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Everyone loves to tell busy founders, “You need an assistant!” But here’s the problem not all assistants are created equal. And if you hire the wrong one, you’ll waste money, get frustrated as hell, and end up thinking assistants don’t work.
In this episode of World’s Greatest Boss, I break down the three main types of assistants: Virtual Assistant (VA), Personal Assistant (PA), and Executive Assistant (EA).
You’ll learn exactly what each one does, the benefits and drawbacks, signals that it’s time to hire, and how to actually find the right one. By the end, you’ll know which assistant can buy back your time without making a costly hiring mistake.
What You’ll Learn in This Episode:
Why This Matters:
Hiring the wrong kind of assistant is one of the most expensive mistakes you can make as a founder. Whether you’re drowning in repetitive admin tasks, losing weekends to errands, or stuck in the weeds of business operations, the right assistant can give you back your time — and your sanity.
Resources and Links:
If you enjoyed today’s episode:
In this episode of World’s Greatest Boss, we dig into one of the biggest challenges service-based business owners face: balancing client growth with team health. My guest, Borja Cuan, co-founder of 415 Digital, manages over $280 million in ad spend every year—and he’s built a thriving business by doing something most agencies won’t: keeping workloads small so his team can go deeper, deliver better results, and stay engaged.
Together, we explore:
Borja’s approach flips the typical agency model on its head—and his insights on retention, loyalty, and workload management will challenge how you think about leading your own team.
By the end of this episode, you’ll have fresh ideas for keeping your people motivated, building loyalty, and leading a team that doesn’t just survive—but thrives.
Connect with me on Linkedin: https://www.linkedin.com/in/jackiemkoch/
Find more information on my website: https://peopleprinciples.co
Connect with Borja Cuan on Linkedin: https://www.linkedin.com/in/borjacuan
Find more information about Four15 Digital: https://four15digital.com/
What happens when you know someone on your team isn’t performing but you keep putting off the conversation? In this episode of World’s Greatest Boss, I break down exactly why avoiding performance conversations is one of the costliest mistakes you can make as a leader.
We’ll cover six powerful reasons to address performance issues early, from keeping your top performers engaged to protecting your business from legal risk. I’ll also walk you through the most common excuses leaders give for delaying these convos (and why they don’t hold up), plus my simple, no-drama framework for having these conversations without making them confrontational.
By the end of this episode, you’ll have the tools to give feedback faster, protect your culture, and actually help your team members improve without losing sleep over it.
Quick-hit framework for performance conversations:
Resources & Links:
People Strategy Is Business Strategy: The Essentials You Need
Think HR should handle all the “people stuff”? Think again.
In this episode, I’m calling out one of the most common mistakes founders make when trying to scale—treating people strategy like an admin function or annoyance instead of core business strategy. I break down exactly what people systems you need and why this is all a part of your overall business operations strategy, not something else you need to do.
We’ll talk through the key systems every small business needs to grow a high-performing team, how to divide ownership between HR, managers, and leadership, and what happens when you avoid the hard conversations and hope someone else will handle them for you.
If you’ve ever said, “I just need to hire a strong HR person to manage the team,” this episode is for you.
What you’ll hear in this episode:
Resources + Links
High-performing cultures aren’t built by rules—they’re built by leaders who take full responsibility.
In this episode of World’s Greatest Boss, I’m joined by Andrew Horn, executive coach to CEOs at companies like TOMS and Hinge, and the founder of Tribute.co. After scaling his startup to 120 employees and overseeing a successful exit, Andrew now dedicates his work to helping founders, CEOs, and leadership teams master relational leadership—a framework that fosters trust, accountability, and real cultural change.
We dive deep into Andrew’s 5-step framework for moving from reactivity to conscious leadership. You’ll learn how to identify your own unmet needs, how to respond to conflict without judgment, and how to create small rituals that lead to big cultural impact.
Whether you lead a small team or a growing company, this conversation will challenge you to lead with intention—and give you tangible tools to help your team thrive.
What You’ll Learn in This Episode:
Resources Mentioned:
Connect with Andrew Horn:
Connect with Jackie:
If you’ve ever caught yourself thinking, “They should know better” about someone on your team, this episode is for you.
In today’s episode I break down a trap that many founders and managers fall into: holding secret expectations—unspoken rules that frustrate you when broken but were never actually communicated in the first place.
Whether it’s scheduling mid-day appointments, not replying fast enough, or showing up unprepared to meetings, these invisible standards hurt performance, erode trust, and create unnecessary team drama.
I share real-world examples from my HR consulting work, explain why this dynamic happens (even to the best leaders), and give you a step-by-step guide to setting clear, kind, and actionable team operating procedures that support accountability without micromanaging.
What You’ll Learn:
Stay Connected:
What does it really take to build a team that believes in your mission…. and sticks around?
In this episode of World’s Greatest Boss, I sit down with Rachel Lauren, the co-founder and COO of Debbie, a platform that flips the script on financial rewards by helping users earn points for good money habits. Rachel and her team have grown Debbie from zero to 70,000+ users and just as impressively, from 2 scrappy co-founders to a 12-person, mission-driven team.
We talk through the real decisions startup leaders face when hiring: when to buy vs. build talent, how to manage performance without overcomplicating things, and why frequent feedback actually improves employee output.
You’ll walk away with ideas to put in place right now whether you’re managing one person or a small but mighty team.
What You’ll Hear in This Episode:
[1:00] The backstory behind Debbie and how rewards for good financial habits work
[3:30] Why mission alignment matters—and how it helps attract great talent
[5:05] Build vs. Buy: How they developed interns into leaders
[10:20] A refreshingly simple performance review cadence (and why it works)
[18:45] When and how compensation conversations happen—and why they keep them separate from reviews
[22:00] Setting promotion expectations, especially with Gen Z team members
[25:45] Rachel’s surprising inspiration for leadership: the Dallas Cowboys Cheerleaders documentary
Resources & Mentions:
Connect with Jackie:
What if the person you’re about to fire isn’t the problem… it’s the role they’re in?
In this episode of World’s Greatest Boss, Jackie Koch talks with Brice Jaggars, bestselling author of Two Fish in the Tree, about how role alignment and soft skills play a huge role in team performance. Brice shares practical tips for figuring out if someone is in the wrong job, how to spot soft skill mismatches, and what to try before you cut ties with a struggling employee.
Whether you’re leading a small team or managing a growing company, this episode will help you rethink how you approach performance issues and keep the right people on board.
What You’ll Learn:[1:30] Why performance issues often come down to the wrong role
[3:15] The difference between technical skills and soft skills
[4:20] The most common soft skill gaps that cause problems
[6:15] What to do when you want to keep someone but their current job isn’t working
[7:55] A real-life example of reassignment that worked
[9:30] Why not everyone can fit into the same mold
[11:00] How to decide when it’s time to move on
[12:15] Coaching new grads versus managing experienced team members
[13:25] Why remote work makes soft skill development harder
[14:35] Brice’s inspiration behind Two Fish in the Tree
Resources & Links:If you’re still relying on job boards to hire your next great employee, this episode is your wake-up call. I break down why “post and pray” is no longer an effective hiring strategy especially if you’re trying to land top-tier talent.
Instead, you’ll learn the three proactive methods recruiting teams use every day to find the right people (and how you can do it yourself as a founder, hiring manager, or business owner). No agency fees required.
What You’ll Learn:
Free Resources Mentioned:
FREE Hiring Handbook + Interviewing Masterclass 👉 peopleprinciples.co/hiring
📲 Connect with Jackie: 🔗 LinkedIn & 🌐 peopleprinciples.co
In this episode I’m joined by Art Shectman, founder and CEO of Elephant Ventures, a global innovation firm helping companies unlock the full potential of AI transformation. But we don’t just talk tech: we dive into the human side of building and leading a business.
Art shares how he intentionally designed a company culture built on dependability, psychological safety, and joyful work. We talk about how his team successfully adopted a compressed four-day workweek, and what it really takes to implement major organizational shifts like AI adoption without sparking panic or burnout.
You’ll walk away with a better understanding of how to structure your team for accountability (without toxicity), why empowering employees beats micromanaging every time, and how to lead transformation with honesty, clarity, and how to get buy-in from the ground up.
If you’re thinking about hiring across borders, piloting a 4-day week, or embracing AI in your business you don’t want to miss this one.
What you’ll hear in this episode:
[1:40] How Elephant Ventures helps companies get 20X results from AI - not just 20%
[3:29] Why Art started hiring internationally in 2008
[4:12] The early struggles of global hiring (and why EORs are game-changing now)
[7:17] Why founders must prioritize their “joyfulness battery”
[10:17] Building culture intentionally: dependability, kindness, and the value pyramid
[14:02] Holding people accountable without being toxic
[18:17] How Elephant Ventures rolled out a compressed 4-day workweek
[22:15] Lessons from testing and scaling flexible work
[24:10] Coaching teams through AI transformation without fear
[26:29] Creating psychological safety in practice
[30:06] Why vulnerability and consistency matter more than charisma
[32:19] Where to find Art’s thought leadership on AI and transformation
Resources and links:
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