#0172: (CT) ILTA Just-In-Time: Incorporating Copilot in a Late Follower Law Firm

ILTA Voices27mApril 7, 2026

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AI-Generated Summary

In this first episode of a three-part 'Just in Time' series from ILTA Voices, host Aaron Barby and guest Jonathan Woolley, Senior AI Solutions Architect at Hush Blackwell, challenge the common perception that being a 'late follower' in adopting Microsoft Copilot is a disadvantage. Instead, they argue that a strategic delay allows law firms to learn from early adopters’ mistakes, refine governance, and avoid the rapid, disruptive changes that come with being first. Drawing on their experience with Copilot’s evolution since its pre-release pilot, they emphasize the importance of thoughtful rollout planning, including selecting diverse champions, setting clear expectations, and managing the 'human in the loop' reality of AI hallucinations. The discussion highlights how poor data hygiene—like misconfigured SharePoint sites—can be exposed by Copilot, making pre-implementation data audits critical. They also stress the need for cross-functional governance councils that include attorneys, IT, and business professionals to ensure balanced, effective adoption. The episode concludes with a preview of the next installment, which will dive into technical infrastructure like Microsoft Graph and data security controls. Key takeaways include: 1) Being a late follower can be a strategic advantage by allowing firms to learn from others’ mistakes and avoid early instability; 2) Success hinges on selecting diverse, thoughtful champions and setting clear expectations around AI’s limitations; 3) Governance must be proactive—especially around data access and sharing—before licensing is rolled out; 4) Training should focus on 'why' and 'how' rather than just 'what'; 5) A cross-functional AI committee is essential for alignment and faster decision-making; 6) AI adoption is a shared learning journey, not a one-time deployment; 7) Avoid the 'squeaky wheel' trap by not assigning licenses to only the most vocal users; 8) Celebrate and share early wins to build momentum and trust.

Key Takeaways
1

Being a late follower in AI adoption can be a strategic advantage by allowing firms to learn from early adopters’ mistakes and avoid rapid, disruptive changes.

2

Success with Copilot depends on selecting diverse, thoughtful champions and setting clear expectations about AI’s limitations and the need for human oversight.

3

Governance must be proactive—especially around data access and sharing—before licensing is rolled out to prevent exposure of misconfigured systems.

4

Training should emphasize the 'why' behind AI adoption, not just the 'how,' to build buy-in and reduce resistance.

5

A cross-functional AI committee including attorneys, IT, and business professionals is critical for balanced, effective rollout and faster decision-making.

…and 3 more takeaways available in PodZeus

Chapters
0:00
5 min

Why Being a Late Follower Can Be a Strategic Advantage

Being late doesn't necessarily mean you're behind. It just means that you're being conscious and you're being strategic and you want to see if this product is going to stick around.

Highlight
5:00
5 min

The Risks of Rushing: Governance, Data Hygiene, and Early Adoption Pains

Copilot tends to surface sharing issues that already exist... It was the underlying group structure, right? That SharePoint piece or that SharePoint site that was not set correctly.

Highlight
10:00
5 min

Building a Successful Rollout: Champions, Context, and Expectation Setting

Setting the expectations up front. They need to know that it's going to hallucinate. They need to know to use the phrase that everybody uses. There has to be a human in the loop.

Highlight
15:00
5 min

The Role of Training and the 'Human in the Loop' Mindset

The conversation explores how attorneys may feel intimidated by AI, likening it to the early days of Microsoft Word. The need for safe, non-judgmental training environments is stressed, along with the importance of guiding users from basic prompts to advanced use.

20:00
5 min

Creating a Cross-Functional AI Committee for Sustainable Adoption

Barby and Woolley discuss the value of a balanced AI committee that includes attorneys, IT, and business professionals. This ensures diverse perspectives, faster decision-making, and the ability to turn early adopters into internal champions.

High-Impact Quotes
Copilot tends to surface sharing issues that already exist... It was the underlying group structure, right? That SharePoint piece or that SharePoint site that was not set correctly.
Jonathan Woolley20:19
Viral: 90.0
Setting the expectations up front. They need to know that it's going to hallucinate. They need to know to use the phrase that everybody uses. There has to be a human in the loop.
Jonathan Woolley12:57
Viral: 88.0
Being late doesn't necessarily mean you're behind. It just means that you're being conscious and you're being strategic and you want to see if this product is going to stick around.
Jonathan Woolley2:48
Viral: 85.0
Speakers

Host

Aaron Barby

Guest

Jonathan Woolley
Topics Discussed
AI Adoption Strategy95%Microsoft Copilot Implementation90%Law Firm Governance88%Data Security and Privacy85%Change Management82%AI Training and Onboarding80%Cross-Functional Collaboration78%AI Hallucinations and Limitations75%
People & Brands

Microsoft Copilot

product

25xPositive

Jonathan Woolley

person

20xPositive

Aaron Barby

person

15xNeutral

SharePoint

product

7xNeutral

Hush Blackwell

organization

5xPositive

Thompson Coburn

organization

4xNeutral

Teams

product

3xNeutral

ILTA Voices

media

3xPositive

Microsoft Graph

product

2xNeutral

Artificial Intelligence Committee

organization

2xPositive

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