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The Winding Road of Organizational Transformation

“What is the Roadmap to Transformation”? “How long will it take?” These are the questions that a traditional organization asks about Transformation. A “Transformed Organization” (whatever that means) would never ask that question. But we can’t get there before we’re there, so where to begin?


If I may, I’d like to hit you with a few brutal facts.


The shortest path won’t work. Why not? “Just tell us the fastest way and we’ll do it!” I get asked this all the time. The fact is, that until the organization can discover what it needs, I can’t sell it to you. Often the starting point should be “strategic clarity” or “leadership behavior” but no one EVER wants that. Why? First, because they are in too much pain, usually fighting fires. Second, because they think they have strategic clarity already, and the people looking for the solutions are not inclined to look at their own behaviors as the root cause.





Adhering to a timeline will lose you money. The corporate world is Pavlovian when it comes to timelines. Consider this, that first roadmap item is not ‘done’ but it’s been making a helluva lot of money. Finishing this item could really be a huge financial win, much more than you planned. The next roadmap item, the one we haven’t started yet, promises to make half as much. Why would be stick to the timeline? Double down on the thing that’s making a difference, and delay the next roadmap item. The same works in reverse. That first item didn’t pan out, we discovered that item #3 will actually make the biggest impact. Go ahead and jump to #3 then! Or maybe you discover that there’s something that’s not even on the roadmap that eclipses everything else. Buck the timeline, and go for it!


And if your transformation was supposed to be 3 years long, and after 3 years you are still finding ways to make huge amount of money, why stop?


Judging your transformation by a timeline is a good way to lose money. Judge it based on investment and outcome. When you start to invest more than you gain, that’s when you stop or pivot.


It has to come from an outsider. I’m not saying this just to make a plug for my consulting services, but the reason I am a consultant is that in this work it helps to be an outsider. I am pleased to see a lot of internal “Transformation Leads” cropping up in companies now.


But sometimes the hard truth just needs to come from an outsider:

To say the thing that would hurt your career if you were internal. To not have a bonus that depends on others’ perceptions. To have no bias for any internal group.

To not have a boss to block your communication.

To have no other work to take priority over the transformation.


Get an outsider’s view.


Where do we start? Start with the thing that’s causing you the most pain. The ‘nail in your hand’. Be mindful to apply first aid, and also know that it’s a band-aid. I have been accused of applying band-aids, and my answer is “The organization will die if I address root causes while they’re bleeding out. Let’s stop the bleeding first so we can see what’s blocked by pain.”


Expose the problem/opportunity. When the acute pain is stopped, that’s when you can see things more clearly. As you help in one area, other weaknesses will become exposed. For example, I often start by helping companies manage their work better; make it more visible, and prioritize clearly. That helps them reduce their cognitive load to have time to think about root causes. Then when the noise quiets down, they can see the misalignments that were underneath. Sometimes it’s culture. Sometimes it’s a lack of strategic clarity. Sometimes was just a lack of work management techniques, and there’s nothing else to do!


If we don’t know the path, how can we know how we’re doing? Right. Traditional organization question again. I can’t give you dates and ROI projections. Partially because the ROI on transformation depends somewhat on how screwed up you are now. But also because the organization won’t reap the benefits if the organization doesn’t see the problem/opportunity. No outsider can force this. This must happen internally.


Well wait, how do we know? Transformations are measurable and can use an OKR process if that gives comfort to the traditional side of the organization. In reality, each baby step ends up being so impactful that no one needs to measure it. Each step of a transformation should bring value, and if it stops bringing value, stop doing it.


Does that mean the transformation will never end? Another brutal truth here....organizations have been doing process improvement work, aka management fads; for decades. That is your ongoing transformation, it’s been renamed but it never ended. Part of a transformation is “continuous improvement”, “constant renewal”, “adaptability”. All of these imply that something is ongoing, though it may shrink, grow and change form over time.


Conclusion. A transformation is not a straight path, it follows the winding road of an organization’s evolution. All steps along the evolutionary path help the organization mature. Don’t look for efficiency in transformation, look for learning and impact. For me, the journey keeps me endlessly intrigued, and I hope the same for you!



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