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Communication strategies for remote teams: Devil’s advocate

The workshop:

If you're looking for ways to strengthen your team's dynamics, increase productivity and reduce friction, we invite you to watch this workshop as we continue the conversation around pragmatic communication. By finding an alternative way to the traditional water cooler moments, you'll learn to reject the premise that we have to be in person to have meaningful conversations and impactful progress.

Watch this workshop to learn how to:

  • Be a Devil’s Advocate and speak with candor

  • Continuously and kindly challenge choices

  • Innovate, mitigate risk, and grow your organization

Workshop Host: Gayle Silverman, Principal, Product Delivery Lead at TXI

View the full workshop

The expert:

If you want to build healthier and more inclusive teams, Gayle Silverman will teach you to reimagine adapting to today’s varied work environments. Gayle is a product advocate, delivery leader and meeting coach with over 15+ years of experience in software development, and she is renowned for aligning product teams with TXI's inclusion cards. Gayle collaborates with teams to uncover where opportunity and value intersect and keeps people growing to create something amazing.

Interested in connecting with Gayle? Reach out on LinkedIn

Summary and themes explored in this webinar:


  • The webinar focuses on improving communication within teams and leveraging the roles of Devil's Advocates and Angel's Advocates.

  • The speaker has extensive experience working with software teams and believes that understanding and embracing these roles can lead to clearer and healthier communication.

The Role of Devil's Advocates:

  • Devil's Advocates create space for healthier communication.

  • They ask questions that challenge assumptions and encourage alternate perspectives.

  • Effective Devil's Advocates use questions like "What about...?" and "How will this work in this situation?" to make implicit assumptions explicit.

  • The goal is to promote constructive dissent and strengthen decision-making.

Angels Advocates:

  • Angel's Advocates focus on identifying opportunities and enhancing the quality of decisions.

  • They seek ways to make the best possible decision with available information, rather than aiming for absolute certainty.

The Evolution of Devil's Advocates:

  • In the past, team players were often seen as those who didn't challenge ideas, but now, healthy teams welcome conflicting opinions.

  • Emphasis on public candor and transparent communication, as long as it is done kindly and empathetically.

  • Raising conflicting viewpoints strengthens decision-making by de-risking it.

Overcoming Communication Barriers:

  • 42% of meeting attendees have left without sharing their thoughts, highlighting the need for Devil's Advocates to create a safe space.

  • Reasons for not speaking up include trust-building, power dynamics, fear of job security, and past experiences of being dismissed.

  • The Abilene Paradox, where people hesitate to speak if others don't, further underscores the importance of encouraging open dialogue.

Abilene Paradox and the Importance of Speaking Up:

  • Gayle discusses the Abilene Paradox, a situation where people don't voice their true opinions, even when they believe the decision is wrong.

  • Participants are encouraged to share if they've experienced situations where decisions turned out poorly but were not openly challenged.

Interactive Engagement and Welcoming Alternate Perspectives:

  • The speaker invites questions, observations, and encourages participants to share their perspectives.

  • A participant, Mark, highlights the challenge of power dynamics, especially when disagreeing with more senior team members.

  • Creating a safe environment for Devil's Advocacy is essential, and it's suggested to introduce humor or gamification to make it more approachable.

Business Benefits of Devil's Advocacy:

  • Mention of a study from the Wharton School at the University of Pennsylvania, showing that considering multiple perspectives improves business outcomes.

  • Encouraging multiple opinions stimulates creative problem-solving, fosters innovation, and strengthens decision-making.

Why Devil's Advocates Matter:

  • Devil's Advocates reduce risk, prevent groupthink, surface uncertainties, reframe opportunities, and promote inclusive decision-making.

  • Emphasizes the benefits of having Devil's Advocates in meetings and decision-making processes.

Guiding Principles for Implementing Devil's Advocacy:

  • Acknowledgment of gender, social, and cultural norms that can affect the effectiveness of Devil's Advocates.

  • Emphasizes the need to define a code of conduct for Devil's Advocates, distinguishing between positive and negative attributes.

  • Recommends clear guidelines for when Devil's Advocates should participate and when they should not.

  • Suggests rotating the role of Devil's Advocate to ensure inclusivity and mitigate power dynamics.

  • Encourages explicitly asking for the Devil's Advocate's opinion and highlighting their positive impact on discussions.

Interactive Engagement Continues:

  • Participants share insights on creating a space for counterpoints, promoting debate, and using tools like "fist to five" voting to gauge team alignment.

  • Embracing Individual Responsibility: Individuals should embrace their responsibility in fostering devil's advocacy. This means being willing to challenge one's own opinions and arguments by presenting them along with the opposing perspective. The goal is to ensure that all aspects of a decision are considered thoroughly.

  • Challenging Ideas, Not People: When advocating for an alternative perspective, it's essential to focus on challenging ideas, not attacking individuals. Avoid statements like "You're wrong" and instead use more constructive language, such as, "I feel there may be a gap in this recommendation. Could you help me understand it better?"

  • Embracing Discomfort: Engaging in devil's advocacy may feel uncomfortable, especially for those new to the concept. However, it's important to recognize that discomfort often accompanies growth, and it's okay to experience it during these discussions.

  • Facilitators' Role: Facilitators can play a crucial role in promoting devil's advocacy by intentionally calling on advocates during key moments in a discussion. They can also structure meetings to include specific time for counterpoints and alternative perspectives.

  • Teams with an Advocate Mindset: Teams should collectively support and encourage advocacy. This includes defining how the advocate role works in team agreements, holding each other accountable, and discussing whether specific meetings should have an advocate. Teams can also amplify agreement when advocates bring up new perspectives.

Practical Suggestions for Implementation:

  • Lower the Stakes: Reduce the pressure on individuals by setting random timers and asking prepared questions or introducing a humorous element like a "Best Hard Question Asked" award.

  • Building Advocacy into Conversational Prompts: Use prompts that encourage exploring different viewpoints, such as "What could we be wrong about?" or "What are the unintended consequences?"

  • Leveraging Asynchronous Advocacy: Utilize tools like commenting on documents or adding a dedicated section for devil's advocacy in presentations to gather input asynchronously.

  • Signal Intent for Advocacy: Designate specific time for counterpoints in agendas or use code words or emojis to signal when an advocate should provide an alternative perspective.

Recognizing Red Flags: Be mindful of over-reliance on "Yes, and..." thinking, gendered behavior, and individuals who use phrases like "I think" when playing the advocate role, as these can limit the effectiveness of advocacy.

Practical Examples: The webinar provides practical examples of how to incorporate devil's advocacy into team routines, such as using slack polls, amplifying alternative suggestions, changing the voting process to prioritize the advocate's vote, and conducting future-spectives to anticipate potential issues.

Published by Gayle Silverman in Workshop

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