The most impactful conversations aren't structured.
Lalena Kennedy via Canva
By C200 member Georgia Rittenberg
Many leaders have had the same experience with AI. It starts out of curiosity. You test it with a few simple questions, maybe asking it to plan a trip or suggest books to read, just to see what it can do. Then at some point, you see it could be used to solve real business problems.
For me, that moment came when I was trying to find a broken formula in a spreadsheet. Before AI, I would have spent hours combing through it cell by cell. I started down that path, but then the light bulb went on and I fed the spreadsheet into AI. Within seconds, it identified the faulty cell and provided a solution. What would have taken hours was resolved in moments, and it immediately changed how I thought about the role AI could play in my work.
Once AI makes itself useful to an organization, the CEO has a choice to make. On one side is the pull of possibility, the question of what else could be automated or accelerated. On the other is a more deliberate approach, using AI for what it does best while recognizing where human judgment, experience, and relationships still drive the most meaningful outcomes. The challenge is not deciding whether to use AI, but deciding how to use it in a way that strengthens the organization rather than flattening what makes it distinct.
The real advantage in any business has never been speed alone. It is the relationships that build trust, the context that shapes decisions, and the ability to understand nuance in ways that no system can replicate. How leaders choose to use AI will determine whether those advantages deepen over time or begin to erode.
As organizations continue to automate more of their processes, there is a growing risk they begin to lose what makes them distinct. When companies rely on the same tools and platforms, outputs start to look increasingly similar. Efficiency improves, but differentiation narrows.
I saw this while putting together a proposal for a new customer. AI quickly generated a general best-case scenario, but it did not reflect the customer’s specific needs. Their business required a tailored approach, and the output lacked the context to deliver that. It served as a starting point, but experience and judgment were needed to shape a plan that would actually work. AI made the process faster, but it did not replace the thinking behind the final decision.
That is where leadership matters. AI can accelerate early-stage work, but it cannot determine what is most likely to succeed. That responsibility remains with the CEO and leadership team, who must apply context, judgment, and experience to arrive at the right outcome.
The same dynamic applies to customer service. Few experiences are more frustrating than being caught in a chatbot loop with no clear path to a real person. When that happens, customers often look elsewhere.
We took a different approach when launching a new asset management platform. Built from customer feedback, we stayed closely involved and worked through issues directly with customers rather than routing them to automated support. What we heard consistently was that customers valued working with people who understood their business. Glitches mattered less than the experience of being supported.
Technology can support the customer experience, but it should not replace the relationships that sustain it. Organizations that continue to invest in those relationships will maintain an advantage that no shared platform can replicate.
The culture of an organization, and the success of each team within it, depends on the people who make up that organization. AI can play a useful role in the early stages of hiring. It can help generate ideas for job descriptions, identify potential profile fits, and even suggest interview questions. Job seekers are also using AI to refine their resumes and highlight their experience more effectively. These are all valuable uses of the technology. But hiring decisions require a deeper level of understanding that AI cannot fully provide.
In a medium-sized organization, the most valuable employees are often those who can move across roles, step in where needed, and connect ideas across teams. This adaptability is difficult to capture through keywords and is often overlooked by systems designed to match specific criteria. Candidates with non-traditional backgrounds, in particular, can bring insights that a more linear path does not reflect.
Leadership judgment becomes essential at this stage. AI can narrow a pool, but it should not define who moves forward. Humans need to engage earlier, review candidates more broadly, and identify qualities that may not be obvious in a structured format. Building the right team requires understanding how individuals will contribute over time, not just how closely they match a list.
The impact of AI extends beyond hiring. Many employees are uncertain about what it means for their roles, and without clear guidance, that uncertainty can affect morale and limit adoption.
Transparency is critical. Teams need to understand how AI fits into priorities and how it will be used in practice. When expectations are clear, employees are more likely to adopt the technology in ways that support both their work and the business. AI should be positioned as a tool that handles repetitive tasks, allowing employees to focus on work that requires insight, creativity, and direct engagement.
When used effectively, AI creates time that can be redirected toward higher-value work, including strengthening relationships and improving the customer experience. It does not diminish the human role; it expands it. Leaders must ensure this happens deliberately by reinforcing a culture that values both efficiency and human connection.
In a discovery call with a prospective customer, it is common to ask if the conversation can be recorded. It is just as common for the customer to agree, but the dynamic often changes. The conversation becomes more measured, and less information of real value is shared. As soon as technology is introduced between two people, a level of distance can form. The interaction becomes more formal, and the opportunity for candid insight can narrow.
The most impactful changes in my organization have not come from structured, recorded conversations. They have come from informal moments, such as a conversation over lunch with a customer or a discussion with an employee. From there, the dialogue continues with a phone call or a video conversation that is not recorded. By the time a formal meeting takes place, the foundation has already been built. The recorded conversation tends to focus on confirming decisions and documenting next steps, while the real understanding has already been developed through direct, human interaction.
This is where leaders need to be intentional about how and when technology is used. AI can play a valuable role in preparing for these conversations. It can help distill information about a customer, create a framework for a proposal, or analyze similar companies that may be a good fit. Tasks that once took days can now be completed in seconds. That efficiency is meaningful, but it is only the starting point.
The time gained through AI creates an opportunity. It allows leaders and their teams to focus on what drives the strongest outcomes: building relationships, establishing trust, and working together to develop solutions that reflect the full context of a situation. Technology can accelerate the process, but it is the human connection that determines the quality of the result.
For CEOs, the advantage is not in how much work AI can take on. It is in how that time is reinvested. Organizations that use AI to create space for deeper engagement, stronger relationships, and better decision-making will continue to stand apart.
C200 member Georgia Rittenberg is the CEO of ComputerCare, a provider of comprehensive IT Asset Management (ITAM) services and certified hardware repair for Apple, Dell, HP and Lenovo devices. She began her career at ComputerCare in a part-time customer support role, eventually moving into sales and continuing to learn about the business from her colleagues.
Under her leadership, first as President and now as CEO, ComputerCare’s employee base has grown by 120% globally. Georgia would have an open-door policy, but there’s no door at her workstation. When she’s not at her desk, you’ll likely find her in the shipping department breaking down boxes.
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