Investor updates: How to make the most of your board meetings

There’s one song in my Spotify shuffle that always reminds me of prepping for board meetings. The lyrics don’t have anything to do with financial statements or ARR; that would be odd after all. It just happened to be a song I discovered the same weekend I spent preparing for my first startup board meeting. The CEO, CFO, and I were in the office the whole weekend, tweaking the model, cleaning up the slides, and thoughtfully adjusting the story. Every time that song comes on, I go back to that standing desk in the corner of our San Francisco office, bobbing my head as I adjust the variables for just one more scenario.

Board reporting is hard. There are too many stakeholders and too many opinions. But there are intentional steps we as finance leaders can take to run a smooth process, both for us and our stakeholders.

Here are four key strategies I’ve used to improve my board reporting since that fateful day in San Francisco.

1. Align with department heads beforehand

One of the biggest challenges in board reporting is ensuring all key players within the organisation are aligned on the same numbers, goals, and narrative. When reporting to the board, inconsistencies in data or diverging views between departments can create confusion and undermine credibility. It didn’t matter what company I was at or how many quarters I had worked with the growth leader; our first drafts always had different performance numbers. Aligning this is rarely straightforward. At a hardware company, the growth team wants to count anything sold while finance only considers what has actually left the warehouse. For software, growth justifiably wants to count net new ARR while finance may only report contracts started in the period.

The resolution must be crystal clear prior to both the meeting and shipping the board deck (always done at least 3 days in advance). My recommendation: different terminology. Growth should use Committed ARR (CARR) for topline reporting. This gives the team credit for pulling deals across the finish line at the end of the quarter. Finance should use ARR to consistently report year-over-year growth and downstream metrics such as ARR per customer and NRR. Alternatively, you could decide to go with growth’s number or finance’s number. I find more often than not that this leaves both parties frustrated. Over the long term, it misaligns incentives and fractures the relationship.

Aligning on the forecast is just as important. Take a specific example: your product roadmap indicates aggressive growth over the next two quarters, but the financial model shows conservative revenue estimates. This must be reconciled before it reaches the board.

A consistent collaboration process not only smooths over potential contradictions but also strengthens your narrative in front of the board, giving directors confidence that the entire leadership team is in sync.

2. “Disagree and commit”

The core objective for every finance leader is simple: never run out of money. Naturally, this results in a conservative approach to just about everything, particularly the forecast. The CEO has a different objective: conquer the world. This can put the CFO and CEO at odds. The differences are good, and in an ideal world, you meet in the middle. We rarely live in an ideal world.

As finance leaders, we tend to resolve forecast differences with scenarios. I think that’s generally the right approach. You present your base case, complemented with upside and downside scenarios. If you miss your base case, at least you’ve messaged ahead of time and can clearly explain the gaps.

But what about the more complicated decisions? I worked with a CEO who wanted to include an international launch in next year’s forecast. I thought there was no way we would be ready and told him so directly. We spent weeks going back and forth. Ultimately, I convinced him to reduce the forecasted revenue, but the launch stayed in place despite my protest. At the board meeting, I disagreed but I committed. I was fully behind the plan.

I won’t mention here which one of us ended up being right.

3. Delivering bad news: just do it

Surprises in a board meeting aren’t just bad. They’re a disaster. They’re also entirely avoidable.

Almost everyone knows you shouldn’t deliver bad news in a board meeting. But then when are you supposed to deliver it? I’ve found the best time is when you know you are going to miss something you told the board you would do.

If by the second month, you already know you will miss the quarter, don’t wait until the third month. Be upfront with it. You can still be clear on how you are planning to make it up in month three, but the worst-case scenario is the board asking, “Why didn’t you tell us sooner?”

Surprises can work both ways. We always do a short call with the key members of the board beforehand to ensure they are aligned with the agenda and key topics. For example, you should always know if the board will approve the annual plan before you go into the board meeting.

4. Build a pre-board meeting ritual

I’ve gotten some of the best advice from experienced finance leaders by simply asking, “How do you prepare for board meetings?” Everyone has their own process. I’ve stolen pieces from leaders I respect over time to develop my own. You should be thoughtful about how you design yours.

One of my first CFOs would spend the weekend before a board meeting writing a long-form narrative on the current state of the company. This narrative would rarely, if ever, see the light of day. That didn’t matter. The point was for him to know the numbers and the story from the inside out.

Another finance leader I spoke with recently said she’ll ask her husband for feedback on the narrative. It’s particularly helpful because her partner doesn’t work in finance and is able to bring a fresh perspective to the material.

I keep a printer at home for basically one thing: printing out the board deck. It is the best way I have found to catch errors and ensure I am familiar with every detail on every slide. (We all know... if it’s on a slide, someone is going to ask about it). If I just view the slides on my laptop, I might miss that the Q3 gross margin is different on slide 3 than slide 17. When I print it out, I can easily compare the slides to one another and ensure they are each in agreement.

On the day of the board meeting, I intentionally avoid reviewing the material. It just makes me think we should change everything. Instead, I review everything thoroughly the night before and let my mind slowly sift and organise the details as I sleep.

Whatever you decide to do, figure out a process that works for you. And ask your peers how they prepare for board meetings. I find it always leads to some good tips and a good story.

Conclusion: Board reporting as a strategic skill

As with any leadership skill, mastery of board reporting comes with experience, but these strategies provide a strong foundation. Improving board reporting isn’t just about presenting facts and figures—it’s about delivering a coherent, aligned narrative that builds trust and confidence (which also happens to help us keep our jobs).

Whether you’re preparing for your first board meeting or your 100th, good luck out there! I hope it goes better than you think. And if it doesn’t... well, there will always be another one in three months :).

About the Author 

Stephen Hedlund is the Head of Finance at Rillet. He has over a decade of professional experience in corporate FP&A and startup finance, with leadership roles at OpenSpace, Molekule and Walmart. He holds an MBA from the University of Chicago Booth School of Business. Outside of work, Stephen loves being a dad to his 2 kids and indulging in coffee.

About Rillet:

Rillet is an automation-focused ERP for mid-market SaaS and Usage companies with pains around revenue recognition and multi-entity consolidation. Rillet can automate 93% of all manual journal entries and invoicing workflows and provides key investor metrics instantly. See tech stack survey, case studies,G2, happy customers and happy partners. We are backed by leading investors such as First Round Capital and Creandum.