Start with the Problem, Not the Program: Rethinking L&D Strategy with Caroline Freeman episode artwork

EPISODE · Mar 3, 2026 · 37 MIN

Start with the Problem, Not the Program: Rethinking L&D Strategy with Caroline Freeman

from The Assembly · host Assemble You

In this insightful interview, Brigid sits down with Caroline Freeman of Grey Space Consulting.Caroline is a leadership and learning consultant and the founder of Grey Space Consulting. Her career began at Nordstrom in 2008 , where she learned the value of promoting from within and prioritizing people development. Today, she focuses on bridging the gap between ambition and reality , helping organisations move beyond simple "we need training" requests to instead diagnose real capability gaps and misaligned systems.In this episode, Caroline discusses how L&D professionals can adopt a commercial mindset to better align with business objectives , including:L&D as the Glue: Caroline describes L&D as the essential "glue" that connects an organisation's commercial strategy with its people strategy. Start with the Problem, Not the Program: Caroline emphasises working backward from the desired business outcome rather than simply taking orders for a new training course. She advocates for acting as a diagnostician to find the root of the problem.Transparency and Trust: Caroline advises on how to handle situations where business goals, like reducing headcount, conflict with L&D goals, like employee retention. She advocates for transparency with leadership and teams to build trust and ensure everyone understands the true mission.Thinking Outside the Box: L&D solutions do not always require a two-hour workshop with a slide deck. Caroline shares how unconventional approaches, like a simple 25-minute chat or a quarterly morning recognition meeting for support staff, can drive engagement and solve systemic issues . She also suggests pulling established tools like a nine-box grid out of the archives to quickly identify and develop high-potential employees.Flipping the Script on Delivery: Caroline discusses the power of shifting from a traditional subject matter expert model to facilitating peer-to-peer learning. She encourages bringing learners into the process and giving them a seat at the table to help design solutions.Caroline offers a highly practical perspective on elevating the L&D function. If you want to learn how to secure a seat at the table and prove the commercial value of your training initiatives, this is a must-listen-to episode.Connect with Caroline on LinkedIn: Caroline Alderman (Freeman) Looking for a content library to help your team develop their productivity, communication, leadership skills and more? Check out assembleyou.com and follow us on LinkedIn.

In this insightful interview, Brigid sits down with Caroline Freeman of Grey Space Consulting.Caroline is a leadership and learning consultant and the founder of Grey Space Consulting. Her career began at Nordstrom in 2008 , where she learned the value of promoting from within and prioritizing people development. Today, she focuses on bridging the gap between ambition and reality , helping organisations move beyond simple "we need training" requests to instead diagnose real capability gaps and misaligned systems.In this episode, Caroline discusses how L&D professionals can adopt a commercial mindset to better align with business objectives , including:L&D as the Glue: Caroline describes L&D as the essential "glue" that connects an organisation's commercial strategy with its people strategy. Start with the Problem, Not the Program: Caroline emphasises working backward from the desired business outcome rather than simply taking orders for a new training course. She advocates for acting as a diagnostician to find the root of the problem.Transparency and Trust: Caroline advises on how to handle situations where business goals, like reducing headcount, conflict with L&D goals, like employee retention. She advocates for transparency with leadership and teams to build trust and ensure everyone understands the true mission.Thinking Outside the Box: L&D solutions do not always require a two-hour workshop with a slide deck. Caroline shares how unconventional approaches, like a simple 25-minute chat or a quarterly morning recognition meeting for support staff, can drive engagement and solve systemic issues . She also suggests pulling established tools like a nine-box grid out of the archives to quickly identify and develop high-potential employees.Flipping the Script on Delivery: Caroline discusses the power of shifting from a traditional subject matter expert model to facilitating peer-to-peer learning. She encourages bringing learners into the process and giving them a seat at the table to help design solutions.Caroline offers a highly practical perspective on elevating the L&D function. If you want to learn how to secure a seat at the table and prove the commercial value of your training initiatives, this is a must-listen-to episode.Connect with Caroline on LinkedIn: Caroline Alderman (Freeman) Looking for a content library to help your team develop their productivity, communication, leadership skills and more? Check out assembleyou.com and follow us on LinkedIn.

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Start with the Problem, Not the Program: Rethinking L&D Strategy with Caroline Freeman

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This episode was published on March 3, 2026.

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In this insightful interview, Brigid sits down with Caroline Freeman of Grey Space Consulting.Caroline is a leadership and learning consultant and the founder of Grey Space Consulting. Her career began at Nordstrom in 2008 , where she learned the...

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