I think we’ve all probably heard the saying “a failure to plan is a plan to fail”. Or how about, “if you aim for nothing, you will hit it every time”. And a small twist on “you miss 100% of the shots you never take” – if you don’t look and plan for the important moves, you will miss out. These are profound truths and by adhering to them, we severely limit our potential for success.


Strategy, “a plan of action or policy designed to achieve a major or overall aim” (Oxford Dictionary), is so very important for individuals, families, and more to the point for this article, businesses. To narrow my focus a little more, I will share some of my lessons learned for strategic adoption of technology, and a few thoughts on how a business might tackle this important process.


I spent the better part of 28 years in progressive leadership roles in the K12 education sector (school districts). I learned a lot about strategy, good and bad. For example, I remember a time in the 1990s when a district who I was IT manager for, was hacked (a cyber-attack before it was called that). I had not been very strategic about security and we were vulnerable. About 15 servers were compromised, full user directories downloaded and passwords presumably cracked. The compromised servers had special web serving software installed (by the hackers) and the school district inadvertently became a pornography serving service for foreign hackers. Let’s just say, I got serious about IT security. This event and lesson set us on a course to become one of the most secure school districts in the province of BC. We develop an IT security strategy with specific objectives, goals, and activities, over a specified period, and sought funding to support the plan. We successfully added and developed IT security professionals for the team, bought security equipment and software, and changed the mindset of IT and the school district forever. A strategic perspective allowed us to laser focus on the specific goals and activities required to become what we set out to be.


Fast forward to my current role as vCIO for Softlanding, I find myself fortunate to engage with a variety of clients in private, public, and non-profit sectors. In some of these engagements, I facilitate strategic planning work, specifically to link business strategy and outcomes to technological transformation and enablement. I believe that it is important to be able to engage with senior business and IT leaders to gain appropriate insight into their perspective on the challenges of today and their preferred future. An integrated perspective is important.


A few methods I like to employ to gain this insight include the uncovering of dreams (sometimes referred to destination postcards) and pain points (what is painful about the work and the technology). These two activities, provide a helpful look at where a firm would like to be and what they would like fix or change. I also use a follow-on activity to discover key (high level) use cases to clearly connect to real requirements that will make a difference. I may also lead people through a values exercise to ensure clarity on what is most important.


These activities, prior to the pandemic of 2020-2021 would be facilitated in person in conference rooms using colored sticky notes, whiteboards, among other physical tools. I have adapted the techniques to work well in a remote online meeting setting. I use a purpose designed Power Point deck with participants to collaboratively (in real time, together) brainstorm with digital sticky notes for dreams and pain points. The material that would have been on the whiteboard is on Power Point pages ready to incorporate into a strategic plan as foundational information. I also use Power Point prepared slides to capture use cases. From my education days when these activities occurred in a room, we would put the material onto chart paper on walls and after it was complete, the group would do a gallery walk to read the material, discuss and clarify it. I do the same summative activity with the Power Point deck – I present the participants work back to them as a digital gallery walk.


A side benefit of using digital tools and techniques to facilitate strategic input sessions is the first hand experience people have with such a method. This is always, in my experience, a foreign activity but people see how digital tools and techniques can be used in novel but effective ways. By the way, these techniques work in person, hybrid, and fully remote. This is helpful for my work in that the strategic plans and roadmaps are often meant to shift ways of working to maximize the benefits technology can bring.


To summarize, I believe that strategy and a resultant roadmap to implement the strategy, is essential to steering an organization in an intentional direction. With the pace of change technology is driving, such strategy needs to be broad enough to have a useful life but specific enough to effect real positive change.


Written By:

Brian Kuhn

As Softlanding’s vCIO, Brian engages with clients on strategy, the art-of-the-possible, planning, transformation, road-mapping, business case development, architecture, cloud computing, change management, technology adoption, and project leadership. Brian is passionate about being able to serve, guide, and help clients navigate ever evolving technological change and opportunity, to their business advantage.

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