Detail from Lock 8 on the C & O Canal

CEO as…Chief Conversation Officer?

Todd Gibby
Jan 21 · 5 min read

The CEO role can be described in countless ways. One definition comes from the Corporate Finance Institute, which states: “The CEO is responsible for the overall success of a business entity or other organization and for making top-level managerial decisions.” Accompanying that description is a list of the CEO’s roles and responsibilities, which is peppered with dynamic verbs such as: leading (X), creating (Y), communicating (Z), ensuring, evaluating, and assessing. Such a high-powered portrait of the CEO is unsurprising, especially given the commonly held notion that “real” CEOs should courageously lead from the front. And although Jim Collins’ classic book Good to Great introduced us to Level 5 leaders who are characterized as humble and reserved, the image of CEOs as vibrant action-heroes-in-board-rooms is a persistent and alluring one.

It is with all of this as context, that I was surprised in a recent board meeting when a CEO characterized his role in an entirely different way: as Chief Conversation Officer. “If you can create good conversations,” he offered, “You can create good outcomes.” This initially struck me as being a far more passive role-assessment than I’d expect to hear from an actual CEO. But, with its unwavering focus on delivering results (which is undeniably the responsibility of CEOs), this description resonated with me as being worthy of serious consideration.

Upon further reflection, I view this as an accurate and valuable addition to the responsibilities of the CEO. It is undeniably important for CEOs to foster effective discussions among a broad range of stakeholders. They need to create open dialogue with prospective customers in order to gain an informed understanding of jobs to be done. It’s imperative to cultivate candid conversations with existing clients in order to consistently improve products, inform future investments, address service issues, and avoid churn. A balanced and candid exchange with team members is crucial to enable them to perform, and to identify what obstacles stand in their way personally and professionally. And, finally, open dialogue with owners / investors is needed to align expectations and leverage their helpful perspective from above the fray of day-to-day operations.

Being a good conversationalist takes work; and not every CEO is naturally gifted in this area. Rather, the art of conversation is the subject of countless studies and far exceeds the scope of this post. But, as this previous post highlights, a bit of structure and a few simple practices can help CEOs up their game in terms of fostering effective conversations with consistency and intentionality:

1) What / How Questions: Effective CEOs hone the ability to consume, analyze, and process large amount of information very quickly. And, although this skill improves their efficiency in decision-making, it can also make conversations with CEOs seem more like interrogations. A few simple word choices can alter this dynamic and lead to far more natural and interactive conversations. When engaging stakeholders in conversations, executives should steer clear of yes / no questions and avoid starting queries with “why,” “why not,” “who,” or “how many.” Far better are questions that start with “what” and “how;” almost inevitably, starting with these words results in a question that invites real input and opinions from the responder. In her excellent post on how to manage 1-on-1 meetings, Mathilde Collin (Co-founder and CEO of Front) offers a list of questions she frequently asks employees — nearly every one of them starts with “what” or “how.”

2) The Power of “What Else?”: Two simple words. Used effectively, they form a question that is astonishingly powerful. This question is wide-open for responders to interpret in many ways: “what else is on your mind, what else do you think I should know, what else do you feel is important to say?” This short phrase can be a key tool in engendering the kind of trust that allows someone to share their (invaluable) inner thoughts, which can be far more insightful to the business than still more stats and figures. To be clear, tone / inflection / intent are all critically important here. This CANNOT be communicated either explicitly or implicitly as “what else you got?” This was the go-to move of a former boss; no matter how substantive our discussions were, he would conclude with the inevitable question: “Is that all you got?” Suffice it to say, that didn’t establish a strong foundation for productive conversation.

3) Silence Can Be Golden: People want to hear what CEOs think; and chief executives get comfortable articulating their thoughts for audiences of all sizes. But CEOs get less forced-practice in listening. This is particularly true as CEOs interact with stakeholders with whom they have less frequent contact. The expectation is that CEOs do the talking, others do the listening. In this dynamic, breaks in conversation can present themselves as awkward silences — which we as humans prefer to avoid. Although it may be counter-intuitive, good CEO-conversationalists lean into those silences; and the benefits can be profound. Giving someone the white-space to slowly open-up and share an important-but-inconvenient fact or opinion, could just prove seminal in informing a thorny decision.

4) Kill the Conversation Killers: We CEO’s are an action-oriented bunch (see points above), so it’s possible someone might read this blog and be tempted to rush headlong into a bunch of CEO-conversations. Don’t do it. Conversations are powerful things; and they can go spectacularly wrong for countless reasons. Thankfully, humorist and relationship writer Jessica Wildfire recently posted an incredibly useful roster of 10 Fatal Mistakes that Kill Conversations. In all honesty, I found this list anything but funny. Rather, I’ll sheepishly admit that at some point in my life, I’ve probably broken every one of these guidelines. But I don’t intend to repeat those mistakes. Likewise, this is a great list for any Chief Conversation Officer to keep handy and review from time to time.

This whole topic of CEOs as Chief Conversation Officers reminds me of the well known African proverb: If you want to go fast, go alone. If you want to go far, go together.” In today’s business environment where speed is rewarded, CEOs are wise to also remember to focus on going far, together. And that if you are going to travel far, it is always better to have good conversations along the way.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

Todd Gibby

Written by

SaaS operator-turned-investor | Founder of Lock 8 Partners | Sharing observations, thoughts, and lessons learned from the ever-educational journey.

Made Not Found

In SaaS businesses, operating results are earned every single day; and good businesses are made, not found. Writing here about building organizations, learning from the experience, and appreciating the ride.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade