OG Tuesday Issue #237

A stylized graphic with a pink figure flexing their arm in strength next to the text: "I leave what no longer serves me in the past.”

✅ Today’s Checklist:

Balancing command & compassion
A guide to managing Gen Zers
Choosing “different” isn’t a bad thing

🤔 Riddle me this: What English word has three consecutive double letters? (Find the answer on the bottom).

QUICK LINKS

💪 No matter your age, you can face the fear of “what if?” head-on to make the big career change you’ve been dreaming about.

🧘‍♀️ How to keep anxiety from taking over before you’ve even brushed your teeth.

💸 Five smart money moves that also benefit your mental health.

🙃 If you’re a workplace people pleaser, do these 3 things now to protect your energy.

LEADERSHIP

Illustration of one person at a desk working on a computer while another holds a giant umbrella over them, shielding them from rainclouds, symbolizing support at work.

Empathy vs. Authority—Why Great Leaders Need Both

Many leaders fear that leaning too far into empathy can weaken their authority. But the truth is, you can be both compassionate and respected.

Leadership is more than decision-making and delegating—it’s also about inspiring and guiding people toward a shared vision and goal. The key is striking a balance.

💭 Lead with Understanding, Not Leniency

Empathy doesn’t mean excusing poor performance. It’s recognizing challenges while still holding employees accountable and working on a solution that meets both their needs and the company’s goals.

Ex: Mary Barra (CEO of General Motors) led GM through a crisis with both accountability and empathy. She publicly apologized for safety failures while implementing major culture changes to prevent future issues.

🗣️ Communicate Clearly and Consistently

Empathetic leaders listen, but they also communicate expectations decisively. Explaining the “why” behind your decisions shows that you consider both the business’s needs and your employees’ well-being.

Ex. Rosalind Brewer (CEO of Walgreens Boots Alliance) advocates for diversity and inclusion while setting high expectations and making strategic decisions that drive success.

🧭 Set Boundaries While Supporting Your Team

Empathetic leaders can’t take on everyone’s emotional burdens. Offer support and resources but encourage self-sufficiency.

Ex: Oprah Winfrey built an empire through deep empathy and decisive leadership. She connects personally with people while maintaining extremely high standards for her brand.

😍 Model the Behavior You Want to See

If you want to create a culture of respect and collaboration, you’ll need to walk the walk. To build trust and project a leadership mindset, it’s vital that you remain cool under pressure, handle conflicts maturely, and treat others with respect.

Ex: Indra Nooyi (Former CEO of PepsiCo) showed emotional intelligence by sending personal thank-you notes to her executives’ parents while making bold business moves, like pushing PepsiCo toward healthier products.

⚖️ Balance Tough Conversations with Compassion

“The most important leadership principles can be found in what we teach our children—empathy, curiosity, bravery, and kindness… Let the traits of decent human beings be the traits of decent leadership.”

Ex: Jacinda Ardern (Former Prime Minister of New Zealand) led with empathy and strength, addressing crises like terrorist attacks, the pandemic, and a volcano eruption with kindness and humanity while making firm, necessary decisions.

Empathy and authority in leadership aren’t mutually exclusive. When blended, they create a workplace where employees know they’re valued and feel motivated without compromising on leadership strength.

💼 Want to level up your leadership even further?

Empathy and authority are only part of the puzzle. If you’re eyeing a VP role (or just want to be seen as the obvious choice for your next big move), this free masterclass breaks down the 3 things you actually need to get promoted.

HEALTH & WELLNESS

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Sick of Failed Diets? There’s a Smarter Way to Lose Weight

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Whether your goal is more energy, improved digestion, or just feeling better in your skin, this app meets you where you’re at.

Take the quiz and get 50% off today.

BIGGEST CHALLENGE

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A Guide to Managing a Gen Zer

TTA reader Breanna shared: The biggest challenge I’m currently facing is the Gen Z workforce!

Look, I get it. I’ve seen the IG Reels (yes, Millennials, I’m looking at you 👀) dragging Gen Z for being “lazy” and “entitled.” And listen—I’m not here to defend every questionable workplace behavior from my generation. But as The Assist’s resident Gen Zer, I am here to give you some insider intel on how to manage us in a way that actually works.

Spoiler: It’s not about coddling us. It’s about understanding what drives us. Let’s get into it.

I’ll Respect You If…

You’re transparent.
You communicate clearly.

I don’t care about titles—I care about leadership. Leadership is a behavior, not a title. If you set clear expectations, hold yourself accountable, and treat everyone with respect, you’ll have mine.

I’ll Hate You If…

You waste my time. Meetings that should have been emails? And to be honest, does anyone want their time wasted away by a day FULL of meetings?!
Pointless busy work? Outdated systems that make everything harder than it needs to be? No thanks.
You ignore my ideas. If I feel like my input doesn’t matter, I’ll stop giving it.
You micromanage. If you don’t trust me to do my job, why did you hire me?

Here’s What’s Important to Me…

Impact. I need to know my work actually means something. If I feel like I’m just another cog in the machine, I’ll mentally check out. Connect my role to the bigger picture or the company’s goals, and I’ll be way more invested.
Growth. I’m not here to sit still. Give me opportunities to learn, challenge myself, and level up. If I don’t see a path forward, I’ll start looking elsewhere.
Recognition. No, I don’t need a gold star for every little thing—but a quick “Hey, great job on that project” goes a long way.

And if you really want to motivate me? Think beyond pizza parties. Time off, bonuses, or career development opportunities hit way harder.

Here’s What I Don’t Care About…

Corporate hierarchy. Just because someone has been at the company longer doesn’t mean they automatically know better. I respect experience, but I also value fresh perspectives and collaboration over rigid org charts.
Face time. I don’t believe in sitting at my desk just to “look” productive. If I get my work done and do it well, I don’t need to be in the office just for the sake of it.
Outdated work norms. If the only reason we’re doing something is “because that’s how it’s always been done,” I’m gonna challenge it.

Here’s How to Approach Conflict…

Just be real with me. I respect honesty, but how you say it matters. If I’m messing up, tell me—but frame it in a way that helps me improve, not just makes me feel like garbage.

🚫 “You’re not meeting expectations.”
✅ “Here’s what’s not working, and here’s how we can fix it.”

I’ll take feedback way better if I know it’s coming from a place of support rather than just criticism.

Here’s How to Motivate Us…

Make it clear what success looks like. Vague feedback like “take more initiative” doesn’t help—tell me exactly what you want, and I’ll make it happen.

Give me autonomy. Let me own my work, try new things, and figure out the best way to get results.

Offer real rewards. Want me to go above and beyond? Recognize my efforts in a way that actually matters. More PTO? Career growth opportunities? A bonus? Yes, please.

I Will [X] If My Manager Does [X]

✔️ I’ll give 110% if you set clear goals and expectations.
✔️ I’ll stay engaged if you invest in my growth.
✔️ I’ll be loyal if I feel valued, supported, and part of the team.
✔️ I’ll bring my best ideas if I know they’re actually being heard.

If you meet me halfway, I’ll match your energy—and then some.

Why You Actually Want a Gen Z Employee

I get it—hiring us might seem like a risk. We job-hop, we push back on outdated norms, and we don’t live to work. But here’s why you should want us on your team:

💡 We’re digital natives. We grew up with the internet and know how to make tech work for us (and you). Want to go viral like Duolingo? Hire a Gen Z.

👀 We’re bold and honest. We’ll tell you what’s working, what’s broken, and what could be better—no sugarcoating.

🔥 We’re creative problem-solvers. We don’t accept “because that’s how it’s always been done” as a reason. We’ll find smarter, faster, and more efficient ways to get results.

🏆 We want to succeed together. Give us autonomy, purpose, and room to grow, and we’ll go all in.

At the end of the day, managing Gen Z isn’t about catering to us—it’s about evolving. The workforce is changing, and the best leaders aren’t the ones resisting it—they’re the ones adapting and thriving.

Cameron, TA Newsletter Ops Manager

PROJECT MANAGEMENT

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Time-Saving Hacks You Wish You Knew Sooner

Smartsheet is already a powerhouse for project management, but there are a few hidden gems that can drastically improve your work efficiency and time management. Here are five lesser-known features you can start using today to take your productivity to the next level:

🔗 Cell Linking: Stop Duplicating Work

Use cell linking to sync cells across sheets. Update once, and watch the magic happen—your data automatically updates wherever it’s linked.

🎨 Conditional Formatting: Make Data Jump Off the Screen

Stop squinting at your sheets, trying to find important data. With conditional formatting, you can color-code tasks based on urgency or status. Instantly spot overdue tasks, high-priority items, or any data that needs your attention.

🔄 Dependencies: Let Your Projects Manage Themselves

With dependencies, link tasks together so they adjust automatically when something changes. One task slips? Your whole project shifts accordingly.

🤖 Automated Workflows: Work Smarter, Not Harder

Set up automated workflows that trigger actions when tasks are marked complete. Send notifications, request approvals, or update statuses with zero effort.

⏳ Version History: Never Panic Again

Made a mistake? Don’t sweat it. With version history, you can roll back to previous versions and restore your data in seconds.

Learn how Smartsheet can streamline your projects.

SUBSCRIBER SPOTLIGHT

Don’t Shy Away From Something Different

“Don’t be afraid to try on the ugliest thing in the store because you don’t know what you don’t know and, who knows – maybe that ugly shirt looks amazing on you. Don’t be afraid to try something outside the norm.”