The Director's Reporting Challenge: Where AI Might Help

🧭 THIS WEEK AT AI SECOND ACT

Howdy,

It feels a bit like less AI hype recently. This is good news as we all learn to leverage and build with AI rather than digest news and/or chase shiny objects!

Possibly like most topics in life or business, focusing on 1 or 2 (relatively) simple uses cases for improvements with AI can get the ball rolling and show real ROI is a much better approach vs millions of projects and initiatives. Lately, I really like the potential in 2 use case:

• Project Onboarding

• Domain / feature specific training

If you’re enjoying this newsletter, please share it! Forward this to a friend/colleague and have them subscribe at aisecondact.com/subscribe. Thanks!

👉 You can also just hit "Reply" and let me know what you want more (or less) of, or use the poll to give feedback.

My goal is to make this as valuable and practical as possible as we navigate the new AI era. 🚀

🧰 AI NEWS + LEARNING

Here are a few things I found recently:

• OpenAI is working to make AI safer for teens via ‘age prediction’ and parental controls. Definitely necessary with some news stories recently.

• Huge new reports out from OpenAI and Anthropic on how AI is used. This article breaks it down, interestingly > 70% use it for personal use vs work.

  • Particularly:

    • practical guidance

    • seeking information

    • writing

• OpenAI introduced GPT-5 into it’s coding tool, Codex. Enhanced thinking and code reviews. This is definitely ramping up the competition for Anthropic Claude Code and Google Gemini. I will try this out soon.

🗺️ FEATURED INSIGHT

The Director's Reporting Challenge: Where AI Might Help

Does this sound familiar: "Brett, I need executive updates weekly now, not monthly for xyz / blah blah reason"

Translation: Same job, more reporting, same hours in the day.

So here's my question: Where might AI actually help with the reporting grind?

The Reporting Reality We All Know

Monday Morning Scramble:

• Chase 6-12 team leads for status updates

• Get responses in 6 different formats (if you're lucky) including bullet points and novels

• Try to spot patterns while juggling three other priorities

Tuesday Synthesis Struggle:

• Consolidate everything into something executives can actually use

• Add strategic context they need but your teams don't see

• Try to balance "being transparent" with "not creating panic"

• Question whether you're highlighting the right risks

Wednesday Delivery Dance:

• Format everything so it's scannable

• Second-guess your priorities one more time

• Send it off and hope it lands right

Time invested: 4-6 hours/week that you'd rather spend on strategy, team development, or actually solving problems.

The kicker: Next week you get to do it all again.

Where AI Might Actually Help

I've been thinking about this problem through the lens of what AI does well vs. what requires human judgment. Here's my hypothesis:

What AI Could Handle Well:

• Pattern recognition across multiple team updates

• Consistent formatting and structure

• Draft synthesis of raw information

• Risk correlation across different work streams

What Still Needs Human Judgment:

• Strategic context and organizational politics

• Priority weighting based on executive concerns

• Risk assessment considering company history and culture

• Communication tone appropriate for your leadership team

• Decision framing that actually enables action

Experiments Worth Trying

Here are some specific tests any director could run:

Experiment 1: Standardized Data Collection

The Problem: Teams provide updates in wildly different formats 

AI Application: Use AI to create consistent templates, not to collect the data 

Test: Create one standard format and see if it improves your synthesis time

Sample Template:

Weekly Status - [Team] - [Date]

Key Deliverables Completed:
- [Specific accomplishment with impact]

Current Risks (Top 2):
- [Risk] | [Probability] | [Impact if occurs] | [Mitigation in progress]

Next Week's Critical Path:
- [Priority 1] | [Owner] | [Completion target]

Support Needed:
- [Specific request with context]

Experiment 2: Pattern Analysis

The Problem: Hard to spot systemic issues across teams 

AI Application: Feed team updates to AI for cross-team pattern recognition 

Test: Ask AI to identify themes you might miss when reading sequentially

Sample Prompt:

Review these 6 team status reports and identify:
1. Risks or challenges mentioned by multiple teams
2. Resource constraints appearing across workstreams  
3. Dependencies that might be creating bottlenecks

Don't summarize the updates—just flag patterns.

Experiment 3: Executive Summary Drafting

The Problem: Converting operational details into executive insights 

AI Application: Generate first draft, then add strategic context 

Test: Use AI for structure and synthesis, add judgment and priority weighting yourself

The Questions I'm Really Asking

Before jumping into AI experiments, I think we need to be honest about what we're trying to solve:

Time efficiency question: Are we spending too much time on reporting mechanics vs. strategic analysis?

Quality question: Are our current reports actually helping executives make better decisions?

Process question: Is the real problem inconsistent inputs, synthesis complexity, or executive communication?

Value question: What percentage of our reporting time adds genuine value vs. just meets compliance expectations?

Your Reporting Reality

I'm curious about your experience:

• How many hours do you actually spend on executive reporting weekly?

• What's the most frustrating part of your current process?

• Have you tried any AI experiments yet? 

Hit reply and let me know. I'll share interesting patterns in future issues.

The Real Challenge

Here's what I think we're actually dealing with: 

The gap between what executives say they want ("more visibility") and what they actually need ("better decision support").

More reporting isn't inherently better. More useful reporting is.

AI might help us bridge that gap, not by automating everything, but by handling the mechanical parts so we can focus on the strategic insight that actually matters.

Weekly AI strategies for operating executives
— Brett

👉 Hit “Reply” and share your experience — I read every one!

_{Picture by Bernd Klutsch on Unsplash.}