Creating a roadmap that sets your digital transformation up for success

A strategic roadmap is a vital artefact for any digital transformation, says Antonio Weiss. It speaks to multiple audiences and serves multiple important purposes

Becoming ‘digital’ doesn’t happen by magic. To give yourself the best chance of success you need a carefully considered, well-articulated plan for how you get from where you are now to where you want to be. This is your digital roadmap.

Somewhat paradoxically, while you need to aim to stick faithfully to your roadmap, you should also be very alive to the possibility that you may need to tweak it, amend it, or rip it up and start again. This is at the heart of good agile working. But it’s also the essence of digitisation. The changes you are planning may be so novel, or the technologies you are adopting so rapidly developing, that the future is bathed in uncertainty.

So, develop your roadmap with thought and care. Treat it as the glue between your vision, your strategic delivery vehicle, and your desired end goal. Use the roadmap – which is likely to take the form of a written and, ideally, visually compelling document – to communicate to your seniors, your stakeholders, and your colleagues.

Celebrate your progress as you go. But it’s always ok to change if circumstances require it. Just make sure to develop a new roadmap when you do.

Addressing the problem at hand

A roadmap is a vital artefact for any digital transformation. It speaks to multiple audiences: senior stakeholders, team members, and even customers. And it serves multiple important purposes.

  • Aligning your vision with your strategic delivery vehicle: the roadmap helps make real the ‘what’ which you’re aiming to achieve with the ‘how’ for which you’re planning on doing it. It is your plan, and if the plan doesn’t match the vision, it won’t work.
  • Communicating what you’re doing: it is essential that you are transparent with your organisation as to what the digital transformation entails. The roadmap should have multiple layers of detail, but at the highest level, it should be able to quickly inform a senior audience exactly what to expect, and by when.
  • Avoiding doing everything at once: failure to prioritise will simply lead to failure. Roadmaps force you to set what you will do first and then the sequence of what comes next. A roadmap should also help you understand what could be dropped altogether. If a workstream or initiative doesn’t clearly help you achieve your vision, then don’t do it.
  • Working out the interdependencies: any change involves workstreams which are interdependent. And this is particularly true in the world of technology. You may be planning on implementing an analytics service – but does the analytics solution need to integrate with your main enterprise platform? It most probably does, and so you should put determining the platform first in your roadmap and only then deciding on the analytics solution. By understanding the interdependencies (and also what is therefore independent – not connected to other decisions) you’ll be able to narrow down options and be clearer about the phasing of key decisions.
  • Setting checkpoints to track progress: a good roadmap should set out outcomes and deliverables to be achieved within a given timeframe. As you progress through the lifespan of your roadmap you can check in on progress.
  • Allowing opportunities to pivot: and of course, if you are well off track from your plan, your roadmap should present opportunities where you can change course before it’s too late.

Making your roadmap real

So this is when your digital strategy starts to become real. Your roadmap should be the next phase from your overall strategy; you already should know your corporate and digital objectives. Now we want to outline the specific steps that will help to form the roadmap. The roadmap should give you a clear plan for a defined time period, with detail that describes the workstreams, objectives, outcomes and individuals delivering the roadmap components. The following steps will guide you.

1Start with the strategic vision and timeframes.

A roadmap should ideally be no more than five years, and usually a sub-three year horizon is optimal. This reduces uncertainty and avoids creating too many ‘potential’ different paths to take. If your organisational strategy, as many organisations do, is looking at something more akin to a ten-year timeframe, consider dividing the time into ‘horizons’ of three year chunks. This should stop you from making wild assumptions by presupposing that you can know the future.

Let’s consider a worked example here. During the Covid-19 pandemic, many restaurants had to rapidly pivot towards becoming digital restaurants – offering home deliveries, bookings, remote payments, and more. In this scenario, a digital vision could have been something about ‘enabling a first-class dining experience underpinned by digital technology from the comfort of our customer’s home or our safe and Covid-secure restaurants, within three months.’

2Establish the user needs

The importance of using actual users – customers, staff, stakeholders, shareholders – to guide your strategy cannot be overstated. You should set out who your key users are, and then what the ‘needs’ – the things that they want to achieve or obtain through using your service – of these users are. This should be future-facing, so you may include ‘needs’ that are not currently served by your current state, but which you are aiming to achieve.

In our restaurant example you might have:

  • As a current customer, I want to be able to order, pay for, track delivery of and give feedback on my food order, so that I can enjoy my order at home
  • As a potential customer, I need to know what the restaurant offers so that I can consider whether to place an order
  • As a staff member, I need to know what the orders are so that I can fulfil them
  • As a restaurant administrator, I need to know what was ordered, when, and that it was paid for, so that I can process accounts and payments

There may be more needs – for instance, customers may wish to make a booking for the restaurant or administrators may wish to understand business performance through analytics – but these give an idea of some key user needs.

3Develop the workstreams

By understanding user needs you can begin to shape workstreams that meet these needs. In the above example, you may determine you have four broad workstreams:

  • Serving current customers
  • Winning new customers
  • Digitising internal operations
  • Reporting and analytics

These should roughly match, respectively, the order of the user needs described above. Whilst you should not be jumping to a solution yet – that comes next – your organisation’s resources for transformation should set parameters for what’s possible. For example, going back to our restaurant case study, let’s assume that the restaurant has decided it is best to rely on external suppliers to deliver its digital transformation, owing to the digital immaturity of the organisation and the fact that technology is not one of its core competencies. This should help narrow the options available quite materially: with these organisational archetypes in mind the restaurant would be wise to choose a single software platform to fulfil as many of its user needs as possible.

4Cluster the interdependencies

In some instances, one technology choice will close down options for future choices. Shopify, one of the biggest ecommerce platforms, has a large range of API-enabled connections to a suite of applications for everything from mailing list management to analytics. But it doesn’t cover everything. With this in mind, if you choose Shopify over another ecommerce platform such as Stripe, your options will be restricted by your original platform choice: these are interdependencies. In your roadmap, try and disentangle where you have interdependencies. Again, in our restaurant example, it’s likely that the ‘Reporting and analytics’ workstream will be dependent on the software decisions made for ‘Serving current customers’. Here it would consequently be important to make the decision for this latter workstream first.

5Identify the fixed points

Are there any critical changes or issues in your timeframe that you need to factor into your plans? In Europe, changes to data security requirements such as the 2018 General Data Protection Regulation (GDPR) Act ensured all companies processing customer data had to factor in GDPR compliance into their roadmaps. Other common issues that create fixed points are cloud hosting decisions or replatforming. On the former, for example, certain hosting domains – of which Microsoft Azure or Amazon Web Services are the most common – may have an impact on your software choices. A number of analytics tools are better suited to one cloud environment than another, for instance. Consequently, if there are organisational plans to move to a given cloud hosting platform at a specific date, factor this into the roadmap – if may cause you to delay certain workstreams.

6Cost up and prioritise

Even at this early stage, you should be looking to have a broad sense of how much certain workstreams will cost. Ascertaining costs should be guided by the decisions you’ve made regarding your resourcing approaches. If you’re going for a single supplier approach, some early pre-procurement conversations with potential suppliers, or speaking to similar organisations using the suppliers you’re considering should give you an early idea of costs. If you’re planning on developing your own digital services, you should have a broad sense of development costs and be able to factor in rough timings. Make sure to include any costs related to organisational changes.

Once you’ve set out the likely costs, you may need to prioritise workstreams or even hold some back. In our restaurant example, whilst you may strongly wish to onboard new potential customers with a social media drive, the costs of a large digital campaign may cause you to delay this until the most pressing changes are up and running.

7Set out the roadmap and governance

Once you have your workstreams prioritised, you should be in a position to write out the roadmap and develop its phasing. For each step in roadmap, consider:

  • What are you trying to do? E.g., develop a digital customer buying, tracking and feedback experience
  • When does it need to be done by? E.g., end of quarter 1
  • Who is doing it? E.g., Digital Innovation Team, supported by seconded restaurant staff input
  • What are the key outcome measures? E.g., 95%+ client satisfaction in process

You may consider that some parts of the roadmap should be piloted first. If so, make this clear, and then specify what are the success criteria for the pilot and what happens if it’s successful or unsuccessful.

The roadmap will need supporting governance. You need to be clear on responsibilities and accountabilities, and set out a steering group or project board to review progress and delivery against the roadmap, and ensure you have a feedback route up to senior stakeholders if challenges are encountered.

8Communicate, communicate, communicate

And finally, do not hide the roadmap anyway. This should be a living, breathing and iterated document. It should become well known across your organisation. Seek feedback on it early on. And then celebrate successes as you progress. This will help to build confidence in your ability to deliver and win trust through transparency and openness. The roadmap doesn’t just need to be an internal document. Unless there are competitive reasons not to, think about sharing it publicly with customers – they may be keen and excited to know what future improvements they can expect from your organisation.


This article is based on an excerpt from The Practical Guide to Digital Transformation (Kogan Page), exclusively developed for AMBITION.

Dr Antonio Weiss is a Senior Partner at The PSC, an award-winning public service consultancy specialising in user-centred design, digital, strategy and delivery. He has advised the Office for Artificial Intelligence, the UK Space Agency and NHSx as well as numerous other pioneering digital organisations. He is the author of The Practical Guide to Digital Transformation, and three other award-winning books.

Dr Antonio Weiss is a Senior Partner at The PSC, an award-winning public service consultancy specialising in user-centred design, digital, strategy and delivery. He has advised the Office for Artificial Intelligence, the UK Space Agency and NHSx as well as numerous other pioneering digital organisations. He is the author of The Practical Guide to Digital Transformation, and three other award-winning books.

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