Experience: Asset or Liability?

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Picture this: five years ago, you were at the helm of a tight-knit engineering firm with about 70 people across three departments, all serving the same production workshop. You had a handful of trusted managers whose coordination was based on a lot of 1-on-1s. Fast-forward to today: you’re the Managing Director of a 300-strong company with 18 managers under you, and it feels like chaos on tap. The business has been flourishing, but your managers are disgruntled and continuously complain about the situation at hand which feels chaotic. 

That’s the story of Carl, who rode a wave of rapid growth with pride until one day when he realized his old playbook wasn’t working anymore. When the team was small, he could pop into any room or in the workshop, nip issues in the bud, and keep everyone marching in step. Now, with nearly four times the people and more handoffs than he can count, Carl’s once-reliable routines have become a tangle of missed signals and costly overlaps, even though he praises himself for having a flat organisation. 

The structure is not working anymore. His trusted habits - weekly all-hands, detailed email digests, and one-on-ones with each manager - used to work like clockwork. Now they’re just noise: emails go unread, meetings stretch endlessly, and pockets of misalignment fester out of sight. It feels like there is no accountability anymore. That go-to management style? It’s become a liability hiding in plain sight.

Here’s the question we’ll tackle: when does “been there, done that” stop giving you an edge and start holding you back? In this newsletter, we’ll dig into why our proven methods can start to trip us up, and, crucially, how to recognize when it’s time to evolve your approach before the next growth spurt derails your momentum. Ready to give your playbook a reality check? 

The Comfort-Zone Trap

Remember those early days when Carl could pop into any workshop and smooth out a hiccup in minutes? That hands-on approach was dependable: he saw a problem, swooped in with advice, and voilà, crisis averted. It felt smart, efficient, and downright heroic.

There is a catch, though: with 18 managers and continuously moving and debated responsibility boundaries, that instinct to “just jump in” becomes the very thing that blinded Carl.

Your brain craves familiar patterns, and before long you default to your old comfort zone:

• Routine check-ins become status updates rather than problem-solving or strategy sessions.
• One-on-ones feel like déjà vu, so you cover the same ground and invite for quick fixes instead of digging into the new challenges with an organizational broad or systemic approach.
• Email digests pile up in inboxes, unread and unloved because they’re more noise than insight.

Imagine your comfort zone as a well-worn trail in the woods: easy to follow, but bordered by thick undergrowth you never explore. When growth pushes you off that trail, you stumble—because you never mapped the new terrain. Carl’s old playbook worked beautifully…until it didn’t. Next up, we’ll explore how those trusted routines morph into rigid mental models—and why breaking them is the key to thriving amid complexity.

Mental Models vs. Mental Shackles

By now you’ve seen how comfort-zone routines can trip you up. Now let’s continue into the heart of the matter: mental models. These are the internal maps you build from years of experience, solid frameworks that help you make sense of complexity in a flash. Carl had plenty of them:

“The best way to manage an organisation is through a flat management structure.” (that means all 18 managers reporting directly to him).

“If Project A misses its revenue margin, then Project B will compensate,” or 

“We need to remain efficient, therefore rapid solutions are the best.”

“Weekly all-hands solves cross-team misfires.” 

Those assumptions kept things humming…until they didn’t.The upside:

• Speed & Certainty. When you face a familiar scenario, you leap to a solution without overthinking.
• Efficiency. You conserve brainpower, focusing energy on new or thorny problems.
• Consistency. Teams know what to expect, so execution stays tight.

The downside—when mental models harden into shackles:

• Blind spots emerge. You filter out data that doesn’t fit your model. Carl missed how complex the production planning became with now 3 different workshops running because his assumption remained unchanged and unchecked about how capacity planning was done, completely unaware of the interdepartmental interaction and coordination needed. He saw an increased level of conflict at the middle management level but interpreted it as a sign of passion for their work.
• Rigidity reigns. You cling to “what always works,” even when context has changed. Requests to tweak the way we are doing things here met firm, sometimes even impolite, “no,” because that’s not how “we do it.
• Innovation stalls. Fresh ideas about organizational changes required feel risky, so they’re quietly discarded before they can gain traction. Carl refused many times throughout the past 5 years to introduce any change in the organisational structure and work new responsibilities and authorities accordingly. Managers, although very frustrated, stopped bringing him more claims in this respect.
• Decisional bottlenecks occur - Carl started to find himself in a decisional whirlpool, with more managers searching him for final approval or using him as a mediator for the ever-growing number of cross-boundary situations needing a resolution.

Here’s a quick test: pick one of your go-to assumptions - maybe it’s: “More meetings equal better alignment,” or “The more pressing the issue, the more invested and proactive everyone gets.” or “People show passion when are noisy, pushy or even aggressive.”

Now ask yourself: is that still true today? Could it be masking a new risk or silencing a bright idea? Carl’s breakthrough came when he realized his mental models for a 70-person firm weren’t scaling to 300. He had to surface his hidden assumptions, challenge each one, and rebuild a toolkit that fits today’s complexity. 

Up next, we’ll look at concrete signs your experience has shifted from asset to liability—and how to catch them early before they cost you big. Ready to spot those mental shackles? Let’s go.

When Experience Becomes a Liability

At first, your track record feels like a safety net. But keep repeating the same old moves, and that safety net can start to squeeze you. Experience becomes a liability when it subtly shifts your focus from discovery to defence—when you’re more invested in protecting “what worked” than uncovering what could work better.

Watch for these red flags:

• Automatic shutdown. You catch yourself dismissing new proposals with a quick “We’ve tried that,” without exploring what’s changed since.
• Overconfidence bias. You assume you’ve seen every twist before, so you underprepare for novel challenges.
• Echo chambers. You surround yourself with “yes” people who reinforce your old playbook instead of testing it.
• Invisible gaps. Teams report all metrics green, but somewhere, pain is building because your dashboard still mirrors an old structure or an old way of doing things.
• Too much defense. You find yourself defending again and again a way of doing things although everything around screams change is needed.

How about Carl? His weekly all-hands showed on-time delivery at 98%, so he assumed a smooth cross-workshop flow. Yet customer quality complaints were spiking, an early warning he’d ignored because his metrics “said everything was fine”. That misplaced trust in familiar data cost him the trust and loss of several clients.

Remember: your experience should light the path forward, not cast shadows over new terrain. In the next section, we’ll explore practical habits to reboot your mindset so your hard-earned expertise stays an engine for growth, not a brake on your ambition.

Rebooting the Manager’s Mindset

Growth shows us where our old tricks stop working—and that’s good news: it means you know exactly what needs updating. Let’s turn those worn-out routines into flexible habits that scale with your team, rather than buckle under its weight.

Audit Your Assumptions

• What to do: List your top three “always-true” rules (e.g., “Weekly 1-on-1discussions fix misalignment”).
• Why it helps: Exposing hidden beliefs makes room for smarter choices.
• Quick exercise: On a blank page, write each rule and challenge it with “What if…?” (What if we met fortnightly? What if instead of 1-on-1 you met the entire team and discussed collectively? What if teams rotated facilitators?). 

Invite Beginner’s Eyes

• What to do: Pair veteran managers with newer colleagues for one month—let juniors ask questions and spot oddities.
• Why it helps: Fresh perspectives reveal blind spots no veteran notices.
• Quick exercise: Host a weekly “Curiosity Coffee” where a manager interviews a different team member—no agenda, just questions. 

Mix Up Your Squad

• What to do: Run a quarterly cross-functional workshop on a real challenge including production, sales, operations, accounting, and even HR.
• Why it helps: New voices generate new ideas and bust silos.
• Quick exercise: In a 30-minute “Idea Jam,” present one challenge then let everyone throw out one wild solution—no filters allowed, all ideas are valuable.

Run Small Experiments

• What to do: Choose one new practice (e.g., daily 10-minute stand-ups, rotating meeting leads) and pilot it with two teams for four weeks. What value could you draw? What did you learn?
• Why it helps: Low-risk trials show what sticks before you overhaul the whole system.
• Quick exercise: After the pilot, send a one-question survey: “How did this change help—or hinder—your work?” Ask yourself this question. 

Build a Reflection Habit

• What to do: Reserve 15 minutes at week’s end for a “manager’s journal.”
• Why it helps: Regular reflection keeps you tuned to subtle shifts.
• Quick exercise: Answer three prompts: What surprised me this week? Which assumption did I lean on most? What should I question next?
  
  

With these steps, your “management playbook” becomes a living toolkit, one that grows stronger as your company expands, rather than cracking under the strain. 

Your Next Steps

You’ve spotted the cracks and tried on fresh habits, now let’s lock in that momentum. Here’s your three-step action plan to keep experience working for you, not against you:

Mindset Tweak

• Action: Swap one “automatic no” for a “tell me more.”
• How: Next time you’re about to dismiss an idea—pause and ask a clarifying question instead.
• Outcome: You complete even better the bigger picture and it opens the door to possibilities you might’ve shut out.

Team Ritual

• Action: Launch a fortnightly “Fresh Eyes Forum.”
• How: Invite one or two non-core stakeholders (new hires, adjacent teams, even a customer rep) to your problem-solving huddle.
• Outcome: Injects unexpected insights and keeps the team on its toes.

Reflection Prompt

• Action: End each week by asking, “What surprised me—and what did I learn?”
• How: Block 10 minutes on Friday afternoons for quick notes in your journal.
• Outcome: Builds self-awareness and primes you for continual growth.

Remember, Carl’s flat structure felt like freedom until it turned into a familiar chaos. His prior experience - significant and valuable in one context, turned into a series of unchecked assumptions and beliefs that made him act in a way that was not appropriate nor supportive of the complexity his organization reached. Experience is there to inform; it is the fuel to power your next leap.

However when the context changes, your prior experience should be kept in check because it can negatively interfere with your current actions. Keep asking questions, run those small experiments, and stay curious. That way, when your company doubles again, you’ll be ready—playbook in hand, mind open, and momentum unstoppable. Working with a coach can supercharge this whole process.

A skilled coach will help you shine a spotlight on those hidden assumptions you uncovered in your audit, asking the tough “what if” questions and holding up a mirror to any blind spots. They can also act as that “beginner’s eyes” partner, probing your routines and suggesting fresh experiments you might never have tried on your own. By guiding your small pilots, a coach ensures you’re learning fast, iterating wisely, and capturing the real impact of each change. Even more importantly, a coach keeps you honest and focused.

When your “automatic no reflexes” creep in, they’ll remind you to swap it for a “tell me more.” They’ll help structure your "fresh eyes forums" and drive that weekly reflection habit, making sure each insight sticks. In essence, having a coach by your side means you’re not just trying new management moves, you’re embedding them into your leadership muscle memory, so your experience remains a springboard for growth rather than a brake on your next big leap.

 

Book your discovery call. No pressure, just a conversation around your experience and how you apply it with a beginner's eye. You bring the mindset. I’ll bring the mirror.

Share this article with a colleague who values growth. Remember, in management, strong and knowledgeable allies matter. If this resonates with you, you're already inviting powerful transformation into your leadership. I'm here to support your journey to mastery.

Until next time, keep thriving! 

Alina Florea

Your Management Performance Coach 

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