The Executive Voice

What is Conversational Stewardship? Why Should You Care?

According to this HBR article, “conversational stewardship is the ability to intentionally shape group conversation.”

“Conversational stewardship means intentionally caring for the quality of the group’s dialogue. It involves creating clarity about why the group is meeting, who is responsible for what during the discussion, and how to foster an environment where people feel comfortable contributing honestly—even when things get difficult.”

And it’s the leader’s job to steward conversations, whether you’re the CEO, part of the senior leadership team, or a line manager.

To be clear, it’s not about taking charge of the conversation or dominating the agenda; it’s about skillfully manoeuvring conversations to drive the best actions and outcomes for the business.

I’ve attended too many meetings where the purpose and the attendees' roles aren’t clear. Fundamental stuff, but undirected conversations are a common time-waster and morale killer. Again, it’s the leader's job to fix this.

Creating an environment where others can speak openly without fear, is, in my opinion, the biggest problem leaders need to tackle as part of stewarding constructive conversations. This is because ‘self-preservation’ naturally kicks in when leaders are present - most people will not speak up or be truthful as no one wants to lose their job or be humiliated if a leader disagrees. Yet the ability of a leader to guide frank and fearless conversations is what allows for the solving of difficult problems or the freedom to engineer solutions that deliver big financial rewards.

Skilled conversation is both an art and a science, and all business professionals should continually practice it to improve. If you’re in leadership, though, the stakes are higher: You’re managing the financial health and well-being of your organisation, therefore communication competence is mostly about effectively ‘directing’ conversations.

The best way to do that is to focus on answering the following questions:

1.      What is the purpose of this conversation? What are we trying to achieve?

2.      Who does what? Who is accountable for results? Who plays a supporting role?

3.      How am I, as the leader, making it safe for people to disagree or challenge the status quo? And how do I ensure constructive disagreement doesn't turn ugly and become destructive?

The above is simple yet hard to do. Still, leaders who consistently apply conversational stewardship get more value and ROI from the people in their organisation.

Communication That Earns Influence

The Biggest Obstacle to an AI Sale May be Conflict Inside the Customer

Gartner’s 2026 tech-buying study says 68% of buying teams experience unhealthy conflict when it comes to AI buying. Those teams experience three times as many project delays and are seven times more likely to regret the purchase. Reactive AI purchases pushed by boards or CEOs are particularly prone to conflict.

This means that as the seller or member of the pursuit team, it’s not so much about answering the question, “Why should you buy our technology?” It’s more: “Can we help your organisation agree on what it’s trying to accomplish?”

According to Gartner, the CIO is the role most likely to “drive consensus and high-quality deals.” This is the role you should be courting the most and reflects my recent experience that technical experts are playing a more dominant role in the sales process both at the seller and buyer organisation.

At the same time, understanding how to manage buyer dysfunction is well suited to the strategic seller role (rather than technical folk) as the sales department spends more time analysing psychological buyer motivations, biases, fears, as well as surfacing internal politics and stakeholder agendas at the customer.

A winning pursuit team therefore combines strategic sellers with expert engineers who operate as a functional, collaborative team. Both parties need to understand the evolving role of the CIO at the buyer and how to build a trusting partnership with that individual. The strategic salesperson leads the political discussion, and the senior engineer manages the technical discussion, though both need to be fairly adept at doing both.

This, of course, doesn’t mean the pursuit team doesn’t work to build a relationship with the buyer's CEO or CFO, and others like Procurement; it’s important they build relationships with all key stakeholders. The point is, according to Gartner’s research, that the CIO may hold the keys to the kingdom more than other decision-makers traditionally have done so in the past.

This is a bit of a mind shift for tech sellers and pursuit teams.

While most tech vendors I’ve worked with often chase the CIO, it’s not for their consensus building skills but because vendors think the CIO will better grasp the potential of the tech.

Just understand your energy should go into helping the CIO bring their organisation together to agree and not just influence them on the type of tech solution you’re trying to sell. I emphasise this because we still talk at length about the technology while not giving equal attention to the political games being played at the buyer.

OpenAI & Anthropic: Communicating When AI Goes Rogue

Reuters reports OpenAI agents used at least 10 previously undisclosed websites for unauthorised communications, with some incidents apparently not made public for months. Meanwhile, Anthropic has disclosed a fourth cybersecurity incident involving an early Claude model and brought in independent researchers to investigate. Same problem, different communication response.

The Subtext
As increasingly autonomous AI creates new risks, transparency about failures may become as important to trust as the technology itself.

Phrase of the Week

Digital Sovereignty: How much control does your organisation really have over the technology, data and infrastructure it depends on? Digital sovereignty is the growing push to reduce dangerous dependencies without pretending organisations can become completely technologically self-sufficient.

Helping Someone Bring a Divided Room Together

Whether you’re aligning your own team or helping a buyer build consensus, the right questions can dissolve enmity and unite different perspectives.

And when advising buyer stakeholders like the CIO, it’s always good to start the conversation by saying, “Would it help if we asked these questions?” Rather than, “I have some advice on how to build internal consensus”. The latter is patronising, while the former is collaborative.

If this helped you think differently about communication, forward this newsletter to someone who leads, sells or explains complex ideas in tech.