How Managing Upworkers Made Me a Much Better Manager

In my 20+ year career I’ve probably managed a few hundred employees.

From the years of 1999 - 2008 I probably managed close to 100 as a strategy consultant managing teams.

From the years of 2008 - 2014 I managed 100+ across being a Sr Director at Visa Inc. and then CEO of Groupon Ukraine.

And then from 2014 - 2020 I managed another 50+ as a product leader at Lazada, Wayfair, and Pomelo Fashion.

I’m saying all of this to say that I managed my fair share of people. I’ve interviewed, hired and onboarded many times and honestly thought I was pretty good at it.

But it was when I started hiring lots of Upwork freelancers starting early 2021 (i’ve since managed ~200 of them) that I consider that I really took ‘managing’ to the next level.

And in this article i’ll explain why.

Managing freelancers helped take my clarity to the next level

When I first started working with freelancers I can honestly say it was very painful. They were of varying levels of quality and reliability.

A few times I just wanted to give up.

But then I realized an extremely important lesson in clarity. If I wrote out each of their tasks in very simple words on a clickup task and asked them to comment anytime they were stuck or needed clarity… an amazing thing happened.

They started to progress in a very consistent way. And if they didn’t… I learned to churn them out fast and get someone else that could.

So the key lesson here was… boil down absolutely everything I do into fixed scope tasks that are extremely clear.

It took more effort from my side… but it also made me think a lot more about what I actually wanted.

No longer was I giving sometimes vague instructions as I was for the ~20 years before. Everything was concrete. I needed to write tasks so that they could be understood by the lowest common denominator.

And this turned out to be a far better way to scale.

Making things clear works not just with freelancers... it is also very powerful with employees

When I tell this story to some folks they assume that this is a good way of working with freelancers, but it’s not needed with employees.

And I always tell them I strongly disagree.

You will always get more out of your team by working in this way in my view. I have done it with employees and contractors alike the past 3-4 years, and I’m very confident in this.

Now i’ll explain why.

When you’re working with employees…. you can still have them write out their tasks and add you as a follower. It is not that i need to micromanage each one and write their tasks for them.

And if they write out each of their tasks with a clear scope and add me as a follower, I am essentially checking that they have the same understanding of what to do as me.

And that is very very powerful.

I challenge you to do this test

If you’re managing the ‘traditional’ way I challenge you to do a test. The next time you have 1-1’s with your direct reports… ask them to repeat back to you the action steps that you discussed with them during the meeting.

And count how many times it differs from what you had intended.

Often it will differ massively. Especially if you are the type of manager who goes off on long diatribes… thinking that the more that you talk the clearer it is for them.

What happens as a result?

Well they will have shot off and spent the next week working on their priorities with a slightly different interpretation of them than you.

And that is wasteful.

I almost never have this happen anymore. Because we can both point back to the scope of the card, which can be considered the ‘definition of done’.

If it’s written well, it tells them exactly what is expected and at what level of depth.

Comments are the other tool to managing in a very clear way

This is the other thing that happens using my ‘Everything as a Task’ method. You’re increasing the clarity of the task throughout the whole week.

Because the directive to each person is…. “anytime you get stuck or something is not clear.. just comment on the card.”

And I respond to these comments very quickly (usually within 1-2 hours). My comments help make them clearer or sometimes help guide on what the priority is.

So that we end up working in lockstep.

If you work for me.. you never need to ‘interpret what I want’. Because I will make it very clear, while still leaving room for the person to come up with their own ideas and solutions.

It is not that I tell them exactly what the solution should be…. it is that I guide very clearly on what problem to solve and at what depth to solve it.

Wrapping up

I was having a conversation recently with a friend who has read my newsletter a few times, but said that he agrees with a few things but disagrees with others.

So I asked him how he manages his team.

And basically he does 1-1’s and verbally tells them what their priorities are for the coming week.

My reaction was… “I’d bet you could get 50-100% more out of them. Easily”

He of course thought i was exaggerating. But I wasn’t.

To me it’s just math… if you align in writing out all the tasks to do and then give constant feedback via comments to those tasks… you will ALWAYS just get a shitload more done.

I’ve seen it happen so many times… it’s just obvious at this point.