Who's the Boss? The Next Generation: Derek and Holly Zschokke from Glassing Florist
The "Who's the Boss?" summer series continues with a mother and son navigating one of the hardest transitions in retail floristry: passing the family shop to the next generation. Holly Zschokke is the second-generation owner of Glassing Florist in Minnesota, and her son Derek — who Vonda and Lori have known for over a decade — is stepping in as the third. Their conversation is a candid look at how a succession actually works when it's going well.
82 years and three generations
The retail business officially dates to 1940, when Holly's parents married — her grandfather grew flowers and sold them to retailers even before that. Holly grew up in the shop, and she and her husband Bruce bought it from her parents in 1990. Interestingly, each generation flipped roles: Holly's dad was the creative who did the purchasing while her mom handled the books; Holly and Bruce are the exact opposite. Now, with retirement on the horizon — and, as Holly says, after 2020 made everyone ready for a change — the shop is heading to Derek and his wife Liz. Of her four kids, Derek was simply the one with the interest, so there's been no family struggle over it.
The boss who can't design (and doesn't need to)
Derek grew up washing buckets with bleach and riding to work with his dad, but he's quick to say he's no designer — he can "whip out a mean dozen roses" (he's won bets on it) and that's about it. His passion is the business side: crunching numbers, marketing, purchasing, and growing the shop. After a business administration degree, he spent ten years away — five consulting for a couple hundred flower shops around the country and five in a corporate role. Both, he says, made him a better future owner: consulting taught him what works and what doesn't across shops big and small, and corporate life taught him how corporate customers actually buy — purchasing cards, expense reports, all of it — which he can now use to win corporate business.
Sharing the boss hat during the transition
So who's the boss right now? They're sharing it. Holly has happily handed flower ordering back to Derek and is ready to pass off hiring; Bruce still runs the books, which suits Derek fine since bookwork is his least favorite part of the job — though he admits he needs to learn "how that particular sausage is made." His parents have given him latitude to change anything he thinks matters, but his first months back have been deliberately observational: watch, ask why things work the way they do, and resist changing processes that aren't perfect but get the job done.
With staff, Derek has been careful. No barking orders after seven months back — he critiques in private, praises in public, and is especially thoughtful about giving creative feedback to designers, knowing what it means for a non-creative to critique someone's art. A telling detail: newer hires bring problems to Derek, while longtime employees still go to mom and dad — and that balance is shifting naturally, without forcing anyone out of a good team.
"Because we've always done it that way" — and other fuses to light
Holly's advice to owners handing off a business: expect changes, because there need to be changes — the industry demands it (though she holds the line on one thing: if you're going to cut a rose, you need a knife). Derek's version is spicier: when the answer to "why do we do it this way?" is "because we've always done it that way," he wants to light a fuse under it. Often the old way is the best way — but then you should be able to say why.
His biggest advice for any next-generation successor: get out of the shop and work for somebody else first. Working for people who weren't his parents taught him what leaders are expected to be — and let him mash together his parents' example, corporate lessons, and his own style. He doesn't want to be the boss with a capital B; he wants people who want to follow, who understand that keeping costs in line and growing sales isn't greed — it's how everybody gets to stay.
Family, all the way down
The part Derek is proudest of: making the shop a family affair on purpose. Liz joined the team before he did, and now she's finding her lane in display and merchandising — dog-earing catalog pages the utility-container buyer would never touch. The kids ran a lemonade stand at the shop (they still owe the bank, and yes, there's interest). As Holly says, having customers tell her "your mom did my parents' wedding, you did mine, now you have to do my daughter's" — and knowing a third generation wants to carry that on — is the proudest moment of all.
Key takeaways
- Succession works best as a gradual handoff — share the boss hat and transfer duties one at a time.
- Next-generation owners: go work somewhere else first; outside experience is the best leadership training.
- Observe before you overhaul — understand why processes exist before changing them.
- Critique in private, praise in public, and handle creative feedback with extra care.
- Interrogate "we've always done it that way" — keep it if you can say why, change it if you can't.