Common Question: What Questions Do I Ask Executives?

“What questions should I ask when meeting with an executive?” This question came up about three times last week during various marketing events, coaching calls, and emails with clients – “Can we put together a list of questions for the sales team to use when talking to executives?” I usually get this question when talking about Marketing Events and Demand Generation follow up – that’s about the only time I see sales people really engaging with executives in a proactive discovery process.

It feels better to have a list of questions – a list of 5 to 7 questions that can be read from a script, with a place to record answers. But don’t expect this to actually work. If it were that simple, sales people would be in front of executives with a list like this all the time. My experience is, once you pull out the list, you’ll lose your audience’s attention. One size can’t fit all – and if you need a list, it’s clear that you don’t do this very often. Imagine pulling out a list to ask your spouse how their day went. What would they think? Well, they might wonder if this were a conversation or a project for school?

What Questions Should I Ask?

Instead, I recommend using a framework. A series of topics that guide the conversation. This framework has to be second nature – memorized. This takes some practice. In my book, The House & the Cloud (available for free as a PDF from my blog sidebar), I provide an example of a security focused discovery conversation. I start out by exploring things that my client feels are critical to their business. The heading reads, “What are you trying to protect?” But the essence of the question goes much deeper – because its not really a question; its a framework. I am searching for those applications and data repositories that contain highly valuable data. It might be client data, intellectual capital, or some application that allows the business to work ten times faster than it would if certain work were done manually.

The second line of questioning focuses on threats. “What would threaten these critical systems?” This requires some give and take. The client may not know how to answer this – the sales person might need to explore this with the client, coming up with possible threats based on the business vertical, type of data, cybercrime trends, or current conditions of the business (for instance, on the cusp of some new invention.) The final area deals with the company’s ability to detect a problem before it’s too late. This is a shorter question. At this point, the sales person would have most of the data they need, but would want to know how comfortable this particular “Asset Owner” (as I describe in the book) is with their company’s ability to see into the network. Don’t confuse this with a technical question about intrusion prevention software. What you’re looking for here is a clue as to how safe or vulnerable this asset owner (who owns some level of liability) feels with regard to their data and applications.

How Does A Sales Person Learn This?

How does a sales person master this process? The simple answer is, “training and coaching”. Unfortunately, at least in this industry (technology sales), companies have substituted product knowledge for sales training. Knowing your product is necessary, however, product knowledge is not sales training. The executive discovery process is something that takes practice. It’s intimidating to walk into a business owner’s or VP’s office. One bad meeting with a CIO might be the final nail in the coffin for a promising account. But what if the sales manager were to set aside time weekly, during the sales meeting, to run through a few tips and to have a couple of people practice? What if it were part of the regular routine to provide new insights and experiences shared by other team members? Perhaps you could master this skill.

Getting Started

A great conversationalist has a skill – and great sales people need this skill. When it comes to working with executives, and working through the discovery process at that asset owner level, there is no substitute for having been trained and coached on executive level conversations and interview skills. Here are three things you can do right now to get started:

1. Read the CIO journal section of the Wall Street Journal – be able to discuss trends such as cloud services, BYOD (Bring Your Own Device), social business, and information security, and be able to make application to business.

2. Read the books other executives are reading. This might require you to ask around – which can’t hurt. Recent books by Jim Collins are always a good place to start.

3. Practice…look for people in social settings and push yourself to listen and learn from them. Ask questions about how they got into their profession, what has made them successful, how they would advise a young person entering their field, and what cautions they might give to someone entering that field. People love to share their war stories.