Sep 23, 2021
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 min read

How NOT to Delegate: This Delegation Mistake Cost Me Years (but was fixed in seconds)

Your bootstrapped online business is growing and it feels amazing.

But you can’t do everything yourself any longer. You need help to take your business to the next level, so you’ve decided to delegate a few tasks to freelancers. 

You make your first hire and delegate your first few tasks. 

It works! The future looks bright; four hour work week style. You can already see yourself sipping coconuts on the beach in Thailand while a remote team grows your business. 

You continue to delegate but notice something alarming. It seems the more you delegate, the busier you become. Even though there are more hands on deck, you feel you’re walking backwards. You have more decisions to make but less time to make them. 

A freight train of anxieties keeps you awake as you lay down to sleep each night. There’s so much to do tomorrow. The coconut beach bar seems to be sliding further into the distance.

It doesn't have to be like this. 

You're making a simple delegation mistake, and fixing it starts with a simple mindset shift.

Are you making this delegation mistake?

I attended the school of hard knocks to learn delegation. Investing over $300k hiring on Upwork alone, I learned how to hire and manage a team of remote freelancers, and delegated a myriad of tasks.

But the most valuable delegation lesson came from management consultant Mads Singers during a business mastermind. 

I sat in the hot seat and explained my business and its growing pains. 

Mads opened his mouth and solved my problem in two seconds flat. His answer highlighted the delegation mistake I’d been making for years. 

“Don’t delegate tasks. Delegate responsibilities.

For a moment I was overcome with doubt. I was expecting something else. Something complex; like a long distance relationship. 

But a quote about keeping things simple urged me to take his advice 

“If the answer isn’t simple, it’s probably not the right answer.” - Tim Ferriss

The problem was around how I was delegating.

And this tiny shift has huge consequences. 

Delegating tasks vs responsibilities 

When you delegate a task you emphasize the process

You figure out how to do something, document the process, then hire someone to execute. This is the ‘universal task delegation formula’.

“Here are instructions to complete X” You say. “Please follow this recipe and report back to me when done.”

how to delegate meme

Task delegation makes sense but only in the beginning. And for your first, second, maybe even third hire, it works flawlessly. You’re even rewarded with a nice little dopamine rush every time you delegate as confirmation

But you are the designer and owner of the process. Someone follows your SOP. And if something isn’t clear, the question is directed at you. Finally; you are the one who decides whether the task is complete.

To top it all off you learn that SOP's are rarely ‘set and forget’ and hence they need constant updating.  

If you keep delegating tasks while your business grows you create a bottleneck. You spend more time updating SOPs and micro-managing task completion to try to get ahead of the game. 

You sacrifice time which should be spent on the high-impact work in your business. This is a huge opportunity cost.

This is the point of failure for task delegation. What was once a tool for growing your business, starts holding you back. This is a sign it's time to do things differently. Its time to level up your delegation game.

Do you think Steve Jobs sat down in his office and figured out how to do every single task at Apple, made an SOP, and then delegated it downwards?

Of course he didn’t, and neither should you. So as your business grows you must be ready to transition from delegating tasks to delegating responsibilities.

When you delegate responsibilities you emphasize the outcome

“You’re in charge of delivering X, and I believe in you, so you can do it however you want” you say. “I do it this way, but I'd love you to find the best way to do it.”

You care about the outcome more than the process. You’re paying your team to handle the process. And the best way to ensure your team takes ownership of the process is by having them design the process.

Sure, you can still create the first SOP, just don't go overboard. Rather than a step-by-step-no-thinking-required guide, simply screen record yourself while doing the task and thinking out loud. Or better yet, find a YT video. This becomes version 1 of the process, and it's your team's responsibility to improve it.

When delegating, you send an empowering message to your team. “I trust you, and believe in you”. Your team is encouraged to think critically and creatively, and because of this, they’ll often find a better way of reaching the outcome. 

So if you’re experiencing a building sense of ‘the- more-I-delegate-the-busier-I-become’ anxiety, take this as a sign that it's time to stop delegating tasks and start delegating responsibilities.

How can you make this transition?

How to transition from task to responsibility delegation

It begins with a simple mindset shift that forces you to communicate with, and manage your team differently. 

Mads, the management consultant mentioned earlier, created a course called Effective Management Mastery that teaches business owners how to 5x their output without working 80+ hours per week through effective management skills.

While going through this course I picked up two powerful strategies that helped me transition my delegation style.

Use language that empowers, rather than instructs

The first is about changing the way you communicate with your team when delegating.

Rather than creating then handing off a process to a team member, your conversations should empower your team and allow them to create their own processes. Make it clear that you trust them to take responsibility.

For example, imagine you’ve hired Steven to create a YouTube channel for your business.

If you were delegating this as a task, you would first spend time learning and outlining the process. A conversation would then follow.

“Hi Steven, how are you? I have this YouTube video creation process I want you to follow. Here’s a guide I made showing you how to do it, please create 3 videos each month and report back to me for feedback”

Steven might follow the steps and get the task done. But he probably won’t improve the process or knock it out of the park. And that's your fault; you gave him the process and told him what to do. Steven is just doing what you told him.

But if you were delegating the responsibility, the conversation would be be different:

“Hi Steven. I love the way you present and you seem to have a knack for explaining things. I don’t. So I want to give you the responsibility for creating our YouTube channel. Here’s a very basic process I put together, but you’re a smart dude so I’d like you to build upon this process and find the best way to make these videos. I’ve done a little research and learned that video engagement rates of 50% or higher is an important metric for YouTube video growth, so I’d like you to create 3 videos per month that achieve engagement rates of 50% or higher. Will you handle this responsibility for me?”

If Steven is motivated he’ll take this and run with it. He’ll flesh out the process himself, and he’ll feel excited as he becomes the video expert in your team. All video related questions within your company should now be directed at Steven, naturally. Not you. He’s the video expert, after all!

Answer your team's questions with your own questions

The second strategy to help you transition from task to responsibility delegation requires you to form a simple habit of answering questions with your own questions.

Back to Steven, the soon-to-be video expert in your team, for an example.

Imagine Steven asks you: “How do I ensure our video engagement level stays above 55%?”

You could figure this out, give Steven the answer and send Steven him on his way.

But you’re teaching Steven a bad habit. He learns that IF he has a question, THEN he should ask the boss. ‘Every time I have a question, I ask the boss.’ 

And this problem only compounds as your team grows. Suddenly you have a constant stream of questions pulling you away from the work that matters. You’re in bottleneck territory.

But what if you answer his question with your own question instead?

“What do you think, Steven? What are the options? When you’re watching a video, what is it that makes you watch until the end?”

Resist the temptation to hand out the answer, and rather, help your team reach the answer themselves.

In some cases you might completely disagree with Stevens' answer. Maybe he suggests lying to the viewers to keep them engaged. Follow up with a clarifying question, such as:

“So what you’re saying is; we lie to our viewers and expect them to trust us enough to come back for the next video? If someone lied to you, would you return to their business? What happens then?".

Answering questions with your own questions encourages thinking and hence, learning. If you simply answer your team's questions you rob them of an opportunity to grow. What was that proverb about giving a man a fish, versus teaching him how to fish again?

To recap: use empowering language, and answer questions with questions. These are just two of the simple yet powerful strategies I learned in Mads’ course on effective management and delegation, that will help you transition your delegation style.

And this stuff works; the above example is real. Steven is a real person and we had similar conversations around growing a YouTube channel for our coffee education business HomeGrounds. Steven quickly took responsibility for the channel's growth, became the expert, and grew it himself with amazing results.

Final thoughts

You’ll start growing your business by delegating tasks, but can only continue to grow by delegating responsibilities.

If you’re feeling overwhelmed despite a growing business, take it as a sign. A good sign. These are growing pains and It’s time to stop delegating tasks and start delegating responsibilities.

Make this transition and you’ll be sitting on the beach sipping those coconuts in no time.

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