How the Smartest Leaders Use Storytelling to Drive Digital Transformation

WalkMe Team
By WalkMe Team
Updated May 2, 2023

Why does everyone know Steve Jobs?

A few reasons. First, his reputation as one of the most important tech pioneers is merited.

From the first Apple computer to the iPod to the iPhone, Apple technology unleashed a new level of computing into consumer products. Jobs satisfied the demands customers didn’t even know they had yet with the perfect blend of innovation and original UX.

But there’s another reason Steve Jobs is a household name. Storytelling.

At shareholder meetings, to staff, to the general public, Jobs routinely used storytelling to drive his point home.

And he mesmerized his audiences.

He plotted his narratives carefully. They always contained a dilemma or challenge. He painted a clear picture of right and wrong, winning and losing, and illustrated the high stakes of failure. He created an emotional connection to his audiences, and most importantly, he left them feeling inspired.

Jobs was a visionary, and his personal life made for a few good movies. But he is one of the most famous CEOs because of his ability to move people through his stories.

In an ever-evolving business narrative, storytelling is the only constant

Storytelling has existed for as long as humanity. While it’s not a new communication mechanism, many leaders fail to take advantage of its potential to help them connect with employees, clarify their vision, and drive transformational success.

During digital transformation, you need a high level of employee buy-in. Resistance to change can derail even the most carefully planned digital strategy, and leave your software investment in flames.

You need your employees to believe in your company’s goals and commit to achieving them. You need them to understand how your new strategy will improve business, what’s at stake if the company fails, and what’s in it for every individual.

Communication deficiency is at the root of every digital transformation failure. Effective communication is the key to successful change, and storytelling is the smartest leaders’ favorite secret weapon.

This craft element of storytelling is the key to achieving employee buy-in

Without authentic support from your employees, the potential of your digital transformation is immediately capped.

Resistance to change is the antagonist in your digital transformation. It makes employees refuse to change, reject new tools, and harm business performance. But with the right communication techniques, you can remedy many of the anxieties that contribute to resistance.

The most important “craft element” for telling your digital transformation story is relatability, according to Jason Miller, Content and Social Marketing Leader of LinkedIn Sales & Marketing Solutions EMEA.

“In order to change someone’s perception, you need to tell a story that they can relate to and inspires them to be a better employee,” says Miller. “You need to show your audience that they can do it too, that it’s within their reach.”

You can’t truly motivate your workforce if they don’t find an authentic personal connection to your goal. The story you create has to inspire your employees, make them believe in the desired outcome, and see what’s in it for them.

How to leverage the power of influence (Hint: You can’t do it alone)

As technology becomes increasingly embedded in the overall business strategy, CEOs have emerged as the lead authors of the digital transformation story.

It’s up to them to find the vision and craft the right story to share with the rest of the company. According to Miller, Jeff Weiner, CEO of LinkedIn, has boiled this down to a transformation

“Jeff Weiner tells great stories or anecdotes. He makes you feel like you’re part of something bigger. He knows how to get everyone to come along for the ride,” says Miller.

A CEO must “create stories that make everyone feel part of something bigger, that make people share your values and move the whole organization forward,” he added.

However, CEOs can’t do all of the work alone. When you’re pushing digital transformation, you need to constantly reinforce your mission — your story. Often, CEOs are too high up the corporate hierarchy to do this work.

Dive deeper: 3 Ways to Become a Successful Change Leader

Instead, leave that up to managers.

Your managers are the ones who work with and talk to your employees on a daily basis. They are the ones who must reinforce your digital transformation story in every meeting, during each conversation, and every time they answer a question.

“CEOs must tell their story, but then let it trickle down and let managers do the rest,” says Miller. “There’s too much hierarchy between employees and the c-suite. You need [managers] to show them what’s possible and tell them what’s in it for them.”

And while there will always be the laggards who struggle with the momentum your digital transformation demands, there will also be those for whom a little inspiration can go a long way.

A Digital Adoption Platform (DAP) makes digital transformation easy. Request a demo today.

Empower your employees to become storytellers and gain champions

Don’t make the mistake of ignoring the stories of those within the ranks.

Your employees’ stories are valuable for three main reasons.

  • Improve employee onboarding. Their personal experiences with your digital tools, or even past experiences from a prior employer, can inform improvements to your employee onboarding strategy. Think of it like a workshop, where everyone’s input helps refine one polished product.
  • Groom digital transformation champions. Employees with positive stories can turn into champions for your digital transformation effort. Raise their anecdotes to the forefront — publish them on the company blog, use them to kick-off a meeting — and watch how fast they influence others to adopt the same attitude. change leadership
  • Encourage brand ambassadors. LinkedIn employees often write company “appreciation posts,” which garner hundreds or even thousands of likes on the platform. When employees share their personal stories, people within and outside the company can relate. This not only spurs engagement, but it also helps promote the positive brand image LinkedIn has created.

When employees have a voice — when they feel like their stories matter — they will be more engaged. They will feel a greater sense of ownership in the dialogue that’s guiding your digital transformation, which is essential to eliminating resistance.

The essential rule of storytelling

The most important principle of storytelling is having a clear point. Employees and customers today expect their leaders to have a strong presence, and to engage in daily happenings as much as possible.

When driving enterprise-wide change, this is critical. Your stories are the headlights that guide your organization down this journey.

“CEOs are like the lead singer of a band,” says Miller.

Their faces need to be known, and their voices heard.

In the digital age, in which transparency in the C-suite is becoming the expectation, leaders must make their stories accessible. Those who project an authentic voice will be more credible in the eyes of their employees, which is essential for gaining support and making change happen.

For example, Jeff Weiner makes it a point to respond to as many LinkedIn employee posts on the platform as possible. change management

This kind of communication helps continually reinforce the messages Weiner sends his employees. It also makes employees know for a fact that their stories are being seen, acknowledged, and considered. This helps raise engagement and company loyalty, which are essential during digital transformation.

Don’t reinvent the wheel

Digital transformation is a complex, resource-intensive process. Without enough clarity surrounding the changes and why they are occurring, resistance, stress, and frustration are bound to arise.

There’s no need to search for a novel approach to communicating the changes ahead. Tell a story. Captivate your audience by making them relate. Inspire them to be proactive and promote the changes necessary for your digital transformation to succeed.

Up next on your reading list: The CEO’s ultimate digital transformation playbook.


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.