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Strategy Signals

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.

Featured Post

Does your technology work for you, or against you?

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...

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...

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...

STRATEGY SIGNALS BY JOSH HULST When data is clear, but the decision still isn’t We each have access to more data today than ever before. Our dashboards are richer, our forecasting is more advanced, and AI tools are increasingly confident in the answers they produce, sometimes with more certainty than the decision itself deserves. So why is it still so hard to make decisions, even when the analysis seems to point in a clear direction? Take automation as an example. Forecasts and projections...

STRATEGY SIGNALS BY JOSH HULST Why 2025 felt turbulent for digital leaders & how to avoid repeating it Many of the leaders I met with this year were managing shifting priorities, changing budgets, and urgent requests tied to AI or modernization. Plans kept adjusting, and the expectations around digital work shifted with them. Now that we’re nearing year-end, teams are feeling stretched thin and unsure which initiatives are actually moving forward. I don’t think teams ended up here because...

STRATEGY SIGNALS BY JOSH HULST How to turn “leftover” budget into lasting value I’ve been hearing a familiar story lately, and if you’re in a planning role, you probably are too. After a year of holding back on big investments due to market and technology uncertainty, a lot of teams are finally getting the green light. Budgets that sat untouched are suddenly available, but need to be spent before the year ends. It’s a good problem to have, but it comes with its own kind of pressure. Leaders...

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,...