How to Talk to a CEO

Vikas Joshi
August 6, 2020

Talking to a CEO boils down to this: Think and feel C-level before you talk to C-level. If you are nervous about selling an idea to a CEO, take three minutes to read these three tips that will help you put yourself in the right frame of mind. These tips work whether you are talking to the CEO of your company or of a customer firm. The idea you are selling could be anything. Maybe you want them to buy your product, engage your company’s services, or hire you. Or maybe you want them to approve an investment, bless a change proposal, or promote you.

Of course, we all know a thing or two about CEOs — they are busy, they want you to get to the point quickly, they can smell BS from a mile away, they care for results more than effort, they want to know ‘what’ and ‘why’, not ‘how’, they often want numbers more than words. All those things are relevant. Let us treat them as given. Once we get that out of the way, we turn to more subtle aspects of interacting with the corner office. I frame effective CEO interaction as a set of three related but separate issues.

Put Yourself in a Learning Mindset

This is the most counter-intuitive thing to do while trying to sell an idea to a CEO. Most people think to themselves — I must impress the CEO. I must get all the value points across. I must cram as much as I can into the half hour I have with the CEO about my product, my company, my proposal, or my resume, right?

Not really. Several years back, a tech firm in Santa Clara used our company for engineering services. Their CEO called me for a discussion on how we could grow our engagement. I prepared a long presentation on our tech skills and project management capabilities. As we sat down to talk, he let me barely finish the first slide and then asked how long I had been running the business. By the time I could answer him, he had the next question. From where did we source our talent? I was getting impatient to get back to my painstakingly prepared presentation. I was sure it would make him want to buy more. And he kept on asking about our headcount, hiring policies, revenue growth, customers, and other irrelevant stuff. Then he popped the question that I should have seen coming: What will it take for you to sell your company?

That’s often the case. The CEO’s goal or priority is A, you are prepared to say B, and you want to press on, without bothering whether and how B helps A. This happens because you know what you know, whereas you can only guess what the CEO wants. All you have is a hypothesis based on limited information. What I ought to have remembered is — I am here with the CEO to validate A, to refine A, and to get a better sense of A. Then I should adapt B accordingly.

The only way to make what you say relevant to the CEO’s goals and priorities is to adopt a learning mindset. That means you are listening as intensely as you are speaking. Every minute the CEO spends talking, you may be getting closer to success. If you don’t reach the end of your slide deck because the CEO was already thinking ahead, that can be a good sign.

Truly Care for What Matters to Them

You want the job. You want the sale. I get it. Unfortunately, that is not reason enough for the CEO to give it to you. They want to know that you really care for what matters to them. How do you know beforehand what matters to them? That brings us back to A, their goals and priorities.

The CEO’s goals and priorities are dictated by their constituents — investors, customers, internal stakeholders, regulators, and so on. The relative weight of these constituents will vary greatly depending on the firm’s funding, size, org design, and industry.

I recall a discussion with a CEO of a large private equity funded enterprise software company in Boston. They were formed by rolling up several successful companies, each having a customer base in their target industry vertical and geographic region. The key to strategic success of the combined entity was to get all products on a common architecture platform, to ensure full interoperability between related products, and to get all sales teams committed to cross-selling other products into their current customer base.

My initial hypothesis in pitching to this CEO was that he first wanted to eliminate redundancies and ensure a healthier P&L of the combined entity. He would then want the customers to see the combined entity as a single source of enterprise software in their niche. Finally, he would worry about having the people get along with each other.

As the meeting progressed, I realized something that I had not appreciated back then. The real problem was to manage the egos of all these successful leaders that had come together after acquisition. Divisional P&L leaders justified every resource they controlled and asked for more, CTOs would not agree to a common architecture except in principle, and sales leaders only paid lip service to cross-selling.

Armed with a clearer understanding of the CEO’s goals and priorities, I was able to come up with product engineering ideas and integration workarounds that could minimize friction. Those ideas were a bit amateurish, but they sparked further discussion, and at the end of the meeting the CEO had the comfort of knowing that his vendor cared for what really mattered to him.

Make it Easy to Get it off Their Plate

CEOs are like the client piece in http protocol. They like an ideal world in which they can post a request to the server and forget about it. They don’t want to be worrying about it anymore, if they have their way. That frees them up for the next thing.

I recall a product OEM integration discussion with the executive leader at a tech company in Ohio. The idea was straightforward. We owned the intellectual property rights of a piece of software that would fit nicely into their enterprise software. It could potentially help them sell more, and every time they sold one of theirs, we could get a small cut of the sale as a royalty for ours.

As the meeting progressed, I kept hearing a curious expression that was unfamiliar to me at that time. We would talk about something and this leader would say, ‘That is a Phil decision’. And again, ‘That is a Ted decision’. And once, ‘That is a Cupertino issue’. Eventually it became clear that this organization had clear boundaries in decision making, and the leader was trying to figure out who to send my proposal to. I was making it harder for him by embedding several elements in the proposal that required signoff from many people. It was increasing his work.

Had I known better, I would have first figured out which part was the most critical to get started, and only made a proposal that he could simply forward to one of these internal stakeholders to get the signoff. That was my learning. A meeting should ideally end with the CEO identifying a clear owner and getting the thing off their plate.

Those are the three lessons I learned about interacting with the corner office: Put yourself in a learning mindset. Truly care for what matters to them. Make it easy to get it off their plate.

Before we march off to the next meeting, let me add the caveats. Every CEO is different. Most CEOs are work-in-progress at different stages. They bring their prior job experience to the CEO job and find it hard to let go their prior specialization. Then there are industry-specific and cultural differences across geographies. Finally, just like the rest of us, they are human, and they have good days and bad days. Which means, outcomes vary.

This article was inspired by a virtual roundtable with senior leaders at Harbinger Group, where I serve as CEO. Do share your thoughts and experiences of talking to corner office execs. I would be curious to learn from your insights. Good luck.