The best kind of annoying: what good help actually looks like

There's a version of "getting help" that looks like someone just taking tasks off your plate, never asking questions, never pushing back, never making you think harder than you wanted to...

That sounds great. 

And it can be… kinda. 

I know you’re thinking “What? But Olivia, that sounds amazing! You’re saying my problems are just going to go away? How is this not exactly what I need?”

The answer is pretty simple: the help that feels easiest at the start is often the help that costs you the most later.

What average (not great) help looks like

Ok, before you jump down my throat, let me explain! I get it, the idea of tasks magically disappearing sounds lovely. 

The problem is that when someone just does the isolated task, the system as a whole isn’t considered and things get messy. 

Your onboarding process is a well oiled machine, must be because you don’t ever hear about it. Right??

Cute.

It’s a disaster that you never paid attention to because it was all happening. When you pull back the curtains you realize there are 5 different spreadsheets involved, everything is manual and if your “help” is off, your business stops. You have no idea how things happen or when. Not to mention you’re paying for tasks that a robot could be doing. 

What else happens? The questions never stop. What’s this? How do I reply to this? How do you want to handle this? What do you want me to do? There’s no higher level thinking because they don’t actually understand your business. 

Ok, now that we’ve gotten that out of the way, let’s get back to the good help! 

Good help is supposed to feel uncomfortable at first

No, not in a “you make my skin crawl” kinda way, in a "wow, nobody has ever asked me that before" or “Oh, I’ve never thought of that” kinda way. 

Task completion and help aren’t the same thing, this goes for life and business. 

Good help starts with understanding the actual problem

Most of us don't realize we've already decided what the problem is before we ask for help. We identify the thing that's frustrating us, the thing that's taking too long, or the thing we don't want to do anymore, and we assume that's what needs to be fixed.

Sometimes we're right.

Most times we're treating the symptom and never questioning what's causing it.

Most people come to me with a list of specific tasks they want help with. 

Almost never is the task they come to me with the thing we actually do. Why? Because they’ve only looked at the surface. They’ve identified “I don’t like this task” or “this task has stressed me out”. 

What I actually do is figure out what's underneath it.

A friend of mine mentioned offhand that he hadn't gotten his prescription renewed in a while… When I asked how long he said OVER A YEAR! Yikes. 

So, me being me, I said "do you want me to message you every day until you book the appointment?" He said "that's annoying... but interesting."

I took that as a yes.

Three days later he booked it.

I couldn’t make the appointment for him (the actual task), but I could make sure it stayed at the top of his mind until it happened (help).

I have another friend who had an issue with a haircut. 

She'd been cutting her own hair for years because she didn't know how to ask for what she wanted at a salon. We were sitting at lunch chatting about it and I did what I do… I asked questions. 

“Try to explain it to me” 

“Ok, so you want it this way or that way?” (hand motions were involved)

“Nice, so do you want it shorter, or a similar length?”

Then I took all her own words, put them into my robot friend, added a picture of her and asked for a mockup of what she had said… voila! That was it. She now had a visual of what she wanted. 

Once we confirmed the visual, I asked “How would I explain this to a hair stylist”. Now we had it in writing. 

But it didn’t stop there. We were across the street from a hair salon so we went online, booked the appointment and I went with her to tell the hairdresser what she wanted - it had clearly been a mental block for her, so I didn’t want her to go through it alone. 

Stayed, watched the haircut and at the end said to the hairdresser “How would you explain this to someone who wanted this hair cut” wrote down the answer and then said “can you take pictures of what angles would be helpful for you if you had to do this again?”

Short-term problem solved - get a haircut.

Long-term problem solved - make it easy to get future haircuts.

The haircut that day was a task, but it wasn’t the important part. 

This is the part we get wrong

We assume good help should feel efficient. 

We expect someone to hear our problem, nod confidently, and immediately start doing the thing we asked them to do. When that happens, it feels productive. It feels like we're making progress.

If someone starts asking questions instead, it can feel like they're slowing everything down.

"Why do you do it this way?"

"What happens after that?"

"Who decided this process?"

"What are you actually trying to accomplish?"

Those questions can feel frustrating because they interrupt the momentum. 

They force us to stop moving long enough to think and make us explain things we've never had to explain before.

This annoying part… is where the magic happens. 

Good help isn't trying to make your life harder. It's trying to make sure you don't have to keep solving the same problem over and over again.

The best kind of annoying is when someone cares more about solving the right problem than simply completing the task. Someone who's willing to slow down, ask the uncomfortable question, challenge the obvious answer and dig a little deeper before they start fixing things.

Why the questions matter

The questions at the beginning aren't there because I like making things complicated.

They're there because I don't want to become another person you have to manage.

A lot of support looks efficient at first. You hand someone a task, they complete it, send it back, and wait for the next instruction… On paper, that's help.

BUUUUUT, if every new situation requires another explanation, another decision, another message from you... have you really removed work from your plate? Or have you just changed what kind of work you're doing?

That's why the beginning of working with me feels different.

I ask about your business, your goals, your decision-making, your clients, your processes, and sometimes things that seem completely unrelated to the task you hired me for.

I'm curious because every answer helps me build a mental model of how your business actually works.

Once I understand that, I don't just know what to do. I know why you're doing it, and can make it better.

That's the difference.

Someone who only knows today's task can finish today's task.

Someone who understands your business can spot tomorrow's problem before you even notice it, make decisions the way you would,  improve a process instead of simply following it and they can connect pieces that don't seem related yet.

It takes more work up front, asks more of you in the beginning, but over time, it asks far less of you.

When someone truly understands your business, they don't just take work off your plate for today, they make sure it doesn't find its way back tomorrow.