Drinks After Work with Shannon and Deb

By Shannon Tipton

Ever wonder what your colleagues really talk about when they're off the clock? Welcome to Drinks After Work, where Shannon Tipton and Deborah Harris pull up a stool for the kind of straig

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FAQs about Drinks After Work with Shannon and Deb:

How many episodes does Drinks After Work with Shannon and Deb have?

The podcast currently has 24 episodes available.

Drinks After Work with Shannon and Deb episodes:

May 01, 2026Toxic Boxes and Temper Tantrums
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!

This time, we're talking all about:
The toxic boss profiles you'll recognize immediately (the temper-tantrum thrower, the spotlight hog, the gaslighter, the rule-maker)
Triangulation — when your boss talks about you instead of to you
How toxic bosses are literally making employees sick (it's not just stress, it's chronic health damage)
Why HR's "engagement surveys" are missing the point entirely
The waterfall effect of bad bosses creating more bad bosses
How to protect yourself when you're stuck under one

In this episode, Shannon and Deborah break down the science (and the pettiness) behind toxic bosses. The article they reference says 75% of workers think their boss is the most stressful part of their workday — and that stress doesn't stay at work. It follows you home, wrecks your weekends, and shows up in your body. They share their own war stories with triangulation, gaslighting, write-ups built on twisted conversations, and bosses who demand spotlight while making you do their work. But this isn't just a vent session — they get into how to actually protect yourself: document everything (on a personal device), bring facts over feelings, and don't go in hot unless you've got another gig in the shadows.

So sip, swig, or chug — and get ready to:
Recognize the toxic boss profiles before they wreck your health
Document everything on a personal device (not the work computer)
Lead with facts over feelings when escalating to HR
Throw their own expectations back at them when they don't follow their own rules
Take advantage of ethics hotlines and anonymous reporting if you have them
Protect your mental and physical health — this is a ripple effect

Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Deborah: Cooper's Hawk Moscato — Floral, sweet, with hints of peach, melon, and orange blossom.
Shannon: Classic Mojito — Rum, lime, mint, sugar, and a few pieces of fresh fruit for spring.

Find all our drink recipes and more at our website.

Resources:
Forbes: Toxic Bosses Are Making Employees Sick—And The Evidence Is Impossible To Ignore
Harvard Business Review: Stop Making Excuses for Toxic Bosses
Workplace Assessments -
Korn Ferry
McKinsey
Gallup

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Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
39min
April 17, 2026Balloon Brags and Broken Trust
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!
This time, we're talking all about:
The trust recession — why trust is broken everywhere (workplace, brands, insurance, you name it)
How layoffs during record profits have destroyed employee trust
Why loyalty means nothing anymore (on both sides of the counter)
The connection between technology, AI, and the erosion of human trust
Why relationships at work matter more than ever
How to rebuild trust one small interaction at a time
In this episode, Shannon and Deborah dive into the trust recession that's eroding the workplace, customer relationships, and pretty much every institution we used to rely on. When CEOs are pulling in 12 figures while laying off thousands, when insurance companies want to put trackers on your car but still raise your rates, when layoffs happen during record profits — trust breaks. And once it breaks at work, it bleeds into everything else. But it's not all doom and gloom. They share how to rebuild trust incrementally, from speaking up for people in their absence to bringing an extra donut to the coworker next to you.
So sip, swig, or chug — and get ready to:
Recognize the signs that your company's "we're a family" talk is BS
Stop expecting loyalty from organizations that don't give it back
Take the first step in building real workplace relationships
Speak up for people when they're not in the room
Shop your insurance every few years (loyalty doesn't pay)
Trust first until you can't — but know when you can't
Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Shannon: Lemon Drop — Classic lemon drop, hold the sugar on the rim.
Deborah: Trust Issues — Vodka, watermelon juice, lime juice, and a little agave syrup.

Find all our drink recipes and more at our website.

Resources:
Forbes: "The Trust Recession: Why Trust and Customer Experiences Are Failing"

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
30min
April 03, 2026The Pool's Empty and Betty Sue's Giving The Ick
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!

This time, we're talking all about:
Power dynamics at work — from Betty Sue in finance to team leads on power trips
When to leave corporate America and go out on your own
The ick of entrepreneurship: trading one set of problems for another
The harsh realities no one tells you (spoiler: healthcare costs will make you cry)
Why the system wasn't built to support entrepreneurs — and how to survive anyway
How to know if you're built for the solo life (and what to do if you're not)

In this episode, Shannon and Deborah dive into the messy reality of leaving corporate America to start your own business. It sounds amazing when you're sitting in your corporate chair collecting a corporate paycheck, but then you realize you're just trading one set of problems. They break down the things nobody warns you about — healthcare costs that want it all upfront, business insurance requirements, wearing every single hat, and the scam artists promising you can make $5 million in a year if you just buy their course. But it's not all doom and gloom — they also share real resources and remind you that failing forward is part of the process, whether you're in corporate or on your own.

So sip, swig, or chug — and get ready to:
Recognize power dynamics before they bite you in the @$$
Know your strengths and weaknesses before you jump ship
Find free resources through the Small Business Association and community colleges
Shop around for the right networks (and don't be afraid to leave the wrong ones)
Stop trying to perfect everything — it's an iterative process
Remember that going back to corporate doesn't make you a failure

Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Deborah: Rise Mushroom Coffee — With almond milk and sugarcane sugar.
Shannon: Starbucks Black Coffee — Plus donuts, because sometimes you just need the comfort food of all comfort foods.

Find all our drink recipes and more at our website.

Resources:
Small Business Administration
Chicago Small Business Expo

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
36min
March 19, 2026Work Family and...Bonus Hams?
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!

This time, we're talking all about:
Corporate swag vs. actual bonuses (spoiler: we want the money, not the blanket)
Why "we're all family here" is a giant red flag in job postings
Workplace favoritism and the halo effect — when one person can do no wrong
The Peter Principle: promoting people until they're incompetent
When entire departments become the favorites (looking at you, Sales)
How to survive (and maybe thrive) when you're not the chosen one

In this episode, Shannon and Deborah tackle the toxic "we're all family here" culture, workplace favoritism and the halo effect, the Peter Principle in action, and department favoritism where Sales gets golf trips while you fill out a PO for a pencil. But it's not all doom and gloom — they share strategies for surviving when you're not the favorite, from cross-department collaboration to the "ask forgiveness instead of permission" approach, and remind you to hold onto the real workplace relationships that actually matter.

So sip, swig, or chug — and get ready to:
Recognize the red flags of favoritism and fake family culture
Figure out how to collaborate across departments to become the next favorite (or at least get noticed)
Remember: don't let workplace dysfunction bleed into your personal life
Hold onto the real relationships you build at work — those people will advocate for you in rooms you're not in

Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Deborah: Cherry Picking — Vodka, elderflower liqueur, fresh lime juice, simple syrup, soda water. Garnish with cherry or mint.
Shannon: Jazzy — Vodka, Disaronno, orange liqueur, orange juice, fresh lemon juice. Shake well and serve straight up, super cold.

Find all our drink recipes and more at our website.

Resources:
The Peter Principle (because promotions aren't always progress)

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
27min
March 04, 2026PTO, Shame and Hot Dogs
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!
This time, we're talking all about:
Why unlimited PTO is actually an illusion of flex
PTO shame and why we hoard our time off like it's precious (because it is)
The unspoken rules that make taking time off feel like a crime
How working from home makes PTO guilt even worse
Planning, scheduling, and actually honoring your time off

In this episode, Shannon and Deborah are joined by special guest Chris Coladonato (aka the Connection Catalyst) to tackle the complicated world of paid time off. From companies that give you PTO then punish you for taking it, to the culture of answering emails at 9 PM that trains everyone to disrespect boundaries, they break down why we're all exhausted and what we can actually do about it. Plus, some surprisingly strong feelings about hot dogs.

So sip, swig, or chug — and get ready to:
Stop teaching people you're always available (put down the work phone)
Plan time to decompress after your vacation ends
Set up coverage plans before you leave (so you don't feel guilty)
Write an out-of-office that actually protects your inbox
Honor your time off instead of just scheduling it

Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Deborah: Out of Office — Coconut rum, pineapple orange juice (basically a piña colada for PTO vibes).
Shannon: Maple Bourbon Smash — Bourbon, maple syrup, orange juice, lemon juice, bitters, muddled with orange slices.
Chris: Guinness Zero (or Athletic Brewing Irish Stout) — Non-alcoholic beer for pretend time off.

Find all our drink recipes and more at our website.

Resources:
Chris Coladonato, the Connection Catalyst

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
36min
February 11, 2026Phony Book Deal and Corporate Squid Games
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!
This time, we're talking all about:
Why forced team building exercises make everyone scatter like roaches
The difference between building culture and forcing "fun"
Stay interviews vs. exit interviews (and why timing matters)
When the CEO thinks they're everyone's buddy (spoiler: they're not)
How to survive mandatory team building when you'd rather be anywhere else
In this episode, Shannon and Deborah tackle the dreaded corporate team building exercise—from rope courses nobody asked for to virtual activities that somehow make it worse. They break down why these forced bonding sessions often backfire, what leaders get wrong about culture, and how knowing your team's actual needs (through stay interviews, not mandatory fun) makes all the difference. Plus, they share survival tips for when you're stuck doing trust falls against your will.
So sip, swig, or chug — and get ready to:
Learn what stay interviews are and why they beat exit interviews
Understand why series beats events for building real trust
Create your own team building moments (with people you actually like)
Make the best of it when you can't escape the corporate games
Recognize when leadership is too disconnected to plan effectively
Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Deborah: The Halo Effect — Half ounce of gin, peach liqueur, lime juice, orange bitters, topped with Prosecco and garnished with a flower.
Shannon: Shaken Daiquiri — Bacardi, lime juice, simple syrup, shaken (not frozen) with extra lime for tartness.

Find all our drink recipes and more at our website.

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
24min
January 28, 2026Badges and Betrayals
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!
This time, we're talking all about:
Coffee Badging: The office protest you didn't know had a name
Revenge Quitting vs. Quiet Quitting: When employees fight back (loudly or silently)
Rage Applying: Blanketing the internet with your resume out of pure frustration
Quiet Firing: When your company makes you so miserable you quit on your own
Why all of these "trends" are really just symptoms of broken workplace culture

In this episode, Shannon and Deborah dive into the buzzwords taking over workplace conversations—from coffee badging (swipe in, grab coffee, bounce) to revenge quitting (bringing your whole crew with you when you leave). They break down why employees are resorting to these tactics, what signs to watch for if you're being quietly fired, and how to protect yourself when the workplace turns toxic. Plus, some real talk about blind spots, equity vs. fairness, and why documentation is your best friend.

So sip, swig, or chug — and get ready to:
Recognize the signs of quiet firing before it's too late
Document everything (yes, screenshots count)
Start "quiet learning" on the company dime while you still can
Build your portfolio and LinkedIn testimonials before you need them
Know when to walk away—and bring your people with you

Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Shannon: Hot Apple Cider with Bourbon — Apple cider simmered with chunked apples, chunked oranges, and cinnamon sticks until reduced, then mixed with bourbon.
Deborah: Pear Pressure — Vodka, spiced honey syrup, apple cider, lemon, topped with Prosecco.

Find all our drink recipes and more at our website.

Resources:
Fortune Magazine: Farewell, quiet quitting. 2025 could be the year of ‘revenge-quitting’

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
49min
January 16, 2026Performance Reviews: The Corporate Hunger Games
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work!
This time, we're talking all about:
Why performance reviews feel like going to the principal's office
How the rating system is rigged (spoiler: you're never getting that 5/5)
The disconnect between widget-based work and knowledge-based work
Why managers wait until the last minute and copy-paste from last year
What to do instead if you want actual feedback that matters
In this episode, Shannon and Deborah dig into one of corporate America's most dreaded rituals: the annual performance review. From canned responses and forced rankings to managers who "never give out a 10," they break down why this outdated system leaves 80% of employees feeling uninspired and unappreciated. But they don't just vent—they also share practical advice for both managers and employees on how to make feedback meaningful, timely, and actually useful.
So sip, swig, or chug — and get ready to:
Stop waiting until review time to give (or get) critical feedback
Learn how to care personally while challenging directly (thank you, Kim Scott)
Ask the right questions during job interviews to avoid toxic review cultures
Use one-on-ones for coaching instead of just project updates
Understand what "good" looks like before you're judged on it
Because it wouldn't be Drinks After Work without the drinks, here are the FAB:
Shannon: Hot Apple Cider with Bourbon — Apple cider simmered with chunked apples, chunked oranges, and cinnamon sticks until reduced, then mixed with bourbon.
Deborah: Pear Pressure — Vodka, spiced honey syrup, apple cider, lemon, topped with Prosecco.

Find all our drink recipes and more at our website.

Resources: Performance Reviews Are Pointless and Insulting: Why Do They Still Exist? (Forbes, 2018)
Radical Candor by Kim Scott
Psychology Today: Less than 20% of employees feel inspired by their review (2024)
Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
43min
January 12, 2026Emotional Support Animals and Smart @$$ Goals
Pop the tab on something cold and settle in — it's time for another round of Drinks After Work, 2026 Edition!

This time, we're talking all about:
Why New Year's resolutions set us up for failure (and what to do instead)
How SMART goals aren't actually that smart for personal growth
The perfectionism trap that makes goal-setting feel like punishment
Why reflection beats resolution every time
Practical alternatives that actually work (hello, ALIGN goals)

In this episode, Shannon and Deborah kick off 2026 with some real talk about why we keep setting ourselves up for disappointment every January. From SMART goals that fight against themselves to New Year's resolutions built on where we've failed, they break down why the traditional approach leaves us feeling like crap by January 5th. But it's not all doom and gloom—they share practical frameworks that focus on progress, self-compassion, and chunking big dreams into doable steps.

So sip, swig, or chug — and get ready to:
Ditch the guilt and perfectionism around goal-setting
Learn the "Big Rock" chunking method for breaking down goals
Discover ALIGN goals (Aspire, Live it, Integrate, Gauge, Nurture)
Give yourself emotional grace instead of another reason to feel guilty
Turn mandatory SMART goals into SMART ASS goals (yes, really)

Because it wouldn't be Drinks After Work without the drinks, here are the FAB picks:
Shannon: Grapefruit Fizz — Fresh grapefruit juice, rosemary sugar syrup, and club soda for that Dry January vibe.
Deborah: Resolution Refresher — Cranberry juice, lime, elderflower syrup, and sparkling water with frozen cranberries.

Find all our drink recipes and more at our website.

Resources:
Why SMART Goals Don't Work

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
29min
November 26, 2025Human Resources or Human Roadblocks?
Drinks After Work with Shannon Tipton and Deborah Harris: Where’s the Human in HR?

Pop the tab on something cold and settle in — it’s time for another round of Drinks After Work! This episode goes straight into the tension between people and policy, asking: when did human resources stop being about the humans?

This time, we’re talking about:
What happens when HR becomes more about protecting the company than the people
Why surveys and “great place to work” badges aren’t always what they seem
How trust is broken—and what it takes to rebuild it
Why marginalized employees often face the worst of HR’s shortcomings
What HR professionals can actually do to be human-centered again

From performance improvement plans disguised as betrayal to the illusion of open doors and “employee engagement,” Shannon and Deborah get candid about their own experiences with HR. But it’s not just about calling things out—it’s about exploring what a more authentic, people-first approach could look like.

So grab your drink, tune in, and get ready to:
Rethink the role HR plays in your org’s culture
Explore what people really want from workplace support systems
Consider how L&D and HR can (and should) work together
Walk away with simple, practical steps—whether you’re on the team or just surviving it

Because it wouldn’t be Drinks After Work without the Happy, here are our Frosty Adult Beverage (FAB) picks:

Deborah: Raspberry Sangria – Fruity, punchy, and honest to a fault.
Shannon: Frozen Espresso Martini – A Bon Appétit gem with brunch-level boldness.

Find all our drink recipes and more at our website.

Resources:
HR Trends: How to Build a Human-Centric Culture in 2024

Be part of the Learning Rebels Community.
Continue the conversation while building connections and capability. Learn more here.

Join the Coffee Chat conversations
Be part of Learning Rebels live Coffee Chat Discussions! Sign up here.

Hire Learning Rebels.
When you need learning that sticks, we’ll fight to make performance results happen. Visit the Learning Rebels website to learn more.

Hosts: Shannon Tipton & Deborah Harris

Podcast produced by: Obsidian Productions
...more
34min

FAQs about Drinks After Work with Shannon and Deb:

How many episodes does Drinks After Work with Shannon and Deb have?

The podcast currently has 24 episodes available.