Managing Up 101: Perfect Your Problem Pitch

Part 3 of 5 in our Managing Up Challenge for Leaders: How to Bring a Problem to Your Boss (Without Causing Stress)

Nov 06, 2024

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Three people – an Analyst, a Diplomat, and an Explorer – are in an office setting. One man in purple works on a laptop, while a woman in green stands nearby, talking to a man in yellow wearing sunglasses. Below, the words 'Managing Up Challenge Day 3' are shown. — Image from 16Personalities.com

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I used to participate in a daily standup of leaders where we each got two minutes to share our focus areas and blockers with the C-suite.

One morning, I watched in silent discomfort as a peer turned his two-minute update into a twenty-minute saga. He didn’t just bury the lede – he excavated every possible detail, explored tangential issues, and dragged the entire room into a circular discussion that left everyone confused about the actual problem.

Maybe you’ve been in a room like that, too. Maybe (let’s be honest) you’ve even been that person. Here’s the lesson: how you bring problems to your boss matters just as much as the problems themselves.

Whether you’re escalating issues to a C-suite executive or your immediate supervisor, your ability to frame problems effectively, propose solutions confidently, and time your discussions strategically can make the difference between being seen as a problem-spotter or a problem-solver.

Today, on Day 3 of your Managing Up Challenge, we’ll explore three proven strategies that will help you master the art of bringing problems to your boss – without making everyone wish they had never asked.

Day 1: Anticipating Your Boss’s Needs
Day 2: Winning Buy-In by Understanding Your Boss
Day 3: Bringing Problems to Your Boss the Right Way (You Are Here)
Day 4: Disagreeing Respectfully and Productively
Day 5: Adding Real Value as an Effective Leader

Cut Through the Noise: Frame Problems With Crystal Clarity

When bringing issues to your boss, it can be tempting to regurgitate every detail of the situation. But sharing all of that background info can take so. Much. Time. and it’s probably irrelevant anyway.

Chances are, your boss needs three key elements to make a decision:

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