Brent Kenneway: Meaningful Work

Episode Overview

In this episode of Gratitude Through Hard Times, Chris Schembra sits down with Brent Kenneway, National Group VP of Sales at UKG, for a conversation about the kind of relationships that aren’t transactional, the kind that actually nourish the soul. 

Brent opens with the gratitude question and doesn’t hesitate: he gives credit to his wife, Jenny, the person he says made his life and career possible by “holding down the fort” while he built his leadership path. From there, the conversation expands into parenting, identity, and leadership, especially Brent’s lived experience of managing “multiple personalities” at home with four kids and at work with diverse teams. The thread that ties it together is intentionality: Brent wants to be more present when he comes home, more human at work, and more consistent about building culture one interaction at a time.

Chris and Brent then go deep on a core leadership shift: moving from blame to radical accountability, and from problem-obsession to solution-finding. They talk about debriefing as a life skill (“What went well? What could have gone better? What will we do differently next time?”), and they challenge the cultural reflex to fix what’s wrong without first helping what’s already right go more right. Brent adds a key leadership balance: culture without systems breaks, and systems without culture underperform, you need both.

Finally, they tackle the future: AI, change, and uncertainty. Brent argues for People-First AI—AI as augmentation, not replacement, using the story of the handheld calculator as a reminder that tools can free humans to do more meaningful work. The takeaway is clear: the companies (and families) that win won’t be the ones that move fastest alone; they’ll be the ones who pair speed with depth—building trust, presence, and gratitude at scale.

10 key takeaways

1. Gratitude isn’t a “soft” thing—it’s a performance tool for leadership, retention, and resilience in hard moments.
    
2. Give credit to the people behind your success—Brent names Jenny as the foundation of his career and family stability.
    
3. Parenting and leadership are the same craft: multiple personalities, different motivations, one mission—learn what makes each person tick.
    
4. Presence is a transition skill: coming home from “business mode” requires intentional switching into family mode.
    
5. Radical accountability beats blame: the real shift isn’t “what did I do wrong?” but “how can I be better next time?”
    
6. Debriefs create growth without shame: “What went well / better / differently” builds learning loops that scale.
    
7. Culture + systems = results: positivity without structure fails; structure without humanity underperforms.
    
8. Leaders don’t hand answers—they develop thinkers: Brent mentors by asking, “What do you think we should do?”
    
9. Standardize first, operationalize second: clarity reduces confusion; consistent process multiplies performance.
    
10. People-First AI is the way forward: AI should remove the mundane and return time to relationships, creativity, and real human connection.

10 Quotes

1. “We’re here to talk about relationships and gratitude—but not the transactional type. The soul needs nourished.”
    
2. “I’m not at the position I am in my life without [Jenny’s] backing, her support, her guidance.”
    
3. “All four kids—completely different personalities. That’s the joy of parenting… and leadership.”
    
4. “If you’re present and recognizing the situation, it’s a lot easier to have that inward focus.”
    
5. “People are distracted… and that makes it harder to stay solution-oriented.”
    
6. “Culture without systems breaks—and systems without culture underperform.”
    
7. “I never give the answers. I ask: ‘What do you think you should do?’”
    
8. “We’re spending more time at work than we are with our families—so you might as well make it fun and human.”
    
9. “People-first AI… it’s augmentation. It speeds up the mundane so you can spend more time with people.”
    
10. “You can never connect the dots forward—only backwards.”