Letting Go: The Myth of Workplace Retention

Most organizations treat retention as the ultimate metric of success. But what if the obsession with keeping employees is costing you more than turnover itself?

In this keynote, Jack flips the script: retention isn’t about holding on, it’s about developing talent so fully that people thrive — whether they stay or eventually move on. With humor, stories, and actionable strategies, Jack shows why so-called retention perks like free soda on Fridays and foosball tables don’t work, and what employees really want: managers who care, listen, and invest in their growth.

And here’s the dirty little corporate secret: the cost of disengaged employees is much higher than the cost of bringing on new ones. When you invest in growth — even if people eventually leave — you create stronger teams, a healthier culture, and a pipeline of talent that never runs dry.

Learning Objectives

• Break the “just enough” cycle. Go beyond surface-level perks by training managers to care in practical ways: regular check-ins, active listening, and personalized development planning that make employees feel supported.

• Reframe turnover as a growth strategy. Implement “stay conversations” (career-focused check-ins before someone is ready to leave) and career pathing sessions that show employees their growth matters — even if it eventually takes them elsewhere.

• Rethink retention metrics. Move past turnover numbers by using tools like pulse surveys—short, regular mood checks—along with skip-level meetings where employees spend time with their boss’s boss, and project rotation programs that let employees try new assignments. These practices uncover stagnation early and re-energize your workforce.

Your audience will leave entertained, inspired, and equipped with a fresh framework for leadership that prioritizes growth over grip — and produces stronger, more engaged teams as a result.

The Intangible It

Jack’s longest standing keynote, The Intangible It, examines the “it” quality movie stars possess that you can’t quite put your finger on… or can you? By sharing humorous tales of his Tinseltown adventures, Jack breaks down the “it” factor that makes certain actors’ superstars and how to use those lessons to become a star in your profession.

You’ll learn about The Gift and how to channel your inner-Clooney to make everyone you encounter feel important. We’ll examine The Shift by exploring the secret that has given Tom Hanks such career longevity. And with The Connect we will dive into ways you can be more memorable to anyone you meet – and it might be as simple as wearing a Dolly Parton tee shirt. Really.

This presentation is the spoonful of sugar with the medicine because it delivers the fun and humor you want with the takeaways that you just might need.  

The Upside

The post-covidian era has created unique problems like staffing shortages, burnout and the increasing creep of a workplace staple: Negativity. Inspired by a certification from Yale on The Psychology of Well-Being, this is the newest of Jack’s presentations, so it still has that fresh keynote smell. In a nutshell, this program is about how to navigate negativity in the workplace and Jack examines how challenging times can bring big things to anyone, if you look in the right place. But as the GI Joe Fallacy (yes, that GI Joe) demonstrates, simply seeing the silver lining is not enough. It’s the doers who find the upside. Because in a world with so much downside, you can always find a way to… up yours.

Vantage Point

Roles can change in an instant. One moment we’re working a ho-hum 9-5er and the next there’s a health crisis and an economic shift and we suddenly have a new role at work or even in the household. For those of us in new positions the road ahead may look daunting. But if you’re in the right role and you’re able to surround yourself with the right team, it just might be the adventure of a lifetime. This presentation creatively weaves in life lessons, challenging your team to think outside of themselves, and see the world through the eyes of others. By taking that perspective shift, attendees will gain a new appreciation for decision making at any level within an organization. And what’s more, this is the rare presentation that applies to employees and managers alike, due to its creative concept. This keynote also has an accompanying book, Days of Our Work Lives.

Don’t Flinch: The Half Day

Even though Jack’s wife and kids would say an hour with him is plenty, some organizations opt for a longer and more intensive half-day session. In this two-and-a-half-hour program, Jack steps your team through a series of exercises that are equal parts fun and insightful. And because Jack takes elements from his keynotes and packs them into the half day, your team receives a greatest hits album of sorts, with the fun and humor of a keynote but also the impact of a workshop. See Jack for more details on how he can customize the program for your group.

Jack is also available as an emcee

Jack Stahlmann has kept audiences on their toes for years with his unique emcee stylings. His philosophy is that every event is different and because of that, he prepares uniquely for each group. He gets to know about your team, theme and goals to create an experience that works best for your specific event. When working with Jack you get more than a host who simply reads a script, you get a creative partner. He can help you craft the content – you simply provide the schedule, sponsors, and any other must-have information – and he can shape the rest. His quick wit will keep your event humming along and because he’s also a keynote speaker, you can package that together for an all-in-one solution for your event.

Available for corporate meetings, association gatherings and 1-year-old birthday parties if the price is right (and you throw in cake), he is a great fit for almost any event!