One of the most enjoyable parts of my job is meeting with CEOs and founders of organizations. As storytellers for confident brands, it is our responsibility to understand what organizations do, how they do it and whom they do it for. But, conversations with these business leaders provide an opportunity to understand a brand at a much deeper level. These conversations, along with a variety of other research and discovery techniques, help us discover the true soul of the brand — or, as we say, the moral of the story. And that is the foundation for great storytelling.

After conducting countless interviews, I’ve discovered a few key questions that make these conversations insightful, revealing and, most of all, fun. So, if you want to get closer to discovering the soul of a brand, try asking these questions to the brand leader(s):

1. What happened in your life that caused you to start/join [brand]?
Whether it was a personal/family-related event, a situation with a former organization or you joined the company as an intern 20 years earlier, a backstory can tell you a lot about leaders and their unique views of the organization. And, it often brings back many relevant memories that are shared within their story. Let them go off on tangents; it can often reveal the most unexpected information.

2. What gets you most excited about coming into work each day?
The response can help you understand priorities of the organization from a more personal perspective. If the leader is excited about what he will discover, then innovation is likely core to the business. If he is excited about meeting with customers to help them understand/overcome challenges, then solutions/service may be important. Remember to let them do the talking. The more you listen, the more they talk.

3. What keeps you up at night?
Aside from sleep apnea, drugs and newborns (all of which I’ve heard in response to this one), the answer to this question often reveals the greatest fears of the business leader — but in a more fun, approachable perspective. To contrast this, if you simply ask, “Who is your biggest competitor and why?” then you do not necessarily know if they are truly concerned with that competitor and/or what the real issues that they are worried about are. Keep the questions open ended so they have room to go where you may never think to go.

4. Tell us about the most exciting experience you’ve ever had with this organization.
If you are looking to create a great story, then why not ask the business leader to tell you one themselves. It is another way to truly understand what motivates them and gets them excited. If the mood is right (i.e., you’re both having fun), ask them for their most frustrating story as well. Listening to emotionally charged stories often opens the door to a completely new area of exploration and insight.

5. What is the moral to your story — the core belief that defines who you are?
This one is often best saved for the end of the discussion — after they’ve had some time to look inside themselves from your questions. It can require some set-up, but, if you can get leaders to reveal a core belief (or several key beliefs) that most define who they are, you are that much closer to the moral for their brand. And, when they begin thinking about their own morals, they will immediately begin thinking about the moral for their brand, too.

As always, please share your thoughts and comments – and feel free to add to this list.
PS.  We enjoy these conversations so much that, beginning in September, Small Army will be offering a free half-day session to a worthy non-profit each month to help them reveal the moral to their brand story. For all the reasons noted above, key leaders of the organization (i.e., Founder, Executive Director, Board Members, etc.) must participate to be considered.  If you know a non-profit that is interested in applying, please have them complete this short form on our website.