Build A Budget Based In Reality

What I Learned From the Worst Year of Budget Meetings

Jess Skylar with Amy Omand


Long Story Short

Most budget processes start with a spreadsheet. The good ones start with a conversation. Specifically, getting everyone to agree on your financial “season” before anyone touches a number. We built you a Budgeting Toolkit with conversation scripts, a step by step work plan, and a sample memo you can share with your board.

Jump to How!


The year I learned budgeting the hard way

Jess here!  

Early in my career, I built what I thought was a great budget. It was technically accurate. The math made sense. The board and senior leadership approved it (after a LOT of vetting). 

And then I spent the next twelve months sitting in meeting after meeting, reporting how we had — yet again — failed to meet our projections.

Here’s what happened: I worked in school food and, at the start of the school year, schools always ordered extra meals. It took a few weeks to figure out how much kids were going to eat and our schools did NOT want to run out of food at lunch.  

Every week, after my schools placed their orders, I would look at the actual orders and compare them to my initial projections. Things were looking really GOOD for the first month of school — we were beating our projections and I felt like a hero! While my markets were hitting their goals, others were not. I knew our company needed these dollars and I was the one bringing in the revenue!!!!

The start of the school year happened to line up with budget-building season. While building my draft budget, I kept the schools we had worked with for years at their historical averages, but made a big mistake with the new schools: I took the “actuals” from the start of the current school year and put those right on in our draft budget. I did give them a small haircut to be conservative, but I wasn’t conservative enough. I was so excited about our success early in the school year that I made myself believe that these numbers could be true all year long, even though I knew better….  Sometimes you just wish things will be true?!?!?

Everyone signed off on these numbers — in part because they trusted me, in part because our company really needed and wanted the numbers to be true. AND, nothing changes the fact that I was the one who put them there. I was the one that stood behind the numbers.  

The budget was approved in September and by early October we were starting to fall behind.  By mid-November, it was clear that we were never going to catch up.  

From that point on I went to our monthly budget meetings with my shoulders sagging and ready to accept full responsibility for getting it wrong. And, every month, I felt the weight of how my revenue projections hurt EVERYONE involved. People in our corporate office and other regions had been hired based on the numbers I’d put in the budget. My attempt to play the hero and will my numbers to be true didn’t just hurt my team, it hurt every department that was counting on that revenue. It was, for lack of any other better way to describe it, terrible.

I felt like I was slowly drowning —  in public —  and the worst part was that if I had budgeted realistically from the beginning, our region would have been the highest performing in the company. Instead of drowning, I would have been soaring.

That experience changed how I think about budgeting forever. Not the mechanics — I already knew how to build a spreadsheet. What I learned was this: The spreadsheet is almost never the hard part. It’s the context and the rationale and the relationships and the reasoning behind it that you have to get right.

Budgeting is really about getting humans on the same page. It’s about consistent grounding and understanding and context to make sure everyone understands where we are, what we’re trying to accomplish, and what is most important.

Are we cutting back?  Are we growing + investing? Are we steady state?  How does that vary department to department?

What are our highest priorities?  Why are those our priorities?  

How do revenue projections and headcount in one department impact another?  Directly and indirectly?  

I didn’t know any of this because I didn’t ask. Without the full picture — with just me sitting alone with my spreadsheet — I was planning and reporting for something separate from our company’s reality.  I was part of a much bigger picture that I didn’t understand, and not understanding it meant that I provided something unreliable that became a foundation for decisions well beyond what I was looking at every day. 

I messed up.  Big. It was painful AND I learned something I’ll never forget: ALWAYS base your budget in reality. 

Are we cutting back?  Are we growing? Are we steady state?  How does that vary department to department?


A person who has designed a better way

I worked briefly with Amy Omand at Revolution Foods. She reached out when we started Helia with the goal of sharing her wisdom about how to run a thoughtful and comprehensive budget process. One that brings the context and the nuance and the full team along. 

Her process is grounded in a “bottoms-up” process and shows the step by step needed — as well as the framing she’s used — to create a solid budget process that helps avoid the debacle I created all those years ago. Amy’s process gets you a budget that’s not just solid but is grounded in reality. It’s a budget that provides clarity, builds ownership, and is usable all year long.

Woman hiking on a coastal trail with two dogs, overlooking rugged cliffs and the ocean.
Amy and her dogs!

The Key Takeaway


Most budget processes start with the spreadsheet. The good ones start with the conversation. Before anyone touches a number, everyone needs to understand:

  • What’s our actual financial reality? (Are we expanding, holding steady, or contracting?)
  • What are our real priorities? (Not the strategic plan we wrote two years ago — what actually matters NOW?)
  • What does success look like this year?

The reason my optimistic budget failed wasn’t that the math was wrong. It’s that I’d never had the honest conversation about where we actually stood. I built a budget that would have been fine if we were operating as just our market — I could have adjusted expenses and balanced it all out.  But we were part of a bigger company and all the math needed to add up together. As hard as it is to admit, it wasn’t all about me!!!


Amy’s 4-Step Budget Process

If you’re a “I want to see the template, I’m ready to get started” kind of person (aka Helia’s COO Libby), check out Amy’s 3-Month Budget Workplan in our Budget Toolkit — it walks you through the whole approach step by step, including exactly who does what and when.

If you’re a “tell me why this works” kind of person (aka our Founder Jess), read on. Here’s what we’re going to cover:

  • Step 1 — Name your season (abundance, steady state, or contraction)
  • Step 2 — Plan for three months and get the right people involved
  • Step 3 — Use bottom-up budgeting with clear guardrails
  • Step 4 — Create feedback loops throughout the year

The Magic That Makes This Process Work


Step 1: Name your season — and say it out loud

When Amy launches a budget process, the first thing she does is name the financial reality. She calls these “seasons” — and identifying which one you’re in changes everything about how you budget. The three seasons:

  • Abundance season: You’re confident in your reserves. You have committed funding or strong revenue streams. Your approach with budget managers can genuinely be: “Tell me your biggest dreams and plans.” This is the season for investment, for trying new things, for saying yes more than no.
  • Steady-state season: You’re not in danger, but you’re not growing either. The goal is to maintain what’s working and be judicious about spending. You’re budgeting at a continued run rate — keeping up the work, but not adding anything incremental.
  • Contraction season: Revenue is down or uncertain. You need to spend less than last year. Amy puts it this way: “Contraction mode is tough but it’s a reality that needs to be tackled head on.”

Why this matters: The mistake we see over and over is leaders who don’t name the season. They say “give me your budget” without context, and then are shocked when people ask for the moon or when they feel confused that the CEO comes back investing in one department and cutting three others by 30%.

Here’s an example of language you can use for talking about contraction that doesn’t destroy morale:

“I want to be direct: we need to make strategic reductions this year to protect our financial health. Rather than across-the-board cuts, we’re working together to identify where we can thoughtfully reduce while protecting our work and our team. This is hard, and we’re going to get through it by being honest about constraints and strategic about choices.”

People won’t engage honestly with a change if they aren’t sure what that honesty will mean for them. You have to give them safety and clarity before you can get their real buy-in.


Step 2: Plan for three months and get the right people involved.


Amy’s rule: for a December 31 year-end, start in September. Three months out might feel early, but you need time to do this right — especially if you’re involving budget managers (which you should).

Amy’s actual timeline:

  • Month 1: Draft timeline, identify who needs to be involved, determine your budget season, provide clear context to your team about the parameters you’re operating under.
  • Month 2: Budget managers build first drafts based on templates and guidance you provide; the first round of reviews begins.
  • Month 3: Strategic decisions, continuing rounds and final revisions as needed, board presentation.

Why three months? Because good budgeting isn’t just filling out a spreadsheet. It’s having conversations. It’s an iteration. It’s making sure everyone understands the context before they touch a number.

Amy is emphatic about this: “Put it on the calendar. A budget is a must-have, not a nice-to-have. Treating it as a critical priority signals to everyone that this matters.”


Step 3: Use bottom-up budgeting — with guardrails

This is where most budget processes go sideways. You either:

  1. Do it top-down (CEO and finance person build everything) and no one has ownership, or
  2. Do it bottom-up (everyone submits their wish list) and you get chaos

Amy’s approach threads the needle: Involve budget managers in building their budgets, but with clear context and parameters.

  • Give them context: Tell them the season. Tell them the constraints. “We need to stay flat to last year” is very different from “tell me your wildest dreams.”
  • Give them data: Bring last year’s actuals into the conversation. People can’t budget well if they don’t know what they actually spent.
  • Know your people: Here’s a story from Amy that I love. During the pandemic when everyone suddenly went remote, she had one employee requesting an $800 standing desk and another using a cardboard box to prop up their computer. Neither was wrong in their approach, but if you’re managing these folks, you need to know who needs permission to ask for what they need and who needs boundaries on what’s realistic. Some people ask for the sun, moon, and stars. Others won’t ask for anything. Know your people well enough to give the right guidance.
  • Build in flexibility: Include space for “if I did have 10% more, this is what I would do” and prioritization levels (must-have vs. nice-to-have). This way, when the CEO needs to make trade-offs, they have the information to do it well.

Amy makes one more critical point: Ask budget managers to actually add in the story — ‘this is under budget because of X, we are increasing this because of Y.’ This context ensures they are thinking things through gives everyone else in the process enough context to make informed decisions. This might look like:

  • “We’re running about 20% over on travel this year — this is because we won 3 new accounts unexpectedly and are sending the team on-site to support the launch. While we’re over budget, it’s directly covered by the new revenue and we don’t expect this to repeat next year.”
  • “We are reducing our revenue to be 10% lower than this year given uncertainty in the funding environment. While we’re still working to identify ways to navigate this, we’ve also proactively reduced revenue AND expenses.”

Good budgeting isn’t just filling out a spreadsheet. It’s having conversations.



Step 4: Create feedback loops — not surprises

Amy builds in multiple rounds of review with clear expectations. She tells everyone upfront: “This is not the final budget. It needs to go through several rounds of review.”

  • First review: CEO and finance person review together. This is where you see the full picture and identify questions.
  • Back to managers (as needed): Sometimes the first pass is great. Sometimes you need more information or need to push back on specific areas. The key is that these conversations happen weeks BEFORE the board meeting. You want all the time you need to be able to sit side by side and make thoughtful iterations.
  • CEO follow-up review: Every time the managers make adjustments, the CEO and the finance person do a full review. If critical questions come up, the budget goes back to the managers until all questions are answered. If it’s good to go, the budget goes onto the board.
  • Board presentation: Amy says she’s never been in a board meeting where the budget actually changed. “Often the board has lots of great strategic questions, but generally they are inclined to approve the budget as it’s presented IF they’re kept up to date on the process and detailed work that’s gone into it.”

Why this works: Action builds trust. If you’re going to act on what you learn quickly, people will keep telling you what’s really happening. If feedback disappears into a black hole, people stop giving it.

But the process doesn’t end when the board approves. Amy recommends budget reviews with budget owners monthly or quarterly, depending on complexity. “If you approve a budget in January and never look at it again, you’ve wasted all that work.”

**View from a paddleboard on calm water at sunset, with distant islands and sunlight reflecting across the surface.**

Amy enjoying a day on the lake.


When to do this Yourself vs Bring Someone in


Everything I’ve shared above? You can do it. Seriously. If you have a decent handle on your finances and a team that trusts each other, this process will work.

AND, if you’re overwhelmed or it feels daunting or there are lots of things happening, you might want outside help.  Here are a few moments I’d think about bringing someone in:

  • You’re too close to the politics. You know the cuts need to happen in a specific department, but you also know that conversation is going to be brutal — and you’re not sure you can facilitate it without it getting personal.
  • You’re the bottleneck. You’re the only one who really understands the finances, and you don’t have time to bring everyone else up to speed AND build the budget AND run your actual programs.
  • You’re avoiding something. There’s a conversation you know you need to have — with your board, with a budget manager, with yourself — and you keep putting it off. Sometimes you need someone from the outside to help you say the hard thing.
  • Your board is asking questions you can’t answer. Not because you don’t know your stuff, but because you don’t have the benchmarks, the comparisons, the “here’s what other orgs your size are doing” context.
  • You’ve never done this before and the stakes feel high. First budget? New ED role? Suddenly in contraction mode after years of growth? There’s no shame in wanting a thought partner who’s seen this movie before.
  • Prioritization feels impossible. Everyone’s used to getting everything, and you need someone from outside the politics to facilitate the tradeoff conversation.

Here’s the thing: I’ve watched smart, capable leaders get stuck — not because they don’t understand budgeting, but because they’re trying to be the expert AND the facilitator AND the decision-maker all at once. Sometimes having an outside perspective — even just for a few hours — changes everything.


If you want a thought partner to help get you through this budget season

Amy Omand is a fractional CFO who works with social sector organizations — nonprofits, foundations, and social enterprises — to build financial systems that actually work.

She’s a good fit if:

  • You’re a $2M-$30M organization without a full-time finance leader (or your finance person is more bookkeeper than strategist)
  • You’re in a transition moment: new ED, first real budget, shifting from growth to sustainability, preparing for a board that’s asking harder questions

What working with her can look like:

  • Fractional engagement: Amy works with a handful of clients at a time as their ongoing finance partner — think of it like having a CFO on retainer without the full-time cost
  • Single session: Not sure what you need? Start with a free 30-minute call to talk through where you’re stuck

What people say: “Amy helped us see our finances as a strategic tool instead of just a compliance exercise. For the first time, our budget actually reflects our priorities — and our board meetings are completely different.” — ED, education nonprofit

Connect with Amy!

Book a chat Email

Try It Yourself

Amy’s Budget Reality Toolkit

  • Amy’s 3-Month Budget Workplan — The actual timeline Amy just used with a client. Not a template; a real example of who does what and when.  (It’s actually pretty simple, no Gaant charts required!)
  • Budget Conversation Scripts — Six scripts for the hardest budget conversations: explaining contraction mode to your team, pushing back on unrealistic asks, presenting to your board, and creating safety around variance reporting.
  • Amy’s Sample Budget Memo — What “telling the story” looks like in practice. See how to present numbers with context – with an actual Board Budget memo Amy used.

If you need the basics:

Questions to Sit With

Before you dive into the your budget season, ask yourself:

What season are we actually in — and does everyone know it?

  • If I asked five people on my team what our top priorities are for this budget, would they give the same answer?
  • Are budget managers set up to see their spending throughout the year, or are we asking them to budget blind?
  • Is our chart of accounts helping our decision-making or just creating complexity?
  • What’s the conversation I’ve been avoiding?
  • If we lost 20% of our funding tomorrow, do we know what we’d cut? Have we talked about it out loud?

Not sure Amy‘s the right fit? Talk to Helia directly!

Book a chat

This article coThis article comes from a conversation with Amy in September 2025 — and from my own painful experience learning what happens when you skip the human part of budgeting.
We share these stories in the Helia Library because we want everyone to remember we get to do this together. Take what’s helpful, leave what’s not, and make it your own.
mes from a coffee chat with Laila in October 2025 — and from my own years of being “pretty good” at delegation while never quite getting it right.


Woman hiking on a coastal trail with two dogs, ocean cliffs visible in the background.

About Amy

After getting her CPA right out of college, Amy discovered her superpower: making numbers tell stories that help organizations make better decisions. She spent years working everywhere from Dreyer’s Ice Cream (which she describes as “very yummy”) to social impact organizations before starting her own fractional CFO practice. Her secret is understanding that behind every budget line item is a human who needs context, ownership, and clear expectations to do their best work.

Work with Amy
Take what’s helpful, leave what’s not, and make it your own.
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