Your headcount requests keep getting rejected? Learn the four common mistakes leaders make when justifying new roles and how to win finance over next time.
Justifying new headcount can be one of the trickiest parts of leadership. Many leaders feel the pain of overextended teams and instinctively know more people are needed. But too often, headcount requests fall flat – not because the need isn’t real, but because the justification misses critical alignment points.
In our recent webinar on capacity planning, David Binnings, Sr. Director, GTM Services Strategy and Operations at DocuSign, shared some of the most common mistakes he’s seen leaders make when making the case for new roles – and how to avoid them.
One of the biggest pitfalls is treating headcount requests as an isolated operational issue rather than a financial one.
As David explained,
I’ve seen requests for headcount fall flat because they’re not integrated with the finance teams.
Finance often holds the purse strings and builds its own top-down capacity models, typically based on projected revenue and utilization assumptions.
“They may go look at it and say, ‘Okay, you’re going to make X millions of dollars – you should be able to do that with 100 people,’” David said. “But they’re missing out on that internal work bucket – the non-revenue work that still takes up capacity.”
From the finance perspective, the math checks out. But from the delivery side, things often look very different. Teams are stretched thin not only because of revenue-generating work, but also because of internal initiatives, operational tasks, and non-billable work that don’t appear in finance’s capacity models.
When those hidden demands aren’t factored in, finance may push back on headcount requests – believing the existing team should be enough. The result? Misalignment, frustration, and delayed growth.
Another common mistake is leading with the symptom (“we’re too busy”) rather than the underlying cause (“here’s what’s driving the workload”). Without data and context, it’s easy for finance to see busyness as a perception issue rather than a resourcing problem.
The key, David notes, is to clearly connect the dots between work demand and business value. Show how the extra capacity will directly support revenue, strategic projects, or risk reduction – and point out the internal work buckets that aren’t visible in finance’s models.
This shift turns the conversation from emotion (“we’re drowning”) to evidence (“we’re constrained by X, and here’s the impact if we don’t act”).
Headcount justification shouldn’t start when the annual budget is being finalized. By then, finance already has its numbers locked in.
David emphasizes the importance of ongoing collaboration:
Before annual planning starts – and even during the year – having regular cadences with the finance team to truly understand the real capacity picture is super important.
When finance understands the real-world dynamics affecting delivery — including the non-revenue work that consumes time and energy — they’re far more likely to advocate for additional resources when the moment comes.
At the end of the day, finance isn’t the enemy – they’re an essential partner in scaling sustainably. Building that relationship early pays off. As David puts it,
If you can bridge that gap with finance early on – to where they understand why you need that headcount, not just that you’re busy – it makes all the difference.
Successful headcount justification isn’t just about proving you need more people – it’s about showing that your need fits into the company’s financial logic. By integrating capacity planning with finance, articulating the full scope of demand, and maintaining open communication year-round, leaders can turn headcount requests from uphill battles into strategic conversations.
