Why Do I Find It So Hard to Delegate? 7 Barriers and Solutions

Delegation is a critical skill for business growth, yet many entrepreneurs ask, “Why do I find it so hard to delegate?” The answer lies in psychological barriers, unclear processes, and misconceptions about outsourcing solutions. 

Delegation refers to the process of assigning someone else/s the responsibility to carry out certain functions or tasks. Although it may imply entrusting some authority as well (depending on the role).

If you are asking yourself, “Why do I find it so hard to delegate?”, there may be many answers or reasons to that, some closely related. 

Several psychological factors contribute to why some managers fear losing control. Perfectionism can cause managers to worry about tasks not being done exactly to their standards. Their locus of control—particularly an internal locus—might lead them to feel personally responsible for every outcome. 

Fear of failure makes delegation risky, as mistakes could negatively impact their perceived competence. Identity issues tie personal worth to professional achievements, making any misstep personally distressing. 

Trust concerns may create hesitance about handing over important tasks, and general anxiety amplifies uncertainty and discomfort around relinquishing control. Together, these factors strongly influence a manager’s reluctance to delegate.

In this guide, we’ll break down the root causes and provide delegation tips so you can delegate confidently—whether you’re working with internal teams, freelancers, or business service providers like Virtudesk.

Barrier 1: Fear of Losing Control 

Fear is paralyzing, particularly for those in decision-making positions. Many managers or leaders keep asking themselves, “Why do I find it so hard to delegate?” because they’re concerned that tasks won’t be completed to their exact specifications or that they might lose control of what is being done. 

They are afraid of losing control of the results or even the entire project. One fact that contributes to this fear is that the delegator still remains accountable for the results of the task they delegated. This can lead to burnout, stalled growth, and missed opportunities.

From a psychological standpoint, the fear of losing control often involves a mixture of identity, trust, perfectionism, and anxiety related to perceived failure. Managers frequently tie their self-worth and professional identity to their roles and achievements (Crocker & Park, 2004, The Costly Pursuit of Self-Esteem). Delegation may trigger anxieties that subordinates' mistakes reflect negatively on their own competence or reputation. 

Reluctance to delegate often stems from trust issues, such as concerns about subordinates' abilities or reliability (Mayer, R. C., Davis, J. H., & Schoorman, F. D. ,1995, An integrative model of organizational trust). 

Viewing this topic from another perspective, a monography published by the American Psychological Association (Rotter, J.B, 1966 Generalized expectancies for internal versus external control of reinforcement), Rotter introduces the concept of locus of control. This psychological concept refers to a person's belief on the extent to which they have control over the events in their life. Some believe their actions are a consequence of their choices and efforts, while others perceive any outcomes are a reflection of external factors, like destiny, luck, or others. 

Taking this to our topic of why people find it hard to delegate, individuals with a strong internal locus feel personally accountable for all outcomes and results and find it hard to let others take charge. 

How to Overcome It

1. Start Small: Delegate low-stakes tasks (e.g., scheduling meetings or a routine email campaign) to build trust incrementally.
2. Use Tools: Project management software (like Trello or Asana) helps you monitor progress from a distance. Slack or other communication apps enable quick updates without micromanaging.
3. Encourage Feedback: Create an open feedback loop so both you and the person or team you delegated to can share insights and improvements.

How Virtudesk Can Help You

At Virtudesk, we understand the importance of maintaining quality standards and know the importance for managers, leaders, or business owners to know how their teams are performing and find relief knowing everything is done correctly. All our professionals undergo thorough training to align with your brand guidelines. 

By delegating smaller administrative or repetitive tasks to Virtudesk first, you can ease into the delegation process without worrying about losing control. Over time, you’ll see how our consistent performance builds confidence and frees you to focus on business growth.

Additionally, we count on a unique monitoring tool that allows keeping track of each staff member’s performance, find gaps for improvement. Take a look at Timedly, our time-tracking software that helps business owners monitor and improve employees’ efficiency with a single click while facilitating collaboration and project tracking. 

Barrier 2: “No One Can Do It Like Me” & Perfectionism

This mindset often stems from pride in your work or a belief that only you understand the “right” approach. Many entrepreneurs fall into delegation challenges by assuming others lack the knowledge or skill to replicate their exact processes. Over time, this leads to overwork and stalls business growth because you become the only bottleneck.

You worry that tasks won’t meet your standards. This fear usually comes from a lack of trust in others’ abilities or processes. 

Also, past delegation failures can make it feel like a risky adventure the decision-maker won’t want to take. Tendencies toward perfectionism, characterized by excessively high standards and fears of imperfection (Stoeber, Joachim and Damian, Lavinia E. (2016) Perfectionism in employees: Work engagement, workaholism, and burnout) are high impediments towards delegation.

How to Overcome It

1. Invest in Training: Provide clear guidelines, checklists, and video tutorials for recurring tasks like report formatting or data entry.
2. Allow for Different Approaches: Focus on the end result rather than the specific method. If the outcome meets or exceeds your standards, different approaches can bring new perspectives.
3. Outsource Specialization: Tasks such as SEO, content creation, or advanced bookkeeping often require expert skill sets. Rely on specialized providers or professionals to elevate quality beyond what a single person can achieve.

How Virtudesk Can Help You

At Virtudesk, we can match you with virtual assistants or professionals in different areas who specialize in specific fields—like digital marketing, social media management, or lead generation. This ensures tasks are completed to a professional standard, and you’ll quickly see that delegating to an expert can outperform a single do-it-all approach. Visit our site, and you’ll see some of the services we provide and some of the industries we are collaborating with. Please note that our services and industries keep expanding, so if you don’t find yours listed, contact us. We’ll cover your needs! 

By delegating to Virtudesk’s specialized teams, you gain peace of mind and more time to invest in innovative projects.

Barrier 3: Time Constraints

Explaining tasks and training someone else can feel like it takes more time than just doing it yourself. However, this short-term view often leads to chronic overload, missed deadlines, and subpar results when you eventually hit a wall.

How to Overcome It

1. Create Templates: Develop workflows for repetitive tasks (e.g., social media calendars, email marketing sequences). This upfront effort pays off repeatedly.
2. Batch Training: Record training videos or create one-pager guides so you’re not explaining the same steps multiple times.
3. Find Outsourcing Solutions: Outsource recurring responsibilities, like data entry or customer support, to free up your schedule for critical decision-making and strategic planning.

How Virtudesk Can Help You

Virtudesk is here to make things easier for you. We carry out the recruiting, onboarding and training process and offer guidance on delegation best practices to our clients and their remote staff. We provide detailed documentation and ongoing support so you don’t need to spend time teaching and have more time for leading and revenue-generating activities. 

Barrier 4: Lack of Clarity

Not knowing what to expect is another strong barrier for those who find it hard to delegate. Unclear expectations lead to poor results, further fueling the notion that delegation “doesn’t work.” Even the most capable teams can flounder without a clear understanding of the task, goals, or standards.

How to Overcome It

1. Use SMART Goals: SMART goals are a widely used framework for determining clear and achievable objectives. SMART stands for

• Specific, 
• Measurable, 
• Achievable (or Attainable), 
• Relevant, and 
• Time-Bound objectives. 

Here are two simple examples of bad and good goal-setting:

• Bad: “Handle social media.”
• Good: “Post 3x weekly using brand guidelines, aiming for 10% engagement.”

If you want more detailed info about this framework, you can download the pdf  SMART Goals: A How-to Guide by The University of California.

2. Document Your Processes: Maintain a central knowledge base or standard operating procedure (SOP) that outlines each step in detail.
3. Regular Check-Ins: Have short but frequent meetings or updates to confirm alignment and catch misunderstandings early.

How Virtudesk Can Help You

As a serious business service provider, our process at Virtudesk starts with understanding your vision, brand guidelines, and delegation strategies. We help you refine your approach by setting clear milestones and measurable metrics. Through consistent communication and progress reports, we ensure the tasks you delegate to our teams fully align with your overall goals—reducing errors and clarifying expectations from day one.

Barrier 5: Distrust in Processes

A history of poor past experiences or inconsistent workflows can create deep-rooted skepticism. Leaders who’ve been burned by unreliable contractors or confused handovers often ask, “Why do I find it so hard to delegate again?”

How to Overcome It

1. Establish Accountability: Set a cadence for weekly check-ins, use performance metrics or KPIs to track progress, and maintain transparent reporting.
2. Optimize Workflows: Streamline processes by leveraging automation and standardized procedures to reduce human error.
3. Partner with Experts: When you collaborate with a reputable outsourcing firm, you gain from their established systems and proven results.

How Virtudesk Can Help

Virtudesk has a proven track record of delivering reliable support through trained and experienced professionals. Our virtual assistants, call center representatives, and professionals in other disciplines follow tested workflows that are adaptable to your unique business processes. We adjust based on your feedback, ensuring you always have visibility into each stage of the work. This approach helps rebuild trust and dispel doubts from past negative experiences.

Barrier 6: Fear of Higher Costs

Many leaders believe delegation automatically means inflated costs, especially if they’re considering external help. They assume hiring or outsourcing will stretch the budget beyond what their business can handle.

How to Overcome It

1. Compare Real Costs: Consider the opportunity cost of doing everything yourself. Losing hours on repetitive tasks can be far more expensive than outsourcing.
2. Budget Gradually: Start on a part-time or project basis so you only pay for what you need.
3. Track the Return on Investment (ROI): Monitor how delegation impacts productivity, revenue, and stress levels to see real returns.
4. Hire a Service Provider with Remote Staff: Many outsourcing companies have their staff located in regions where labor costs are lower, and that is reflected in the fees they charge for each worker. Taking a look at Virtudesk’s pricing page will give you clear proof of that. 

How Virtudesk Can Help You

At Virtudesk, we offer flexible plans that scale to your budget and workload. Instead of employing a full-time staff member for tasks that only require part-time attention, you pay only for the services you need. By demonstrating measurable ROI (Return on investment) like time saved and projects completed, our clients often find outsourcing is not just affordable but a catalyst for business growth.

Barrier 7: Inadequate Delegation Skills

Sometimes the biggest hurdle is the “how” of delegation. Many entrepreneurs have never learned a systematic approach to assigning tasks, setting deadlines, or providing the right level of guidance, leading them to wonder, “Why do I find it so hard to delegate effectively?”

How to Overcome It

1. Study Best Practices: Take online courses, read expert articles, or attend webinars focusing on how to delegate effectively.
2. Practice Gradually: Start by delegating smaller tasks and reflecting on what went well or what went wrong.
3. Use Feedback Loops: After each assignment, review both the process and outcome with the person you delegated to. This helps refine your methods.

How Virtudesk Can Help

Virtudesk’s process is designed to guide you through the delegation journey step by step. We offer an onboarding framework that clarifies how to communicate goals, define outcomes, and set check-in intervals. As you delegate to our virtual assistants, you’ll gain hands-on practice in directing tasks, evaluating results, and adjusting your approach for continuous improvement.

You might still have the question, “How do I find it so hard to delegate?” roaming around your brain, although we discussed the most common reasons. If so, maybe you also need to discover when it is time to delegate, why and how. Spending a few minutes reading our clarifying article linked above might be helpful. 

Choosing the Right Delegation Path

Not all delegation paths are equal. There are many different options when it comes to delegating or outsourcing tasks. 

Internal Teams vs. External Providers

• Internal Teams: Best for tasks needing daily oversight (e.g., HR). However, they may lack specialized skills like SEO or graphic design.
• External Providers: Ideal for specialized skills. Virtudesk’s IT support, for example, ensures 24/7 technical assistance without hiring full-time staff.

Freelancers vs. Outsourcing Companies

• Freelancers: Cost-effective for short-term projects (such as logo design). However, reliability can vary based on individual availability.
• Outsourcing Companies: Better for ongoing needs (e.g., bookkeeping). consistent quality, scalability, and teams that adapt to your workflow.

The Hidden Benefits of Delegation

Effective delegation isn’t just about saving time—it’s about business growth:

1. Focus on Strategy: Reallocate your energy to high-impact tasks like business development.
2. Team Empowerment: Delegation builds trust and skills within your internal team.
3. Scalability: Outsourcing partners like Virtudesk adapt to seasonal or project-based demands (e.g., holiday customer support), helping you flex resources up or down.

Conclusion: Delegate Smarter, Not Harder

Delegation is not a sign of weakness but a deliberate move to unlock growth. By addressing barriers like fear of control, perfectionism, time constraints, costs, and skill gaps, you can transform delegation challenges from a stressor into a superpower. Whether you choose internal teams, freelancers, or partners like Virtudesk, the key is to start small, clarify expectations, and trust the process.

Still wondering, “Why do I find it so hard to delegate?” Let us show you the way. Explore Virtudesk, the business service provider that offers a plethora of outsourcing solutions to streamline tasks and scale your business. From virtual assistants to SEO experts and team managers, we tailor our services to your unique needs. 

Delegate confidently today, and your future self will thank you. Call us at +(800) 470- 8136 or schedule a free discovery call, and you’ll soon find it easy to delegate and see your business or professional practice thrive.