In this episode, host Jacob sits down with Casey Lucas Szumigala, founder and owner of Click Pragmatics, to dive into the messy, emotional, and absolutely necessary communication that keeps family businesses alive. Casey unpacks how families can talk about the hardest topics: death, money, responsibilities, succession, and transitions.
Drawing on real scenarios, Jacob and Casey explore what happens when a family member dies and someone outside the business is suddenly asked to “come run it,” how to plan for succession before a crisis, and how to navigate grief while still keeping the business afloat. They also dig into money conversations (who gets paid what and why), how to address feeling undervalued in a family role, and why clarity around pay structure matters so much in a family context.
The conversation then shifts to communication styles and generations how to speak to different personalities (direct, diplomatic, deliberate, dynamic), why knowing your audience matters, and how to approach pay and responsibility conversations depending on who you’re talking to. How emotional and social intelligence can help keep relationships healthy on and off the clock.
Finally, Jacob and Casey look at multi‑generational family businesses: older and younger family members working side by side, the temptation to stereotype generations, and how to replace “you don’t get it” with curiosity, respect, and shared values. Casey argues that every generation has faced its own hard things—and that leveraging each group’s strengths can create something no single generation could build alone.
About the Guest – Casey Lucas Szumigala
Casey Lucas Szumigala is the founder and owner of Click Pragmatics, a communication consulting practice focused on helping people communicate more clearly, compassionately, and effectively at work and in life. She specializes in social‑emotional intelligence, communication styles, and practical tools for navigating difficult conversations—especially in complex environments like family businesses.
In her work, Casey helps individuals and teams understand their own communication style, recognize others’ styles, and build strategies to better connect across differences in personality, generation, and role.
Her approach is grounded, pragmatic, and deeply human, with a focus on getting through the “ick” of hard conversations so people can move forward together.
Connect with Casey
- Website: https://www.clickpragmatics.com
- Email: casey@clickpragmatics.com
- Linkedin: https://www.linkedin.com/in/casie-lucas-szumigala-75a98795/
This podcast is sponsored by Zac Wild CFP, CEPA financial advisor with Edward Jones. Zac works for business owners who are interested in maximizing their investments in tandem with efficient tax strategies. this includes fully leveraging the benefits of 401k's, SIMPLE IRA, and other more unique tax advantaged accounts.