Crafting a Technical Strategy That Actually Works

San Diego, USA – November 2025 – Photo by Kevin Goldsmith

It’s planning season for most companies. By the time November rolls around, the board decks are being assembled, the budgets are being scrutinized, and every technology leader, from the C-suite to frontline management, is being asked some version of the same question: Where are we headed next year?

Regardless of your scope, having a clear technical strategy is crucial. And not just a mental model you carry around in meetings; a documented strategy your team can reference, question, and ultimately internalize. The absence of that clarity is one of the fastest ways for an engineering organization to drift off course.

Why documenting a strategy matters

When there’s no shared strategy, every team ends up making decisions based on personal taste, excitement about a trend, or something they saw in a conference talk. Without a shared North Star, those decisions diverge quickly. I’ve seen it firsthand: people heading in different directions, not because they disagree, but because no one ever explained where the organization is trying to get to.

Misalignment shows up everywhere. Architectural choices start reflecting old org structures instead of future goals. Product partners become frustrated because engineering appears to be prioritizing strange work. The business begins to question why teams are focused on internal rewrites instead of delivering customer-facing value. From the outside, it can look like chaos.

The hard truth is that most of these problems aren’t technical; they’re leadership failures. They come from not taking the time to define, document, and communicate the strategy.

What a good strategy looks like

A technical strategy doesn’t need to be fancy, but it must align with the business. If the business wants to enter new markets, your strategy should account for internationalization, payments, compliance, and scale. If the company plans to grow revenue by 10×, your architecture needs to be able to handle a 10× load. If you’re betting on expanding into adjacent industries, you should know whether your current systems or your current talent can support that.

A useful strategy has a few characteristics:

It’s coherent. Not a bag of unrelated goals. All the pieces should pull in the same direction.

It’s understandable. Anyone in your org should be able to read it and explain it to someone else.

It’s written at the right altitude. Too detailed, and it becomes a roadmap. Too vague, and it becomes meaningless. The test is simple: can people use it to make better decisions without needing your permission?

It’s a living document. The world shifts—the business shifts. Your strategy should update when reality does, but not so often that no one can keep track of it.

And, this is important, you should ground it in both where you are and where you need to go. Strategy isn’t about predicting the future; it’s about preparing your team to meet it.

Start by working backwards

Amazon made “working backwards” famous, but the underlying idea is helpful in any organization: imagine the future state, then figure out what needs to be true to get there.

If everything were going well two years from now:

  • What would your architecture look like?
  • What pain points would be gone?
  • What capabilities would your team have?
  • What new markets or products would the business be ready for?
  • What skills would you need in the team that you don’t have today?

Once you can visualize that world, you can start mapping backwards to the key technical bets that move you in that direction. Those bets might look like:

1. Moving toward event-driven architecture

2. Eliminating or isolating legacy systems

3. Prioritizing observability

4. Making large structural changes like cloud migration

5. Reorganizing teams around more scalable patterns

6. Reskilling people as technology evolves

Each of those bets should be tied directly to a specific business outcome. Otherwise, it’s just engineering for engineering’s sake.

Don’t create strategy in a vacuum

If you’re in the C-suite, validate the strategy with your peers first. Make sure the rest of the executive team understands and agrees with it. They may have expectations you aren’t aware of, or strategic initiatives that need your support.

If you’re a VP, director, or EM, share your draft with your cross-functional partners. Product and design should understand how the strategy shapes what you will and won’t do. Their strategy should align with yours, and yours should align with theirs.

When strategies diverge, teams drift. When they align, the work feels almost frictionless.

Communicate relentlessly

Communication is where most leaders fail, myself included at times. Sharing the strategy once is meaningless. Most people won’t internalize it until they’ve heard it repeatedly, in different contexts, tied to real decisions.

Put it in your all-hands. Reference it during project kickoffs. Use it when explaining tradeoffs. Make it part of onboarding. Ask teams to explain how their proposals align with it.

The goal is to make the strategy the frame everyone uses to make decisions. When that happens, you suddenly spend far less time correcting teams and far more time accelerating them.

How you know the strategy is working

You shouldn’t need to police architectural choices. Teams will make decisions that generally align with your intent.

You should see less rework, fewer surprise escalations, and fewer “Why are we building this?” debates.

Product partners should understand why certain internal work matters.

Cross-team integrations should become easier because everyone is working towards the same future, not the one in their own heads.

Your platform should scale as the company scales, ideally without drama.

And, most importantly, people should feel like they understand the purpose behind their work. Purpose and autonomy are two-thirds of what drives intrinsic motivation. A good strategy gives people both.

Final thought

A technical strategy isn’t a crystal ball. It’s not about outsmarting the future. It’s about giving your team the clarity and context to face that future together, and build well along the way.

If you’ve been putting off writing your strategy document, now is a good time to make progress. Your team will thank you later, and honestly, your future self will too.

Originally published in my newsletter on November 16, 2025

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