How to Delegate Without Being a Bottleneck (or Too Standoffish)

There’s a paradox at the heart of growing a service-based business: The very skills that made you successful as a solo freelancer—being hands-on, perfectionist, involved in every detail—become the exact things holding you back when you try to scale.

You hire team members to lighten your load, but somehow you end up spending all day answering their questions. You delegate tasks, but they keep coming back for clarification. You want to empower your team to work independently, but you also don’t want to seem hostile or unavailable.

So how do you strike that balance? How do you delegate in a way that actually frees up your time while still supporting your team?

The Foundation: Document Your Processes

Clay learned this lesson the hard way. When he first started building his team, he tried training people verbally without any documentation. The result? Team members kept coming back with the same questions over and over, no matter how many times he explained something.

Everything changed when he implemented Standard Operating Procedures (SOPs).

With documented processes, his team could reference how to complete tasks without interrupting him constantly. This one shift drastically cut down on repetitive questions and freed up significant time.

**How to create effective SOPs:**

The format matters less than you think. What matters most is what your team will actually use. Some teams prefer detailed written documents with screenshots. Others want quick screen recording videos they can watch and follow along.

Clay’s approach evolved based on team feedback. He initially created written documentation, but his team requested video screen recordings instead. Preston’s team uses a mix—sometimes a 20-minute video feels excessive when a few bullet points would suffice.

The key is asking your team what format helps them learn and reference information most efficiently.

Where to Store Your Documentation

You don’t need fancy, expensive tools. Clay used Monday.com before switching to ClickUp. Preston’s team stores everything as searchable documents in ClickUp. Tools like Trainual exist, but often feel like corporate overkill for small teams.

The most important factor isn’t which tool you choose—it’s how well you organize the information within it.

**Organize by category, not chronologically:**

Don’t just dump videos or documents into one massive folder. Create a logical structure that makes finding information intuitive:

– Administrative (billing, client management, etc.)
– Marketing (social media, email, content creation)
– Project Management (workflows, client communication)
– Sales (proposals, discovery calls, follow-ups)

Within each category, add subcategories. For example, under Administrative, you might have separate sections for invoicing, payment processing, and expense tracking.

When a team member needs to remember how to handle client billing, they shouldn’t have to scroll through dozens of unrelated videos. They should be able to go directly to Administrative → Billing and find exactly what they need.

Set Communication Boundaries (Without Being Standoffish)

Here’s a wake-up call: Clay was getting interrupted by his team about 20 times per day. He got no meaningful work done because he was constantly context-switching to answer questions. Meanwhile, his team got all their work done.

The problem wasn’t that his team was incompetent or lazy. The problem was a lack of structure around communication.

**Clay’s three-tier communication system:**

1. **Emergency that needs immediate attention:** Call me
2. **Can wait until end of day:** Email me, and I’ll respond during my 4 PM email block
3. **Needs discussion or screen-sharing:** Book time on my calendar

This simple framework cut his daily interruptions by 95 percent.

But there’s one more crucial rule that comes before any of these options: **Try to solve it yourself first.**

Before reaching out to Clay, team members had to:
1. Google search for the answer (spend up to 10 minutes trying)
2. Ask a coworker if they know
3. Only then reach out to leadership

You’d be amazed how many “urgent” questions magically get solved when people know they have to wait until 4 PM for an answer. Suddenly problems that seemed impossible to figure out become totally manageable.

The GoPro Story: Encouraging Problem-Solving

Clay shared a telling example. His team purchased GoPro cameras for social media content. He handed the box to a team member, and within two seconds, she tried to hand it back asking him to show her how to turn it on.

Instead of immediately jumping in to help, Clay pushed the box back and said, “Why don’t you take 10 minutes to try to figure this out yourself?”

She figured it out in five minutes.

This perfectly illustrates a broader issue: Many people’s first instinct when encountering something unfamiliar is to immediately ask for help rather than attempting to solve it themselves first.

Setting expectations that people should try to problem-solve before asking doesn’t make you difficult or standoffish. It respects both their intelligence and your time.

Hire for Problem-Solving Ability

Preston makes an excellent point: Successful delegation actually starts in the hiring process.

You want people who can think for themselves and solve problems independently. Technical skills can be taught. The ability and willingness to figure things out is much harder to instill.

When evaluating candidates, look for evidence of resourcefulness, initiative, and independent thinking. Ask about times they solved problems without having all the answers handed to them.

The right team member will see your SOPs as helpful resources to reference, not as substitutes for critical thinking.

Communicate Vision and Philosophy, Not Just Tasks

Beyond tactical procedures, Preston emphasizes the importance of communicating your broader vision and philosophy.

His team knows the kinds of clients they work with and the ones they avoid. When someone reaches out who doesn’t fit their criteria, team members can decline automatically without checking first.

He’s also given his team parameters for decision-making. They can offer discounts up to a certain percentage without approval. Beyond that threshold, they need to discuss it.

This approach gives team members both autonomy and guardrails. They’re empowered to make decisions that keep work flowing, but within boundaries that protect the business.

How to Be Helpful Without Wasting Time

What about when team members do ask questions—especially about things that are documented in your SOPs?

Preston’s approach strikes the right balance. When someone asks a question on Slack, he provides a quick one-sentence answer, then adds: “As a reminder, we have an SOP for this. You can find it here.”

This accomplishes several things:
– Immediately unblocks the person with a quick answer
– Gently reminds them to check documentation first next time
– Doesn’t come across as dismissive or rude
– Reinforces the habit of referencing SOPs

You’re being helpful and kind while still encouraging self-sufficiency.

The Time Audit: Understanding Where Your Day Goes

Clay recommends doing what he calls a time audit to understand exactly where you’re spending your day.

Document a typical 24-hour period in 15-minute increments. Write down everything—work tasks, meetings, admin time, even breaks and distractions. And be honest with yourself. If you spent 45 minutes watching TikTok videos, write that down.

**Include everything:**
– Sleep
– Family time
– Health and exercise
– Actual work
– Interruptions and distractions

The goal isn’t to cut sleep or family time to work more. It’s to get clear-eyed about how you’re actually spending your time versus how you think you’re spending it.

Once you complete your time audit, identify tasks that are essentially $15/hour work—administrative tasks that don’t require your specific expertise or decision-making ability. These are prime candidates for immediate delegation.

You’d be surprised how much time you spend on low-value tasks that could easily be handled by someone else.

The Real Goal of Delegation

Remember, the whole point of delegating is to free up your time to focus on high-value activities: strategic planning, business development, client relationship building, and growth initiatives.

If you’re still getting interrupted 20 times a day, you haven’t actually delegated—you’ve just created a different kind of work for yourself.

Effective delegation means:
– Your team can complete tasks independently from start to finish
– They bring you completed work, not constant questions
– They can make appropriate decisions within defined boundaries
– You’re freed up to work on what only you can do

This doesn’t happen by accident. It requires documenting processes, setting clear communication expectations, hiring the right people, and sometimes saying, “Try figuring that out for 10 minutes first.”

It might feel uncomfortable at first, especially if you pride yourself on being available and helpful. But the alternative is becoming a bottleneck that prevents both you and your team from doing your best work.

Set your team up for success with good systems and clear expectations. Then step back and let them run with it. You might be surprised at what they’re capable of when given the chance.