Lindsey Comeau (Reading the Room – CX, Communication, and the Role of Chief of Staff)

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 Learn

• What a Chief of Staff actually does in a growing company
• How customer experience builds deep empathy and people skills
• Why emotional intelligence is core to startup performance
• How to manage up effectively and build executive trust
• The hidden cost of communication breakdowns at work

Perfect For

Startup operators, people leaders, HR and talent teams, and early stage founders trying to build healthier, more human-centered cultures.

Keywords

chief of staff, emotional intelligence, startup culture, conflict resolution, internal operations, people management, startup communication, real leadership, people ops, CX, future of work

Takeaways

• Customer service is an empathy masterclass for future leaders
• The Chief of Staff role flexes based on what the organization needs
• Deep listening includes watching body language, not just hearing words
• Managers must meet people where they are, not manage how they wish to be managed
• Alignment between team members prevents wasted time and turnover
• A lack of communication clarity can derail entire teams
• AI is a great tool, but collaboration and creativity still require human connection
• Vulnerability builds trust and unlocks better conflict navigation

Chapters

00:00 Welcome and Reconnecting

01:16 What Is Sunday and What Does Lindsey Do?

03:01 What It Means to Be a Chief of Staff

06:00 Starting on a Dude Ranch, Finding a Path to Leadership

09:20 Lessons from Leading CX Teams

12:00 Coaching People Through Communication

15:30 How Lindsey Builds Trust Across Teams

19:40 Managing Up and Meeting People Where They Are

23:12 Observing Dynamics in Meetings

26:10 When Communication Breaks Down

29:00 The Hidden Cost of Misalignment

32:00 Using AI Personally and Professionally

35:00 How Sunday Supports AI Adoption Internally

37:20 Building Company Culture Through People Ops

39:40 Final Advice on Navigating Conflict

Related links for this episode:

Lindsey Comeau LinkedIn

Sunday Lawn Care

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