How to communicate effectively with board members

Lessons from operators and board members at a16z, CRV, Founders Fund, Patreon, Anduril, Winnie, Notejoy, Redfin, SurveyMonkey, Ticketmaster, Slack, Honeycomb, and more!

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Q: How do I communicate effectively with board members?

I’ve been an operator for 20 years and a board member for a few. As an operator I had a front-row seat in working directly with several boards, including Lyft, WyzAnt, Patreon, and Imperfect Foods. Most interactions with boards live and die by effective communication, shared expectations and clear asks. I’ve seen this done well and I’ve seen it done… not so well.

And it turns out that I’m not the only one.

I gathered diverse perspectives from more than a dozen different board members, operators, or operators-turned-board members to help answer the question posed above: how do you communicate effectively with board members? A lot of the feedback and advice centered around the board meeting itself, but there is also plenty of advice around frequency and communications outside of the board meeting.

Thanks to Andrew Chen from a16z, Sara Mauskopf from Winnie, Saar Gur from CRV, Trae Stephens from Founders Fund and Anduril, Ada Chen Rehki from Notejoy, Tyler Palmer from Patreon, Selina Tobaccowala from Homeboost, Lobby Capital, Redfin, Survey Monkey and Ticketmaster, Kelly Watkins from Honeycomb and Slack and so many more people whose perspectives shaped this newsletter.

There are eight themes that emerged across all of my conversations about effective board communication as well as my own lived experiences. They are:

1. Balanced and Transparent Reporting

2. Diverse Executive Involvement

3. Strategic Focus and KPI Selection

4. Clear Communication Objectives and Preparation

5. Regular and Consistent Updates

6. Conciseness and Focus

7. Explicit Asks and Engagement

8. Building Relationships and Trust

Before addressing these themes it’s important to establish the role and purpose of a board of directors. I thought Saar Gur, general partner at CRV, summed this up quite nicely:

“Boards serve multiple purposes. They are supposed to exist to be a form of governance for the company, but the governance part (voting and approvals) is often less than 5 minutes of a startup board [meeting]. The other purpose is to bring board members up to speed on their investment (monitoring) and I find a lot of young founders spend most of their time just updating the board on what happened (reporting). The final purpose is strategy. The strategic and value-add part of board meetings requires work by the founder to drive the agenda and clarify what is helpful to discuss with the board given the people involved.”

Having established the role of the board, let’s dive into the themes!

#1 - Balanced and Transparent Reporting

A long time ago I had a boss who told me “bad news doesn’t get better.” I have since adopted this philosophy and it’s a key part of my user manual. It applies equally well to working with board members.

Your board is part of your team; so give it to them straight. Not doing this is one of the primary reasons that boards lose confidence in the founder/CEO. 

Andrew Chen, of Andreessen Horowitz (a16z),

“I like when decks start out with a section that lays out: here is what’s going well and here is what’s not going well. It sets the tone of the discussion as good and bad and not just a hype machine.”

Tyler Palmer, fmr SVP of Ops at Patreon; board member at Harbour,

“Always share the good, the bad, and the uncertain. Startups are hard. Your board knows it. Be transparent about what is working, what is not working, and what you are still trying to form an opinion on."

Kelly Watkins, BoD at Honeycomb, former CEO Abstract and VP Global Marketing at Slack,

“Bring the good, bad, and the ugly to your board and in a timely fashion. Your board is invested in your success, has the resources and network to help, and has a responsibility to shareholders for the outcome of the business. Hiding things from your board or only sharing wins doesn't benefit anyone - especially not you.

Companies love to share up and to the right numbers with the board, or to sandbag particular numbers so performance looks better than it is in actuality. I don't think this helps anyone. Your board will find out the facts eventually and hiding things from them prevents them from helping. An example here would be looking at the metrics you share with your board and giving them an honest assessment of progress against goals. If a particular number is trending downward, but has not impacted revenue, you should still share these details.”

The board that I sit on currently, Table22, has a team who does a great job with this. The founder and CEO, Sam, begins every board meeting with a “State of the Union” and has a single slide that provides an at-a-glance “top” and “bottom” of the quarter. It sets the tone for the meeting and encourages candid discussion.

You can download this template here.

The main takeaway: share all progress and setbacks with your board; no matter how uncomfortable. They’ll understand and appreciate the transparency.

#2 - Diverse Executive Involvement

As an operator I always enjoyed the chance to interact, communicate and seek specific feedback from the board – both in our scheduled, quarterly board meetings and ad-hoc. Turns out, board members like it too. It gives them a view into the leadership across the rest of the organization.

Andrew Chen,

“I like when the executives are able to present and prepare their section so that I’m able to get a sense of the leader. How is our marketing team doing? How is our technology team doing? Otherwise when the CEO presents all of it then there’s a sameness to it that makes it hard to evaluate.”

Tyler Palmer likes smaller, more frequent interactions between board members and the leaders of the company. He suggested breaking into smaller groups comprised of specific leaders and board members/

“When appropriate, break your board into smaller groups. Play to their individual strengths. Be open to breakout groups in between board meetings to deep dive on subjects where members have particular strengths and expertise.”

The main takeaway: this isn’t just the CEO show. It’s important to have your other leaders communicate progress and strategy in their areas of ownership. Encourage them to build relationships with board members.

#3 - Strategic Focus and KPI Selection

Your board needs to be engaged in what the most important KPIs for your business are, why you chose them and how that relates to your strategy. But more importantly, you need to decide if these warrant regular discussion with the board or not. Usually the answer is “not” and the metrics can be reviewed separately from the very valuable live time. Remember, a good rule of thumb is to ask yourself whether it could’ve been an email!

Tyler Palmer,

“Ensure every member of your board deeply understands the high level strategy of the company, and knows the top KPIs the company is driving towards. Determine the right cadence for reporting progress on said KPIs.”

Saar Gur suggests to consider separating the “reporting” aspects of your communications from the meeting itself, especially if it can be consumed without much commentary:

“Is this just reporting data and downloading information to the board on key metrics/progress?  This may or may not require much discussion.   For example, here are a bunch of stats or dashboards on how we measure the business and some updates that are helpful to be up to speed on the business. Often these can be sent in advance and the team may just want to drill in on a few of the key metrics/updates or send questions in advance. It helps to highlight the few things that your board members should pay attention to: did you miss plan and why? Were expenses higher or lower than planned and why? Did you lose or win a big customer… and why?”

Andrew Chen, a former operator himself, likes discussing KPIs but wants to make sure that they’re the right ones; the ones that move your strategy forward:

“I like it when there’s KPI‘s to discuss, but people tend to pick them almost too easily without discussing if they are the right metrics. Picking metrics is like picking your strategy.”

Main takeaway: choose the right KPIs that show progress towards your strategy, then share them regularly (monthly) with your board. Avoid spending too much time on them at the board meetings by identifying what you want your board members to pay attention to.

#4 - Clear Communication Objectives and Preparation

Well prepared communications with clear objectives and a well-prepared board meeting was a major theme across all of my conversations. Some founders have even started eliminating decks in favor of board memos. I’m increasingly a fan of this approach—if you use writing and memos internally to communicate then why not with your board?

Saar Gur, recommends being clear about the purpose of each communication and each of the parts of a board meeting.

“One purpose of communication could be recommendations. Often a team is moving forward on some decisions and may not know if the board has any strong opinions, advice or connections. I think it’s helpful for the team to bring the board up to speed with how they are thinking through these decisions and planning to move forward. Advice is the last purpose. I find that highlighting the big strategic questions that the team is wrestling with and/or really wants board feedback on is really helpful. Many communications don’t have a clear set of questions or topics that make it clear what the CEO hopes to get out of the meeting. If I had to pick one thing I would emphasize this point. The CEO needs to communicate clearly the strategic discussions that they want to have with the board.”

Tyler Palmer,

“Be clear on what you’re seeking in each interaction/memo/meeting. Let the board know when you want high level feedback, detailed feedback, opinions on upcoming decisions, or if content is just an information download.”

Selina Tobaccowala—founder/CEO of Homeboost, board member at Redfin, former President and CTO of SurveyMonkey—recommends highlighting key questions in your communications.

“At the top of the materials have a "Key Questions". If you are gathering people and spending their time it shouldn't be an update but a real place to get some thoughts or feedback.”

Main takeaway: regardless of format make sure you’re clear about why you’re sending a communication and what the need is. Provide your board with advanced reading material and specific focus areas.

#5 - Regular and Consistent Updates 

Update early, update often… and don’t wait for the board meeting. This feedback came through loud and clear from both operators and board members alike. At Patreon, Jack used to send an end-of-week update to the board. At Table22 I have a monthly call with the founder in addition to the quarterly board meetings; we also exchange text messages throughout the month. Some of the companies I’ve invested in send monthly communications. When those stop or become less frequent I know something is up and it’s usually not good. 

Sara Mauskopf, co-founder and CEO of Winnie, says consistent schedules are also helpful for managing your time as a CEO.

“Maintain a schedule for communication so your board knows what to expect. I send monthly investor updates and then hold quarterly board meetings. Board decks always get sent out a week in advance of the meeting and monthly updates always get sent out in the first half of the month. This regular communication ends up saving me time because my board just waits for the next update rather than hitting me up with a bunch of questions mid-cycle (unless there's an emergency or something timely). Also by keeping my board informed, they know how to be the most helpful to me and the company.”

Kelly Watkins is an advocate for advance sharing of information and suggests a Slack channel for easy and frequent communication:

“Avoid performative management in board meetings and instead engage your board in productive debate and conversation. Send slides and other materials well in advance, and even consider drafting a long-form memo instead of slides that provide updates, progress, and setbacks. It helps to  establish context prior to meetings. Use meeting time to instead dig into meatier topics. I also think it can be super useful to have a private Slack Channel for your board - either just with you as the CEO or with you plus a few key team members. This makes it easy to share anecdotes and data. I also think it's wise to have phone numbers for your board so you can text them updates or ask for help directly.”

Trae Stephens of Founders Fund and Anduril is a proponent of consistency in format to aid in establishing trends:

“This normally boils down to quarterly, but my preference is to see information in the same format from quarter to quarter so I can track performance towards metrics over time.  If the format is going to change, point out where it has changed and address the ‘why’ behind it.”

Tyler Palmer highlights the importance of frequency in building trust:

“First note is to just do it. Do it frequently so your board is not in the dark. The more context your board has, the more helpful their perspectives will be when the time comes for help. Regular communication builds trust. When sending materials to a board for a meeting, send them well in advance. This gives you the best chance of having everyone arrive at the board meeting prepared and having read the materials. I recommend sending materials 7-10 days in advance of the meeting, so that the material is consumed, and still fresh in their minds.”

One thing to remember is that board members (and company executives for that matter) are very busy. Consistency in format helps to eliminate a large part of mental overhead for everyone. If Steve Jobs could wear a turtleneck and jeans every day you can maintain a consistent format for board communications.

As I mentioned above, when that consistency starts to waver it’s a signal to me that something is going on at the company and it’s probably not very good.

Main takeaway: Regular, consistent communication is key and it doesn’t mean just at the board meeting. Look for other ways to create a cadence of communication with your board; it’ll save everyone time in the long-run.

#6 - Conciseness and Focus

There is nothing quite so devastating when communicating with your board then over-doing the length of the communication. I’m a big believer in bottom-line communication, which is why I like the “State of the Union” format above.

Trae Stephens,

“Don't overdo it. Keep updates as concise and focused as possible. I don't want a 100 slide board deck or a 35 page CEO letter. It is easy to hide issues behind walls of text.”

Ada Chen Rehki,

“Avoid readouts and status updates - avoid boardroom theater where it’s just a series of presentations. Send a pre-read if that’s the case and design the agenda around decisions you’re planning to make.”

Main takeaway: keep it simple and focused. Everyone is busy and this helps you and the board maximize the effectiveness of time spent creating and consuming updates.

#7 - Explicit Asks and Engagement

It’s important to know your board members skills and abilities. Are they a former operator with experience building marketing strategy? Can they help you vet and close a candidate? Do they know all the proper benchmarks for net revenue retention? These are just a few of the myriad ways that you can engage with your board outside of the quarterly meeting.

Ada Chen Rehki,

“Understand where you will get leverage from each board member and put them to work.”

This isn’t always something that comes easy to leaders though, so you have to work at it. Your board members want to help and if you’re not giving them specific guidance they might try to help in ways that aren’t all that helpful!

Sara Mauskopf,

“Always try to have an ask. I'm not great at this but I really try hard not to send investor updates or board decks without some ask or way to help. I've found that people really want to be helpful and so I should give them the way they can be most helpful (even if it's just ‘read this and give me feedback’). If we're really heads down and don't want any help I will try to be direct about that too. I've just found it's better to be explicit rather than expect people to read your mind or know exactly what the company needs right now.”

At the end of the last Table22 board meeting the CEO said, “I’m going to send you all a specific set of people and I want to know if you can help us get introduced to them.” He followed up with a spreadsheet, tagged us in different rows where he thought we could be helpful, and even provided some context on the reason for the introduction. As a busy board member this provided great clarity and direction for me and I was able to pull it directly into my “to-do” list.

I’ve also spent time with company leaders to help provide input on financial reporting and product strategy. But it wouldn’t have happened without an explicit ask and the leaders knowing where I’m able to help.

This is why Kelly Watkins advocates for bringing on independent board members:

“Don't wait too long to bring on an independent board member who has strong operational expertise. VC board members are hugely helpful, but having an operator's perspective around the table can add essential nuance to conversations.”

And Selina Tobaccowala is an advocate for having key advisors who aren’t necessarily on the board (but could be in the future):

“In addition to your board and if you are private, have a set of key advisors you can also turn to that you keep abreast of the company. This will help if you want to add independents over time but also gives you some alternate viewpoints.”

Finally, Tyler Palmer had an interesting perspective on how to keep your board engaged:

“Keep it fun and engaging whenever you can. Tell compelling stories, share the interesting and fun wins regularly. You want to keep your board engaged and excited about your company. They are busy people, and have a lot going on across several companies. The more excitement they feel towards your company, the more value they will deliver.”

Main takeaway: know your board members’ expertise and abilities. Make specific asks in each communication that leverage those strengths. Keep it fun and make it enjoyable for them to help you.

#8 - Building Relationships and Trust

Everyone I spoke with emphasized the importance of relationship building and trust through your regular communication with the board. Each of the above themes should help with that—from transparency and consistency to explicit asks and focus. 

There were some good suggestions that emerged from my conversations on how you can build relationships in addition to doing all of the above. Most involved discussion outside of the board meeting.

Ada Chen Rekhi, 

“Build meaningful relationships with board members around the meetings. Building up that trust bank will give you and them the benefit of the doubt when sh*t hits the fan.”

Kelly Watkins suggests 1-on-1 meetings ahead of your quarterly board meetings,

“Have 1:1 meetings before the quarterly meeting so that you have a sense of what matters to each board member and you feel prepared to engage with their questions and feedback.”

This advice from Kelly is something I witnessed first hand at Patreon. Jack regularly spent one on one time with board members, but he was very focused on this ahead of every board meeting. He’d go through the agenda with each member individually and collect feedback and questions from them. He would then relay that information to the rest of the executive team so that we knew what specific areas were important to each board member and could better prepare for discussion. 

As a result the leadership team who attended the board meetings showed up incredibly prepared, the meetings stayed on track, and the discussions were rich and productive.

Main takeaway: just as you’d do with your own teams internally it’s important to build trust with your board. This is best done in one-on-one conversations and through the seven other themes shared above.

#9 - Bonus Advice!

There were two additional pieces of advice I received that didn’t fit neatly into the themes above.

The first is how to manage your time as a leader through re-using board communications.

Sara Mauskopf,

“If I'm preparing something for my board deck, I try to leverage it for other purposes (or vice versa - if I'm preparing something for another purpose, it might also be useful to share with my board). For example, sometimes I will share upcoming product stuff we're working on with the board and then I can reuse the same mocks/slides to show to a customer or for a sales pitch. Sometimes some slight alterations are needed or I will get feedback in between, but I've tried to look at the board slides as an opportunity to prepare materials that I might not otherwise take the time to work on and therefore should use for other purposes when I can.”

The second is what to do if you have a finicky or difficult board member. Despite all of the efforts above, it can still happen. Kelly Watkins shares her advice on how to manage this situation:

“This one is tough. Having a direct conversation 1:1 is the best first course of action. Give specific examples of behavior that isn't helpful. Ask what the person needs to feel successful in their board role. Work to turn them into an ally and partner. This doesn't always work though, so if not, it's okay to solicit the help of other board members in speaking with the person.”

Closing Thoughts

Board communication is hard – no one gives you an instruction manual for this stuff and most founders (and executives) learn by getting it wrong. A lot.

When I first joined Patreon there was a board meeting on my second day on the job. Jack, our co-founder and CEO, hadn’t developed the top-notch board communication and management skills that he would go on to develop over the course of the next few years. This board meeting was the turning point.

In that meeting he was being peppered with ideas and feedback from the board in real-time and frantically taking notes. He hadn’t followed many of the themes above. 

After that meeting one of our board members pulled him aside and said, “What the hell were you doing in that meeting?” He said, “I was taking notes so I captured all your feedback.” The board member said to him, “Jack, that’s the problem… you need to tell us what to do, not the other way around. Don’t take orders from us; you know your business and your customers best.”

Everyone in leadership at Patreon learned a valuable lesson that day: proactive, clear, and consistent communication with your board saves you a lot of pain and wasted time.