Your AI Strategy Isn’t the Problem - Your Readiness Is ft. Elaine Barsoom

Legal AI is having its gold rush moment. But what if you went against the grain and took it slow in order to succeed? In this episode of Between the Briefs, hosts Adrian Cea and Joe Stephens sit down with Elaine Barsoom, AI and innovation leader and Venture Partner at Silicon Foundry, to talk about why AI transformation fails when companies rush into tools before understanding the work. This conversation unpacks why leadership buy-in is only half the equation, why employee fear gets disguised as “we’re too busy” and why the real transformation happens in the quiet rewiring of workflows, decision rights, incentives, governance and human behavior.

Everyone wants an AI strategy but far fewer companies are ready to actually use one.

In this episode of Between the Briefs, hosts Adrian Cea and Joe Stephens welcome Elaine Barsoom, AI and innovation leader and Venture Partner at Silicon Foundry, for a grounded and practical conversation on what it really takes to turn AI ambition into measurable business outcomes.

What You’ll Learn:

Why most AI efforts fail because of readiness, not technology
How to identify where repetitive work, trapped knowledge and overloaded judgment are slowing teams down
Why “go slow to go fast” means doing the work in the right order, not moving timidly
How leadership urgency and employee buy-in have to work together
Why fear often shows up as “we’re too busy” or “the tools aren’t ready”
How legal teams can act as accelerants instead of gatekeepers in AI transformation
Why reskilling is really about rewiring how people work with technology
How proprietary data and tribal knowledge can become a company’s real AI advantage

Tune in to understand what it takes to be truly AI ready.

Highlights:
00:00 Introduction & Meeting Elaine Barsoom

01:04 Elaine’s Background in Innovation, Emerging Tech and Growth

02:06 Building a $200M Joint Venture at American Express

03:13 What It Means to Architect the Execution Layer

04:10 Why Activity Does Not Equal Progress

05:38 How Elaine Bridges Legal, Engineering and Business Teams

07:09 Aligning Incentives Across Engineering, Legal and Leadership

09:02 Why Companies Need Discovery Before Engineers

10:06 Why Legal Engineers Can Be Strategic Accelerants

11:57 The Problem With AI for AI’s Sake

13:27 Balancing Leadership Urgency With Employee Buy-In

15:16 How to Prioritize the Right AI Workflows

17:03 Why Companies Underestimate Fear

19:39 Reskilling, AI Adoption and the Future of Work

22:28 Go Slow to Go Fast

23:21 The Three Questions Every AI Strategy Should Start With

24:45 How Silicon Foundry Supports AI Transformation

26:07 What AI Fear Gets Right and What It Gets Wrong

28:29 Why AI Can Be a Big Advantage for SMBs

30:15 Where to Save Time Without Damaging Trust

31:16 The AI Mandate Problem for Small Businesses

33:12 Elaine’s Favorite Diagnostic Questions

35:42 Build vs. Buy in AI Transformation

40:03 What Elaine Finds Most Exciting in Legal AI

42:07 Why Tribal Knowledge Is the Real Competitive Edge

43:30 Elaine’s Hot Take: It’s a Readiness Problem

44:22 Final Thoughts and Closing Remarks

Quotes:

"Activity doesn’t actually correlate with progress. We have to understand where the underlying work is."
"The leadership can create the urgency, but then it’s really getting the buy-in from the people that are actually doing the work."
"When I say go slow to go fast, I don’t mean moving timidly. I just mean doing the work in the right order."
"People won’t say, I’m afraid that this is going to make me less relevant. They say I’m too busy, or the tools are not ready, or we need more guidance."
"Most companies do not just have an AI technical problem or strategy. They have a readiness problem."