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The Digital Transformation Checklist (Part 1)

EducationSummary: Digital transformation is a hot topic for many businesses these days. However, it’s a complex task. Many don’t know where to start, or what steps they must take in the process. In this article, we explore the first 5 points in your digital transformation checklist.

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Digital Transformation is a term we’ve heard thrown around quite a bit recently. It’s a topic that you can’t ignore, but one that’s surrounded with a lot of confusion. What does it really mean?

If you’d like an in-depth view on the topic, here’s a great article you should check out. It provides one of clearest definitions I’ve seen: “we define digital transformation as the integration of digital technology into all areas of a business resulting in fundamental changes to how businesses operate and how they deliver value to customers.”

In short, the world is going digital. The modern company must transform itself and adopt the technology and processes needed to operate in today’s digital world.

The problem: According to a recent report, 47% of companies haven’t started to embark on digital transformation. They’re already behind the curve.

The good news: According to the same report, 55% of companies without an existing digital transformation program say the timeframe to adopt one is a year or less.

The question: If you’re part of that 55%, where do you start? What do you need to have in place before you begin your digital transformation?

Today, let’s explore this topic in terms of a “digital transformation checklist.” These are steps that you can’t ignore if you want your project to succeed. As this is such a large topic, I’m breaking it up into two articles. We’ll cover the first 5 points on the checklist in this article, and follow up with more in a future article. Sound good? Okay, here is part 1 of the digital transformation checklist:

Create a clear definition of success

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Imagine that you’re in an archery competition. But, as you draw your bow and look towards the target, you realize something: The targets are blank. There are no lines. No bulls-eye. Nothing. How will anyone know who won?

Unfortunately, this is how too many companies approach digital transformation. They have a rough idea of where they’re aiming but don’t have a clear definition of success. Without a specific goal that’s clearly communicated to the business, the whole project risks failure.

“What is the vision for the company after the transformation has matured or completed?”, asks Sam Taylor, Senior Consultant at Coastal Cloud. “If the C-level suite has this idea of how they expect the company to operate and that vision isn’t encapsulated in the specific goals for the project, that can lead to the project being considered a failure.”

Besides avoiding failure, the other big reason why this is so important: If your team has a clear definition of success, you’re all moving in the same direction. As explained below, this means you can stop and regroup if you notice the project veering off-course.

“Avoid jumping into a project without defining what success would look like,” says Joanna Wyganowska, PMP at Infinite Leap. “Ensure you have a set of key performance indicators (KPIs) agreed upon to measure if you are on the path to success. And don’t wait with sharing if things are not going as planned, that’s your opportunity to regroup and ask for additional support to hit the end goal.”

Get the right leader in place

This is an often-overlooked step in the process. After all, your existing leaders can lead your digital transformation, right?

Not necessarily. Choosing someone to lead your digital transformation is just as important as defining success. This is a step on your checklist that you should not take lightly.

The right candidate must have at least two critical qualities:

First, they must know where they’re going. Not everyone has a solid grasp on digital technology, and how it applies to your business. In some cases, you’re fortunate to have people like that within your business. In other cases, as explained below, you have to look for outside help.

“My advice for business owners that are looking to step up their digital marketing and transform their businesses digitally are: Do your research there are so many people that say they are digital experts and often aren’t,” says Ross Weir, Managing Director of ‎H J WEIR Engineering Co. Ltd. “Find the right individual to lead the team and business and ensure their ethics and work rate aligns with yours and the companies.”

The second quality you must look for in a digital transformation leader: They must have the ability to get the business on board. After all, this is a big project and comes with a lot of change. Many users will resist this change. You need a leader who can communicate the benefits to the entire business, and get everyone moving in the right direction.

Get buy-in from all levels

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This might seem like an obvious step, but it’s critically important. Without complete buy-in, your project will likely fail.

What do I mean by “buy-in?” This happens on two levels:

First, you obviously need top-level buy-in. Your business leaders must be 100% on board before you begin. I specify 100% because a dissenting voice up top will trickle down into the business. When things don’t go exactly as planned, leaders who aren’t 100% committed will try to derail the whole process.

Secondly, you need buy-in from all levels of the business. After all, the end users will be likely be impacted the most by digital transformation. As explained below, you need to identify partners within the business who can help secure this buy-in.

“Because many professionals today already have a working knowledge of digital tactics, the potential for true digital transformation can be hindered by dismissive voices,” says Matt Chun, VP Digital Strategy at ‎Vanguard Communications. “Therefore, it’s important to identify and partner with colleagues at various levels that not only support your digital vision but also understand the work needed in facilitating a digital paradigm shift. First, you’ll need an influential, decision-maker (likely your supervisor) that can set the tone and expectations across the organization. This serves as air cover as your initial efforts will expectedly be met with skepticism. Laterally, you’ll want several peers with established credibility that can reinforce the rationale behind your efforts. Like kindling, these small but essential tools gain traction quickly, bringing forth early results to further spark the momentum. Just as important, you will need a support team that can manage the on-the-ground implementation and integration while you focus on the bigger picture.”

Create a process for handling the change

Digital transformation isn’t a small change. In many companies, it requires that employees operate differently. It means they must learn new technology. It means they must change.

The problem: People hate change. They get comfortable doing things a certain way. When they hear that they have to learn new skills or processes, many will fight it.

If not addressed, this can derail your efforts. As explained below, you need to set up a process for dealing with the changes.

“What most organizations forget, or don’t realize at all, is how difficult enacting company-wide change can be,” says Rob Ristagno CEO, ‎The Sterling Woods Group. “That’s why there are entire professions devoted to change management. If you can make room for it in the budget, bring in a consultant to help walk your team members through the process of undergoing a digital transformation. If you can’t, there are still steps you can take to set your team up for success. First and foremost, you need a process for the digital changes you plan to enact in the business. A good place to start is to state your goal. What change are you trying to make? Then, outline every single step it will take to get you there. Who needs to be on board? What processes and systems need to be revised? Baby steps, if/then scenarios and plans for team training will help you make sure that change flows down through your team steadily and successfully.”

Evaluate your talent

Digital Solutions require a new talent set–one that many companies don’t have. Before you begin, you must understand where your talent gaps lie.

“The first step before diving into a digital transformation is evaluating your existing workforce and their readiness for such an endeavor,” says Bob Clary, Director of Marketing at ‎DevelopIntelligence. “The best-laid plans will not be effective if you do not have the right talent to execute, and if necessary, you must bring these people into your organization one way or another prior to beginning.”

What can you do if you identify a talent gap, but don’t have the budget to bring in more talent or hire consultants? You have two options:

Set up education programs. Train your existing team on modern technologies. With all of the high-quality online education options available these days, it’s easier than ever.

Bring in software to bridge the gap. What happens if you need modern solutions today, but don’t have the time to train your employees? In these instances, you can bring modern skills to your current team in the form of tools. I know of many companies that adopt development platforms that let their existing employees create solutions they need.

In short, talent is a key piece to your digital transformation journey. If you don’t have what you need in-house, find a way to bridge that gap before you begin.


These are just 5 points for your Digital Transformation Checklist. We’ll cover more in an upcoming article. If you would like to add anything to this list, I’d love to hear it. Feel free to share in the comments.

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2 thoughts on “The Digital Transformation Checklist (Part 1)”

  1. The checklist that you described in this blog will be very useful to check those things when I am going to do a project.
    Thanks for the blog

  2. Really impressed! Everything is very open and very clear clarification of issues. It contains truly facts. Your website is very valuable. Thanks for sharing

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