Stop Boring Execs With Your Updates

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In this newsletter, I'll show you exactly how to deliver executive updates that get results instead of glazed eyes.

Most people struggle to communicate value when updating senior leadership. They either ramble through technical details that executives don't care about, or they're so nervous they rush through without making their point land.

Unfortunately, this leads to missed opportunities, stalled projects, and the frustrating feeling that leadership doesn't "get" what you're working on.

The biggest mistake is focusing on activities instead of outcomes.

Here's what typically happens:

• You share what your team has been doing ("We've completed 15 user interviews...")
• You list every technical milestone ("We migrated the database...")
• You explain process improvements ("We implemented new QA procedures...")
• You detail resource allocation ("Three engineers are working on...")

The problem? Executives don't care about your to-do list. They care about business impact.

Here's how to transform your updates into executive-level communication:

Step 1: Orient them to the situation (your "What")

In 30 seconds or less, describe the current situation, problem, or topic you're addressing.

This isn't about selling yet - it's about getting everyone on the same page about what you're discussing.

Instead of: "I wanted to talk about our checkout flow optimization project and all the work we've been doing."

Try: "Our checkout abandonment rate jumped to 68% last month, up from our usual 55%."

Notice how the second version immediately orients them to a specific problem? You're setting context, not diving into solutions yet.

Step 2: Show why it matters to the business (your "So What")

This is where most people fail. They assume executives will connect the dots between their work and business impact. They won't.

You need to explicitly tie your update to one of these three executive priorities:

Profits: Increasing revenue or decreasing costs Market: Expanding market share or reducing time-to-market Exposure: Growing customer retention or reducing business risk

But here's the key: your connection can be DIRECT or INDIRECT.

• Direct Example - Profits: "This checkout problem is directly costing us $400K per month in lost revenue based on our average order value."
• Indirect Example - Profits: "While fixing the checkout won't immediately boost revenue, it will free up our customer service team from handling 200+ 'stuck order' tickets weekly. That's 40 hours we can redirect to upselling, which typically generates $50K monthly."
• Direct Example - Market: "Competitor X just announced a one-click checkout. If we don't match this by Q4, we risk losing our position as the fastest checkout in the industry."
• Indirect Example - Market: "Our slow checkout is damaging our Net Promoter Score. We've dropped 15 points, and customers specifically mention 'clunky purchasing' in reviews. This perception issue could impact our upcoming enterprise expansion."
• Direct Example - Exposure: "These checkout failures are causing 5-star customers to churn. We've lost 12 enterprise accounts worth $2.4M annually."
• Indirect Example - Exposure: "The checkout bugs are creating security vulnerabilities. While we haven't been breached, fixing this reduces our risk of a costly data incident that could damage our SOC 2 compliance."

See how both direct and indirect connections work? The key is making the link explicit, not hoping they'll figure it out.

Step 3: Make your ask crystal clear (your "Now What")

Executives are decision-makers. Give them something to decide.

Never end with: "So that's what we're working on. Any questions?"

Instead, be specific: "I need your approval to accelerate this timeline by adding two contractors for Q4, which will let us capture the holiday shopping season."

Or: "I'd like your input on whether we should prioritize the enterprise features or the SMB improvements first, given our Q1 revenue targets."

The Complete Formula in Action

Here's how it all comes together for a 60-second update:

WHAT (10 seconds): "We discovered that 30% of our API calls are failing during peak hours, causing timeouts for our biggest enterprise customers."

SO WHAT (30 seconds): "This directly impacts revenue - we've had two enterprise clients threaten to invoke SLA penalties worth $200K. But more importantly, it's indirectly damaging our market position. TechCrunch picked up customer complaints on Twitter, and our main competitor just launched an ad campaign about their '99.99% uptime.' If we don't fix this by month-end, we risk losing our 'Most Reliable Platform' rating in the Gartner report."

NOW WHAT (20 seconds): "I need approval to bring in a specialized performance consultant for two weeks at $30K. This investment will save us from the $200K in penalties and protect our $5M enterprise pipeline that references Gartner ratings."

Total time: 60 seconds. Clear situation. Connected impact. Specific ask.

Ready to Master This Skill?

​Join me this Wednesday at 3pm Pacific for a hands-on workshop where we'll practice crafting and delivering executive updates that actually work.

In this 2-hour intensive session, you'll:

• Practice the What/So What/Now What framework with real scenarios
• Get immediate feedback on your delivery
• Learn to handle tough executive questions without rambling
• Leave with templates you can use immediately

Limited spaces available. Hope to see you there.

Preston