How to Lead a Team When You're Secretly Winging It (And Why That's Actually Perfect)

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The best team leader I ever worked under told me she had no bloody idea what she was doing half the time. This was three months into working at a mid-sized logistics company in Brisbane, and I'd just watched her navigate a complete system meltdown with the composure of someone who'd done it a thousand times before.

"Between you and me," she said over coffee later, "I was absolutely terrified. But the team needed to see confidence, so I faked it until we figured it out together."

That conversation changed everything I thought I knew about leadership.

The Myth of the All-Knowing Leader

Here's what they don't teach you in business school: the best leaders aren't the ones who know everything. They're the ones who know how to create an environment where everyone can contribute their expertise without feeling like idiots.

I've been training workplace teams for over fifteen years now, and I've seen every type of manager imaginable. The micromanagers who think they need to have an answer for everything. The delegators who throw tasks around like confetti and disappear. The people-pleasers who can't make a decision to save their lives.

But the absolute worst? The know-it-alls who've never met a problem they couldn't solve with a three-point plan and a motivational quote.

Real leadership is messier than that. Much messier.

Why "Winging It" Is Actually Strategic

When I say "winging it," I don't mean being unprepared or careless. I mean being comfortable with uncertainty and honest about what you don't know. There's a massive difference.

The leaders who admit they're figuring things out as they go tend to build stronger teams. Why? Because they create psychological safety. When your team knows you don't have all the answers, they're more likely to speak up with their own ideas, concerns, and solutions.

I remember working with a manufacturing team in Perth where the supervisor tried to project absolute certainty about a new production process. Problem was, none of us had ever implemented anything like it before. His insistence that he "had it all sorted" meant that when things started going sideways (and they did), no one felt comfortable suggesting alternatives.

Compare that to another team where the manager started the project by saying, "Look, this is new territory for all of us. I've got some ideas, but I'm going to need everyone's input to make this work." Same type of project, completely different outcome.

The Art of Confident Uncertainty

This is where most people get confused. Being uncertain doesn't mean being wishy-washy or indecisive. It means being strategically honest about what you know and what you're still figuring out.

Here's how to do it without losing your team's confidence:

Be specific about your uncertainties. Instead of saying "I don't know," try "I'm not sure about the timeline for phase three, but I know we need to nail down the budget first." Shows you're thinking strategically, not just confused.

Share your decision-making process. Let your team see how you work through problems. "Here's what I'm considering... What am I missing?" This isn't weakness; it's collaboration.

Own your mistakes quickly. When something doesn't work out, address it head-on. I learned this the hard way after a disastrous team restructure in 2019. Trying to justify a bad decision is infinitely worse than admitting you got it wrong.

The thing about effective communication training is that it's not really about having perfect answers - it's about creating dialogue where the best ideas can emerge from anywhere.

Building Trust Through Vulnerability

I used to think vulnerability was career suicide in corporate environments. Turns out I was completely wrong about that.

The most trusted leaders I know are the ones who can say "I stuffed that up" without their authority crumbling. They're also the ones whose teams perform better under pressure because everyone feels permission to be human.

But there's a skill to it. You can't just dump all your insecurities on your team and call it authentic leadership. There's a difference between strategic vulnerability and emotional dumping.

Strategic vulnerability looks like:

• Acknowledging when you're out of your depth on technical details
• Asking for input on decisions that affect the whole team
• Admitting when your initial approach isn't working
• Being honest about external pressures without making them your team's problem

Emotional dumping looks like complaining about your workload, sharing every doubt you have, or making your team manage your stress levels.

The Power of "Let's Figure This Out Together"

The six most powerful words in team leadership? "Let's figure this out together."

Not "I'll handle it." Not "Trust me on this." Not "I've got a plan."

"Let's figure this out together."

When you say this - and mean it - you transform from being the person who has to have all the answers to being the person who helps the team find the best answers. Completely different dynamic.

I watched this play out beautifully with a customer service team in Adelaide dealing with a major system upgrade. The team leader could have pretended she understood all the technical implications (she didn't) and created a detailed implementation plan (which would have been rubbish). Instead, she brought the team together and said, "Right, we need to work out how to manage customer expectations while this system transition happens. What are the biggest pain points going to be?"

The solutions that came out of that discussion were infinitely better than anything she could have developed alone. And the team felt ownership over the process instead of resentment about changes being imposed on them.

Practical Strategies for Leading Without a Script

Start meetings with what you don't know. Instead of opening with your agenda, try "Here are the three things I'm still unclear about..." Gets everyone thinking collaboratively from the start.

Use pilot programs for everything. When you're not sure about a new approach, frame it as a trial. "Let's try this for six weeks and see how it goes." Takes the pressure off getting it perfect immediately.

Create 'learning debriefs' not just 'project debriefs.' After any significant initiative, spend time discussing what you learned about working together, not just whether you hit your targets.

Be transparent about your decision-making criteria. Help your team understand how you weigh different factors. Makes it easier for them to contribute meaningfully to decisions.

The reality is that most workplace challenges don't have obvious solutions. Market conditions change, technology evolves, customer expectations shift, and regulations get updated. The leaders who thrive in this environment aren't the ones who pretend to have everything figured out - they're the ones who build teams capable of adapting to whatever comes next.

When "Winging It" Goes Wrong

Of course, there are times when this approach backfires spectacularly. Usually when people confuse "being open about uncertainty" with "having no plan whatsoever."

I've seen managers who used "collaborative decision-making" as an excuse for complete indecision. Teams need direction, even if that direction might change as you learn more. There's a difference between saying "I'm not sure about the best approach, let's explore options" and "I have no idea what we're supposed to be doing."

The key is maintaining what I call "directional confidence" - being clear about where you're trying to go, even if you're flexible about how to get there.

Building Systems That Support Adaptive Leadership

The best teams I've worked with have created formal processes that support this kind of adaptive leadership. Things like:

• Regular 'assumption audits' where you revisit the fundamental beliefs driving your strategy
• 'Devil's advocate' rotations in meetings where someone is specifically tasked with poking holes in plans
• After-action reviews that focus on learning rather than blame
• Clear escalation paths for when experiments aren't working

These aren't revolutionary concepts, but they're rarely implemented well. Most organisations still operate on the assumption that good planning prevents problems, rather than accepting that problems are inevitable and building capacity to respond effectively.

The Counterintuitive Truth About Team Confidence

Here's something that took me years to understand: teams are more confident when their leaders are appropriately uncertain than when they're inappropriately certain.

When a leader projects false confidence about things they don't really understand, it creates anxiety in the team. Everyone can sense the disconnect, but no one feels safe addressing it directly. The result is a kind of collective cognitive dissonance that undermines performance.

But when a leader is genuinely confident about their ability to work through uncertainty - and demonstrates that confidence by involving the team in problem-solving - it creates a completely different dynamic.

The team starts to see challenges as interesting puzzles rather than threats. They develop confidence in their collective ability to handle whatever comes up. And paradoxically, this makes them much more willing to take on difficult projects and stretch goals.

What This Looks Like in Practice

Let me give you a concrete example. Last year I worked with a retail team that was struggling with a new inventory management system. The store manager's first instinct was to become the expert on the system so she could train everyone else.

Problem was, the system was genuinely complex and she was trying to learn it while managing everything else. The training sessions were disasters because she was essentially learning alongside the team but pretending she already knew everything.

When we shifted the approach to team development training that acknowledged everyone was learning together, the whole dynamic changed. Instead of waiting for the manager to explain everything, team members started experimenting, sharing discoveries, and teaching each other.

The result? They implemented the system faster and with much less stress than the other store location that stuck with the traditional "manager as expert" approach.

Why This Matters More Than Ever

The pace of change in most industries means that traditional "expertise-based" leadership is becoming obsolete. By the time you become an expert in something, it's often already changing.

The leaders who thrive in this environment are the ones who've developed what I call "learning agility" - the ability to quickly grasp new situations, identify what they need to know, and mobilise resources (including their team's knowledge) to address challenges effectively.

This isn't about abandoning planning or abdicating responsibility. It's about recognising that in a rapidly changing environment, the ability to adapt is more valuable than the ability to predict.

The most successful teams I work with now spend as much time building their capacity to respond to unexpected challenges as they do trying to prevent those challenges from occurring in the first place.

The Bottom Line

Leading a team when you're "winging it" isn't a bug in the system - it's a feature. The willingness to be honestly uncertain, to involve your team in figuring things out, and to adapt as you learn more isn't a sign of weak leadership. It's exactly what strong leadership looks like in a complex, rapidly changing world.

The best leaders I know have made peace with the fact that they'll never have all the answers. Instead, they've focused on building teams that can collectively find good answers, even to questions they've never encountered before.

And that, frankly, is a much more useful skill than pretending to know everything.

The next time you find yourself in a leadership situation where you're not entirely sure what you're doing, take a deep breath and remember: your job isn't to have all the answers. Your job is to help your team find them together.

That's not winging it. That's leadership.