24th October 2017

The digital leaders’ guide to high stakes digital transformation – Part 2

Andrew Larking
Creative Director

A roadmap for change.

This is the second in Deeson’s three part guide for business leaders on executing a successful digital transformation project. In producing this series, we’ve drawn on our extensive experience of helping ambitious clients deliver high stakes organisational change. 

Our first post focussed on the reasons for and approaches to change.

But whatever the driver, be it fresh competition or new technologies to a change in consumer demands, going from “we must” to “we are” is a huge step. 

In this post we discuss what happens once you’ve made the decision to start a transformation initiative, and the key tasks you need to have at the top of your to-do list.

Workshop in action

The first tangible outcomes.

So you have agreed your company’s vision, the high-level strategies you’ll use to deliver it, and the reasons why you are looking to transform – what happens next? 

We’ve found that there are five jobs to do in order to get you moving:

1. Take stock.

You can do nothing without data, and you must never fall into the trap of believing your own first assumptions. To find out how digitally healthy your organisation really is you need to ask everyone who works there and, if you can, a good number of your customers.

Ask them to spend 10 minutes filling out a digital health check – a short survey designed to yield a large amount of data on how digital is seen and used by various teams, and how the organisation as a whole values digital thinking. 


"Your digital health is how prepared your organisation is for the changes that digital technologies have already bought about, and will continue to introduce."



The survey will give you insights into how you, as a collection of people, invest in technology and training. It will show you how many people work “in digital” and who they report to. It will reveal the relationships between departments, how digital services are funded and maintained, decision processes, and successes and failures.

Crucially, it will show you how far ahead you are thinking.

Depending upon the size of your organisation this exercise can take a long time, and analysis can be hard.

Our work for the Imperial War Museum involved speaking to over 200 members of staff across 5 locations, and from those interviews and workshops we identified patterns and insights that had previously been missed. These insights gave us the beginnings of a hypothesis, or prototype, to test later.

You should allow yourselves twice as much time as you think you’ll need. Set up a war room, cover the walls, and allow yourselves time to sit and stare. Get away from the computer screen, write out everything long hand, and order plenty of sticky notes!

Wall covered in sticky notes

2. Think big.

Using your organisational vision and the outputs from the digital health check, the next stage is to devise an idealistic concept for how digital will help your organisation address the internal and external drivers for digital transformation you identified in the earlier stages of the project.

It sometimes helps to use a smaller project as a catalyst for digital transformation. A new CRM, website, or brand identity are some examples of projects that can be used to drive larger change.

I know, big organisational change thinking on a small project? The purpose here is to test the methods you will use to make change happen, and use this project as the excuse and opportunity to uncover the larger issues you need to address.

This smaller project will help your teams focus on a specific goal, and train them to think about how a project fits into a larger set of pieces to drive company-wide change.

Don’t let your vision for digital be reduced to what is possible with current technologies, current teams, or current processes. Everything is up for change at this point. Use the needs of your customers, employees, and of course your organisation as your point of reference.

3. Build advocacy.

Create a low fidelity ‘prototype’ of your concept and use it to demonstrate your vision to everyone in your organisation – either face to face, via a recorded talk, web conference etc.

Be creative. Your prototype should not be a working technological solution, but an idea or concept. It could be series of sketches, a presentation, or whatever it takes to demonstrate your vision to your colleagues. 

Digital transformation is about spreading digital capability and thinking throughout your teams, so start building the excitement and advocacy now. Creating a prototype is a fantastically liberating tool for teams who’ve never worked iteratively before, and it makes demonstrating your thinking much simpler. “Show, don’t tell” is the mantra here.

For the University of Derby, who are currently undergoing a complete digital and brand transformation, we wrote and delivered an “Art of the Possible” lecture designed to show what is now possible and expected from digital technologies. The “prototype” showcased was a big vision for the future, backed with what the user research had already found. It built advocacy for the project, and was a fast and cost effective way to get 500 people involved in the project.

4. Gap analysis.

To act on your vision you need people who are capable, technologies that are fit for purpose, and attitudes which will foster innovation. You need to perform an initial gap analysis.

Your vision is linked to strategic goals, you’re starting to get people’s buy-in, you now need to understand the difference between where you are now and where you want to get to.

If your new vision requires a heavyweight set of integrations between CRM, CMS, ticketing, and data infrastructures, you need to know if the teams responsible are large enough, skilled enough, have the right tools and processes, and full support of management. 

If integration with social channels is key to driving new audience sectors, do you have members of those audiences working for you, with full and final control over your new social channels?

Your first gap analysis will miss out a lot of detail, but it is an iterative process. Break your vision down into the tactical things that you need to do, work out if you can do them, and if you can’t you have a new task to add to your roadmap.

5. Define your initial roadmap.

The part that everyone is scared of – the roadmap – can be defined broadly in a day.

If you have completed the first four tasks it will already be obvious what you need to do and the order it needs to be done in. What won’t be obvious is how, but your teams will solve that.

Don’t let yourselves get bogged down in detail too early. You will almost always find yourself needing more information about a specific team or technology, which is where you return to the gap analysis phase and look deeper.

Come back to a further roadmap session, and then carry on repeating this back and forth between identifying the gaps and putting in place a modified roadmap to fill them. Your map will never be complete, and neither will your transformation, but the processes of iterative change will become increasingly comfortable to everyone in your organisation the more you do it. 

As you begin to define department-specific tasks, you’ll want to introduce this way of working to the department. Then, when they are comfortable, you should leave them to it. The digital transformation lead role is to define the direction of travel for the business, and to communicate that clearly to everyone. It is everyone else’s job to make it happen.

Digital transformation is often described as a marathon rather than a sprint. In most cases it’s an ongoing process. You need everyone involved to drive this change – it’s not a one person job. Be a leader, and stay away from the small stuff.

What else?

The steps outlined above are a summary of a much larger set of tools that we use when helping our clients transform their business. Alongside the vision, prototypes, advocacy building, gap analysis and roadmap we suggest: 

  • Understanding the changing needs of your customers with journey maps.
  • Undertaking analysis of your competitors.
  • Performing SWOT (strengths, weaknesses, opportunities, threats) analysis workshop(s).
  • Putting in place clear digital leadership and, if needed, creating a digital transformation team.
  • Designing, testing, and documenting any new business processes.

In the next post we will discuss how to win hearts and minds across every level of your organisation, how to create digitally confident and capable teams, and how to ensure that your teams understand their part in the wider digital transformation.

Like this post? We're running a series of breakfast briefings on the five steps to successful high stakes digital transformation. Email events@deeson.co.uk to request an invite.