On the Ground Interview

This is where theory meets reality. Where polished documentation runs into "Yeah, but that's not how we actually do it."

Why This Interview Matters

The people doing the work know things leadership doesn't.

They know the workarounds, the manual steps hidden in "automated" workflows, the time sinks that don't show up in reports, and the tools that get ignored.

The gap between what leadership thinks is happening and what's actually happening is where your biggest AI opportunities live.

What You're Trying to Learn

1. Daily Role & Responsibilities

Ask questions like:

"Walk me through a typical day or week in your role."
"What are the 1-3 most common tasks you perform daily?"
"How much time goes to core responsibilities versus administrative or repetitive tasks?"

Why this matters: If someone spends 60% of their time copying data between systems, that's an automation opportunity.

2. Step-by-Step Process Deep Dive

Pick one specific, common task and ask:

"Walk me through the exact steps to complete [task]."
"Which part is most manual or time-consuming?"
"What information do you need and where do you get it?"

Why this matters: Step-by-step walkthroughs reveal things like: pull data from System A → copy to spreadsheet → manually format → paste into System B. Each step is a potential automation target.

3. Tools & Frustrations

Ask questions like:

"What software do you spend most of your day in?"
"What's most frustrating about your tools?"
"Is there any double-entry of data or copying-and-pasting between systems?"

Why this matters: Tool frustration = opportunity. When people complain about switching between five systems or re-entering data, those are high-value targets.

4. Pain Points & Wishlist

Ask questions like:

"What's the most boring or repetitive part of your job?"
"If you had an assistant, what tasks would you give them immediately?"
"How do you track your work or report progress?"

Why this matters: The "if you had an assistant" question is magic. People immediately name the tasks they hate—perfect AI candidates.

What You Should Walk Away With

By the end of this interview:

✅ Clear picture of how they actually spend their time

✅ Step-by-step breakdown of at least one common process

✅ List of tools and frustrations

✅ Documented workarounds and manual steps

✅ Their wishlist of tasks they'd delegate immediately

The Gap Is the Gold

Compare the stakeholder interview (leadership's view) with the on-the-ground interview (frontline reality).

Leadership: "Onboarding takes 3 days."

Frontline: "It's supposed to take 3 days, but we wait 2 days for approvals, so it's really 5."

That gap is where your opportunities live.

Next Step: With both views captured, you're ready to identify where decisions get stuck—the bottlenecks that slow everything down.

This is where theory meets reality. Where polished documentation runs into "Yeah, but that's not how we actually do it."

Why This Interview Matters

The people doing the work know things leadership doesn't.

They know the workarounds, the manual steps hidden in "automated" workflows, the time sinks that don't show up in reports, and the tools that get ignored.

The gap between what leadership thinks is happening and what's actually happening is where your biggest AI opportunities live.

What You're Trying to Learn

1. Daily Role & Responsibilities

Ask questions like:

"Walk me through a typical day or week in your role."
"What are the 1-3 most common tasks you perform daily?"
"How much time goes to core responsibilities versus administrative or repetitive tasks?"

Why this matters: If someone spends 60% of their time copying data between systems, that's an automation opportunity.

2. Step-by-Step Process Deep Dive

Pick one specific, common task and ask:

"Walk me through the exact steps to complete [task]."
"Which part is most manual or time-consuming?"
"What information do you need and where do you get it?"

3. Tools & Frustrations

Ask questions like:

"What software do you spend most of your day in?"
"What's most frustrating about your tools?"
"Is there any double-entry of data or copying-and-pasting between systems?"

Why this matters: Tool frustration = opportunity. When people complain about switching between five systems or re-entering data, those are high-value targets.

4. Pain Points & Wishlist

Ask questions like:

"What's the most boring or repetitive part of your job?"
"If you had an assistant, what tasks would you give them immediately?"
"How do you track your work or report progress?"

Why this matters: The "if you had an assistant" question is magic. People immediately name the tasks they hate—perfect AI candidates.

What You Should Walk Away With

By the end of this interview:

✅ Clear picture of how they actually spend their time

✅ Step-by-step breakdown of at least one common process

✅ List of tools and frustrations

✅ Documented workarounds and manual steps

✅ Their wishlist of tasks they'd delegate immediately

The Gap Is the Gold

Compare the stakeholder interview (leadership's view) with the on-the-ground interview (frontline reality).

Leadership: "Onboarding takes 3 days."

Frontline: "It's supposed to take 3 days, but we wait 2 days for approvals, so it's really 5."

That gap is where your opportunities live.

Next Step: With both views captured, you're ready to identify where decisions get stuck—the bottlenecks that slow everything down.