What 25 Years in Corporate Taught Me (in 2 Minutes) ⏱️

The Expensive Education Nobody Warned You About

When I was 30, I thought getting a job at Microsoft was the finish line. Turns out, it was just the starting gun.

I remember my first week at the Redmond campus, wandering around like a lost tourist, clutching my new employee badge like it was a golden ticket.

I genuinely believed that working for one of the world's biggest tech companies meant I'd automatically absorb wisdom by osmosis. You know, just breathe in that corporate air and suddenly understand how the game was played.

That's not how it works.

What followed was 25 years of the most expensive education I never asked for.

Twelve years at Microsoft on the Xbox business, three years at Virgin, five years at Kaspersky Lab, two years at Seiko Epson, and a few other stops along the way. Each one cost me something - time, sleep, the occasional bout of existential dread - but they paid dividends in lessons that no MBA programme could teach.

This isn't theory wrapped in a bow. This is scar tissue.

The Lessons That Left Marks

Over the past quarter-century, I've witnessed brilliant ideas die in boardrooms, watched talented people flee sinking ships, and seen executives make decisions that looked clever on PowerPoint but catastrophic in practice. I've also seen magic happen when the right conditions aligned.

Here's what I learnt, not from textbooks, but from being in the room when things went spectacularly right and devastatingly wrong.

1. You Aren't the Customer (And That's Your First Problem)

At Xbox, we became obsessed with "owning the living room." It sounded visionary in strategy meetings. We'd sit there, drinking terrible coffee, nodding sagely about convergence and ecosystem dominance. Meanwhile, our research was screaming something entirely different at us.

Did we listen? Did we hell.

We lost an entire console generation because we fell in love with our own narrative. The customers were telling us what they wanted, but we were too busy being clever to hear them. It's the corporate equivalent of buying someone a birthday present you want rather than what they'd actually like.

Your customers aren't you. They don't think like you. They don't care about your internal debates or your org chart. The moment you forget this, you've already started losing.

2. Silence Kills Faster Than Bad News

During the Virgin takeover, nobody knew anything. Budgets vanished like socks in a dryer. Decisions were made in closed rooms whilst the rest of us played an involuntary game of Chinese whispers mixed with panic.

Staff fled. The good ones left first because they could.

Here's what I learnt: people can't handle a vacuum. When you don't communicate, people fill the silence with the worst possible scenarios. And they're usually right to do so.

Bad news is uncomfortable. Silence is fatal. At least with bad news, people can plan, adapt, and make decisions. With silence, they just haemorrhage morale and update their CVs.

3. Spreadsheets Don't Build Loyalty

I once worked with an executive I'll call "Mr Corporate" because, well, he deserves anonymity even if his approach doesn't deserve respect. This man built an office within our open-plan space. Actual walls. A door. The works.

He barely spoke to anyone outside of scheduled meetings. Everything was data, metrics, and quarterly reports. Rigorous? Absolutely. Inspiring? Not remotely.

When redundancies came (they always do), guess whose team lobbied hardest to be cut from his empire? Everyone.

You can't spreadsheet your way to loyalty. Numbers matter, but people aren't algorithms. They need connection, recognition, and the occasional reminder that they're working with human beings, not org chart placeholders.

4. Half-Commitment Is Full Failure

Xbox Fitness. Xbox Music. The Microsoft Band.

I could go on, but you get the picture. Each one had potential. Each one could have been something. But leadership wouldn't go all in. They wanted the upside without the risk, the glory without the commitment.

Half-commitment is full failure dressed in a business suit.

When you're not willing to back something properly - with resources, time, attention, and yes, political capital - you've already made the decision to let it die. You're just taking the scenic route to the grave.

Either go all in or don't go at all. This wishy-washy middle ground? That's just expensive drama that wastes everyone's time.

5. CEO Decisions Over Brandy Cost Blood

There's a special kind of decision that gets made at 35,000 feet, in first-class cabins, or over expensive dinners. I call them "brandy decisions" because they usually involve executives who are far removed from the reality of execution.

One such decision at Xbox: launch a Call of Duty console in one-third of the normal time.

Technically, we got it done. But getting it done and doing it right are not the same thing. The team paid the price in 80-hour weeks, compromised quality, and burned relationships with suppliers who thought we were insane (they weren't wrong).

When executives make bold declarations without understanding the realities of implementation, it's not them who pay. It's the people in the trenches who have to make the impossible merely improbable.

6. Preparation Is Your Only Insurance

The Xbox One launch was meant to be perfect. We'd planned every detail, run every scenario, dotted every 'i' and crossed every 't'. Then, one month before launch, everything changed.

Everything.

The only reason we didn't implode was because our preparation was so thorough that we had the foundation to pivot. We'd built in flexibility we didn't know we'd need.

Preparation isn't about predicting the future. It's about being ready when the future surprises you. Because it will. Often at the worst possible moment.

7. Data Without Humility Is Dangerous

"Only 1% of Xbox users use it as a multimedia device."

Leadership looked at that data point and dismissed it. One per cent? Irrelevant. Except the market proved them spectacularly wrong. Turns out, that 1% was just early adopters signalling where things were headed.

Data is powerful. But data interpreted through the lens of arrogance is poison. You need to listen to your frontline, to the people who talk to customers, to the early signals that don't fit your preferred narrative.

The smartest thing you can do with data is remain humble about what it's telling you.

8. Culture and Performance Are Married

I'll never forget the legendary X02 after-party. It was epic. The kind of night that becomes company lore. The next morning, the GM was gone.

You can have culture. You can have performance. But if you try to have one without the other, you'll keep neither. They're married, and it's not an open relationship.

The companies that thrive are the ones that understand this. They celebrate wins. They work hard. They also know that burning people out in the name of performance is just slow-motion suicide.

9. Re-Orgs Are Expensive Theatre

Multiple Xbox restructures. Each one announced with fanfare about "alignment" and "strategic focus" and other corporate jargon that means "we're not sure what we're doing, so let's rearrange the furniture."

Each re-org costs momentum, talent, and focus. People spent months figuring out who reported to whom instead of doing actual work.

Re-org when necessary, not when convenient. And for God's sake, not because the new executive wants to make their mark.

10. Markets Don't Lie. Egos Do.

I killed the Xbox Fitness Band with data. The numbers were clear. The market wasn't there. The product wasn't ready. I presented everything leadership needed to make the right call.

They launched the ‘Microsoft’ Fitness Band a year later.

Two years on, it was written off. Millions wasted. Careers damaged. All because egos couldn't accept what the market was telling them.

Markets are brutally honest. They don't care about your feelings, your PowerPoints, or your quarterly targets. Egos, on the other hand, will lie to you all day long and smile whilst doing it.

What 25 Years Really Taught Me

I've got 15 more lessons where these came from, but here's the thing that ties them all together:

Great leadership isn't about being the smartest person in the room.

It's about creating conditions where the smartest ideas win - even when they're not yours.

Especially when they're not yours.

The best leaders I worked with had egos, sure. But they had something more valuable: the humility to recognise that their job wasn't to have all the answers. It was to create an environment where the right answers could surface, be heard, and be acted upon.

Now It’s Your Turn

So what do you do with all this? Here are some practical actions you can take today:

1. Check your customer blindness: When was the last time you actually talked to a customer? Not a survey. Not a focus group. An actual conversation. Do it this week.

2. Audit your silence: What are you not communicating? What vacuum are you leaving for people to fill with anxiety? Pick one thing and communicate it tomorrow.

3. Review your half-commitments: What projects are you funding just enough to limp along but not enough to succeed? Either commit or kill them. The middle ground is just expensive.

4. Listen to your frontline: Schedule time this month with people who talk to customers daily. Really listen. Take notes. Act on what you hear.

5. Question your sacred cows: What data or feedback are you dismissing because it doesn't fit your preferred narrative? Write it down. Then ask yourself: "What if this is the signal I need to hear?"

6. Create space for better ideas: In your next meeting, try this: speak last. Let others contribute first. You might be surprised what emerges when you're not filling all the oxygen.

Leadership is learnt in the margins - in the mistakes, the failures, the moments when things don't go to plan. These lessons cost me years of my career. Consider them yours for free.

Keep on rockin',

Harvey