Developing and sustaining a ‘culture of conversation’

A healthy organization requires intentional focus on the quality of workplace conversations.

Relationships are the beating heart of all healthy organizations, no matter the size, industry or sector. Our mutual friend and parallel entrepreneur, David M. M. Taffet, describes it simply like this: “Everything in life happens with and through people.” Understanding how to run a healthy organization depends upon one’s embrace of this credo. In short, healthy organizations prioritize individuals above job titles.  

Individuals thrive when they form meaningful relationships, and meaningful relationships are formed and sustained through high quality conversations. Whether in-person, online or in writing, conversations are the connective tissue of human relationships. 

Unhealthy relationships usually suffer from communicative dysfunction, things like not listening to one another, hoarding information, making demands, lying, gaslighting or passive aggression. Developing a healthy organization requires intentional focus on the quality of workplace conversations, or a “culture of conversation.” 

Technology can’t solve this problem 

A culture of conversation encompasses much more than the practice of good communication etiquette. At the enterprise level, we’re talking about a broad approach to internal communication and decision-making that relies on transparency, thoughtful consideration of diverse perspectives, and the democratic sharing of ideas across departments, verticals and levels of management. At the one-on-one level, we’re talking about an approach to work that seeks to understand a colleague’s values, preferences, triggers, and character traits, not just their function or utility. 

What we’re proposing may sound basic, but if it is, why are so many organizations missing the mark? 86 percent of employees cite lack of effective collaboration and communication as the main cause of workplace failures. Furthermore, at large companies with more than 100 thousand employees, the cost of ineffective communication is an average loss of $62.4 million a year. But, instead of addressing the underlying issue, many organizations simply slap a Band-Aid on it. They focus in vain on surface-level concerns such as email clients or tech platforms while allowing the real problem, which is cultural, to fester. 

Switching from Slack to Teams or vice versa may streamline processes and access to information, but these are merely tools whose power depends upon the intention and effectiveness of the people using them. Technology platforms can facilitate conversations, but only if people are willing to engage in them. And that’s the issue – without a psychologically safe culture that supports and encourages conversation, there can be no authentic connection with others, no alignment with company mission or vision and no meaningful association with work beyond a paycheck. 

Business is about people. Are your people thriving? 

The return on investment is indisputable; organizations who communicate effectively reap the benefits of higher employee retention rates, trust and productivity. Thus, committing time to culture development doesn’t distract from people’s work; on the contrary, it engages them in it. Again, businesses are made up of people. Businesses serve people. Without understanding people, you can never understand your business or how to make it thrive.

Thriving at work, broadly speaking, is a positive psychological state characterized by a joint sense of vitality and learning.”  Factors contributing to thriving include supportive co-worker behavior, supportive leadership behavior and perceived organizational support. Furthermore, thriving at work produces positive employee outcomes such as decreased burnout, increased commitment and enhanced performance.  

A longitudinal study on adult development conducted by Harvard found that strong relationships are the most important predictor of human happiness. “Loneliness kills. It’s as powerful as smoking or alcoholism,” says Robert Waldinger, author of the study and professor of psychiatry at Harvard Medical School. Thus, particularly in light of the new remote/hybrid work environment, employers should be more concerned with whether employees feel a sense of community rather than whether they’re logging enough hours from home.  

What makes work meaningful? 

Among other things, the Great Reshuffle has taught us people want and expect more from their jobs than just a paycheck. They want their work to matter and they want to feel valued as individuals. They want to feel good about what they do and who they do it with. 

In fact, research by McKinsey reveals employees are much more concerned with relational factors than transactional ones. Employers underestimated how important it is for employees to feel valued by one’s manager, feel a sense of belonging at work, and feel they have caring, trusting teammates. Furthermore, according to a study in MIT Sloan’s Management Review,” meaningful work is self-transcendent and reflective. 

When something is self-transcendent, it is meaningful to other people, animals and non-human nature, not just oneself (i.e. it’s relational). Regarding reflection, John Dewey said it best: “We do not learn from experience…we learn from reflecting on experience.” Educational theorists and researchers have been hammering this home for almost a century. Human beings learn by combining practice and reflection

In another study, researchers found people’s performance was better when they practiced learning-by-doing combined with reflection (vs. learning-by-doing alone). This is because when we reflect on experiences, our perception of our own self-efficacy increases. Some people are reflective by nature, but if employers don’t prompt reflection on topics of relevance to the organization, they miss a critical opportunity to help individuals and the organization grow from their experiences. 

A culture of conversation: The fundamentals 

Drawing on secondary research and nearly seven decades of experience coaching and empowering C-suite leaders, building teams and cultivating relationships to help organizations of all sizes (from nonprofits and small startups to giants like Google) reach their full potential, we’ve identified five fundamentals to developing and sustaining a culture of conversation at work: inclusivity, psychological safety, vulnerability, transparency and reflection.

Inclusivity and psychological safety 

Inclusivity and psychological safety go hand in hand; furthermore, inclusivity is a prerequisite for psychological safety. Amy Edmondson, a professor at Harvard Business School, defines psychological safety as “a climate in which people are comfortable being (and expressing) themselves.” Like too many others, we’ve worked in environments where people are fearful of being punished or perceived as “dumb” for sharing an idea or hypothesis that turns out to be faulty. Moreover, for people from traditionally marginalized groups, the fear of punishment or disapproval in work settings is compounded by the knowledge that, in many regards, they’re still unequal citizens.

A psychologically safe environment encourages people to be themselves and to contribute thoughts and ideas in a democratic way that welcomes diverse perspectives. All ideas are welcome, even though they might not get seized upon. But just because your idea didn’t carry the day today, doesn’t mean it won’t tomorrow, or the day after that. 

Feeling free to share without repercussion hinges upon an inclusive and psychologically safe climate, which is developed, reinforced and sustained through earnest and engaged conversations. Without this, people from diverse backgrounds will go elsewhere and the organization will not reap the benefits of their talents and perspectives. 


Only after a psychologically safe environment is established, can one be expected to embrace their vulnerability. This is, understandably, a big ask. All of us have been hurt or slighted in a social setting, whether on the playground or in the boardroom. As a means of protection, we’ve become guarded and skeptical of people we don’t know. 

For people from traditionally marginalized groups who have had to steel themselves against microaggressions and other forms of exclusion, the prospect of being vulnerable at work can rightly evoke fear and anxiety. Managers and leaders must be sensitive to this fact as they work to develop caring and trusting relationships with their team members. One way to quickly establish trust is for a manager to embrace their own vulnerability. Leaders who are willing to share their vulnerabilities facilitate trust and connection with the people they manage.

No leader is infallible, and it’s important to acknowledge that. Speaking openly about an organization’s good, bad and ugly also presents an opportunity to demonstrate leadership and inspire self-transcendence. When a leader shares a challenge or a setback and engages team members in the process of addressing it (either directly or through authentic conversation), it offers employees the opportunity to engage in meaningful work that transcends oneself. 


A culture of conversation cannot exist without transparency. Too often, we’ve seen executives who feel they must “control the narrative” rather than accepting the truth as the narrative. This misguided strategy creates fear, confusion, resentment and isolation. It promotes uncertainty and a climate of secrecy and mistrust. It also creates zero possibility for alignment around mission, vision, goals and objectives. In short, it’s the sharing not the possession of knowledge that is powerful for an organization’s growth. 

In contrast to secrecy, transparency facilitates trust, problem solving, camaraderie and a connection to something larger than themselves – the organization and its achievements, setbacks and losses. Transparency facilitates alignment on goal setting, problem identification, solution generation, process improvement, external communication, and the list goes on. Without transparency, conversations, when they take place, have no anchor in reality. Energy gets wasted on speculation about topics for which clear answers exist. 


Some people are reflective by nature, but if employers don’t prompt reflection on topics of relevance, they miss a critical opportunity to help individuals and the organization grow. Research shows groups who reflect on their mistakes increase their performance on subsequent assignments by up to 22.8 percent. Furthermore, when they were told that their reflections would be shared with subsequent groups, their performance increased by 25 percent. 

Reflection increases individuals’ confidence and self-efficacy; it therefore increases the confidence and efficacy of the groups to which those individuals belong. The result is a more confident and effective organization that learns from its mistakes and uses them to create growth opportunities for employees. 

In our coaching and training programs at BetterManager, we employ a dance floor and balcony metaphor to drive home the importance of reflection from different vantage points. While a manager is on the dance floor, they are limited to the perspective of what is directly in front of or next to them (i.e. other dancers). However, when they go up to the balcony and look down on the dance floor, they have a fuller, more elevated perspective.

This type of reflection should be ongoing and take place separate from employee evaluations, which often feel obligatory and can take on a disciplinary air. Non-judgmental reflection is about acknowledging and embracing the reality of a situation without chastising oneself or others for their errors. If you’re familiar with mindfulness, this is one of its core tenets. 

The question to ask is not “Hey, what did you do wrong?” but rather, “what actions or behaviors contributed to the success or failure of this project?” Ironically, by depersonalizing errors and mistakes, they become easier to accept and own. 

We’ve included a lot of research in this article, but the inspiration for this piece was our own experience. After decades of coaching executives, developing leaders, training teams and building businesses, we are still surprised by the number of companies who disregard the fundamentals laid out here. Through our work at BetterManager, we know first-hand that today’s workforce expects more from their employers. Those who ignore this reality will end up losing their best talent to organizations with an inclusive and psychologically safe culture of conversation.