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Chapter 2


Leona Watson
Cheeky Food Group
Offers fun cooking events for corporate team building
10 full-time employees, 20 rotating chefs, founded in 2001

Leona Watson’s first job was as an administrative assistant making $13,000 a year in a remote Queensland mining town. She’s a self-admittedly poor assistant who wasn’t that great at filing and typing. Rather than letting her job description define her duties rigidly, she took a “no boundaries” approach and was soon doing PR and interviews on behalf of the company. And she was only sixteen at the time.

About a dozen years later, Leona Watson landed a plum gig working at Microsoft in the UK, launching Windows NT. On a whim, she took a vacation working on the crew of a tall ship, and had the 4:00 pm to 8:00 pm and 4:00 am to 8:00 am watch. While surveying the scene for submarines and other boats in the tranquility of dawn at open sea, Leona had a moment of clarity. She realized that she was in the wrong job. Even though she had a fabulous role flying around the world and making good money in a great corporation, the big corporate thing was not her bag.

She promptly resigned her Microsoft position at age twenty-eight to move back to Australia. She’d fallen in love with a sailor on the tall ship and ended up working on a yacht with him—but earning only $1 an hour. Her friends and family were shocked at her decision to leave Microsoft, but she contended that if things didn’t work out, she could always go back. In addition, how could anyone argue with working on the water beneath a smiling sun in a bathing suit and sarong?

Leona’s responsibility on the boat was preparing meals. She loved the people interaction aspect. So, when she moved back to Sydney, she studied at Le Cordon Bleu to sharpen her culinary skills.

Around that time in 2001, Leona was approached by two other chefs to start a foodcompany with an innovative concept—team-building through cooking—and she took the plunge and started the Cheeky Food Group. Eventually, she bought out the other partners and has been the sole director for the last five years. Their vision was to take the joy, fun, laughter, and interaction of cooking and put it together with relationship-building at corporate events, cooking classes, and tours.

Cheeky doesn’t embrace the idea of classic teacher-student relationship. Instead, they want everyone to roll up their sleeves and jump in, all while savoring great wine and grooving to fun tunes. This way, a CEO can be working alongside an assistant, and office politics go out the window. And, after 50,000 happy participants, the tally has been:

  • Ambulances = 0
  • Stitches = 0
  • Bandages = a handful

Today, Cheeky Food Group employs ten full-time staff and maintains a bench of twenty part-time chefs. Leona Watson claims that the company’s main strategic assets are the brand, reputation, and people. She fervently believes that the brand has to be embodied by everyone, from the person answering the phone to the chefs. Even if a prospect doesn’t end up buying, they should have such a strong connection to the brand that they would recommend Cheeky anyway. Cheeky actually maintains a 100 percent track record of “Yes, I’d recommend you” from their clients, which feeds into their strong reputation.

The people who embody the brand and make the reputation start to build bonds with people in their very first conversation, so that by the time of the event, clients are hugging the Cheeky staff because they have already started a great relationship. Sixty to seventy percent of Cheeky’s business is repeat and referral events. So, as Leona states, “unless we really screw up, we can keep this up with no marketing.” Such a great repeat customer rate is definitely a huge asset.

After ten years, Leona Watson has seen her share of triumphs and learnings as she’s grown Cheeky Food Group. Leona reveals the following insights and lessons for other entrepreneurs.

Cook up a Catchy Name

Leona came up with about ten possible names for the company. She emailed those options to fifty people for feedback. Cheeky Food Group was the second most popular name, and it didn’t polarize anyone. The most popular choice was “Mad about Food”: most people loved it, but some did hate it. So, in the end, Leona decided on the second-most-popular name—one that didn’t rub anyone the wrong way.

Don’t Be Afraid to Jump

Leona Watson astonished friends by walking away from a golden role at Microsoft, yet she said that the decision was quite easy. Leona relates that some people operate from a position of fear, but she refuses to. She even notes that, if everything went downhill with Cheeky Food Group, she would still land on her feet—she could work at a coffee shop and be okay. Leona is someone I deem a “cat.” Regardless of how high the fall or how great the turbulence, she has enough skill and tenacity to land on her feet.

I grinned when Leona shared this anecdote with me over beers at the local taco shop where I interviewed her. It wasn’t the alcohol (or maybe it was a little bit) but the fact that it’s okay to jump! Along the same lines, I like to ask myself when confronted with a major decision, “what’s the worst thing that will happen?” If you’re like most people, you’ll find a way to land on your feet. Jump!

— David Niu

Find the Right Ingredient for your Culture

Leona Watson states that every time that she made a wrong hiring decision, it was because she misjudged the applicant’s people skills. She cautions fellow entrepreneurs to test for this, especially in a small-team environment. In addition, when pressed to choose between someone with a high culture fit but low skill level, and someone with a low culture fit but high skill level, she said that it depends on the role and how easily she can coach the weak areas. So there’s no one-size-fits-all answer to that question, but she suggests always thinking about a person’s own strengths and weakness, plus the company’s values, before putting someone into the mix.

Listen to Your Job Applicants—On Voicemail!

Cheeky desires outgoing, energetic personalities to come on board, so to screen for those, they ask job applicants to call a specific number—and never email a résumé. The voicemail asks for basic information, such as what role you’re applying for, why you would be good in that position, and what “Cheeky” X factor you would bring. Leona says that by hearing the candidate’s voice and energy (or lack thereof) in the voicemail, she saves a tremendous amount of time. She can ascertain if she wants to meet the applicant within thirty to sixty seconds of hearing the voicemail.

Stick With a Review Process That Works

Cheeky Food Group’s performance review contains fifteen to twenty questions and asks employees to rate themselves on a scale of 1 to 10. Some of these questions include:

  • How happy are you here?
  • How much do you fit into our “Own it, do it, smash it” culture?
  • How effectively are you working with other people?

Leona is also a big fan of Verne Harnish and his “start, stop, continue” templates. She likes to ask her staff to come up with three bullets in each category to share. This quickly bubbles up areas for improvement and problem spots. She even took her entire team to a Verne Harnish event.

Follow Through to Keep Momentum

After the company had gone to the Verne Harnish event, they were very gung-ho. They had collected a lot of great action items to work on. Unfortunately, after the event lit the fire, there wasn’t enough follow-through to maintain the momentum. So the ideas and goals died a slow death. Leona has vowed to improve this in the future, and to follow through on problem-solving after identifying the trouble areas. Leona now believes in achieving “less” but doing things well instead of setting Cheeky up to fail or get overextended with new ventures.

Performance-Based Compensation Compromise

Recently there was an employee who requested a raise, but Leona knew that the individual had areas that needed work. So they devised a three-month plan. If the individual improved in the four areas that they both agreed upon, then Leona would provide her a raise along with back pay from the prior three months.

Keep the Focus on Your People

For the past year or so, Leona admits that she’s taken her eye off of the people-management horizon. She was experiencing challenging personal and professional issues, and it culminated in losing six out of nine employees. She admits that it’s tough to lose so many employees in a short period of time, but it can also be a refreshing new start. In fact, in some instances a big “clean out” is the best way to go, because if people’s attitudes or performances can’t be turned around, it’s best to replace those folks with new team members.

Personality Tests for All

Everyone at Cheeky Food Group takes the DISC personality assessment. Leona knows that they have a lot of “type-A” personalities. Everyone is rather fiery, and that’s part of their culture. However, for two recent hires, she’s been looking for a better complement to herself and the team, with higher Influence and Compliance attributes. Leona is a big proponent of knowing her strengths and limitations as she hires the right team to surround her.

Candid Self-Evaluation

Leona just started working with PricewaterhouseCoopers. The consultants asked her what was holding the business back from growing. Leona said, “me.” It’s an amazingly self-aware answer, and Leona knows that she’s why the business is as successful as it is. But she’s also the reason why it hasn’t reached the next level yet. She wants to make sure that there’s another executive who can team up with her to take Cheeky Food Group to the next level.


At an early age, Leona Watson realized that work—and life, for that matter—didn’t require boundaries. She could take the initiative, follow her heart, and devote herself to something that she could be passionate about, from PR to marketing to sailing to cooking. She asks, “What’s the worst thing that could happen?” Even if that worst thing happens, she will always land on her feet, be able to get a job somewhere, and be OK.

This refreshing approach frees Leona, yet she’s also introspective enough to know her own strengths and weaknesses. By initiating strong people-management processes like personality tests and outside coaching for herself, Leona has realized that she’s part of Cheeky Food Group’s limitations. Now it’s up to her to help bring in the right people and get out of the way, so that they can smash the boundaries to success. Hopefully they’ll quickly add to the 50,000 happy participants while maintaining the company’s perfect zero-ambulances and zero-stitches track record.