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Leadership


UNDERSTANDING AND OVERCOMING THE CHALLENGES OF MANAGING INDEPENDENT CONTRACTORS 

by Tosho Trajanov

14 min read



The global workforce is experiencing a pivotal shift. A McKinsey survey reveals
that 36% or 58 million Americans now work independently. This trend isn't
confined to the U.S. The tech industry, in particular, is leaning into
contractual hires.

In January 2021, only 6% of tech job listings were for contract roles. By
October 2022, contract-based tech listings surged by almost 20%. Additionally,
many engineers affected by the 2022 and 2023 tech layoffs opted for independent
contracting, capitalizing on its flexibility and emerging opportunities.

However, while this trend continues to grow, many businesses harbor reservations
about hiring independent contractors. These doubts range from quality assurance
to compliance and communication challenges. 

In this article, we'll explore the most pressing concerns companies face when
considering collaborating with independent contractors. More importantly, we'll
offer tangible solutions to these challenges to help businesses capitalize on
the benefits of this emerging workforce. 


TABLE OF CONTENTS

 * Cultural Differences
 * Ensuring Operational Excellence 
 * Compliance Challenges 
 * Communication Barriers 
 * Engagement and Motivation Challenges 
 * Risk Management 
 * Conclusion


CULTURAL DIFFERENCES

Managing a team with contractors from different cultural backgrounds can be a
bit tricky for some managers. Being on time is one area where misunderstandings
can happen. Some managers might think being late is unprofessional. However, in
some cultures, people might not be as strict about exact times and would place
greater importance on doing things right and maintaining harmony rather than
getting something done just for the sake of meeting a deadline.

How people make decisions can also be different. A manager might be used to
making choices based on lots of data and planning. In contrast, some contractors
might be more flexible, using the information they have on hand and what feels
right at the moment.

Cultural differences can influence perceptions of continuous improvement. While
some cultures might view feedback as a tool for growth, others might see it as
criticism. This can make implementing continuous improvement strategies more
challenging.

Lastly, holidays and celebrations are important to consider. Different cultures
have their own special days and ways of celebrating.


ADDRESSING CULTURAL CHALLENGES 

Here are some solutions to effectively navigate cultural nuances in a global
workforce. By adopting these strategies, tech leaders can fully embrace and
foster cultural diversity, transforming it into a powerful catalyst for
creativity, innovation, and enhanced quality in their projects and products.

   
 * Research and training: Research the cultural norms and expectations around
   punctuality and communication in the cultures you are interacting with.
   Investing time in learning these differences fosters respect, reduces
   misunderstandings, and improves overall team dynamics.
   
   
 * Collaborative decision-making: When possible, make decisions collaboratively.
   This ensures that everyone's viewpoint, shaped by their unique cultural
   background, is considered.
   
   
 * Respect for holidays: Be aware of and respect the significant holidays of the
   contractor's culture. This might mean adjusting deadlines or being
   understanding if they're unavailable during those times.
   
   
 * Communicate clearly: Communicate your expectations around punctuality
   clearly, and make sure to confirm your understanding of the other party's
   expectations. Be specific about the duration and due dates of projects or
   deliverables, and ensure that everyone is on the same page.
   
   
 * Learn basic etiquette: Familiarize yourself with basic greetings or phrases,
   or cultural practices, even if it's just a nod to the contractor's culture.
   This shows respect and can help build rapport.
   


ENSURING OPERATIONAL EXCELLENCE 

With a team of independent contractors spanning various geographies, maintaining
uniformity in quality and building trust can be a challenge. 

Given their independent status, contractors might have developed their own way
of working, which may not align with the company's established processes. This
can lead to inconsistency in output quality, making it harder for teams to
predict and manage results.

There might be gaps in how knowledge is transferred and documented. When
independent contractors complete their contracts, they might depart with
valuable expertise that hasn't been ingrained into the organization.

There's also the challenge of using specific tools and software. Independent
contractors might be accustomed to using different tools or software.
Integrating or adapting to a company's preferred tools can lead to productivity
slowdowns or data silos.

Attitudes toward quality control can also vary. What one culture sees as "good
enough," another might see as requiring refinement. This can lead to
inconsistencies in deliverables.

Beyond this, aligning contractors to the company's goals is crucial. Without
proper alignment, the team might pursue objectives that deviate from the broader
company vision, which can affect overall productivity and coherence.


UPHOLDING OPERATIONAL STANDARDS 

Managers can adopt the following solutions to maintain and enhance operational
excellence:

   
 * Standardize tools and processes: Provide contractors with access to the
   company's preferred tools. Offering training sessions on these platforms will
   smooth out the transition and ensure everyone is on the same page.
   
   
 * Document knowledge: Encourage, or even mandate, contractors to document their
   processes, insights, and critical information. Tools like internal wikis or
   shared document platforms can help in capturing and retaining knowledge.
   
   
 * Give everyone a voice: Make sure everyone is given a voice when technical
   issues are being discussed. If there's an issue on the team and you're in a
   meeting, give the independent contractors the time to talk about it. If they
   come to you with a problem they've found, empower them to fix it. Give them
   dedicated time and space in their schedule to experiment, build out Proof of
   Concepts on things, as this is the best way for senior contractors to
   understand the problem and better respond to it. 
   
   
 * Support team discussions: Team alignment can be a major problem. So, to avoid
   technical disagreements, try to align things ahead of time. Have a discussion
   beforehand. Have senior engineers from the team speak about the problems
   they're identifying and champion what they think is the right technical
   direction to drive consensus and build trust with their peers. 
   
   
 * Ensure team goals align with company goals: Avoid falling into the "tunnel
   vision" trap, where immediate team-specific deliverables overshadow broader
   company objectives. It's essential to balance and align immediate team goals
   with the overarching directives of the company. For instance, while a
   platform team might focus on specific group needs, it should also consider
   what's most beneficial for the entire organization. By promoting expansive
   thinking and fostering robust communication across all levels, teams can
   ensure they are not only meeting their immediate objectives but also
   contributing meaningfully to the business's overarching success.
   


COMPLIANCE CHALLENGES 

As companies collaborate with contractors from various regions, they are
introduced to a myriad of distinct labor regulations, each carrying its own
nuances. 

The intricacies don't end there; tax systems can vary greatly from one region to
another, demanding meticulous attention to ensure adherence. Additionally,
standards and expectations around confidentiality may differ. It's essential for
companies to ensure their contracts are tailored to respect local regulations
and, at the same time, safeguard their intellectual assets and proprietary
information.


TACKLING COMPLIANCE ISSUES 

To effectively deal with these complexities:

   
 * Stay informed: Regularly review and stay updated with international labor
   laws and tax regulations. This can be done by subscribing to legal updates or
   partnering with legal professionals specializing in international labor
   relations.
   
   
 * Customize contracts: Create tailored contracts for each region or country
   where the independent contractors are based. This ensures that the terms are
   aligned with local regulations, which reduces potential legal risks.
   
   
 * Consistent confidentiality clauses: While regulations may vary, maintaining a
   standardized confidentiality clause across all contracts is crucial. This
   protects company information while ensuring that contractors understand their
   responsibility in maintaining secrecy.
   
   
 * Engage local experts: Consult with local legal and tax experts before
   onboarding contractors from a new region. Their insights can help
   preemptively address potential compliance challenges.
   
   
 * Leverage platforms like Adeva: Adeva handles all the intricacies, from
   billing and payments to compliance and NDAs. By partnering with Adeva, your
   business can be assured of a smooth process so that you can focus on
   innovation and growth instead of administrative overheads.
   


COMMUNICATION BARRIERS 

There are many communication challenges that might arise when working with
independent contractors. Time zone differences can impede smooth scheduling, and
cultural nuances might sometimes lead to misunderstandings. 

An over-reliance on written communication can be problematic, especially in tech
roles, where a quick verbal discussion or screen-sharing session can sort out
complex issues more efficiently than extensive email threads. The absence of
non-verbal cues in these written exchanges can lead to further confusion.

Occasionally, teams might face discrepancies in technical jargon and standards.
A term familiar to one member might be completely foreign to another, which can
lead to potential misalignments in work.

On top of these, technical glitches, such as unstable internet connections, can
disrupt the flow of dialogue. The use of multiple communication platforms can
scatter conversations, making it hard to track discussions. In this digital
environment, there's also a lurking risk of burnout from over-communication as
teams strive to keep everyone updated.

The lack of face-to-face interactions can further compound feelings of
detachment. Also, the inherent asynchronous nature of remote collaborations can
cause delays in feedback. To steer clear of these pitfalls, managers must be
adept at accommodating the diverse communication styles and preferences of their
team members.


IMPROVING COMMUNICATION 

Here are a few ways to improve communication:

   
 * Flexible scheduling: With team members potentially spread across different
   time zones, it's essential to be considerate of everyone's hours. Using
   scheduling tools that display multiple time zones or tools that find mutual
   availabilities can be a lifesaver. This ensures that no team member is
   consistently burdened with meetings outside their regular working hours.
   
   
 * Promote team building: Just because a team is remote doesn't mean they can't
   have fun and get to know each other outside of work tasks. Engaging in online
   team-building activities, such as virtual games, shared movie nights, or
   collaborative projects, can help in building rapport and a sense of
   camaraderie among team members.
   
   
 * Embrace visual aids: Utilize diagrams, flowcharts, and shared boards like
   Lucidchart or Miro to visually communicate complex topics. We've put together
   a list of the best tools for running engineering teams, so make sure to take
   a look and equip your team with the resources they need to thrive.
   
   
 * Encourage 'no meeting' blocks: Schedule blocks of time where no meetings are
   allowed to let your team focus on work without the risk of burnout from
   over-communication.
   
   
 * Provide technical support: Ensure that all team members have access to stable
   internet connections and the required software. If possible, provide
   allowances for independent contractors to upgrade their setups.
   
   
 * Regular check-ins: Given the challenges of remote work, it's essential to be
   deliberate in setting up interactions. Regularly scheduled chats can provide
   a platform for insights, addressing concerns, and broadening perspectives.
   Through conversations, allow independent contractors to verify their
   understanding of issues. What they see as big challenges might be small, and
   what seems minor to them could be major.
   


ENGAGEMENT AND MOTIVATION CHALLENGES 

When it comes to the management and motivation of independent contractors,
unique challenges arise. The very nature of their roles, which might involve
irregular schedules, remote work, or task-specific contracts, can pose barriers
to their full engagement in company culture and operations.

For example, independent contractors often miss out on daily face-to-face
interactions that full-time employees experience. This absence can lead to
feelings of isolation, as they may not be present for impromptu meetings, casual
coffee breaks, or informal brainstorming sessions.

Independent contractors might feel they are viewed as outsiders, working on a
per-project basis rather than being ingrained in the company's fabric. This
feeling can deter them from voicing opinions or offering feedback.

Independent contractors may perceive limited opportunities for career
advancement within a company, as they might not be privy to internal promotions
or role transitions.

Full-time employees often have structured reward systems, including bonuses,
promotions, or recognition events. Independent contractors, on the other hand,
might not have access to these perks, which can dampen their motivation.


ENSURING SUCCESSFUL ENGAGEMENT 

Ensure successful engagement by following these best practices:

   
 * Inclusive communication: Keep contractors informed with company
   communications, newsletters, updates, and role-relevant changes. Making sure
   they're in the loop promotes a sense of belonging and ensures they're updated
   on any crucial company news or shifts.
   
   
 * Cultural immersion: Invite contractors to company events and activities;
   share company vision, mission, and values. When contractors understand and
   feel a part of the company's broader goals, they're more likely to align
   their work effectively and take pride in their contributions.
   
   
 * Professional development opportunities: Offer training, workshops, and
   avenues for more responsibilities. Investing in their growth not only
   improves their skill set but also shows them that the company values their
   long-term development.
   
   
 * Provide regular feedback and recognition: Regular feedback and recognition
   play a pivotal role in maintaining team morale and motivation. It's often
   underestimated how much of an impact recognizing and valuing a team member's
   contributions can have on their drive. This is particularly true for
   contributions that may seem minor on the surface but, in reality, can
   significantly influence the broader team or organization. By highlighting
   these achievements to contractors, managers can substantially elevate their
   spirit.
   
   
 * Shield contractors from organizational dysfunction: Shielding contractors
   from organizational dysfunctions is paramount for their productivity and
   motivation. This involves ensuring contractors have dedicated time to focus
   on technical tasks without constant disruptions. While it's essential to
   involve them in crucial meetings where their insights are invaluable, it's
   equally vital to avoid overburdening them with meetings that stray from their
   main responsibilities. As managers, the role also entails shielding the team
   from unnecessary organizational stress. Reducing these pressures helps boost
   their motivation and productivity.
   
   
 * Promote work-life balance and encourage external interests: Promoting a
   work-life balance and nurturing external interests are essential components
   of a well-rounded employee experience. It's crucial to understand that
   relentless work without intermissions can diminish both productivity and
   passion. Encouraging employees to explore diverse interests outside of their
   professional realm not only provides them with a refreshing break but also
   revitalizes their mind and body.
   


RISK MANAGEMENT 

When working with independent contractors, several challenges can emerge. One
frequent hurdle is creating clear contracts. Without these, confusion about
roles, outcomes, and pay can occur, leading to potential disagreements or even
legal issues. Intellectual property is another area of concern; unclear
contracts can create uncertainty about who owns the work, especially in tech and
creative fields. 

Confidentiality is essential, as contractors often collaborate with multiple
clients, which increases the risk of unintentionally sharing a company's
confidential data. Consistency in work quality might be hard to maintain with
independent contractors, which requires extra attention. Data security is
paramount; if contractors access company data from less secure environments, it
may jeopardize data integrity. Also, relying too heavily on a few contractors
can be risky if they suddenly can't work. Insurance coverage becomes vital,
especially if a contractor's actions lead to financial or other types of losses.


MITIGATING RISKS 

Addressing the challenges with independent contractors requires proactive
measures. Here are some solutions:

   
 * Robust contracts: Collaborate with legal counsel to draft comprehensive
   contracts. Ensure they detail responsibilities, deliverables, timelines, and
   compensation to prevent any ambiguities.
   
   
 * Intellectual property clauses: Clearly define in the contract who retains the
   rights to the work produced. Especially in tech and creative roles, stipulate
   the ownership of designs, codes, content, and other outputs.
   
   
 * Confidentiality agreements: Have contractors sign non-disclosure agreements
   (NDAs) that specify what information they can't share. This protects
   sensitive company information and sets clear boundaries.
   
   
 * Quality assurance protocols: Implement a standardized review and feedback
   process to ensure consistent quality from all contractors. This can include
   periodic check-ins, peer reviews, or dedicated QA sessions.
   
   
 * Data security protocols: Offer independent contractors secure platforms or
   virtual private networks (VPNs) for accessing and transferring company data.
   Regularly update and train them on best cybersecurity practices.
   
   
 * Secure partner: Partnering with a company that understands the intricacies of
   hiring and managing contractors can be a game-changer. Adeva, for instance,
   offers more than just a talent pool. They ensure that businesses can tap into
   top-tier tech talent while also handling various logistical aspects like
   compliance, billing, and communication, making the entire process streamlined
   and risk-averse.
   

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CONCLUSION

Effectively managing independent contractors has never been more crucial. As the
workforce evolves, tech leaders find themselves at the forefront of a
transformative shift in how work gets done. Embracing this change not only means
understanding the challenges but also crafting innovative solutions. 

By adopting the right strategies and partnering with trusted entities,
businesses can harness the full potential of the independent contractor model.
As we navigate this ever-changing landscape, the ability to adapt and innovate
will define the companies that thrive in the future. Tech leaders, it's time to
lean into this change and shape the future of work with confidence and
foresight.


FAQS

Q: WHAT IS A CONTRACTOR IN TECH?

A contractor in tech is a professional hired for a specific project or a defined
period, rather than as a permanent employee. They provide specialized technical
expertise, often working remotely, and operate under a contract that outlines
deliverables, timelines, and payment terms, without the typical benefits given
to full-time employees.

Q: WHY DO TECH COMPANIES HIRE SO MANY CONTRACTORS?

Tech companies hire contractors for flexibility, cost-effectiveness, and access
to specialized skills on-demand. Contractors allow companies to quickly scale
teams, manage project-specific needs, and mitigate long-term employment
commitments, especially in the ever-evolving tech landscape where rapid
adaptation is crucial.

Q: WHAT ARE THE CHALLENGES OF INDEPENDENT CONTRACT WORK?

Some of the challenges businesses face when working with independent contractors
include ensuring quality, navigating diverse labor laws, managing communication
barriers, fostering engagement, and maintaining operational consistency across
different contractors.

TOSHO TRAJANOV

Co-founder

Tosho is a co-founder at Adeva, with over a decade of experience in the tech
industry. He has partnered with diverse organizations, from nimble startups to
Fortune 500 companies, to drive technological advancements and champion the
effectiveness of cross-cultural, distributed teams.

Expertise
 * Leadership
 * Planning
 * Product Strategy
 * Software Architecture
 * Agile Methodologies
 * AWS
 * Microservices
 * PHP
 * PHP 5
 * +4




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