The Eisenhower Matrix Is Wasted on To-Do Lists. Use It to Run Better 1:1s.
Why Urgency Always Wins (And How to Stop It)
Your best rep just told you she’s not sure she can close the Riverside deal.
Not because of price. Not because of competition.
Because she doesn’t know if the superintendent actually cares about what your product does—and she’s been working this deal for three months.
You have 45 minutes scheduled with her this afternoon. If you spend most of it reviewing pipeline hygiene and talking about the other deals she’s working, you’ll both walk away feeling productive. She’ll give you confidence on her forecast. You’ll give her a few tactical suggestions.
And next week, Riverside will still be stuck.
This is the trap of the unprioritized 1:1.
Not that the conversations are bad. It’s that they consistently mistake motion for progress—and urgency for importance.
The Eisenhower Matrix, usually relegated to productivity blog posts about email management, is actually a better tool for human development than task management. When you apply it to 1:1s, it becomes a forcing function for the question every sales leader should ask but rarely does:
What will most help this person succeed over time?
The Default Patterns
Most recurring 1:1s fall into one of three traps:
The Pipeline Interrogation: You walk through every deal. You ask the same questions. You update the same fields. It feels rigorous, but it’s just reporting disguised as leadership.
The Emotional Processing Session: You listen. You empathize. You validate. All of that matters—but without direction, it becomes therapy without the license.
The Weekly Fire Drill: Whatever screamed loudest that week gets the airtime. A difficult prospect. A contract hiccup. An internal process that broke. By the time you’re done putting out fires, there’s no time left to prevent the next ones.
None of these patterns is wrong. The problem is when one of them dominates every conversation.
Without an explicit model for prioritization, urgency wins by default. And development—the thing that actually compounds—gets postponed indefinitely.
Reframing the Matrix
The Eisenhower Matrix sorts work into four quadrants based on two dimensions: urgency and importance.
But here’s the reframe: in 1:1s, those quadrants aren’t about tasks. They’re about conversations.
Each quadrant represents a different type of dialogue—and each deserves intentional time.
Quadrant 1: Immediate and Consequential
“What cannot wait?”
This is the quadrant most managers live in. It includes:
A deal at risk this cycle
A political misstep with a key stakeholder
A forecast issue that affects your roll-up
A rep who is blocked and spinning
These conversations deserve time. They require decisions, not just discussion.
But here’s the discipline: time-box them.
Fifteen minutes to diagnose the problem, clarify options, and assign ownership. If you can’t resolve it in that window, you’re either missing information or avoiding a hard call.
The mistake isn’t addressing urgency. It’s letting urgency consume the entire meeting—and mistaking activity for leadership.
Quadrant 2: Important and Developmental
“What will matter months from now?”
This is where great managers separate themselves.
Quadrant 2 includes:
Skill development (discovery, negotiation, messaging)
Account strategy and long-term positioning
Territory planning and pipeline architecture
Career growth and role progression
Pattern recognition across deals
None of this is urgent. All of it is important.
And it’s the easiest quadrant to neglect—because nothing in it will break this week.
Back to your rep with the Riverside deal.
The urgent conversation is about whether the deal will close this quarter. That belongs in Quadrant 1.
The important conversation is about why she still doesn’t know if the superintendent cares three months in. That’s a discovery problem. A qualification problem. Maybe a confidence problem.
That conversation belongs here.
If you don’t make time for Quadrant 2, you’ll spend every 1:1 reacting to problems that could have been prevented. You’ll be a bottleneck, not a multiplier.
Quadrant 3: Pressing but Delegable
“What feels urgent—but isn’t leadership work?”
This quadrant is full of noise:
Internal process questions with documented answers
Administrative friction that someone else should own
Emotional urgency without strategic consequence
Your rep needs a contract template. Your rep wants to vent about Marketing’s latest campaign messaging. Your rep is confused about how to submit expenses.
All of these feel urgent to the person experiencing them. None of them require your time.
The discipline here is twofold:
First, decide once. Answer the question, document the answer, and push it to the right level. Don’t let the same question surface in three different 1:1s.
Second, teach ownership. If your rep brings you a problem that they could solve themselves, resist the urge to just solve it. Ask: “What have you already tried?” or “If I weren’t available, what would you do?”
Your job is not to absorb urgency. It’s to reduce future interruptions.
Quadrant 4: Neither Useful nor Productive
“Why is this taking airtime?”
This quadrant requires honesty.
Examples:
Rehashing old losses without extracting insight
Complaining without intent to change
Hypothetical scenarios disconnected from real deals
Rumination disguised as reflection
Sometimes people need to process. But processing without progress is just noise.
If a conversation lives here, your job is to acknowledge, close, and redirect.
“I hear you. That sounds frustrating. What do you want to do differently going forward?”
Time reclaimed from Quadrant 4 should be reinvested in Quadrant 2.
A Structure That Works
Here’s a simple agenda that makes prioritization visible:
1. Immediate issues requiring decisions (15 minutes) What’s urgent and consequential? What needs to be decided or unblocked today?
2. Development, strategy, and long-term growth (20–25 minutes) What skill, pattern, or capability will make this person more effective in three months? This is your highest-leverage time.
3. Triage and delegation (5–10 minutes) What feels urgent but can be owned elsewhere? What process friction can we eliminate?
4. Commitments and reflection (5 minutes) What are you committing to? What am I committing to? What did we learn today?
The structure itself sends a message: development is not optional. Urgency will not hijack the conversation.
Teaching Reps to Prepare
Over time, teach your reps to label their agenda items using the same language:
Immediate issue needing a decision
Skill or strategy I want to improve
Item I should own going forward
This does two things.
First, it trains prioritization. Your reps start recognizing the difference between urgent and important—and stop treating everything like a fire.
Second, it reduces dependency. When reps come prepared with clarity about what kind of help they need, they become better at knowing when they don’t need help.
What Changes
Leaders who run prioritized 1:1s see:
Fewer emergencies, because problems get addressed before they metastasize
Better judgment, because reps learn to distinguish signal from noise
Higher trust, because people feel developed, not just managed
Not because they work harder. Because they focus on what compounds.
The Cost of Drifting
Here’s what happens when you don’t prioritize:
Your best reps stop bringing you development conversations because they know you’ll redirect to this week’s forecast.
Your struggling reps bring you the same problems every week because you’re solving them instead of teaching them to solve their own.
Your 1:1s feel busy but not productive. You leave tired. They leave unchanged.
And six months later, you wonder why your team hasn’t grown.
Final Thought
Urgency always shouts. Importance rarely does.
The Eisenhower Matrix isn’t a magic trick. It’s a reminder that not all conversations are equal—and that the ones that matter most are the ones you’ll be tempted to skip.
Great leaders design their 1:1s to hear both urgency and importance—and to choose wisely.