Windsor Mayor Drew Dilkens Leads The Way

Take The Lead – Windsor Mayor Drew Dilkens Leads The Way Through Tornados, Floods and A Pandemic

They always say you judge a person by how they perform through adversity, not success. Well, this means I now have an even greater respect for City of Windsor Mayor Drew Dilkens (elected October 27, 2014).

Windsor has always been known for its resilience and since “leadership starts at the top” Dilken’s path into politics prepared him to be tenacious in his quest for office and for the difficult challenges he would face in this leadership role.

His uncle, Marty Goldberg, was an Alderman who inspired the “political bug” early on in Dilkens who began to seek out leadership positions as a teenager through Student Council and getting involved in the community.

After a few failed attempts for the Windsor Utilities Commission and the public school board, he took what he learned from the experience and maintained his passion to serve.

He set his sights on City Council and knocked on almost every door in the largest riding (55,000) and was successful in 2006 and served two terms.

Dilkens credits his tenacity to keep pursuing his passion for politics as a decision to put things in perspective.

“A lot of great people run for office and not everyone can win,” he says. “I didn’t want to be one of the defeated candidates that you never heard from again.”

His family was just about to move to Belgium for a year on an adventure, when he received a call from Joyce Zuk stating she was not going to run in the next election for City Council and he was advised to step up.

“I have to credit my wife with encouraging me to not have any regrets and go for it, even though she realized just how much time and family life is sacrificed for political service,” he expresses.

Dilkens is grateful to his parents for raising him to give back, his uncle for being a political role model and his grandfather, who was involved in community service with the Masonic Temple and The Shriners. Another one of Dilken’s inspirations was his first grade teacher who impacted him so much that he has maintained contact with her.

A passion of our Mayor is travelling with his family, giving them an opportunity to experience different cultures and increase their global perspective.

He feels this exposure and perspective is one of the things that makes a good leader, along with getting a great education and becoming involved in the community.

Dilkens describes public office as an enormous responsibility: “You are part of a Board of Directors that is in charge of a budget of $850 million with a staff of over 2,500 people who are all making complex decisions that require understanding enormous amounts of material.”

He encourages everyone to get involved. “You don’t have to have a high-profile position to serve, you can be involved in grass roots initiatives and add your voice and time,” he suggests.

Mayor Dilkens admits it can be “lonely at the top” when you are making decisions for which you may have more information than other people, but he feels you must take risks. “You can’t be risk-free in this position or you won’t be able to grow and move your city forward,” he notes.

He believes that “you have to be able to take criticism and have a true passion to face the challenges, negativity and scrutiny.”

When he thinks of a leader that responded to a risk and endured tough times, he admires the strength of Brian Mulroney when dealing with the first North American Free Trade Agreement.

“Mulroney faced a lot of challenges and discourse and it was a hard sell with many implications, but it was the right move for our GDP for all three countries: Canada, United States and Mexico,” he comments.

Dilkens feels it takes tenacity to be a good leader: “It is important to bring others along when there is push back to new ideas; you need the confidence to stay on a path of improvement.”
He adds, “You need passion and the ability to engage ‘champions’ to help others understand why decisions are good and should be supported.”

One goal he has as a politician is to not worry about terms or making decisions to get re-elected, but to use sound judgement of what is best. “This is why I developed a 20 year plan, not a four year plan,” he explains. “In Korea they have a 35 year plan. It’s important to move to long term thinking and be prepared, through diversification of the economy, in case your largest employers are not around.”

His ultimate goal is to come together as a council and as a city in order to make Windsor better in every way possible.

Mayor Dilkens has faced tornados, floods and a pandemic, yet still maintains his positive “glass-half full” attitude.

“Our team and community have worked hard to diversify and improve infrastructure and quality of life and there are always new areas of focus that emerge,” he mentions. “We are working hard to revitalize our downtown and have made great progress, most recently with Double Tree and Quicken Loans and the WindsorEssex Economic Development Corporation relocating, the Paul Martin building bringing the library to the heart of the city, and St. Clair College moving into the Canderel building.”

He also stresses the importance of addressing our issues of homelessness, addiction and mental health support to keep our core vibrant and attractive to business, residents and tourism.
And what of the biggest challenge to date, the COVID-19 pandemic? The Mayor is proud of the actions of our citizens.

He feels it has brought out the best in our residents and he talks about examples where we come together to solve problems like the tough decision to temporarily cancel Transit Windsor service because of safety issues and lack of use. (90% stopped using public transportation during initial isolation).

Groups were immediately organized and 1,500 volunteers stepped up to transport food and medicine to seniors and our most vulnerable population and get them to their appointments through 211/311.

The City also supported the June 27th Miracle food drive by providing donation centres.

In addition Workforce WindsorEssex and the WindsorEssex Small Business Centre went online with their “#ShopYQG” campaign and the city is featuring and promoting small businesses and restaurants through “Take-out Tuesday” campaigns.

“The most positive effect this pandemic has had on everyone is an appreciation for family, friends and the need for human interaction and physical contact,” he says. “On a personal level I have been able to carve out more time for family dinners and activities and I think we are all re-focusing on what is important in life.”

Dilkens concludes with this message of hope . . . “Windsor is strong, caring and resilient, we will make it through this together and our community will come out on the other side of these challenging times an even stronger city!”

If you would like to interact with the Mayor go to facebook or view the latest city news on

Sherrilynn Colley-Vegh is an award winning leadership consultant and former Director of Leadership Windsor/Essex, Principal, Chief Communications Officer and business owner with over 30 years of experience in education, administration, mentoring, consulting and community leadership. If you know a leader in the community to profile here in this column email: [email protected]

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Sherrilynn Colley-Vegh is an award winning leadership consultant and former Director of Leadership Windsor/Essex, Principal, Chief Communications Officer and business owner with over 30 years of experience in education, administration, mentoring, consulting and community leadership. She is also the founder of Girls Rock Windsor, which supports camps across the world to develop leadership, social justice, community awareness, positive self-esteem and a sense of belonging, using music education and performance.