Every morning you get up, get dressed, down a cup of coffee (or several) and mentally begin running through the to-do list in your head. There are clients to visit, phone calls to make, emails to wade through, a new vendor who needs just a minute, bills to pay, orders to check on, a sales position to fill … and the list goes on. Before you know it, it’s getting dark outside and, if you are lucky that day, you’ve ticked off a few of the most pressing items on your list. The next day and the next and the next flicker by the same way like a scene from Groundhog Day.

When do you stop and really think about your business and where it’s headed? And when you do take the time to think about the bigger picture, what are the blunt, provocative and often uncomfortable questions you should be asking yourself? Are you willing to rock the boat?

Fifteen of the industry’s most successful business owners and visionary leaders lay out the questions (in no particular order) they think are most critical to those who want to think strategically about what’s next. To this list I’d add one more: If my company/product/service wasn’t around any longer, would anyone miss it?

Asking these types of candid, open-ended questions is a proven way to release your thoughts for deeper creativity, problem solving and goal setting. If you are not yet asking yourself questions such as these on a regular basis, consider the opportunities you may miss if you don’t. A suggestion is to ask yourself one new question every week. Add it to your to-do list, if you must.

Ira_Headshot_alt web

1. “Do I know what it takes to make or keep the business successful? Do I have the energy and the resources to make it happen?

Ira Neaman, President, Vantage Apparel

Emmer Headshot 2911 web

2. “Do I really know what business I’m in, or am I confusing what we use with what we do?”

Gregg Emmer, VP and CMO, Kaeser & Blair

Elizabeth Tate web

3. “How will we balance the online shopping habits of our clients with the brand standards required by their employers and the product safety standards required by the government?

Elizabeth Tate, CAS, Chairman/CEO, Signet, Inc.

Francesco Indrio web

4. “Web sales or personal sales? Alone or in partnership?”

Francesco Indrio, CEO, Alpi International Ltd.

Indrio explains: “I chose these two questions because I don’t even have an answer for them. Today things have changed and the internet is causing people to shorten their attention spans. In other words, previously one could make a presentation to a customer and rely on a certain amount of personal communication. Today, both distributors and suppliers tend to have a split second of the customers’ attention through electronic media. Previously the quality of the product and its characteristics could be explained at length. That tends to not happen anymore. The distributor who shows his wares online can only rely on the moment in which the end user clicks on an item, so he has to have all the information there at the customer’s disposal before the customer clicks on something else. And often the supplier has to provide that information so it can be seen, selected and used in that split second. It is a new and fast-changing world out there.

Jeff Batson head 1 web

5. “What skill sets will my business need in three to five years?”

Jeffrey Batson, CAS, President, Next Products, Inc.

Ross Silverstein

6. “At this point in time, what things matter most for the success of my company? Do I have the right people to get the job done quickly, effectively and optimally? If not, what am I going to do about it?”

Ross S. Silverstein, President & CEO, iPROMOTEu

Mary Jo Tomasini2 web

7. “When my customers choose to buy from someone else, what (other than price) is the motivator?”

Mary Jo Tomasini, MAS, CE Competitive Edge, LLC

Jim Franklyn

8. “What are the three most important things we need to offer decision makers who want to buy promotional products in 2016 and beyond?”

Jim Franklyn, VP of Sales and Marketing/Partner, InkHead Promotional Products

9. “How do we stay relevant in an industry that is becoming ever more affected by advances in technology?”

John Houlding, President, Cotton Candy, Inc. (no photo on this one)

Jim Hagan web

10. “Would my customers refer/promote our company to others?”

Jim Hagan, Chairman, Sweda Company LLC

Hagan adds, “I think about this one every day.”


11. “How do I continue a consistent growth trend?”

C.J. Schmidt, President, Hit Promotional Products

RosPlummer web

12. “What is more important: increasing my actual revenue or my actual profit?”

Rosalind Plummer, MAS, V.P. Sales and Marketing, Clearmount

Jon Isaacson web

13. “What is the single biggest opportunity and what is the single biggest risk to my company in the upcoming year?”

Jonathan Isaacson, CEO, Gemline

Bonni Sandy web

14. “How am I going to go to market?”

Bonni Sandy, CEO/President, Dard Products, Inc.

Sandy explains: “[These are] your key points that separate you from everyone else.”

Joe Fleming web

15. “Are we addressing the real needs and wants of our customers?”

Joe Fleming, President, Hub Pen Co.

Fleming explains: “What we perceive as important may not be what’s important to them.”

Got A Question?

What are the smartest questions business owners should be contemplating? Tell us at PPB@ppai.org and we’ll share your thoughts in an upcoming issue.