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Never stop being human: How to spur digital transformation at your business.

Companies with the best outcomes for adopting new technology have a common strategy: Never stop being human. 


Illustration by Jordan Bogash

Choose your scenario:

Scenario #1: It’s rush hour, it’s frigid, and it’s raining. You grab your keys and head out the door. You get to drive 30 minutes to your downtown office to search for a document that’s in a filing cabinet in the records room. But you’re not positive which of the 11 filing cabinets holds the document. Night ruined.

Scenario #2: You’re brainstorming, and inspiration strikes! You remember just the right person to text about a new opportunity, but you don’t have their phone number. You think it’s buried deep in one of several 40-plus message email threads, all from 2018. After an hour of searching, you give up, and the moment of inspiration is gone. So is their opportunity.

Scenario #3: You must devise a Plan B 12 hours or so before your project meeting because you missed a contract deadline. In your rush, you accidentally attached an outdated contract in the email to the other party. (You sent “final_final_FINAL.doc” instead “final_final_FINAL-APPROVED.doc.”) Classic mistake. 

These three stressful scenarios all have one thing in common.

They’re all tell-tale signs of an organization in desperate need of a digital transformation, which is the ongoing adoption of cloud-based, responsive digital infrastructure to serve customers, employees, and the business.

While all of these examples end in different solutions, experts have found that the best practices for achieving a successful digital transformation are consistent across various pain points and industries. 

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The reasons for failure are consistent, too. According to a 2016 report by McKinsey, “70 percent of complex, large-scale change programs don’t reach their stated goals.” 

The report goes on to say that most transformations fail for the same reasons. Primarily there are shortages in employee engagement, support from management, cross-team collaboration, and accountability. 

In addition to those short-term blockers, there are long-term challenges. As the McKinsey report explains, “sustaining a transformation’s impact typically requires a major reset in mindsets and behaviors—something that few leaders know how to achieve.”

Digital transformations may be hard, but that doesn’t mean organizations shouldn’t try. After all, a successful digital transformation can reshape and improve a company’s culture and performance. But it does mean that leaders and stakeholders should research and heed tried-and-true best practices before embarking on a digital transformation. 

Focus on people as you choose your solution

The relationship between new technology and the people who use it is full of influential factors, which is why an organization must introduce, onboard, and fully integrate its workforce into the digital transformation process. Before even researching solutions, leaders should survey their team leads and determine what changes need to be made for a successful digital transformation. 

Michael Lewrick is an internationally renowned thought leader and author of a series of bestsellers, including Design Thinking for Business Growth. In his research, he’s found that digital transformations don’t begin with choosing a new tool or platform but with the perspectives of the people who will use it. 

Digital transformations don’t begin with choosing a new tool or platform but with the perspectives of the people who will use it.

—Michael Lewrick

“Digital transformation happens mainly in the minds of employees and top managers,” Lewrick tells The Workback. “This means that a new mindset is needed that is open to perceiving change as an opportunity.”

Lewrick’s argument for a new mindset is supported by research. According to a 2018 McKinsey report on digital transformation, “the workforce implications of digitization, automation, and other technological trends are significant, and companies will need to invest in and hire for radically different skills and capabilities. … One critical step is for organizations to develop clear workforce strategies to help determine the digital skills and capabilities that they currently have—and will need—to meet their future goals.”

A people-first approach requires leaders to incorporate their employees’ skills, abilities, differences, and tolerance for change into their digital transformation strategy. According to Boston Consulting Group, organizations that are adept at digital transformation have three priorities in common: “a relentless focus on the outcomes that matter; [discovering] new ways of working; and savvy use of digital and technology.” BCG calls these companies “bionic,” as they seamlessly integrate technology with “the flexibility, adaptability, and comprehensive experience of humans.”

Include stakeholders in the process

Once a company’s digital transformation is underway, this people-first mentality shouldn’t fall by the wayside. Far too often leaders pass down changes in strategies, priorities, and ways of working as a mandate. 

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Leaders tell employees there’s a new way of doing things, but managers spend less time explaining why they are making those changes. This disconnect can create confusion on a good day, and when left unchecked, this type of unclear communication can create information silos and more work about work.

To avoid this outcome, leaders must be straightforward when it comes to communicating and collaborating. “Be explicit and not implicit: in doubt, give way too much detail rather than not enough,” says Bastien Siebman, Asana Solutions Partner and co-founder and consultant at iDO.

In addition, leaders should commit to a change story to avoid this outcome and give employees visibility into the entire digital transformation process. “An increase in data-based decision making and the visible use of interactive tools can more than double the likelihood of a transformation’s success,” observes McKinsey’s report on digital transformation. Additionally, employees should be allowed to test and provide feedback on potential tools or systems before fully integrating, as this information is critical for success. 

“It’s important for leaders to bring colleagues on the digital transformation journey,” Rachel Lam, a strategist who helped transform the 135-year-old Financial Times into a digital powerhouse, tells The Workback. “Setting a vision for the organization’s future, showing employees that there is a plan to get there and that they have a part to play on that journey. Follow-up is also important—incorporating updates on digital initiatives into town halls and highlighting success. Small steps can be as powerful as larger leaps in gaining colleague buy-in.”

There’s also a business reason for this type of inclusivity. According to McKinsey, when employees generate ideas about where a digital transformation might support the business, “[organizations] are 1.4 times more likely to report success.” So, even if it’s time-consuming, leaders should always ask employees for input and take their feedback to heart. 

How to define the metrics of your success

It might seem like defining your success metrics should be the first step, but it’s hard to define success without knowing the capabilities of the team or the best ways to communicate with them. Leaders should have those two elements before determining their key performance indicators. 

Additionally, leaders should allow for flexibility, iteration, and technological advancement as time goes on. 

“Many organizations embark on transformation as a once-and-done endeavor,” says Lam. “In truth, instilling a digital mindset is an ongoing process and is never ‘done.’ It will take on different evolutions over time. Leadership that understands [this reality] and sets realistic objectives and goals is important to succeed.”

That said, there is one universal and crucial metric of success that should be evaluated by leaders and employees alike. 

In looking back at the genesis of the digital transformation, all stakeholders should ask themselves: Even if the process was difficult, was executing this digital transformation worth it?

As long as the transformation has made employees’ and customers’ lives easier, the answer is usually a “yes.”

This article includes Asana customers, partners, or employees. The Workback’s policy is to be fully transparent about the business relationships between our sources and Asana, Inc. We have identified those instances within the article as well.