Your Initial Executive Client Conversation

For an executive who are looking for insights on what others ask or think their current technique may need adjusting, below is a brief overview of common questions independent executives walk through with clients.

Whether you are a novice to the process or have been doing this most of your career, every executive has their own spin and techniques that work best for them.  Let these common questions be a guide, not a script.

Weave these questions into the conversation. Don’t do all of the talking, and try to go through only the questions that apply to the client’s situation. When the discussion is one-sided, it is more difficult to bond. Instead, listen to their pains and bring up appropriate questions that will help you better understand. Give them a chance to talk about themselves and their company. They need to know you are listening to what they are saying.

Let’s take James as an example. James was going to be meeting with a client, so he did a lot of research about the company and the owner. When James got to the meeting, instead of listening, he immediately went into a whole monologue about how much he knew about the client. The client was not impressed. First of all, he was not given a chance to talk. Secondly, he wanted to discuss how to grow his company to the next level; he didn’t want to hear James brag about how much he knew about the client and his company. Needless to say, it did not go well. The owner later bonded with another executive who did listen to him.

Conversely, Denise had a CEO client who had a very short attention span and did not want the meeting to go over an hour. The CEO had never hired outside help and was nervous. The meeting ended up lasting more than two hours. The client was so engaged in the conversation that she barely realized that two-and-a-half hours had already gone by. It was a seamless conversation between Denise and the CEO. Denise even used future-oriented language during the meeting, such as, “Next week, we can start working on what you just mentioned.”

How an executive comes across to the client is extremely important. The initial conversation can make or break future meetings, even if you aren’t meeting initially with the decision-maker. Although the person you are speaking with may not be making the decision, he or she often can influence it. The more natural and stimulating the conversation is, the more successful you will be.

When you are first starting out, sometimes the conversation isn’t as natural as it could be. Below is an array of questions that can help you jump-start the conversation.

Once it starts to flow, you can then reference your list at the end to see if anything was missed.

General Questions asked by an executive

“Tell me how you started the company” or “Why did you decide to take this position?” This can help set them at ease with easy discussion and the history of it might become important.

  • What’s the history of the company?
  • What’s the history of the current CEO?
  • Describe your company culture for me. This question allows you to see the company’s core values.
  • In ten years, what is the headline story of the company?

Future Plans and Goals

  • What are the goals for next year?
  • What are the goals for company long term?
  • Where do you want to take your company?
  • How big do you want to grow your company?
  • In what period of time do you want your company to grow to that size?
  • What would you do with $1 million? This question lets you see if they have a single key predictive indicator; if they invested in this area, would it contribute this much to the company? Also, it lets you know if they have a weakness they want to shore up or an opportunity they want to push.

Current Status

  • What one word would your customers use to describe your company? This helps you to understand why customers buy from them and what emotional connection or brand connection the company has with its customers. Also, ask why customers would buy from them versus competitors.
  • How are they different from other businesses/ competitors?
  • What are they looking to achieve if they had extra expertise? What type of expertise would that take?
  • Do they hold trademarks, patents, or licenses?


  • How would you rate your management team? As, Bs, Cs, Ds, or Fs? If they say everything is fine, ask them to use the following criteria: “Knowing your managers now, would you rehire them?” Different answers may come out.
  • How would the company run without you? This tells you whether the person is in the business or leading the business and whether the leader has the right people who can and will make great decisions.
  • How does your management team know at the end of the day/month/week whether they met their goals? This tells you whether they have dashboards, focus, and alignment.

Executive Needs in Your Specific Discipline

For example, if you are a finance executive, you are looking to understand more detail on who the players are, how it works in the client’s environment, how it supports the business as a whole, and so on. Many times, you’ll gain more insight through how they answer and what they focus on rather than the details they share.

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