Why Leaders Must Own the Journey and Work ON the System — Not Delegate It

25.11.2025, By Stephan Schwab

Methodologies cannot be installed like software. Big-bang rewrites fail — Netscape and Borland learned this the expensive way. Arbitrary deadlines create panic, not progress. Real improvement requires a journey: developers learning better techniques in context, non-technical colleagues expressing requirements as testable specifications, and executives learning to read delivery signals directly rather than through filtered status reports. We embed with your teams, transfer skills, and step back when you're stronger — creating capability, not dependency. What follows explains why lasting delivery improvement comes from people learning to work better, not from following a branded framework's roadmap.

Three insights executives must accept:

  1. Process cannot be installed with a deadline. Your codebase reflects years of decisions and embeds vast domain knowledge. Improving it requires discipline and time, not heroics or rewrites.

  2. Improvement is a journey, not a destination. Like a car navigation system, you need current position, direction, and the next turn — not a rigid twelve-month roadmap.

  3. Skill uplift beats ceremony compliance. Developers learning TDD, teams mastering CI/CD, and leadership reading real metrics create lasting change. Methodology rituals create theater — or worse, friction that prevents learning by separating thinking from doing, rooted in the misconception that software development is construction rather than design and discovery.

When executives contact us, they sometimes expect a familiar pitch:

Here’s the framework. Here’s the roadmap. Here are the ceremonies.

They've heard it before. They know the script. And maybe this vendor does it better.

But that’s not what we offer.

We don't arrive with a branded methodology. We don't install processes and leave. We don't create certified coaches to enforce compliance.
  • We embed.
  • We work with code and people.
  • We uplift skills.
  • Our metric is software in the hands of happy users.

But make no mistake: we work on the system, not in it.

Though a Senior Developer Advocate spends significant time in the code and pairing with developers, this role is not another team member subject to organizational rules or process ceremonies.

We operate with the independence needed to identify and address systemic constraints — not get absorbed into the problems we’re there to solve. Don’t fire us for non-compliance - being non-compliant is likely what you are paying us to do.

And then we leave you stronger than we found you — not dependent on us.

The Problem with Methodology Installation

Most consultancies sell transformation as a package:

  • A maturity model to assess your current state
  • A roadmap to guide you through stages
  • Ceremonies to structure your days
  • Coaches to ensure compliance
  • Return visits to “measure progress”

It looks comprehensive. It feels safe. It’s expensive.

And it rarely works.

Here’s why:

Software delivery is not a manufacturing process that can be standardized. It’s a creative discipline requiring judgment, adaptation, and deep technical skill.

AI amplifies this creativity — when developers know what they’re doing.

We help teams use AI tools to increase creativity, speed of execution, and iterate faster. But make no mistake: AI will not replace competent developers. We’re here to make everyone a competent developer who can leverage AI effectively.

AI assistance is powerful in the hands of someone who can:

  • Judge whether the generated code is correct
  • Spot subtle bugs and security issues
  • Understand architectural implications
  • Write tests that validate the solution
  • Refactor effectively to maintain clarity

Without this foundation, AI becomes a faster way to create legacy code.

The same logic applies to methodology installation.

Installing a method might create the appearance of progress — more meetings, more artifacts, more vocabulary — but it doesn’t address the actual constraints:

  • Developers who’ve never written a test - first
  • Teams afraid to integrate their code frequently
  • Leadership making decisions based on status slides instead of runtime evidence
  • Architecture decisions that made sense three years ago but now strangle velocity

You can’t ceremony your way out of technical debt. You can’t standupify your way to continuous delivery.

Real improvement requires people learning to work better. And that happens through doing, not through following a script.

What We Do Instead

We engage with the people who do the work and those who lead them.

For Development Teams:

We don’t run training sessions in a conference room. We pair with developers on real production code.

We introduce techniques — TDD, ATDD, trunk-based development, CI/CD — in context, on their codebase, under their constraints.

We show them how to write tests that give confidence. How to integrate safely multiple times per day. How to deploy small changes that reduce risk.

For Non-Technical Domain Experts:

We help developers interact effectively with colleagues who bring market knowledge, customer insight, and subject-matter expertise.

We facilitate ATDD sessions where business analysts, product managers, and domain experts collaborate with developers to define executable specifications.

We show teams how to translate domain language into automated tests, so everyone — technical and non-technical — can see whether the software does what was intended.

This isn’t about teaching non-technical people to code. It’s about creating a shared language for describing what success looks like, and ensuring developers build what’s actually needed — not what they think was requested.

For Leadership:

If you run a software company, you need to understand how software gets made. You wouldn’t run a restaurant without understanding the kitchen. Software is no different.

We help leaders — engineering managers, architects, executives — see what’s actually constraining delivery:

  • Where integration friction is hiding
  • What deployment frequency reveals about confidence
  • How lead time variation signals process dysfunction
  • Why escaped defects point to test strategy gaps
  • Are we deploying more frequently with fewer incidents?
  • Is our lead time trending down or stuck?
  • Are features being used, or just shipped?

These questions don’t require a computer science degree. They require curiosity about how the work actually happens.

Leaders often feel trapped between:

  • Developers who speak in technical jargon
  • Project managers who filter bad news into optimism
  • Consultants who sell complexity as sophistication

We translate — not to shield you from the details, but to make them accessible.

We don’t replace your judgment. We give you better instruments to exercise it.

The goal isn’t to make you a developer. It’s to make you a leader who can have honest, fact-based conversations about delivery with your teams.

Don’t hide from us.

Seek dialog. Ask questions. Challenge our observations.

The worst thing you can do is stay distant and rely on filtered reports. We’re here to give you direct insight into what’s happening — not comfortable narratives, but reality you can act on.

Why This Approach Works

1. It addresses real constraints, not symptoms.

You don’t have a “people problem” or a “process problem.” You have specific technical and organizational constraints.

Maybe your test suite takes three hours to run, so no one runs it. Maybe your branching strategy creates integration debt that explodes during "merge week." Maybe your deployment process requires manual approval from five people, turning every release into a project.

These are fixable. But not by installing a ceremony.

2. It builds internal capability.

When we pair with developers, they don’t just watch us work — they learn to do it themselves.

When we coach leadership, they don’t become dependent on our translations — they learn to ask better questions and read evidence directly.

If after six months you need us the same way you needed us on day one, we’ve failed.

3. It respects your context.

We don’t arrive with a one-size-fits-all playbook.

We assess:

  • What’s already working (and protect it)
  • Where the highest-leverage improvements lie
  • What skills need uplift most urgently

Some teams need better test discipline. Others need deployment automation. Still others need clearer ownership and decision rights.

The solution is always specific. The method is always adapted.

4. It creates lasting change.

Dependency is the enemy of transformation.

If your improvement strategy requires permanent external coaching, it’s not improvement — it’s outsourcing.

We uplift skills so teams can continue improving after we leave.

We instrument delivery so leadership can see problems before they metastasize.

We establish feedback loops so learning becomes continuous, not event-driven.

What This Looks Like in Practice

We embed with teams on an at-will basis:

Observe how work actually flows. Identify the highest-leverage improvements. Pair with developers on real code. Uplift skills systematically. Instrument delivery so progress becomes visible. Step back when teams operate independently.

If we’ve done our job well, you don’t miss us when we leave. You’re just stronger.

Why This Isn’t a “Big Bang” — And Why That’s Good

Executives sometimes worry:

“This doesn’t sound like a complete transformation. Where’s the roadmap? Where’s the certainty?”

Here’s the truth:

Big-bang transformations fail precisely because they promise certainty.

Software delivery is uncertain. You’re building something that’s never been built before, for users whose needs evolve, in a market that doesn’t wait.

Pretending you can plan that into certainty is theater.

What you can do:

  • Reduce lead time so you learn faster
  • Increase deployment frequency so you adapt faster
  • Improve test coverage so you move with confidence
  • Clarify ownership so decisions don’t stall

These improvements compound. Faster learning enables better decisions. Better decisions compound into competitive advantage.

But they don’t follow a maturity model. They follow reality.

The Test: What Happens When We Leave?

Here’s how to know if an engagement was successful:

Ask these questions six months after we’re gone:

  • Are features being adopted by users, or just shipped and ignored?
  • Is revenue per developer trending up?
  • Are customer satisfaction scores improving?
  • Can you respond to market changes faster than before?
  • Are you spending less on operations while handling more volume?

If the answer to most of these is yes, the capability transferred.

If the answer is “we need to hire more coaches,” something failed.

Why We’re Not Competing with Methodology Consultants

Some executives assume we’re just another flavor of consultant.

We’re not.

Management consultants focus on organizational structure, governance, and strategy. That’s valuable work.

We focus on software delivery:

  • How developers work
  • How code flows to production
  • How leadership sees what’s happening

These are complementary.

When a methodology is already in place, we work with it.

We don't arrive to fight turf wars over narrative or frameworks. We're advocates for our client — from the technical side. Our job is to enable success through delivery.

If management consultants are present with their methodology, we collaborate. We make their frameworks executable by connecting them to real delivery signals.

If a method exists but consultants have left, we help you make it work better — or simplify what’s gotten bloated.

When new methodologies are being considered, we assess and advise.

If executives are evaluating a new framework or transformation approach, we will provide technical due diligence.

This isn’t optional — it’s part of our responsibility to you.

We will advise against approaches that:

  • Create artificial separation between thinking and doing
  • Treat software development as a manufacturing process
  • Add ceremony that obscures rather than reveals constraints
  • Prioritize compliance over learning

Our obligation is to our client’s success, not to any methodology’s brand.

If approaches become incompatible with effective delivery, we step back.

We won’t fight organizational battles over methodology.

If management insists on approaches fundamentally incompatible with our statement of work — approaches that will predictably harm delivery or create the conditions that drive developers to leave — we’ll conclude our engagement professionally.

This isn’t about winning an argument. It’s about integrity and protecting the people we’re there to serve.

Staying in a situation where our technical guidance is systematically overridden creates worse outcomes:

  • It confuses teams about what actually matters
  • It creates conflict that erodes trust and psychological safety
  • It often leads to the best developers leaving rather than fighting

We’d rather step back cleanly than contribute to that dynamic.

The Uncomfortable Truth

Beyond methodology debates, improving software delivery requires four things many organizations resist:

1. Senior leaders must own the transformation.

You cannot delegate this work to consultants.

You are the leaders. You set the pace. You protect the vision. You make the decisions. We provide help and guidance — technical expertise, delivery instrumentation, skill transfer.
We help you create and refine that vision by showing you what's actually constraining delivery. We give you better instruments to see reality. We coach you to ask better questions.

But the transformation is yours to lead, not ours to install.

If you’re looking to hand responsibility to an external vendor with a roadmap, we’re not the right fit.

2. Senior leaders must learn to see the work.

You cannot delegate understanding.

If you don’t know why your teams struggle to deploy, or why lead times vary wildly, or why “done” never seems to mean “shipped,” no consultant can fix that for you.

You have to look.

3. Developers must be allowed to improve their craft.

You cannot ceremony your way to technical excellence.

Developers need time to learn test-driven development. To refactor legacy code. To automate what’s manual. To experiment with better architectures.

If your process doesn’t protect space for this, your process is the problem.

4. Improvement is a journey, not an installation with a deadline.

Executives often create artificial urgency: “We need this fixed by October.” “The board expects transformation by Q2.” “If we don’t modernize now, we’re dead.”

This pressure is understandable. But it’s also dangerous.

Your codebase didn’t arrive at its current state overnight. Years of decisions, constraints, and trade-offs created what exists today. More importantly, your codebase embodies vast domain knowledge—business rules, edge cases, regulatory requirements, customer behavior patterns — accumulated through years of learning what actually works.

This knowledge isn’t just in documentation (which is often outdated or missing). It’s encoded in the code itself: how data flows, what validations exist, which assumptions are baked into algorithms.

Improving the codebase requires time and discipline — it cannot be installed or rewritten by heroics. And any rewrite must preserve and distribute this domain knowledge across the organization, or you’ll rebuild yesterday’s problems tomorrow.

The history of software is littered with expensive failures from executive impatience:

  • Netscape decided to rewrite their browser from scratch. The rewrite took three years. By the time they shipped, the market had moved on. The company never recovered.
  • Borland attempted to rewrite Quattro Pro. The project collapsed. Competitors shipped incremental improvements while Borland burned resources on a replacement that never materialized.
  • Countless companies have formed “expert rewrite teams” only to discover that replicating years of domain knowledge and edge-case handling is harder than anticipated. Meanwhile, the existing system continues accumulating technical debt because no one is maintaining it.

The pattern is consistent: Big-bang rewrites fail. Arbitrary deadlines create panic, not progress.

What works is steady, visible improvement:

  • Fix one integration bottleneck and measure the lead time change
  • Improve test coverage incrementally so confidence grows
  • Automate one manual deployment step at a time
  • Refactor sections of code as you work on them, not in isolation

The destination matters less than the trajectory.

If you’re improving every month, you’ll get where you need to be. If you’re setting deadlines and panicking when they slip, you’ll burn out your best people chasing an arbitrary date.

Patience isn’t passivity. It’s the discipline to value lasting progress over theatrical urgency.

What We’re Really Offering

We’re not selling a method. We’re not selling a transformation.

We’re offering partnership in building capability.

We bring:

  • Decades of hands-on software delivery experience
  • Proven techniques that reduce friction and increase throughput
  • The ability to translate between technical reality and executive decision-making
  • A focus on making ourselves unnecessary

You bring:

  • The context we cannot have
  • The authority to remove organizational obstacles
  • The willingness to learn alongside your teams

Together, we create lasting improvement.

Not because we installed a process, but because people learned to work better.

The Choice

You can install a methodology:

  • Buy the framework
  • Train the method champions
  • Follow the ceremonies
  • Hope it works

Or you can build capability:

  • Engage experienced practitioners
  • Uplift your teams’ skills
  • Instrument your delivery
  • Learn to see what’s happening

The first path creates dependency. The second creates capacity.

Choose accordingly.

Contact

Let's talk about your real situation. Want to accelerate delivery, remove technical blockers, or validate whether an idea deserves more investment? Book a short conversation (20 min): I listen to your context and give 1–2 practical recommendations—no pitch, no obligation. If it fits, we continue; if not, you leave with clarity. Confidential and direct.

Prefer email? Write me: sns@caimito.net