On this episode of Future Works, Gillian sits down with Lindsey Comeau, Chief of Staff at Sunday and one of the best listeners in the business. With a non-linear path from dude ranch to startup operations, Lindsey has worked across customer experience, marketing, and executive leadership. Today, she acts as the connective tissue inside a fast-moving company, helping people show up, communicate, and solve conflict more effectively. Together they explore what the Chief of Staff role really is, how startups can better invest in internal clarity, and why learning to listen might be the best leadership skill of all.You’ll LearnWhat a Chief of Staff actually does in a growing companyHow customer experience builds deep empathy and people skillsWhy emotional intelligence is core to startup performanceHow to manage up effectively and build executive trustThe hidden cost of communication breakdowns at workPerfect ForStartup operators, people leaders, HR and talent teams, and early stage founders trying to build healthier, more human-centered cultures.Keywordschief of staff, emotional intelligence, startup culture, conflict resolution, internal operations, people management, startup communication, real leadership, people ops, CX, future of workTakeawaysCustomer service is an empathy masterclass for future leadersThe Chief of Staff role flexes based on what the organization needsDeep listening includes watching body language, not just hearing wordsManagers must meet people where they are, not manage how they wish to be managedAlignment between team members prevents wasted time and turnoverA lack of communication clarity can derail entire teamsAI is a great tool, but collaboration and creativity still require human connectionVulnerability builds trust and unlocks better conflict navigationChapters00:00 Welcome and Reconnecting01:16 What Is Sunday and What Does Lindsey Do?03:01 What It Means to Be a Chief of Staff06:00 Starting on a Dude Ranch, Finding a Path to Leadership09:20 Lessons from Leading CX Teams12:00 Coaching People Through Communication15:30 How Lindsey Builds Trust Across Teams19:40 Managing Up and Meeting People Where They Are23:12 Observing Dynamics in Meetings26:10 When Communication Breaks Down29:00 The Hidden Cost of Misalignment32:00 Using AI Personally and Professionally35:00 How Sunday Supports AI Adoption Internally37:20 Building Company Culture Through People Ops39:40 Final Advice on Navigating ConflictRelated links for this episode:Lindsey Comeau LinkedInSunday Lawn CareIf you enjoyed this conversation, hit subscribe and follow along as we explore more ideas shaping the future of work.© 2025 Future Works Podcast / AspectLearn more about Aspect at - https://www.aspect.com/ Brought to you by Aspect and Alvaria https://www.aspect.com/ https://www.alvaria.com/ © 2025 Aspect and Alvaria

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