OG Tuesday Issue #246

✅ Today’s Checklist: 

• Break out of the mid-management trap
• Remote team? Here’s how to stay close
• Discomfort = progress (even when it sucks)

🤔 Riddle me this: When I change, I get bigger but weigh less. What am I? (Find the answer on the bottom).

🎮 Side quests = self-care in disguise.

🤖 Move over, mid results—this Claude guide will have you prompting like a pro.

🎁 Corporate gifting, solved. Thoughtful, easy, and actually impressive.

👯‍♀️ Take the quiz your work bestie is definitely using to analyze you.

Being the person who always “gets sh*t done” might feel productive. But ironically, it’s probably keeping you stuck at the Director level.

According to Maya Grossman, an executive coach who’s guided countless leaders from Director to VP, there’s a critical perception shift needed if you want to break into executive roles:

You can either be the go-to “doer,” or you can be seen as leadership material—but rarely both.

Here’s how to spot if you’re stuck and how to shift:

Signs You’re Stuck in the “Doer” Trap:

• Your day is consumed by urgent tasks, not strategic decisions.
• You’re praised for being dependable, not visionary.
• Your workload leaves little time for broader company initiatives.

The “doer” mindset makes you invaluable as an executor—but less visible as a potential executive.

3 Steps to Shift from “Doer” to VP:

1. Prioritize Impact Over Tasks

Great leaders measure success by outcomes, not checklists. Redirect your energy toward projects with strategic alignment.

• Tip: Delegate tasks effectively (here’s a practical guide) and automate low-value activities.

2. Expand Your Strategic Lens

Your scope at the Director level needs to extend beyond your immediate team.

• Ask: “What’s the most significant contribution my department can make to company goals?”
• Tip: Collaborate cross-functionally (McKinsey highlights how cross-team collaboration is essential to senior leadership roles).

3. Communicate Like an Executive

Executives prefer clarity and strategic vision over granular details.

• Instead of reporting: “Project X is complete,” frame it as: “Project X is complete, allowing us to increase market share by Y% next quarter.”
• Tip: Learn how to communicate strategically to signal you’re ready for higher roles.

Ready to make the leap to VP?

Apply to join this high-impact masterclass designed for Directors ready to move up (without burning out or waiting years).

📅 June 16 | 12 PM EST
🎯 Limited to 50 spots

👉 Click here to apply

Become the obvious choice for VP.

Only 1 in 4 employees feel safe sharing ideas or taking risks at work. That’s not just a trust issue. It’s a missed opportunity for innovation, growth, and retention.

As a manager or HR leader, you set the tone. And psychological safety isn’t about fluffy icebreakers or adding another meeting—it’s about building a culture where people feel heard, respected, and supported.

That’s where Traliant’s Psychological Safety training comes in.

This interactive, scenario-based course gives teams the tools to:

• Open up honest conversations
• Handle mistakes with empathy (not blame)
• Create space for diverse ideas to thrive

When people feel safe, they speak up.

And when they speak up, your team levels up.

👉 Try it free.

Because psychological safety isn’t a perk. It’s a leadership essential.

One of our readers shared a challenge I know all too well:

“Most of our team is in another country…communication and engagement are top struggles. Working remotely has increased errors…email and chat aren’t enough.”

With coworkers in Idaho, NorCal, India, Lebanon, the Philippines, and Spain—my teams’ felt that too. And we’ve learned a lot about what actually works in a globally distributed setup.

✅ What’s worked for us:

🕐 Set flexible hours, but define overlap

No one’s expected to work a 9–5 my time. Instead, we set overlap windows for real-time convos, and trust people to manage their flow. Autonomy = better performance.

📅 Never skip your 1:1s

Every Monday, we do 1:1s to check in on goals, blockers, and life. This kind of consistency builds trust, boosts clarity, and keeps things human.

💡 Tip: Leave space for weekend plans, personal wins, or just how they’re feeling. It matters.

💬 Choose your comms on purpose

Everyone lists their go-to channels. For us:

Slack = casual
Text = urgent
Loom = explain once, really well

Check out this guide to set your team’s comms norms.

📽 Loom it, don’t write it

When a task is complex or visual, we record a Loom. It’s faster, clearer, and more inclusive—especially across languages or time zones.

📚 Document like your future self will thank you

Everything lives in one place (Notion, Google Drive, etc.) No digging through Slack threads. No repeating yourself five times. Just easy access, always.

💡 Tip: Consider creating a custom GPT or AI assistant trained on your company docs and FAQs. It’s like having an always-available teammate who knows your processes cold.

Once you’ve nailed the basics, these tools can help deepen connection, clarity, and team culture:

• 👯‍♀️ Virtual bonding: Try casual hangs on Donut, Gather, or Confetti to build connection outside the inbox.
• 📚 Centralized documentation: Use Notion or Confluence to house SOPs, FAQs, and key links.
• 📝 Build a feedback loop: Tools like 15Five help make praise and suggestions a regular thing, not an afterthought.
• 🌍 Lead with empathy: Be mindful of time zones, holidays, and cultural norms. This guide has solid tips for managing globally with care.

✨ Check out more remote team tools here.

Your turn: How does your remote team stay connected?

Reply to this email—I’d love to hear what’s working for you.

Joanna (TA Co-Founder)

But when you’re juggling tax filings, direct deposits, and last-minute PTO requests—while trying to grow your business—it can feel like one wrong click might summon the IRS.

The good news? Payroll tools today are smarter, faster, and way less chaotic. The better news? You don’t need a finance degree to use them.

Here are 3 reader-approved platforms that take the “ugh” out of payday:

🧾 Paychex

Your all-in-one HR command center. From payroll and benefits to compliance, Paychex is built for busy teams that want serious support without the hand-holding. Bonus: their mobile app makes approvals a breeze on the go.

💼 Patriot

Small biz friendly and budget friendly. Patriot offers automated tax filing, free direct deposit, and a no-fuss interface solo founders rave about.

✅ OnPay

Simplicity that scales. OnPay handles payroll, benefits, and HR with a clean interface and stellar support. Bonus: It syncs with your accounting software to save time and sanity.

At the end of the day, payroll shouldn’t be what’s keeping you up at night. These tools help you stay compliant, save time, and get back to what you actually want to be doing—like, oh, I don’t know, building your empire?

✨ Bonus: Most of these offer free trials, so you can test it out before locking it in.

“Get comfortable with being uncomfortable, it’s the only way to grow”. This has helped me reach every new step in my career, I am constantly battling discomfort.

Amy Gattoni (Senior Account Director)

🧳 Chic, functional, and TSA-friendly—this carry-on always books a return trip.

🧠 This list of training tools makes upskilling your team a no-brainer.

🕵️‍♀️ Incogni scrubs your info from the web (goodbye, spam calls!).

🍳 This HexClad pan is giving Father’s Day MVP energy.

• Optimum is hiring for a Direct Sales Representative (Brooklyn, NY).
• Centraprise is hiring for an AWS Data Engineer (Seattle, WA).
• Revature is hiring for a System Architect (Los Angeles, CA).
• Frazer Jones is hiring for a Workday HRIS Professional (New York, NY).
• Cambro Manufacturing is hiring for a Segment Marketing Manager (Huntington Beach, CA).

⭐ View more jobs here >

Have more feedback? 💌 Reply to this email and tell us.

⭐️ Answer to the riddle.

✨ P.S. Want more inspiration and positivity to kick off your week? Sign up for our Motivational Monday texts (U.S. only).

👀 Want to see if your company is a good fit for our 100k+ ambitious readers? Join our Sponsor Waitlist here.