Caterpillar Garden

Caterpillar Garden

Share this post

Caterpillar Garden
Caterpillar Garden
[RBM+E] "A" - The finance department is your best friend.

[RBM+E] "A" - The finance department is your best friend.

Caterpillar Garden's avatar
Caterpillar Garden
May 07, 2025
∙ Paid

Share this post

Caterpillar Garden
Caterpillar Garden
[RBM+E] "A" - The finance department is your best friend.
Share

In this post (partially free), I'll reveal how the finance department can become your strongest ally in driving modernization and digital transformation initiatives. After a couple of sales trainings and leading various projects, I've discovered that financial teams are uniquely positioned to support your proposals—when you speak their language.

black flat screen computer monitor
Photo by Nick Chong on Unsplash

Through this guide, I'll share a proven framework for engaging with finance professionals that transforms them from gatekeepers to advocates:

  • Understanding finance's core motivations

  • Creating compelling initial presentations

  • 🔐 Developing ROI calculations that get attention

  • 🔐 Building collaborative relationships instead of adversarial ones

  • 🔐 Leveraging finance's influence with decision-makers

The first chapters will give you the foundational approach to start building these critical relationships, while the premium part will deliver my detailed playbook for navigating the entire process from initial contact to final approval.

Let's begin with what makes finance different from other departments and why they're naturally inclined to support well-structured change initiatives.

Understanding finance's core motivations

Finance departments operate with three main goals: protecting company assets, ensuring regulatory compliance, and optimizing how resources get allocated. Here's the thing - they're not just "budget gatekeepers" like many people assume. They're actually strategic partners who care deeply about your organization's financial wellbeing.

difficult roads lead to beautiful destinations desk decor
Photo by Nik on Unsplash

When approaching modernization initiatives, understand that finance professionals prioritize risk management first - they need to understand what could go wrong before getting excited about what could go right. They speak in quantifiable terms and need metrics rather than promises. Their thinking also follows fiscal cycles - their planning horizons match up with budgeting periods. And predictability matters enormously to them because unexpected costs can seriously damage their credibility with leadership.

By recognizing these motivations, you can transform your relationship with finance teams. I remember working with one CFO on a cloud migration project. What I discovered wasn't resistance to innovation - she simply required different evidence than what my technical team was providing. Once I reframed our proposal, everything changed.

In my experience, finance becomes your strongest ally when you translate technical needs into financial outcomes. They actually understand technical debt deeply - just try showing them how your modernization reduces it! Have you considered involving them early in your planning? This helps structure initiatives to align with budget cycles. I've found that providing visibility into spending patterns builds tremendous trust through predictable cost models. And when you acknowledge their fiduciary responsibility, you're showing respect for their obligation to question investments.

Remember something I learned the hard way: finance departments aren't obstacles to your digital transformation. They're potentially your most powerful partners who can secure sustainable funding and executive buy-in - if you take the time to speak their language.

Creating compelling initial presentations

When I think about approaching finance teams, I've learned that you require more than just technical brilliance—you need a proposal that speaks their language. I always start with a document that frames the business problem in actual business terms (not tech jargon). Trust me, quantifying current pain points makes a world of difference here. With AI tools you can translate it easily, by the way!

I've found it's much more effective to outline multiple potential solutions rather than pushing a single option. In my experience, presenting two or three approaches with simple pros and cons gives finance professionals room to engage with your thinking. They appreciate seeing your reasoning process.

assorted spray bottles
Photo by Emiliano Vittoriosi on Unsplash

Don't worry about creating an exhaustive timeline upfront—I've seen too many good proposals get stuck in planning limbo this way. Instead, I sketch out major implementation phases to give them a sense of the journey. Similarly, with costs, I provide ballpark ranges based on clear assumptions rather than promising precise figures that might change. Have you noticed how much more receptive people are when you acknowledge uncertainty upfront?

To avoid the dreaded six-month proposal development cycle (we've all been there!), I've developed some practical engagement techniques. Start by requesting a quick 30-minute chat to understand their evaluation criteria—this simple step has saved me countless hours of rework. I always ask about budget cycles too because missing a funding window can delay your project by an entire year.

Something that's been game-changing in my projects is finding a finance "—sponsor"—someone from their team who can provide ongoing feedback. It's like having an insider guide! I also establish shared checkpoints where finance reviews incremental progress. And whenever possible, I ask if they have preferred proposal templates—why reinvent the wheel?

When I implemented this approach at a telco organization I worked with, we cut the approval process from seven months to just eight weeks. The difference? We brought finance in during week one rather than treating them as the final hurdle. It completely transformed the dynamic from adversarial to collaborative.

Keep reading with a 7-day free trial

Subscribe to Caterpillar Garden to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2025 Caterpillar Garden
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share