Networking doesn't have to mean awkward events or forced small talk. In this episode, Diana sits down with Greg Roche to break down a practical, low-pressure approach to building meaningful professional relationships especially for introverts.

• Rethinking what "networking" actually means

• Why traditional networking advice doesn't work for introverts

• How Greg built his approach after being laid off

• Using "dormant ties" to restart your network

• Why being "easy to help" matters more than being impressive

• The power of specificity in asking for help

• How to describe what you do so people remember and refer you

• Why adjacent connections matter more than direct ones

• Simple outreach strategies that actually get responses

⏳ Timestamps 01:03 Meet Greg Roche and his background 03:16 Getting laid off and realizing the importance of networking 04:56 Rethinking networking for introverts 07:00 Early career experiences and hidden networking 12:05 Introversion, energy, and communication style 14:09 Learning to lead conversations through better questions 18:07 What networking is (and isn't) 23:21 Why imagination matters in job search networking 26:29 How to make it easy for people to help you 29:10 Why vague asks don't work 32:14 Building and using a target company list 35:14 Giving people the words to describe you (the "memory dart") 38:59 Dormant ties: where to start networking 43:08 How to reach out and restart conversations 48:28 What to say in your first message

Resources Mentioned

• The Fast and Easy Guide to Networking for Introverts by Greg Roche→ https://www.amazon.com/Fast-Easy-Guide-Networking-Introverts/dp/B08MTZ8T85

• Greg's Substack: The Introverted Networker → https://gregroche.substack.com

• Adam Grant's Give and Take → https://adamgrant.net/book/give-and-take/

💡 Take Action 🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Greg Roche 🌐 Website → https://gregroche.com 📬 Substack → https://gregroche.substack.com 🔗 LinkedIn → https://www.linkedin.com/in/gregroche

📲 Follow Me LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

What happens when you stop waiting for permission and start betting on yourself? Diana sits down with Kenny Booth to explore his unconventional path into tech, entrepreneurship, and landing a role at his dream company. If you've ever hesitated to take a risk, this episode will challenge how you think about failure and opportunity.

• Kenny's nontraditional path into tech and business intelligence

• Turning curiosity and side projects into career opportunities

• Why failure and risk-taking are essential to growth

• Entrepreneurship: who it's for (and who it's not)

• The difference between reasons and excuses

• Why pedigree matters less than impact

• The mindset required to bet on yourself

⏳ Timestamps 01:00 Kenny's journey to landing his dream job at Disney 03:00 How podcasting started during the pandemic 05:30 Creating your own "paradise" through mindset shifts 08:30 Growing up with Disney and early influences 11:00 From stockbroker dreams to tech curiosity 13:00 Discovering automation and problem-solving through macros 15:30 Breaking into software engineering without a traditional path 18:00 Early entrepreneurial experiments (including childhood ventures) 23:00 Starting Code Blue and taking the first leap 25:30 Where confidence and willingness to fail comes from 30:00 Entrepreneurship: who should (and shouldn't) pursue it 32:30 Reasons vs. excuses — a critical mindset shift 34:00 The energy required to succeed in entrepreneurship 36:00 Why pedigree doesn't equal success 38:00 The downside of self-motivation and internal pressure 40:30 Balancing side business with corporate work 42:00 Taking risks, making pivots, and betting on yourself

💡 Take Action 🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away from your job? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Kenny Booth 🔗 LinkedIn → https://www.linkedin.com/in/kennethboothjr/

📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

In this milestone 50th episode, Diana reconnects with Angie Callen to explore how confidence is built through action not before it. They unpack the realities of entrepreneurship, creative risk-taking, and how embracing imperfection leads to meaningful growth in both work and life.

⏳ Timestamps 01:00 Meet Angie Callen & her new book 03:00 Confidence through action vs. perfection 07:00 The trap of over-implementation vs. overthinking 10:00 Podcast growth: lessons from 0 to 50 and beyond 15:00 Why consistency matters more than perfection 20:00 The real ROI of podcasting: relationships & community 24:00 From Sunday Scaries to life by design 28:00 The mindset shift: default life vs. intentional life 32:00 Confidence is built by doing, not waiting 36:00 Using physical challenges to build mental resilience 40:00 Letting go of control and the illusion of certainty 44:00 Worrying as a false sense of control 48:00 AI, business, and staying human in a tech-driven world 52:00 Delegation, automation, and the future of work

💡 Take Action 🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away from your job? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Angie Callen 🌐 Website → https://careerbenders.com🔗 LinkedIn → https://www.linkedin.com/in/angiecallen 📘 Facebook → https://www.facebook.com/careerbenders/# 📸 Instagram → https://www.instagram.com/careerbenders/ 📸 Instagram → https://www.instagram.com/angieonanadventure/ 🧵 Threads → https://www.threads.com/@angieonanadventure

📲 Follow Me LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

In this episode of Work Should Feel Good, Diana sits down with product leader and consultant Michael Hirsch to explore what real product leadership looks like, especially as AI reshapes how product teams work. They discuss the difference between product management and product leadership, why most companies fail to prepare new leaders, and how AI can free product managers from tactical work so they can focus on strategic thinking.

• Michael's journey from working in his father's business to leading product teams in tech

• Why the transition from product manager to product leader is so difficult

• The difference between product management and product leadership

• Common mistakes new product leaders make

• Why organizations rarely train leaders effectively

• Tactical vs strategic product work (and why most teams get it wrong)

• How AI can free product managers from busywork

• Why the best product leaders prioritize developing their teams

• The hidden political dynamics inside product roles

⏳ Timestamps 02:18 The story behind "Break a Pencil Consulting" 05:54 Growing up in the family business and deciding to leave 13:30 Career uncertainty, layoffs, and betting on yourself 18:59 Why Michael moved into leadership coaching 22:02 Why the transition from product manager to leader is so difficult 26:34 Product managers vs engineering managers 30:11 Why product and project management should not be the same role 33:40 The problem with how companies define product management 39:56 Strategic vs tactical work in product roles 46:00 How AI can free up time for strategic thinking 51:30 What strong product teams do differently with AI

💡 Take Action

🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Michael Hirsch

🌐 Website → https://www.breakapencil.com🔗 LinkedIn → https://www.linkedin.com/in/mhirsch/ 📺 YouTube → https://www.youtube.com/@Break-a-Pencil 📧 Newsletter → https://breakapencil.beehiiv.com

📲 Follow Me On Social Media

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What actually makes workplace change succeed or fail? In this episode, Diana sits down with Lisa Riegel to break down how brain science, leadership behavior, and systems thinking all play a role in creating sustainable change at work.

• Why most leadership advice stays too conceptual and how to make it operational

• The difference between outcomes vs. outputs (and why it matters for burnout)

• How workplace culture is shaped by actions, not stated values

• The 8C Commitment Framework for leading change effectively

• Why people resist change (and what's actually happening in the brain)

• The role of identity, fear, and perceived loss in workplace resistance

• How to structure meetings for clarity, engagement, and better decisions

• The four types of conversations leaders must understand

• Coaching strategies based on willingness and ability

• Using AI and automation without losing the human element

⏳ Timestamps 01:00 Lisa's unconventional career path and pivot into leadership and brain science 05:30 From education to leadership coaching and organizational transformation 09:45 Outcomes vs. outputs—and why leaders get this wrong 13:30 Culture, belonging, and the foundation for successful change 16:00 The 8C framework: clarity, coherence, and cadence 20:15 Why leaders struggle to translate vision into action 23:00 How people experience change differently (and why timing matters) 26:30 Structuring meetings: directives, dialogue, discussion, and data debriefs 31:30 Decision-making, consensus, and accountability in teams 36:00 Coaching through resistance: able vs. willing employees 41:30 Identity, fear, and why people resist change 46:00 AI, workplace anxiety, and the future of human skills 49:30 Practical example of improving systems and workflows

💡 Take Action

🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away from your job? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Lisa Riegel

🌐 Website → https://lisariegel.com🔗 LinkedIn → https://www.linkedin.com/in/lisariegel/

📲 Follow Me

LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

Diana sits down with Jennifer Brussow, VP of Data, to explore how AI is reshaping hiring, leadership, and product development. They unpack the real-world implications of generative AI, what it means for job seekers, and how technical leaders are adapting in real time.

• How AI is changing hiring processes and candidate evaluation

• Why networking matters more than ever in a high-volume application market

• What hiring managers actually look for in AI-assisted technical work

• The balance between innovation and risk in AI implementation

• Bridging communication gaps between technical and non-technical teams

• Jennifer's unconventional path from English to data leadership

• The role of psychometrics in assessment and hiring decisions

• How product, data, and leadership priorities can conflict—and align

⏳ Timestamps

00:00 Intro and Jennifer's background 02:00 Personal branding and AI policy thinking 05:30 Wine, LinkedIn, and unconventional signals 09:30 From English major to data leadership 14:00 What psychometrics actually is 20:00 Product vs. data: tension and collaboration 27:00 Ethics, risk, and high-stakes assessment 31:00 AI in product development and business decisions 36:00 How AI is changing hiring at scale 42:00 What hiring managers look for in AI-assisted work

💡Take Action

🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Jennifer Brussow

🌐 Jennifer Brussow → https://www.jenniferbrussow.com/ 🔗 LinkedIn → https://www.linkedin.com/in/jennifer-brussow/

📲 Follow Me On Social Media

LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

This roundtable conversation breaks down what job seekers are getting wrong in today's market and how to approach your search more strategically. Diana Alt, Angie Callen, and Scott Gardner share practical insights on clarity, networking, and what actually works right now.

• Why "busywork" is sabotaging your job search

• The role of clarity in targeting the right opportunities

• Product-market fit and how to position yourself effectively

• Why mass applying and generic networking don't work

• The truth about ATS, tailoring, and resume myths

• How to think about qualifications in a competitive market

• What effective networking actually looks like in 2026

• Balancing online applications with relationship-driven strategies

• How long a job search realistically takes today

⏳ Timestamps

00:00 Intro & context for this special panel episode 01:11 Why job seekers are "scaling nonsense" 03:35 The hidden cost of lack of clarity 06:48 Thinking like a marketer (and a product) 10:07 Market research and staying ahead of job postings 12:04 Are online applications a waste of time? 16:47 Resume myths: ATS, tailoring, and metrics 21:40 How qualified do you really need to be? 26:56 The stoplight method for assessing fit 32:32 What to do first if you had to job search today 36:50 What effective networking looks like now 45:00 How long it actually takes to land a role

💡 Take Action

🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away from your job? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Scott Gardner

🌐 Vitae Express → https://www.vitaeexpress.com/🔗 LinkedIn → https://www.linkedin.com/in/scott-gardner-cprw/

Diana sits down with Eric Nehrlich to explore how embracing personal agency can help you navigate burnout, rethink career expectations, and create more meaningful impact at work. This episode unpacks the hidden costs of chasing success and how reclaiming choice can transform your career.

• The concept of personal agency and why it matters in your career

• How burnout develops—even in high-achievement environments

• The hidden dangers of chasing promotions you don't actually want

• Why doing work that drains you accelerates burnout

• The role of leadership and business understanding in career growth

• How to evaluate trade-offs and make intentional career choices

• Reframing "being stuck" into active decision-making

• The importance of accepting consequences to unlock real choice

⏳ Timestamps 02:00 Eric's background: from physics to tech and leadership 06:30 Music, STEM, and blending skills in teams 10:00 Transitioning from engineering to business and leadership 15:30 Learning the importance of understanding the money 20:00 Becoming a translator between technical and executive teams 24:30 Chief of Staff role and impact at Google 30:30 Burnout story: working 100-hour weeks 34:00 When the "next promotion" isn't actually worth it 38:00 The moment of realizing you have a choice 42:00 Accepting consequences and reclaiming agency

💡 Take Action 🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away from your job? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Eric Nehrlich 🌐 Website → https://www.toomanytrees.com🔗 LinkedIn → https://www.linkedin.com/in/nehrlich/

📲 Follow Me LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

What actually happens behind the scenes in recruiting? In this episode, Diana Alt sits down with Kelli Hrivnak, founder of Knak Digital, to unpack how recruiting really works from sourcing candidates to the business model behind recruiting firms. If you've ever wondered how recruiters evaluate candidates or why the hiring process can feel confusing, this conversation pulls back the curtain.

• The difference between internal recruiters and agency recruiters

• How recruiters are measured and how recruiting firms make money

• What "sourcing" actually means in modern recruiting

• What makes a candidate easier for recruiters to find and evaluate

• How mass applications and auto-apply tools are affecting hiring

• Signals recruiters look for that suggest someone may be open to a new role

• The reality of backdoor references and reputation management

• The controversy around reverse recruiting services

⏳ Timestamps 01:00 Kelli's unconventional path into recruiting (restaurant management and wine sales) 05:00 Nonlinear career paths and mid-career reassessment 09:10 Internal recruiters vs. agency recruiters explained 12:00 How internal recruiters are measured (time-to-fill and sourcing metrics) 14:20 How agency recruiters make money and how recruiting fees work 18:00 Contract recruiting, markups, and how staffing firms operate 23:10 What a "full desk recruiter" is 25:40 What sourcing means and how recruiters actually find candidates 30:00 How candidates can make themselves easier to find 32:10 Why hard skills and industry keywords matter in recruiter searches 34:20 How mass applying and auto-apply tools are changing hiring 39:00 Signals recruiters use to identify candidates who may be open to change 41:20 Backdoor references: what they are and why companies use them 47:30 Reverse recruiting and why it's controversial 52:00 Job search shortcuts vs. doing the work that actually matters

💡 Take Action

🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away from your job? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Kelli Hrivnak

🌐 Knak Digital → https://www.knakdigital.com🔗 LinkedIn → https://www.linkedin.com/in/kellihrivnak/

📲 Follow Me

LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

Bosky Mukherjee shares her journey from corporate executive to founder of SheTrailblazes and explains what truly differentiates high-performing functional leaders from business operators. They discuss commercial fluency, executive presence, sponsorship, burnout, entrepreneurship, and what it means to build a career that works on your terms.

If you're aiming for senior leadership or considering building your own path, this episode offers practical insight into what it really takes to be seen, sponsored, and strategically positioned.

• Why commercial fluency is non-negotiable for senior leadership

• The identity shift from functional leader to business operator

• Mentorship vs. sponsorship and why women need both

• Building influence in male-dominated executive environments

• Moving between corporate leadership and entrepreneurship

• Designing work that aligns with life and long-term fulfillment

⏳ Timestamps

00:00 Intro and guest introduction 04:10 Early career pivots and entrepreneurial experiments 12:15 Developing commercial fluency inside corporate 19:40 Executive communication and the director-level shift 28:20 Mentors vs. sponsors — what actually drives promotion 37:05 Women, power dynamics, and executive influence 46:10 Entrepreneurship, identity, and building your own table 55:30 Final thoughts on ambition, flexibility, and fulfillment

💡Take Action 🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt 📖 Grab my Resume Don'ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it's time to walk away? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com 📢 Connect with Bosky Mukherjee 🌐 SheTrailblazes → https://www.shetrailblazes.com/ 🔗 LinkedIn → https://www.linkedin.com/in/bosky/ 📲 Follow Bosky on Social Media: Instagram → https://www.instagram.com/boskymukherjee TikTok → https://www.tiktok.com/@bosky_mukherjee

📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt