Day in the Life: Carrie Richardson

Leadership Springfield Executive Director Carrie Richardson oversees the nonprofit’s work developing and connecting leaders from a cubicle in Efactory space at Missouri State University’s Brick City 3.

Her desk is orderly, with a family photo of her husband, Ben, and sons Sam, Toby and Gabe, Leadership Springfield plaques and key program dates, a Springfield Business Journal Most Influential Women award, a Republic School District calendar and even her CliftonStrengths results.

But on this rainy mid-April morning, Richardson isn’t at that desk. She’s 4 miles south at Classic Rock Coffee wearing Adidas sneakers appropriate for the amount of walking she’ll do today. At 7 a.m., she’s an hour early for Rise with Rosie, a Leadership Springfield networking event for women that’s open to everyone, including “brosies.”

Before her team arrives, Richardson edits a newsletter and plans tasks for the coming week. Her laptop is covered in Leadership Springfield emblems and a “Be the Sunshine” sticker; her wrist bears a matching sunbeam tattoo.

When it’s time to start Rise with Rosie, she helps Cindy Mergen, director of core programs and engagement, set up signage. Mergen hands over bullet point notes; Richardson likes to rehearse, so the first time she delivers her talking points isn’t in front of 30 guests. A half dozen attendees arrive early, talking about what’s bringing them joy, not just business strategy.

“Today is all about connecting with each other,” Richardson tells attendees. “There’s no agenda or official program.” Soon after, she checks her smartwatch, slips out and heads through the rainy parking lot to her next stop.

Being early is a win, she likes to say, so she built in a 30-minute buffer to travel back to the Efactory. Once out of the car, she opens her sky-blue Guaranty Bank umbrella and makes tracks, her long strides using every inch of her 4’11” stature. In a first-floor conference room, she sets up her laptop to meet with her bosses.

Those bosses sit on the executive committee of the Leadership Springfield Board of Directors: Brad Coy, Diana Tyndall, Jana Greig and Gretchen Russell, who joins over Zoom. The committee typically gathers two weeks before the full board each month.

“There’s some nuanced conversations about how they can support what we share at the board level,” Richardson says. “This is one time a month that we can connect [to ask] how is the organization doing? How can we support you? And also, it is a one-on-one for me … how can they hold me accountable?”

In the meeting, her tone is confident as she dialogues with her bosses, listens and toggles between spreadsheets, Trello boards, OneDrive files and agenda documents. She often speaks quickly, especially when summarizing past events. She credits her Italian-American background for being a “hand talker” – her words. When the conversation turns to passionate topics or accountability, she closes her fingers into a point and taps her heart or the conference table for emphasis.

After the meeting wraps, Richardson walks down Phelps Street back to Brick City 3, messaging her team en route about their standing Friday-morning event-planning session. The June 6 One Big Class Reunion, combining graduation for the newest Signature Class with a celebration of Leadership Springfield’s 40th anniversary, is on the agenda.

In a conference room, she sits opposite Mergen, with communications director Hayley Cobb and intern Maggie Groenke nearby. Mergen pulls up an events timeline for the 2025-26 program year and a checklist for the Leadership Springfield Academy graduation on April 23. Tasks are color-coded: Richardson’s in sky blue. A key thread is how to keep preparations on track while Mergen is on vacation.

“I’m fine to take whatever needs to be done after that,” Richardson says.

With the spring event-planning meeting complete, Richardson heads to lunch at The Table with Greig, who is preparing to step into the board presidency. The core of their conversation is the relationship between the board and Richardson as executive director and building supportive communication.

“We want you in this role,” Greig tells her. “I don’t feel like I need your physical proximity, one hour a specific day every month to get a meeting as the defining value.”

Richardson takes notes on her tablet as they discuss meeting frequency and communication. “As long as you’re communicating,” she says. “Different board presidents have handled it different ways.” Greig, who cites mentorship from C.J. Davis, shares advice that a top executive should spend roughly 10 hours a week thinking about, meeting or talking with their board. They trade views on balancing governance with day-to-day operations. “Yes, it’s constantly nuanced,” Richardson says. “And to me, one of the most difficult parts.”

They briefly compare approaches to one-on-one meetings with direct reports; Richardson often opens by asking “what’s on your mind?” to spur more authentic conversations.

Later, she recounts a hiking trip with her sister to Sedona, Arizona, where they got tattoos: Richardson has one that looks like sunbeams, her sister has a moon tattoo.

“I’m the straight-laced, cool, follower, A-plus student type person, where she has always been a little more like the rebel,” Richardson says. She considers herself a practical realist and says the tattoo is a spiritual reminder that “there’s so many things more important than the stuff that drags me down.”

After lunch, Richardson meets fellow executive director Rachael Walsh of Better Block SGF at Kingdom Coffee. Walsh, named Better Block’s first executive director in March, leads a nonprofit formed during the COVID-19 pandemic to improve underused urban spaces.

Over coffee in a quiet corner, they focus on relationship-building, goal-setting and the nuts and bolts of operational onboarding: bank permissions, tax documents, contracts.

“The hardest thing for me at the beginning was trying to juggle all of the different pieces that had to be done and not enough time to do them,” Richardson says. “When there’s literally nothing, and you’re creating it all from scratch, there’s a whole level of work that’s like, oh, I’m just starting a company actually, even though the company has existed.”

They wrap a few minutes early, and Richardson returns to Brick City 3 to check in with staff and finish office work. She leaves at 5 p.m. for dinner at Greek Belly with her husband and their 14-year-old “foodie twins.”

Back home in Republic, she reads for about an hour, then the family makes an impromptu trip to Andy’s Frozen Custard to meet her 18-year-old son Sam and his girlfriend. Richardson orders a gooey butter cake concrete.

Later, she makes a weekend to-do list, including projects for Sam’s upcoming high school graduation party, sorts laundry, reads a bit more and, as she puts it, “crashed after a long week.”