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Transformation roadmap

A transformation roadmap is a step-by-step plan guiding an organization through major changes, showing the phases and actions needed for success.

Most people hate change. Leaders know they need it. Teams who've seen failed changes want to run away from it. Everyone knows they must change, but no one wants to talk about it. But here's the pickle:

Companies that don't change die.

You're probably here because you want to change how your team or company works. And this needs a profound change. Transformation isn't about yet another restructuring or changing your Jira workflow. Transformation is about changing how your people think and work together. It's mostly mindset.

Great transformations create extraordinary results. They set you up for success. Companies grow faster and waste less money. Teams become stronger and more creative. Customers get better products and stay longer. Work becomes more fun, and people want to stay.

I didn't get my biggest promotions from running the best projects. I got them because I could create changes that brought the most value to the company. Here's how I went from engineer to CTO and board. That's often true for others too—leaders who drive significant changes move up fast. Managers become directors. Directors join executive teams. VPs step into board rooms.

Not gonna lie—it's hard work. But that's why it matters so much. And it doesn't stop. Just when you think you've fixed everything, three new problems pop up. Your competitors keep changing. Your customers want new things. Your teams need better ways to work.

Some leaders look at this and freeze. Others talk about change but keep doing things the old way. But the best ones? They dig in. They look for what needs to change next. They bring people along, even when it gets tough. And they do this over and over again. Not because they love change. But because they know that's what keeps a company alive.

Change is the only constant.

So, let's talk about the change.

What is Transformation?

I define transformation as a substantial change in how you create and deliver customer value. I'm not talking about the surface stuff like changing processes or buying new tools—those are just expensive band-aids. Real transformation reshapes how teams think, operate, and work together. It changes what gets measured, how decisions get made, and what behaviors get rewarded.

Want to know if you're really transforming? Watch what your teams do when no one's watching. True transformation happens when a team that used to wait for orders starts solving customer problems on its own, when a company that shipped twice a year now releases weekly, and when leaders stop asking for detailed plans and start asking about customer feedback instead.

What challenges does this help with?

I'd put Transformation roadmap on your radar and read on, if you're facing these challenges:

  •

    Failed transformations occur when attempts to adapt or improve a product or process result in setbacks or do not achieve the desired outcomes. Learn more

  • Your teams have no decisions about what they’re building or even how they’re building. They seek approval for most things. Learn more

  • Low employee motivation occurs when team members lack enthusiasm and drive to effectively contribute to product development efforts. Learn more

  • The most common issues within the organization. You probably won’t be able to get rid of this, once you have a scale, but you can (and should) try to fight it as hard as possible. Learn more

  • Too many team dependencies can slow progress, as teams must wait for each other to complete tasks before moving forward. Learn more

What Actually Changes?

Look, changing stuff is messy. You can't just change one thing and hope it works. When I help companies change, we look at five significant areas:

  1. Culture - This isn't about ping pong tables or free lunch. It's about how people work together, make decisions, and solve problems. If you don't change this, nothing else sticks. No fancy framework will help you.
  2. People & Teams - Sometimes you need different skills. Sometimes, you need the same people working in new ways and new structures. And yeah, sometimes you need new people who already get it.
  3. Strategy - Most companies claim they have strategy. My eyes are dead after seeing too many PowerPoint presentations about big ambitions of making billions of dollars and zero plan for doing it or getting there. Good strategy defines why you exist, where you want to be in a couple of years, and how you want to get there.
  4. Discovery - Most companies suck at figuring out what to build. They guess. Or worse, they build whatever the loudest person wants. Good discovery means really understanding your customers' problems.
  5. Delivery - Good product teams ship consistently. Building stuff isn't enough. You need to get it to customers fast, learn what works, and fix what doesn't. All while keeping the lights on.

Why Bother?

Good transformations bring the real impact. Here are the example outcomes from one transformation I helped with (B2B, SaaS, CEE, measured vs 12 months before):

  • 68% faster time-to-market
  • 3x higher employee satisfaction
  • 35% reduction in development costs
  • 2.5x better customer retention
  • 50% fewer production incidents

Those aren't small improvements. Those are game-changers. These translated to many millions of dollars. These changes compound. Do not compromise on having some fancy labels of being an agile company. Expect real, material change in critical metrics that matter.

Transformation Roadmap: Getting Started

70% of transformations fail (source). Most of them fail for the same reasons. They try to change everything at once. They forget about the people. They measure the wrong stuff. I've seen this movie before, and trust me, you don't want to be in it. That's why you need a roadmap.

What's a Transformation Roadmap, Really?

Look, everyone loves talking about roadmaps. But most of them are just fancy PowerPoint slides that end up on some shared drive and are never to be seen again. A real transformation roadmap is more like a battle plan - it shows you where to attack first, where you might face resistance, and most importantly, how to know if you're actually winning.

Want to know what makes a good roadmap? It's not the pretty boxes or the clever names for phases. It's about answering three questions that matter:

  1. Where are we really at? (Not the sugar-coated version you show the board)
  2. Where do we need to be? (With real numbers, not fluffy "be the best" nonsense)
  3. How do we get there? (The actual steps, not consultant-speak)

Here's exactly how I break this down when I help companies transform:

How to implement it step-by-step

  1. Add Transformation roadmap to your deck :
    (unavailable until launch)
  2. Communicate the start of work on the practice to the team.
  3. Assemble strike team to work on the practice.
  4. Establish success metrics you want to achieve and the assumed time horizon of when you want to reach them.
    Name Definition Current value Wanted value Wanted by when? Importance
    Conversion rate Percentage of leads that convert to paying customers 2.50% 4% Q4 ★★★★★
    Customer satisfaction Average customer satisfaction score (CSAT) 7.5/10 8.5/10 Q2 ★★★★☆
    Time-to-market Average time to launch new products/features 100 days 5 days (68% faster) Q4 ★★★★☆

    Example list of metrics you can use is provided by framework.

  5. Define the transformation
    • Define a team of people leading the transformation.
    • Define the list of teams affected.
    • Define the list of key stakeholders.
    • Define initial budget
  6. Assess where you are. Take an honest look at where you are today across processes, behaviors, and capabilities - looking for evidence rather than taking what people say at face value. Create a document about what works and what doesn't, like so:

    If you want to know what to look for and how success should look like, check the checklist I prepared.

    Example:

  7. Prioritize problems

    Now take the problems you found, prioritize them and decide on timing. I like to use Now, Next, Later format.

    • Now should contain precise, well-defined items that are committed for the next quarter,
    • Next should include items that are planned but may need more discovery for the following 2-3 quarters,
    • Later should encompass strategic initiatives and ideas that need significant research or depend on earlier deliverables.
  8. Define and prioritize solutions

    For the problems you decided to fix Now, generate tactics. Then prioritize them (I like to score Impact and Easiness) and decide on time horizons (Now, Next, Later again).

    That's your tactical view.

  9. Repeat

    Regularly review and adjust your roadmap based on actual results and new information, typically on a quarterly basis. Update your metrics, reprioritize, and adjust timelines.

PS: If you need help with implementing the Transformation roadmap, contact me. I have 20+ years of commercial experience working with bigger and smaller companies, upgrading product, design, and engineering teams to the next level. I can also connect you with experts on this subject.

Transformation roadmap Template

Transformation roadmap Template

This template helps you define transformation metrics, audit your organization, and build a prioritized list of changes to your current ways of working.

Download links:

Tips That Actually Work

Things I've learned the hard way (usually by screwing up first):

  1. Make It Real, Make It Now

    Want to know the fastest way to kill transformation? Make it feel distant and abstract. I once watched a company spend six months discussing "cultural evolution" while its competitors ate lunch.

    Instead, pick something your teams can start doing differently tomorrow. One team I worked with started by changing just one meeting - they turned their status update into a problem-solving session. Within weeks, other teams wanted to copy them. That's the dynamic you want to aim for.

  2. Find Your Islands of Success

    Stop trying to boil the ocean. Find the teams who are hungry for change and let them run. I worked with a company where one small team started releasing weekly instead of quarterly. Their success made everyone else curious. Six months later, half the company had followed their lead. No special mandates needed.

  3. Show Progress Like a Boss

    Most transformation metrics suck. They measure activities, not outcomes. Want to know if you're winning? Watch what people do when no one's looking. Are teams starting to make decisions without waiting for permission? Are they talking to customers more? Those are your real metrics. Put them on a wall where everyone can see them.

  4. Build Your Army of Believers

    You need people who'll fight for change when things get tough. And they will get tough. In my last transformation, we found our best champions in unexpected places - a quiet developer who turned out to be a brilliant coach and a skeptical manager who became our biggest advocate once she saw early results.

Common Mistakes (And How to Dodge Them)

Let's talk about ways people mess this up.

  • The Speed Trap

    You're excited. You want everything to change now. Stop. Breathe. The fastest way to change everything is to start by changing one thing well. I've seen two-week pilots create more lasting change than two-year transformation programs.

  • The Ivory Tower Blueprint

    Planning your transformation in a conference room with just the executives? Good luck with that. Your best ideas will come from the people doing the work. One of my most successful transformations started when we shut up and listened to customer service reps for a day.

  • Metrics Mirage

    Measuring everything because you can? That's just noise. Pick a few metrics that matter. You don't need 25 transformation KPIs; three key ones are enough to create focus and clarity.

  • Change Fatigue Flip-off

    "They'll get used to it" is not a strategy. People get tired of constant change. Do not let transformation derail because you forgot that teams need time to breathe between major changes.

How to Sell This to Your Boss

Even the best transformation plan dies without support from above. Here's how to get it:

Speak Their Language

First thing's first - drop the transformation jargon. Your boss doesn't care about frameworks or the latest buzzwords. They care about outcomes. Instead of trying to look smart by talking about "agile methodologies," show your boss how our changes would cut infrastructure costs by 40%. Now we were speaking his language. Focus on hard numbers: cost savings from fewer mistakes, revenue boost from faster delivery, and improved customer retention from better quality.

Start With Risk

Here's what gets every executive's attention: the risk of doing nothing. I once worked with a company that ignored transformation until its biggest competitor started shipping features twice as fast. By then, it was almost too late.

Show your leaders what's happening in your market. Point out the companies that are eating your lunch because they adapted faster. Big tech companies are where they are for a reason - they were able to change and create an environment where they can consistently innovate on behalf of their customers. Even better, bring examples of similar companies that failed because they stuck to their old ways too long. Nothing motivates change like the fear of becoming irrelevant.

Make It Tangible

Leaders hate vague plans. They've seen too many transformation initiatives that sound good but go nowhere. Instead, come armed with specifics. Pick a pilot area where you can prove your approach works. Show exactly what metrics you'll track and how you'll measure success. Lay out a detailed 90-day plan that shows what will change and when.

I once turned a skeptical CEO into our biggest champion by showing him exactly how our transformation would help us recapture the market share we were losing to more agile competitors. The key? I didn't just tell him, "Trust in agile transformation, plz"- I showed him how.

Conclusion

Remember something crucial: transformation isn't about following some perfect plan. It's about having a clear direction and being smart enough to adjust as you learn. The best roadmap isn't the prettiest one - it's the one that gets your company where it needs to go.

Your move now. Take these ideas, adapt them to your world, and start moving. Because here's the truth - no one will remember your beautiful transformation plans in a few years. They'll remember what changed.

And hey, remember why you started when it gets tough (it will). You're not just changing processes or tools. You're changing how people work together to create something better. That's worth fighting for.

I keep my fingers crossed!

Linked cards

Here are other practices related to Transformation roadmap:

  •

    Value stream is a mid-to-long-lived area of work that company find valueable. It could be a problem, it could be persona, it could be market segment. Learn more

  • Team Topologies is an approach for organizing people in tech companies into effective teams. Most known for introducing four team types and three interaction modes, it aims to reduce team dependencies and manage cognitive load. Learn more

  • OKR, or Objectives and Key Results, is a goal-setting framework that helps teams define clear objectives and track measurable outcomes to ensure alignment and progress. Learn more

  • Empowered Autonomous Teams can decide what to build to solve they problem they're being assigned, without any excessive oversight. Learn more

  • Innovation over predictability emphasizes the value of creative, novel solutions over routine, predictable outcomes in product development. Learn more

  • Your customers are your business therefore, obsessing over them must be at the core of your culture in order to succeed. Learn more

  • Product strategy provides the logical sequence of big bets (projects, value streams) that will take you to Product Vision. Learn more

Hope that's useful!

Piotr Kacała