Corporate Strategy

40 Episodes
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By: The Corporate Strategy Group

Satirical self-help lovingly shared by two millennial tech industry vets. Engineering, sales, marketing, product management, and custodial services cover it all in 30 minutes or less. Coffee not provided.

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Strategy Is Medicine
#37
Yesterday at 4:00 PM


We bring Brooklyn Jones back as our first on-camera guest and unpack why the word strategy makes smart people groan, then map the real issue to trust and plain-English leadership. We also draft the worst meeting formats and leave with practical scripts for getting strategic work done without triggering the eye roll.

• Brooklyn’s life updates and graduating back into entrepreneurship 
• The top “worst meetings” draft and why they drain teams 
• Strategy as medicine and why people resist it 
• Trust and shame as the hidden blockers behind “execution problems” 
• Goals versus strategy and why...


Working With People You Cannot Stand Part 2
#36
10/05/2026

We roll from a chaotic vibe check into a pile of “I just can’t” workplace moments that perfectly explain why the week feels brutal. Then we get practical about using AI to stay afloat and about handling toxic coworkers you depend on without sacrificing your time, energy, or reputation. 
• our top “I just can’t” triggers at work 
• why stress shows up in sleep, migraines, and burnout 
• using Claude to save time and push through stuck tasks 
• keeping a human in the loop to prevent AI mistakes and rework 
• the cross team dependency problem when you need “Jerm...


Working With People You Cannot Stand Part 1
#35
09/28/2026

We trade stories about the coworkers who make progress feel impossible, from perfection-first gatekeepers to senior dependencies who weaponize silence. We walk through practical ways to escalate without drama, protect delivery, and recognize when leadership is the real problem. 
• breaking down why some weeks feel like nonstop Wednesday 
• defining levels of “can’t stand working with them” from annoying to unbearable 
• sharing an MVP vs perfection conflict that nearly turns physical 
• explaining why leadership often protects toxic high performers 
• escalating with facts, notes, and low-emotion framing 
• using managers as “heavy guns” to force decisions 
• handling ad...


Do Not Microwave Fish Ever Again
#34
09/14/2026

We draft our way through the most relatable corporate annoyances, from out of office messages that help to video calls that should have never happened. Along the way, we rant about work travel, office microwaves, and the small tech failures that can derail a meeting in seconds.

• Patreon plug for storytelling and presentation skills using the Hero’s Journey and the Amazon method 
• Why business travel lingers in your brain and why flying feels uniquely miserable 
• The case that incentives and regulatory capture keep travel and other systems worse than they need to be 
• Nostalgia mar...


Real Collaboration Is Rare
#33
09/08/2026

We challenge the way workplaces use “collaboration” and argue that most of it is just independent work with a shared deadline. We map out what real collaboration looks like, why it’s rare, and how to avoid meetings that waste time and strip teams of autonomy. 
• production issues, missing audio, and why last week only lives as shorts 
• a mini crusade against LinkedIn AI slop and the idea of reporting 10 posts a day 
• the cheese ball obsession and why it somehow becomes a lifestyle 
• “collaboration” versus task handoffs, plus the group project origin story 
• doers, detractors, and th...


The Executive Detail Trap
#32
08/24/2026

We go from our love of surprise twists to a brutally practical question: how we deliver the right level of detail at work when leaders give vague asks and unclear formats. We share the tactics we use to get fast feedback, avoid wasted effort, and navigate the executive layer without losing our minds. 
• why surprises and subverted expectations work in stories and advertising 
• how trust breaks when companies reverse public promises 
• the real problem with ambiguous asks for decks, emails, and RCA summaries 
• asking individual contributors directly for the details that matter 
• giving executives three options s...


Decisions In A Vacuum
#31
08/17/2026

We start with some intentionally ridiculous market talk, then get honest about how corporate meetings can reward confidence over clarity. We break down what to do when leadership makes decisions in a vacuum, and how we protect our teams while still surviving the politics. 
• spotting “corporate nonsense” language and why quiet people often add more value 
• using AI for real work, including document review systems and Jira automation lessons 
• defining vacuum decisions through impact and breakage, who gets hurt and who doesn’t 
• staying positive without becoming the future scapegoat, asking questions as CYA 
• choosing tactics base...


Audio Exclusive: The Career What-Ifs
#30
08/10/2026

We test a new recording setup, nerd out on an electronics repair game, then use it as a springboard to talk about right to repair and why fixing things feels harder in the US than it should. We also run a career retrospective on our biggest pivots, what we might have done differently, and why fulfillment often beats the “safe” path. 
• trying a new podcasting platform and accepting the risk of a messy test 
• a Tokyo repair shop game that captures the joy of tinkering without the wait 
• why parts access and repair markets shape consumer behavior and...


Corporate Hot Takes On Email Boundaries And Real Productivity
#29
08/02/2026

We catch up live from a newly sound-treated studio and somehow end up deep in toe injuries, travel gear, and why Crocs might be the real comfort hack. Then we pivot into corporate hot takes on email habits and productivity, including why living in your inbox keeps you reactive and why “busy” is not the same as effective.

• joking about LaCroix as a “fountain of youth” and settling into the live setup 
• adjusting to a soundproof room and the oddly echo-free feeling 
• post-vacation check-in with IBS, broken toes, hiking pain, and black toenails 
• why Crocs feel wrong bu...


Strategy vs Tactics
#28
07/27/2026

We trade vacation stories and a surprisingly business-relevant take on Moby Dick, then pivot into the career trap of becoming the workplace firefighter. We unpack how the Five Whys, smarter follow-ups, and simple systems help us protect our time, avoid burnout, and grow into more strategic roles without losing credibility. 

• why being the go-to fixer feels rewarding then becomes a trap 
• using the Five Whys to find root causes instead of treating symptoms 
• when to execute immediately and when to push for context 
• turning tactical delivery into strategic influence with follow-up conversations 
• a practical way t...


AI Job Loss Reality Check
#27
07/22/2026

AI job loss is real in some corners and wildly exaggerated in others, so we sort the headlines from what companies can actually implement without breaking everything. We map the roles most exposed to automation, why the AI service model may hit an ROI wall, and how to protect your career by owning the tool instead of ignoring it. 
• AI anxiety shows up everywhere now, even outside tech 
• Net job growth vs hidden disruption across industries and age groups 
• Ghost job postings and why job numbers can mask real pain 
• Roles most at risk: clerical, admin, routi...


How To Get Promoted
#26
07/13/2026

We go from CAPTCHA conspiracies and AI slop on LinkedIn to the deeper problem of algorithm-driven feeds that ignore human boundaries and fry our attention. Then we get practical and a little spicy about corporate promotions, career leverage, and why you have to say what you want out loud if you expect anyone to help you get there. 

• CAPTCHA as hidden training data and what modern image prompts imply 
• Why LinkedIn feels worse after AI and why scrolling is not neutral 
• Community-based feeds versus algorithm-driven feeds and why boundaries matter 
• Heat exhaustion recap, hydration basics, and...


Icebreakers That Actually Work
#25
07/07/2026

We mess up our production setup, vent about being hard to find on YouTube, then pivot into a surprisingly practical conversation about building real connection on remote teams. A ridiculous food debate becomes our blueprint for icebreakers that boost engagement without crossing personal boundaries. 
• losing the OBS profile and rebuilding the show setup from scratch 
• struggles with discoverability on YouTube and experimenting with shorts on LinkedIn, Instagram, and YouTube 
• a real heat exhaustion scare and what dehydration can feel like 
• electrolytes, salt, and the pickle juice “shot” as a recovery trick 
• why remote work culture needs inten...


Figuring Out Corporate
#24
06/30/2026

Corporate work is less about having the perfect skill set and more about staying curious while you translate people’s wants into real outcomes. We argue that nobody has it all figured out, so the winners are the ones who keep trying, measuring, and adapting without taking every “no” personally. 
• roasting our own names and why “be nice” matters 
• noticing how big brands still feel like they are improvising 
• learning leaders’ communication preferences and tailoring your output 
• keeping an open mind and questioning your assumptions 
• separating process from outcomes when teams argue agile vs waterfall 
• embracing...


Surviving An Acquisition (or Merger)
#23
06/23/2026

We go from questionable health oversharing to a serious playbook for surviving mergers and acquisitions without getting blindsided. We break down why companies buy other companies, how that decision affects your job, and what we’d do right away to protect our careers. 
• colon cancer screening and why health stigma keeps people from getting checked 
• why M&A creates fear through uncertainty and loss of control 
• the two big acquisition motives: technology or customers and how that changes outcomes 
• red flags for hostile acquisitions and why updating your resume can’t wait 
• who tends to be safest after...


Process That People Actually Use
#22
06/15/2026

We go from horror side quests and Big Corp nostalgia to a practical breakdown of how to build team processes people will actually follow. We share how to map workflows, get buy-in, use tools like Jira for accountability, and turn bottlenecks into data you can use to improve the team.
• canceling vacation to avoid getting sick and the reality of being immunocompromised
• why horror comedy is hard to nail and why Widows Bay works
• the gut-punch of watching an old company get acquired and its sign come down
• time off as a tool for rest, focus, a...


The Onboarding Blueprint...McDonalds
#21
06/08/2026

We record from a McDonald’s and use the chaos to talk about a surprisingly serious problem: most companies still onboard people with vibes and tribal knowledge. We lay out what great onboarding looks like, how to survive when you get none, and why networking plus documentation can turn you into a rising star.
• Why onboarding sets culture and context fast
• The difference between being “thrown in” and being set up to win
• A five-day company onboarding model that levels everyone
• Teaching the “why, what, how” before role details
• Using a one-minute pitch test to drive real learni...


What If Being Yourself Is The Strategy
#20
06/02/2026

We get brutally honest about “executive presence” and why the best workplace presence usually comes from being more yourself, not less. Along the way we connect authenticity, personal brand, and culture fit to the everyday moments that shape trust, promotions, and how people feel when they work with you. 
• why executive presence is really a felt experience 
• authenticity as a career advantage people can sense 
• why fake it till you make it fails long term 
• finding the version of you that feels natural 
• culture fit and when a role demands seriousness 
• using your uniqueness to build tr...


Corporate Or Entrepreneur?
#19
05/26/2026

We bounce from spicy comedy to a real gut-check about dread, burnout, and why “stability” feels different than it used to. Then we get practical about corporate careers vs entrepreneurship, including benefits, credibility, risk tolerance, and how to prove a business idea is real without ruining your future.
• turning exhaustion, fear, and self-doubt into the “burnout recipe”
• why health insurance and retirement planning can outweigh startup hype
• the underrated perks of corporate life: mentorship, friendships, and closing the laptop
• how resume credibility and company logos still change your options
• why entrepreneurship is ownership plus responsibility, no...


Public Speaking That People Remember
#18
05/18/2026

We catch up on a chaotic launch week, a new company announcement, and the growing noise around AI and tech culture before switching gears into what actually makes a presentation land. We share the practical public speaking and presentation skills we use to keep audiences engaged, stay calm under pressure, and communicate with clarity without sounding rehearsed. 
• a fast check-in on work chaos, health, and getting back on the mic 
• Michael’s company launch and the promise of agentic AI for reclaiming time 
• Palantir’s manifesto and why AI fear-mongering is spreading 
• why knowing your audience and goa...


Your Job Can Change Overnight, So Build A Career That Can Move
#17
05/07/2026

We go from breath-holding chaos to a surprisingly practical conversation about layoffs, AI-driven job shifts, and why people are quitting even when they are not the ones getting cut. We share a simple resume test for AI filters, then get real about identity, fear, and how to stay ready without spiraling on LinkedIn. 
• Pasting your resume into Notepad to see what AI and ATS tools actually read 
• Why fancy formatting, images, and broken bullets can quietly tank applications 
• Using Markdown thinking to make your experience clearer and more machine-readable 
• Layoffs plus voluntary exits as a culture and...


AI: It's the thought that counts
#16
04/27/2026

We start with a chaotic live setup and a soda taste test, then tumble into a real health scare that turns into a blunt check on stress, hydration, and the urge to work through everything. From there, we zoom out to AI hype, betting culture, and how companies monetize attention while we argue about what we lose when we stop doing the thinking ourselves. 
• the behind-the-scenes reality of going live and messing it up 
• trying an Italian cola and why it tastes like older Coke 
• a sudden hospital visit for chest pain and what the tests revealed ...


Make your work goals a reality with this one simple trick
#15
04/20/2026

We trade two wild stories from the same week, then use them to get serious about where AI helps and where it absolutely falls apart. We end with a practical playbook for finding time to learn new tools at a nine-to-five and turning that learning into goals your manager will actually support.
• Ingrown toenail border removal and why the procedure should not hurt
• Discovering an extra nerve ending and why a better doctor changes everything
• Getting trapped in an AI phone agent loop while trying to book care
• Why broken automation creates real risk and lost tru...


PTO Coverage Playbook
#14
04/15/2026

We go from theme-park chaos to a practical talk on how teams handle time off when a key person disappears for two weeks. We share what employees can do to protect their work, and what managers can do to build redundancy without burning out the team.

• debating what happens when a critical specialist takes time off 
• giving enough notice and setting expectations before PTO 
• using signatures, statuses, calendars, and handoffs for clear communication 
• documenting workflows and access so coverage is possible 
• cross-training and runbooks as a path to promotability 
• manager options: step in, delegate as g...


Why Corporate Work Feels Slow
#13
04/07/2026

We start with a new “What Are You Drinking” segment and somehow end up at a real question: why corporate work can feel frantic while progress feels slow. We break down the structural reasons big companies move carefully, plus the people problems that turn simple work into endless reviews, then share tactics to get context and reclaim momentum.
• trying Manhattan Special espresso coffee soda and reacting to the sugar and caffeine
• hating ads again after watching cable and how it fries attention
• using whole home ad blocking with Pi-hole and AdGuard Home
• noticing ads creeping into AI tool...


206. Grievance Audit
#12
03/30/2026

We vent about the small annoyances that stack up fast, from calendar ghosting to homeowner chaos, then shift into why corporate rules sometimes make life easier. We also spiral into AI optimism versus AI doom, how to spot what’s real online, and the communication tactics that keep work from turning into a mess. 

• getting stood up for a scheduled meeting and why it feels worse than it should 
• solving the “mystery leak” problem and the homeowner anxiety tax 
• flipping the switch into presentation mode and why expertise changes everything 
• documentary picks that reframe the manosphere and...


205. What If We Managed Friendships Like Work
#11
03/23/2026

We get honest about why people ghost simple invites and why “silence” turns into unnecessary stress for everyone. We trade tactics from corporate life that make personal plans easier, clearer, and way less emotional. 
• office awkwardness and the break-room microwave problem 
• jumping to “solutioning” with an AI microwave idea 
• vibe checks plus a real cat-feeding behavior fix 
• why Americans avoid direct answers in texts 
• “a non-answer is an answer” and how it wastes time 
• using “no thank you” and “no is a sentence” 
• following up without feeling mean or needy 
• timeboxing plans to force a clear RSVP 
• separatin...


204. Real world reactions
#10
03/16/2026

We bounce from a surprisingly emotional Pokemon Pokopia obsession to the less cozy reality of corporate ambiguity, where you can work all day and still have no idea if you “won.” We react to common workplace lines that sound normal on paper but often signal understaffing, scope creep, and reorg trouble, then we share scripts for pushing back with data and trade-offs. 
• Pokemon Pokopia as a post-work reset and nostalgia trigger 
• why feedback loops feel different across roles like marketing and product 
• “fast-paced environment” as a signal of long hours and poor planning 
• “other duties as required” and how j...


203. Return of the CACC
#9
03/09/2026

We break down a simple, durable way to measure work happiness and use it to make smarter career moves. Culture, autonomy, and challenge drive satisfaction, and compensation bends the curve when life needs change.

• What culture feels like when it fits and when it drains 
• How autonomy ranges from steady structure to creative freedom 
• Why challenge should be satisfying strain, not daily dread 
• How compensation offsets gaps and includes benefits 
• Signs to switch teams, negotiate, or plan an exit 
• How to score your week and spot patterns 
• Real questions to ask in interviews to gau...


202. Good Books
#8
03/02/2026

We trade the live-show chaos for a clear reading list that actually changes how you work. Mindset, systems, agile reality, and the hard leap from doing the work to leading the people who do the work.

• Seven Habits as a compass for priorities and people
• Subtle Art for choosing problems worth caring about
• Getting Things Done to clear the head and trust a system
• Start With Why and Five Whys for sharp messaging and goals
• Lean Startup, MVPs, and when agile works or fails
• Hybrid delivery for legacy constraints and real risk
• Phoeni...


201. How to Documentation in 3 Easy Steps
#7
02/23/2026

We swap aliases for real names, thank new YouTube subscribers and Patreon supporters, and weigh Discord’s privacy risks before diving into a full blueprint for documentation that actually gets used. From biathlon analogies to AEO tactics, we map how to build living docs that reduce chaos and speed up onboarding.

• live show update and community shoutouts
• discord verification risks and alternatives
• vibe check and the chaos scale at work
• winter olympics biathlon and mountaineering analogies
• proactive vs just-in-time documentation
• video-first tutorials with searchable transcripts
• confluence labels, ownership, and review cadence
• reducing t...


200. Corporate Strategy Unmasked
#6
02/16/2026

The masks are off. After five years and 200 episodes, we share our real names, real faces, and the real playbooks behind our careers—what worked, what didn’t, and why we’re changing how this community grows.

We start with the origin story: two friends who turned lunch rants into a living archive of corporate survival. Anthony traces a winding path from QA to automation, into sales engineering and national architecture, before vaulting into marketing with a technical edge. Michael recounts a non-linear climb through Apple business sales and support into software engineering, then product management, where he lea...


199. White Collar v. Blue Collar
#5
02/14/2026

We turn a hungry cold-open into a sharp look at authenticity at work, comparing blue-collar bluntness with white-collar polish and the role trust plays in both. We share ways to build psychological safety on corporate teams, when to change teams, and why culture beats theater.

• ad slogans and a Handy Way Subway bit leading to a comfort-food debate
• Florida cold snap as a frame for pressure, resilience and team response
• Reddit claim that blue-collar is authentic and white-collar is performative
• trust curves in blue-collar vs white-collar and why filters differ
• cheerleader culture, Kool-Aid vibes and...


198. Questioning college and what comes next
#4
02/09/2026

We skip the intro and get real about college, internships, and how to build a career in a world where AI changed the entry ladder. We share honest regrets, better playbooks for freshers, and why managers should hire for outcomes over pedigree.

• how a recording glitch shifts the vibe and sparks a candid tone
• reflections on ignoring goals and the cost of busy seasons
• cold weather banter that turns into perspective on change
• megaquake anxiety as a metaphor for rapid shifts in work
• college regrets and the case for work first, education second
• why...


197. Do HR Managers work?
#3
02/02/2026

We compare hands-on craft with hands-on leadership and ask whether the best managers must be able to do the job. Stories of bad HR-only management, better coaching habits, and how trust plus context beat micromanagement every time.

• tradeoffs between art, craft, and making a living
• repair culture vs modern tech and subscriptions
• practitioner managers vs HR-only managers
• why context matters in software and product work
• how micromanagement kills learning and autonomy
• using a 30-60-90 reset when inheriting teams
• when HR models work in unions and first response
• sales as a domain that de...


196. Time
#2
01/26/2026

We go from laser-beam shenanigans and comic book hot takes to a practical, no-fluff playbook for managing time at work. A simple framework, clear constraints, and better negotiations turn chaos into momentum and make you look reliably in control.

• three-answer intake for new requests: yes now, yes later with a date, or no
• clarifying questions that set purpose, deadline, and success
• Parkinson’s Law and the cheap, good, fast trade-off
• stakeholder time negotiations and priority mediation
• manager alignment by sharing your active stack for reprioritization
• scope to time: match quality to constraints without guilt<...


195. New Year, new resolutions, new pod?
#1
01/19/2026

We reset after a rough start, rethink resolutions, and set practical systems for goals, energy, and community. Then we lay out how Corporate Strategy will evolve with better culture habits, smarter distribution, and listener‑driven formats.

• why most resolutions break and how to make them stick
• accountability groups, reward ladders, and deadlines
• daily walks and low‑intensity movement for clarity and health
• open office hours, lunches, and lean coffee to build culture
• reframing goals after setbacks and choosing to do less
• what “getting packaged out” means and why it can be rational
• growth plan fo...


194. It could be worse
#45
12/30/2025

We kick off with a playful threat to delete the archive and end up reaffirming why consistency, community, and humane work habits matter. Between holiday calendar chaos and culture clashes over PTO, we find wins in empowered teams, better tools, and a thriving Discord.

• joking about nuking the archive to highlight creative burnout
• whiplash from deletion talk to preserving episodes forever
• holiday downtime realities and quiet office tactics
• European PTO envy contrasted with U.S. grind culture
• frustration with last‑minute meeting cancellations
• calling out performative Slack activity around holidays
• team empowerment as t...


193. We could do better
#44
12/22/2025

We pull apart a messy year and name the misses with humor and honesty, from starving team culture to hoarding hard projects and losing the spark that comes from celebrating wins. A working model for change emerges: adjust CAC priorities, delegate with intent, and build rituals that make effort feel worth it.

• acknowledging culture debt after a year of nonstop delivery
• the costs of over-shielding teams and not delegating
• spotting hiring gaps when only the leader can do the work
• losing joy when challenge eclipses celebration
• using CAC to track shifting priorities and energy


192. Stupid interview questions
#43
12/15/2025

We roast filler TV, then discover that “stupid” interview questions can reveal real judgment, curiosity and systems thinking. Fast riffs, real signals, and a few traps worth dodging.

• filler vs substance across anime and long-running TV
• appliance question as a proxy for work style
• estimation puzzles as a reasoning display
• survival in a conference room as constraint testing
• animal challenge mapped to role traits and nuance
• encoding a phone number without digits as creative constraints
• alien-on-the-team as an AI trap question
• pancake stacks as risk and failure-mode thinking
• motivation beyond email and noise...