Freelancers: you hold the keys to management of the future. As we transition from Scientific Management to agile workflows, your ability to horizontally collaborate with decision makers will be a key differentiator. BUT…you must understand how to manage with decision makers.
Dear Freelancers,
The future is yours to lose.
While institutional structures focus on producing robots, your trailblazing a new form of management. One that’s agile. One that’s lean. One that cuts through the post traumatic stress disorder of Taylor’s Scientific Management and into the possibilities of digital transformation.
For the past 150 years, we’ve been trained to do three things:
- follow a checklist with little to no deviation
- specialize in this checklist
- mitigate risk
Today this mindset is an endangered species. Instead, thanks to the ubiquity of digital transformation, the new mindset means making your own checklist with constant deviation, being a resourceful generalist, and mitigating risk by diving into the unknown.
BUT — just as going to the gym doesn’t mean you’ll look like Channing Tatum — being a freelancer doesn’t automatically mean you’ll master this mindset. It sets the stage. But it doesn’t cross the chasm. I could send you HBR articles galore. Or I could put you to sleep with my book list.
Instead, let me tell you why decision makers cut ties with freelancers.
Quality can be great. A portfolio can be spectacular. You can even have above average ratings & reviews. But consistently I see one fatal flaw — working with decision makers.
Let me tell you why……
As we transition into agile workflows, freelancers hold the keys to management of the future. BUT — you must understand how to work alongside decision makers.
The Pulse of an Executive…
Freelancing from a young age taught me one vital lesson. Executives, i.e., decision makers, are ordinary people, with one exception.
In theory, they look like this:
In reality they look this:
Either way, they are extremely, extremely busy. And depending on the person — very stressed.
I know — we are all busy. But decision makers cannot blame bad management because they are the management. And thanks to our environment of accelerated creative destruction, they require a deviation from traditional management theory.
The prerequisites to being a successful freelancer still hold true: making your own checklist with constant deviation, being a resourceful generalist, and mitigating risk by diving into the unknown.
But to realize your value, you must take it a step further and match your value with how you deliver it. It’s not enough to be smart. Below, we discuss some proven tactics that you need to apply to engagements.
Decision makers are beyond busy, stressed, and require a deviation from traditional management theory. On top of your prerequisites, there are tried and true tactics to deliver value that you need to implement today.
Why Should I Care?
Who cares that decision makers need the white-glove treatment? Don’t they sound a little like spoiled brats? Shouldn’t they be able to control their own engagements?
Let’s dig deeper.
Under traditional management, 10 years ago your value was obedience.
How well could you listen and follow orders? There was no collaboration, rather subordination.
Today, the default is dynamic subordination, a horizontal organization of teamwork. Spurred by the rise of agile in powering digital transformation, dynamic subordination outlaws expertise or the HIPPO (highest paid person in the room) in favor of whoever takes action. This means that as a freelancer you are expected to be the expert.
The book Stealing Fire does a great job of showing how a traditionally conservative/hierarchical organization, the Navy Seals, takes advantage of this. According to Commander Rich Davis, dynamic subordination follows these rules:
- “Slow is dangerous. We want to move as fast as possible. To do this, there are only two rules. The first is to do the exact opposite of what the guy in front of you is doing–so if he looks left, then you look right. The second is trickier: the person who knows what to do next is the leader. We’re entirely non-hierarchical in that way. But in a combat environment, when split-seconds make all the difference, there’s no time for second-guessing. When someone steps up to become the new leader, everyone, immediately, automatically, moves with him. It’s the only way we win.”
Think you’re immune if you are not a freelancer?
Think again. The future is hybrid (freelance and full-time employment), and as digital transformation necessitates an agile workforce, dynamic subordination will increasingly become the default in every workplace.
This delivery method of value isn’t unique to freelancing. It’s the new normal as we shift from hierarchy to dynamic subordination — horizontal collaboration that puts action over expertise
How to Conquer Dynamic Subordination
Managing decision makers is a mix of art and science. Obviously, it is case dependent, but here are four steps you can implement today:
Step 1: Own the Engagement
In my article Freelancers: How Scoping Will Make You Stand Out, I revealed that most of the time I don’t know what I am hiring you for. I have a pain. I have an insight into a solution. But I am not the expert. You are the expert, and I expect prescriptive guidance from you.
This comes out in the form of good questions and clear communication of what has to be accomplished, who will do it, and when it will get done.
Two quick hacks:
- Demonstrate scope — If it’s a project lasting more than a week with multiple milestones, show me a scope document. Download my scoping template.
- Continuously update progress — I use Trello and Planner for project management. Both are highly visual project management software that allow me to see quickly, and on one screen, the status of my projects. If you want to go over and above, keep a clean planner board for me, continuously updating your progress. It is not a good thing if I have to ask for an update.
Step 2: Less is More
Whether reading or listening, 9 times out of 10, I’m scanning for the important insights and ignoring the rest.
I promise that I’m not ignoring or discrediting your work but merely seeking the salient points.
Three quick hacks:
- The Pyramid Principle — Lead with the answer first, followed by the essential supporting facts of why that is the answer.
- The two-minute rule — Strive to keep every answer under two minutes.
- Visuals: Provide visuals whenever & wherever possible. For example, rather than explaining your idea, show me a mockup, or even better — comparables.
Step 3: Please, Please, Please, Questions all at once
I know….this sounds very specific. But it’s an immediate DQ if you asks questions sporadically. For example, a question at 10 am. A question at 1 pm. A question at 3 pm. Especially if it’s a weekend.
Time is our greatest asset. From the second I wake up to the time my head hits the pillow, I’m calculating my time by the second and plotting which windows of time I can hit flow. Regarding questions, this means I pick one time to hammer them all out.
So please ask questions accordingly :)
Step 4: Strict Adherence to Deadline
According to Reid Hoffman “If you are not embarrassed by the first version of your product, you’ve launched too late.”
With milestones, I don’t want you to be embarrassed, but it is imperative I see something on the deadline. Generally a decision maker doesn’t manage in a vacuum. They are communicating with their boss. Their bosses boss. And while you think something embarrassing makes you look bad, missing a deadline makes the decision maker look bad.
Summary
The future is you. You are the expert in managing virtual agile workflows. In working horizontally through dynamic subordination. Or so you think…
One key to dynamic subordination is managing decision makers, and 4 steps you can implement today are:
- Step 1: Own the engagement
- Step 2: Less is more
- Step 3: Send me all questions at once
- Step 4: Don’t miss the deadline
For the original article and more: https://venturel.io/blog/freelancers-lets-talk-project-management/
Author: Matthew R. Mottola
About the Author
Matthew R. Mottola builds the Future of Work. At Microsoft, Matthew leads go-to-market and drives a number of key initiatives, including but not limited to, user experience for internal adoption & engagement of on-demand/freelance platforms. At Georgia Tech, he guest lectures and helps develop their entrepreneurship curriculum. At Universities, he speaks and advises on how they can prepare for this future. With early stage ventures, he advises on & invests in this future. He is the author of university-level textbook StartUp not StartDown and upcoming book The Human Cloud.
