It started with cupcakes. As a teacher at Oak Park Elementary, Caroline would often make cupcakes for the school’s teachers and staff. Everyone raved about her baking expertise, and a colleague asked Caroline to make cupcakes for her son’s birthday party. The treats were such a hit that many of the parents at the party asked Caroline for her phone number, and she quickly found herself baking for multiple parties a week.

After a year of baking for private parties, an opportunity arose for Caroline to take her business to the next level. After a local coffee shop went out of business, Caroline signed a contract for its space and opened Sweet Caroline’s, a bakery featuring her cupcakes, muffins, Danish, and other baked goods.

Starting small with birthday parties and graduations and growing to wedding receptions and banquets, Sweet Caroline’s quickly became the most sought-after caterer in the city. As the demand for catering cupcakes and cakes outside of regular business hours grew, Caroline expanded her staff and the services they offered. In just five years, Sweet Caroline’s morphed from a small bakery into a full-service restaurant and catering company.

Although Caroline had no plans of ever going into business, Sweet Caroline’s has been very successful.

Caroline is very personable and genuine, which has been instrumental in creating a large and loyal customer base. Furthermore, Caroline’s intuitive sense for how to tailor her services to fit the needs of the community has fueled the company’s growth. Despite her success, however, Caroline has struggled with certain aspects of running Sweet Caroline’s.

Now five years after Sweet Caroline’s opened, it has become a highly complex operation to keep organized.

Caroline’s staff has grown to 40 employees, some who work in the bakery, some in the restaurant, and some in both places. There are five drivers who deliver cupcakes, cakes, and other catered goods to private parties and businesses six days a week. In addition, Caroline runs weekly ads in the local media, on the radio, and on the Web. Her 22-year-old daughter manages the company’s Facebook page and Twitter account, which boasts more than 3,000 followers.

Caroline is a skilled baker, but she is finding that the demands of her growing business and client base are creating challenges that are out of her area of expertise. Many of these fall into the administrative area where she hasn’t the patience or knowledge to deal with detail-oriented aspects of managing her business.

For example, Dale, Sweet Caroline’s delivery driver, is often frustrated because the company does not have a system for how orders are to be delivered throughout the city. Dale worked for another company that had a “zone system” so that each driver delivered all orders in one specific area on a given day. In addition, Caroline has opted not to use computers at her company, so all delivery orders are written by hand and then rewritten on clipboards for the drivers when the order is ready. There are often mistakes including duplicate deliveries or a delivery that gets missed completely.

Caroline also struggles with scheduling. Employees’ work schedules are developed the weekend before the start of a workweek so that employees often are unaware of their upcoming shifts. As a result, Sweet Caroline’s is constantly understaffed. The food and baked goods are so good that patrons rarely complain about the wait, but staff members get frustrated with the lack of notice regarding their schedules, the lack of staffing, and the stresses these issues cause.

When it comes to catering events, there is often chaos as Caroline chooses to work on food preparation, while leaving staff members, who are not trained to do so, to plan the events, manage client concerns and issues, and execute the event. While the quality of the food is consistently superb, clients are often surprised by the disorganized style of the catering staff. The staff feels it, too; many have commented that they feel like they are “running blind” when it comes to the events because Caroline gives very little direction and is often not around to help when issues arise. Caroline, however, has a good working rapport with her staff, and they acknowledge that Sweet Caroline’s can be a fun place to work. For her part, Caroline knows that working in a bakery can be difficult and demanding, and she consistently praises the efforts and dedication of her staff members. Caroline is also very good about pitching in and working with staff on the production of cupcakes, cakes, and food items, working side-by-side with them on big orders, while providing them with positive encouragement.

Caroline truly enjoys the novelty of being a business owner and handles all the accounting and payroll duties for the company. Unfortunately, this aspect of the job is becoming more demanding, and Caroline spends an increasing amount of time on these duties, leaving more and more of the day-to-day operations and catering to her staff.

Caroline has been approached about opening a second Sweet Caroline’s in a neighboring town, and while she would like to build on her success, she already feels overwhelmed at times by her current operation and is not sure she can take on more. But she also knows the opportunity to expand won’t last forever.

Questions

1. Based on the Model of Primary Leadership Skills, how would you describe Caroline’s skills? In what skills is she strongest, and in what skills is she weakest?

2. Sweet Caroline’s bakery and restaurant seemed to emerge out of nowhere. What role did Caroline play in this? Do you think Caroline could improve her business with more strategic planning?

3. Have you ever worked at a place that was very successful but felt quite chaotic and disorganized?

How did you handle it?

4. If you were a consultant to Caroline, would you recommend she open a second location? If so, what three specific skills would you have Caroline develop in order to help manage her business better?