Letting Go to Scale Up - Joseph Monastiero - Shift & Thrive - Episode # 107
What changes in a leader the moment they stop being the one with all the answers? In this episode of Shift & Thrive, host Natalie Nathanson talks with Joseph Monastiero, CEO of HiQo, just shy of his 90-day mark in the role after rising through sales leadership to chief revenue officer. Joseph opens up about the discomfort of learning to delegate, why he now waits until the end of meetings to speak, and how radical candor and shared vulnerability have shaped his leadership style since his early days working alongside his father. The conversation also digs into how AI is reshaping go-to-market strategy and buyer behavior, why he sees AI as a force multiplier rather than a shortcut, and his advice for CEOs who want an honest read on what's really happening inside their sales organization.
Takeaways:
- Delegation gets harder as authority grows. Trust your team to execute rather than instinctively jumping in first.
- Speak last in meetings. Listening before opining prevents rash decisions and surfaces better options.
- Share your weaknesses openly with your team. It builds trust and models the vulnerability you want back from them.
- Match go-to-market leadership style to company stage. Some moments call for adaptability, others for steady consistency.
- Arm your go-to-market leaders with domain expertise, then let them own execution and pipeline decisions.
- Get on the ground with your sales team regularly. It's the fastest way to see what board decks and status updates smooth over.
- Use AI as a force multiplier for research and speed, not a replacement for judgment and strategic rigor.
Quote of the Show:
- "Radical candor, before it was a thing, was one of my principles. It's that true transparency and ability to be candid with your team and those that are either on your level, above, or below. You're allowed to argue, have a disagreement, have a discussion, and leave that conversation potentially frustrated or angry, but knowing that the compromise made, the shift made, or the agreement that you came to was really the best there." - Joseph Monastiero
Links:
Ways to Tune In:
- Spotify: https://open.spotify.com/show/2D1YbT2QhKxIwbREpU7EMb
- Apple Podcasts: https://podcasts.apple.com/us/podcast/shift-thrive-ceo-insights-on-driving-change/id1740828813
- Amazon Music: https://music.amazon.com/podcasts/fa60b654-1955-4055-93df-fdd40c2a5c8f/shift-thrive-ceo-insights-on-driving-change
- iHeart Radio: https://www.iheart.com/podcast/269-shift-thrive-ceo-insights-166792501
- Pandora: https://www.pandora.com/podcast/shift-and-thrive-ceo-insights-on-driving-change/PC:1001086797
- YouTube: https://www.youtube.com/channel/UClf9QxGUxZw_Sv8_4bZP34Q
This show is sponsored by Magnetude Consulting, bringing you the thinking-Power of a Growth Consultancy and the Getting-It-Done Power of a full-service B2B Marketing Agency.
Learn more at: https://www.magnetudeconsulting.com
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