“Why Isn’t My Digital Transformation Making Work Easier?”

Whitney Davison
The Ready
Published in
7 min readJun 13, 2023

When new tools fail to solve old problems.

Original image: Alisha Lochtefeld

If I had a dime for every time a client told me “We have a great new tool coming soon” — (imagine any collaboration tool here) — “and once we have it? Voila! Our life’s going to change! It’ll force us to change how we work,” and then 12 months later not much of anything has evolved… well, to quote country singer Maren Morris, “I’d basically be sitting on a big ass pile of dimes.”

Digital transformation efforts are like hard seltzers at a pool party: everywhere.

According to Tech Pro Research, 70 percent of companies have a digital strategy or are working on creating one. With the allure of best-in-industry processes, an integrated tool stack, and self-service options, it’s no wonder companies are expected to increase their digital transformation investments from $1.48 trillion in 2022 to $3.3 trillion by 2025. That’s over 6% of the US GDP — a.k.a. a lot of money. And research shows the investment is paying off, with the International Data Corporation (or IDC) reporting that “digital-first” enterprises delivered eight times the revenue growth and twice the profit margin of their non-digital competitors over the last five years.

Front runners in the digital revolution have demonstrated that a company that effectively scales its transformation can achieve up to three times the cost savings over those who don’t and bring twice as many solutions to market as their competitors. Organizations that can’t? They’re among the 70 percent of digital transformations that fall short of their stated goals. Those are some high stakes at the high roller’s table.

So how does an organization ensure it’s among the few seeing the ROI on their bet?

Different Tools, Same Problems

Digital transformations and organizations fail for many of the same reasons.

Sky-high employee disengagement; leaders entrenched in ineffective legacy behaviors (think command-and-control decision-making and kingdom-building power grabs); organizational systems confined within stifling siloes.

No new flashy tool can fix those complex problems. Yet too many companies focus on a digital transformation’s technical rollout, on the change management plan of new capabilities and tools, while spending little to no time on teams defining how they want to collaborate.

Digital transformations are like statistics, relationships, or exercise: You get what you put into them. If a team couldn’t collaborate well in a previous tool stack, “lifting and shifting” them into a new one won’t unlock new ways of working. It’s not a lack of functionality that keeps teams from collaborating well; it’s that they don’t know what great collaboration actually looks like.

To realize full value transformation in our organizations, we have to change the hearts, mindsets, and behaviors of our workforce, which is something few companies know how to achieve on their own. And while having the functionality that enables new ways of collaborating is a step in the right direction, there’s more work to do to truly evolve our workplaces.

Making Tools Work For You (And Not the Other Way Around)

If you’re a leader or change agent who’s jazzed about your digital transformation but in the weeds regarding how it will impact on-the-ground collaboration, don’t panic! Now’s the time to get clear on what great teamwork looks like beyond tooling.

Here are three ways to disrupt some of the typical patterns that prevent organizations from realizing the true potential of their digital transformation efforts:

1) Focus on “how” as much as “what.”

Organizations spend copious amounts of time training users on what a new tool can do for them — but don’t protect space for teams to consider how they want to collaborate and how a new tool can help manifest those agreements. One way to do this? Encourage a team to answer this prompt: “If we collaborated perfectly, then…” Those responses can provide fodder for explicit collaboration principles the team can live into.

Some examples of principles that guide how we collaborate at The Ready:

  • We organize our teams and spaces around work, not hierarchy
  • We value asynchronous collaboration and only use meetings when asynchronous work is ineffective for a specific context
  • We default to transparency and only lock down information when psychological safety can’t thrive in an open forum or to meet organizational information security policies

Once the team identifies the truths they want to activate, they can connect the dots between those truths and the new tool. This allows a team to be more intentional and truly change their patterns around collaboration.

Pro-tip: Sometimes it’s easier to start with anti-patterns; ask a team how they don’t want to collaborate and then ask what the opposite of that would be to identify principles.

“It’s not a lack of functionality that keeps teams from collaborating well; it’s that they don’t know what great collaboration actually looks like.”

2) Use a people-positive lens when creating default tool settings.
With so many information breaches making headlines, it’s understandable why a company would want to lock down information. Setting up access defaults that require a user to justify their need for information on key stakeholder issues or project statuses is one way to reduce risk — but it comes with a price. By going this route, organizations not only increase their technical debt, but also have to allocate more management and IT staff to complete onerous administrative tasks that come with over-classification.

It also takes a cultural toll. “Need-to-know-basis” defaults can instill a culture of mistrust. In organizational systems where knowledge is power, it can deepen barriers and inequities — making it more difficult for certain people, especially those with marginalized identities, to play and succeed in the system. When unnecessary limits are placed on information, it can create an “Us vs. Them” mindset that shuts down creative spaces and stifles a group’s diverse wisdom and perspectives. By leveling the information OS playing field, we open up to the possibility of what MIT Professor Sandy Pentland calls “idea flow,” a process that builds collective intelligence from social exploration. When teams work from the same information, they build things they could never make on their own.

Instead, nudge users toward defaulting to open and clearly articulate the data security waterline of when a workspace should be private. I spent more than a decade working at the intersection of economics, finance, and public policy; I’ve seen Nudge Theory instigate huge positive behavioral changes just by tweaking a default stance. Opening collaboration spaces makes it easier for teams to work in public, share information, and see previously hidden connections in their work.

Defaulting to open also saves organizations money by reducing a network’s over-classified collaboration spaces, which come with higher administrative and cost burdens, and narrowing the focus of a cybersecurity team to a business’s most critical risks.

3) Architect your tool structure around value creation — not hierarchy.
Many collaboration tools are meant to help disperse information across an organization, so it makes sense that companies default to teaming around their current hierarchy and reporting chains; however, this enables legacy collaboration habits and keeps organizations from realizing a new tool’s full capabilities.

What’s more, it reinforces organizational silos, which are exacerbated when teams lock down their workspaces. When collaborators aren’t in the same space with the same information, work continually gets thrown over the proverbial wall (and isn’t that what you’ve already been doing?). This pattern — passing work along over and over again until something mediocre is created — wastes time and potential.

Instead, if you provision collaboration spaces around the work to be done and those who do it, you unlock containers for cross-functional collaboration few companies have ever had before. Then, you spend less time pushing information to people who need it while increasing the number of diverse perspectives (e.g., creating better products) that can be integrated earlier into processes, thus reducing rework (e.g., cost and time-to-market).

One company I worked with experimented with this move: Anyone who touched budgets across the organization could access the same space. Suddenly, they were spending less time answering questions, because they were being asked in a transparent space with all stakeholders. They also became more responsive, because everyone was empowered and knowledgeable enough to answer questions in a timely manner — no waiting on that one person who sent that one email needed.

Creating shared space for people doing similar work across the organization freed up valuable time for everyone. Just imagine what could be achieved if every team in your organization made a move like this.

Why Collaboration Is Bigger Than Just Tools

We often want our digital transformations to be one massive shift — a collective organizational “Aha!” But that rarely happens.

Mindsets and habits change when people intentionally choose new behaviors and maintain them over time. It’s the compounding of many small moves across an organization that, when added together, become greater than the sum of their parts. To start little transformation fires across an organization, leaders need to be willing to hold space and help their teams see the forest for the trees — because better collaboration is bigger than just tools.

As the old adage goes “Change is the only constant,” and how organizations engage with change is up to them. Companies in the middle of or looking toward a digital transformation have a choice: Cling to ways of working that result in greater organizational debt and bureaucracy, or rewrite the story of what great collaboration looks like in their system.

I hope you choose the rewrite option. Strengthening that muscle will serve you no matter what new crisis or shiny tool comes your way. As Maren Morris reminds us, “The house don’t fall when the bones are good.”

The Ready is a future-of-work consultancy committed to changing how the world works — from business as usual to brave new work. We help organizations remove bureaucracy and adapt to the complex world in which we live.

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Whitney Davison
The Ready

Transformer and Coach at The Ready. Recovering bureaucrat from the finance and public policy worlds.