The document discusses the evolving role of freelancers and their integration into organizations during digital transformation, emphasizing the importance of structured project management and engagement strategies. It highlights the need for clear project definitions, effective decision-making processes, and the proper use of non-disclosure agreements tailored to freelance work. The author encourages collaboration and reflection to enhance freelance outcomes and invites participation in a LinkedIn group focused on onboarding freelancers.

1. Sign-up for our LinkedIn Group
In life, the issue is not control, but dynamic connectedness - Erich Jantsch
http://OnBoardingFreelancers.com

2. Expanding Use of Freelancers
I believe the use of developers has enabled freelancers to expand both in roles and higher prices. During the digital
transformation period, freelancers have moved into other strategic areas of business. Freelancers in and out of IT assist
across the entire spectrum as depicted in the Cascade of Choices adapted from Playing to Win. These choices are associated
with a unique method of engagement which I think acts as a detriment to the full utilization of freelancers within an
organization. It creates a “special” circumstance for each and every instance, and poor management of the resource often
ensues. Alternatively have an outline, for example, use the Cascade of Choices to develop a standard based on roles. You
may want to have a freelance expert or go-to-source to clarify, accelerate and manage.
• Purpose
• Motivation
What is our
winning
aspiration?
• People
• Geo/Platforms
• Industries
Where will we
play?
• Business
Promise
• Uniquenes
s
How will we
win?
• Activities
• Competenc
ies
What
capabilities
are needed? • Structures
• Support
What
systems are
required?
Freelancers allow us:
• Have project-specific help
• Offer outside thinking and expertise
• Enable different use of platforms
• Different culture perspectives
• Increase the speed of getting things done
Cascade of Choices
Adapted from Playing to Win: How Strategy Really Works by
A.G. Lafley and Roger L. Martin

3. • Reflective Writing
• Reflective Interviewing
• Analytic Discourse
• Team Reflection
Finding Focus
• Collaborator Interviewing
• Collected Works Review
• Instructional Retrospective
• Visualize Success
Refining
Focus
• Achievement Targets
• Performance Ratings/Scales
• Long Term Goals
• Rate of Growth
Assessment
Adapted from The Action Research Guidebook 3rd Edition 2017 by Richard Sagor & Charlene Williams
Finding Your Focus
Target Identification
(Process, People, Product, Platform)
We have all heard sayings like this before, “Most of the mistakes in
thinking are inadequacies of perception rather than mistakes of
logic.” —Edward de Bono. Projects that have an extended life need
a little more substance than simply target identification. We are often
in a hurry to get to the doing stage. I would challenge you to think of
the Focusing stage as an integral part of doing.
This should not be done in
isolation, and this outline provides
an immediate opportunity to take
the reflective process into a
collaborative process.
I have found Richard
Sagor’s method concise for
developing a well-structured
focus. Remember, that this is not
only for ourselves but for others,
and often needed for project
funding.
As Sagor sums it up;
Why is Having a Clear Vision So Necessary? Opportunities rarely exist for going back and giving things a second try. This very
real risk of losing our direction and thereby failing to reach our desired destination should motivate us to be disciplined and
deliberative when planning our action research—that is, our planned exploration of a not-yet-visited destination.

4. How do you think through hiring a Freelancer?
Do you have a plan to empower the
outcome? To fully utilize their capabilities?
This A3 is focused on empowering the
freelancer within your organization. This is
the pre-planning stage before hiring.
However, I think it is a dynamic document
that can be used in other ways as the
engagement continues.
The levers and three steps of change are
adapted from the book, The Five Levers to
Improve Learning by Frontier and
Rickabaugh.
Heifetz and Linsky, in the book Leadership on
the Line, state that "the single most common
source of leadership failure is that people
treat adaptive challenges like technical
problems."
I think this happens to a freelancer that we sort of cross over these boundaries and projects tend to drift or become less
productive. Often, there is a misconception of the magnitude of the challenge which results in solutions that require a different
type of change than proposed such as a transformational change versus a transactional change. Or, the flip side may offer a
transformational versus the needed transactional which can over-complicate the offering or create non-competitive pricing.

5. Scope
Determined by Stakeholders
Set Guidelines: Learn thru
Experiments & Feedback
Measure of Success
Within Scope, Time, Budget Customer Satisfaction & Value
Customer Feedback
At the End Continuous
Mentality
Build-once Test and Learn
Mindset
Project Product
Are You Hiring Freelancers for Project or Product Work?
Adapted from Figure 6.1 in the book
Edge: Value-Driven Digital Transformation by Highsmith, Luu & Robinson
If there is one area that I find that blurs in Freelance
work it is the conception of Product vs Project. The
basic definition of a project is that it has a beginning
and an end whereas products deliver repeated value
to a customer.
As I was reviewing Highsmith, Luu and Robinson's
new book the Edge this table jumped off the page at
me as to where many times it becomes confused. It is
not simply the definition and the actions of people
hiring freelancers but myself as a freelancer where I
left project scope to drift.
I have struggled in the past as many Freelance
engagements sort of cross-pollinated between the
columns. One of my ideas that I have tried is to be
more Scrum-like in iterations and keep projects as
projects - time-based. Also when projects appear in
Product style job to break it out as a project. This may
seem like Project/Product Management 101 but as
the Freelancer, it is not quite that easy as the new kid
on the block to make it happen.

6. Conditions for Consensus Decision Making
Guidelines
1. Unity of Purpose
2. Equal access to power
3. Autonomy of the group
4. Time
5. Attending to process
6. Attending to attitudes
7. Willingness to learn and practice
As a Freelancer, will you recognize how the group will reach a consensus? Most groups work with the idea of sufficient
consensus which does not mean more than 50% rather 80% of the group is willing to commit and act. Some efforts will
even fall into the "no-decision" category.
Is the appropriate action being created for you to achieve clarity around the decision-making process? Are the needed
conditions enabled?
Adapted from the book The Adaptive School
Conditions for CDM is from the work of The Center for Conflict Resolution

7. Project Management System
Agile, Scrum, Waterfall, Kanban, Other
The one that has influenced me the most
on Agile Project Management is Jim
Highsmith’s book of the same name. In
this book, Jim demonstrates what iterative
project management is all about.
I especially like the terminology he uses
moving from Plan-do, which just about
always results in a linear, waterfall
approach and the more traditional names
of Initiate, Plan, Define, Design-Build, and
Test.
What type of Project Management System do you use with a Freelancer?
Instead, he uses Envision, Speculate, Explore, Adapt, and Close (ESEAC). Highsmith uses Envision to form the structure or
better yet the skeleton for the project and then the Speculate-Explore-Act (S-E-A) as an overall cycle with Explore-Act being
smaller iterations within SEA until the project is Closed. You will have multiple iterations using E-A within S-E-A, and your
larger iteration of S-E-A may even be adjusted as we learn more through the project. I will also add that individual E-A may
close at different times and that you could even have separate S-E-A path in larger projects.

8. I typically introduce and suggest Trello utilizing a version of the Highsmith A3, (LinkedIn
Article: https://lnkd.in/ehMuXbn). This enables me to get started quickly, encapsulating
and documenting the entire project (Projects have a beginning and end). I stay out of
communication platforms such as Slack, Email and other messaging services. More
importantly, all the material and messaging gathered can be owned by the Project owner.
Multiple projects can easily be added through another board. Different Epic (Speculate)
Stories can be added to the same by using label colors.
Book: Agile Project Management by Jim Highsmith
Many times a Freelancer gets hired, the person/organization doing the hiring does not have a good project
management system in place. The failure of the Project and Freelancer is just simply the result of a poor plan.
Please feel free to copy board: https://trello.com/b/1bO6SgQx/project-board-highsmith

9. Non-Disclosure Agreements for Freelancers
(Non-Compete – Let’s not be silly and even have a conversation.)
My Guidelines:
1. Not the same as an employee
2. Not scraped from the web
3. Only includes what is applicable
• Limited to scope of project
• Review the Job Description
• Review the 6 Levers
4. Length - Double the time of Project
(Maximum 1-year)
5. Initial Trial period
6. Review what Freelancer brings to the table
7. Startups- If you have not achieved
product/market fit – don’t include it.
This is not legal advice – Go see an Attorney
There is probably not one thing that has prevented me more from
getting hired than my refusal to sign an NDA. Half of them are
created for a full-time employee and the other half have been
scraped from the web and altered to make them more one-sided.
If you can't afford to have one professionally done, how do you
expect to enforce one?
An NDA for a freelancer needs to be limited in scope not
expanded. My preplanning outline is a great starting point for
reviewing your present NDA. Looking at the levers and type of
change the project requires can often eliminate the need for an
NDA.
A couple of points that I would emphasize is that if one would be
required to make it known at the beginning, even in the job
description. I would encourage a short trial period to determine
that both parties want to continue working together before
signing. A poor NDA discourages many "good" freelancers from
accepting the position.

10. In life, the issue is not control, but dynamic connectedness - Erich Jantsch
http://OnBoardingFreelancers.com
These are the types of conversations I would like to have in the group. Please consider joining the LinkedIn Group if
you feel like you can contribute or would just like to learn from the conversation.
LinkedIn Group: OnBoarding Freelancers