How to Delegate Tasks Effectively: A Founder's Guide to Documentation

Here's the brutal truth about delegation: most founders suck at it.

I know because I was one of them. At Simpo, my first startup, I had a team of 21 people and I was still the bottleneck for everything. I'd stay up until 2 AM reviewing copy that didn't need my review. I'd get pulled into Slack threads about decisions that junior employees should have been making.

It wasn't that I didn't want to delegate. I just didn't know how to do it without everything falling apart.

Then I figured out the missing piece: delegation isn't about letting go. It's about documentation.

I'm Yuval, founder and CEO of Glitter AI. After burning out at Simpo and building a new company specifically focused on making delegation easier, I've spent a lot of time thinking about why delegation fails and how to fix it. Let me show you the practical framework I wish I'd had back then.

Why Founders Struggle to Delegate

Before I get into the how-to, let's talk about why delegation is so damn hard for founders.

Control Is How You Got Here

The skills that make you successful as an early-stage founder are exactly the wrong skills for delegation. You built the company by being hands-on with everything. You made it work through sheer force of will and attention to detail.

Now you need to do the opposite. You need to step back and trust other people to do things their way, not yours. It feels unnatural because it is.

I remember the first time I tried to delegate our customer onboarding process. I handed it off to someone on my team with a quick explanation: "Just get them set up and make sure they're happy." Two weeks later, our Net Promoter Score tanked. Customers were confused, the process was inconsistent, and I blamed my team member for not "getting it."

The problem wasn't my team. The problem was that I delegated the responsibility without delegating the knowledge.

Fear Disguised as Perfectionism

Here's what I told myself at Simpo: "It's faster if I just do it myself."

Sometimes that was true. But usually? It was fear talking.

I was afraid that if someone else did it, it wouldn't meet my standards. I was afraid of losing control. I was afraid that if I wasn't involved in everything, I'd become irrelevant to my own company.

Sound familiar?

The thing is, those fears made me the bottleneck. Smart, capable people couldn't step up because I wouldn't get out of the way. And I couldn't scale because everything had to go through me.

The Trust Gap

The real issue underneath all of this? Trust.

Not just trusting that someone can do the task, but trusting that they understand what "good" looks like. Trusting that they'll make the same decisions you would. Trusting that they won't need you to babysit them through it.

You can't build that kind of trust with verbal instructions or a quick Slack message. You build it with clear, documented processes that give people the context they need to make good decisions on their own.

The Documentation-First Delegation Framework

Here's the framework that finally made delegation work for me. I call it documentation-first delegation because it starts with getting the process out of your head and into a shareable format.

Step 1: Document Before You Delegate

This is where most delegation attempts fail. You hand off a task without clearly explaining how to do it, and then you're frustrated when it's done wrong.

Don't delegate the task first. Document it first.

When I started doing this at Glitter AI, everything changed. Instead of verbally explaining how to handle customer feedback (and inevitably forgetting half the details), I recorded myself doing it once. I talked through my thought process, showed exactly where to click, explained why each step mattered.

That recording became the training material. Now when I delegate customer feedback to someone new, I don't need to sit with them for an hour. I just share the documentation and check in to answer questions.

Here's what to include in your documentation:

• The what and why: What is this task and why does it matter?
• The step-by-step process: Exactly how to complete it, with screenshots or screen recordings
• Decision points: Where judgment is needed and what factors to consider
• Common gotchas: Things that often go wrong and how to avoid them
• Quality standards: What "done well" looks like

You don't need to write an essay. Just record yourself doing the task once while talking through it. That's literally what I built Glitter AI to do—turn screen recordings into process documentation that's actually useful.

Step 2: Choose the Right Tasks to Delegate

Not everything should be delegated, at least not yet. Here's how I decide what to hand off:

Delegate tasks that are:

• Repeatable: You do them regularly, not just once
• Time-consuming: They take hours you could spend on higher-value work
• Rules-based: There's a clear process to follow
• Low-risk: Mistakes won't kill the business

Keep tasks that are:

• Strategic: Setting direction, making major decisions
• Relationship-critical: Key investor or customer relationships (at least initially)
• High-stakes: Things where one mistake has serious consequences
• One-off experiments: New things you're still figuring out

I made the mistake at Simpo of delegating high-stakes stuff too early. I handed off a major client relationship before documenting how to manage it. When that team member left, the knowledge walked out the door with them and we lost the client.

Start with repetitive, time-consuming tasks that have clear processes. Once those are humming, you can move up to more complex delegation.

Step 3: Transfer Context, Not Just Tasks

This is the part that most delegation advice misses. You can't just hand someone a checklist and expect them to execute like you would.

They need context.

Why does this task exist? What's the goal? What trade-offs should they consider? When should they ask for help versus make the call themselves?

I learned this when I tried to delegate our content review process. I gave my team member a checklist of things to look for: typos, broken links, tone consistency. She checked all the boxes, but the content still felt off.

Why? Because I hadn't explained the context. I hadn't told her that our content needs to sound like it's coming from a real founder, not a corporate marketing team. I hadn't explained that we prioritize authenticity over polish.

Once I documented that context—the why behind the checklist—her reviews got way better. She started catching things I would have caught because she understood what we were actually optimizing for.

Here's how to transfer context:

1. Explain the big picture: How does this task fit into company goals?
2. Share your decision-making process: Walk through a real example and explain your thinking
3. Clarify priorities: What matters most? What can slide?
4. Set boundaries: When should they make the call versus escalate to you?

This is where screen recording documentation shines. You can literally show someone a task while explaining your thought process out loud. They get to see how you think, not just what you do.

Building Trust Through Clear Processes

I used to think trust was something you just had to give people. Either you trusted them or you didn't.

That's backwards. Trust is built through clarity.

When people have clear processes to follow, they make better decisions. When they make better decisions, you trust them more. When you trust them more, you delegate bigger things. It's a flywheel.

The Progressive Delegation Model

Here's how I delegate any new task now:

Phase 1: I do, you watch

• I complete the task while they observe
• I explain my thinking out loud
• I document it as I go (screen recording makes this easy)
• They ask questions

Phase 2: You do, I watch

• They complete the task while I observe
• I give feedback in real-time
• We identify gaps in the documentation
• We update the process together

Phase 3: You do, I review

• They complete the task independently
• I review the output and give feedback
• We iterate until the quality is consistent
• Documentation gets refined based on what's still unclear

Phase 4: You do, you own

• They own the task completely
• I spot-check occasionally
• They update the documentation when the process changes
• They can now teach it to someone else

This takes longer upfront than just saying "go do this thing." But it's way faster in the long run because you're not constantly being pulled back in to fix things or answer the same questions.

Document Your Standards

One of the biggest mistakes I made at Simpo was assuming people knew what "good" looked like.

They didn't. How could they? The standard was in my head.

Now I document my quality standards explicitly. Not in some vague "make it good" way, but with concrete examples.

For instance, when I delegate blog post reviews, I don't just say "make sure the tone is right." I share examples of posts with the right tone and posts with the wrong tone. I explain specifically what makes each one work or not work.

Examples of what to document:

• Screenshots of correctly completed work vs. incorrect
• Before-and-after examples showing what "polished" means
• Specific metrics that define success (response time, error rate, etc.)
• Decision trees for common judgment calls

The more specific you are, the less micromanagement you need to do later.

Common Delegation Mistakes (And How to Avoid Them)

Let me save you from the mistakes I made.

Mistake #1: Delegating Without Documentation

This is the big one. You explain something verbally, the person nods along, and then they do it completely differently than you expected.

That's not their fault. Verbal instructions are terrible for complex processes. People forget details, misinterpret things, or miss nuance.

Fix: Document the process before you delegate it. Screen record yourself doing it once. That's your training material.

Mistake #2: Delegating Outcomes Without Process

"Just make our customers happy." "Increase engagement." "Improve the onboarding."

These are outcomes, not processes. When you delegate outcomes without explaining the process for achieving them, people either freeze up or improvise poorly.

Fix: Define the specific actions and processes that lead to the outcome. Then delegate the process with room for them to optimize it over time.

Mistake #3: Delegating and Disappearing

The flip side of micromanagement is over-delegation. You hand something off and then ghost because you want to "give them space" or you're busy with other stuff.

Fix: Stay involved during the transition. Use the progressive delegation model. Schedule regular check-ins. Make yourself available for questions. You can reduce involvement over time, but don't disappear on day one.

Mistake #4: Not Updating Documentation

Processes change. If your documentation doesn't change with them, it becomes worse than useless—it becomes actively misleading.

I learned this when someone followed our outdated customer onboarding doc and used a feature we'd deprecated three months earlier. The whole thing broke and we looked incompetent.

Fix: Make documentation a living thing. When the process changes, update the docs immediately. Better yet, give ownership of the documentation to the person doing the task. They'll keep it current because they're the ones using it.

Mistake #5: Delegating Without Authority

You can't delegate responsibility without also delegating authority. If someone has to come to you for approval on every little thing, you haven't actually delegated anything.

At Simpo, I delegated our social media to someone but still insisted on approving every single post. That's not delegation, that's outsourcing with a bottleneck.

Fix: Be clear about what decisions they can make on their own and where they need to check with you. As trust builds, expand their authority.

When to Delegate vs. When to Do It Yourself

Here's a decision framework I use:

Delegate when:

• You've done the task enough times to document it clearly
• The task is taking time away from higher-leverage work
• Someone else could do it 80% as well as you (eventually)
• Mistakes are low-cost or easily reversible
• The task will recur regularly
• You have someone with capacity and interest

Do it yourself when:

• The task is truly one-off and won't repeat
• It requires context that would take longer to explain than to just do
• It's strategically important and you're still figuring it out
• The risk of mistakes is very high
• You genuinely enjoy it and it energizes you
• Your unique expertise or relationships are essential

The key word in that second list is "yourself." Not "keep it yourself forever," but "do it yourself for now."

I do every task myself the first few times. That's when I figure out the nuances, build the process, and create the documentation. Once I've done it enough to document it well, then I delegate it.

The Connection Between Documentation and Delegation

Here's what I've learned after building two startups and a company focused on documentation: you can't delegate effectively without documentation.

Documentation is what enables trust. It's what gives people the context to make good decisions. It's what keeps quality consistent. It's what scales you beyond yourself.

Every hour you spend documenting is an hour you don't have to spend re-explaining, fixing mistakes, or being the bottleneck.

At Glitter AI, documentation isn't a nice-to-have. It's the infrastructure that makes delegation possible. When I hire someone new, I don't need to sit with them for a week. I can share our documented processes and they can get up to speed on their own timeline.

When someone on the team improves a process, they update the documentation. Everyone benefits. The knowledge stays in the company instead of in someone's head.

This is why I built Glitter AI the way I did. Not as another project management tool or task tracker, but as a way to get processes out of your head and into a format other people can actually use. Because that's what delegation actually requires.

Start Small, Build Trust, Scale Up

If you're reading this and feeling overwhelmed, start small.

Pick one task that you do regularly. Something that takes an hour or two each week. Document it. Screen record yourself doing it while you talk through your process. Share it with someone on your team. Walk them through it. Let them try it while you watch.

See what happens.

I'm willing to bet that within a few weeks, they'll be doing that task better than you did. And you'll have freed up hours to focus on the things only you can do.

Then pick another task and do it again.

Delegation is a skill. It gets easier with practice. But it starts with documentation.

Yuval / Founder & CEO, Glitter AI

Frequently Asked Questions

How do I know which tasks to delegate first as a founder?

Start with repetitive, time-consuming tasks that have clear processes and low risk if mistakes happen. Good candidates include customer support responses, social media posting, data entry, and report generation. Avoid delegating strategic decisions, key relationships, or high-stakes one-time tasks until you have more experience delegating.

What's the best way to document a process for delegation?

The fastest and most effective method is to screen record yourself completing the task while talking through your thought process. This captures both the steps and the context. Include what you're doing, why you're doing it, common mistakes to avoid, and what good outcomes look like. You can use tools like Glitter AI to automatically turn these recordings into structured documentation.

How do I delegate without micromanaging?

Use the progressive delegation model: start with clear documentation, do the task together first, then have them do it while you observe, then review their work, and finally let them own it completely. Set clear quality standards upfront, establish when they should ask for help, and schedule regular check-ins rather than hovering constantly.

What if someone doesn't do the delegated task the way I would?

Different doesn't always mean wrong. If they're achieving the desired outcome and maintaining quality standards, their method might actually be better than yours. Focus on outcomes and quality standards rather than exact replication of your process. Only intervene if results are below your documented standards or if they're making decisions outside their authority.

How long does it take to delegate a task effectively?

Plan for 2-4 weeks for someone to become proficient at a moderately complex task. Week 1: documentation and initial training. Week 2-3: doing the task with oversight and feedback. Week 4: independent execution with spot checks. Simple tasks can be faster, complex ones may take longer. The upfront time investment pays off through permanent time savings.

Should I delegate to one person or spread tasks across multiple people?

For each process, delegate to one owner who becomes the expert and maintains the documentation. This creates accountability and deep knowledge. However, cross-train at least one backup person for critical processes so you're not creating a new single point of failure. Document the process so knowledge isn't locked in one person's head.

What do I do if a delegated task keeps getting done incorrectly?

First, check your documentation. Is it clear and complete? Did you provide enough context and examples? Then review with the person doing the task to identify where they're getting stuck. Often the issue is unclear quality standards or missing context, not inability. Update the documentation based on what you learn and provide additional training on specific problem areas.

How do I build trust when delegating for the first time?

Start with low-stakes tasks where mistakes are easy to fix. Provide crystal-clear documentation with examples of good and bad outcomes. Stay involved during the learning phase. Give specific, constructive feedback. Celebrate when they do it well. Trust builds through consistent, positive experiences, not by throwing someone in the deep end.