Transitioning Customer Success from Reactive Support to Proactive Growth
Designed for Customer Success Managers (CSMs) in mid-market SaaS companies who have relied primarily on ticket-based support and are now tasked with driving product adoption, renewals, and expansion. to spark real collaboration and high-energy learning.
A 90-minute interactive virtual workshop scheduled two weeks after a major SaaS platform release. CSMs are overwhelmed with support tickets and feel stuck in a 'firefighting' mode, while leadership is pressuring teams to demonstrate measurable impact on retention and upsells. Participants are skeptical about finding time for proactive work when reactive tasks dominate their calendars.
Before the Ticket Drops
Kick off with a poll featuring surprising ‘predictable churn moments’ (e.g., when users pause logins, ignore new features, or submit ‘how do I’ tickets). Show anonymized usage data spikes before churn to spark curiosity. Participants guess which signals predict trouble.
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Why this works
Provokes curiosity by showing the invisible patterns behind customer loss, encouraging a mindset shift from reacting to predicting.
The ‘Support Hero’ Trap
Present three common beliefs as 'myth or fact': (1) Fastest ticket solver wins loyalty, (2) Proactive outreach annoys customers, (3) Most expansion comes from technical issue resolution. Ask for a quick thumbs-up or thumbs-down, then share industry data that flips expectations.
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Why this works
Surface and bust misconceptions to clear the ground for new habits.
Silent Signals Chatstorm
Guide a low-pressure chatstorm: 'Name one customer behavior you’ve seen that felt like “something’s wrong” but didn’t result in a support ticket.' Collect answers rapidly in chat and highlight patterns.
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Why this works
Normalizes silent warning signs and shows participants they already have instincts worth trusting.
Customer Success Shark Tank
Divide into breakout groups. Each group pitches a 2-minute proactive initiative (e.g., automated check-ins for low adopters, milestone celebrations) to a 'shark panel' made up of peers, who invest imaginary dollars based on potential to prevent churn or drive upsell.
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Why this works
Injects energy, creativity, and a friendly competitive edge, pushing participants to think bigger than just support.
The $10k Plateau Dilemma
Share a real composite scenario: 'Your customer has plateaued at $10k ARR for 18 months. They never escalate issues or ask for help, but they also never expand. Leadership wants growth. What do you do — and what risks do you see?' Explore responses in pairs.
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Why this works
Grounds proactive moves in tangible stakes and dilemmas CSMs face daily.
Proactive Commitment Postcards
Close with a personal reflection: Each CSM writes a ‘postcard to future me’ (in chat or physical card): 'This month, I’ll shift one hour from tickets to proactive outreach by…' and shares their specific action. Optionally, they email this to themselves or a partner.
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Why this works
Secures commitment through personalized goal-setting and peer accountability, solidifying workshop gains.
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