What a CIO Wants: How to Approach a Sales Meeting

As a CIO, I’m constantly thinking about how to leverage technology and tools to drive the business, improve operational efficiency, and cost savings, boost customer experience, and drive revenue growth. I don’t view sellers as just vendors but as growth partners. So when you’re selling to me, I’m trying to establish three key points:

● How can you add value to my business?

● Is your solution driving a critical capability the business needs and has a competitive edge (unique IP, attractive pricing model, value commitment)?

● How can we create a win-win that serves us both? Can this evolve to a strategic partnership or is this a one-off transaction?

Before you enter a meeting with a CIO, I encourage you to think about how you’d answer the above questions. It is key that you demonstrate a clear understanding of not just your own product or solution, but also how it ties to larger technology and business objectives.

Regardless of what you’re selling, at the end of the day, we’re all human beings representing different interests. The ability to establish trust is highly important – the mark of a truly skilled salesperson. Trust can be broken down into the three Cs: character, capability, and chemistry, in that order of importance.

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Character – How You Do Business

Are you true to your word? Do you demonstrate personal integrity? I’ve turned down proposals where someone has shown high capability as well as a great product at a competitive price but questionable integrity. In my experience, this often causes more harm than good to the business in the long term. So if you’re a salesperson, make sure you’re representing yourself honestly to the people you’re meeting.

Character reveals itself in the way you respond to questions that may come up during your meeting. If you don’t know the answer to a question, it’s okay to say “I don’t know but I will find out and get back on this later” or “this is not a part of our offering right now” instead of saying things that are factually incorrect for the sake of gaining business.

When I’m meeting vendors, I do my research and often ask questions I know the answer to. This is my way of “testing” whether the salesperson I’m meeting can be honest with me, or will say what they think I want to hear. When asked questions, be truthful. Senior leaders with experience can sniff out disingenuous responses. If you’ve promised to get back to the CxO with more information, do so in a timely manner without requiring reminders.

Another watch-out: it never reflects well on you or the company you’re representing if you bad-mouth the competition – be it yours or your prospective client's. Similarly, if the organization you're selling to has an IT procurement team, it may come across as disrespectful if you bypass them and sell straight to the CIO. Being respectful of individuals and processes speaks highly to your integrity as a salesperson.

Capability – What to Include in Your Meeting to Stand Out

If you’ve asked for an hour of my time, I expect you to have done several hours of research prior to our meeting to truly understand my business. A lot of this information is publicly available, and contextualizing this with case studies, industry trends, and white papers is important.

Since you’ve booked the meeting with the senior leader, the onus is on you to come up with an agenda. You could send reading materials ahead of time so you don’t spend the meeting going through endless slides – I find this incredibly boring. Instead, cut to the chase, and address the three key questions outlined in the previous chapter.

I’m also put off when the salesperson uses the majority of our time together to ask me questions about my business and the challenges I’m facing. It’s not your client’s responsibility to educate you on their business. Do your homework beforehand.

A good rule of thumb is to spend 50% of the meeting asking insightful questions, the answers to which cannot be found publicly, and the remaining 50% sharing some interesting insights with me. A senior leader will always enjoy speaking with someone who is a subject matter expert and can hold conversations around technology and their business application.

Share Interesting Cross-Industry Insights

One meeting I’ll always take is one in which I expect to learn something new. So focus on how you can deliver the highest value in your first meeting with the senior leader. Tell me about the latest technology that might be useful to the conversation, any relevant learnings or best practices you’ve observed, or interesting case studies you’ve developed in different industries. As an industry leader, these kinds of insights will always interest me. For instance, I’m in the FMCG world, but if you share relevant learnings from the banking or tech sectors, I’ll sit up and pay attention.

Case Studies

Doubling down on case studies, I think they’re a crucial way in which a salesperson can validate their solution. I never buy anything based on a well-designed deck alone. It’s the real-world applications that I’m most interested in. When people share case studies, I often ask them what the challenges and pain points of implementation were. Every salesperson knows what the benefits of their solution are, but as a CIO, I need to know whether the person I’m speaking to is able to provide me with a balanced perspective that represents both sides of the coin. Every transformation comes with its share of pain, so being able to articulate the potential difficulties we should expect during implementation is a powerful differentiator.

Have a Long-Term View

When I’m meeting with a salesperson, I’m also trying to understand whether they have the right influence in their organization to deliver value on this deal. That is, if we give you our business, will you be able to meet commitments to come through in terms of timelines and quality expectations or will you sign the contract and move on to chasing the next dollar? I would much rather work with a trusted partner than a transactional vendor. So as a salesperson, it’s worth thinking about how you’re communicating with your client, and showing them that you’re committed to creating a win-win outcome and shared growth. Never over-promise or oversell for short-term gains, it erodes trust.

Chemistry – Connect with Ease

When you’re meeting a senior leader, it’s always worth doing your research into them personally. What are their hobbies, interests, and experiences? If you find that there are overlaps and that you share certain interests in common, it’s definitely worth bringing these up to build rapport. Don’t force a commonality where it doesn’t exist, but even something as similar as having children in similar stages of life can be a way to connect with the leader in a more seamless way. This is not mandatory but is great to have, as it makes doing business together a whole lot more enjoyable.

Demonstrate Integrity

Don’t fall into the trap of overpromising, sharing false information or saying yes just to please the senior leader you’re meeting with. Being truthful is a sign of character, and your honesty will only ingrain trust into the relationship you’re building.

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Showcase Interesting Insights and Case Studies

Don’t waste the CxO’s time by asking endless questions about their business that you could’ve found with an online search. Instead, share relevant cross-industry insights or case studies that add value and teach them something new. That’s memorable.

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Have a Balanced View

Don’t just sell the benefits of your solution. Spend some time highlighting difficulties and issues you’ve noticed in implementing your solution in the past to show that you are truly committed to delivering value to our partnership.