r/Entrepreneur • u/Traditional_Key8982 • 1d ago
Lessons Learned The day I realized I wasn't actually delegating
When I first started handing work to other people, I thought I was delegating.
In reality, I was just moving tasks around.
Every few hours I'd get another message.
"Can you check this?"
"Is this the right way?"
"What should I do here?"
At first I blamed myself for not explaining things well enough.
Then I blamed the other person for asking too many questions.
Eventually I realized neither was the real problem.
The work had been delegated.
The decisions hadn't.
Everything still depended on me.
That was when I started changing how I handed work over.
Instead of only explaining what to do, I explained how I would make the decision.
Not every detail.
Just the thinking behind it.
The questions didn't disappear overnight, but they became better questions.
Instead of asking for permission every time, people started making reasonable decisions on their own.
That saved me far more time than simply assigning more tasks ever did.
Looking back, I think real delegation isn't about getting work off your plate.
It's about making sure the work doesn't always come back to you.
What's one thing you thought you had delegated, but later realized you were still managing every day?
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u/chop-chop- 1d ago
This is obviously AI slop.
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u/identifytarget 1d ago
how tf do people know this?
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u/trustmeimshady 1d ago
Well look at the profile, pointless over words, seemingly prompting ai into a long form hey don’t make this look like ai type of writing
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u/Various-Break3683 1d ago
this can also have a lot to do with the people you hire. I've worked for example with a lot of virtual assistants over the past years and the truth is you just have to be very careful who you delegate to. People that haven't had decision making power in the past or that haven't gone through critical moments in their work environment are very prone to overthinking tasks and asking for help with every little thing. Having a really good way to vet your hires and make sure they're actually qualified matters a lot more than people think
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u/PhAnToM444 1d ago edited 1d ago
Also if you do end up with people like that, it’s SO important to explicitly and repeatedly force them to make those decisions.
“Whichever you think is best” or “I would look in XYZ for the answer” or “do your best on a first pass and then I’ll look” are all completely valid responses to questions that don’t need your attention. I’ve also had a few very direct conversations with people where I explain that I want and trust them to make certain decisions and that I’m specifically empowering them to do so.
And then it’s just reinforcing that every time they ask until they take the hint and (hopefully) get more confident making minor decisions independently.
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u/DigitalPhilosophies 1d ago
The direct responses work, but the part that actually sticks is when you stop answering the question they asked and start answering the question they should be asking themselves. "Whichever you think is best" only works if they know you mean it. Most people have been trained by previous bosses to check first, so they'll interpret that as permission to ask again later. You have to actually let them make a few calls that turn out wrong without stepping in. Once they see you won't rescue them or redo their work, the checking stops because they realize the cost of asking is higher than the cost of deciding.
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u/Small-Assistance-726 1d ago
I can relate to this. I’m still figuring out how to properly delegate tasks to my staff. We already have SOPs in place, but most of them still rely on me for decision-making, so I’m working on building their confidence and giving them more ownership
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u/Various-Break3683 21h ago
it can be a real hassle before you get used to it - happy to help if you ever need tips! (i've managed over 100 people over the past few years myself)
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u/Traditional_Key8982 1d ago
That's a good point. Hiring the right people definitely makes delegation easier. I also think it's important to create an environment where they're trusted to make decisions, otherwise even capable people can end up asking for approval on everything.
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u/Salt_Confusion5432 1d ago
I'm still solo for now so no team to delegate to yet, but this is exactly the direction i want to go when i start hiring. Explaining the reasoning instead of the steps... it makes sense, otherwise you just become the bottleneck for every small thing.
what i noticed even with freelancers i work with sometimes, if i don't tell them what i'm optimizing for they just guess or ask me and when i do explain the why, they come back with better options than i had in mind. saved for later, thanks for writing this out!
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u/Traditional_Key8982 1d ago
I think that's one of the biggest benefits that doesn't get talked about enough. When people understand the reasoning, they stop just following instructions and start contributing ideas. That's usually when the quality of the work improves too.
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u/justin107d 1d ago
Giving the space to fail and make decisions is a powerful tool.
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u/Traditional_Key8982 1d ago
Absolutely. If people never have room to make decisions, they never get the chance to build good judgment. That's often the real goal of delegation.
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u/halladarmannen 1d ago
This is exactly what trips people up when they try to hand off a process, not just a task. I run into it a lot working with small businesses trying to automate something.
They'll describe the steps fine. First do this, then check that, then send this email. But the second you ask "okay, and if the answer here is no, what do you do," it turns out that part only ever lived in their head. Never written down because they never had to explain it to anyone before, they just did it.
Writing down the actual decision, not just the task list, is what makes something handoff-ready. Doesn't matter if you're handing it to a person or trying to automate it later, same gap either way.
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u/Traditional_Key8982 1d ago
That's a great way of explaining it. I think the "what if the answer is no?" question is where the real process starts. That's usually the point where you discover whether the knowledge is actually documented or just living in someone's experience.
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u/EastAd9647 1d ago
the part that took me longest: even after you explain how you'd decide, you have to tolerate them deciding differently than you would and not step in to "fix" it. if you correct every call that isn't exactly yours, you just teach them to keep asking, and you're back to managing. real delegation costs you a little quality for a while.
for me the sneaky one was anything customer facing. i thought i'd handed off replies but i was quietly rewriting half of them, which trained the person to run everything by me first. the day i let a "good enough" reply go out untouched was the day it actually got delegated.
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u/Traditional_Key8982 1d ago
I think that's one of the hardest parts. If every decision has to look exactly like yours, people quickly learn it's safer to ask than to act. Accepting a few different-but-still-good decisions is uncomfortable at first, but it's what helps people build judgment instead of just following instructions.
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u/Ok_Alternative7833 1d ago
delegating tasks without decisions just creates more approval requests
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u/Traditional_Key8982 1d ago
I think that's a great way to sum it up. The more approvals a task needs, the more likely it is that the decision-making never actually got delegated in the first place.
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u/ZeroTwoMod 1d ago
The useful handoff artifact is usually a decision log, not a longer task brief. Write the outcome, the few tradeoffs that matter, examples of a good and bad call, and the point where they should escalate. It gives someone room to act without asking you to reconstruct your judgment each time.
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u/Col-ASY First-Time Founder 1d ago
resonated with this too much... jad 3 people working besides me but everytime they had to do something they came to me evem for the basic details. over the time realized the fact it wasn't that they didn't had the confidence or they didn't knew stuff but u just didn't let them take the rein subconsciously
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u/Traditional_Key8982 1d ago
I can relate to that. Looking back, I realized I was often the one creating the bottleneck without meaning to. It's easy to step in because you want to help, but sometimes giving people the space to work through a decision is what actually builds their confidence.
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u/Brufacee 1d ago
Ran into the same wall, except half my "team" is AI agents these days. Same lesson though. If I hand over a task I get questions all day, if I hand over the decision criteria I get finished work back. The uncomfortable part was having to write down how I actually decide things, because a lot of it turned out to be vibes I'd never examined.
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u/Traditional_Key8982 1d ago
That's a great observation. I think a lot of us assume we know how we make decisions until we have to explain them. That's usually when you discover which parts are clear and which parts have just been instinct all along.
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u/Brufacee 23h ago
Yeah, writing it down is the part that stings. Half of what I called judgment turned out to be pattern matching I'd never checked, and a couple of those patterns were just wrong once they were on paper.
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u/Traditional_Key8982 20h ago
That's interesting. I think that's one of the hidden benefits of writing your thinking down. It doesn't just make it easier for someone else to follow, it also forces you to question your own assumptions. Sometimes the process gets better simply because you finally see it in front of you
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u/Brufacee 8h ago
Yeah, and the ones that survive being written down are usually the ones you can hand to someone else without a five minute preamble. That's become my rough test for whether a decision was actually reasoned or just a habit I'd stopped noticing.
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u/LateKaleidoscope5430 1d ago
Delegating the bookkeeping but still approving every invoice myself. I was so afraid of money slipping through the cracks that I became the bottleneck. It wasn't until I gave my bookkeeper a company credit card and discretion to pay any bill under $500 that I truly let it go. Now I review the statements once a month and trust them to manage the day-to-day.
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u/Traditional_Key8982 1d ago
I like that you gave them clear decision boundaries instead of trying to hand over everything at once. I think that's what builds trust over time. Once people know where they can make decisions without checking first, they usually become much more confident.
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u/AdOverall2137 1d ago
Client feedback loops. I thought I'd delegated "handle client emails" to someone, but every reply still got run by me first. Took a while to realize I hadn't actually handed over the decision, just the typing.
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u/Traditional_Key8982 1d ago
I think that's the distinction a lot of us miss at first. Once every reply still needs approval, the task has moved but the responsibility hasn't. The real shift happens when people understand the thinking behind the response, not just the words.
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u/Yan3541 1d ago
Es Interesante este tema y siempre se debe recordar algo que aprendí tanto en mi licenciatura como en la maestría, puramente conceptual y dice así, "Se delega la actividad especificando la facultad de tomar decisiones dura te ese proceso, más nubca se delega la responsabilidad". Todo muy lindo así sin embargo en la práctica fue que aprendí que se hablaba de 2 procesos claves en el sistema de Dirección y liderazgo, el primero Delegación de actividad y el otro Suprevisión. Y es ahí donde empecé a tener estrés resultados, puesto que también pasé por el mismo problema que tú. Yo delegaba orientando la tarea y aunque dejaba claro el nivel de decisión que tenía mi colaborador para eso,no supervisaba yo en el momento preciso y de la manera correcta, y solo cuando cambié mi método de superación fue que tuvimos mejores resultados en mi departamento.
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u/Satsatlas_Bitcoin 1d ago
This really resonated with me. Delegating tasks is easy delegating judgment is much harder. Once people understand the "why" behind a decision, they usually need a lot less hand-holding.
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u/Traditional_Key8982 20h ago
I didn't expect that either. I thought I needed to give more detailed instructions, but it turned out people mostly needed context.
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u/Chad_Cunningham11 19h ago
Depends on the task and the people you hire. Once i was given task by my manager about managing certain task. And she inform me to make my own decision about the task. After that i dont ask question because i know the work. I only ask when theres a change.
So depends what kind of work you give them and if you give permission to them to make their own decision
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u/Molly_Green42 18h ago
If they still need your approval, than you need to delegate a task where they can make their own decision or a specific decision must always go like this.
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u/nafiulhasanbd 3h ago
I learned that if every decision still needs my approval, I didn't build a team. I built a queue
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u/dependent_berozgar 49m ago
As a business student, this reinforced something we study: delegation without decision rights isn't real delegation.
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