Making annual planning more approachable: a conversation with Rillet’s Head of Finance

I’ll never forget the first time I had a full blown misunderstanding at a budgeting meeting. It was your standard hour-long meeting—each department wanted more money than we could realistically provide. Our forecasts made it clear we wouldn’t have enough cash to meet all demands, so I had to cut budgets across the org.

I was meeting with department heads one at a time to negotiate. Twenty-five minutes into a conversation with the Ops Lead, he suddenly asked me: “Why am I the only one who has to cut spending?” 

I couldn’t believe it.

I wanted to throw him across the room. But I immediately realized it wasn’t his fault. It was mine. He didn’t know this was happening to everyone.

I think about this a lot during annual planning. It’s the worst time of year to be in finance. You have to push the sales team for more revenue while simultaneously cutting marketing spend. You have to revise your plan over and over and over again, wondering how many more revisions you’ll go through before the board finally approves it. And you have to do all of that while juggling your regular workload.

Each year is different, and every company is different too. But I’ve realized that getting planning right isn’t just about the numbers; it’s also about the humans on the other side of the table. Here’s what I’ve learned that the hard way:

Give people the full context

The misunderstanding with the Ops Lead was on me. He wasn’t upset about the budget cut itself—he was upset because he felt singled out. He didn’t know that cash was extra tight that year, or that every department had asked for more than we could support (even in our most optimistic plan). I’d made the mistake of not providing spending targets upfront, so I had to meet with every team to cut their requests.

I’d even spent the whole morning cutting my own budget in half, but he didn’t know that. He just saw that I was asking him to cut a quarter of his, and felt frustrated. That’s on me.

As finance leaders, it's our job to provide clarity on the total budget and how each department fits within it. When I was at Walmart, they did this really well. They were obsessed with profitability. They’d tell everyone that increasing spend by X would reduce earnings per share by a penny. Similarly, at startups, department heads should know how much runway is lost for each $100K or $1M increase in spend. Because when people understand how their budgets impact the business as a whole, they make decisions that align with the company's goals.

Use plain English with non-finance folks

Early in my career, my CFO asked me to create a budget template for department heads. Seemed simple enough, so I made a template and sent it to him. He immediately sent it back, and said: “No one outside our team will understand this. Make it simpler.”

He was right. My template was full of jargon—GM%, COGS, CAC—that only made sense to our team. So I went back and spelled out the acronyms, used plain language, and defined exactly how I was calculating ARR (instead of obscuring it behind an unreadable formula). I even changed "gross margin" to "gross profit" because it's more widely understood.

What I learned is obvious, but also very easy to forget: regardless of which tool you're using for budget submissions—Excel or specialized software—it needs to be accessible to non-finance folks. Otherwise, you'll spend more time explaining how to fill out forms than discussing how the numbers impact the business.

Share your model (within reason)

In the past, I often told department heads I couldn't share our financial model because it contained sensitive information—like salaries. While that was true, it wasn't the full story. I was also worried opening up the model would raise more questions than it answered and, honestly, that someone would end up breaking something. 

As the company scaled—and we entered new markets or added new channel partners—our model became more complex. Sometimes, in a hurry, I’d add hardcoded values or temporary hacks just to make it work—things only my team knew about. It didn’t take too long for the model to turn into Frankenstein. And when that happened, only the finance and accounting team could actually make sense of it. 

This caused a lot of issues, especially with the growth team. They had their own forecasting templates, and I'd spend hours each month converting their numbers into our model. Eventually, I built a simplified version of our model that only included what they needed—things like revenue forecast and marketing spend. Sharing this simplified model reduced both time and tension, but it wasn’t perfect. I still had to manually consolidate forecasts. And I still had to keep track of different versions because there was limited version control.

Today, there are tools that make this much easier. You can share parts of the financial model without exposing sensitive data. You can actually lock away salary data securely, instead of just hiding a column in a spreadsheet that anyone can easily unhide. Department heads can play with drivers and see how changes in ARR or gross margin impact the bottom line. Your model doesn’t have to be a black box anymore—even if you only share it in pieces.

Collaborate, don’t just calculate

Planning is tough and inevitable, but it doesn’t have to be painful. When we focus on the people involved, provide them context, use plain language, and keep things transparent, it gets way smoother.

I think it’s important to never forget the human side of it. And start earlier than you think. Always.

That’s all. Good luck this planning season. If I can help you in any way at all, feel free to reach out!

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