profile

Strategy Signals

Why digital strategy feels harder than it should

Published 8 months 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

These signals are meant to be shared. If you know someone who’d benefit, invite them to subscribe here.

You can unsubscribe here. To change your email or preferences manage your profile.

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.

Read more from Strategy Signals

STRATEGY SIGNALS By Josh Hulst, Michigan Software Labs Does your technology work for you, or against you? If you ask most leadership teams to describe their technology, they'll walk you through a list of tools, such as the CRM they implemented three years ago or an ERP that they inherited from an acquisition. It might be an accurate list, but it's not really the answer I'm looking for. Knowing which tools you have is not the same as knowing what they can support together. For instance, can...

25 days ago • 2 min read

STRATEGY SIGNALS BY JOSH HULST You’re asking the wrong question about AI You're getting this from a new email address. Nothing has changed except where it comes from. What should we do with AI? It sounds like a responsible starting point. It feels like you're taking the technology seriously by exploring your options. But in my experience, this question produces a specific kind of response: searching for tools, a pilot or two, or a list of pain points to automate. The issue is that this...

about 2 months ago • 2 min read
two men look at a tablet screen

STRATEGY SIGNALS BY JOSH HULST Are you feeling the pressure to “do something” with AI? Are you “doing something” with AI? Most leaders I’m talking to can point to visible AI activity inside their organizations, whether that’s a pilot underway or teams wiring small automations into their daily work. In many cases, people genuinely are feeling more efficient! So why does it still feel unclear whether anything meaningful has changed for the business? One reason is that AI has become unusually...

3 months ago • 2 min read