First 100 Days of Digital Transformation: HR’s Essential Role in Driving Success

WalkMe Team
By WalkMe Team
Updated December 6, 2023

When Franklin D. Roosevelt was elected, he had no time to stall. The US economy was in a dire state, unemployment was widespread, and the unshakable American spirit had been displaced by despair.

FDR proved his administration would bring serious change and transform the ailing economy with his history-making first 100 days.

Anchored by the New Deal, FDR launched a broad range of initiatives to achieve economic recovery and provide relief to millions.

His transformation plan worked. FDR’s success in the first 100 days made him an American legend and established a new litmus test for leaders: Your accomplishments or failures during the first 100 days indicate your overall ability to succeed.

Without a robust HR strategy, your digital transformation will fail fast

During digital transformation in enterprise, the first 100 days are critical for setting the pace, attitude, and success with which your employees will adopt new digital tools.

Yet too often, leaders don’t realize how much their human capital affects the success of their digital transformation.

They allocate disproportionate attention, resources, and strategy to the technology piece of the puzzle, and hardly any on the people piece.

This is a fatal mistake. Of all the factors that influence the success of your digital transformation, the human factor is the biggest.

If anyone understood how much people affected the success of a large-scale transformation, it’s FDR. His ability to promote coordination and support across a divisive political landscape is what enabled him to transform the American economy from broken to barreling. His ability to uplift the American people and move them to action is how he secured an unprecedented four terms in the White House.

Why business leaders underestimate HR’s role in digital transformation

digital adoption

Why do so many leaders make the same mistake in their digital transformation strategy? Why don’t they give the human factor enough weight?

According to Andrea Schnepf, Principal Management Consultant at nepf LLC, it’s because technology used to be the major limiting factor to progress. It consumed all of leaders’ attention, and subsequently, all of the resources.

But technology doesn’t impose the same constraints as it used to. Today, the opposite is true — it creates a broad range of new opportunities.

“In today’s world, what we find is that technology growth is so exponential, which means that now really almost anything is possible from a technology perspective, and it’s actually the ability of the people and organization to adapt and adopt that has become the limiting factor,” says Schnepf.

Failing to recognize this raises an impassable obstacle to digital adoption, or the ability of your employees to use digital tools to their fullest extent and as intended.

“For many experienced business leaders, those past headaches to making the technology work is still what may look like the first priority to address. However, they often find that actually, the technology is now becoming relatively easier. Where transformation efforts get stuck is when it comes to adoption by the people.”

Dive deeper: Why your digital transformation will fail without a digital adoption strategy.

The first rule of digital transformation in enterprise

digital transformation in hr

Before even entering the planning stages of your digital transformation, you must dispell the “companies are machines” mentality.

They’re not. Instead, they’re more like ecosystems, according to Ben Ralph, Head of Product and Experience at Beaker & Flint.

“Organizations are made up of people, and people are emotional and complicated,” says Ralph. “All too often, leaders see their staff as resources or ‘parts of a machine’ that can just be deleted or moved around. In my experience, people do not respond well to top-down, command and control style transformation.”

Instead, Ralph says leaders need to take an evolutionary approach to change, especially when it comes to digital transformation in enterprise.

“As a leader of change, you plant a seed and create the right conditions for it to grow,” he added.

Getting the right people on board, acquiring important skills, and cultivating authentic support won’t be the result of an authoritarian leadership approach. It won’t even come from perks or monetary incentives — at least not in the long-term.

To reach these outcomes, you must first address the many ways that human resources affects digital transformation.

We broke it down for you here.

4 areas where HR initiatives can make or break your digital transformation

The first 100 days are the most vulnerable. This is when all eyes are on you.

Your stakeholders are looking for an ROI. Your employees are looking for direction. Your skeptics are waiting for something to go wrong. You can’t afford mistakes or crises, or the credibility of your digital transformation strategy will decline.

Here are four ways your HR department influences the success of your digital transformation within the first 100 days.

1. Talent and skills development

Having the right people within your ranks is critical for success during the first 100 days of digital transformation, and beyond.

But what exactly does “the right people” mean? From your C-suite executives to your interns, certain traits, skills, and attitudes better cohere with your values and enable you to achieve your goals.

“An innovative mindset, agility, digital literacy, risk-taking and tolerance of ambiguity are key attributes that seniors need to exhibit to promote the right employee behavior during this tough journey of digital transformation,” says Karippur Nanda Kumar, PhD, Associate Professor & Area Head of Information Technology at SP Jain School of Global Management.

In both recruiting and employee development, knowing which employee skills will support your digital transformation and uphold a digital culture is imperative.

HR leaders are increasingly abandoning the long-held focus on experience in favor of attitude, intelligence, and aptitude.

The ideal candidate today is adaptable and flexible. They have a strong, intrinsic desire to always be learning. They have an experimental, creative, fail-fast attitude. But most importantly, they are doers. They embrace challenges and uncertainty as opportunities to grow, and they’re growing all the time.

2. Employee experience

employee experience

Your employee experience makes or breaks the success of your transformation.

That’s why it’s critical to assure your workforce that their roles, workflows, and productivity will ultimately improve as a result of the new technology, not contribute to employee frustration, or worse, burnout.

Up next on your reading list: The hidden factor that’s fueling employee burnout

“If employees suffer a bad experience, or if an implementation goes wrong and stalls workforce progress, employees will look at any additional changes skeptically and as though they, themselves, could do better — this is not good territory in which to be,” says Zachary Chertok, Research Analyst of Human Capital Management at Aberdeen.

HR must keep a constant pulse on the workforce through the first 100 days to ensure that they are addressing an initial employee resistance.

They must also ensure employees aren’t getting stuck along the way or justifying doing things the same as in the past instead of embracing new tools and processes, according to Chertok.

Proper training and support is the key to protecting the employee experience during digital transformation in enterprise.

3. Culture

HR plays a primary role in crafting and upholding the type of culture and norms that will promote successful digital transformation.

According to Schnepf, there are three ways leaders within HR and across all departments can embed desired behaviors into the culture.

“Firstly, senior leaders must lead by example and make a conscious effort — and hold each other accountable — to demonstrate the targeted behaviors,” she says.

“Secondly, day-to-day processes must reflect the new target behaviors. For example, if a new reporting dashboard for management information has been developed, its use needs to be embedded in regular meetings. Thirdly, the processes and criteria on how employees are measured and rewarded need to reflect the type of behaviors targeted. For example, if the company wants to develop collaborative behaviors, then the performance management process shouldn’t ‘rank’ individuals against each other — a common process that kills collaboration.”

4. Managers

If you have bad managers, don’t bother with any wide-scale change effort, especially not digital transformation.

Managers are the ones who shape the employee experience — you could be doing meaningful work every day, have access to the best perks, and the highest salary of your career and still have a horrible experience if you have a bad manager.

Bookmark this: 3 essential leadership skills to make change happen

The classic tell-tale signs of a bad manager — foul-tempered, micro-managing, challenging, and confrontational — are still relevant today. These managers will drive your most valuable talent out of your doors and straight into your competitor’s arms.

But a subtler, less obvious fault can be impairing the success of your management: lack of accountability.

The best managers take on this challenging role because they love what they are doing, love developing others, and love your company’s strategic goal. They aren’t managers simply because they performed well and got promoted. They embrace the challenges, responsibilities, mentorship duties, and headaches with optimism and grit.

They care about their team members and tailor their approach to help each individual succeed. They provide thoughtful feedback and always give enough support.

In digital transformation, employees need extra support and assurances. They need to know their boss expects a temporary drop in productivity, and that it’s acceptable. They need a manager who will give them the training, resources, and morale booster they need during times of uncertainty or change.

It’s HR’s job to find these managers and reward them. Along the same vein, it’s HR’s job to dismiss those who aren’t up to the job — the success of your first 100 days and entire future rests on it.

During the first 100 days, keep your employees at the center

There is no part of digital transformation in enterprise that your HR department doesn’t affect.

From recruiting the talent that will help you fortify your digital strategy to developing your current workforce to weeding out bad managers, the importance of HR to digital transformation cannot be overestimated.

FDR didn’t transform the entire American economy in 100 days, but he planted the seed for sustainable, continuous improvement through the many initiatives he started. He was a super boss. Beyond his intelligence and ability to address the needs of the American people, FDR was a master at communication, driving projects, raising accountability, and seeing results.

The success of the first 100 days of your digital transformation sets the tone for the following period. There is no room for mistakes, and everyone in the organization must be onboard.

While technology you choose and the way you implement has a profound impact on your digital transformation. But nothing is more powerful than the people who use it.

Take a deeper dive into how human resources can become the ultimate digital transformation partner in our eBook, The First 100 Days of Digital Transformation: HR’s Essential Role in Driving Successful Change.


WalkMe’s Digital Adoption Platform (DAP) transforms the user experience in today’s overwhelming digital world. Using artificial intelligence, engagement, guidance, and automation, WalkMe’s transparent overlay assists users to complete tasks easily within any enterprise software, mobile application or website. Discover how a DAP can revolutionize your business — request a demo today.

WalkMe Team
By WalkMe Team
WalkMe pioneered the Digital Adoption Platform (DAP) for organizations to utilize the full potential of their digital assets. Using artificial intelligence, machine learning and contextual guidance, WalkMe adds a dynamic user interface layer to raise the digital literacy of all users.