Digital Transformation: Set up for Success

You’ve all seen the numbers. Research from leading consulting and research firms like BCG and Everest Group suggests 70% of digital transformations fail to generate significant value and fall short of their objectives. With billions of dollars poured into digital transformation initiatives each year, what can organisations do differently to end up on the right end of transformation journeys? 

I’ve put together this article to help brands and organisations grasp the fundamentals for applying transformation & change principles in a programme environment. Some context first:

Transformation vs. Change

In simplest terms:

Transformation denotes a future state, an organisation’s aspiration towards serving their customers by unlocking hidden value through strategic innovation. 

Change Management, however, comprises the techniques, tools, applicable frameworks, and lessons learnt from previous undertakings

While transformation addresses the ‘what’, change management deals with the ‘how’ and help transformation teams with identifying the navigable paths throughout the journey.

Setting the Vision: The bolder, the better

A clear vision needs to be set as the northern star along with guiding principles as part of the broader constellation. Avoid this at the risk of delivering partial benefits with no significant value for your customers.

Start with asking the following questions:

1. What do we aspire to become? Be Bold!

Good example: Provide best-in-class, hassle-free, mobile-first e-commerce experience for our most loyal customers.

Poor example: Increase mobile e-commerce sales by 30% across top 3 categories

2. What does success look like? Quantify!

Good example: Increase current CSS (Customer Satisfaction Score) by 30% with attributable total average cart value increase by 15% for returning customers.

Poor example: Retain existing customer base and improve new customer acquisition. 

3. What are our guiding principles? Be obsessed with creating added value for your customers!

Good examples here only: 

  • Customer-orientation: When in conflict, favour customer / front-office designs & design requirements over those of back-office functions.
  • Mobile-first approach: UX at the forefront. Three clicks to allow completion of high-value queries or transactions.
  • Good design should reduce friction, not add additional overhead: Consider implementation of conversational commerce features & real-time on-screen support. Move away from outdated ticket designs and SLAs.

How to Successfully Govern Digital Change

1. Programme Structure:

The size and complexity of each programmatic undertaking require a tailored approach, hence fit-for-purpose governance. Agreeing on whether a single or multi-stream structure will be needed is foundational to building momentum and supporting delivery. If you don’t know where to start, start with hiring a Programme Manager.

2. Stakeholder Mapping vs Context Mapping:

The textbook definition of stakeholder mapping mandates mapping sponsors, programme resources and users. On the other hand, a context mapping further extends this visual representation to add cohesiveness by providing insight into each stakeholder’s understanding and perception of the programme’s deliverables, success criteria, and the circumstances surrounding the business.

3. Identification of Project Change Streams & Roles:

Open too many fronts, you will most certainly fail. Fail to recognise the need for dedicated change streams, and you’ll risk landing a top-down heavy programme structure slow on the delivery end.

Structure aside, a transformation programme under a programme manager will usually justify the presence of Subject Matter Experts and various other roles in addition to core PM and PMO support functions. The most common roles are:

  • Programme Manager: The orchestrator and generalist who coordinates milestone deliverables, oversees budgets, manages stakeholder relationships, and tracks benefits.
  • Finance & Procurement Leads: They manage the day-to-day regarding actual vs projected spend, report on costs vs benefits, and play a key role in supplier/vendor negotiations.
  • Project Manager: The stars in charge of change delivery with oversight on technical and functional delivery. PMs are the ultimate change agents for their streams/functions.
  • Functional and Technical Leads: The creators, makers, and enablers of change. Highly specialised folks and rarely shared resources. FL/TLs are responsible for translating the organisation’s requirements into future state products and functionalities.
  • Change Manager and Analysts: A Programme Manager’s top aides. T-shaped change agents who can step in as needed to accelerate programme or stream-specific deliverables. Their duties range from building business cases to conducting business readiness analyses and implementing change comms plans.

4. Reporting & Transparency:

Assuming the programme consists of the resources stated above, focus on:

  1. Spend is under control and an authority matrix is in place
  2. Definition of milestone activities and deadlines are visible at the programme level and broken down by streams
  3. PMO principles are followedirrespective of the methodology, be it Waterfall or Agile.
  4. And common consensus has been reached in terms of what qualifies as milestone activities vs. key activities.

5. Benefit Tracking:

ROI, the holy grail of every programme. No programme/project stream kicks off without sign-off from the sponsors or stream leads. And no initiation document gets in front of the sponsor without referencing the expected benefits with clear timelines and quantifiable goals. Once identified, proactively track and report benefits as well as potential shortcomings to review baselines, if necessary.

Mobilisation: Setting Sail

Mobilisation of a programme consists of a more complex set of activities in comparison to the initiation stage of a project. While each stream will still need sign-off and authorisation to proceed with their respective projects, the programme sponsor and the executive will likely seek the following at the consolidated programme level before authorising the start of the programme activities:

  • Plans Theme > to monitor baselines & interdependencies.
  • Change Theme > to address changes & react to “unknowns.”
  • Business & Technology Readiness Templates > to ensure blockers are removed in a timely manner.

From this point on, the execution skills of the sponsor and the programme leadership are put to test. Humble beginnings such as the first PO or a discovery workshop usually signal the start of the journey.

If you’re lucky enough to deliver on your day one activities, celebrate! Seminal moments such as these shouldn’t be overlooked… Make a habit of celebrating small wins as much as big ones.  

Delivery: The Moment of Truth

Delivery is king, and perception is reality. Not everything will go to plan, and managing stakeholders’ expectations can become tricky business when progress reports lack enough Greens to maintain credibility and trust. In extreme cases, Red status domination can derail a programme entirely. Here’s what can be done proactively to avoid unpleasant outcomes.


Leave no room for ambiguity and support early stages with a sign-off process. The majority of the design requirements are identified at the early stages of a project. The more engaged products owners and senior users are at the beginning, the higher chances for bashing through the many delivery stages that will follow. Pay extra attention to the timely completion of design and discovery phases. 

Early Identification of Stars vs Laggers:

You’ll be able to spot members of the two camps almost immediately after mobilisation. Once a Red, almost always a Red. It’s not unheard of for a programme manager to roll up the sleeves and adopt a more hands-on approach to accelerate specific streams’ deliverables.

To maintain programme-level focus while helping a particular stream with their battle, apply situational leadership:

  • Delegate more to star teams to make time for laggers
  • Adopt a directing style with laggers to accelerate delivery.

The idea here is to prevent chronic Reds from forming, but this shouldn’t come at the expense of sacrificing other Greens, so there is a limit to how much hands-on support a stream should get. Escalation should be perceived as a standard route, and both the Change and Risk themes should have been tailored upfront to tackle such challenges.

Stakeholder Perception & Change Communication:

There’s Green and then Greener. No matter how good a job you do in delivering results and communicating success, know that you can never do enough comms to get to everybody. So, whatever you have planned in terms of comms, multiply these efforts by at least three and be creative in opening new channels to amplify the message.

Maintain Budget Discipline

The ideal scenario: on time & budget. That said, most programmes operate with buffers and contingency funds, and consistent on-time delivery will likely be rewarded over everything else even when budgets need to be flexed. 

Remember delivery is king until dethroned by cost. Keep your focus on delivery, and don’t let the latter find an opening. 


Each transformation programme is determined by the context, the circumstances surrounding an organisation and the sense of change-urgency. 

While no simple answer exists as to which transformation governance structure could work better in a digital change climate, the points highlighted herein transcend this issue and aim to provide the readers with a humble set of practical and universally applicable principles.