In a recent episode of #PastthePitchPodcast, I had the pleasure of sitting down with Christine Sandman Stone , an award-winning author, advisor, tech transformation leader, and perhaps my favorite detail, a self-proclaimed pragmatist. Our conversation was equal parts insightful and refreshingly human.
Here’s a look at some of the most powerful takeaways from our chat (and trust me, there were many).
1. The Unexpected Cost of Leadership: Freedom
Christine dropped a truth bomb early in our conversation that stuck with me: the higher you go in leadership, the more freedom you lose. That might seem counterintuitive, but she broke it down in a way that made it feel obvious.
- Loss of calendar freedom: Leaders don’t have the luxury of flexibility. Calendars fill up fast with board meetings, town halls, and crisis responses. If anything, the time becomes more structured, not less.
- Loss of expressive freedom: When you’re in a leadership role, your words carry serious weight. Christine emphasized how even a casual comment can ripple across an organization. Leaders often know things they can’t say, and finding ways to communicate clearly without triggering concern or confusion becomes an art.
Her reflections reframed what leadership really looks like, not just the influence or decision-making, but the weight of stewardship.
2. Thriving in Chaos: The Power of Patterns
When we moved to the topic of adaptability, Christine lit up. It turns out, she thrives in moments of change. One example? She joined Groupon two weeks before the pandemic.
Talk about trial by fire.
Christine shared how her team pivoted from promoting in-person experiences to enabling merchants to sell tangible products. She also led the implementation of Objectives and Key Results (OKRs) to realign tech efforts with measurable business outcomes. The result? During a wildly uncertain time, Groupon hit six consecutive quarters in the black.
Her core message here was simple but powerful: patterns create stability. Quarterly goals, consistent measurement, and regular all-hands meetings helped bring structure to the chaos. It’s a concept that applies well beyond the world of engineering or product. Sales leaders, take note.
3. The Branding Balancing Act: Authenticity Without Oversharing
You’ve probably heard the phrase “bring your whole self to work.” Christine isn’t buying it.
In her view, there’s a difference between being authentic and being unfiltered. While personal values and character traits should be consistent, not everything belongs in the workplace.
One of my favorite parts of this discussion was her exercise on selecting three words that describe you professionally and then asking, “Would these words help you get promoted?” It’s a clever gut check that prompts a more intentional personal brand.
And as we both agreed, vulnerability has its place. Owning a mistake and modeling how you’re addressing it? That’s powerful. Sharing every emotion in real time? Maybe not so much.
4. Measuring the Moment: Creating Standout Customer Experiences
Christine believes in outcomes over optics. Her secret to unforgettable customer experiences? Measurement and personalization.
She shared a story about helping an EVP prepare for a high-stakes presentation during a corporate restructuring. Christine not only reviewed the document but transformed its first page into a visual summary that ended up being showcased by leadership as a gold standard.
It was a great reminder that often, the most impactful work happens quietly—in the margins, over a weekend, behind the scenes. But when you understand your audience and you elevate their message, the results can echo far beyond the moment.
5. A Book Born from the Real World
We wrapped up the main conversation by talking about Christine’s book, The Modern Management Mentor. What started as a series of practical notes to help a young manager (who turned out to be her daughter!) evolved into a comprehensive guide packed with 50 tools for leading with clarity and confidence.
What makes the book so effective is its practicality. It’s not fluff. It’s not theory. It’s the kind of advice that helps a first-time manager know how to navigate a holiday party with grace and confidence, or how to structure their first one-on-ones. And based on its growing popularity among seasoned managers, it’s proving useful well beyond the entry-level crowd.
There’s more, of course, including our lighthearted rapid-fire round, but I’ll leave that as your reason to go listen to the episode.
Big thanks again to Christine for bringing her insights, her honesty, and a bit of humor to the conversation. If you’re navigating leadership in any form, you’ll find something relatable and valuable in this episode.
🎧 Listen to the full conversation on Past the Pitch here.
