Why Your Board Members are Your Best Sparring Partners: An Interview with Dan Rossignol

  • By: Adam Wire
  • June 7, 2022
Dan Rossignol
Reading Time: 9 minutes
Dan Rossignol

Don't be surprised by aggressive behavior in board meetings. Instead, prepare for it. Accomplished investor Dan Rossignol shows the way.

Your board members may not be your friends—and that’s OK.

You just have to be prepared for it. 

Maybe preparing for your board meeting makes you lose sleep and break into a cold sweat. But those meetings can also prove to be a critical sparring ground where you identify where and how to push your business forward.

Dan Rossignol, co-founder of JKURV, can speak with authority when it comes to board meetings. The accomplished investor started in venture capital before transitioning to the role of startup operator, a space he occupied for the last 15 years. 

Today, Dan is tackling the KaaS space (Knowledge-as-a-Service), sitting on university and nonprofit boards, and simultaneously working as an Investor Scout for Bonfire Ventures. (Where, not incidentally, he has sat in as a board observer for plenty of startups.) 

Dan has seen board meetings from all angles. Early in his career, he helped prepare for them. Later, he was the one delivering the presentations. Today, he often sits on the board himself.

Dan provided us with his unique insider take on how to think like a board member so you can walk into meetings feeling poised and prepared. 

Dan’s 4-Part Framework for Board Meeting Success

It took Dan a solid decade of board meeting trial-and-error before he landed on the 4 key tenets that he deploys at every board meeting.

“Board meetings go astray when the people presenting can’t stay inside of their swim lane,” Dan says. 

Breaking down the board meeting game plan into 4 buckets helped Dan focus on what matters and avoid meetings that devolve into an unhelpful blame game.

1. People

When you’re leading a board meeting, it might feel like all the pressure is on you. But don’t forget you have an entire company of talented employees behind you—and your board members will get a better picture of progress by hearing from their perspective. 

Board members are primarily interested in 2 things when it comes to your company:

  1. Is your company durable?
  2. Is your company growing? 

Great people are the asset that will ensure a company hits both points successfully. 

“I used to find it really landed well when I would hire people from my previous network, instead of going through the challenge of recruitment. I would use that as a major win” says Dan.

Bringing in people you already know assures your board members they will be effective and get up to speed quickly.

Dan also recommends calling out existing team members by name to support statements made in the meeting and build confidence.

“Board members want to see a mini OKR,” says Dan. “Key results are driven by different people on the team that have to execute on those key results in order to get closer to the bigger objective.” 

2. Process

Every company should work to develop processes that lead to smooth scaling.

People and processes go hand-in-hand. People need good processes in order to become successful.

For Dan, this meant building out clear playbooks for roles like sales and customer success. For example: At one company, he created a handbook for sales development representatives (SDRs). When a new SDR joined the business, they could quickly scale because it was crystal-clear what they would be doing on Day One when they arrived, and the days that followed.

At another company, Dan created productivity metrics so it was transparent how account executives (AEs) were spending their time. 

The key is to share how these processes are impacting the growth of the company. 

“Are you building a playbook or a framework to have people wake up every morning and say, ‘I know what my role is’?” Dan asks. 

When board members know you have clear processes, it enhances their confidence that the business is durable and ready to grow.

3. Technology 

The short version: Spend your technology budget wisely.

The longer version: Today’s board members know there are a plethora of tech options to choose, and they may invest in or have contacts at those tech companies.

Dan likes to take a conservative approach when it comes to spending early-stage money on tech. It’s a simple philosophy: Your tech spend should depend on how much revenue you’re making.

“If we’re doing under $1 million in ARR, you will not see me spend money on a fancy CRM system. I just won’t buy it. I will use Microsoft or Google Sheets to build a CRM. I communicate that to the investors and the board,” Dan says. “I want to be very upfront with them that this is the technology stack, given our stage and age, that we’re utilizing to be productive.”  

Board members are eager to see top-of-funnel movement. But it’s important to hold the line and invest in the right tech at the right time—because the board will also like smart investments. 

4. Accountability 

Yes, founders and CEOs are accountable to their board members. But don’t forget that your board members are also held accountable to their limited partners. (Where all that VC money came from in the first place.) 

“Founders don’t understand we have to do the same dog-and-pony show they have to do,” Dan says. “We’re not trying to be jerks. We’re just going to have to go take that into our potential quarterly meetings with our limited partners.” 

The solution is to provide a constant stream of clear, updated metrics so your board members can see how they transform over time. 

Do you find board members are always asking about the same information? Take note and be sure to wrap those details into subsequent board meetings to save time. 

If your board members walk away from a meeting with subjective updates instead of the concrete numbers they need, they will inevitably circle back with you 1-on-1 after the meeting. To avoid a slough of individual phone calls and follow ups, your best approach is to address everything in the board meeting itself. 

How to Prepare for Board Meetings

We’ve established that board members can be unrelenting in the pursuit of the information they need. This means you shouldn’t be surprised by aggressive behavior in board meetings. Instead, prepare for it. 

“I have yet to be in a venture-backed board meeting that hasn’t felt hostile. And hostile doesn’t necessarily mean it’s wrong. It means that people have a fiduciary responsibility to provide a return for the capital,” Dan says.

That level of responsibility is sure to keep people on their toes. Here are Dan’s top tips for keeping board meetings as smooth as possible. 

Turn One Board Member into a Sounding Board

While it’s true you can’t please everyone, Dan suggests finding one person on your board who is engaged and approachable, and treating them as your proxy. He puts it a bit more bluntly: 

“Try to find a board member that actually likes you and run your playbook or framework or whatever you’re going to do through them first,” Dan says.

If you notice a board member who nods their head during your meetings, don’t take them for granted. Those are the board members who you can likely build rapport with and use as a sounding board when preparing for future meetings. 

If you’re curious about how to recruit board members in the first place, read Recruiting Board Members: 5 Steps to Find the Right People.

Rehearse With Your Team 

Dress rehearsal isn’t just for drama class. It’s critical that you do dry runs to prepare for each board meeting presentation.

Dan’s biggest recommendation? Enlist other employees to help you prepare the board deck, even if they won’t attend the meeting itself.

It’s easy to think of board meetings as a top-down activity, when in reality they are a bottom-up endeavor.

“It shouldn’t be just the C-level or the VP-level building these things. It should be a bottoms-up pursuit. We’re the mouthpiece for the rest of the company, so they should have a reason to participate during that process,” Dan says.

The silver lining of involving others is that you can then call them out by name during the board meeting, feeding into the “People” tenet of Dan’s 4-part framework. When you can say your Head of X is seeing Y, it carries more weight than your word alone. 

Keep Slides Simple and Direct 

The same advice that holds true everywhere from the classroom to SXSW applies here: When preparing your deck, don’t overfill the slides. 

Venture-backed board meetings aren’t the place for excessive fluff, distraction, and BS. Your board members are there to get the current lay of the land in a direct and efficient manner—so keep slides brief and to the point. 

The place for extra information is on your pre-reads, not on the board deck slides.  

Saying less can also help everyone get more value from the board meeting. Why? Because it encourages board members to ask questions.

“I’ve always found some of my best presentations have been one-line slides. They look at it, ask a question, and extract more value in the meeting,” Dan says. 

OnBoard’s 2022 Board Effectiveness Survey showed just how important engagement can be: 49% of participants said a more engaged board is a primary driver of overall effectiveness. 

5 Things You Shouldn't Do

Looking for a quick cheat sheet of what not to do? Now that you’ve heard what Dan does recommend, let’s explore the things he says you should avoid at all costs. 

1. Don’t Reschedule Meetings

Once you set a board meeting date, it’s sacred. Don’t reschedule it.

Your board members can and will ask you to change meeting dates, but you should never be the one to initiate a change.

The most common reason that founders reschedule? They feel unprepared. 

Dan’s response: “If you have a board meeting, don’t reschedule … be f*cking prepared.”

To ensure you pick times that work well for your board members, reach out to executive assistants. This will help ensure you choose the best dates and times to avoid things like Zoom meeting fatigue where a board member is jumping from back-to-back meetings. The rest of the meeting prep is up to you.   

As remote board meetings continue to gain traction, tools like board management software become increasingly valuable. 

2. Don’t Share Details that Aren’t Set in Stone

It’s tempting to tease exciting tidbits on your pre-reads, such as a new deal that’s on the cusp of signing.

Dan’s opinion is that you should only mention things that are 100% final on pre-reads and deck, because board members will assume anything they read is a done deal.

You don’t want to be asked about the items in the board meeting, have to tell the board it’s not done yet, and give the sense that you are behind schedule.

The “opportunistic” items you should avoid oversharing include things like:

  • New deals
  • New hires
  • Product delivery
  • Product releases

Instead of sharing those items on pre-reads, share them during the board meeting itself to build exciting momentum. 

3. Don’t Lie 

This one is obvious in theory, but can be challenging in practice: Don’t lie.

Leading a board meeting requires total honesty. Board members will appreciate having an accurate picture of company performance, not a sugar-coated one. 

“If you have a story that sucks, tell the sh*tty story,” Dan says. “One classic mistake that founders make is to treat board meetings the same as VC meetings as they raise capital. They want to come in with the progressive, ‘We’re up here! We’re going! We’re moving!’” 

But once you have capital from your board members and investors, that’s not the type of rhetoric you need. You need to be honest and straightforward. 

4. Don’t Ask for Help You Don’t Want

Many founders believe if they’re not asking board members for favors, they’re doing something wrong. 

Dan is of the opinion that you should definitely ask your board members for help, but only if you actually need it and plan to follow through on their tips, introductions, and advice. 

“You don’t have to have asks at all in the meetings,” Dan says. “If you are very, very, very early—think seed and pre-seed—I can understand why you would take this as an opportunity to want to learn from your board members.”

Just keep in mind that it’s a slippery slope, as your board members will expect you to act on the advice they give; be sure you really need it. 

5. Don’t Forget About Diversity 

Whether it’s race, gender, religion, professional experience, or simply diversity of thought, diversity is an often overlooked asset in board meetings.

“If everybody is the same, then you’ll go in the same wrong direction time and time again,” Dan says. 

He speaks from experience. One company he worked with had an all-male board for a product that had a female end-buyer. It didn’t end well.

Having a diverse board sometimes isn’t enough. The CEO or founder will also want to find ways to ensure that all valuable voices are heard. 

Since a board meeting isn’t a classroom where you can call on attendees, you’ll want to ask board members individually beforehand. The request can be as simple as sending out the pre-reads and letting a particular board member know: “This would probably be most interesting for you, please feel free to come with your thoughts on this particular slide.” 

Looking for more communication tips? Read 6 Tips for Effective Board Communication.

What Changed for Boards in 2022?

Everything. See the trends that shaped boards and their meetings in 2022.

Go Forth and Conquer Board Work Collaboratively

While your investors may not be your friends, they are a valuable resource, sounding board, and forcing function to help you grow. Board members serve as a valuable reminder to CEOs that they need to remain responsible to their investors and true to their mission. 

Learning the right sparring techniques can help you walk into every board meeting with your ego at the door, and the facts at the ready. 

Ready to level up your board meeting game? Check out OnBoard’s board management software. Featuring an unlimited cloud-based resource center, your board members can access meeting minutes, agendas, and up-to-date information all in one place. 

Want to fuel your startup for success? Get started with a free trial of OnBoard

About The Author

Adam Wire
Adam Wire
Adam Wire is a Content Marketing Manager at OnBoard who joined the company in 2021. A Ball State University graduate, Adam worked in various content marketing roles at Angi, USA Football, and Adult & Child Health following a 12-year career in newspapers. His favorite part of the job is problem-solving and helping teammates achieve their goals. He lives in Indianapolis with his wife and two dogs. He’s an avid sports fan and foodie who also enjoys lawn and yard work and running.