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Ask most leaders what kind of culture they're building and you'll hear "flexible" and "autonomous" - code for wanting the work done without having to micromanage anyone.
What many in leadership positions inevitably realize is flexibility alone doesn't work. Without structure, freedom just stalls projects. Rely on everyone's innate intrapreneur skills and you discover very few, through no fault of their own, possess them. A 2025 Gallup article put it plainly: "Many employees learned the value of increased autonomy during the pandemic, but it only works if expectations and accountability are clear."
The instinct itself is a good one. Most leaders, having survived their share of horrible bosses, want to build something more human and less micromanaged. But there's a trap in that ambition: too much flexibility and independence sets a low bar if it isn't paired with strong accountability. Leaders allow everyone to design their own schedule, then watch deadlines slip and projects stall. Accountability has to come before flexibility, not after.
What follows are some lessons about how flexibility, understanding, and accountability work with - and against - each other.
Spell It Out
It doesn't make someone weak if they need specific directives. Everyone has different skillsets, different brains, and different methodologies. Not everyone possesses a self-directed, entrepreneurial brain, despite the push these days to cultivate the intrapreneur. There will always be people who need specific direction and those who don't, and neither is better than the other.
Putting disparate work styles aside, people still need to know what’s expected of them.
Gallup research found that only about half of all workers strongly agree they know what’s expected of them at work. Their research indicates that setting clear expectations might be the single most foundational element of employee engagement. If only half of all workers can confidently say they're clear on what's expected of them, we can assume that a leader who thinks their team is on the same page is statistically wrong about that half the time.
If you’re leading people, have an initial conversation to uncover what kind of work style your people have (particularly in remote working situations) and what they expect from their leader. Maybe run an assessment so there's a glimpse into their personality. What leaders want to avoid is the loop where they hand back work saying this isn't what I wanted, the employee insists they never heard that, and the leader chalks it up to something that should have been a given.
Was it a given? Or is the leader expecting employees to think exactly like they do? Even employees with the intrapreneurial gene won't fill in every blank required to carry the business forward. Awareness of one's own expectations - and of the gap between those expectations and what's actually been communicated - is the prerequisite to everything else.
Look In The Mirror
When it comes to engagement and expectations, the Gallup research is clear: “Managers account for at least 70% of the variance in employee engagement scores across business units.” Meaning, if a team is disengaged or lacking direction, it’s rarely the team’s fault but rather the person leading it.
Leaders should ask themselves some hard questions. Are they avoiding directness because they want people to like them? Are they, on some level, afraid to actually manage? Are they expecting everyone to operate like an entrepreneur, when most people simply don't? And the uncomfortable one: do they actually know what they want, or were they quietly hoping their employees would figure it out for them?
Because here’s how that scenario usually plays out: employees don’t figure it out, the leader realizes the onus was theirs all along, and now there’s one more thing on the to-do list. This when self-loathing and resentment starts to build. It’s a familiar spiral. The good news is it’s fixable.
Flexibility Is Earned
Start implementing continuous feedback and accountability. Create deadlines and don't let people off the hook. A lot of pressure rests on the boss - and the company - to build the perfect workplace culture, but it's a two-way street: employees are also responsible for earning flexibility and understanding. This is especially hard in remote situations, but it should become a mantra that accountability comes before flexibility.
If people don't do what they said they would, then their flexibility should be reevaluated. Letting it slide costs more than most leaders realize.
The cultures that get this balance right aren't the ones with the best perks - they're the ones with the clearest standards. Unlimited vacation, flexible hours, and remote-first policies only work when there are real consequences behind them.
The high road is simple: meet the bar and the flexibility is yours.
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