5 Ways to Ensure Your Digital Transformation Succeeds

A business leader enjoying a successful digital transformation at her organization.

Thanks to apps like ChatGPT and Bard, leveraging generative AI has become accessible to anyone with an internet connection. While questions of oversight and regulation will continue to be raised, companies are seeking ways to turn this disruptive technology into opportunities. According to Deloitte’s 2024 MarginPLUS survey, 79% of respondents report that their company is utilizing genAI to “drive efficiency, innovation, and improve customer and employee experiences.” Likewise, Bloomberg Intelligence predicts that the genAI market will grow to $1.3 trillion within the next decade. For most companies, implementing this powerful technology requires initiatives in digital transformation.

What is digital transformation?

Digital transformation is not simply adopting new technologies — it’s restructuring existing processes and business operations to imbed technology into the core fabric of the organization. Those companies that successfully transform their operations create greater value, lower costs, and improve customer experience. Digital transformations prioritize continuous improvement for long-term success.

The hard truth about digital transformations

This kind of full-scale upheaval isn’t without risk. First, digital transformations can have significant start-up costs. Statista and IDC forecast companies will spend between $3-7 trillion in digital transformation investments by 2026.

Unfortunately, not all of these investments will bear fruit. Only a third of digital transformations meet or exceed their objectives, according to the Boston Consulting Group (BCG). Similarly, Harvard Business Review reports that two-thirds of leaders have “experienced at least one underperforming transformation in the last five years.”

Often, these failures are due to an underestimation of the scope involved in a digital transformation. While wanting to adopt the latest technology as soon as possible, organizations often overlook crucial planning in terms of change management, including adequately preparing and developing leaders, hiring the right talent, clearly communicating expectations, goals, and value-added of the changes, managing employee reluctance, and more.

“When organizations plan these digital transformations, they plan the digital part of it. They plan the execution, the tactical part of it. What they don’t plan is the change management part of it,” says Lori Mazan, author of Leadership Revolution: The Future of Developing Dynamic Leaders

Successful digital transformations are possible

Despite the odds, implementing a successful digital transformation is possible when organizations align their people-strategy to their tech-strategy. Rewiring an entire organization requires engaging and empowering employees at every level — many of which may feel uncomfortable or even threatened by the proposed changes, while others will hold onto entrenched beliefs or behaviors. 

“Digital transformation requires change, especially in people involved in the process. This is extremely difficult — not only does leadership need to be aligned, but the whole organization often needs a cultural shift,” says one Forbes Technology Council member.

Here are five ways to engage your workforce and boost your odds for a successful digital transformation:

1. Embrace clarity and transparency

To lay the foundation for a successful digital transformation, organizations need to be clear about the goals and desired outcomes. While the strategic view is often shared with and understood by top level executives, the messaging can get watered down as it makes its way to those who will actually implement the transformation. This can result in misalignment between functions, as well as increased resistance to change. 

Yet, companies who commit to communicating clearly the what, why, and how across the organization benefit greatly from increased understanding and conviction. McKinsey found that organizations that “fostered understanding and conviction are 3.2 times more likely” to outperform their competitors after initiating their transformation.

Clear communication and transparency can’t only occur during the initial stages of a digital transformation, however. Throughout the process, organizations must provide clarity on progress, setbacks, and pivots to everyone involved.

2. Empower employees at all levels

Instead of ignoring the anxieties a digital transformation can invoke — or worse, give false assurances about the implications to workers — companies must empower employees through frank conversations and opportunities for development. 

As mentioned above, clear communication is essential to a successful transformation, but companies must ensure that employees feel empowered to voice their own concerns. Change, especially on this scale, is an emotional journey, but those companies that create “create psychological safety and construct mechanisms for all voices to be heard,” can turn those emotions into “accelerators rather than inhibitors of transformation,” according to Harvard Business Review (HBR).

Upskilling or reskilling workers can help alleviate fears over potential job losses and it ensures that your organization has the talent needed to carry out the digital transformation. The World Economic Forum estimates that 44% of workers’ core skills will be disrupted by 2027. This means our current tight labor market will get even tighter for companies looking for workers with relevant skills. Investing in your employees’ development now can help your organization stay ahead of the competition — both in the market and in the talent wars.

3. Enable flexibility and exploration

Set-in-stone plans no longer work against the backdrop of exponential technological change. The technology you plan on adopting in your digital transformation may be obsolete within the first few years of implementation. Likewise, the rate of change and volatility on a global scale can have wide implications for your business. Agility and flexibility are vital to any organization’s survival and ability to thrive today.

A key, but often overlooked component of flexibility is the willingness to fail. HBR finds that transformation processes that are “designed so that failed experimentation would not negatively impact” the careers of those involved are nearly 2x more likely to succeed. BCG also recommends that organizations and their leaders adopt a “fail-fast-learn” approach in digital transformations.

This can be difficult, as companies, leaders, and workers are used to operating in a way that avoids failure. Afterall, failure isn’t easy; it forces us to instinctively revert to survival mode. Yet, innovation requires failure as it provides insights that cannot be obtained otherwise. 

“Once you get out of survival mode, then you can focus on what you learned from this failure, rather than obsessing about its consequences,” says Mazan.

4. Equip leaders with the right capabilities

Leadership can make or break a digital transformation. To flip the odds of success for a digital transformation, leaders must be dynamic with the capabilities to manage change, think strategically, and be self-aware, empathetic, and decisive. 

These capabilities enable leaders to role model change, while influencing others in the organization to do the same. Organizations where leaders role model desired transformational changes are “1.6 times more likely to report outperforming their peers,” according to McKinsey. 

But finding leaders committed to shifting their own behavior, as well as their direct reports’ can be difficult. In a study conducted by Deloitte and MIT Sloan, 87% of C-level executives “acknowledged that they don’t have the right leaders” in place to handle digital disruptions and transformations.

Fortunately, developing leadership capabilities can also help shift leaders’ mindsets and behaviors to better align with the strategic goals of a digital transformation. For example, leadership coaching is a form of vertical development that contextualizes capability-building to the organization. Leadership coaching also challenges leaders’ current mindsets and behaviors through outside perspectives and exploratory questions.

5. Enlist the right partners

As we mentioned earlier, time is not a luxury most organizations can afford during a digital transformation; the rate of change is too great. Embracing clarity, empowering employees, enabling flexibility, and equipping leaders must happen with the same sense of urgency. That’s a lot for any organization to handle on its own, so enlisting partners who can help you keep pace is crucial.

For example, when choosing a vendor for leadership development, factors like program scalability, flexibility, and speed-to-impact should be considered. 


To strengthen commitment throughout the organization, leaders at all levels need to have the capabilities required for change management. Look for a vendor who can help scale your leadership development programs easily.


Generic, out-of-the-box training cannot address the complexities and unique challenges your leaders face. As McKinsey points out, “In many organizations, capability-building programs aren’t integrated into employees’ on-the-job experiences,” leading to a huge blind spot in development programs. Find a vendor that can tailor their solutions and programs to your specific needs and contextualize development to your organization.


Deloitte presses the importance of speed-to-impact for digital transformations; “incremental improvement is not enough to win in today’s exponentially disrupted business environment.” The same is true for leadership development. Look for a vendor who pushes leaders to make dramatic leaps toward building essential capabilities.

Accelerated Leadership Development for Digital Transformations

Sounding Board understands your sense of urgency. That’s why we work to accelerate the development of leaders at all levels. Our coaches begin each engagement with identifying the Big Leap leaders must take to become more effective and have greater impact within their organization because incremental development is not an option in today’s fast-paced environment.

Hit the ground running with your digital transformation by developing the leaders you need now. Request a demo today.

See Us in Action

See how Sounding Board is revolutionizing leadership development through its coaching platform.

Related Articles

January 22, 2024
In 2023, I took a Big Leap. I took a career break to reconnect with my inspiration and intentionally pursue what I really, really wanted in life and in my career.
March 2, 2023
Traditional women in leadership development programs are great in theory, but not in practice. They’re built on faulty assumptions and mindsets.
May 23, 2024
Read our guide to learn what leadership development programs are available and how they can benefit your organization.
May 2, 2024
Dr. Laura Dannels, Chief Talent Officer, shares insights from Wellstar Health System’s leadership coaching program in partnership with Sounding Board.
April 25, 2024
We’re unpacking our joint Flash Report with HRO Today to uncover why so many leadership development programs fail to deliver results.

Transform Your Leadership Bench

Explore your end-to-end solution for leader transformation.