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How to Challenge Without Being a Jerk

When I first started learning about sales, I made a huge mistake that nearly cost me my career before it began. I thought being "challenging" meant being argumentative, aggressive, and confrontational. I walked into client meetings ready to prove how smart I was by pointing out everything they were doing wrong. Spoiler alert: it didn't go well. The wake up call came during a meeting with a manufacturing executive who had been running operations for twenty five years. I was barely out of college, armed with industry reports and convinced I knew better than someone with decades of experience. Within ten minutes, I had essentially told him his entire approach to inventory management was backwards. He politely but firmly ended the meeting. As I was packing up my materials, he said something that stuck with me: "Son, you might be right about some of this stuff, but nobody's going to listen to you if you make them feel stupid for not knowing it already." That m...

Tap Your Inner Ambivert

 For years, I bought into the myth that great salespeople were born, not made. They were the extroverts – the ones who could work a room, strike up conversations with strangers, and charm their way into anyone's good graces. I watched these natural performers get hired first, promoted fastest, and celebrated most in sales organizations. It all seemed so obvious: if you wanted to sell, you needed to be the life of the party. But then I stumbled across some research that completely shattered this assumption, and it's changed how I think about influence, persuasion, and what it really takes to be effective in our modern, sales-heavy world. The Extrovert Illusion The conventional wisdom isn't entirely wrong about one thing: extroverts do gravitate toward sales roles. They're more likely to apply for these positions, more likely to get hired, and yes, more likely to climb the ladder. From the outside, it looks like validation of everything we've believed about natural...

From Problem Solver to Problem Finder

I've been thinking a lot about what separates great salespeople from the rest these days. After years of watching the landscape shift, I've come to realize that the fundamental nature of selling has transformed in ways most people haven't fully grasped yet. The old playbook doesn't work anymore. I remember when having exclusive access to information was like holding a golden ticket. If you knew something your customer didn't, you had leverage. You could position yourself as indispensable simply because you controlled the flow of information. Take real estate, for instance. There was a time when only licensed agents had access to the multiple listing service. Want to know what houses were available in your price range? You had to go through a realtor. That information asymmetry created real value and gave agents substantial negotiating power. But that world has vanished almost overnight. Today, anyone with a smartphone can access the same property data that profes...

How I Learned to Stop Being a Passenger in My Own Career

There's a moment in every professional's journey when they realize they've been doing their job all wrong. Mine came during a particularly mundane Tuesday afternoon meeting. I was sitting there, mentally checking out, convinced this wasn't "my" meeting. After all, I wasn't leading it. The topic wasn't directly related to my immediate tasks. I figured I'd just nod along, take some notes, and get back to my real work. Then I watched as a colleague—someone at my exact same level—jumped in with a thoughtful question that completely shifted the conversation's direction. She wasn't the meeting owner. She wasn't even in that department. But she saw a connection to something we'd discussed weeks earlier and offered a perspective that ended up saving the project weeks of rework. That's when it hit me: I'd been treating my career like I was riding in someone else's car. The Driver's Seat vs. The Passenger Seat The differe...

What I Wish Someone Had Told Me Earlier When Starting a New Job

I used to think honesty was always the best policy at work. Boy, was I wrong. Picture this: You're three months into a new job, still figuring out the rhythm of your team, when your manager drops by your desk with a question about a project you've been tangentially involved in. Your first instinct? "I'm not sure." It's honest, right? It's straightforward. It should be enough. Except it isn't. What I've learned through years of awkward silences and missed opportunities is that workplace communication operates on a completely different frequency than everyday conversation. There are unspoken rules floating around every office, and nobody's going to hand you a manual. When "I Don't Know" Isn't Enough The truth hit me during a team meeting early in my career. Someone asked about quarterly projections, and I gave my standard "I'm not sure" response. The room went quiet for just a beat too long. Later, I watched a...

What I Wish I'd Known Before My First Day at Every New Job

That Sunday night before starting a new job? Pure dread. I'd lie awake running through nightmare scenarios: What if I can't find the bathroom? What if everyone already has their lunch groups and I'm eating alone at my desk for six months? What if I accidentally reply-all to something catastrophic on day one? After bouncing between enough roles to make my resume look like a travel diary, I've finally figured out the secret: the battle is won or lost before you even show up. The Stalking Phase (But Make It Professional) I used to think researching colleagues online was creepy. Then I realized everyone does it, and the people who don't are the ones eating lunch alone. Two weeks before my last job started, I went full detective mode. Not in a weird way—just enough to figure out that my future desk neighbor ran marathons, my manager had written articles about sustainable design, and three people on my team went to my university. That first day, instead of panicked s...

The Three Questions Everyone's Secretly Asking About You at Work

Remember your first day at a new job? That mix of excitement and terror as you walked through those doors, wondering if you'd worn the right thing, if you should eat lunch at your desk or in the break room, whether saying "hey" was too casual or "good morning" too formal? Yeah, me too. And here's the thing—that feeling never really goes away because every workplace runs on rules nobody bothers to write down. The Invisible Playbook I used to think I was overthinking everything. Turns out, I wasn't thinking enough about the right things. Last year, I watched two people start the same role at my company. Same qualifications, same job description, same training. Six months later, one was leading projects while the other was still asking permission to order office supplies. The difference? One understood the game beneath the game. These aren't the rules in your employee handbook. They're the invisible expectations floating in the air like humidit...