Stop, Drop & R.O.L.E.

Outgrowing Technology – Time to Upgrade or Stay the Course?


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Technology evolves at lightning speed, leaving many organizations struggling to keep up.

In this episode of Stop. Drop. & R.O.L.E., Jen dives into the challenges mid-level managers and executives face when deciding whether to upgrade outdated systems or stick with what they know.

Using the R.O.L.E. method, she’ll explore:

  • How to communicate proactively and determine who to invite to the table when exploring current and new technology.
  • The signs your tools are holding you back (hint: endless workarounds are a red flag).
  • Why 70% of digital transformations fail—and how YOU can avoid becoming part of that statistic.
  • The secret to successful adoption: involving the right people every step of the way.
  • How to make the best decisions when the sales people are promising you diamonds, so you don't end up with dust
  • Strategies for learning and keeping up with innovations like AI and AR in your industry.
  • Tips to use with tech salespeople to make sure you don't sign the contract and have to recover from buyers remorse for years to come

Jen shares relatable stories, eye-opening statistics, and practical advice for evaluating technology investments without losing sight of your people.

Listen to better navigate the murky waters of tech upgrades, ensuring your decisions align with business goals and drive engagement from leadership to your customers.

© 2025 Perpetual Capacity Coaching & Consulting, LLC. The Stop. Drop. & R.O.L.E.™ and The Great Outgrown™ frameworks are original, proprietary works created by Perpetual Capacity Coaching & Consulting, LLC. All concepts, names, processes, and stories shared in this episode are protected by copyright. Reuse, reproduction, or republishing of this content — in part or whole — requires prior written permission.

This episode contains early ideas and concepts that are being expanded and refined in The Great Outgrown™. All rights reserved.

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Stop, Drop & R.O.L.E.By Jen Cáceres