25 Leadership Lessons From Our Herculean Festival Mountain View Art & Wine Festival

Each year, the weekend after Labor Day, the Mountain View Chamber of Commerce organizes the Mountain View Art & Wine Festival. This year we celebrated our 43rd annual art & wine festival, and it truly was “A Festival Like No Other”. The festival’s roots started with humble aspirations – a fundraiser for the Chamber and a fun community event. Three blocks of downtown Mountain View were closed for the first festival. It was marginally successful. The Chamber’s Board of Directors had to purchase the unsold cases of wine glasses so that the Chamber wouldn’t lose money. Today, the festival draws over 150,000 attendees from throughout the Bay Area. Nearly 600 craft artists participate. The appetizing smell of over 25 food vendors lingers throughout the eight blocks of downtown Mountain View. Metro readers have voted the festival several times the “Best Festival in the South Bay”. Organizing a festival of this magnitude requires a herculean effort. In the six years, as the Chamber President & CEO, I’ve experienced the following leadership lessons from our festival.

  1. Know What Business You’re In. We are in the outdoor entertainment business. Our festival attracts people from all ages, ethnicities, socioeconomic levels, singles, couples, families, locals and people from the greater Bay Area. It is important that our eclectic selection of music, artists, food, exhibitors and sponsors fuse together to provide festival attendees a memorable experience, year after year.
  2. What’s the Purpose for Your Event? Identify your “Why”. Are you looking to fundraise? Promote a cause? Our festival is a fundraiser for our Chamber. Proceeds are used to run programs that help strengthen the vibrancy of our community through programs like Save Local Now, Leadership Mountain View and SOAR Scholarships.
  3. If You Can’t Beat Them, Join Them. Each year our festival competes with the start of the NFL season. On Sundays we experience a dip in attendance. Five years ago, we decided to add a 9’ by 12’ giant TV screen to show college football, MLB and NFL games. We setup chairs, added beer and food booths and named our new attraction the Pigskin Party Lounge. Each year attendance has increased and today sports fans look forward to cheering their favorite team with family and friends, while enjoying the festivities.
  4. Leading Volunteers is True Leadership. Getting your employees to do something because you’re their boss is positional leadership. Getting volunteers to do what you ask is influential leadership. Influential leadership requires earning the volunteer’s trust, respect and getting them to buy-in to your purpose. Volunteers give of their time freely and there is nothing holding them back from not helping.
  5. Plan, Plan & Never Stop Planning. We start planning for the festival nine months prior. We have a dedicated committee of key people that meet monthly. We also have a detail task list that is divided by month and lists action items by who, what and when.
  6. Have a Plan B. Even the past plans don’t materialize. This year an entire afternoon shift of volunteers didn’t show up for their shift. This caused a tremendous amount of strain on the morning volunteer shift. We decided to use Area Captains and move volunteers from other booths to relieve the morning shift.
  7. Hire for Attitude. Chambers of Commerce operate with a small staff. We have less than eight employees. Each of us takes on multiple responsibilities and does whatever it takes to get the job done. Dedication, commitment, team player and having fun are important personality traits. Emotional intelligence, the ability to manage your emotions, function under pressure and meet deadlines despite crap hitting the fan, is an important skill that I look for in a candidate. I don’t find value in hiring educated derelicts.
  8. Delegate. You can’t do it all yourself. I remember my first Art & Wine Festival. It was 10 AM on Saturday and I heard on the walkie-talkie that the festival had started. At that moment, I realized that the festival was in the hands of our nearly 500 volunteers. There was no way that I or my staff could possibly manage the festival on our own.
  9. Recruit & Train Leaders. If you want to add to your efforts, find and train people like yourself. If you want to multiply your efforts, find and train people that are better than you.
  10. Failure Isn’t Failure. Three years ago we partnered with a local mobile payment startup to allow festival attendees to purchase a festival glass and drink tickets. Even though we had hiccups with the new payment system, and the following year the startup decided not to continue the partnership, we learned that festival attendees were willing to embrace alternative payment methods besides only cash. Today we’ve expanded credit card payment virtually throughout the festival.
  11. Play to Your Strengths. I enjoy uplifting people. I make it a point to visit every booth and thank and compliment our volunteers. I also speak with artists and exhibitors to inquire about their experience at the festival. Making people feel appreciated is very important.
  12. Relationship First, Business Second. Too often we focus on the financial results vs. first focusing on nurturing the relationship. Over the years we have spent time developing relationships with our City, Miramar Events and California Artists. Each partner contributes to the successful running of the festival.
  13. Community Celebration. Our festival truly is a community celebration. Many local businesses, performers, nonprofits and schools participate in our festival and showcase the best they have to offer.
  14. Attitude of Gratitude. Never take people for granted. Each year we thank our sponsors and donors by listing them in the local newspaper. Our Volunteer Appreciation Party is how we thank our volunteers.
  15. Focus on Details, but Don’t Sweat the Details. We have multi-page spreadsheet that covers many details about the festival. It is important to track progress so tasks get done. Things will go wrong, but 90% of the time when something does go wrong, it gets resolved.
  16. What’s in it for Others? Focus on helping others achieve what they want and you will achieve your goals too. Too many times we focus on our needs first. People don’t care what you say. They care how you make them feel.
  17. Honor the Past, Embrace the Future. While other festivals allow resellers, we have maintained the authenticity of the festival and only allow artists to sell crafts they make. At the same time we embrace new technology. For example this year we partnered with a local startup, GLIFF, that allowed festival attendees to scan an image and access information about the artist on their smartphone. This gave artists more exposure.
  18. Start Small. This year we added a premium wine tent. We partnered with the Santa Cruz Mountains Winegrowers Association, five wineries and a Chamber member. By starting with a pilot program, we can test new offerings, solicit feedback, control exposure and make adjustments quickly.
  19. Be Willing to Rollup Your Sleeves. Titles don’t matter. Everyone is expected to help wherever help is needed.
  20. Praise Others. Compliment and recognize others.
  21. Complacency is Death. So you had a great festival. Never rest on your success. Each year we have added a new attraction to the festival. For example, we’ve added the Pigskin Party Lounge, mobile payments, accepting credit cards, Latin rock music, salsa music and the premium wine tent. This draws more attendees and helps us create a new buzz each year.
  22. Listen, Review & Repeat. Always be open to feedback. Review what worked and didn’t work. Repeat what worked and stop doing what didn’t’ work.
  23. Give to Grow. Local nonprofits have the opportunity to generate thousands of dollars in revenue or gain exposure at the festival. We allow them to manage the parking lots, sell food, have a booth space and perform at the festival. In return, they attract their supporters, which leads to more festival attendees.
  24. Use High-Tech & High-Touch. Use technology to promote and engage with attendees, as well as to track results. We use social media to share information about our festival. Remember that behind every post, there is a person. There may be times when you will need to call or meet with someone face-to-face, especially if the person has a concern.
  25. Have Fun. It’s important that everyone has fun before, during and after the festival. My staff works long hours, especially the weekend of the festival. Each year I treat them to a fun outing. We’ve gone to the Giants’ and Sharks’ games, sightseeing to Alcatraz and other fun outings.

The Mountain View Art & Wine Festival is a festival unlike any other, in a city unlike any other, managed by staff and volunteers unlike any others. #2030NOW

Oscar is Founder & Chief Empowerment Officer of Aspira, a community relations, economic development, and training firm that empowers, engages and educates clients.
Created By
Oscar Garcia

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