Three Things Not to Worry about in your Digital Transformation

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A common question for leadership is…

What keeps you up at night?

I hear it asked all the time. And the reactions run the gamut from thoughtful and deeply reflective to reactive and highly emotional. One of the common factors I nearly always hear is fear, uncertainty, and doubt. Which is why I wanted to share this article with leaders considering or engaging in a Digital Transformation.

I’ll begin with three things that are often misconstrued and cause sleeplessness on the part of many leaders. But fear not, they really don’t matter so much. Not at a high-level and not to the ultimate goals of your Digital Transformation.

But then, just when you may be feeling comfortable, in my next blog, I’ll share three things you do need to take care of. Three things if ignored, you should lose sleep over them.


Don’t Lose Sleep over These

  1. Enterprise scaling is not a problem that needs solving.
  2. Management and team resistance is not a problem to overcome.
  3. DevOps is not a tooling strategy for delivery flow.

Enterprise scaling is not a problem that needs solving.

  • Meaning, needing solving by the leadership team. This is something that should come from the bottom-up as you build capabilities across your teams and the organization.
  • Trust your teams will sort out the frameworks, toolsets, models, planes, trains, value streams, and metrics.
  • You can’t buy transformation. So, don’t try to buy it via scaling models and frameworks.
  • Besides, it’s too complex (or simple) for a top-down solution that doesn’t engage your teams.

Management and team resistance is not a problem to overcome.

  • Reframe your reactions to it. Don’t let it (and others’ reactions) trigger you.
  • Imposition doesn’t work. Instead of your normal, push-based leadership style, adopt more of a curious/pull-based style.
  • In fact, reframe how you view many things. For example, how you view resistance, measuring performance, motivating your team, inspiring your customers, etc.

Attaining Buzzwords: Digital Transformation, Agile Transformation, Business Agility, Organizational Agility, DevOps is not something to care about.

  • Apology to the Business Agility Institute 😉
  • I love Steven Denning’s point that Agile is a Mindset and the 3-things to focus on are:
    • DevOps is really not a thing, it’s a mindset around X-functional delivery
    • Do you really focus on transforming? Is that the goal? Or achieving agility? It’s like focusing on doing Scrum, or SAFe, or DevOps. They are things…
    • I would also argue that the buzzwords don’t resonate with everyone. They don’t inspire everyone. And most of the time, they get in the way.

If these are things I don’t need to focus on, worry about, or strategize for, then what do I focus on?

Ok, Bob. If I don’t have to be overly concerned about these things, what should I focus my leadership attention to? And, if they’re not going well, what should I lose sleep over?

Good question. I’ll cover that in my next post, so you can get some great sleep until then. Stay tuned.


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