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Chapter 3 | Digital Fluency Guidebook

Creating Your Digital Fluency Roadmap

No matter where you are on the journey towards digital fluency, it can be helpful to orient yourself to the path ahead. To help with that, here are reflection/discussion prompts and downloadable worksheets to support you in scanning the territory of digital fluency so that you can keep yourself on track, and optionally share with your team or thought partners.

Start with thinking.

Thinking: The Need For Unlearning

Think about your current landscape. Look for areas where old mental models are no longer viable.

What’s a familiar business habit or practice that no longer seems to be working?

How is the landscape changing in your industry? Where are areas where you need new mental models?

Where are there competing objectives (eg. Global vs. Local)?

Try imagining what digital fluency would look like for you or your team.

What would digital fluency look like for you or your team? How might you respond to specific situations or opportunities? For example, “Digital fluency would look like knowing technical feasibility when clients ask for new features.”

Write a 'user story’ with the following ad lib: Digital Fluency would look like [response] to [situation/opportunity].

For example, “Digital fluency would look like knowing technical feasibility when clients ask for new features.”

Scan the 'territory' of digital.

Are there terms that everyone else seems to know the meaning of, but you (or your team) aren’t clear on?

Are there terms that are being invoked to make decisions that people don't really understand? (eg agile)

Are there trends you would like to understand more deeply?

Are there ‘digital’ threats or opportunities you are trying to prepare for?

Focus on direction before destination.


General, thematic: often about capabilities and occurs when you don't know the terrain or have a map


Very specific: outputs and outcomes, premised on knowing and trusting your map and capabilities


General, thematic: often about capabilities and occurs when you don't know the terrain or have a map


Very specific: outputs and outcomes, premised on knowing and trusting your map and capabilities

Focus on direction before destination.

Shame and embarrassment don't help anyone raise digital fluency.

The journey to digital fluency sometimes starts when we realize we've said something about technology exposing our ignorance or an obsolete model of thinking. Maybe it even felt like our sense of worth was called into question. Even if a moment like that motivated you to raise your fluency, it's not a useful tactic to keep yourself motivated or get others to embark on their own journeys. When we're experiencing a world changing faster than ever before, people become overwhelmed and sometimes have a fear of becoming irrelevant or obsolete. This is in part because they think of learning, an additive process, and don't know or remember to unlearn, which is letting go of unhelpful ways of thinking and working. While there is no doubt that digital fluency is required for the jobs of today and tomorrow, it is important to create what is increasingly known as "psychological safety." As a leader or peer, find a place for yourself and others to express curiosity and ask questions (dumb or not) without risking jobs or reputation too much. If you don't find a way to model curiosity (and professional vulnerability), others won't either. You can also risk showing up as inflexible or unadaptable. One first step might be to share a working digital fluency roadmap with your colleagues and ask for input or what they are learning (and unlearning) in those areas.

“If we want people to fully show up, to bring their whole selves including their unarmored, whole hearts—so that we can innovate, solve problems, and serve people—we have to be vigilant about creating a culture in which people feel safe, seen, heard, and respected.”
— Brené Brown, Dare to Lead: Brave Work. Tough Conversations. Whole Hearts.

Who is in your network for digital fluency?

A network of 'digital' thinkers and doers can partner with you to update your own thinking, brainstorm and execute on new ideas.

Who are champions in your network (leaders who bring resources and remit)?

Who are explorers in your network (individuals who discover new opportunities)?

Who are makers in your network (individuals who have the technical know-how to make digital prototypes or assemble digital solutions)?

Data Opportunities

Data is one of the most vital—and complex—components of a digital world. It can help to put in human terms what you wish to understand about data gather and analyzed with machines.

What data do you have now? What data would you like to have?

What questions would you like to be able to ask of data if it were a person? What decisions might you like to make based on data?

How might you use data-derived insights to enrich your current business?

What new opportunities or paradigms might data enable for you?

Business Model

Think about your current business models and how they might change as digital fluency and capabilities increase.

Things (assets): What are our assets and how will we best protect and leverage them?

People (services): How will we engage the best talent and deliver the best experiences?

Ideas (intellectual property and technologies): How will we create and share intellectual property? How do we design and build exponential value with machines and data?

Connections (networks): How will we enable and amplify the exchange of value between parties?

Tools and Technologies

Think about your digital fluency with technologies and tools. You might start by looking for more information on common technical jargon, but it might be helpful to look at the bigger picture.

Are there tools or technologies you'd like to be using but which you don't currently think you're using right or to their fullest potential?

Are there opportunities for tools that would support new ways of working with your teams, partners, and clients, such as digital whiteboarding software or chat systems?

Are there technical decisions (like feature prioritization and roadmaps) you would like to be more aware of or involved in?


Which skills would you like your team to add or improve?

First, organize these skills by Technical skills, Intellectual skills, and People skills.

Second, rank them by priority.


  • Set a direction for your digital fluency journey, even if you don't know the exact destination yet.
  • Start with upgrading your thinking—scan the environment around you, identify areas of 'unlearning,' and develop a network of contacts who can help.
  • Begin making a list of opportunities for raising digital fluency in each pillar—thinking, data, business model, tools and skills.
  • Make your plan visible and editable—try sharing a document you can edit with others using Google Drive or Office365. If you'd like to be a bit more adventurous, you can use, a great visual whiteboarding tool.
  • Create a regular practice of unlearning and learning, ideally in partnership with others.

Did this guidebook get you thinking? Let's talk about how to bring new mental models into your organization for exponential results.

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Read the other Guidebooks in the Digital Fluency: Thinking series

Thinking For A Digital Era

Transform your mindsets for the digital era.
Read the Guidebook

Thinking Styles

Discover the power of diverse thinking.
Read the Guidebook

Rethinking Remote

We have to shift our thinking for remote work, not just our locations.
Read the Guidebook