How can you effectively delegate tasks and build a strong team as your business grows? We asked industry experts to share the advice they’d give to entrepreneurs who struggle with delegation. Here are their strategies for categorizing, communicating, and automating tasks to empower your team and enhance productivity.
- Categorize Tasks by Value
- Align Assignments with Strengths
- Start with Self-Awareness
- Hire the Right People
- Create Detailed Process Documentation
- Establish Clear Communication Channels
- Create Clear SOPs and Assign Ownership
- Start with Small, Low-Risk Tasks
- Hire Before You Are Ready
- Provide Clarity and Context
- Document Failures to Identify Patterns
- Foster a Culture Rooted in Core Values
- Teach One Thing at a Time
- Share the Big Picture
- Implement a Mentorship Program
- Leverage Automation Before Delegation
- Focus on Hiring Self-Accountable Builders
17 Delegation Strategies for Entrepreneurs
Categorize Tasks by Value
I was taught early on in my journey as a business owner to categorize my numerous tasks into 3 separate groups: $10 tasks, $100 tasks, and $1000 tasks.
The tasks I would pay someone $10 to complete are tasks to consider eliminating (because their value is so minimal) or explore a way to automate those tasks as they likely do not require a human touch. For example, categorizing expenses can often be completed automatically using bookkeeping software.
The tasks I would pay someone $100 to complete are important, yet are likely the things I could do but do not enjoy doing. These are ripe for delegation, as there is likely a team member or outside resource who loves these tasks and can complete them more efficiently and effectively. These are the tasks that do not require my unique strengths or maximize my zone of genius.
If I outsource enough of the $10 and $100 tasks, this leaves me the capacity to do the work I am most passionate about—the $1000 tasks for which I get paid the highest amount. This is the work that can uniquely be completed by only me as the business owner/leader.
I continuously evaluate my “to do” list through the lens of the $10/$100/$1000 approach, to ensure I am leaning into the strengths of my team through delegation and investing my time in the unique deliverables that set my organization apart, which significantly contribute to the growth of the business.
Elisabeth Galperin
Executive Coach | Business Productivity Consultant, Peak Productivity
Align Assignments with Strengths
One of the most effective strategies I have found for delegating tasks and building a strong team is to align assignments with each team member’s unique strengths and passions. Delegation is not just about offloading tasks; it is about empowering your team to take ownership of outcomes. I recommend entrepreneurs invest time in truly understanding their team’s skills and aspirations, then delegating tasks that challenge them and allow them to grow.
For those who struggle with delegation, start small—delegate one task you feel slightly uncomfortable letting go of and trust the process. Remember, your role as a leader is to focus on vision and strategy, not every operational detail. Delegation is a muscle—the more you practice it, the stronger both you and your team will become.
Allison Dunn
CEO, Head Business & Executive Coach, Deliberate Directions
Start with Self-Awareness
One strategy I’ve found incredibly effective for delegating tasks and building a strong team is starting with self-awareness. Take time to understand your strengths, growth areas, what you enjoy, and what you don’t. Delegate your weaknesses first—this allows you to focus on areas where you’re most valuable. Then, hand off tasks you dislike to free up mental energy.
As your business scales, empower others to take over areas you excel in by mentoring them, and shift your focus to what you truly love doing. Tools like the Eisenhower Matrix are invaluable for prioritizing tasks into four quadrants, helping you decide what to do, delegate, or eliminate. For entrepreneurs struggling with delegation, my advice is this: trust your team, start small, and remember that delegation isn’t about losing control—it’s about amplifying your impact.
Adriana Cowdin
CEO and Executive Coach, Be Bold Executive Coaching
Hire the Right People
The thing that I learned about delegation is that delegation has nothing to do with creating systems, processes, and all that jazz. Delegation is about having the right people. When I started my business, I realized that if you hire people that take initiative and are committed to their work, you end up delegating naturally.
Let’s think about this for a second, if you hired a truly competent person who cares about their work and wants to make a difference, wouldn’t they want to take more work off your shoulders? Wouldn’t they naturally want to be delegated to?
So my answer to entrepreneurs who have a tough time delegating is that they actually have a tough time hiring the right people. Because when you hire the right people, you simply feel more comfortable giving them work. Good people don’t need to be micromanaged.
Sharon Koifman
Founder and Remote President at Distantjob, DistantJob
Create Detailed Process Documentation
The most effective delegation strategy I discovered was creating detailed process documentation coupled with a structured training program. When scaling my company, I initially struggled with letting go of tasks, trying to maintain control over every aspect of our link building operations. This changed when I developed a comprehensive playbook that broke down complex processes into step-by-step guides, complete with video tutorials and examples.
This approach allowed me to successfully train over 100 team members across five continents while maintaining consistent quality in our service delivery. For entrepreneurs struggling with delegation, here’s what worked best for me:
- Start with documenting your processes in detail, including screenshots and video recordings—this creates a replicable system.
- Implement a “shadowing period” where new team members observe how you handle tasks before taking them on.
- Create checkpoints for quality control without micromanaging. I use a weekly scorecard system to track performance metrics while giving team members autonomy in their daily work.
The key is to focus on building systems that can run without your constant involvement, rather than trying to train people to work exactly like you do.
Maurizio Petrone
Founder & CEO, PressHERO
Establish Clear Communication Channels
As I grew my business I realized delegation wasn’t just about handing off tasks—it was about creating a system where communication flowed. Having a clear communication channel made all the difference. It meant everyone knew what they were responsible for, had access to the resources they needed, and felt comfortable asking questions or giving feedback.
For instance, I set up a shared project management tool where tasks were outlined with deadlines, priorities, and relevant files. This one tool became our central hub, reducing the back-and-forth of emails or scattered updates. It also gave team members visibility into each other’s work, so they could see how everyone was doing and hold each other accountable.
What made this work was the clarity. When delegating I made sure to explain not just the “what” but the “why” behind the task. For example, instead of saying, “Design a report for this client,” I’d share the client’s goals and how the report would be used. This gave my team the ability to make decisions independently and often come up with solutions I hadn’t thought of.
For entrepreneurs struggling with delegation my advice is simple: start small. Delegate low-risk tasks first and use those opportunities to build trust and refine your communication process. Remember, delegation is not just about assigning work—it’s about enabling others to succeed. Be patient, provide guidance when needed, and celebrate along the way. Over time this will ease your workload and build a team that feels empowered and invested in your business’s growth.
Soubhik Chakrabarti
CEO, Canada Hustle
Create Clear SOPs and Assign Ownership
One strategy I found effective for delegating tasks and building a strong team is creating clear SOPs and assigning ownership instead of just tasks. For example, instead of personally reviewing every client ad campaign, I trained a team member to own performance tracking and optimizations using a documented process. This freed up my time for strategy while ensuring results stayed consistent. For entrepreneurs struggling with delegation, start by handing off a single responsibility with clear metrics—like client reporting—so you can focus on growth. The key is trusting your team and refining systems as you scale.
Keigan Carthy
Founder, Vision Management
Start with Small, Low-Risk Tasks
The most effective delegation strategy I’ve found is starting with small, low-risk tasks and gradually increasing responsibility based on performance. When I began scaling my own company, I initially struggled to let go, thinking nobody could match my standards. But I learned that by creating detailed process documents and setting clear KPIs, I could maintain quality while empowering my team.
For entrepreneurs struggling with delegation, I recommend starting with a simple system: document your processes step-by-step, identify tasks that drain your energy but could be handled by others, and hire people who are better than you at specific skills. The key is to view delegation not as losing control, but as multiplying your impact.
I’ve found that the best results come from giving team members full ownership of their areas, along with the authority to make decisions. When I delegated our content strategy to our experts across 23 countries, I provided clear guidelines but trusted them to execute. This approach not only improved our results but also increased team satisfaction and retention.
John Talasi
Entrepreneur, John Talasi
Hire Before You Are Ready
I hired before I was “ready” because I knew it would be essential for my business to grow. One of the most effective strategies for delegating and building a strong team was hiring people with strengths that complemented mine. My first hire was an administrative assistant because those were the tasks that were slowing me down and keeping me from focusing on the bigger picture.
For entrepreneurs struggling with delegation, my advice is to trust your team and give them the space to handle what they’re best at. When you’ve built the right team, they’ll come to you for solutions to the problems they can’t figure out alone. This lets you focus on scaling the business and bringing your vision to life. Don’t wait until you feel “ready”—delegation is a key step toward your growth as a business owner and leader.
Jessica Latimer
Founder, By Design Creative Agency
Provide Clarity and Context
Delegating tasks effectively is crucial for building a strong team as a business grows. One strategy I’ve found effective is to focus on clarity and context when assigning tasks. This means providing clear instructions, setting specific goals, and ensuring team members understand how their tasks fit into the bigger picture. I’ve seen firsthand how ambiguity can lead to confusion, delays, and poor results. By taking the time to provide context and clarify expectations, I’ve been able to empower my team to take ownership of their work and deliver high-quality results.
In my experience, entrepreneurs often struggle with delegation because they’re afraid to let go of control or worry that others won’t meet their standards. My advice is to trust your team and focus on developing their skills and strengths. When you delegate effectively, you not only free up your own time but also give your team members the opportunity to grow and develop. For example, I recall delegating a critical project to a junior team member, who not only exceeded expectations but also gained valuable experience and confidence. By doing so, I was able to focus on higher-level tasks and trust that the project was in good hands.
Michael Sumner
Founder and CEO, ScoreDetect.com
Document Failures to Identify Patterns
It’s all about practicing documenting failures rather than successes. Instead of creating perfect process guides, we started recording when and why tasks went wrong. When reviewing six months of project issues, we noticed a pattern: tasks failed most often when team members didn’t understand the broader impact of their work.
For example, when delegating client reporting, we started including notes about how each metric influenced client renewal decisions. This context transformed our team’s approach—they stopped just updating numbers and started highlighting trends that mattered for client retention.
One analyst spotted a concerning trend in mobile traffic and flagged it proactively because she understood its importance to the client’s business. Team initiative increased dramatically because people understood why their work mattered.
Error rate dropped because team members could make better judgment calls when faced with unexpected situations.
Matt Harrison
Svp of Product and Client Experience, Authority Builders
Foster a Culture Rooted in Core Values
As the founder and CEO of a med spa, one effective strategy I found for delegating tasks and building a strong team as our business grows is to foster a culture rooted in our core values: Leaders—Level Up, Excellence, Achieve, Diversity, Empathy, Relationships, and Strength.
- Leadership Development: I encourage every team member to see themselves as a leader in their role. By aligning tasks with individual strengths and aspirations, we create an environment where team members feel empowered to take ownership, make decisions, and contribute their unique perspectives.
- Excellence & Accountability: We set high standards for excellence, but we also emphasize the importance of accountability. When delegating tasks, I clearly communicate expectations and the desired outcomes, allowing team members to take the reins while knowing they have the support to succeed. This builds trust and reinforces their capability to lead.
- Foster Relationships and Collaboration: Strong relationships within the team are essential. I promote open communication and collaboration. This not only strengthens our bond but also ensures that everyone feels valued and heard, making it easier for me to delegate tasks effectively.
- Celebrate Diversity: Our team is made up of individuals from diverse backgrounds, and I leverage this diversity to enhance creativity and innovation. By recognizing and respecting different perspectives, we can tackle challenges more effectively and support each other in our roles.
Advice for Entrepreneurs Struggling with Delegation:
- Start Small: If you’re hesitant to delegate, begin with smaller tasks. This will help you build trust in your team’s abilities and gradually ease into more significant delegation.
- Communicate Clearly: Ensure that you articulate your expectations clearly when delegating. This includes outlining the task, the desired outcome, and deadlines.
- Let Go of Perfection: Understand that no one will execute tasks exactly as you would. Embrace the idea that different approaches can still yield excellent results. Focus on the overall goals rather than micromanaging every detail.
- Encourage Growth: View delegation as an opportunity for your team to develop new skills. Encourage them to take on challenges and provide support as they learn.
By fostering a culture of leaders, we can build a strong team that not only thrives individually but also collaborates effectively as a cohesive unit in our industry.
Beth Donaldson
Founder + CEO, skinBe Med Spa
Teach One Thing at a Time
If you are the glue that keeps the business together and the funnel that everything runs through, you don’t have a business, you have a job. You have to think bigger than yourself. Whether you’re just starting out or you’ve been in the game for a while, it’s so easy to attach yourself to the business and for it to be an extension of you. Your baby. But at one point, the baby needs to grow up and scale. If it’s all on you, YOU are the one stunting the growth.
Pick ONE thing and teach someone that one thing. Then remove that from your plate. If you have a handful of staff that are used to asking you for the answers to everything (because you normally give them the answers) start doing this: Whenever a question comes up that’s relevant to everyone, gather everyone up, answer the question, explain why you’re answering that way and then wait for any clarification needed.
This will slow things down at first, but as time goes on, fewer and fewer questions come up. If you work virtually, just do this with Loom videos. The goal is to eventually have a team that is truly an extension of you. THAT is when big things really happen.
Kevin Bell
CEO, KBellCo
Share the Big Picture
Being able to delegate effectively is a prerequisite to scale up your business.
It’s a gradual process that requires skill as much as a mindset.
Share the big picture, define boundaries for the role, and begin with delegating non-critical tasks. Be available to support when required. As he/she completes the task, have a freewheeling chat to understand what was easy for him/her and what was challenging. It also should give you a sense of the trustworthiness of the person. Use these as the basis to delegate more challenging and critical tasks.
Based on experience, keep raising the bar on delegation. Be mindful, commitment and dependability of the associate are as important as his competence.
Dr. Pramod Solanki
Leadership Coach and Founder, Performance Enablers
Implement a Mentorship Program
A strategy that I found effective for delegating tasks is implementing a mentorship program. Through this program, I gave plenty of projects to the best-performing employees. I could trust them as they have demonstrated their talent and dedication in their previous work. I knew they would complete them before the deadlines. For guidance, employees could seek their mentors. These mentors were the senior members of the company. As a result, they could complete the tasks with the required support and guidance. Besides reducing my burden, they could enhance their skills and knowledge. The mentors also reviewed their tasks and helped them to correct their errors. As a result, the tasks were unfailingly successful.
Rahul Kumar
CEO, RankSoldier
Leverage Automation Before Delegation
In a world where efficiency drives success, leveraging automation before delegation can transform how businesses operate. Automation tools like CRM software, project management platforms, and AI applications simplify repetitive tasks such as data entry, email marketing, and customer service. By automating these processes, entrepreneurs save time, reduce errors, and allow their teams to focus on strategic initiatives.
To determine whether a task is suited for automation, you should ask:
- Is the task repetitive? Routine activities like scheduling or invoicing are prime candidates for automation.
- Is there a tool available? Industry-specific tools, such as HubSpot for marketing or QuickBooks for accounting, can handle these tasks effectively.
- Does automation save time and resources? Although automation may have an initial cost, the long-term savings in time and efficiency make it a valuable investment.
Automation not only reduces workload but also empowers teams to dedicate their energy to high-value, creative tasks that drive business growth.
Once automation has streamlined operations, the next step is to delegate tasks that require human expertise. Effective delegation involves aligning tasks with the strengths, skills, and roles of team members.
- Match Tasks to Roles: Assign tasks based on team members’ expertise. For example, let a designer handle creative projects rather than administrative work.
- Provide Clear Instructions: Set clear expectations, outcomes, and deadlines to avoid confusion and errors.
- Empower and Trust: Allow team members autonomy to complete tasks their way while offering support when needed. Micromanaging stifles growth and creativity.
- Encourage Feedback: Open communication ensures tasks align with goals and gives team members a chance to share improvements or ideas.
Entrepreneurs often hesitate to delegate, fearing loss of control. However, trying to do everything alone leads to burnout and limits growth. Isn’t this why you hired your team? To foster innovation, and set the stage for scalable growth.
Mira Eszter Kőmíves
CEO, Multilingual Virtual Miracles
Focus on Hiring Self-Accountable Builders
I’ve always been a founder, so I haven’t had experience in larger corporations. This has pushed me to rely more on my intuition. When hiring, I focus on finding builders—people who are self-accountable and know how to manage upwards. It’s important to hire individuals who align with your values and trust that they will communicate openly. I also make use of tools like Slack so that I’m across developments and ensure regular sync-ups to keep everyone aligned.
Oliver Pugh
Founder, yetipay
