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7 Questions on Leadership with Robert Brill

Name: Robert Brill

Title: CEO

Organisation: Brill Media

Robert Brill is the CEO of Brill Media, a digital advertising agency for scalable business growth, and a 10-time honoree across the Inc. 5000 and Financial Times 500.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Robert's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Leading is exceptionally nuanced. It requires many different perspectives to make the right decisions at the right times. So, the challenge has been to recognize those challenges, followed closely by the ongoing pursuit of becoming a better leader.

2. How did you become a leader? Can you please briefly tell the story?

I spent 10 years in the advertising business when I started my advertising agency. My goal was to create freedom for myself, and our clients. I wanted to keep working in the advertising business, an industry I love, and to take on new and bigger challenges over time. The opportunity to help businesses achieve that freedom of time and money is important because I want others to have what I have.

3. How do you structure your work days from waking up to going to sleep?

I focus on doing the most important work in the morning, and the most rote or monotonous work at the end of the day. This way I can focus my most creative energy on the most important work. When I wake I'm checking X, crypto prices, emails, and Slack. Then I'll attend meetings, which are mostly sales and marketing calls. We'll interlude with any operational elements that might need my attention. Finally, throughout the day I'm working on PR, publicity, SEO, and advertising.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

The most significant leadership lesson that I've learned is the development of standard operating procedures (SOPs). They unlock steady growth because employees know where their responsibilities start and end. Thus, their work becomes more fulfilling because they know when they do a good job. They stay with the organization longer, create support systems internally, refine SOPs, and train new people. Clients then are happier because our work is better, so clients trust us to be better partners and spend more with us. The business grows.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Outliers by Malcolm Gladwell tells the story of how bad communication practices result in a plane crash. The co-captain saw an issue upon descent to land and communicated it to the pilot, but the pilot didn't concur that a problem was afoot. The co-captain didn't raise the issue further due to cultural rules on communication practices. There was an issue. The plane crashed. Had there been better communication, there would be no story. The lesson is that the nuances of how we communicate routinely have big impacts on the success of a business. As a result, we debrief on seemingly small issues so we can rectify them and change behavior so they don't become big issues.

 6. If you could only give one piece of advice to a young leader, what would you say to them?

Take time to learn the intricacies of the industry you are in. That can take years, or, in my case, a decade. Then, when you're ready, pounce on that idea.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

I was 29 and the Director of Digital Media for an ad agency. I had to be in meetings with far more experienced executives talking about work I knew well, but I needed to be more consistent with those meetings. Sometimes, I'd do moderately well; other times, I could have been far more effective. I didn't know how to handle myself in meetings. I was advised that I needed time and experience to improve in meetings. So, I took action and joined Toastmasters. In my nine months in Toastmasters, I have yielded dramatic results. I learned how to be a better speaker. We practiced giving speeches of multiple varieties during that time. That was a seminal experience in becoming a more effective leader, advertising executive, and businessman.

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