Winging It Is Not a Strategy: What to Do When the Plan Falls Apart

We’ve all been there. A big project launches with lots of energy, good intentions, and a vague idea of how it’s all going to work. A few weeks in, and things start to wobble. Timelines blur. Roles aren’t clear. Morale dips. And suddenly, you’re in reactive mode, asking the question no leader ever wants to say out loud:

“What the hell is happening? Why aren't we on track?”

Here’s the truth: winging it is common, but it’s not sustainable. Especially for leaders in social impact work, people operations, and mission-driven orgs—where the stakes are high and the teams are stretched.

The good news? You don’t need a full re-org to get back on track. You need a pause, a reset, and a process that makes space for both clarity and action.

Why Winging It Happens

• Lack of clear direction (vision without structure)

• The speed of execution overtakes intention

• Everyone’s trying to be "flexible"—but it leads to chaos

• Avoidance of tough conversations about what's actually not working

Winging it usually starts as good energy: "We'll figure it out as we go." But when "figuring it out" turns into firefighting every day, it’s time to reframe.

3 Questions to Reset Your Strategy in Real Time

1. What’s working (that we can double down on)? Start with strengths. Identify what's flowing well, even if it’s small. Use that as your foothold.

2. What’s stuck or unclear? Look for friction points. Where are things getting lost in translation? Where’s the confusion or overwhelm?

3. What do we actually need right now? This is the big one. Don’t reach for the ideal version of your org—reach for what would help your team this week. Clarity? A simple checklist? One person making a final call?

A Mini-Framework: The Plan Behind the Plan

When you’re in the thick of it, don’t try to solve everything at once. Try this:

• Principles: What do we stand for? (This informs all decisions.)

• Priorities: What matters most this week/month?

• People: Who’s responsible for what—and do they know it?

This isn’t fancy. It’s not meant to live in a slide deck. It’s meant to get your team breathing again and moving with intention.

The Bottom Line: Winging it is a sign of momentum without structure. If you’ve hit that wall, don’t panic. Pause. Ask better questions. Make a simple, clear plan that meets your team where they are.

You don’t need perfection. You need direction.

Feeling like your team is stuck in reaction mode? I help leaders make real-time resets that actually stick. Reach out to gebomaco@gmail.com or DM me on Instagram @thegenevievemartin to start untangling the chaos.

And hey—if this hit home, share it with someone who needs the reminder: winging it is not a long-term strategy.