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Digital Transformation Playbook for CEOs

Updated: May 25, 2022

Defining your digital strategy is not as simple as buying a product or service, despite what vendors might tell you! Your digital strategy should be developed after a detailed analysis of your organisation, its business strategy, and what combination of business process and digital tools will help make your business strategy a reality.

Selecting digital transformation

The whole thing can be a little confusing of course - in fact, even the term “digital” means different things to different people! So, we’ve put together a quick playbook to help CEOs and business owners navigate this complexity.

There are five main points to consider:

1. Define digital: get clear on what we're talking about

2. Understand what you’re getting into

3. Stay open to fresh, new ideas

4. Make sure your people are on board (this is crucial and often forgotten!)

5. Be ready for the next challenge

Define digital

Context is everything. Think about it: depending on the situation, “IT” can be a pronoun, an acronym or even a creature from another dimension disguised as a clown.

For many business leaders, engaging in an “IT project” has about as much appeal as a meeting with Pennywise. For decades, “IT people” have had a habit of using confusing language shot through with (often meaningless) acronyms and brutal sales tactics such as "fear, uncertainty and doubt” (or FUD, to apply the obligatory acronym).

In recent years, the term “digital” has been used as a shortcut for “digital marketing”. This is of course an important aspect of any digital strategy, but it is not the whole story. Your advertising agency can’t help you with the rest, and the rest may be where all the pain (and therefore gain) is to be found.

When we’re helping organisations define their strategy, we use a “four-quadrant” model to understand the nature of your digital challenges and where the focus should be. You can try it out for free if you like.

Understand what you’re getting into

I have often heard leaders say something like “If only I’d known what would be involved, I never would have started this”. Even in successful projects, there can be a gap between what the customer expected and what they ended up getting. Imagine if that happened when you bought a car:

Salesperson: “Certainly sir, this car will do 1,000 kilometres per litre of petrol”.

Customer: “Really? That’s fantastic!”

Engineer: “Well... it’s less than that, actually.”

Salesman handing over car keys

In most cases, a digital strategy implies some kind of change. You want that change to be positive, and it always looks great in the planning sessions. Only when we hit the road does the reality check come. Even a change that’s going well can be hugely disruptive to business as usual. All too often changes stumble in the transition, and in the worst cases, the actual future state can be worse than the current state.

But don’t stress – with some good planning and understanding upfront, these sorts of problems can be largely avoided. Having a solid understanding of the nature of change is essential to successful transformations and there are good reasons to be wary of over-promising followed by under-delivery.

We like to think of each transformation as crossing a valley on the way to a higher point. For a while, you may be going down, but you have to get to the bottom of the valley to get to the higher ground on the other side – there is sometimes a little short-term pain, but it’s worth it for the gain.

Be open to fresh, new ideas

Henry Ford supposedly said:

If I’d asked people what they wanted, they would have said faster horses!

This phrase has been trotted out at every conference on digital transformation since the noughties. Incidentally, there’s no record that Ford ever said that explicitly, but it is clear that he held that sentiment.

Of course, customers’ views are important, but if you’re asking your vendor to supply you with faster horses when a far better alternative is available, you’re on the back foot straight away.

Another analogy I like is digging trenches. If you want to dig trenches, the options are clear:

a) Hire a bunch of low-paid people with shovels. If you want to dig faster, get more people and more shovels.

b) Rent (or buy) a mechanical excavator and hire one highly skilled person to drive it.

All things being equal, option b will generally work better, unless your business is based somewhere where mechanical excavators and skilled people are in short supply.

Never let your perception of what is possible limit your options. There are no technology problems really - there are only time and resource problems.

Make sure your people are on board

People are always the largest element of change, and digital or business change is no exception.

Make no mistake, changing the technology that people are using day-to-day is about the most personal interference you can make in their work lives. For the most part, people will get excited about the thought of an upgrade, but that doesn’t mean they’re going to like it when the inevitable teething problems occur. (I still have nightmares from implementing the jump company-wide from Windows 7 to 8).

Man and woman holding team meeting

Ensuring that your people are fully aware of the reasons for and the goals of your transformation effort is crucially important. It’s not possible to over-communicate in this space; steady leadership and ownership from the top are required, together with a sense of humour and a willingness to admit when things aren’t going too well.

Listening skills and proper training are key here. If you get feedback that something isn’t working, see if you can provide further lessons or hands-on tech support, for example. You need to discern between what is simply an unwillingness to accept change and what might actually be an issue and work through each challenge appropriately.

Be ready for the next challenge

When you have crossed a valley and climbed to the top of the other side, it is very likely that the next thing you will see is ... another valley! The process of growing a business is never-ending and the same is true for digital transformation. Even the most sophisticated companies will want to keep going, and they should.

Ongoing iterative change is the only way to stay ahead of the competition and ensure the digital and business strategies are aligned.

It can be daunting not knowing what the future holds, and one way to be prepared to take on the next opportunity is to start upskilling your team now. Yes, you too! Take a look at your executive leadership and management. Who could use development in digital tech? Do you even have someone knowledgeable about tech in your senior leadership? Looking a bit further down, there may be people that are ready to take the next step and would be awesome to move into a position to lead or drive strategic change.

Man hiking in New Zealand

If you can shift your mindset to consider “digital” to be an agile process and a core part of business, the sky is the limit. Digital tech isn’t just about administration, it’s how your business will grow and get ahead. As CEO, your attitude towards challenges and change will be reflected in your team and they’ll look to you to set the tone for how your business uses digital to thrive. Celebrate your successes, take a rest and move on when you're ready. Each success will make you and your organisation more resilient and confident to adopt ever greater challenges, and before you know it, your digital strategy will be helping your business strategy become a reality.

Ray Delany is the Founder of CIO Studio, a company built to partner with SMEs and help them solve the “strategy” problem and align their digital investment with their business outcomes.


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