What Breaks Next
Shawna Curran
Fractional COO for growing tech teams
Hand off the work that keeps landing on you, and keep it handed off
Your team has grown, and the work still finds its way back to you. Decisions wait on your sign-off. Tasks you handed off return a few weeks later. New tools arrive; someone has to keep them running, and that lands on you too.
Work that keeps coming back to you has two locks, one in your people and one in your systems. Most fixes turn only one key, so the work circles back. The people key develops your strongest people into real owners of decisions and recurring work. The systems key connects your tools and puts automation and AI where they fit, so your people spend their time on the work only they can do.
I learned this while scaling a B2B SaaS team by about 300%, starting with the people doing the work and building the process with them. In this workshop, you’ll bring one piece of work that keeps landing on you. We’ll trace where it breaks next, fix the nearest break on both keys, and turn it into a 30-day plan you can start the following week.
By the end, you’ll have one recurring problem resolved, a named owner for every piece of it, and a clear plan for what to fix next.
What you’ll learn
Go from being where every decision and recurring task lands to leading a team that owns them, with tools and AI working for your people.
Start with the friction your team has stopped noticing, and trace it to the decision, handoff, or tool gap that keeps producing it.
Run it forward to name what breaks, for whom, and roughly when, using a guided worksheet on your own real problem.
Choose the nearest, costliest break to fix first, with live feedback on your read.
Place your top two or three people on the Capacity Grid by how much their judgment is trusted and how often they step forward.
Spot who’s ready now, who needs development first, and who’s carrying more than they’re recognized or paid for.
Sort the decisions still routing through you with the Decision Ownership Map: keep for now, move with a window, move, or yours.
Set an owner for each, what they can decide on their own, and the one trigger that brings it back to you.
Practice the handoff conversation, ideally with your own top people in the room.
Run your recurring work through the Boomerang Sort to see what to connect, automate, hand off, drop, or keep.
Watch a live build in Zapier and Claude, from a request landing to a response playbook drafted from your team’s know-how.
Name the person who owns every automated piece, so it doesn’t come back to you the first time it breaks.
Map the first fix, the change that keeps it from returning, and the first step written out for every task.
Leave with all three tools filled in for your own team, ready to run again on the next problem.
Workshop agenda
Welcome, then find the break and run it forward
Bring one piece of work that keeps landing on you. Trace it to the gap that keeps producing it, name what breaks and roughly when, and get live feedback on your read.
Read your people on the Capacity Grid
Place your top two or three people by trust and initiative. Then sort out who’s ready to own more now, who needs development first, and who’s carrying more than anyone has noticed.
Hand off decisions that hold
Sort your decisions with the Decision Ownership Map and give each one an owner, a guardrail, and the trigger that brings it back to you. Then practice the handoff conversation in breakout rooms.
Connect and automate, with a person owning every piece
Run your recurring work through the Boomerang Sort, then watch a live build in Zapier and Claude. See how tools give your people time back, and who catches it when something breaks.
Build your 30-day plan
Turn the day into a plan: the first fix, the change that keeps it from coming back, and the first step written out for every task. Close with share-outs and open questions.
Learn directly from Shawna
Shawna Curran
Fractional COO | Scaled a B2B SaaS team ~300%
Who this workshop is for
Managers and directors at growing tech companies whose teams have grown while decisions and recurring work still route through them
Leaders who’ve handed work off before and watched it come back
Leaders who want to use AI and automation in a way that keeps their people at the ce
What's included
Lifetime access
Go back to course content and recordings whenever you need to.
Community of peers
Stay accountable and share insights with like-minded professionals.
Certificate of completion
Share your new skills with your employer or on LinkedIn.
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