I have been thinking a lot lately about what happens when high performers get promoted into roles that don't suit their skills. Not because they aren't smart enough or driven enough. But because the thing that made them exceptional is the exact thing that becomes a liability.
There's a metaphor I keep coming back to: plowing the field versus planning the harvest. Most leaders I know, myself included, built their careers by being the one who outworked everyone. For years, keeping your head down, working long hours and moving the business forward through sheer force of effort and output worked. That's how we got noticed. That's how we got promoted.
But you reach a point where something shifts. You land in a role where the job isn't to plow anymore. The job is to decide which fields to plant, which ones to let rest, and how to develop the people who do the work. And most companies fail to teach you how to make that transition.
The Workhorse Trap
If you've ever looked at a leadership competency model, you'll notice something interesting. The skills you need to be successful at the top look nothing like the skills that made you successful at the bottom. At the frontline level, it's about execution: moving projects forward, solving problems, and delivering results. That's level four, level three work. And the people who are exceptional at it get rewarded. They get promoted.
But by the time you reach level two or level one, the job has fundamentally changed. Now it's about vision. Strategy. Developing other leaders. Seeing around corners. Coaching people who are doing the work you used to do, instead of doing it yourself.
The problem is that nobody hands you a new toolkit when you cross that threshold. You just keep doing what made you successful, because it's what you know, and it's what feels productive. So you continue to plow the field. You work even harder. You stay later. You jump into the details because you're good at details and details feel like progress.
Meanwhile, the strategic work, the planning, the long-range thinking, the development of your people, keeps getting pushed to next week. Then next month. Then next quarter.
If you’re nodding along, you’re not alone. I know this because I've lived it.
The Hardest Part Is Stopping.
Running a boutique agency means I can fall (and do) into this trap on any given Tuesday. A client deliverable needs attention, a deck needs reworking, or a pitch needs one more pass. And I'm good at that work - I still love that work and I built this company doing that work. So the gravitational pull back toward the field is constant.
But I've learned, sometimes painfully, about opportunity cost. All those hours I spend in the weeds are hours I'm not spending on the things only I can do as CEO. Things like, building the strategic roadmap, and developing my team's leadership capabilities and thinking about where this business needs to be in two years, not two weeks.
The hard truth is that plowing feels like leadership because it's visible and tangible and exhausting. But it's not. It's labor. And there's an important difference.
Planning Isn't a Luxury. It's the Job.
What I've come to know is that the transition from execution to strategy isn't a one-time event. It's a discipline. And most organizations don't treat it that way. They promote their best executors into strategic roles and then wonder why those leaders are burned out, micromanaging, and struggling to think beyond the quarter.
The fix isn't motivation. It's not about working smarter instead of harder, which is a nice bumper sticker but not actually helpful. The fix is building the muscle for strategic thinking the same way you built the muscle for execution: intentionally, with support, and with practice.
That means carving out protected time for roadmap development. It means getting honest about what you're holding onto because it needs you versus what you're holding onto because it's comfortable. It means investing in the frameworks and outside perspectives that help you see your business the way your market sees it, not just the way it looks from inside the field.
Nurturing Your Strategic Development Muscle
This is something we work on with clients at illi. Not the coaching side of it, but the strategic roadmap side. We partner with leaders who know they need to step back from the day-to-day and build something more intentional, whether that's a brand strategy, a go-to-market plan, or a positioning framework that gives their teams a clear direction to execute against.
What we've found is that leaders don't usually lack vision. They lack the space and structure to articulate it. They don’t delegate the things they could and should. When you're head-down twelve hours a day, you don't have the bandwidth to think about which field to plant next season. You're just trying to finish the row you're on.
So if this resonates, I'd challenge you to ask yourself one question this week: how much of your time is spent in the dirt, and how much is spent planning the harvest? If the ratio is off, know most of us are right there with you.
The fields will always need plowing. But if nobody's planning the harvest, you're just moving dirt.
