Saying Yes Too Much Hurts Results w/ Lindsey LeFaivre VP of Customer Success at AchieveIt episode artwork

EPISODE · Jan 26, 2026 · 37 MIN

Saying Yes Too Much Hurts Results w/ Lindsey LeFaivre VP of Customer Success at AchieveIt

from The Customer UnSuccess Podcast · host Joe Di Grande

We unpack how saying yes too fast derails outcomes and how visible boundaries make better teams. Lindsey LeFaivre shares hard-won lessons from a 1,500-branching workflow misfire to a delivery-room out-of-office, turning mistakes into practical leadership habits.• discovery before commitment on complex requests• validation of true customer needs and success metrics• small-team pressure, imposter syndrome, overwork triggers• rituals for boundaries and recovery during remote work• non negotiables on the calendar and offline windows• resource requests as a leadership signal not a weakness• meeting hygiene, playbooks and focus-time protection• interviewing for culture and real work-life balance• community learning and strategic customer success mindsetIf you got some value from this conversation, hit subscribe, leave a rating or review, and share it with someone who's also out there trying to build a better customer success or go-to-market strategy, even if it's messy along the way.For more frameworks, tools, automated playbooks, check out JoeDoesTechTouch.com and subscribe to our newsletter.🎙️ Guest: Lindsey LeFaivreVice President of Customer Success at AchieveIt📣 Find Lindsey:LinkedIn: https://www.linkedin.com/in/lindseyingalls/ 🔥 Topics Covered:🟣 Why early-career CS professionals struggle to say “no” — and how that leads to burnout🟣 A real startup story of working 24 straight hours on a customer request that never shipped🟣 How imposter syndrome drives unhealthy work habits in Customer Success🟣 The hidden cost of always saying “yes” to customers instead of asking better questions🟣 Why work-life balance isn’t 50/50 — it comes in seasons and tradeoffs🟣 Lessons learned from working through maternity leave during COVID🟣 Why asking for help is a leadership skill — not a weakness🟣 The importance of setting and communicating non-negotiables (like school pickup time)🟣 How leaders must model healthy boundaries to give teams permission to do the same🟣 Why results matter more than hours logged — especially in remote CS teams🟣 How to evaluate company culture by asking leaders what their work-life balance looks like🟣 Why Customer Success culture thrives on generosity, transparency, and shared learning📚 Resources Mentioned:🟣 The Strategic Customer Success Manager — Lindsey’s top recommendation and team-wide read - https://www.amazon.com/Strategic-Customer-Success-Manager-Blueprint/🟣 Atlanta Customer Success Community — https://www.atlcs.community/🌐 Website https://www.joedoestechtouch.com/📰 Subscribe to the JDTT Newsletter –  Get raw insights, no-fluff frameworks, and tech touch tactics straight to your inbox: https://www.joedoestechtouch.com/jdttnewsletter 🎙️ Be a Guest on the Podcast Have a CS horror story or digital-first strategy worth sharing? Submit to be a guest:https://www.joedoestechtouch.com/podcast 🔗 Connect with Joe on LinkedIn https://www.linkedin.com/in/josephdigrande📺 Watch Full Episodes on YouTube: https://www.youtube.com/channel/UCaH58ojbaWym4ej_PedQ4Fw_______________________________Tools:Logitech Creators Blue Yeti USB Microphone: https://amzn.to/4nHOFDNLogitech Brio 4K Webcam: https://amzn.to/3GtKsmxSony WH-1000XM4 Noise Cancelling Wireless Headphones: https://amzn.to/44Q0xv4Apple 2024 MacBook Pro Laptop: https://amzn.to/4lH6u3W

Episode metadata supplied by the publisher feed · Published Jan 26, 2026

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We unpack how saying yes too fast derails outcomes and how visible boundaries make better teams. Lindsey LeFaivre shares hard-won lessons from a 1,500-branching workflow misfire to a delivery-room out-of-office, turning mistakes into practical leadership habits. • discovery before commitment on complex requests • validation of true customer needs and success metrics • small-team pressure, imposter syndrome, overwork triggers • rituals for boundaries and recovery during remote work • non nego...

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Saying Yes Too Much Hurts Results w/ Lindsey LeFaivre VP of Customer Success at AchieveIt

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