Two Delegation Strategies

Delegation is a challenge for many entrepreneurs. 

You either:

• Struggle to figure out what work to hand off.
• Have a ton of work but don’t know how to communicate what needs to get done.
• Or (less talked about) even feel a little guilty about giving work to someone else...

Delegation, when done right, isn’t a burden—it’s an opportunity to align your team with the highest-impact work.

1. The Telescope Approach: Start big picture

The first step in effective delegation isn’t where you’d expect. I always tell entrepreneurs to start by zooming out—like using a telescope.

A telescope can either give you a wide view of the entire night sky or zoom in on a specific planet or star. When you’re thinking about delegation, start with the widest lens possible.

Ask yourself:

• What is this person’s role?
• What are the most important projects this month, quarter, or year?
• What actually matters most in the business right now?

Before you get lost in the details of small tasks, take a step back and list the top three most important priorities for the business. This helps you delegate work that actually moves the needle, rather than just keeping people busy.

If you already set clear quarterly goals, this gets easier—you already have the right context in place. From there, you can start focusing on what specific work needs to be assigned.

2. Focus on 80%

Once you have the big picture, think about what this person should spend 80% of their time on. This give you a starting context.

Ask:

• What is this person best at?
• Where should they be focused?
• Are they currently aligned with their highest-value work?

If they’re already spending 80% of their time on the right things, then you’re just tweaking the remaining 20%. But if their focus is off, that’s where you need to start making adjustments.

For example, if someone’s role is to lead brand marketing, then ask: What part of brand marketing does the business need most right now? 

Instead of just handing them random tasks, make sure they’re working on what will have the biggest impact.

Delegating small, unimportant tasks effectively doesn’t help if your team isn’t aligned with the most important work in the first place.

Communicating

One last thing—these conversations don’t have to feel heavy or overwhelming. A client of mine recently shared how much anxiety they felt about these discussions. But the truth is, you don’t have to approach delegation conversations with a super serious tone.

Yes, delegation is important, but keeping it light makes the process easier for everyone. Instead of making it feel like a high-stakes, make-or-break situation, try saying:

• “Hey, let’s take 10 minutes to check in on this.”
• “I love a lot of what you’re doing, I just wanna tweak one thing.”
• “I must not have been super clear before—let’s make sure this is aligned.”

This makes people more open to feedback and less defensive. The more relaxed and collaborative you make it, the more effective the conversation will be.

A lot of times, when you’re frustrated with a team member, the issue is actually pretty small. But in the moment, it feels like everything is wrong. They’re probably doing a great job in most areas, but one small detail is off.

Instead of assuming everything is a mess, take a step back and recognize what’s going well. This makes the conversation with your team much more productive:

1. Acknowledge what’s working – “Hey, I love the work you’re doing on X.”
2. Identify the one thing that needs tweaking: “I think we could improve Y a little bit.”
3. Collaborate on a solut