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Why digital strategy feels harder than it should

Published about 1 year ago • 1 min read

STRATEGY SIGNALS

BY JOSH HULST

Why digital strategy feels harder than it should

If you’ve ever tried to set a digital strategy and felt like it was harder than it should be, you’re not alone. Most leaders I work with feel this tension in three ways:

  • You’re expected to deliver, even when the future is uncertain.
  • You’re pushed to evaluate solutions before you’ve agreed on the outcomes that really matter.
  • You’re asked to create stakeholder alignment, not just outputs.

When I see this happening, I remind teams: strategy is about focus, not perfection. We start by asking questions that surface the real gaps and show where clarity is missing.

Here are a few I use most often:

  • What business result are we really aiming to achieve?
  • Where are teams aligned and where are they pulling in different directions?
  • What trade-offs are we willing to make?

These simple questions change the conversation by helping teams name outcomes and identify where to focus first. The result is a smaller set of priorities the whole team can move forward on together.

As one client told us: “Nothing in the results surprised us, since we could already feel our pain points. But it was the first time we had the clarity and structure to turn what we knew into action.”

This is digital strategy: creating shared language and the structure to act confidently.

Talk soon,

Josh

Josh Hulst: Co-founder and partner at Michigan Software Labs | 551 Settlers Dr, Suite 200, Ada, MI 49301

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Strategy Signals

Josh Hulst, Executive Technology Advisor

Strategy Signals is a monthly newsletter for leadership teams who know technology should be driving growth, but aren’t seeing it happen yet. Each issue breaks down the structural reasons progress feels slower than it should and how to change that.

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