Know Your Boss: The Secret Playbook to Anticipating Needs Before They Arise

The Art of Being TEN Steps Ahead

The infamous backpack — stocked with everything from chargers and eye drops to Post-its and mints. Because when you support high-profile executives, staying ready isn’t optional; it’s the standard.

In the world of high-profile executives, talent, and thought leaders, there’s one universal truth — they move fast, and the people who support them must move faster. The Executive/Personal Assistant who can anticipate needs before they arise is the one who becomes indispensable.

This isn’t about guessing — it’s about mastery. I literally kept a backpack with me at all times. Inside: Post-it notes, pens, highlighters, phone chargers (both Android and Apple), gum, mints, eye drops, dental floss — the essentials. I stayed ready.

Because when you support someone operating at that level, unprepared is not an option.

It’s about understanding your executive so deeply that you can predict their next question, prepare their next move, and smooth out potential chaos before it ever hits their radar.

That level of excellence doesn’t happen by accident. It’s learned, practiced, and refined through experience in the field — and I know, because I’ve lived it.

Behind the Curtain: My Years at BET

Every flawless red-carpet moment has a secret behind it. What looks effortless in the spotlight is often the result of strategy, preparation, and a calm pivot behind the scenes.

Before we get tactical, let me set the stage with a story.

It was cold and rainy in Los Angeles on the day of the 2023 NAACP Image Awards. We were told the carpet would be uncovered and outside. I had a pair of stiletto heels ready—perfect for the velvet dress I planned to wear—but when I peeked out the window and saw the rain pouring down, I knew I needed a Plan B.

Before getting dressed, I made a quick dash to Nordstrom Rack directly across the street from our hotel. I had less than ten minutes to make a decision. I refused to be slipping and sliding on the red carpet, so I went hunting for a rain boot. With none in sight, Sorel was the best option. And the best part was that no one had a clue.

The secret behind the red carpet shot. When the forecast changed, so did the footwear — because preparation always beats panic.

When time is ticking, I don’t panic—I pivot.

No matter the event, being ready to run amidst the chaos has always been my first and foremost agenda.

That moment wasn’t about fashion—it was about foresight.

And that instinct didn’t come overnight. It was sharpened by years of working behind the scenes at one of the most fast-paced networks in entertainment.

I spent eight consecutive years supporting the President of Media Sales at BET Media Group, a role that placed me at the intersection of entertainment, advertising, culture, and high-stakes leadership. BET, founded by Bob Johnson, wasn’t just a television network — it was a cultural movement. It became the first Black-owned cable network to reach national audiences and set the tone for how the world consumed Black excellence, artistry, and innovation.

More than a network — BET is a cultural movement that redefined how the world experienced Black excellence, artistry, and innovation.

What MTV and VH1 later attempted to replicate, BET had already pioneered. From the BET Awards and Soul Train Awards to BET Experience Weekend and the NAACP Image Awards, BET wasn’t just entertainment — it was representation, business, and brand influence on a global scale.

And the man I supported? Let’s just say he wasn’t your average executive.

He’s a 2023 Advertising Hall of Famer, a fashion-forward visionary, and one of the most respected figures in media. Married for over two decades and traveling nearly 250 days a year, he’s spent almost three decades with BET Media Group, helping to shape its cultural legacy. His circle of influence spans from President Barack Obama and Hip Hop icon MC Lyte, to Daymond John of Shark Tank, DJ D-Nice of Club Quarantine, film producer Will Packer, Devale and Khadeen Ellis — Tyler Perry actors, content creators, and hosts of the hit podcast Ellis Every After, and Grammy Award–winning artist Jon Batiste.

Supporting a leader of that caliber means you don’t just assist — you operate. You run systems, anticipate shifts, and move with precision. You become the calm in the chaos, the invisible force that keeps everything on track.

Lesson One: Be the Solutionist

This is what being a Solutionist looks like — poised, present, and finding answers before anyone realizes there’s a problem.

During my tenure, one piece of advice defined everything:

“Manage my expectations.”

That wasn’t just a command — it was a mindset.

To make his life seamless, I had to become what I now call The Solutionist. I carried a spirit of excellence 24/7, because there was no room for mediocrity in his world.

I learned his favorite restaurants in every city he frequented, his shoe size, his preferred smoothie ingredients, the kind of water he drank, even his tone of voice when something wasn’t quite right. I memorized birthdays, anniversaries, flight preferences, and exactly what kind of car he wanted waiting in Los Angeles, New York, Miami, or Chicago — no detail too small, no decision left to chance.

If you can think of it, I probably knew it — or could find out very quickly.

Why? Because every detail mattered. In a world where every minute counts, being the person who removes friction is what separates a good assistant from an exceptional one.

Lesson Two: Know the Person Behind the Title

Supporting an executive goes beyond tasks — it’s about connection, awareness, and understanding the people who matter to them. Relationships are part of the strategy.

When you support high-profile talent or executives, it’s not just about handling logistics — it’s about understanding the human behind the title.

You must know their values, their quirks, their stress triggers, and the small things that bring them peace in high-stakes moments. Family is part of that equation too.

If your executive’s spouse’s birthday or child’s recital isn’t on your radar, you’re missing part of the bigger picture. Their home life affects their headspace, and their headspace affects you.

So, I kept tabs on anniversaries, birthdays, and milestones — not just because it was thoughtful, but because it reinforced that I saw them as a person, not just a project.

The best assistants blend empathy with efficiency. They handle business with precision and people with care.

Lesson Three: Build Systems That Think for You

When your crew’s in sync, everything flows smoother — teamwork makes the chaos work.

When your boss travels 250 days a year, there’s no such thing as “winging it.”

Every preference — from hotels and drivers to in-room amenities — needs to be documented and retrievable in seconds. I knew which hotels had the best views, which ones were too close to the elevators, and which concierge could make miracles happen during a sold-out weekend.

I built relationships with general managers in every city. I kept their cell numbers and direct emails. Because when things went sideways — a flight delay, a missing reservation, or a last-minute schedule change — I didn’t have time to wait on a 1-800 number.

Being a proactive assistant isn’t just about knowing what your executive needs — it’s about building systems that ensure those needs are met before they have to ask.

Lesson Four: Feed the Body, Fuel the Brand

Energy, structure, and foresight — the foundation of every successful assistant who makes it possible.

You can tell a lot about a leader by how they eat — and how they handle their schedule.

Food preferences aren’t just about taste; they’re about rhythm. For a jet-setting executive, having the right meal, drink, or snack can mean the difference between a calm meeting and a chaotic one.

I knew every city’s go-to restaurant, the chefs who could take a last-minute call, and the exact meal that would hit the spot after a long flight. When your executive walks into a hotel room and finds their favorite smoothie already waiting, it’s not a coincidence — it’s a silent statement that says: I’ve got you covered.

It’s the same with scheduling. Every assistant knows the calendar is sacred — but a great assistant understands the energy flow behind it. Meetings aren’t just blocks of time; they’re mental sprints. Protecting that time strategically is part of the art.

Lesson Five: Relationships Are Your Real Currency

Behind every flawless production is a network of professionals working in sync. From photographers and makeup artists to hospitality staff and family, relationships are the real currency that make excellence possible.

Here’s something most people miss: being an elite assistant is 50% logistics and 50% relationships.

You can’t serve a high-profile executive in isolation. You need strong ties with their network — from the financial advisor and publicist to the hotel concierge and restaurant manager.

When you have a crisis (and you will have one), the people you’ve built genuine rapport with will pick up the phone, bend the rules, and help you fix it.

In my role, I made it my mission to connect with everyone — drivers, stylists, assistants to other executives, and even the families of close colleagues. Knowing who to call in a crunch is half the battle.

Your executive’s reputation is often intertwined with your responsiveness, and that’s why relationships are not optional — they’re essential.

Lesson Six: Learn the Business — Not Just the Boss

To truly anticipate needs, you must understand the context of their world.

At BET, that meant more than managing calls and calendars. It meant understanding celebrity dynamics, knowing who the key advertisers were, what “upfronts” meant, and how culture influenced brand solutions.

The more I understood the business, the better I could anticipate what my executive would need next. If a major partnership was brewing, I prepped notes. If a new waymaker emerged, I recommended them.

Because when you understand the business, you don’t just assist — you advise. That’s when you move from being an assistant to becoming a strategic partner.

Your voice starts to carry weight — not because you asked for it, but because you’ve earned it.

Lesson Seven: Ask, Observe, Adapt

Write it down. Track it. File it. The key to mastery is documenting every detail until it becomes instinct.

If you’re new in your role, the best thing you can do is schedule a “Get to Know You” session early on.

Come prepared with thoughtful questions — not just about logistics, but about personality. Ask about their preferred communication style, how they like to receive updates, what they consider a “win” in their day.

And then? Observe.

Watch how they react in meetings, how they speak to different people, what triggers frustration or satisfaction. Those observations will become your roadmap.

Over time, you’ll develop what I call “executive intuition” — the ability to read the room, anticipate patterns, and operate seamlessly.

If you’re already seasoned but still feel like you’re missing key pieces, it’s never too late to learn. Schedule that meeting. Gather the data. Update your systems. Excellence is a choice, not a title.

Lesson Eight: The Power of Poise Under Pressure

Stay calm. Stay poised. Channel your inner Patrick.

When you’re supporting someone who’s known worldwide, chaos is inevitable.

You might be juggling multiple award shows, brand partnerships, and personal obligations — all before noon.

But here’s the truth: the best assistants don’t crumble. They pivot.

Like wedding planners in a storm, they keep their composure while troubleshooting quietly behind the scenes. They stay calm when everyone else is spiraling.

Your ability to project steadiness — even when your phone is blowing up with “urgent” requests — is what earns trust. It’s what makes executives breathe easier knowing you’ve got it handled.

High performance requires high endurance — and I don’t mean that lightly.

Sometimes peace looks like a hallway, a plate of food, and twenty minutes to breathe before the next wave of chaos hits.

High performance requires high endurance — and I don’t say that lightly.

When you support a high-profile executive whose schedule never stops, boundaries blur fast. I wasn’t just reachable — I was available to him and anyone connected to him. That level of access came with the territory, and honestly, it’s part of what made me effective. I stayed ready because I stayed present.

But even the best assistants need a moment to recharge. I remember during the 2022 Men’s Summit, I had gone the entire day without eating. In between managing talent, production, and guests, I slipped into the back kitchen and asked the chef for a plate. The only available seats were among attendees and celebrities — and I knew the moment I sat down, someone would need something.

So I found a quiet hallway, sat on the floor, and ate. For twenty minutes, I let myself just be — no phone, no questions, no multitasking. That small pocket of stillness reset me enough to finish the night strong.

Protecting your peace doesn’t always mean saying “no.” Sometimes, it means carving out a sliver of calm in the middle of chaos — even if it’s in a hallway with a plate of food. Because the truth is, you can’t pour into others if you’re running on empty.

Lesson Ten: Why This Matters — The Bigger Picture

That moment when everyone looks your way — and you simply say, “I got it.” Because great assistants don’t just support the mission, they run the operation.

Here’s the truth that no one tells you: assistants are often the unsung strategists behind high-profile success stories.

Every seamless transition, every flawless event, every “impossible” achievement that looks effortless on the outside — usually has an EA/PA at its core, running the playbook quietly and precisely.

Knowing your boss — truly knowing them — allows you to transform from “the help” into the asset. You stop reacting and start directing. You become the person they trust with access, influence, and insight.

And when that trust is earned, doors open that no title alone could unlock.

The CMC Standard

Crystal Marshall Certified — where excellence isn’t just taught, it’s refined.

The ability to anticipate your executive’s needs before they even articulate them isn’t just a skill — it’s an art form.

At Crystal Marshall Certified (CMC), we teach assistants how to master that art. Through twelve comprehensive modules, including “Know Your Boss,” we help you transform from a capable support professional into an indispensable strategic partner.

You’ll learn how to read your executive’s rhythms, build bulletproof systems, communicate with confidence, and operate with the poise of a world-class professional.

Because the truth is — the industry doesn’t reward those who just do their job. It celebrates those who elevate it.

Final Thought

If there’s one thing I’ve learned from years in high-stakes executive support, it’s this:

Excellence isn’t about being perfect. It’s about being prepared.

So study your executive, stay two steps ahead, and never stop refining your craft.

That’s how you turn your role into a legacy — and yourself into a brand.