sleep soundly), then get to work and see if it’s a fit. Sure, there will be a honeymoon period, but if there are cracks in the foundation, you’ll see them quickly.
Are there any guarantees? In business, never. But if you follow these steps, you’ll remove your own selection bias and find the best person for your company. After all, it’s one of the biggest decisions you’ll make. “Any cofounder is going to be a boulder that you drop into a pond,” Herold says. “It’s going to make waves, so you have to make sure the ripples are good.”