How to be the Best Board Observer
Non-Obvious Advice from Seven Series A Founders
By Jessica Li
Many investors step into their first roles as board observers as they reach Senior Associate and Principal level. While board observers don’t have as much say in a company’s governance as full board members do, they can still add value and offer support in a number of other ways.
As a firm that specializes in placing top VC talent, we often have candid conversations with rising investors about the challenges they face as first-time board observers. For instance, we heard from a number of investors that they struggled to add value to founders and felt intimidated in their first board meetings next to board members who often had decades more years of experience.
So, we went directly to the source — founders themselves. We confidentially interviewed 7 Series A Enterprise and Consumer startup CEOs to ask what they value most in their board observers. We asked them to identify the most memorable, valuable, and meaningful support they’ve received from board observers. Here’s what they shared:
Make connections
Lean into the advantages you have as an investor earlier in your career. Oftentimes, board observers are younger and more on the ground relative to board members, so they can frequently be more helpful for facilitating thoughtful introductions. For example, the founder of a Series A talent technology company shared that her board observers connected her team with personal friends of hers working at companies that fit the founder’s ideal customer profile.
Board observers can also leverage their healthy investor network to help build momentum for a founder’s next round. For example, the founder of a Series A social commerce company shared that one of his board observers made dozens of introductions for them as they geared up for their Series A raise.
Sales introductions can be game changing for startups. A Series A e-commerce startup founder shared that his board observer helped facilitate key customer introductions that in part solved their cold start, chicken and egg problem. The founder shared,
“When we first launched, we really struggled to find big eCommerce brands to partner with. All we needed was one win, one brand to believe in us. Just having one big logo on our website would be a real game changer and make all other sales conversations go much more easily. Our board observer made a critical introduction that helped us get in touch with a major eCommerce brand and eventually win them over as a partner, which opened tons of doors for us. Even when those introductions didn’t convert into sales opportunities, the conversations were valuable for us in coming closer to finding product-market fit and narrowing which prospects to prioritize.”
Going even further, according to one founder of a Series A sales enablement software company, “introductions to great prospects is the single most helpful thing board observers can do for early-stage enterprise companies.”
Roll up your sleeves
Board observers can function almost as part-time team members rather than as typical investors. Instead of being a seemingly inaccessible person who only connects with the company four times a year, board observers can be a sort of part-time Chief of Staff to the founder, taking work off their plate. For example, the founder of a Series A data privacy company shared that his board observer would often ask him what he would do with just a few extra hours of the day or week, and she would then take those tasks off his plate whenever possible. She did everything from mocking up wireframes in Figma to putting together ad copy to cold emailing prospects to conducting first-round phone screens with candidates. While this example might be extreme, it illustrates how creative board observers can get when it comes to rolling up their sleeves and working alongside founders they support.
Another board observer sat down with the founder of a Series A hardware company to map out every part of her company. In this way, they collaboratively identified the biggest areas of weakness. They realized that the biggest bottleneck was performance marketing, which then led the founder to be more focused in her hiring efforts and in strategically allocating her own time and capital.
Similarly, the founder of a Series A talent technology startup shared:
“My board observer often offered to do special projects for me, even without my asking. We were exploring a potential pivot, and our board member did great work in putting together a market map for the new space we wanted to go after.”
Board members with technical backgrounds can find ways to be even more hands-on and granular with their company-building support. For example, the founder of a Series A e-commerce company shared that one of his board observers joined their team’s GitHub to help track projects and generally keep morale high in the middle of difficult sprints. The board observer also helped identify how to reduce technical debt and prioritize competing projects.
On the product front, board observers can help by testing and QA-ing the product before a big launch or release. They can conduct user interviews and customer research by running surveys, analyzing data, conducting interviews, organizing focus groups, reading industry reports, etc. Those are all valuable, but time-consuming tasks where founders typically welcome the support.
The trick is to lean into your specific superpowers that you might’ve honed previously as an operator or investor. Whether you previously worked in marketing or product or learned financial planning and analysis in your last role, identify your particular superpower and offer it up to founders as needed.
Board observers themselves can also help founders be more intentional about the culture of the companies they’re building. With a bird’s eye view of the business, board observers can offer unique ways to foster an intentional culture. For example, the founder of a Series A sales enablement software company shared that his board observers had helped him find an Airbnb for a team retreat and for their next sprint to build more camaraderie among new team members.
Manage the board
Board observers can take a more active role in helping founders prepare for board meetings. While they may not always show it, board meetings are very nerve wracking experiences for entrepreneurs. The founder of a Series A fintech company shared:
“One of our board observers took the time to help share feedback on our slides, even get hands on and literally work on some of the slides, and help me think through how I should prioritize ‘asks’ of board members. It was super helpful to get an investor view on all of that.”
On the flip side, board members themselves are often quite busy and can inadvertently forget to complete deliverables that were agreed upon in the prior board meeting. Board observers can help leverage their organization competencies and bandwidth to ensure board members follow through on action items and actually deliver on their promises. Board observers can help hold everyone and their board members accountable on behalf of the founders.
Founders put in tons of time to prepare for board meetings, but unfortunately, not all board members take the time to read through the board deck and other shared materials beforehand. As a board observer, show you care. One Series A talent technology startup founder explained how much it meant to her that her board observer took the time to comment on each page of her board deck.
Our founder respondents shared that finding and connecting with board observers who are truly passionate about what they’re building was incredibly meaningful. By showing genuine excitement for what the founder is building and what they’ve achieved each quarter, you provide much needed energy for the founder and their team heading into and during the board meeting itself.
Build the team
Hiring is a key area that board observers can support in a more hands-on way. For example, the founder of a Series A hardware company shared that one of her board observers asked her to put together a “dream list of hires” for each of the company’s open roles. He then offered to meet with each of the people on the dream list (if they were willing) to help her further build the relationship with and close those candidates.
Board observers can support in every part of the hiring funnel. For example, the founder of a Series A e-commerce startup shared:
“One board observer built talent lists. He basically went through and put together a spreadsheet of LinkedIns for each of my open roles and then cold reached out to all of the people we wanted. It was amazing! He also then did first and second round phone screens to vet those candidates, which saved us a ton of time.”
Offer emotional support
Founders have one of the most challenging jobs in the world. Building a company is a lonely endeavor— founders are often unable to share their true concerns and feelings with their team members. Being so transparent with board members can feel intimidating as well. Board observers can be the happy medium: someone who has enough context on the company to truly listen and understand, but someone who is more relatable and accessible for the founder to talk to and be honest with through both the ups and especially the downs.
It may seem simple, but listening can be one of the most meaningful things board observers can do for founders. As one founder of a Series A fintech company put it,
“I appreciate just having the space to verbalize my thoughts and hear someone else’s initial reactions to and framing of them.”
Help hone the story
Board observers can provide invaluable coaching for founders on how to frame their vision and hone their story so it resonates with investors, potential hires, and customers. For example, when the founder of a Series A deep tech company went out to fundraise, she noticed that many investors she was pitching to had trouble understanding and getting excited about what she was building. She notes,
“I told our board observer about this since I was too embarrassed to share that with our board member. Our board observer then hopped on a call with me immediately to workshop my presentation of the mission and vision.”
Workshopping a startup’s “story” is one of the most helpful ways to add value as a board observer.
The founders we interviewed emphasized one crucial insight: board observers don’t have as much information on the business as founders do. As a result, they shouldn’t see themselves as business decision-makers or providers of definitive advice. Rather, the best thing a board observer can do is to just be there for the founder. Being there can take many forms as outlined above, but at its core, being there means being reliable, accountable, and ready to support in both the good times and the bad.
