C5 Insight

06/02/2026

AI is raising expectations for how quickly organizations can respond, decide, and adapt.

But speed alone won't make a company better.

Leaders need to create the clarity that helps teams understand what matters, where to focus, and how work should evolve as new capabilities become available.

That doesn't require perfect foresight. Leadership in the age of AI requires a willingness to rethink how the organization operates and adapt as conditions change.

The leaders who do this well won't just ask, "Where can we use AI?"

They'll ask, "How should our work change now that AI is part of it?"

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This blog series was developed from a Fireside Chat at the 365 Leadership Summit (2025) with Geoff Ables, CEO of C5 Insight, and John Siefert, CEO of Cloud Wars and Dynamic Communities. The conversation explored what leaders are experiencing as AI reshapes how work gets done and what that means for leadership itself.

Read the full blog: https://c5insight.com/ai-leadership-changing-expectations/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=C5%20Insight
Learn more about 365 Leadership Summit: https://c5insight.com/365-leadership-summit/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=C5%20Insight

06/01/2026

One of the most important findings from Microsoft's 2026 Work Trend Index is the Transformation Paradox:

Employees are ready for AI.
Most organizations aren't.

Leaders are asking teams to rethink how work gets done, while still measuring them on how it's always been done.

So, people hesitate:
Do I optimize the current process...or redesign the work with AI (without recognition)?

That hesitation is created at the top.

Until leadership resets how work is measured and rewarded, AI won't transform much.

Transformation doesn't start with tools; it starts with what leaders choose to change.

05/29/2026

AI pilots aren't a test that you either pass or fail.
That framing is part of the problem.

A pilot isn't a finish line. It's a starting point.

The real work, building governance, scaling what works, measuring actual business outcomes, begins after the pilot ends.

The organizations seeing meaningful results from Microsoft Copilot and enterprise AI are the ones who had a clear path for what comes next.

That's what we're covering in our upcoming webinar:
The AI Transformation Playbook: A Proven Path from AI Pilot to Business Value.

If your organization has taken an early step into AI but isn't sure how to build on it, this session was designed for that conversation.

Register here: https://c5insight.com/webinar-ai-transformation-playbook/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=C5%20Insight

05/29/2026

Your employees aren't waiting for an official AI strategy.

Business Insider recently covered the rise of employees using unapproved AI tools at work , often because they're trying to move faster while their organizations are still debating policies, approvals, and AI tools.

And honestly, it's not hard to understand why.

When employees experience AI compressing hours of work into minutes, they're not going to wait patiently for a six-month governance committee to catch up.

But that delay creates real risk:

- Sensitive data being entered into unapproved tools
- AI-generated work being treated as fact without review
- Teams creating duplicate or conflicting processes
- Leaders losing visibility into where AI is influencing decisions
- Innovation happening outside the systems meant to protect the business

The answer isn't all or nothing.
It's not "no AI" or "AI without governance."

Start with a safer path forward:

- Give employees approved AI tools with enterprise-grade security, like Copilot Chat.
- Get training from Copilot Specialists like C5 Insight to reinforce responsible use.
- Establish a Center of Excellence to guide AI adoption, governance, and continuous improvement.
- Measure what's being used, what's working, and where governance gaps remain.
- Continue piloting AI solutions, refining governance, and scaling what delivers measurable business value.

Read the full article: https://www.businessinsider.com/sneaky-rise-shadow-ai-workplace-claude-it-2026-5?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=C5%20Insight

Shh, don't tell IT I'm using Claude!

05/28/2026

In our latest webinar, we share real-world data C5 Insight collected from 180+ Copilot users in nine organizations to answer a common question:

What is Copilot's ROI?

Here's what the data shows:

• The average user is reclaiming ~45 minutes per week (and that's just in the early stages)
• Meeting summaries are the #1 use case with document creation as a close second
• 85% of users report improved quality of work, not just speed
• 64% say Copilot enables them to do work they couldn't do before

One key takeaway:
Employees are ready for AI. Organizations aren't. (Microsoft 2026 Work Trend Index Annual Report)

Organizational factors (e.g., manager support) drive 2x more impact than individual mindset alone. Is your organization embracing the AI era?

If you're developing your AI strategy or building the business case, this webinar gives you a data-backed path forward.

Watch the webinar on YouTube: https://youtu.be/d2Kmpr-0gSI?si=KkFPRI5K21hskEkm&utm_campaign=coschedule&utm_source=facebook_page&utm_medium=C5%20Insight

05/27/2026

Agentic AI is often described as "more advanced automation."

But that framing undersells what's actually changing.

Traditional automation executes steps.
Agentic AI coordinates work.

And coordination requires context, ownership, decision clarity, and reliable data.

That means success is less about how capable the agent is and more about how well the work itself has been designed.

When processes are clear, agentic AI becomes a coordinator.
When they aren't, it becomes a spotlight.

When AI enters the workflow, it doesn't just speed things up. It reveals where work breaks down:

Messy handoffs.
Unclear accountability.
Outdated rules.
Duplicate data.
Process gaps that were already there.

That's why agentic AI automation shouldn't start with the agent.
It should start with the process.

Before you bring AI agents into the workflow, have you pressure-tested the process they're supposed to support?

05/26/2026

Most organizations have taken an early step into AI.

But launching a pilot and turning AI into measurable business value are two very different things.

In fact, 95% of AI initiatives fail to move past the pilot stage (MIT).

On June 3 at 2 PM Eastern, C5 Insight's Geoff Ables and Traci Winter will walk through our AI Transformation Playbook, a practical framework for moving from experimentation to enterprise impact with Microsoft Copilot and agentic AI.

We'll cover how to:

• Launch focused AI pilots designed to prove ROI
• Evaluate what worked, what didn't, and what deserves to scale
• Avoid common failure patterns in early AI initiatives
• Build a repeatable path to measurable business outcomes

If your organization is planning an AI pilot, expanding Microsoft 365 Copilot adoption, or trying to figure out what comes next, this webinar will give you a clear path forward.

Register here: https://c5insight.com/webinar-ai-transformation-playbook/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=C5%20Insight

*All registrants will also receive a copy of C5 Insight's AI Transformation Playbook*

05/25/2026

Today, we pause to honor those who gave their lives in service to our country.

Memorial Day is a reminder that the freedoms we often move through so quickly were protected at the highest cost.

Today, we remember.

05/22/2026

The new AI agents in Dynamics 365 Sales are powerful.

They can also create unexpected disruption if your sales team doesn't understand what they actually do once enabled.

For example, the Dynamics 365 Sales Qualification Agent doesn't just sit quietly in the background until prompted.

It can autonomously reassign leads to itself, research them, engage them, disqualify them, and route them back to sellers.

That may sound efficient until...

- Active leads start disappearing from reps' views
- Nurture paths get disrupted
- Qualified leads get reassigned without the relationship context your team depends on

The point isn't that the Sales Qualification Agent is "bad."

It's that its capabilities are extensive, and it requires a careful rollout.

Read the blog linked below to learn how it works, what risks to watch for, and how to roll it out responsibly.

🔗

If you’re thinking about enabling the new Sales Qualification Agent in Dynamics 365 Sales, read this first to understand the risks.

05/21/2026

Today, C5 Insight CEO Geoff Ables is sharing real-world benchmark data from 180+ users across 6 industries who participated in our Microsoft Copilot Proof of Value program.

We'll look at where teams are seeing the greatest productivity gains, which use cases are delivering business value, and what drives long-term adoption.

This session is designed for leaders who need more than general claims about AI productivity.
They need practical data they can use to make confident decisions about Microsoft 365 Copilot.

Save your spot before 1 PM (Eastern): https://c5insight.com/webinar-copilot-roi-benchmarks/?utm_campaign=coschedule&utm_source=facebook_page&utm_medium=C5%20Insight&utm_content=Copilot%20POV%20Benchmarks%20Webinar

Can't make it to the live webinar? We'll be sending the recording to all registrants, so make sure you're on the list!