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Two Leadership Practices for Fostering Difficult Conversations at Work

Leaders are facing more questions about difficult topics than ever before. Using generative questions and positive framing will help drive conversations that are worth having.

​More and more people across the country have stepped up to participate in democracy. People finding their voice, especially around ethics and moral action, have not stopped at politics. They’ve brought their values and views to work, calling for change and often demanding specific action. What looks like a simple moral decision for an individual, however, can be a significant moral dilemma for an organization. With diverse stakeholders, a leader’s responsibilities span customers, shareholders, employees, a board of directors and vendors. These ethical decisions are often quite complex for leaders who have responsibility for the success of the organization. 

The democratization of business is also being driven by movements such as Purpose-Driven Business, Business as an Agent of World Benefit, Conscious Capitalism and Benefit Corporations. These groups encourage corporations to expand their bottom-line motivations and definition for success, recognizing the full value of all members of the organization and including them in strategic conversations. Research conducted around these movements is encouraging; it shows that engaging the whole system, with its diversity of stakeholders, improves success measures across the board (e.g., 60 percent improvement in performance, 87 percent more likely to remain with the organization,1 1000 percent increase in ROI over a ten-year period2). These companies benefit from the greater loyalty, innovation and performance that results from democratic processes.3 Considering the research in the field of positive psychology and positive sciences,4 it is easy to understand why such efforts drive retention, loyalty and performance. Truly democratic cultures foster employee flourishing: positive emotions, genuine engagement, collaborative relationships, meaningful work and a sense of accomplishment.5 As a result, people are happy in their workplace, they feel valued. People commit to what they help create. 

To maximize that success and manage uncomfortable and potentially volatile conversations requires new leadership skills. To cultivate a democratic workplace, “those in management positions should be proactive in asking employees at all levels about their concerns, questions and thoughts.”6 A core capacity for leaders who hope to navigate the democratization of their organization and the seas of complex change is their ability to foster conversations worth having.

We define conversations worth having as those that are outcomes-focused, appreciative and inquiry-based.7 We introduce two simple practices that leaders can use to engage stakeholders in ways that add value and move forward, even in the most challenging situations. These practices derive from appreciative inquiry (AI), one of the most widely used approaches for fostering positive change at any level in any system. AI is about the search for the best in people, organizations and communities along with the exploration of what might be possible. It’s being used in organizations such as Apple, Coca-Cola, Duke Energy, Green Mountain Coffee Roasters, Johnson & Johnson, VISA Corporation, Vitamix and the United Nations.8 

The complex challenges we face today cannot be resolved by a single or even small group of people. They require leaders who can engage all stakeholders in meaningful and inclusive conversation. Looking for both/and ways of moving forward is not only a source of creativity and innovation, it may well be at the core of any truly democratic process. The two practices that support democratic engagement are generative questions and positive framing. These practices allow people to discover the world beyond dualistic thinking, beyond “your way or mine.” 

Generative Questions

Your capacity to ask generative questions gives you the power to change the way people think (including yourself). These questions make the invisible visible, create shared understanding, generate new knowledge and inspire possibility. Sometimes it is as simple as asking: “How do you see it?” “Can you say more about what you mean?” “What is important to you about this issue?” 

Generative questions are essential when addressing complex issues. For instance, Google made headline news in 2017 firing one of their software engineers for a “document he wrote criticizing the company’s diversity efforts and attributing the tech industry’s gender imbalance to biological differences between men and women.”9 Someone leaked it, and it went viral. The CEO’s response was likely driven by the perceived threat of bad public relations (PR). Let’s take a look at how he might have turned this nightmare into PR magic.

Imagine, instead of firing the author of the document, the CEO initiated conversations across Google focused on developing shared understanding and possibilities for creating a culture that reflects diversity, equity and inclusion (DEI). What if leadership had invited diverse teams—gender, race, ability and even political/religious—to engage in productive and meaningful conversations with an eye toward genuine movement around DEI in the workplace. They might have asked questions such as:

  1. Can you share a workplace experience of discrimination or a lack of DEI? What happened and what was your experience? How might your inclusion have been beneficial for the team and their outcomes?
  2. Now, can you share a peak experience of DEI in the workplace? What happened and what was that like for you? What did you value about yourself and others in that experience? 
  3. According to 2018 report from National Center for Women and Information Technology, women made up only 26 percent of technology-related positions and the headline reads: “there is a lack of diversity in the tech world, and it’s not getting any better.”10 What are your views on why this is the case? How did you come to believe that?
  4. Imagine it’s five years from now, and our organization is making strides towards a culture reflecting shared values around DEI. How are we benefiting from increased DEI? What does that look like? What steps/actions did we take to achieve that? How did we use research and training to support this outcome? What role did you play? 
  5. How might we work together to create a culture of DEI?
    1. What values and behaviors will foster DEI?
    2. If we are making progress on our DEI efforts, in five years how will our culture have changed? What might we do to get started? How will you help make that happen?

Such democratic conversations around complex and volatile situations can strengthen understanding and relationships across divides, allow people to be seen and heard, make visible the diversity of perspectives, create shared values and visions for the future, and identify pathways toward a future that people are ready to make happen. Instead of silencing people and fueling polarized conversations, which landed Google in two lawsuits that are still going on, leaders can choose to foster conversations.

A key leadership behavior is an open and non-judgmental mindset and an attitude of curiosity about how a difficult conversation might link to goals to which the company aspires. This can be challenging if the leader feels threatened. Our reflexive fight-or-flight reaction inhibits access to higher order thinking when we need it most. When dealing with any issue, especially a difficult and complex one, it’s vital for leaders to be deliberate instead of reactive. They need to listen and ask generative questions that make room for conversations that build trust and the kind of openness that has the transformative power to support genuine engagement, even around topics or situations that might have formerly been out of bounds. 

Leaders can use these questions to create space for people to hear and understand one another; to grow and move beyond polarizing and limiting beliefs. In the above example, the imagined conversation was framed around a desired outcome: shared understanding and a movement toward a culture reflecting DEI. This is the second practice: create a positive frame. 

Positive Framing

The second AI practice is positive framing. In its simplest terms, it is talking about what you and others want. This should not be confused with focusing on the positive; the goal of reframing a conversation is to address the problem in ways that move toward desired outcomes. In the above example, the first question focused on the problem itself. Sometimes it’s important to make the invisible visible before you can move forward toward what you want. Understanding other’s perspectives can be a first important step in building bridges across divides and making room for collaboration on a new future.

Race, equity, social injustice, immigration policies, carbon footprint and politics are hot topics in almost every workplace today. Problem-focused conversations fuel polarization. Positive framing focuses those conversations on common, desired outcomes and pathways for achieving those outcomes. In these conversations, people more easily hear one another’s point of view and open their minds and hearts to other perspectives and possibilities. To help leaders create a positive frame, we recommend a technique we call flipping.

Flipping is a three-step process for taking any problem or challenge and creating a positive frame. This approach moves you from a negative, deficit-based frame to a positive frame. The three steps are:

  • Name It: What is the problem, complaint or thing you don’t want?
  • Flip It: What is the positive opposite?
  • Frame It: What is the positive impact if the flip is true? What do you want? What is the desired outcome?

Here’s the flip for the Google example: 

  • Name It: Internal critical and polarizing communication creates a PR nightmare. 
  • Flip It: Internal critical and polarizing communication does not create a PR nightmare. 
  • Frame It: Working together towards shared understanding and a culture reflecting DEI. (And the potential for great PR!) 

While these two leadership practices are simple, they do not come easily for two reasons. The first is cultural. Most leaders have well developed problem-solving skills and have been groomed to have the answers. These are difficult habits to break, requiring a willingness to stay in a place of ambiguity and uncertainty, inviting others in to talk about complex challenges and sensitive issues. The second is physical. As is well-established, humans are neurobiologically wired to scan for threats and react quickly to eliminate them. This fight-or-flight response inhibits our capacity to think clearly. 

If you’re not being physically threatened, we suggest you pause, breathe deeply and get curious. Deep breathing stimulates the parasympathetic nervous system; it is the bridge between reaction and our ability to be deliberate. Curiosity further changes the body chemistry giving you greater access to critical thinking and creativity. Adopting this attitude of curiosity primes you to practice asking generative questions and creating a positive frame for your conversation. 

A global pandemic, massive migration, environmental challenges, and social and political unrest are all but demanding broader engagement and the capacity to have difficult conversations. It is little wonder that organization leaders and managers are feeling the pressure. Any pathway through will involve conversation; it is at the heart of how we interact as social beings. These two practices will allow leaders at all levels to thoughtfully and openly ensure that tough topics are discussed in ways that value everyone’s voice and perspective, create healthy cultures and may also lead to breakthrough solutions.   

Cheri Torres, Ph.D., is Founder and Lead Catalyst at Collaborative by Design. She can be reached at

Jackie Stavros, DM, is Professor at Lawrence Technological University College of Business and IT. She can be reached at
Torres and Stavros are co-authors of Conversations Worth Having: Using Appreciative Inquiry to Fuel Productive and Meaningful Engagement.

1 Simha, B.S. and Vardhan, B.V. (August 2015). Enhancing Performance and Retention through Employee Engagement, International Journal of Scientific and Research Publications, Vol. 5, Issue 8. Available May 9, 2021 at
2 Sisodia, R., Sheth, J., and Wolfe, D.B. (2007). Firms of Endearment. NJ: Prentice Hall. Cameron, K. (2012). Positive Leadership: Strategies for Extraordinary Performance, Oakland, CA: Berrett-Koehler Publishers.
3 The Change Lab 2019 Workplace Survey. The Impact of Organization Change on Employee Wellbeing in American Workplaces by The Change Lab. 
4 Quinn, R. (2015). The Positive Organization: Breaking Free from Conventional Cultures, Constraints, and Beliefs. Oakland, CA: Berrett Koehler Publishers. More research is available at and the mission is to create a better world through the science and practice of thriving organizations.
5 Seligman, M. (2011). Flourish: A Visionary New Understanding of Happiness and Well-being, NYC: Free Press. 
7 Stavros, J., and Torres, C. (2018). Conversations Worth Having: Using Appreciative Inquiry to Fuel Productive and Meaningful Engagement. Oakland, CA: Berrett-Koehler Publishers
8 If you want to learn more about AI, visit the Appreciative Inquiry Commons, a portal providing practice tools and case studies ( ).
9 Redden, M. and Davis, N. (August 2017). Google staffer’s hostility to affirmative action sparks furious backlash. The Guardian. Available 3.12.21 at
10 Sargent, J. (June 5, 2019). There’s a Diversity Problem in the Tech Industry and It’s Not Getting Any Better, Software Development Times,


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