What Story is Your Roadmap Telling?
7 Tips for CTOs & Technology Leaders to Nail Their Story
👋 Hello Technocrats!
Every technology leader has a roadmap — and like it or not, that roadmap is telling a story. It could be a good story, a bad one, or just plain ugly. The key is to take control and intentionally craft a narrative that serves you and your business, instead of becoming a victim of a story 📖 you didn’t shape.
Cheers & let’s dive in!
Bobby
I remember the first time I spent a huge amount of money on an Engineering roadmap.
It was something north of $30 million.
It felt exhilarating and terrifying all at the same time…
On one hand, it was an incredible feeling to finally have real resources behind the roadmap.
On the other hand, I knew the pressure was on not just to spend the money, but to turn it into something meaningful.
Of course, I had to get a big return on the investment. Everyone expects that.
But it hit me even harder that I was also telling a very important story, to the Board, to my CEO, to my team, even to customers — about what kind of company we were becoming.
The big budget decisions I made weren’t just about funding projects. They were shaping the narrative of what we valued, what we prioritized, and where we were heading.
So Who’s Reading the Story? 👀
The short answer is, everyone.
When you invest in Engineering, not everyone will see the actual budget numbers — but they will *feel* the impact of how that money was spent.
Board
They are reading between the lines, asking if you are building long-term enterprise value or just burning cash for short-term, finite wins.
Customers
They experience the outcomes directly — whether it’s new features, better performance, or bugs that never seem to get fixed.
Executive Leadership Team (ELT)
They are watching to see if your investments are aligned with the company’s strategic goals, or if Engineering is drifting into its own world.
Team / Staff
Your team feels how the money moves. Are you funding innovation and giving them space to do great work, or are they stuck in endless maintenance mode?
Partners
They can tell if you are building a stronger platform for future growth, or if you are making risky bets that might put the relationship (and their investment) at risk.
Spending $30 Million on Engineering 💰
Here’s an example of how money can be spent in Engineering and the story you could inadvertently be telling to stakeholders.
$6M on Innovation
This is where you fund big bets — new platforms, AI initiatives, future product lines, and experiments.
Spending 20% of your budget here can tell the Board that you are serious about long-term growth and market leadership.
It can show customers that new capabilities are coming.
But it can also make the ELT nervous if they see innovation efforts disconnected from near-term business goals.
The team might feel energized by bold projects — or confused if priorities shift too often.
Partners may wonder if you are distracted from strengthening your core product.
$7.5M on Maintenance
This is where you invest in expanding your core offering: new modules, enhancements, and product differentiators.
Spending 25% here tells customers you are listening and evolving. It gives sales and marketing new ammunition.
The Board may see it as proof you are keeping pace with the market.
But the ELT may worry if features feel scattered or non-strategic.
Your internal teams might feel proud of progress — or frustrated if quality or cohesion starts to slip.
Partners might see opportunity if the roadmap aligns to their needs, or risk if it feels unfocused.
$9M on Maintenance
This is the work nobody sees: infrastructure upgrades, system hardening, performance improvements, scaling efforts.
Spending 30% of your budget here can reassure the Board and ELT that you take stability and reliability seriously.
Customers may simply notice that the product "just works" better — or not notice at all, which is sometimes the goal.
The engineering team usually appreciates investments here, because it makes their daily work easier and reduces firefighting.
However, if maintenance dominates too much of the spend, stakeholders may start to question whether the platform is aging faster than the business is growing.
$6M on Tech Debt
This is the behind-the-scenes work of cleaning up past shortcuts: refactoring, re-platforming, and re-architecting.
Spending 20% here can demonstrate to the Board and ELT that you are protecting the company’s future scalability and agility. It can also quietly raise concerns if they feel like they are paying twice for mistakes that were already "done and shipped."
Customers rarely notice tech debt work directly, unless it improves speed or reliability.
The team often sees it as a long-overdue investment in their sanity and velocity.
Partners may be indifferent — until neglected tech debt starts to limit integrations or performance.
$1.5M on Bug Fixes
This is the work of fixing production issues, polishing rough edges, and responding quickly when things go wrong.
Spending 5% here tells customers that you care about their experience and take quality seriously.
The ELT usually appreciates rapid responsiveness, but may worry if the bug count stays stubbornly high.
The Board likely expects strong fundamentals, so too much visible spend here could signal process issues.
The engineering team often sees bug-fixing work as important but draining if it overwhelms feature delivery.
Partners view high responsiveness positively — but too many bugs may still hurt confidence in your platform.
As you can see, every stakeholder reads your engineering investments through their own lens.
Tips on Getting Your Story Straight 💁♀️
When you are operating at the big leagues of Engineering Management — whether you are a CTO, VP of Engineering, or Head of Technology — getting your investment story straight is critical.
At this level, you are responsible for the narrative that ties your technical investments back to business value, strategic goals, and company health.
Everyone from the Board to your own engineers is watching how you allocate resources, not just whether you "get things done."
A scattered or confused investment story will erode trust.
A clear, intentional story will strengthen your influence and elevate your leadership in the organization.
You do not have to be perfect.
But you do have to be clear, intentional, and communicative about the story you are telling with the money you are spending.
1. Don’t just fund projects, fund business outcomes.
Tie every investment back to a strategic outcome
When you present major initiatives, clearly link them to company goals: revenue growth, customer retention, margin expansion, market entry.
If you cannot tie an initiative back to a bigger business priority, it probably should not be on the roadmap.
2. Balance today’s needs with tomorrow’s ambition.
A strong roadmap serves two masters: what the business needs *now* and what it will need *next.*
If you over-index on maintenance and debt, you look defensive.
If you over-index on innovation, you look reckless.
The story you often want to tell is: "We are strong today, and we are building an even stronger tomorrow."
3. Be ruthlessly clear about tradeoffs.
Every dollar you spend in one area is a dollar you are *not* spending somewhere else.
Good leaders make these tradeoffs explicit: "We are choosing to invest less in Feature X this quarter to tackle Tech Debt Y."
Bad leaders let tradeoffs happen by accident — and lose control of the story.
4. Keep communicating ROI even if it’s imperfect.
You do not need to build a perfect financial model for every initiative.
But you do need to show stakeholders that you are thinking in terms of returns, not just outputs.
Simple framing like, "This platform investment is expected to unlock $5M in new upsell potential," goes a long way toward building a credible story.
5. Watch for “Drift” in your story.
Your roadmap story can start strong — and then slowly drift as projects expand, maintenance grows, or priorities shift.
Regularly recheck: "Is the story we are telling with our spend still aligned with the business we want to become?"
Drift kills trust while course correction earns respect.
6. Make the intangible investments tangible.
Investments like Tech Debt, Maintenance, or Developer Productivity often feel invisible to non-technical stakeholders.
Your job is to make them real.
Explain them in business terms: faster delivery times, better customer experiences, stronger platform stability.
If you cannot explain it clearly, expect it to get questioned or cut.
7. Teach your team to tell the story too.
It is not enough for you to understand the story.
Your leadership team, your senior engineers, and even your frontline managers should see how their work ladders up to the bigger narrative.
An organization that understands the "why" behind the spend will execute with more alignment, urgency, and pride.
Closing Thoughts 💭
As a technology leader, crafting the story of your roadmap should be something you are deliberate about spending time on.
Don’t just let the story be thrust upon you by the outside world or other stakeholders. Take control of the narrative (which benefits everyone).
The easiest way to start is to bucket your spend into different categories and then explain (to yourself, first) what each category will do for the business in terms of driving outcomes.
Remember, you can have multiple outcomes per category, especially if you have a large budget like I did.
I always make a deck for the story and then practice the narrative with various trusted people before taking it in front of stakeholders.
This is super helpful for fleshing out your thinking and prepares you for the next Board meeting, all hands call, or 1-on-1 with your CEO.
If you need help with any of this feel free to email me at bobby@technocratic.io
And in the meantime, keep the shark swimming! 🦈
Bobby