Experienced Leaders Fail When They Skip This One Step

Ron Johnson. That name should be etched in everyone's brains as someone who shows us exactly what not to do in a new leadership position. Exceedingly smart, spectacularly successful. Epic failure. 

He was the former SVP of Retail Operations at Apple, credited for developing the Apple Store and the Genius Bar. He worked directly with Steve Jobs and helped drive Apple's stock 15x during his tenure. Before that, he was VP of Merchandising at Target, contributing to a 12x increase in their stock. Amazing, right? In 2011, JCPenny brought him on as CEO.

A year later, the changes he made resulted in $1B in losses and a 66% decline in stock value. 

This case is studied in business schools around the world. And a version of it plays out every single day in startups and scale-ups everywhere. 

Here's a more relatable version of Ron - A VP of Marketing joins a Series B SaaS company. Impressive resume. Big name logos. The CEO is fired up. The board can't stop talking about them. A press release goes out. The website gets updated. So much pride in landing someone this accomplished. 

Shortly after they begin, there's a flurry of activity. Team meetings, cross-functional strategy sessions, big plans. And then the events start. Spectacular events. The kind people rave about. Attendance numbers climb. Social media shares fly. Press mentions roll in. The new VP is beaming. 

But MQLs? No noticeable bump. Accelerating sales opportunities? Can't even measure it. Marketing budget? Dwindling fast. ROI? Forget about it. Revenue-growth? What even is that?

And the people closest to the work, the ones with practical knowledge, the ones who actually know the buyers, start to feel it. Something's off. But the halo around this new leader is blinding. The institutional confidence in their pedigree is so loud it drowns out the people who actually know. So doubt gets swallowed. Instincts get buried. And the misalignment keeps running. 

90 days pass. Then another quarter. Targets missed. Leadership says give it time. But things aren't getting better, they're getting worse. And eventually, after enough damage is done, the leader self-implodes or gets ousted. Usually both. 

What happened? What did Ron do? What did this VP do? Why did they fail?

Because of something I call the "Copy/Paste Leader"

The leader who has done great work before, delivered real results elsewhere, comes into a new company, and copy/pastes what they've done. Same projects. Same initiatives. Same campaigns, tools, approach, tech stack. They bring real credentials and real wins, then paste them into a context those wins were never designed for. They repeated the content without assessing the context. 

That's exactly what Ron Johnson did at JC Penny. He took what worked at Apple and pasted it in. No more discounts. Everyday low pricing. Minimalist store layouts. 

If you've ever shopped at JC Penny - and I certainly did as a single mom of three kids under fifteen in the 2011-2013 era - you'd know that was the most short-sighted thing anyone could do. JC Penny customers lived for the sales. We waited for them. Looked for the circulars in the mail. We prided ourselves on stretching a dollar and buying back-to-school clothes for multiple kids with the same money that would've barely covered one kid somewhere else. 

Ron never looked at who he as actually serving. 

The problem with these leaders isn't their intelligence or experience. It's that they mistook familiarity for understanding. They made assumptions. They thought they had all the answers, so they stopped asking questions. 

And they skipped the most important step in building anything → seeing clearly first. 

This keeps happening because we keep hiring for content over context. We get dazzled by the big tech names, the accolades, the $50M ARR to $100M ARR growth, the confident answers in the interview room. 

We forget to ask how they think. 

Not what they've done, but how they approach something they haven't encountered before. Do they seek to understand before they build? Do they ask great questions or show up with a ready-made playbook? Can they articulate how to build a system from scratch or do they just tell you about the one they inherited?

The best leaders walk into any new role with genuine curiosity. What are we trying to accomplish? What do we know and what don't we know? What's worked, what hasn't? Who are our buyers, what do they care about, how do they actually behave? Who's on this team, how do we get things done, what does good look like here? They earn their answers before they build anything. 

You see, the most expensive hire isn't the one who doesn't know what to do.

It's the one who's absolutely certain they do.