Cofounder courtship: How to find the right mate—for your startup

How could a cofounder balance your skills and experience? For example, if you are a technologist, but lack management or operating skills (marketing, sales, etc.), you may benefit from a more seasoned business leader as cofounder who has seen the movie before. While many operating skills can be learned, early-stage founders may underestimate how critical these skills early on—rookie mistakes can set back (or kill) a business before it’s barely out of the gate. Read Khalid Halim’s thoughts on Hypergrowth and the Law of Startup Physics for more on this point.

Conversely, expertise and experience can be additive to the business without a cofounder title and compensation. Unless you are doing hard science that is your core business, building a business that is technology-forward or relies on tech to some degree is not nearly as hard as it once was. Having a strong first-hire who is technical can suffice; the same holds for someone with strong sales, marketing, or other operational skills.

Is domain expertise critical for your venture? Unless you are already the expert in the particular field your venture intends to address, you may need a cofounder with domain specific expertise. Having domain expertise will not only inform the product strategy, but will also help the venture gain credibility in the market and potentially open doors on the sales side. Investors may expect or even require there be a domain expert on the cofounding team, but similar to the point above, you may also be well served with a first hire or even an adviser who could serve you in this way versus a cofounder.

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Most importantly, ask yourself whether you value partnership, shared risk, and collaboration with others. It can be great to have someone to brainstorm with, share the workload, and to commiserate with during your journey, but having cofounders—like a committed personal partnership—is also a big test of your ability to be vulnerable, handle conflict, and compromise. There will be many times your cofounding team will disagree on things—from product and hiring decisions to operating procedures and a fundraising strategy—and how you process these decisions together is fundamental to a healthy cofounding relationship.

Self-awareness, a willingness to lean into conflict, and ability to thrive in ambiguous situations will be critical in a cofounding relationship. If you question whether you are up for sharing these experiences with one or more cofounders, you may need to do some introspective work before taking on a cofounder or, perhaps, go it alone.

Anyone thinking about having a cofounder must go beyond the skills and experience aspects and consider the fact that they are entering into a deep, personal relationship. Whether it’s because you couldn’t find “the one” and time is of the essence or because you are self-aware enough to know you are better off going it alone, taking the solo route is perfectly doable by rounding out your team with necessary skills and expertise. You might also consider a second in command (COO, CTO, etc.) who plays a key role in the business without the official cofounder title and compensation. These individuals can still receive founding team worthy equity grants and, in earlier stage businesses could be anointed as “co-founder” down the road if the relationship blossoms over time.

The cofounder courtship

If you’ve decided that you really want and/or need a cofounder, you’ve basically decided to seek a mate for a long-term partnership. Just like a personal relationship may result in children, big financial decisions (like buying a house), running a household, etc., a cofounding relationship will force you to commit to how you will nurture employees, manage finances, and run your business.

There are big decisions to make: “How will we educate our kids?” is similar to “what kind of company culture will we have?” There are philosophies on which to reach alignment: “Where will we raise our family?” is similar to “will we have a home office or remote-friendly work environment?”

You can’t have a few coffee meetings with a prospective co-founder to discover how you will answer these deeper questions. It’s a courtship and despite the urgency you may have to get going with the venture so you can raise money, hire people, etc., I can’t emphasize enough how important it is to nurture these prospective relationships.

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Here are a few suggestions on how to court your cofounder(s):

Conduct a listening tour by meeting other startup cofounders. Talk with them about their own courtship process. Ask if there were questions they wish they had asked and hurdles they had to overcome early in their relationship. Even the greatest cofounding teams have war stories about stressful situations in their relationships and what they learned from these experiences.

Using insights from the listening tour, along with your personal preferences, write a cofounder job description (JD) and include experience, skills, and the ideal, softer, characteristics you seek in this person. If you already have someone in mind, try to stay objective and not write this JD to ensure they can fill the role (an act of confirmation bias). Use this as your guide as you meet prospective cofounders and adjust as you go. It’s very likely that the more prospects you meet, the more tweaks you’ll make to that JD and finding “the one.”

NOTE: If more than two of you are thinking about becoming cofounders, do the JD method as a “diverge-converge” exercise. Discuss potential roles each may fill and have each of you, independently (diverge) write the optimal cofounder JDs for each role. Once each has taken a stab at this exercise on their own, share these JDs with each other (converge) and discuss where you were all coming from for each role. Not only will this better define each role, but it will allow you and your prospective co-founders to expose perceptions and expectations of each other and how the leadership of the business will play out.

Experienced hiring managers know that it is rare they’ll hire the first candidate they interview for a newly created role because they may not be clear on the right fit for the role until they’ve met a few types of candidates. The same holds for co-founders. You may have to test a few potential cofounder candidates before inking a cofounder agreement.

Try to meet at least a half-dozen people who may solve for the gaps you are hoping to fill (expertise, experience, chemistry, etc.). Yes, this may mean you are “dating more than one person at a time,” but you’ll be far clearer about fit through this series of conversations.

NOTE: Finding a half-dozen candidates may not be easy. Tap into your network, ask prospective investors, former professors, etc. and tell them what you’re looking for. Share the JD. Attend conferences, talks etc. and be clear you are in the market for a cofounder. YC also released a cofounder matching tool that may be helpful.

Test the relationship beyond coffee chats and dinners. As noted in the Huberman podcast, relationships are truly tested when the parties engage in experiences that allow them to see more dimensions of their personalities. For example, go on a road trip or partake in an activity that neither of you have done before. See how each of you make decisions together like where to eat lunch or which trail to hike. Even a game of mini golf at a course neither of you have visited or playing a video game together can test how you collaborate or handle competition. You might also consider working on a start-up related project together to see how that feels, such as co-creating a pitch deck or conducting customer interviews together.

NOTE: If you are considering a first-time cofounding relationship with someone you’ve worked with at a company in the past, this doesn’t give you a “pass” to skip this part of the process. Cofounding a business with a former coworker is like going from dating to living together. You are sharing responsibilities you likely did not have when you were colleagues at a business where someone else was accountable for the overall successes and failures and, likely, making more strategic decisions than you were privy to.

Have vulnerable conversations. One of the most popular sessions in my course at HBS is the discussion around one’s relationship with money. Most adults have very different perspectives on money and typically this is rooted in deep family or personal experiences, sometimes starting in early childhood. A parent losing a job, having to work at a young age to support family, credit card debt, anxiety about school loans, etc. Understanding how you and your cofounder think about money will give you a lot of perspective when it comes time to raise capital, price your product, pay employees, etc.

Similarly, it’s important to talk about any peak moments in past jobs, school, etc. that inform your attitudes about leadership, culture and how products are designed and built. While these conversations may feel very uncomfortable, it’s a step toward a solid working foundation in what will almost surely be a roller coaster of a journey together.

Being able to have these conversations also tests how you’ll handle and support each other during conflict and stressful moments. You will have context and better understand where you are each coming from. Most importantly, these types of conversations don’t stop once you agree to be cofounders; they should be ongoing throughout the life of your venture as each cofounder and the relationship matures.

Finally, I recommend that prospective cofounders meet each other’s partners/families/BFFs. Not only does this further uncover the broader context of who these individuals are, but it also helps these important people in your lives understand this new relationship you may be entering. So, when you are up until 2 a.m. Slacking with your cofounder about the upcoming pitch or how to deal with a customer issue, they know who that person is and how they are partnered with you.

NOTE: For those considering cofounders who ARE your partner/family member/BFF, I encourage you to enter with a mindset around taking a personal partnership from no kids to four kids. It brings the relationship to a whole new level. This can be an incredibly rewarding experience for you, but it can also test the relationship to the max. While you probably know this person and you probably trust each other better than strangers, there’s likely baggage that can create more emotion and triggers around certain issues than the average partnership.

I have worked with incredibly endearing and high performing cofounding teams made up of siblings, married couples, and BFFs, but I have also seen these types of cofounding teams erode due to irreparable events rooted in their personal history. Do not take this choice lightly. Consider getting a coach early on who specializes in working with cofounders who also have personal history together. I guarantee you will not be able to put your personal stuff in a box outside your business. Personal tensions will come up—either overtly or subtly—and having the support to work through it will be crucial to your long-term success.

Also read: Founders' Corner: What old and young entrepreneurs can learn from each other

One cannot rush the cofounder courtship process. The most successful cofounding relationships I’ve seen inevitably end up being far more than coworkers. They are practically family and while that means potentially more emotions are at stake, it’s their mutual understanding and deep respect for each other that allows them to traverse this often treacherous journey. They have mutual trust and are committed to ensuring the success of their business, together.

Julia Austin is a senior lecturer at Harvard Business School's Rock Center for Entrepreneurship. She's also a startup adviser and angel investor. This article originally appeared on her blog, Being FA and Other Ponderings.