It's Monday morning. Your product manager, visibly excited, announces a "simple new feature", max 1 week of work. You open the codebase, stare at the tangled mess of legacy code, and realise it'll actually take two months.

If you're lucky.

Two months of digging through the code that would make even AI Agent quit its job. You feel a sudden urge to drop all of this and start raising geese in some remote mountains. Instead, you grit your teeth and make yourself another coffee. You're going to need it.

It's not the first time. The legacy code gives you a headache for a long time already. But the last three times you brought up "refactoring", you watched your manager's eyes glaze over before he changed the subject to "more pressing priorities".

I've been there. Many times.

And I was angry and frustrated. Why don't they understand how bad things are? Why don't they understand that we need to fix it? Are they stupid?

They were not. Obviously. It was my fault. I did not know how to talk to them.

I eventually learned how to do this. How to pitch an idea to the leadership and convince them to invest in it. I learned it the hard way, making many mistakes along the way. Now, I want to share this knowledge with you, telling you what I wish someone had told me many years ago.

Story Time: Pitching Location System Rewrite

Back in the day, I was working as a Head of Engineering in the Real Estate Marketplace.

As you can expect from the Real Estate business, location search and related functionalities were at the very centre of our interest. We had big plans!

Unfortunately, the location system we used did not know about those plans. It was an old, legacy mess that my engineering team was struggling to keep afloat. They did not even want to think about building advanced features on top of it. But the leadership was pushing for more, business critical features.

We needed to do something.

We sat down and drafted a new location system. Better, simpler, flexible, easy to extend with new features. But implementing it and replacing the legacy one was not a trivial task - it required time and resources. We needed to convince the upper leadership to allocate a team to that project and modify the planned product roadmap. Not easy, given the tight timeline and competitive market.

I needed to pitch our idea to the leadership and get them on our side. I've prepared a PitchDoc.

First, I reviewed the planned product roadmap for the locations to check what engineering work is needed to implement it.

Next, I described the issues with the legacy system, focusing exclusively on how those issues would prevent us from implementing the roadmap and achieving our business goals. Not a single word about technical debt or "ugly code".

I focused entirely on missing abilities, incompatible data and a compromised roadmap and user experience. I also highlighted how, due to the inherent complexity of the old system, the implementation time would be significantly higher for any work touching it.

Finally, I described possible solutions.

One option was to invest in the legacy system, modernise it and remove flaws that were blocking us.

The second was to implement a new location system from scratch, based on modernised assumptions and new tech.

Both plans were backed up by a high-level project plan, required resources, a migration plan and an estimated timeline.

I shared the PitchDoc with the leadership and scheduled a meeting to discuss the details. In the meeting I went through the key highlights of the proposal, stating that my recommendation, based on the research I did, was to implement a new system.

They asked a few questions, especially about the project plan, and after the discussion, they gave me a green light to proceed with the project and prioritise it as our main point of focus for the next few months.

Great success! 🎉

Notice that in this story, I never once said anything about technical debt or refactoring. All the discussion was about what we need to do to achieve the company's strategic goals. What we, as an engineering team, have to do to deliver our product roadmap as efficiently as possible.

Looking back, that success wasn't luck. I'd stumbled onto a formula that actually works. I started using the same approach for every technical pitch, and it kept working. Turns out there's a specific pattern to getting leadership buy-in, and I've refined it into a framework I want to share with you.

How to Pitch Your Idea to the Leadership

This experience taught me a simple but powerful approach. Every successful technical pitch I've made since, follows the same three-part framework:

• Why - The business problem I'm solving
• What - The solution I propose
• How - High-level execution plan

Pitching is a lot like selling. Good sellers create demand by solving problems their stakeholders have. To do that, you need to understand them.

Step 1: Know Your Audience

The first and most important realisation was that previous failures to prioritise the technical debt were my fault. I did not communicate it properly. I was talking to senior leadership like I was talking to my peers, fellow engineers. No surprise that I failed to convince them!

The first rule of good communication is "understand your audience!" But it took me many failed attempts to understand that engineers and executives are wired completely differently.

We think about code quality, technical elegance, and long-term system health. They think about quarterly targets, customer retention, revenue, and what they'll report to the board next month.

This isn't because they don't care about quality - they're simply playing a different game.

Usually, the more senior the leadership, the less they care about technical details. They don't care what version of React you use. Sadly.

Terms like "reducing technical debt" are too vague for them. A successful pitch demonstrates how your technical issues relate to their business challenges and how it helps them solve it.

In short:

What makes executives say yes - Clear ROI, reduced business risk, competitive advantage, and solutions to problems that keep them awake at night.

What makes them tune out - Abstract concepts, technical jargon, and requests without a clear business impact.

Step 2: Align with Company Goals

Company strategy is like a complex, collaborative puzzle. When pitching your idea, be the person who says, "I found the missing piece you need!", not the one dumping pieces from a different puzzle onto the table.