There is more work getting done on more projects than you’ve ever had under your growing leadership role, but you’re feeling less success even as your responsibility expands.
You’re not alone. It’s a common experience. And here’s what’s happening…
Early in your career, success was easy to see. Your tasks often had a clear definition of “done.” And you completed work in a matter of hours or days.
As you moved into leadership, you ran projects. These could take weeks or months, but they still often had clear deliverables.
As your role grows, though, you move from project-level leadership to team- and portfolio-level responsibilities.
You’re no longer asking if the work is done, or even if you delivered the project’s outcomes. Now you’re asking if you’re investing efforts in the right outcomes.
Your feedback loop gets longer. Success is signaled by long-term sustainability and alignment with core values, guiding principles, and large-scale impact. Uncertainty in your decisions lingers while you wait for the lagging indicators to show up.
You’re not just managing work. It’s more like you’re managing bets or investments, any one of which may or may not succeed. Increasingly, it’s your job to decide where to apply limited resources.
The leaders who remain stuck are the ones who require certainty before they make a decision. The leaders who ultimately succeed recognize that some tasks or projects will fail. And some of them should. Not every project is a worthwhile long-term investment.
If you find yourself too attached to certainty to let yourself make a difficult decision, let’s talk. Visit stevedwire.com/talk to start the conversation.

