AWS Cloud Enterprise Strategy Blog

The Living Transformation: Pragmatically approaching changes

experimentation main

Transformation is not a destination; it’s a journey of continuous growth and self-discovery.

—Tony Robbins

I used to run regularly until life got in the way. I now intend to spend a boatload of money on fitness gear and fit running around all my other activities, probably starting in the new year. I anticipate being ready for the Paris 2024 Olympics.

I know – ridiculous – yet it’s similar to how many organisations approach their transformations. The word “transformation” is habitually appended to terms like “cloud,” “digital,” “data,” and “generative AI.” A big vision is set; vast quantities of money ringfenced for consultants; and vague, aspirational goals dumped onto already busy teams. Predictably, these transformations disappoint unstated expectations and rarely meet the intended outcomes.

Many outdated management principles permeate organisations from nineteenth- and twentieth-century management thinkers (spans of control anyone?), but the one commonly ignored is that transformations should be continuous – something Mark Schwartz alludes to in his blog post. The thinking is simple: Organisations can improve daily rather than embrace a status quo broken by episodic, disruptive transformations. At the heart of this belief is an understanding that linear transformation plans ignore organisational realities.

Organisations Are Complex Systems

The organisational theorist Russell Ackoff describes organisations as complex, ambiguous “messes” to be managed, not logical constructs that can be tweaked to achieve a desired outcome – an off-putting but accurate description.

Systems thinking teaches us that four elements must be considered when attempting to improve a complex system: (a) the desired outcome; (b) individual system components such as teams; (c) the interactions between these components; and (d) the feedback mechanisms that reinforce, over-amplify, or dilute impact. Permeating these elements are hidden assumptions and interactions, unstated ways of working, unintended consequences from changes, and invisible dependencies and power dynamics that typically reveal themselves at inopportune times. Despite this, we tend to gravitate to the individual components, redrawing org charts and ignoring the wider challenges.

It’s one of the reasons that seemingly simple decisions such as revamping the infrastructure team to be more cloud-centric, creating cross-functional teams with a single leader, or outsourcing elements of technology provoke unintended consequences. These are normally centred on perfectly natural human responses to change. Some will perceive a loss of power, others a gain. Old mindsets on how work should be done will grate against new thinking.

These consequences rarely show up immediately. Delayed consequences of a change have a habit of popping up at the worst time to derail progress. These unpredicted side effects are one reason that making changes to organisations is more akin to untangling a hairball than moving boxes around on an org chart. It is one reason big-bang transformations rarely succeed, as they have to predict most of these consequences to succeed.

So how can you reframe the challenge?

Start with Clarity

Acknowledging this complexity drives a simple, critical need for organisations to become better versions of themselves: clarity. As Alice in Wonderland’s Cheshire Cat observed, “If you don’t know where you are going, any path will get you there.”

Clarity means cocreating a story of what “great” looks like with your organisation. It contextualises what “faster” or “better” means for everyone.

This clarity is not a five-year plan describing an unmeasurable future full of vague promises based on arbitrary “strategic pillars”—if only the competition and world didn’t change during this time! Nor should it be underpinned by exhortations to be more agile, cloud-like, data-centric, innovative, or whatever other words appear on the latest corporate buzzword bingo card. None of these define meaningful outcomes or help individuals determine what to do to contribute.

The story should define a meaningful, better future that capitalises on your team’s shared view of its competitive strengths and customer needs. Use tools such as Wardley maps to debate and create a common definition of competitive advantage [1]. Don’t prematurely introduce constraints or justify why this future state is not attainable.


Once a shared story has been defined, it is surprisingly common to see an absolute, basic need fall by the wayside: communication. This is where the magic happens, continually signalling through storytelling, recognition, and other tactics that you are unified by a shared vision and goals. It helps to overcome our fight-or-flight response and satisfy our need to belong. Such a foundational element helps to overcome old mental models that once served us well but no longer do. It is a continuous reminder to staff, new and old, why this new future is good for them and their organisation.

Transforming Is Crazy Golf, Not a Race

Back to my running analogy. Transformations often get described as “a marathon, not a sprint”—noble but misplaced. Races have well-defined paths, an end state of victory or loss, and short-term exertion.

At AWS, we talk about being stubborn about vision but flexible on details. The story of a better organisation becomes the stubborn vision. It changes little if cemented on principles such as experimenting with customers and rapidly creating minimum loveable products to test concepts. After all, there will always be a better, faster, more cost-effective way to experiment with more and better ways of emotionally engaging customers.

The “how” of improving in these areas is not a linear progression based on a project plan. A more practical approach is akin to the technology hackathons many of us have run or participated in—many time-bounded, focused experiments and prototypes to test hypotheses and garner support for an idea. The same works with culture. Culture hacks have several benefits. They are small enough to be tested with little risk and can yield quick results as well as insights into hidden assumptions and unexpected feedback loops. Everyone can participate. The cost of changes will typically be low, and many experiments can be run in parallel. Hacks also fit better with humans’ ability to cognitively process and accept changes.

Good hacks can be conceived and tested in a relatively short period. You can tap into your entire workforce. As I’ve written previously, those doing the work are best positioned to surface and test ideas. These hacks need to be transparent. Successful hacks should ripple through an organisation, inspiring others to try them. Unsuccessful ones should provide learnings that are lauded and propagated, informing the next step of hacks.

One simple approach I’ve used to start this process is creating a card pack. Each card lays down a challenge: make a decision simpler or faster, eliminate or shorten a process, or automate a manual activity. Pick one a week or month and have someone on the team identify and own the time-boxed application of the hack with the best of the team’s support.

Make Changes Sustainable

Sometimes large, one-time changes are required in the case of a turnaround. But I believe the evidence shows that transformation is not a one-time act of trying to rewire an organisation but rather a choice to make it a whole team sport. The former may feel faster, haring off into the distance with profound leadership commitments, but the ability to persistently and consistently embed changes into an organisation’s core is far more valuable and sustainable.

An initiative-based transformation is easy to undo; the initiative can be scrapped. A culture-based transformation is harder to implement and equally harder to undo due to capricious leadership decisions.

Play the Leadership Long Game

A CIO, CTO, or CMO is not a leader just because of their title. Titles are arbitrary indicators of hierarchy, accountability, and salary. True leaders look beyond their and their direct team’s goals and actively model breaking down siloed behaviour to ensure the entire organisation marches towards the same future.

If, like me, you believe that transformations are lifestyle choices rather than one-and-done initiatives, you likely accept that they cannot be tied solely to a leader’s tenure. Great leaders think and act beyond their tenure, laying the people, cultural, and technological foundations that might not immediately pay off but provide a base for their organisation to grow. We should judge leaders in part after they leave based on this legacy.

This applies at every level of the organisation. If you are an infrastructure or application leader in the cloud centre of excellence that Mark described in his blog post, your primary goals are to bring your expertise and leadership to achieve business outcomes enabled by the cloud, not to defend your turf. It sounds highfalutin, but good leaders put aside their egos.

I’d urge you to apply these patterns and declare a journey of continuous evolution, not big-bang revolutions. Think of the majority of future transformation projects as a reaction to failure to change previously—even a failure of leadership perhaps—rather than a bold leadership initiative.

I truly believe that organisations and leaders that embrace the complexity of their organisations successfully change dated mindsets and ways of working. This has been true every century. The technology we have available through the cloud is just waiting for our organisations and leaders to catch up.


1 Poccia, Danilo. “How to Connect Business and Technology to Embrace Strategic Thinking (Book Review).” AWS News Blog, February 14, 2023.

Phil Le-Brun

Phil Le-Brun

Phil Le-Brun is an Enterprise Strategist and Evangelist at Amazon Web Services (AWS). In this role, Phil works with enterprise executives to share experiences and strategies for how the cloud can help them increase speed and agility while devoting more of their resources to their customers. Prior to joining AWS, Phil held multiple senior technology leadership roles at McDonald’s Corporation. Phil has a BEng in Electronic and Electrical Engineering, a Masters in Business Administration, and an MSc in Systems Thinking in Practice.