The mindset, roles, and techniques to drive courageous conversations about culture

Successful workplace cultures happen by design, not chance. Intentionally designing your company culture significantly impacts employee engagement, productivity, and the overall success of the organization.

In previous posts I’ve explained the approach, process, and tools to effectively design your culture. Today, I want to address the facilitation aspect: the mindset and roles required to successfully run the culture design process.

Whether you are a team leader, professional facilitator, or team member who wants to facilitate courageous conversations about culture, this post is for you.

Key Phases of Culture Design (and the Mindsets You Need)

The culture design process includes three key phases: Mapping, Assessment, and Design. Here’s a quick recap of the phases and, most importantly, the right mindset for each – to dive deeper into the process, check this post.

1. Culture Mapping:

The purpose of this phase is to understand the current culture of a company or team by integrating multiple perspectives. You want to codify the real culture – how people experience it – and not the official one.

For this phase, the facilitator must adopt the mindset of an anthropologist. Imagine visiting a foreign country – your goal is to understand the unique culture, not to judge it through your preferences or biases.

Facilitating like an anthropologist requires an open mind. Empty your cup and make room for exploration and discovering patterns and behaviors – even if they feel weird, wrong, or unacceptable. Anthropologists aim to understand how people feel, think, and do without judgment.

Culture designers use group conversations, individual interviews, and observation to understand workplace culture. Capture the findings in the Culture Design Canvas without making arrogant, preconceived judgments. It doesn’t matter if what you hear makes sense to you or not, as long as it makes sense to insiders.

2. Culture Assessment:

This phase is about reflecting on the consolidated results and identifying what’s working or not. You want to uncover commonalities, contradictions, and tensions across different teams and levels.

For this purpose, the facilitator must adopt the mindset of a detective. The goal is to uncover what people are not seeing or addressing (purposely or not), challenge assumptions, and connect the dots.  

Thinking like a detective will help you find the culprit – not a person but what in the system needs to be evolved or transformed.

Culture designers provide an outlook on all the building blocks of culture, recommending which needs to be maintained, clarified, improved, or transformed.

Detectives don’t just try to understand what happened but also prevent issues from happening again. When facilitating this phase, specify what you recommend in order to improve the culture.  

3. Culture Design:

Now it’s time to move the conversation into the future. The facilitator should drive discussion about what’s possible without dictating or shaping the outcome. This is challenging because, once again, we need to help the team build the culture it needs/wants, not the one we like.

The purpose of this phase is for the team to co-create that culture. The facilitator adopts the mindset of a sculptor – they help the team visualize their potential and, like marble, remove what’s unnecessary.

Key Roles to Facilitate Culture Transformation

As a culture design facilitator, you must wear different hats – from switching your mindset depending on each phase to playing multiple roles to drive forward conversations and change.

Here are some roles you should be ready to play and how to succeed.

Understand the context and key tensions

Before jumping into the culture mapping sessions, focus on understanding what you’re getting yourself into. Get familiarized with the company, its business model, history, and recent events that impacted its culture.  

Interview key stakeholders from different levels. Aim for diverse voices – old timers can help you understand the evolution, while new employees often observe what most people are missing.

Inspire people to explore what’s possible

In my previous post, I addressed why true neutrality and impartiality are neither possible nor desirable. It can lead to groupthink and mediocrity. Your facilitation superpowers should be an asset, not a liability, if you know how to use them wisely.

As Robyn Eidelson wrote, “How might me being neutral or indecisive actually be hurting the situation?"

Use your ideas, experiences, views, and examples from other companies’ cultures to help people dream of what’s possible. It’s okay to share your thoughts, perspectives, and solutions as long as you are not steering the team.

Codify the real culture

Leaders have a hard time discerning the culture they wish to have from the one they actually have. Your challenge as a culture design facilitator is to codify the real culture – how people experience it, not how leaders talk about it.

For example, when codifying the core values, it is not enough to understand if people can recite them. Probe what those values really mean to them, how they affect behavior, and if they inform decisions. Do the ‘official’ core values have any value?

Uncover gaps across levels or teams

The culture of an organization is the sum of all its subcultures. Effective facilitators understand that culture is not homogenous and welcome differences and unique practices.

Your role as a culture design facilitator is to uncover gaps (across levels, functions, teams, or geographies) while resisting the temptation to eliminate subcultures. Understand which gaps to bridge and which to preserve.

We want everyone to align around the purpose and long-term vision of the culture. However, we should give teams the freedom to experiment with how they want to work. Most importantly, facilitators help spread best practices from specific teams across the organization.

Design the path forward

Good culture facilitators are like a sherpa – they help team members “climb the mountain” without climbing it for them. Sherpas take people to their ‘edge’ without having them fall, as Deborah Rowland wrote. Facilitators climb alongside the team – not from the front or behind.

Sherpas facilitate the process and the journey making it possible for people to reach their destination.

However, defining the mountain to climb is not part of your role. Help team members uncover where they want to go, facilitate the process, and guide them to co-create the journey.

Techniques for Facilitating Courageous Conversations about Culture

Here are a few practical exercises to help you become a more effective culture design facilitator.

1. Demonstrate active listening

Showing participants that their thoughts were heard and understood increases trust and participation. It makes people feel that their voices count – their perspectives are respected and validated.

Try paraphrasing, saying in your own words what a participant said. Summarize an idea if it feels too complicated or the explanation is too long.

Some questions to consider:

“Is this what you mean?”

“Let me see if I can summarize this for everyone…”

“It sounds like you are saying…”

Follow-up questions make people feel heard and help them dive deeper into a topic. Avoid judgmental reactions (“awesome,” “love it,” “that’s a great idea”) to validate people – it might be perceived as favoring certain answers over others.

2. Make it okay to have courageous conversations

Perfectionism often gets in the way of having productive conversations. This is a recurring theme when consulting with various companies. People feel too embarrassed to share their secrets or practices because they compare themselves to idealized versions of other company cultures.

There are many ways to make it safer for people to share what they feel or think without being put on the spot.

I like to set up the room by stating that companies, just like families, are all unique, human, and imperfect – even dysfunctional. Yet, they always find a way to get things done. This gives people reassurance and relief. Removing the need to be perfect makes it easier for them to address issues openly.

The following questions are great to kick-start meaningful dialogue:

Can you define your company in three words?

What’s everyone thinking and no one is saying?

If you were given full authority to do anything you want, what would be the first thing you’d change?

Have people reflect on their own, then debrief in duos or small teams before sharing with the larger team. This promotes psychological safety, making it easier to have courageous conversations.  

3. Legitimize and validate differences

It’s often problematic for people to see past their own views, especially when someone else wants to change their minds. Legitimizing differences breaks this logjam and avoids useless argumentation, as Sam Kaner explains in Facilitator’s Guide to Participatory Decision Making.

It’s easier for a team to understand conflicting views when legitimized by a third party (a facilitator). By recognizing that each party has legitimate views – especially when there’s disagreement – you show respect, dismantling self-defense mechanisms.

Invite people to share their unique views from a point of neutrality. However, validating or accepting different opinions doesn’t mean making them “correct.”

4. Find common ground

Listening for common ground is critical, especially when groups are polarized. Sometimes, teams feel split because they think differently. However, what they focus on drives that divide – some focus on what’s broken, others on what’s working.

Finding common ground builds a sense of hope.

Consider the following steps:

- Capture the differences without attaching them to a person or subgroup

- Identify the commonalities or similarities

- Find common ground focusing on the future: what do we want to build together?

Once people agree on the bigger picture, it’s easier to integrate the different views on how to get there.

5. Listen with a point of view

Effective facilitators are not neutral – they have a point of view. They know how to challenge a team, surface what’s unspoken, or share their ideas to spark conversations.

The challenge lies in sharing your thoughts without driving the conversation.

Try the following steps to listening with a point of view:

👉 Share your opinion - an idea you have, an observation, or an issue that the team is not addressing

👁 Express it as a point of view, not a truth ("Here's an observation I have...")

🤔 Invite the team to reflect on your point of view: What do you think? What am I missing? What about my opinion makes sense and what doesn't?  

🙋‍♀️ Ask people to share their feedback – either using turn-taking or popcorn style

✍ Use paraphrasing and ask follow-up questions without judging (Can you expand on that? What do you mean by...? Tell me more).

💬 Provide feedback and comments based on what participants shared. This might lead to rephrasing, discarding, or evolving your original view.

🙌 If the team agrees to explore your view (assessment, insight, or idea), use questions to evolve the conversation: How can you take my idea to the next level? What do we want to do with the issue I raised? What does this tension say about the team?

6. Address team moods

Dealing with group moods is a key responsibility when you facilitate culture conversations. Negative moods can quickly derail talks, dragging everyone into a downward spiral. Failing to address, call out, or help people manage theirs, can disrupt a culture design session.

Fernando Flores describes the most frequent moods in his book Conversations for Action:

Cynicism: When people have given up on the possibility of change. Cynics are no longer committed to a shared future – they don’t want to improve things but are just hanging on for other reasons.

Victimization: When people blame others or the company for their problems. They bought into the story that they have no real power and believe only leaders can improve things.

Resentment: When people feel that others are not putting in as much effort as they do. They often divide the company into three groups: 1) their team that’s working hard, 2) other teams or “jerks” that cause the problems, and 3) leaders who do nothing about the “jerks.”

Addressing moods in the open will help people become more aware of the roles they play and how they are harming collaboration. These moods will not only hurt your culture workshops but also damage the culture daily.

7. Make space for quiet people

In most meetings, 20% of the participants do 80% of the talking. Making space for quiet voices is vital so you can integrate all perspectives, not just the loud ones.

Silence often indicates that people are holding back, but it's also a reminder that introverts need time – they think before they talk.

Conversational turn-taking ensures everyone has a chance to speak and share ideas. Intentional silence is a good way to make space for those who need time to think. Saying “thank you” after someone shares a thought goes a long way – it sends the message that their opinions matter.

Consider these questions to reflect on your facilitation role:

Have I given equal opportunity for all perspectives to be shared?

What elements of the system (culture) empower certain voices over others?

What can I do to help those voices be heard?

A word of caution: make sure not to disengage extroverts, either. Sometimes, by trying to involve quiet people, facilitators make outgoing folks feel that their opinions don’t count.

Lead the Design Journey, Not the Desired Culture

Your role as a facilitator is to help your client, team, or company design their culture. Like a sherpa, you must walk alongside the team, not take the lead. Participants should define the culture they want – not what you like. Focus on facilitating the conversation, not the outcome.

Our role as facilitators is to serve the greater good (the team or company). We work neither for the leader nor for the people. Taking sides can distort your perspective. Be ready to challenge the leader – even if it’s who pays the bills – as well as team members.  

Lastly, avoid getting caught up with individual behaviors. Culture design is about understanding collective patterns. Focus on the system, not on individual actions.

Article by Gustavo Razzetti, CEO of Fearless Culture

Gustavo facilitates courageous conversations that drive culture transformation. He is a sought-after speaker, culture consultant, and best-selling author of the book Remote, Not Distant.

Razzetti is also the creator of the Culture Design Canvas – a visual and practical method for intentionally designing workplace culture. His insights were featured in Psychology Today, The New York Times, Forbes, and BBC.

‍