"What keeps you up at night?" Don't ask this question to a CEO!

"What keeps you up at night?"
Don't ask this question to a CEO!

You might be lucky and get an answer; however, I want you to know that you take the risk of a very short meeting. (I learned this the hard way).

1. When you meet with senior executives, you'll need to adjust your messaging accordingly, depending on the situation and audience. You want to lead the discussion based on your fundamental messaging and ensure they "understand that you understand".

2. If you have done your homework properly before the meeting, you will build stronger rapport and trust if you let them know that you are up to date on the different change drivers, key Initiatives, and most acute pain they are looking to solve.

3. Feeling uncomfortable talking about the macro/micro trends and the different changes that are going on in their sector? In that case, you will most likely end up talking about what you are comfortable talking about, i.e. your products, benefits and features.

"Let me introduce you to Stephan. He knows everything about this technical stuff..."
When you manage to get a meeting with a senior stakeholder ”high up in the building”, and you start to talk about your company and your product before you have "earned it", you will most likely "be sent down in the elevator" to meet with people (like Stephan) further down in the organisation. Its nothing wrong with talking to Stephan. On the contrary, you should speak to him and his colleagues, but not at this point.

4. If you cut corners and only address the steps linked to change drivers, pains and crucial initiatives and jump straight to presenting your solution - you will risk that your counterpart misunderstands you and place your solution/product in a bucket based on their experience and knowledge. We call this issue "category confusion". If they put you in the wrong bucket, I guarantee you will have difficulties getting your solution or product "out of that bucket".

This and much more can be summarised in the attached picture and the following brilliant quote that I have borrowed from my rainmaker colleague and the father of the Megadeals discipline, Christopher Engman:

”There is a linkage between the decision tree and how big corporations are organised, structured, their focus and how they make decisions.”

When you nail the Fundamental Messaging (on the left in this picture), it will transform the win rate of your team and company.

// David Klättborg