Ever wonder why your VP Sales sometimes looks at your reports like you handed them a half-eaten sandwich? It’s probably because they’re getting grilled by the C-suite on questions your report doesn’t answer.

I learned this the hard way years ago. My CSO walked into my office, reports in hand, looking like he’d just found out his fantasy football team was mathematically eliminated in Week 3.

“This is great data. Really comprehensive. But I need you to tell me why we’re going to hit the number when the largest investor corners me in the next meeting”

The Questions Your Boss’s Boss Is Actually Asking

Here’s the secret sauce: When you report up, act as you were in your manager’s position and think one level ABOVE your manager. What’s keeping THEIR boss up at night?

The CEO isn’t asking your VP “How many calls did the team make?” They’re asking:

  • “Will we hit the forecast this quarter? Be straight with me.”
  • “Are we burning cash on that new territory that isn’t performing?”
  • “Is our new product actually selling or just collecting digital dust?”
  • “Which deals in the pipeline are real and which ones are wishful thinking?”

How to Be Your Manager’s Secret Weapon

When you start answering these questions BEFORE your boss has to ask you, magic happens. Your boss enters executive meetings as a confident manager.

Here’s what your reporting should really include:

Forecast confidence with actual reasoning – Not “We’re at 82% to goal” but “We’re at 82%, and here’s why that will/won’t become 100% by quarter-end…”

Risk assessment that passes the sniff test – The board doesn’t want to hear “all deals are on track.” That’s fantasy. They want “These 3 deals are at risk because of X, and here’s our mitigation plan…”

Competitive intelligence that matters – Less “competitor X has feature Y” and more “We’re losing to competitor X in these specific situations, and here’s how we’re adapting…”

Resource allocation insights – “Team A is crushing it while Team B struggles because of these specific factors…”

The Career Accelerator Nobody Tells You About

I’ve seen reps get promoted faster not because they hit 110% of quota (though that helps), but because they made their manager’s job easier.

Your manager spends hours preparing for executive meetings. When your reporting answers the tough questions proactively, you become indispensable.

It’s like bringing an umbrella for someone right before it rains. They’ll never forget it.

Next report you create, pause before sending and ask: “If my boss had to present this to the board tomorrow, would they have everything they need?”

If not, you’re just creating more work for them. And nobody got promoted for creating more work for their boss.