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In this episode, I unpack why most startup onboarding is quietly destroying retention, burning cash, and stalling productivity, and what to do about it.

Using research, real-world examples, and a practical framework, I'll walk through how to transform onboarding from a rushed checkbox exercise into one of the highest-ROI systems in your company. You’ll learn where your current process is failing, how to fix it without drowning managers, and how to architect a shared accountability model that actually delivers results.

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In this episode, I talk with Barbara Wittmann, founder of Digital Wisdom Collective, about why so many digital and AI initiatives quietly fail, and what it really takes to make transformation stick.

We go beyond tools and platforms to explore the deeper system of people, structures, and culture that Barbara calls “human infrastructure”, and why this matters even more in startups where the pace is fast and the margin for error is thin.

• Why Digital Transformation Fails (Even with Great Tech): How organizations keep treating transformation as an IT project, and the recurring people and structure patterns behind failure.
• Human Infrastructure as a Strategic Asset: What “human infrastructure” actually means—mindsets, capabilities, relationships, and learning rhythms—and why it should show up as its own budget line item.
• The Real Role of Middle Management: Why change “starts in the middle,” how middle managers become the load-bearing walls of any transformation, and what happens when they’re bypassed or underpowered.
• AI Without the Hype (and Without Panic): The difference between responsible AI adoption and shiny-object chaos, including the reality that some roles will disappear—mostly the ones that never fully leveraged human capability—and how this is an opportunity to double down on work humans do best.
• HR and IT as the New Power Couple: HR and IT must operate as true partners in startups, co-owning outcomes, roadmaps, and the design of how people and technology evolve together.
• What Startups and HR Leaders Need to Do Differently: Concrete guidance for founders and HR leaders on aligning tech choices with business outcomes, building human infrastructure early, and avoiding “transformation theater.”

• Connect with Barbara on LinkedIn
• Learn more about Digital Wisdom Collective

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In this episode, I sat down with Nikki Barua to explore what it really takes to build a long‑term company in the age of AI. Together, we unpack when it makes sense to bootstrap versus raise capital, how misaligned investors can quickly push out founders, and why many businesses would be healthier if they grew more patiently instead of chasing funding as a badge of honor.

The conversation then turns to who should own AI enablement (IT vs HR), why putting AI solely in IT is a red flag, and how to rethink headcount: not as “how many jobs can we cut,” but as “which tasks and roles can AI absorb so humans can move into higher‑value work.”

Links:

• Nikki Barua's LinkedIn profile: https://www.linkedin.com/in/nikkibarua
• FlipWork website: https://www.flipwork.ai/

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In this episode of the Organized Chaos podcast, I explore profit sharing as a strategy for business growth with my guest Rob Gallagher, CEO of Profit X.

Rob shares his journey from an unplanned construction business owner to a seasoned entrepreneur advocating for strategic profit sharing. He illustrates how aligning employee and organizational goals can transform company culture and drive explosive growth.

Through personal anecdotes and insights, Gallagher emphasizes the importance of clarity and setting clear expectations in profit sharing, warning of initial pitfalls and highlighting the model’s potential to evolve companies into powerhouse businesses.

Links:

• Rob Gallaher's LinkedIn profile: https://www.linkedin.com/in/robertgallaher
• ProfitX website: https://profitx.co
• Profit Sharing book: https://a.co/d/bgTgdsk

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In this episode, I am joined by Halisi Tambuzi, J.D., an expert in HR workplace investigations, to demystify the often-intimidating world of HR compliance for startups. Many early-stage companies place HR on the back burner, but as Halisi explains, this can lead to significant legal, financial, and cultural consequences. We dive into the practical steps founders and leaders can take to build a compliant and resilient organization from the ground up.

This conversation is a must-listen for any startup founder, leader, or aspiring entrepreneur who wants to understand the "when" and "how" of implementing HR best practices without breaking the bank.

In this episode, you’ll learn:

• Common HR Blind Spots for Startups: Why are small companies and startups particularly vulnerable to HR compliance issues? We break down the common misconceptions and challenges they face.
• The Right Time to Focus on HR: Is it after the first hire? The tenth? The twentieth? We identify the key milestones and triggers that signal a startup must prioritize creating HR infrastructure.
• The High Cost of Non-Compliance: We explore the tangible risks—from legal liabilities and costly investigations to damage to company culture and morale—that come from neglecting HR compliance.
• Lean HR Strategies: Discover how resource-constrained startups can effectively manage HR needs through smart strategies like fractional HR support and leveraging the right technology.
• Avoiding Workplace Conflicts: We share insights into the most frequent mistakes that lead to internal investigations and how proactive HR policies can prevent them.
• The Future of HR: A look at how emerging trends like artificial intelligence and the permanence of remote work are reshaping the landscape of HR compliance and presenting new challenges for employers.

Halisi Tambuzi, J.D., is a seasoned expert in workplace investigations and HR compliance. With a background that bridges law and human resources, she provides critical guidance to companies to help them foster fair, respectful, and compliant work environments.

• LinkedIn: https://www.linkedin.com/in/halisi-tambuzi-j-d-657b7227/
• Company Website: https://wpihr.com/

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In this episode of Organized Chaos, I am joined by Gwenevere Crary, founder of Guide to HR and host of the "Scaling with People" podcast. Gwenevere is a strategic visionary in the HR world and she shares her forward-thinking approach to AI-enabled HR strategies and the unique challenges startups face as they scale.

• Guinevere's Journey to HR: From a background in actuarial mathematics to leading people operations in high-growth startups.
• AI Enablement in HR: How to leverage AI to automate tasks you hate and augment your own skills, whether in writing or data analysis.
• The Future of HR with AI: A look at advanced AI applications, including a 24/7 AI coach for managers that facilitates role-playing for difficult conversations and tracks employee development goals.
• New Skills for HR Professionals: The need for HR leaders to possess deep business acumen, understand company financials, and think like a business operator. The traditional, admin-heavy HR role is obsolete.
• Challenges in Scaling Startups: Advice for HR professionals on how to gain credibility, present themselves as strategic partners, and build crucial relationships with leadership.
• HR's Role in Owning Technology: Why HR is positioned to own AI implementation, ensuring its use is safe, unbiased, and effective for the entire organization.
• The Hard Truth: Knowing when to leave a role if you no longer have the trust and alignment with leadership to be effective.

• Connect with Guinevere on LinkedIn.
• Learn more at Guinevere's website: guidetohr.com
• Take the free AI Readiness Assessment to see where you and your organization stand.
• Listen and subscribe to the Scaling with People Podcast.

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In this episode, I dive deep into how startups can turn chaotic, gut-driven hiring into a scalable, data-driven system that fuels high-growth.

I'll break down a six-step framework for building a structured interview process that dramatically improves hiring accuracy and reduces bias. The episode includes a practical guide, actionable templates, and introduces an AI-powered tool for automating competency-based interviews.

1. The Pitfalls of Traditional Interviews

2. The Need for a Structured System

3. Identifying Core Competencies

4. Defining Proficiency Levels

5. Formulating Effective Questions

6. Writing Competency-Based Questions

7. Developing a Scoring Framework

8. Making the Hiring Decision

Free AI-Powered Interview Question Builder: Automatically extracts competencies from job descriptions and generates interview questions and rubrics based on the framework I discussed on the podcast.