Helping CEOs Connect With Purpose, Mission & Creativity - IPaintMyMind Helping CEOs Connect With Purpose, Mission & Creativity - IPaintMyMind
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5 Questions That Help CEOs Connect With Purpose, Mission, and Creativity

5 Questions That Help CEOs Connect With Purpose, Mission, and Creativity

Written by:
Evan La Ruffa
Jul 22, 2019

There are so many driven people making huge contributions in the world today, but a lot of times it can all feel removed from real connection. The digital landscape has a lot to do with that, but so does the pace of life, and the rate at which innovation creates products, markets, and sectors. 

While our culture has often favored a workaholic approach to achievement, more and more of us are starting to catch on to the notion that we aren’t how much cash is in our bank accounts, and that enjoying how we spend our time and feeling connected to each other, is a huge indicator of happiness and fulfillment.

Thinking about how CEOs connect with purpose, or mission, can also feel removed when a company is trying to grow, is taking on investment, or has a lot of competition. CEO’s need to look at bottom lines, understand trends, put great people in a position to succeed, and at the end of the day, make a profit, of course.

That said, we all know that isn’t everything. Most of us, in fact, work hard to earn money so that we can spend it on culture: art, music, film, museums, travel, & food. All those categories are incredible inroads into missions that might move you, but there are plenty of other ways to unpack how your company can best serve a mission it’s aligned with.

Mike Duffy – CEO, Citybase

Helping CEOs Connect With Purpose, Mission, and Creativity

In our case at IPaintMyMind, the minute we met Mike Duffy of Citybase, we knew we had an ally. Here’s a CEO that is in the throws of building something that could change the future of how cities work and who is also super creative & expressive. 

When we explained how the art we lease to our clients helps us fund FREE art programs in schools, it just came down to finding the art in our collection that he loved the most! In that sense, we knew Mike was all about innovation + creativity, two huge data points for our team at IPaintMyMind when thinking about clients that will not only get the most out of our services, but also someone who truly believes in the future we’re trying to create.

In thinking about how CEO’s can connect with local causes, important missions, and creative projects, there are some questions I’d ask, both of the CEO and the company, that can help find a really great fit when it comes to giving back and playing your due role in the landscape of Corporate Social Responsibility.


Whether IPaintMyMind, or the variety of incredible organizations working to make civic life better, these prompts will help any C-suite leadership find a cause to support that will fit their personality, tone, & culture in a way that really does provide their company with something to believe in, together.

Write down your answers to the questions and you’ll be a lot closer to rallying your company around a cause that binds you and them to a great mission, and each other.

The 5 Questions are…

1. What are your companies pillars? And, why?

2. How would you describe your companies’ collective personality? We’re not thinking brand identity here, but more so the character & spirit of your employees. What do your employees care about? Do they skew creative? Technical?

3. Where in the world are you? What local issues can you help solve?

4. How could the skills the people in your company possess support a great cause? Anyone can pick up a hammer, but does your company have particular expertise that could bolster a nonprofit organization’s efforts?

5. What does a ‘beautiful future’ look like to you? What does it look like to your employees?

Final Thoughts

Whether art, education, civil rights, medical research, children’s issues, voter registration, or any other important cause, the answers to these questions will put you in the right lane.

Now get out there and make a difference! 

Interested in volunteering with us

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Written by:
Evan La Ruffa
Jul 22, 2019