How to Build Digital Dexterity in the Workplace (+Benefits)

Imagine a workplace where every team member feels confident navigating the latest digital tools, turning routine tasks into opportunities for creativity and growth. That’s the power of a digitally dexterous workforce—beyond simply using technology to fully mastering it, driving digital adoption that enables organizations to maximize technology ROI and achieve business outcomes.

Companies are embracing modern cloud solutions and emerging technologies that streamline operations, automate tasks, and cut through inefficiencies. Research shows that organizations that invest in digital enablement and upskill training experience up to 30% productivity boosts. These numbers aren’t just impressive—they’re a call to action for anyone serious about staying ahead in a competitive landscape.

Digital transformation is more than just new software; it’s about empowering employees to harness these tools to drive meaningful change. When individuals have the right skills and support, technology becomes an ally rather than a challenge, fueling a culture of innovation and success.

Many forward-thinking organizations have discovered that the key to sustainable growth is nurturing a learning mindset. By building a foundation of digital dexterity, companies future-proof their operations and create environments where every employee can thrive and contribute to the bigger picture.

In this article, we explain digital dexterity, its tangible benefits, and the core traits that define a digitally agile team and offer practical strategies for cultivating this essential skill set within your organization.

Digital dexterity vs. digital literacy

Digital literacy is about knowing how to use digital tools, from basic software applications to navigating online resources, and is the foundation for engaging with a modern tech landscape. Digital dexterity, on the other hand, takes it a step further—it’s the skill to adapt, innovate, and leverage digital tools creatively to solve problems and drive strategic outcomes.

While digital literacy equips you with essential capabilities, digital dexterity transforms that knowledge into a competitive edge in an ever-changing work environment.

Key Traits of Digital Dexterity

Digital dexterity is a must for organizations going through digital change projects, and companies must first understand what characteristics are critical to achieving this digital skill set. Those qualities include:

• Scalability: Employees who think ahead and build solutions and processes that can scale growth are critical to developing digital dexterity.
• Flexibility: Knowing that processes can continuously be improved and new tools can drive innovation is a building block of digital dexterity in a workplace.
• Adaptability: Being open to change and willing to adapt to new processes.
• Digital champion: Is constantly looking at new ways to utilize digital tools to improve processes.
• Data-driven: Uses data to make informed decisions.
• Collaboration: The ability to work effectively in digital environments
• Digital literacy: Understanding and using data for decision-making
• Resilience: Managing change and setbacks when new technologies are introduced

Benefits of Digital Dexterity

Creating a digital dexterity workforce requires a cultural shift, but the benefits produce exponential ROI for organizations.

These benefits of improving digital dexterity in your employees include:

• Improved productivity: Digital dexterity is the foundation for adapting to new tools in the workplace. Combine this with new productivity and communication tools, and employees can work smarter, not harder, improving productivity levels, accomplishing more, and hitting goals.
• Higher efficiency: With digitally savvy employees, efficiency also improves. This means that employees are not only more productive but also complete projects faster and at a higher quality – improving employee performance.
• Scalable: Organizations with high levels of digital dexterity can solve problems and build scalable solutions powered by new technologies and software applications.
• Drives innovation: Organizations that foster a digital-first culture are more likely to develop new business innovations and growth hacks.
• High levels of digital adoption across the organization: Digital transformation projects are expensive investments, and organizations work tirelessly to drive the adoption of these digital applications and processes across their workplace. With digital dexterity employees, digital adoption initiatives come easier, with higher levels of adoption and less resistance to change.
• Stronger business resilience in uncertain markets: Organizations with digitally dexterous teams pivot faster during disruptions (such as economic downturns or supply chain crises) because employees are comfortable adopting new tools and workflows.
• Better employee experience and job satisfaction: Employees who feel confident using technology experience less frustration, making their daily work more enjoyable. This leads to higher engagement and lower turnover rates.
• Stronger customer experiences: Digitally skilled employees enable CX transformation, like resolving issues faster, enabling customers with self-service, and providing personalized experiences, leading to higher customer satisfaction and loyalty.

Challenges of Digital Dexterity

Building digital dexterity across an organization is a transformative journey, but it comes with its share of challenges.

With two out of three workers reporting they are learning, recognizing these obstacles is the first step toward addressing them, paving the way for a smoother transition to a digitally empowered workplace.

Below are some common hurdles that organizations face when striving for digital excellence.

1. Resistance to digital adoption

Employees often cling to familiar routines and traditional methods, making it hard to embrace new technologies and digital processes. This reluctance can stem from fear of change or a lack of understanding about the benefits of modern technology. When individuals resist, it hampers the overall digital transformation and slows the pace of innovation.

2. Lack of digital literacy

Without a solid foundation in digital skills, even the most advanced tools can become underutilized or misused. A gap in digital literacy can leave employees feeling overwhelmed and disconnected from the technology intended to empower them. This lack of knowledge reduces productivity, leading to team errors and frustration.

3. Inadequate leadership support

Leadership plays a critical role in championing digital initiatives, and a lack of visible, active support can derail progress. When leaders do not prioritize or understand digital dexterity, it can trickle down and create skepticism among employees about the value of these efforts. Without leadership buy-in, necessary resources and time may not be allocated to digital skill development.

4. Technology overload and tool fatigue

The rapid influx of new digital tools can overwhelm employees, leading to confusion and frustration. When organizations introduce too many platforms or tools without proper integration, it can create redundancy and diminish productivity. This overload can also result in burnout, as employees struggle to keep up with constant changes and updates.

5. Generational differences in digital skills

Different generations often have varying levels of comfort and familiarity with technology. While younger employees may quickly adapt to new digital environments, those with less exposure might find the transition challenging. These differences can create communication gaps and hinder teamwork, affecting overall productivity.

6. Limited budget and resources

Implementing digital dexterity initiatives often requires significant investment in training, technology, and support systems. When budgets are tight, providing the necessary resources for a comprehensive digital transformation becomes difficult. This limitation can result in partial implementations that fail to deliver long-term benefits.

Who Owns Digital Dexterity?

Digital transformation isn’t a specific department’s sole responsibility–nor is digital dexterity. Like any large-scale enterprise investment, improving digital dexterity requires a dedicated task force with diverse functional backgrounds and seniority levels to break down silos across the organization. Here are how different functions own digital dexterity:

• C-suite & leadership: First, you must drive change from the top. Your C-suite and leadership teams must be bought into digital dexterity and lead by example, showcasing the organization’s benefits and ROI.
• IT department: To build software requirements and roadmaps, create an implementation plan, and monitor adoption rates.
• HR/L&D: To create application onboarding, reskilling, and upskilling training content and courses for building digital dexterity skills.
• Leaders from all departments: To bring contextual digital dexterity concerns and needs from their departments and silos to the forefront of the conversation.

Take, for instance, a scenario where the c-suite members of a fictitious hotel chain decide it’s time to embark on a digital transformation journey. Immediately, the designated digital dexterity task force scans the digital landscape to identify technologies that could help them beat their competition through digital transformation in the hospitality industry.

Backed by research, they adopted an AI-powered guest services platform and prepared a comprehensive strategy to integrate this AI tool into their customer experience workflow. To ensure the IT project’s success, the task force ensures that the employees are comfortable using the new technology to delight guests and enforces management practices that shape how work gets done.

They also receive senior leadership buy-in from customer service, operations, and HR to team up with the CIO to devise digital dexterity goals. HR then hires the right talent to execute this AI project. At the same time, the existing talent (in operations and customer care) is trained to use the new technology to engage positively with the guests and improve efficiency.

Remember, every organization needs digital dexterity, but it also requires your continuous attention.

How to Build Digital Dexterity in the Workplace

Building digital dexterity is an organization’s insurance policy for achieving ROI with digital technologies. Without the skill sets to utilize software applications properly, these investments will not only fail to find ROI, but also face other severe repercussions such as dirty or inaccurate data, not meeting compliance laws, failing to meet goals, etc.

Here are some best practices for improving digital dexterity in the workplace:

1. Invest in a digital adoption strategy

One of the biggest digital transformation challenges is enabling employees with the skills they need to overcome onboarding resistance and roadblocks. Instead of looking at building digital dexterity for specific products or technologies, organizations should create a larger digital adoption strategy that provides a framework for driving adoption across the entire digital transformation lifecycle – from application research, implementation, and end-user training.

This will allow organizations to create a playbook for:

• Overcoming resistance to change
• Providing “moment-of-need” training
• Providing personalized, role-based training
• Creating training content in multiple formats
• Communicating change to employees
• Tracking user adoption and usage

2. Map your organization’s digital future and IT roadmap

Evaluate the current software market and emerging technology trends. Identify the new technologies your company intends to adopt shortly and develop an IT roadmap to maintain a competitive edge. Next, assess how these technologies and your digital strategy will affect your organization and existing processes, and determine the new skills your employees need to learn to remain relevant.

3. Understand how to engage your employees

Instead of ignoring their employees’ concerns about new digital tools and IT upgrades, business leaders need to overcommunicate and gather employee feedback.

You can identify how your employees feel about new enterprise technologies by harnessing feedback surveys and hosting focus groups or town halls. You can ask them about their technology-led concerns and what solutions would best help them attain business goals.

Once you understand their diverse needs, you can segment employees into cohorts and target them with personalized digital dexterity development programs that best suit each of these well-defined groups. You may even encourage employees to develop digital dexterity by offering incentives and bonuses linked to the progress of their company’s digital initiatives.

4. Remove barriers to digital dexterity with a digital adoption platform

Adopting and harnessing technology can be made simple with hands-on learning modules, design-forward thinking (such as empathy and customer journey maps), and A/B testing.

You can take an evolved approach to software onboarding by using a digital adoption platform (DAP) like Whatfix to enable your employees with in-app guidance and on-demand support – all in the flow of work.

With Whatfix, organizations can create in-app guided content with a no-code editor that overlays on top of any SaaS cloud, desktop, or mobile application your company uses.

Whatfix enables organizations to build digital dexterity across the workplace with:

• In-app onboarding with task lists, product tours, and interactive walkthroughs.
• Contextual help with smart tips, pop-up videos, and alert beacons.
• Self-help support with embedded wikis that pull from your knowledge base, Google Drive, Sharepoint, and other process documentation.
• User analytics that allows you to make data-driven digital adoption decisions to improve your application experiences.
• User feedback tools to prompt employees and end-users to leave feedback with real-time surveys embedded into your software applications.

5. Focus on continuous, learner-centric upskilling and training

Today, one of the biggest roadblocks to digital dexterity is the lack of skilled talent. A McKinsey Global Institute survey predicted that more than 25% of employees will need to be retrained or replaced between 2018 and 2030.

With Whatfix’s in-app guidance system, you can increase the effectiveness of your reskilling and upskilling training programs – in real time. It’s also possible to improve employees’ ability to use digital tools and lower resistance to change by making enterprise technology easy to use and available on demand.

With Whatfix’s no-code product analytics, organizations can measure training effectiveness to deliver personalized learning modules, as well as overall product and feature adoption rates. For example, IT and L&D teams can launch department or role-based onboarding flows and task lists that overlay directly inside your new software applications, track their effectiveness, monitor adoption rates, and experiment with new training content on the fly – all backed by analytics and data.

By prioritizing experience-based learning programs, you can improve employee competencies critical to digital dexterity. These include innovation programs, workflow shadowing, academic partnerships, job rotations, peer advocacy, and reverse mentoring.

By enabling technology self-service, workers can complete tasks independently without having to depend on IT or support teams. You could try Whatfix’s context-sensitive self-help widget to reduce IT help desk support tickets and receive real-time help.

6. Invest in leadership development

Apart from training your employees, it’s also important to empower business leaders and function heads to understand emerging technologies disrupting their industry. You should teach them to openly discuss digital options and choose the right tools to drive growth. They should also be agile enough to change mindsets and design new, digital-friendly workplace models by modifying existing processes and flows.

7. Promote diversity

To promote digital dexterity, it’s essential to have a workforce that has different perspectives to offer. It would also be helpful to have workers with various specialized skills ranging from technology to psychology and communication to draw on to make the digital transformation successful. Therefore, the HR leads, in partnership with the business heads, should:

• Identify skill gaps in the existing workforce by running data analytics and training competency models.
• Keep updating a dynamic list of skills required for your organization to stay digitally dexterous.
• Empower technical staff to make business decisions and employees to make technical decisions.

8. Foster a culture of change

Digitally dexterous employees are tech-savvy and thrive on risk-taking, learning, and collaboration. They adopt an iterative way of working, learn from failures, and embrace innovative and systems thinking. A digitally dexterous organization also encourages advanced data tracking and analysis to drive customization and innovation.

P&G does that with its “Decision Cockpit” initiative, which offers a centralized data and analysis repository for decision-makers across geographies. It also has conference rooms called “Business Spheres” for collaborative decision-making. To make such cultural upgrades to your workforce, you need to implement strategic changes in your organization’s processes, incentives, budgets, policies, and management.

Not sure if your employees are ready to face changes in your organization’s digital landscape? Here is a quick checklist to assess digital readiness:

• Do employees have access to real-time, contextual support to navigate new technologies? Do they have the option to learn how to use the new tool as they work on it?
• Are your core operations digitized?
• Does your company seek out new talent who has varied digital and cultural competencies?
• Are your organization’s decisions based on data and analytics?
• Does your firm encourage collaborative problem-solving and learning?
• Does your organization link employee performance metrics to the success of digital initiatives?
• Do your employees innovate and adopt new roles and work methods to support digital projects?
• Is your workforce flexible enough to participate in new technology initiatives with constantly changing requirements?
• Do you devise digital change management plans in partnership with employees?
• Are your digital transformation project timelines structured to ensure room for failing and learning from mistakes?
• If you answered ‘no’ to more than 50% of these questions, it’s time to go back to the drawing board for DD.

There is no shortcut to digital dexterity, so prepare to invest significant time and effort into making your workforce digital-ready.

How to Measure Digital Dexterity

Many organizations struggle with quantifying digital dexterity. Measuring digital dexterity goes beyond simply tracking tool adoption—it’s about understanding how effectively your employees embrace and integrate digital skills into their everyday work. Here are several ways to gauge your organization’s digital agility:

• Digital adoption rates: Track the percentage of employees actively using new software or tools. High adoption rates indicate that employees see value in these technologies and are integrating them into their workflows.
• Employee digital skills assessments: Regularly evaluate the digital skills of your team through assessments and surveys. This helps identify knowledge gaps and tailor training programs to meet real needs.
• Speed of software onboarding/training completion: Measure how quickly employees complete training programs and start using new tools proficiently. Faster onboarding can signal both effective training content and a natural affinity for digital tools.
• Digital collaboration effectiveness: Look at how actively employees engage on platforms like Slack or Microsoft Teams. Frequent interactions and a high level of collaborative activity can indicate that digital tools are well-integrated into daily processes.
• Employee engagement and satisfaction scores: Use surveys to capture feedback on how comfortable employees feel with new digital systems. High satisfaction scores often correlate with a positive digital experience, while lower scores can flag areas needing improvement.
• Time to proficiency: Track the duration it takes employees to reach a defined proficiency level with new technology. A shorter time to proficiency can indicate effective training and support systems.

These measurements provide a well-rounded view of how digital dexterity is unfolding within your organization. They help you pinpoint areas for improvement and validate that your digital initiatives are driving the intended impact.

Digital Dexterity Clicks Better With Whatfix

Digital dexterity is a game-changer for organizations ready to harness technology to empower their teams. Companies can transform how employees learn, adapt, and innovate by understanding the challenges and seizing the opportunities. A digitally skilled workforce isn’t just about adopting new tools; it’s about cultivating a culture of continuous learning and improvement.

Organizations that prioritize digital upskilling see tangible benefits—smoother transitions to new technologies, higher employee satisfaction, and stronger business resilience. The key lies in providing the right blend of training, support, and leadership that encourages everyone to embrace change.

Partnering with a trusted solution can make all the difference in this journey. Whatfix is designed to empower your organization to unlock the full potential of its digital tools. Consider these standout features:

• In-app guidance: Deliver real-time support directly within the software to help users learn as they work.
• On-demand training: Provide instant access to tailored training materials at your employees’ fingertips.
• Seamless integration: Easily integrate with your existing systems to create a unified digital adoption experience.
• Actionable analytics: Gain insights into user behavior to continuously refine training and support strategies.
• Customized onboarding: Craft personalized learning paths that address your team’s varying levels of digital literacy.

Choose Whatfix as your partner in digital transformation and empower your workforce to thrive in an ever-changing digital landscape. Request a demo today!