How Leading Digital Trailblazers are Pragmatic Vision Painters

Digital transformation leaders – people I call Digital Trailblazers – wear many hats, and one that’s come up several times during our Coffee with Digital Trailblazers is the role of vision painter. As a vision painter, we must understand business strategies, learn market needs, capture customer feedback, and identify technology opportunities. Our objectives include painting a future vision, and sometimes tailored ones for different stakeholders, to guide our organization on opportunities worth pursuing and learn their customer impacts.

Digital Trailblazers as Vision Painters

The vision painter leadership attribute came up during our discussion of the top competencies of Digital Trailblazers. We collected fifty of them, and I have a survey running to capture everyone’s votes on the top ones.

Tyler Johnson, CTO of PrivOps, listed vision painter as his top leadership attribute, and you can watch his Driving Digital Standup video,  an entrepreneur and architect’s view on the right people to Lead digital transformation initiatives.

Joanne Friedman also voted for vision painter but with some added content. She says, “A pragmatic visionary or a Visioneer is someone who imagines their future state. All transformation is a future state. Visioneering helps define what outcomes you want to achieve as a digital business.”

You can watch Joanne’s interview on the Driving Digital Standup, a pragmatic visioneer and design thinker’s view on the right people to lead digital transformation, where she shares her other top attributes of Digital Trailblazers.

What is a pragmatic vision painter?

Think of vision painting as an early sketch of the future that a Digital Trailblazer can share with customers, colleagues, and stakeholders. We use it to get quick, directional feedback and seek an “eyes lighting up” moment when our painting resonates with our audience. Visions painted with a wireframe, diagram, or other sketch can be very powerful, but Digital Trailblazers can also tell a short story or verbally describe their visions.

StarCIO Vision Statement Template

The vision may have different versions for different audiences, and the Digital Trailblazer should iteratively improve their vision based on feedback. Paint visions before drafting a vision statement – a step that Digital Trailblazers should do collaboratively with selected transformation initiative leaders and stakeholders.

What to include in your vision painting?

You can’t overload this painting with too much detail or create an abstraction that’s too hard for people to understand. Below are my recommendations:

  • Understand the viewer’s context – What’s happening in your industry and business and the lens of the stakeholder who will critique your painting. This context is important because the transformation visions we’re painting serve the purpose of getting feedback.  
  • Focus on an achievable future state and target a reasonable timeframe – Stakeholders don’t want science fiction from Digital Trailblazers. If you need to share a longer-term vision for a large strategic transformation, follow up with a second one that covers a shorter timeframe.
  • Include customer personas and segments on the canvas – These are your painting’s subjects. What’s different for them in your future vision, how does it benefit them, and why should customers care?
  • Create a sense of urgency – The vision painter must depict an opportunity or threat impacting the business concerning the subjects. Without this urgency, the painting may come across as a pretty picture without a calling that motivates the audience.
  • Avoid the solution and implementation details – These details create the wrong focus if the audience doesn’t understand or buy into the opportunity and problem statement. Worse, it can create detractors if the audience sees other paths to pursue the opportunity.

Vision painter: An illustrative example

For most of us, we’ll paint our vision verbally and hope our words conjure a picture in our audience’s mind. To share an example, here’s how I paint the vision of StarCIO’s programs for Digital Trailblazers:

You are a technical lead and elect to partner with a product manager on a digital transformation initiative you believe will grow sales, improve customer experience, and deliver workflow efficiencies. You see yourself driving a boat through choppy river waters, pursued by competitors in a race to be first to market with this capability. On one side of the river are several executives warning you about the dangerous rapids – costs, security, and other risks – and demanding you come onshore. On the other are your colleagues and teammates, all working on different projects and making limited progress. The river splits upstream with one side, leading to even choppier waters. But the other side looks calmer, and you see another vessel upstream. The name on the boat is Digital Trailblazer Advisory, and you can see the words agile, product management, and DevOps painted on its hull. Out on the horizon, you see your teams working collaboratively, and your primary stakeholders are celebrating.

In a real-world setting, I personalize this story to the initiative’s objectives, the competitive factors, and very few details about our digital transformation core competencies.

I love painting visions and guiding my clients to their realities. Reach out to me, as I’d love to be your guide. 

Isaac Sacolick
Join us for a future session of Coffee with Digital Trailblazers, where we discuss topics for aspiring transformation leaders. If you enjoy my thought leadership, please sign up for the Driving Digital Newsletter and read all about my transformation stories in Digital Trailblazer.

Coffee with Digital Trailblazers hosted by Isaac Sacolick Digital Trailblazers!  Join us Fridays at 11am ET for a live audio discussion on digital transformation topics:  innovation, product management, agile, DevOps, data governance, and more!

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.