I was leading a talk on what world-class IT looks like today in the genAI era, and studying the room of leaders. Many were looking for affirmation that their leadership approaches and priorities would make them successful in their current roles and future careers. But I was looking for the opposite signals, and seeking individuals with digital dexterity.
What is digital dexterity?
ChatGPT defines digital dexterity as a meta-skill that encompasses a blend of adaptability to new technologies, willingness to experiment and learn, collaboration across disciplines, critical thinking, and digital literacy.
We discussed digital dexterity at a recent Coffee With Digital Trailblazers. One of the speakers captured this on our collaborative whiteboard: “You evaluate digital dexterity not by looking at what leaders know, but by how they think, adapt, and respond.”
The recording and whiteboard are at the bottom of this article.
Digital dexterity in the genAI era
Is AI a skill, a tool, a capability, a risk, or an opportunity? How about all of the above?
Leaders will need to adapt, experiment, question, and reevaluate to be effective in the genAI era, or other words, they will need to exercise their digital dexterity.
According to G-P’s AI at Work 2025 Report, 74% of leaders surveyed view AI as critical to the success of their company, and 90% of HR professionals expect artificial intelligence to ramp up at their workplace this year.
Achieving business success with AI will require a combination of learning, tooling, and communication.
“Education alone isn’t the end-all-be-all — employees must also be empowered to think critically to make responsible decisions in real time,” says Laura Maffucci, VP and head of HR at G-P. “This requires leaders to clearly communicate to employees the purpose and mechanisms of AI tools, particularly how they process data.”
Let’s consider three focus areas for developing digital dexterity in the genAI era.
- How should leaders upskill themselves?
- What practice areas should leaders accelerate?
- What areas of leadership will become less important?
How should leaders upskill themselves?
Curiosity, inquisitiveness, and fealessness to question anything all came up as key leadership skills during the Coffee With Digital Trailblazers. These are a subset of the top leadership attributes of Digital Trailblazers that we brainstormed in another episode.
“The best AI leaders aren’t just tech-savvy – they’re insatiably curious and willing to fail,” says Marvin Clark, chief digital and services officer at Accruent. “Embracing continuous learning, especially across unfamiliar industries or disciplines, is how you stay sharp and spot the opportunities AI can unlock before anyone else does.”
In my recently published LinkedIn Learning course, Digital Transformation for Leaders in the genAI Era, I included videos on AI digital strategy and finding transformational use cases. Here are three recommendations on how leaders can upskill themselves in AI and develop their digital dexterity:
- Adaptability to new technologies – Use AI as a teammate and advisor by asking it questions before you figure out answers on your own.
- Willingness to experiment and learn – Encourage your direct reports to explore with tools that meet your organization’s AI governance policies. Ask them to report back on their findings.
- Collaboration across disciplines – Walk in the shoes of your customers and follow the workflows of departmental subject matter experts to find new AI opportunities.
What practice areas require acceleration?
Geoff Webb, VP of product marketing at Conga, believes AI leadership requires staying abreast of the art of the possible. Geoff suggests asking, “What can we do today to solve problems using AI, what is likely to be available in the future, and how do we plan for this future?”
Webb says leaders must communicate the strategy for AI investment to their teams clearly and effectively. “As employees see investment in AI ramping up, they inevitably become concerned that it will impact their jobs, so leaders need to be able to communicate the plan, how it will affect and enhance the day-to-day experience of their teams, and then bring those teams on board. Failure to question and communicate a strategy will result in missed opportunities to grasp the full potential of AI, either due to a lack of understanding of what’s possible or resistance from the workforce.”
When preparing the workforce for AI, two areas of digital dexterity stand out:
- Critical thinking – Asking why questions, challenging the status quo, and being able to validate an AI’s recommendations for validity and accuracy.
- Digital literacy – Amplifying data literacy skills, educating all employees with a basic understanding of statistics, establishing agile continuous planning across multidisciplinary teams, and promoting how the organization defines business value.
“Leaders must understand how to interpret and leverage data to gain a basic knowledge of machine learning and ethical AI principles,” says Paul Boynton, COO and cofounder of Company Search Incorporated. “The goal isn’t to become a data scientist, but to grasp AI’s potential and limitations to guide strategic decisions. Faster solutions with data-driven decision-making and embracing agile approaches for change management will be necessary to navigate AI-driven shifts as AI integrates across the corporate management spectrum.”
What areas of leadership will become less important because of AI?
Two experts highlighted the importance of moving away from micromanagement and command-and-control leadership practices.
“To really excel at AI leadership, we’ve got to shift from top-down directives to hands-on coaching,” says Miles Ward, CTO of SADA. The old ‘command and control’ leadership styles will become less vital as AI handles more routine decisions. Leadership is about guiding, not just directing, because the rate of change is too high to imagine that static approaches will work.”
Clark of Accruent shares what practices to emphasize to avoid micromanagement. “As AI matures, operational leadership will depend less on manual oversight and more on data quality, information interpretation, risk management, and change enablement.”
The next wave of transformational leadership can’t rely on overly specified goals and easy-to-navigate roadmaps. AI capabilities are changing too rapidly, so leaders need to plan, execute, and deliver value quickly, then look for the next opportunities. Digital dexterity is a meta-skill for the genAI era to cope with the speed and volatility of AI’s capabilities, opportunities, and risks.
Listen to Digital Dexterity
Listen to the episode of the Coffee With Digital Trailblazers.
Digital Dexterity: Upskilling the Next Wave of Transformation Leaders
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