Habit # 1: Outsource Your Vision to a Successful Digital Transformation
(Taken from the Secret Playbook for Screwing Up Your Digital Transformation)
The first thing a leader can do to screw up a digital transformation is to develop a poor picture of what it looks like for their business. This opens the way for others to define it and ultimately lead the business away from setting its own vision.
Find out how this unintended habit plays out in the first of a series of tactics from the Secret Playbook for Screwing Up Your Digital Transformation!

Most people know what a successful digital transformation is – even though they don’t
There’s a lot of literature to explain what digital transformation is. Yet it doesn’t always agree.
That’s because each community involved in digital transformation has its own take on what successful digital transformation is. You’ll find the analyst community describing it with their slight variances. Or the service provider/system integrator community, who is afraid of being left behind, putting a unique stance on the definition. Or the software vendor community narrowing the context so they can put their products out to the market in many forms and push successfully into your business.
This creates a lot of noise for the business leader who simply wants to understand what it is and how it can help their business.
How you understand digital transformation significantly affects the success or failure rate of a project. Particularly at the start of the process.
To cut through the noise, a diligent leader will not only read the articles but attend seminars and seek out the opinions of others. But at the end of it all, remain unclear …with one exception. They will know that digital transformation is important and how it can help their business into the future.
This might be a bad start if you’re expecting a successful outcome. But it’s a great opportunity for screwing up the transformation.
Maintaining a poor picture of what digital transformation is
Consider the confused leader who just can’t cut through all the noise. In this example, we’ll call him Larry.
Larry is convinced that digital transformation will solve a few pain points in his business, even though he is not sure how. And he is afraid of not embracing it now for fear of falling behind his competitors.
Larry brings these pain points to the executive table and explains the benefits to the business without explaining how. How can he? He doesn’t know what digital transformation is. But he needs to project an air of confidence to achieve full buy-in. That’s something he knows all about as a leader.
Larry does a great presentation and is perceived as the expert. Fortunately, those in the room know a lot less than he does to ask any tricky questions. The executive leadership at the table nod their heads and agree to the next step of setting up a tiger team.
The Tiger Team is made up of nice people within the business who also don’t understand much about digital transformation. But they are happy to rely on Larry’s expertise and confidence. Despite a few niggling questions they might have. They don’t want this to get in the way of progress and they assume any issue can be sorted out later…
Where does this leave them?
The problem in this very common scenario is that no one is clear about what they are trying to achieve. Or what form digital transformation needs to take within the business to achieve the business’s unique vision and outcomes.
This is a serious problem for a successful outcome.
But perfect if you still want to screw up the digital transformation!
Let me explain.
Let others define what digital transformation means for your business
The first step to screwing up your digital transformation is to help leaders maintain a poor picture of what digital transformation means for their business. You can do this by exposing them to all the noise around what digital transformation is. Yet you must also continue treating them as the expert. The more you talk and treat them as the expert, the harder it will be for them to admit they don’t understand all this stuff!
Next, encourage compliance amongst the people reporting to the leaders so they are less inclined to ask tricky questions. You don’t want to undermine the leader’s confidence in their expertise.
This then opens the way for outsiders to enter the business and provide solutions that are easy for them to implement and make money from. Yet not necessarily tailored to real business outcomes
The first outsiders to enter your business are likely to be service providers. Remember that while they have your best interests at heart, they are not going to know the business as well as the leaders. But since they’re good at implementing the same generic solution across many companies, they’ll have the confidence to offer and deliver a glossy solution that looks great on the surface. Even if it doesn’t serve the vision.
Your next “outsider” who can influence the business direction is the software vendor. Vendors come in a range of sizes. Remember they come to you with code or pre-configured modules set up to work a particular way. This way doesn’t always align with the way a business operates. Without strong leadership and clear direction, they can deliver a generic solution without the obligation to tailor it more specifically for business efficiency or growth.
The outcome is that you can let others define the digital transformation for you. The result is something that does not work best for your company.
How to know this tactic is working
You probably won’t know this tactic is working until halfway through the project.
This is because the renewed sense of confidence you enjoyed at project kick-off should last at least to the project’s midway point. This is when leaders start getting a taste of what the software looks like and how it meets some of their requirements but not all. It will also highlight some significant gaps that could have been avoided if the digital transformation was properly understood and defined from the start.
You’ll really know this tactic is working when you start hearing inside your head, a series of “Oh crap!” statements:
- ‘When do I speak up…or can I get away with keeping quiet?’
- ‘What’s best for my career here?’
- ‘Who can I blame …there are plenty of places to turn?’
- ‘It’ll be right, we can get away with over-representing the benefit and we’ll fill the gaps later’
Getting cold feet...?
Whilst I can guarantee this approach will work well for a little while, you may be having second thoughts. You may be asking “Do I really want to follow this tactic from the Playbook for Screwing Up Your Digital Transformation”?
Don’t worry. It takes a lot of guts to implement this consciously. But the good news is most companies do it automatically as an unintentional habit. It’s part of human nature.
But if you still feel uncomfortable about screwing up your digital transformation, you can also work against the grain and aim for success. In some ways, it’s a lot harder than just letting things flow and watching a business fail.
We help medium-sized businesses go against the grain to implement successful digital transformation. This includes helping executives understand and define digital transformation for their business so they can be sure that the outcome supports your vision, grows your business, and can sustain itself into the future.
Look out for my next article where I reveal the second habit from the Secret Playbook for Screwing Up Your Digital Transformation. It’s a deceptively simple tactic that involves spreading accountability to de-risk our digital transformation.