If You’re Drowning In Work, This Cheatsheet Is For You

I spent almost a decade at Ray Dalio’s hedgefund, recruiting the world’s best leaders. Here is their secret to getting more done.

By Dave Kline Nov 19, 2025

This story appears in the November 2025 issue of Entrepreneur. Subscribe »

Most leaders think about leadership backwards. They see a problem and think, How can I solve this? But the better question is: “Who can help us solve this, and do they have what they need?”

Your role as a leader isn’t to do more work. It’s to constantly optimize the match between work that needs doing and people available to do it.

Here’s how I know this: I spent nine years at Ray Dalio’s hedge fund, Bridgewater Associates, where my job as co-head of our recruiting department was to identify and recruit the world’s best leaders. Today, I train corporate leaders with my own company, MGMT Accelerator.

Not delegating is the single most common problem I see. Leaders are stuck thinking of themselves as the star player on a team, when in fact, their role is much simpler: The best leaders are matchmakers.

Related: I’ve Managed 260 Employees — Here’s How to Tell If Your Leadership Style Is Actually Working

In other words, here’s the simplest way to think about leadership:

Your job = Work to do + People to do it

That’s it. Everything else is noise.

So how do you become a great matchmaker? Below, I lay out my playbook.

Why Leaders Burn Out (And Teams Underperform)

The Doing Trap: When work piles up, leaders default to doing it themselves. But every task you take on is a task someone else doesn’t learn to do.

The Resource Fight: Most leaders fight for more people or accept more work. Few systematically evaluate whether the current match is optimal.

The Resource Fight framework

Use these scripts to get what you need — even if you just need to convince yourself.

How to fight for more people: “Based on our workload, we need two additional people to avoid missing commitments. Here’s the specific impact…”

How to fight for less work: “We’re committed to 12 initiatives. If everything is a priority, nothing is. Which three to four should we focus on?”

How to fight for reality: “Do more work with the same people” is wishful thinking.
Force the choice: “I can deliver X with current resources or Y with additional resources. Which is more important?”

Your Weekly Matchmaking Audit

Every Sunday, spend 30 minutes asking yourself the following questions to spot mismatches between the work and the people doing it.

Work Questions

→ What work is my team doing that someone else should own?

→ What work are we not doing that we should be?

→ What work could we stop doing without meaningful impact?

People Questions

→ Who on my team is underutilized?

→ Who is overwhelmed with the wrong kind of work?

→ What skills do we need that we don’t have?

Match Questions

→ Where is great work being done by the wrong people?

→ Where are great people stuck with the wrong work?

→ What’s one change I could make this week to improve the match?

Related: The 3-Step Framework to Lead with Clarity and Confidence

Common Mistakes

Where leaders go wrong when they try to be matchmakers:

The Hero Complex

TRAP: “It’s faster if I do it myself.”

Fix: Ask: “Who could learn to do this?”

The Comfort Zone

TRAP: Assigning work based on who’s done it before.

Fix: Regularly stretch people into adjacent skills.

Scope Creep Acceptance

TRAP: Saying yes without adjusting existing commitments.

Fix: Every new “yes” requires an explicit “no” to something else.

Advanced Strategies

The Capacity Buffer

Always operate at 80% capacity, not 100%. The 20% buffer allows for unexpected opportunities and strategic thinking space.

The Work Elimination Diet

Each month, ask: “What would we stop doing if we had to cut 20% of our work?” Then stop doing those things anyway.

The People Multiplication Strategy

Instead of asking for more people, ask: “How could we help our current people be 20% more effective?” Often, the answer is better tools, clearer processes, or more focused priorities.

Measuring Your Success

Team Health Indicators

People working in their strengths at least 80% of the time

No one consistently working over capacity

Clear ownership for every major initiative

Regular skill development

Business Impact Indicators

Higher quality outputs

Faster project completion times

Increased team satisfaction scores

More valuable work getting done

Related: This Overlooked Leadership Skill Will Help You Build Trust, Influence Teams and Thrive Under Pressure. Here’s How to Develop It.

What To Do After Reading This

Step 1: List all current work your team is doing.

Step 2: Categorize it using the Matchmaking Audit.

Step 3: Identify your biggest mismatch.

Step 4: Make one change to improve the match.

Remember: Your job is to create conditions where your team can do their best work.

The question isn’t whether you can do the work yourself. It’s whether you’re optimizing the alignment between work and people to maximize impact.

Great leaders own the space between work and people.

Most leaders think about leadership backwards. They see a problem and think, How can I solve this? But the better question is: “Who can help us solve this, and do they have what they need?”

Your role as a leader isn’t to do more work. It’s to constantly optimize the match between work that needs doing and people available to do it.

Here’s how I know this: I spent nine years at Ray Dalio’s hedge fund, Bridgewater Associates, where my job as co-head of our recruiting department was to identify and recruit the world’s best leaders. Today, I train corporate leaders with my own company, MGMT Accelerator.

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