Why Your Transformation Might Not Be Going as Well as You Expected… And What to Do About it
“Things need to change.”
“The way we’re serving our customers is ineffective.”
“Our approach to product management could use some help to achieve state-of-the-art status.”
Any of these statements sound familiar?
These are sentiments I often encounter from (product) leaders who have attended a workshop, training, or offsite. Whether it was an SVPG workshop, a Swiss Business School Executive Education course, or a networking conversation, some little spark ignited what’s now become a burning desire for transformation.
And as a product leadership coach, I often end up participating in or guiding this transformation work.
But this can be a major undertaking that’s riddled with ambiguity and confusion.
My first task is generally to help my clients achieve more clarity on the topic of transformation. I urge them to reflect on tough questions, including:
Why did this topic resonate so well with you in that particular workshop/course/conversation?
What do you think needs to change?
What is the desired “end state”? (Though I don’t think one is ever “done” with improving ways of working)
How would folks in your organization work differently in the future?
How would that serve the customer and the business better?
As you can imagine, you don’t simply answer these questions once and call it a day. This quickly becomes a recurring topic. Since I’ve had the opportunity to participate in many of these ongoing conversations, I wanted to take a moment to share what I’ve learned.
If you’re also feeling compelled to begin a journey of transformation, I’d encourage you to start here. In this article, I’ll outline a few framings and insights that have helped my clients and may also help you increase your chances of success.
Four types of transformation—clear wording and definitions help!
Part of the difficulty with the word “transformation” is that it can be too broad and vague. It means different things to different people.
This is why I recommend starting with clear wording and definitions. You want to ensure that you’re all talking about the same things.
Note that while these ideas are distinct, they are often related. You may end up working on each type of transformation separately or any combination of them together. Each one addresses unique aspects of organizational evolution, but they all share common threads that, when woven together, can guide your efforts toward a coherent and impactful transformation strategy. Let me explain:
Agile transformation: Focuses on instilling an agile mindset across teams, emphasizing flexibility, responsiveness, and delivery efficiency. (I’m deliberately not talking about delivery frameworks like SCRUM or SAFe here because that’s not all there is to a true Agile transformation!)
Product mindset/product operating model transformation: Looks at questions like “How do we build, ship, and market our products?”, “How do we decide which customer problems to solve and how to solve them?” or “How do we find new meaningful customer problems to solve?” This encompasses broad areas including finding directional clarity (product strategy), opportunity assessment and discovery, delivery and product optimization, product culture, and product operations. It involves aiming for a holistic rethinking of how products are conceived, developed, and brought to market. (Marty Cagan and his SVPG peers just released a book on that topic that you might want to read.)
Ways of working transformation: I know. The name sucks! But I couldn't find a better one so we have to work with this for the moment. This transformation targets the cultural and operational aspects of your organization, from meeting cultures and leadership styles to embracing remote, distributed, or hybrid work environments. This may also include the New Work concept (originally popularized by Frithjof Bergmann), which emphasizes meaningful, autonomous work that aligns with personal fulfillment and self-realization, challenging the traditional task-oriented approach to work.
Digital transformation: Revolves around redefining business models through digital innovation, focusing on creating value for customers leveraging modern digital products and business models. (BTW, this is often confused with digitization and digitalization efforts, which are other terms you’ll want clear definitions for as well!)
To start your transformation journey—or reconnect with your purpose when you feel lost in the current one—it helps to be more specific about what kind of transformation you are talking about. What are the things you want to work differently in your organization? Is it necessary to change on all levels in parallel? Do what product folks would do and embark on a bit of a problem space discovery. 🙂
Find common ground
Now assuming that you have various transformation efforts going on, how do you find the things worth focusing on? What should you work on first? Where is your biggest lever?
While each transformation has its distinct focus, you're likely to encounter overlapping areas that you can use as opportunities to create even more improvements.Identifying these intersections—such as a universally problematic meeting culture—can provide a strategic starting point for broader transformational efforts. Addressing these shared issues not only lays a foundation for further specific transformations, but also creates immediate, tangible benefits across the board.
In a workshop with some of my clients, I created a diagram to illustrate the various themes they might want to tackle via transformation. These included: improved meeting culture, better goals, clearer competencies, more focus/easier prioritization, and improved cross-department collaboration.
You can see how most themes are interdependent—that's why the diagram on the bottom has so many arrows pointing between the themes. However, one theme, "improved meeting culture," doesn't have any arrows pointing to it, which means it's relatively independent of the other themes. That's why we decided to focus on this theme first.
This diagram illustrates how one team chose to focus on "improved meeting culture" because it was the easiest theme to tackle independently.
Emphasize action with a principle like 'outcomes over output'
For example, let’s consider a principle that can drive transformation across various fronts: "outcomes over output." This mindset shift focuses on achieving meaningful results for users and the business, rather than merely ticking off output quotas.
To be more specific, it involves talking about and measuring the “change in customer behavior that helps drive business results” instead of discussing the product features you’ve released and use cases you’ve supported. It's about ensuring that every effort contributes to the strategic goals of the organization, balancing user needs with business objectives. (See Outcomes over Outputs by Joshua Seiden to explore this concept in more detail.)
Implementing the principle
To embed this principle within your organization, start with tangible, focused actions. For our little outcomes over output example, let’s say that you know roadmaps are a problem in your organization. Different teams use different formats and cadences, which means no one really trusts these documents and they create more confusion than clarity. In that case, you would:
Gather current roadmaps: Collect existing product roadmaps, regardless of their format or detail. This initial step fosters a collective understanding of the current state and underscores the importance of strategic planning.
Standardize roadmap duration: Align the roadmaps to a consistent time frame, such as six months, to ensure comparability and coherence.
Conduct outcome-oriented workshops: Facilitate workshops for different stakeholders—product teams, executives, and line managers—to cultivate a shared understanding of what 'outcomes' mean and how they can be integrated into roadmaps.
Iterate and improve: Regularly review the roadmaps, encourage cross-team learning, and continuously refine the approach to ensure it remains aligned with the overarching goal of driving meaningful outcomes. This step is important, so don’t skip it—we rarely get things right on the first try, so it’s important to create the expectation that iteration is simply part of the process.
I used the outcomes over output principle as just one example to show how you can break down transformation efforts to make them more actionable for everybody. You can choose anything you’d like—the key is to focus on an actual change, focus on doing one thing differently, and focus on the action.
Help folks establish rhythms and rituals
One “low-hanging transformation fruit” (excuse my biz bullsh*t lingo here ;-)) is helping the organization to establish valuable rituals and making sure there is a rhythm to them.
Let me explain: If you’ve ever worked in a high-performing team or organization, I bet there has been something like a heartbeat to certain activities.
Let’s take a well-oiled scrum team. They have their iteration heartbeat, their two-week sprints. And they have the same rituals each iteration. Sprint planning, daily standups, a review meeting, and a retrospective to close the iteration. (By the way, if this all sounds like a new language to you, check out this video for a good overview of agile product ownership and an introduction to all these concepts.)
Living in such a structure and doing the rituals repeatedly can be very liberating. Everybody in the organization knows that the team does a demo of the working software they’ve created every other week (AKA the “review meeting”), so there is no need to constantly ask for what they are working on since folks could just attend these sessions to get their update. And if every two weeks isn't enough, they are very welcome to attend a daily standup to ask questions.
I hope you are getting the idea: creating meaningful rituals, doing them on a certain rhythm, and improving them over time makes a huge difference in organizations and is what I would consistently recommend for everyone. That applies to annual strategy reviews, quarterly goal-setting sessions, your quarterly idea-to-opportunity assessment, etc. Try to eliminate as many one-off meetings as possible and replace them with meaningful rituals.
Wondering what to do to get started? Map the meetings you find in everyone's calendar to the following list of meeting purposes to identify white spots.
Directional clarity: Vision, strategy, and goal setting
Opportunity assessment: Finding meaningful problems to solve
Product discovery
Product delivery
Product optimization (can be handled as part of discovery, but for some companies it’s easier to tackle it separately)
Then check if there is a meeting for starting/creating things, for sharing stuff with the org, for talking about progress and obstacles, one for presenting results, and one to reflect on the process itself and on how to improve it. And then finally give it some cadence and rhythm in everyone’s calendar. For example, directional clarity meetings likely only need to happen on an annual basis (or when something major changes), while product discovery and delivery meetings happen on a weekly or biweekly cadence.
Another tactic to try: The transformation backlog
Approaching transformation as an ongoing process rather than a destination is crucial. But how do you keep track of the many things one could work on?
I bet you are familiar with the concept of a backlog and task boards (your teams likely use a tool like Trello, JIRA, Asana, airfocus, or something similar to keep track of ideas they’d like to pursue in the future as well as the work that’s currently in flight).
Why not use this tactic in your transformation context as well? Developing a transformation backlog allows you to prioritize initiatives, ensuring a focused and manageable progression. This strategic approach prevents overload and resistance, fostering a culture of continuous improvement and adaptability.
If you create a task board visualizing work in progress and being transparent about obstacles, blockers, and overall progress, you’ll be doing a great job of leading by example.
Here's an example of a transformation backlog and task board. Feel free to use this as a template for your own work. You can customize any of the column names to your specific needs. Just keep in mind that they should help you track various stages from problem identification through to assessing final impact.
This example backlog and task board gives you an idea of how you can track your transformation ideas and projects to ensure transparency and accountability.
Conclusion: Don’t aim for change, but for evolution and improvement. We want things to actually get better.
Wait—in an article that’s all about transformation, why am I now saying “don’t aim for change”? There’s a subtle but significant distinction here. We’re not just changing for the sake of changing—we’re changing in order to make things better. Marty Cagan refers to the concept of “transformation theater,” when companies and teams focus on transformation activity rather than transformation results.
My hope is that by going through the steps I’ve outlined—clarifying what type of transformation you’re aiming for and finding common ground, you can find comprehensive and consistent ways to apply these concepts across your organization, which can catalyze broader transformations. Remember, the goal is not just to change but to evolve purposefully and continuously, building a resilient and innovative organization that’s poised for the future.