The Flexible Strategist (Strategy Talk with Matt O’Bryant)

Meet Matt O’Bryant, he’s the Director of Strategy at a  Providence-based web agency called Oomph, Inc. He helps to lead an agency, provide strategic direction for clients, and offers a number of insights into today’s digital sphere. Matt has had many roles in the tech space from web admin to project management to digital strategy. Our chat covers analytics, personas, business, and lots of cool tools to help with strategy. Let’s welcome Matt O’Bryant.

The Art of Asking Good Questions

Which questions should you be asking in your strategy sessions? That’s a good question, and the answer will depend on what challenge you’re trying to solve. But there are different styles of questions you should be asking your participants. Opening questions get you started and help you gather information. Exploration questions help you investigate, but also explore opportunities. Assessment questions help you stay on track. Closing questions let you close the loop and think about next steps.

The 3am Writer (Strategy Talk with Aileen McDonough)

Meet Aileen McDonough, she’s the owner of 3am Writers (, a creative communications firm based in Rhode Island. Aileen is a content strategist, consultant, and writer; she really loves creating content and gives some great tips in this episode. Listen to our strategy talk about content in the digital space; we cover content calendars, content strategy, social media, and more.

The Millennial Designer (Strategy Talk with Michelle Schulp)

Meet Michelle Schulp, she’s the owner of Marktime Media ( where she makes design frictionless. Michelle is a designer, front-end developer, and strategist. She gives talks in the WordPress and design communities, and is super passionate about design and technology. Listen to our digital strategy chat.

If you want to check out Michelle’s personal blog: