The Perfectionism Tax: Why First-Time Managers Stall | L&D Guide

I'm coaching a newly promoted VP who spent three weeks perfecting a single LinkedIn post.

Fourteen drafts. Feedback from five colleagues. Still sitting in her drafts folder.

When I asked what she was afraid of, she didn't hesitate:
"People will judge me. They'll think I'm not ready."

I told her: They're already thinking that—because you haven't posted anything.

If you're an L&D leader, Chief People Officer, or anyone responsible for new manager training and first-time manager development, that story should sound familiar.

Not because your emerging leaders are agonizing over social media—but because the same pattern is quietly stalling your IC-to-manager transitions, eroding employee engagement, and creating a bottleneck in your leadership pipeline that no amount of curriculum redesign will fix.

In twenty years of revenue leadership at Google, Microsoft, and Oracle, I watched the same pattern play out across every organization.

The highest-potential individual contributors would get promoted into management—and then freeze.

Not because they lacked skill. Because they lacked permission to be imperfect.

These were people who had built their reputations on precision. The developer who shipped clean code. The seller who nailed every pitch. The analyst whose decks were bulletproof.

Then we handed them a team and said, "Now lead."

And suddenly, the very trait that made them excellent ICs—attention to detail, thoroughness, the desire to get it right—became the thing holding them back.

I call this the Perfectionism Tax: the invisible cost organizations pay when new leaders prioritize looking competent over actually learning to lead.

The tax shows up everywhere:

The result? Decisions stall. Teams disengage. And your leadership pipeline develops a silent clog that looks like cautious professionalism—but is actually fear wearing a suit.

Perfectionism isn't about quality. It's about control.

If your new managers never ship the imperfect version—the rough-draft strategy, the not-quite-right feedback conversation, the first attempt at running a team meeting—they never risk being wrong.

They never risk judgment. They never risk failing publicly.

But your organization pays the price: they also never risk succeeding.

And worse, the people reporting to them notice.

Gallup's research has consistently shown that managers account for 70% of the variance in team engagement scores. When a new manager is stuck in analysis paralysis—waiting to feel ready before making decisions, giving feedback, or setting direction—their team doesn't just lose momentum.

They lose trust.

An employee can work with a manager who's still learning. They can't work with a manager who's stalling.

Most new manager training programs focus on competency building: how to give feedback, how to run a one-on-one, how to set goals.

Those skills matter. But in my coaching work with leaders across industries, the biggest gap isn't knowledge—it's activation.

Your new managers know what a good feedback conversation looks like. They've sat through the training. They've read the frameworks.

What they haven't done is ship the first awkward, imperfect version of that conversation—and survived it.

In my Activation Methodology, I break the leadership development journey into four stages: Acknowledge, Align, Activate, and Amplify.

Most L&D programs do excellent work in the first two stages—helping new managers recognize the shift (Acknowledge) and clarify their leadership values (Align).

But the critical gap is Stage 3: Activate—actually shipping leadership behaviors before they feel natural.

Because the truth about the IC-to-manager transition that we rarely say out loud:

Your first attempt at leading should embarrass you a little.

Not because you're aiming for bad work. Because if it doesn't embarrass you, you waited too long to start.

If perfectionism is a control mechanism, the antidote isn't lower standards—it's structured permission to iterate.

Here's how I work with organizations to close the Activation Gap in their leadership pipelines:

Most manager training implicitly rewards polish. Participants present their "best" feedback conversation in a role play. They submit their "finished" development plans.

The message is clear: the goal is to demonstrate competence.

Flip the script.

Challenge new managers to bring their roughest draft—the feedback conversation they're dreading, the team meeting they don't know how to structure, the decision they've been sitting on.

Then work on it together, in real time, imperfectly.

The learning is in the iteration, not the presentation.

One framework I use in my workshops is the 48-Hour Shipping Rule: if a leadership action has been on your list for more than 48 hours, you need to ship a Version 1 or explicitly decide not to do it.

No more "I'll do it when I'm ready." There is no ready. There is only "done enough to learn from."

For L&D programs, this translates to building action sprints into your curriculum. Instead of a six-week course that ends with a capstone project, try a series of 48-hour micro-challenges:

Then debrief as a cohort—not on whether they did it "right," but on what they learned.

Perfectionism thrives in cultures where only polished outcomes get airtime.

If your senior leaders only share their wins—the finalized strategy, the successful quarter, the seamless reorg—new managers learn that messiness is something to hide.

Create space for "first attempt stories." Invite senior leaders to share the rough-draft version—the meeting that went sideways, the feedback conversation that landed poorly, the strategy that required three pivots.

When experienced leaders normalize the mess, new managers get permission to be in it.

Perfectionists often resist shipping because they don't have a clear threshold. When is a decision "ready enough" to make? When is a feedback conversation "prepared enough" to have?

Without defined criteria, the default becomes "when I feel confident"—which, for a first-time manager facing novel challenges, may be never.

I teach leaders a three-question test:

If the answers are yes, yes, and no—ship it.

This is what makes perfectionism an engagement conversation, not just a development conversation.

When new managers learn to ship imperfect work, their teams start to as well.

A manager who is comfortable iterating in public—adjusting a decision after getting new information, admitting a team meeting didn't work and trying a different format next week, openly course-correcting—creates psychological safety.

And psychological safety, as Google's Project Aristotle research confirmed, is the single strongest predictor of high-performing teams.

The leader who ships imperfect work gives their team permission to do the same.

Ideas move faster. Feedback flows more freely. People take ownership instead of waiting for instructions.

That's not just better leadership development. That's a better culture.

That VP I was coaching? She finally posted her LinkedIn piece.

Was it her best work? No.

But it was real. It got 47 comments, three direct messages, and one of those became a meaningful professional conversation she wouldn't have had if she'd waited for Version 15.

The same principle applies to your new managers.

Their first team meeting won't be great. Their first difficult conversation will probably be awkward. Their first strategy document will need a rewrite.

But Version 1 creates Version 2. And Version 2 is where the real learning starts.

Your role as an L&D leader isn't to make the IC-to-manager transition feel comfortable. It's to make it feel survivable—and then to create the systems, structures, and cultural permission that turn first attempts into real capability.

Stop perfecting your leadership programs. Start shipping leaders who are willing to be imperfect.

Real beats perfect. Every time.

For L&D Leaders and CHROs:
Book a discovery call to bring The Activation Methodology to your organization's leadership development programs.