An open leader’s guide to starting digital transformation conversations

Digital transformation is hard. This checklist helps make it easier.


Every company is now a technology company. We’re employing new digital technologies to gather data, to reach our customers, to manage the demands of a global marketplace, and to work more efficiently.

All this work requires some element of disruption. And quite often, disrupting our respective industries requires creating new systems and processes. If we acknowledge and accept that this is true—and that the demands of digital transformation will only continue to increase—then we also need to spend more time and energy having organizational conversations, especially in advance of major cultural and structural changes.

As I’ve said previously: While we frequently meet to discuss topics like our market needs or leveling up our innovation methods to create new solutions, we have a tendency to delay conversations about the needs of our people, cultures, and ecosystems during digital transformation efforts. But in this supposed state of continuous evolution, these conversations are imperative. So where do we begin?

I’ve developed a checklist that makes these conversations easier.

Getting started

Before we begin, let’s clear something up: Real transformation isn’t about tiny shifts. It requires bold pivots. We must recognize that sustainable change requires us to change how we think—on all fronts. Remember: Changing the way we think isn’t saying that what we think now is inherently wrong. It means admitting that we can always learn more.

The best path toward transformation is organizational openness. Organizations that embrace inclusivity allow for a constant and natural rate of evolution. This is because diverse thought—and often underrepresented voices—have more power to emerge and reveal richer sources of data from which to make decisions.

The best path toward transformation is organizational openness.

Gathering data like this—through open discourse—aids in creating places of trust, which in turn leads to less painful change. When we hold off on conversations about change because they might be very difficult, we invariably make the upcoming buy-in process and implementation equally as difficult. Ultimately, avoiding the conversation is more costly than the results of having it.

When getting started with change conversations:

The ecosystem effect

Specifically in the context of digital transformation, keep in mind that technology decisions invariably cross through and impact people, processes, and culture. Therefore, any change we make will ripple through our organizational ecosystem, so each proposed change inevitably has effects beyond our immediate and most evident problems.

In working with your teams on current and future state assessments, use the following questions to generate productive conversations.

About our current state

  • Where are we today?
  • Who are we today?
  • What is our voice saying?
  • What are we known for?
  • How are we doing things?
  • Why are we doing those things?

About our future state

  • Where do we want to go?
  • Who do we want to be?
  • What do we want our voice to say?
  • What do we want to be known for?
  • How do we want to operate?
  • Why will we do it this way?

When reviewing desired change and implementation goals, you’ll need to consider six key facets of the organization. Ask yourself (and your team): “How will this change impact our ______,” and fill in that blank with each of these terms:

  • Ecosystem (internal and external stakeholders, all actors internally, vendors, partners)
  • Culture (your mission, values, way of being, your community style)
  • Structure (the way you do work, your organizational structure, governance, how things are configured, policies)
  • Leadership and management (leadership styles, management structure, competencies and responsibilities of leaders/managers)
  • Workflows (organizational processes and trusted practices for completing work)
  • People (teams, departments, competencies)

Before you commit

You’ve met with your people. You’ve had discussions about current and future states. You’ve begun to lay out your implementation roadmap. But before you get married to your change plans, you’ll want to check yourself against open principles. Over time, this becomes second nature as part of your continual state of evolution.

As an organization leveraging openness you should always “gut check” conversations and decisions.

As an organization leveraging openness you should always “gut check” conversations and decisions with the following approach:

  • Are we creating the capacity for adaptability?
  • Are we being transparent with our need? Are we sharing information in a timely way? Are materials available for others to review?
  • Are we being collaborative in our approach?
  • Have we included all points of view and heard all voices?
  • Is our approach, and ultimately our decisions, considering the impact on our community as a whole?

Change is never easy. However, with the right mindsets, guidance, and change tools you, your people, and your organization will become stronger.

Leaders who model these behaviors consistently and provide the right training and tools to everyone in the organization can create a culture of continuous improvement—one that, when built on openness, allows for the unlocking of the intelligence of people leading to the best solutions and highest competitive advantage.


This article was originally published at; an open source knowledge community sponsored by Red Hat.


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