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Digital Transformation: 10 Dos and Don'ts for CEOs


If you’re not taking advantage of present day digital technologies, you’re missing out on a potential competitive edge.

In fact, according to Forrester Research, 56% of business and IT decision makers claim that their digital transformation is already underway.

What does a digital transformation look like?


Here are some examples of companies are missing out on digital transformation opportunities: Consider a brick-and-mortar bookstore that doesn’t also sell online. By letting ecommerce technology pass them by, they’re missing out on a ton of potential sales!

What about a payroll outsourcing company that doesn’t use an automated payroll processing system? They’re going to be burning resources trying to compete with others that do use an automated system.

Those are some obvious, surface-level examples, and we could go much deeper and more granular. The point is this:

Would you rather be a company that gets stuck in the past and is forced to burn more and more resources in order to compete? Or would you rather grab onto new technologies before they fly by you?

If you said you’d rather grab on to new technologies, get ready, because digital transformation can take your company to new heights!

So you’re ready for a digital transformation?

Digital transformation is more than a single project. It’s more than a fad or an empty buzzword. What is digital transformation? It’s a movement. And it’s a growth strategy.

How can you launch a successful business transformation? These things don’t happen on accident. Your strategy must be well planned and heavily researched if you’re going to succeed. On top of running calculations of investments and predicted ROI, you’ll be recruiting champions for change and enforcing new policies that some people may be uncomfortable with at first.

You may experience growing pains, but you’ll focus on the first part of that phrase – growing.

As the saying goes, nothing worth doing is ever easy.

Today, we’re going to dive into the 10 Dos and Don’ts of Digital Transformation, so that you can get started on the right foot and finish at the head of the pack.

#1: DO some heavy planning

Prove the concept. You already know how to make a business case for your fellow execs or board members. This isn’t any different. Focus on the area where you’ll begin the transformation, and prove your process improvement plan will work. You don’t have to plan it all at once, or include every single details in your case. One department or one single process could represent the whole, unless your colleagues press for more details.

prove your plan

Calculate the expected ROI. Many platforms offer ROI calculators (like this one). If there’s not one available to you, speak with a consultative salesperson about your plans for transformation, and get data-based ROI estimates in writing.

Pick the right software and the right partner for change. Digital transformation is an ongoing process, and you’ll be spending a lot of time with your software vendor. Find one that is willing to partner with you and walk you through each step. Sometimes the best bet is going with a boutique shop that has a highly configurable product and is more focused on services instead of just the software project. You’ll need more than just a business transformation framework. You’ll also want a team of experts who can support and guide you along the way.

#2: DO find champions for change

champions for change

Get a change manager on board. An experienced change manager will bring a structured approach to implementing each stage of your digital transformation project.

Pick a team of experts who will help plan and implement the change. Beyond the support of your vendor, you’re going to want people who will become internal experts.

These should be great communicators who can promote the project internally. Not everyone is going to feel comfortable asking you, the CEO, if they have questions or concerns about certain changes. But if there are people spread throughout the company in various departments, who are all part of your digital transformation task force, they may be able to help address concerns on a less formal level.

#3: DO maintain your focus

Wait to launch until your organization is ready to make the project its top priority. When the budget and the buy-in align, you’ll know it’s time to get cracking.

Once you’ve begun, don’t get sidetracked by other projects your team is asking for. Just like you waited to begin the first stage of your business’ digital transformation, other projects can wait their turn.

Stay focused until you’ve achieved your goals. Don’t let the project get derailed or stale. This is easier if you break the transformation down into bite-sized goals. That way, you can approach it as a series of sprints, rather than a marathon.

#4: DO provide training and support

Your project isn’t going to go anywhere if you can’t get your team on board. Consider how you will deliver the news that some things will be changing, and the supports you will need to provide to make people feel more comfortable with the changes.


Alleviate fear of change by providing training and Q/A opportunities. As you adapt your processes to new technologies, the training will be twofold. First, you’ll need to provide basic technical training on any new systems you’ll be using. Second, you’ll need to make sure people understand that some parts of the process will be different. For example, if you’ve automated certain steps, like data entry, their time will be reallocated to other steps of the process, or even other processes altogether. Provide ample training opportunities and the opportunity for people to ask questions.

Designate resources your team can approach if they need help. This goes back to your champions for change. Make sure you have people who are in-house experts of your new technology and processes, and ensure that there’s a plan in place for when your team needs technical support.

#5: DO enforce new policies and procedures

If new procedures aren’t enforced, you won’t see the ROI you’re anticipating. Make sure that your new procedures are in line with compliance requirements, as well as any other internal and external policies.

Don’t let team members continue to do things the old way. While this sounds impossible at first, you may have more control over this than you think. For example, if you’ve changed to a paperless system, and your team is accustomed to going to the file room to retrieve documentation, the solution may be as simple as phasing out the file room. If your team is accustomed to filling out paper forms for Purchase Requests and placing them in a physical inbox on the CFO’s desk, and you’re trying to get them to fill out an electronic form instead… ditch the Inbox! Put a notice in its place that explains how the new process works and who can help if they need assistance.

Conduct periodic check-ins to ensure that your vision is being carried out. Call in your change champions for check-ins to see how everyone is adapting and if you’ll need to intervene.

#6: DON’T forget to set goals


Set short-term goals and long-term goals. As we’ve already established, digital transformation is an ongoing process. As new technologies are developed, you’ll continue to adapt and improve along the way. In the meantime, it’s important to set short-term goals, too, and to recognize the progress you’re making.

Celebrate and recognize the achievement of each goal. Whether it’s the elimination of a single filing cabinet or the automation of your AP processes, make sure you’re celebrating the completion of each goal!

Ensure that everyone recognizes the progress of the company and individual teams. Change isn’t an easy thing, and it’s even harder to get everyone on board with you once you’re ready for change. Boost morale and keep your team in positive spirits by pointing out everyone’s achievements.

#7: DON’T let fear hold you back

Fear can keep you from growing. In fact, 45% of CIOs say that “resistance to change” is the #1 thing holding them back from digital transformation. Sometimes it’s difficult to look past the resistance perceived within a team.

We’re not saying to go leap blindly. Planning is key. But we’ve heard too many times from execs that they’re are afraid to make a change because they don’t think that their team will be on board. Don’t let this fear hold you back, or you’ll end up behind the curve and trying to catch up, without the technology and tools that the other guys are using to get ahead.

People who won’t change are people who can’t grow. It’s as simple as that. Don’t let fear keep you and your organization from realizing growth.

#8: DON’T stop learning


When you stop learning, you stop growing. As Albert Einstein said, “Life is like riding a bicycle. To keep your balance, you must keep moving.” Think about the rate at which technology is growing in our modern world. It never stops or slows down, and it’s certainly not going to wait for you to catch up.

Don’t set limits on yourself or on your team. When a member of your team has an idea, is he or she met with an immediate “we can’t do that” or “that won’t work”? Are you imposing limits on your team without even thinking about it?

Keep an open mind, and be willing to experiment and learn new strategies. Consider companies like Google. Their employees are encouraged to take risks and to work on their own ideas and projects. Without taking chances and thinking outside the box, it’s impossible to stumble upon truly great ideas. If you give people’s minds a forum to be creative, you may find that your team has its own ideas about what a digital transformation could look like in their home department.

#9: DON’T go it alone

You need more than executive buy-in. What about the rest of your team? Unless you’re at a pretty small company, the C-Suite isn’t generally on the front lines.

You need whole-company buy-in. Again, this goes back to your champions for change and your internal experts. Select the people who are going to represent your ideas best, with authentic enthusiasm.

Include your project team in meetings and decisions as much as you can. With a full-scale business transformation, it’s impossible for one person to hold all the knowledge required to make the best choices. Consider getting input from the people who have been at the company the longest, as these are the people who have the most tribal knowledge – the ones who truly understand why things are done the way they’re currently done and each of the important details involved in a process.

#10: DON’T do it all at once

When you go with an Enterprise Automation platform, all the doors fling open at once. With a robust document management and enterprise automation system at your fingertips, the sky’s the limit. But you can’t do it all at once.

Walk through one door at a time. If it’s difficult to determine where you’ll begin your digital transformation, it may be helpful for you to check out some other people’s stories and to self-educate on the possibilities. Check out the article “Enterprise Automation – Where Will You Begin” to learn more about where other companies have begun their digital transformations, or speak with an expert who can help you determine a starting point.

Approach your transformation as a series of small projects with achievable milestones. Before you know it, you’ll be ready to move on to the next, and you’ll begin to see a forward-moving momentum building at your organization.

Where will you start? And where will you go from there? The choice is yours.

For more tips that apply to any and all of your digital transformation projects, download our tipsheet, Overcoming the Top 7 Process Improvement Risks.

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Steve Allen

Steve Allen is the founder and former CEO of DocuPhase, a best-in-class, browser-based software that delivers unmatched efficiency to companies around the world by automating core accounting processes. He drives the innovation and product vision of DocuPhase to develop solutions to simplify the workplace.