Leanne Woof delves into the common reasons why entrepreneurs struggle to successfully outsource and delegate tasks to virtual assistants (VAs) or online business managers (OBMs). With a wealth of experience as an OBM herself, she shares her determined nature and problem-solving mindset, offering a fresh perspective on why outsourcing may not have worked for you in the past, and how you can finally make it work. Whether you’re feeling frustrated, overwhelmed, or simply stuck, this post provides invaluable insights to help you overcome the bottlenecks and achieve the leverage you need to scale your business.

As a visionary entrepreneur, you’ve poured your heart and soul into building a thriving business that impacts lives and shapes communities. However, as your venture continues to grow, you find yourself increasingly overwhelmed by the day-to-day tasks, leaving little time for strategic thinking and creative exploration. Outsourcing to a virtual assistant (VA) or online business manager (OBM) seems like the logical solution, but if you’ve tried it before with little success, you may be tempted to write it off entirely.

But what if the key to unlocking sustainable growth and regaining your freedom lies in understanding the hidden reasons behind your past outsourcing failures? In this insightful blog post, we’ll delve into the mindset blocks, communication breakdowns, and mismatched expectations that can sabotage even the most well-intentioned outsourcing efforts. By the end, you’ll have a clear roadmap to overcome these obstacles and finally find the perfect VA or OBM fit for your business one that empowers you to scale your impact without sacrificing your life priorities.

What this post covers:

• Delegation is a long-term game, not a quick fix. It requires consistent work and the right processes to thrive.
• Mindset issues, such as the inability to relinquish control or trust others, can sabotage your outsourcing efforts.
Finding the right personality fit between you and your VA/OBM is crucial for effective communication and collaboration.
Unrealistic goals or a mismatch between your desired outcome and the outsourced person’s skills can lead to failure.
• Self-awareness and open communication are essential for identifying and resolving outsourcing challenges.
• Sometimes, the issue isn’t you or the VA/OBM but the incompatibility of your working styles and personalities.
• Experienced VAs/OBMs can provide valuable context and guidance on achieving realistic goals.
• Be open to exploring different approaches or seeking alternative experts to achieve your desired outcome.
• Don’t write off outsourcing entirely if it hasn’t worked in the past, with the right mindset, team, and approach, it can be a game-changer.
• Continuous learning, adapting, and seeking support are key to making outsourcing work for your business.

Listen now:


The Mindset Hurdle

One of the biggest barriers to successful outsourcing is our own mindset. As visionary leaders, we’re used to having complete control over every aspect of our businesses. The thought of relinquishing that control to someone else can be daunting, even paralysing. We may harbour fears about trusting others with our baby or doubts about their ability to execute tasks to our standards.

“And so if you have this conflict inside you, where you want to be able to scale, you want to be able to expand what you’re doing, But you can’t let go of the control, you’re constantly going to have This war inside, and you’re not going to see the result because we’re not focused on an outcome here.”

However, it’s important to recognise that this inability to let go of control can severely limit our ability to scale and achieve the leverage we crave. As our host eloquently puts it, “The longer you hold on to that control, the harder it is to delegate and create leverage. That’s just the reality.”


Overcoming the Control Dilemma

The key to overcoming this control dilemma lies in self-awareness and a willingness to shift our mindset. We must understand that delegation is a long-term game, not a quick fix. It requires consistent work and the implementation of the right processes to thrive.


“If you find that you’re out of capacity right now, you have zero time, bringing in somebody is going to give you relief. It is not going to give you relief tomorrow. It is not a magic wand. It’s not a silver bullet. There is work that goes with it, like everything else.”


Instead of viewing delegation as a loss of control, we should embrace it as an opportunity to empower others and focus our energy on the strategic, visionary aspects of our business. By letting go of the day-to-day tasks, we create space for creativity, innovation, and growth.


The Personality Puzzle


Even with the right mindset, outsourcing success hinges on finding the perfect personality fit between you and your VA or OBM. As our host emphasises, “The personality matches are really important if you want this to work and you want it to work successfully.”

“Someone who you can communicate easily with, somebody who gets it, and someone who you get. The personality matches are really important if you want this to work and you want it to work successfully.”

A mismatch in personality can lead to communication breakdowns, frustration, and a general feeling of being misunderstood, even if both parties are highly skilled and well-intentioned.


Finding Your Kindred Spirit


The solution lies in taking the time to find a VA or OBM whose communication style, work ethic, and overall approach aligns seamlessly with your own. This may require interviewing several candidates and being unafraid to politely pass on those who don’t quite fit the bill.

“And so you find these clashes and you can end up in this position where it’s a matter of standing there and going, why doesn’t this ever work for me? Like These are good people and I think I’m a good person, so maybe this just doesn’t work for me. But no, it actually just has to do with that combination.”

Once you find that kindred spirit, someone who “gets” you and can anticipate your needs, the outsourcing process becomes infinitely smoother. Open communication flows naturally, feedback is welcomed, and a genuine partnership forms, allowing you to achieve far more than either of you could alone.


The Goal Alignment Conundrum


Even with the right mindset and personality fit, outsourcing can still falter if there’s a mismatch between your desired outcomes and the skills or expertise of your VA or OBM. This misalignment can stem from unrealistic goals on your part or a lack of understanding of the specific capabilities required to achieve those goals.


Bridging the Gap


To bridge this gap, it’s crucial to have open and honest conversations with potential VAs or OBMs about your goals and desired outcomes. Don’t be afraid to ask probing questions about their approach and seek their professional input on the feasibility and best path forward.

“And so if it’s not worked for you before, maybe it is that what you’re trying to achieve doesn’t really match with the person or the skill that you’re trying to achieve it with. And you’ll only uncover that by talking to more people by saying, Hey, this is what I want to achieve. How would you go about it? Or who is it that I need?”

By embracing a growth mindset, being open to feedback, and surrounding yourself with the right team, you can overcome the bottlenecks that have held you back and finally experience the freedom and leverage you’ve been craving.


The Path to Outsourcing Mastery


Mastering the art of outsourcing is a journey, one that requires continuous learning, adaptation, and a willingness to seek support when needed.

“If you’re still stuck, and you cannot work out why it doesn’t work for you, DM me, at Audacious Empires, I want to talk to you, I want to help you.”

In some cases, you may discover that your initial goals were misguided or that a different type of expertise is required. This is where the value of experienced VAs and OBMs shines, they can provide valuable context, suggest alternative approaches, or even recommend seeking additional expertise to ensure your goals are achieved efficiently and effectively.


The Bottom Line:

As a visionary entrepreneur, your time and energy are precious resources, ones that should be dedicated to the strategic, creative aspects of your business that truly light you up. By overcoming the mindset blocks, finding the perfect personality fit, and aligning your goals with the right expertise, outsourcing can become the game-changer you’ve been seeking.

Imagine having a team of skilled professionals who not only understand your vision but also have the capacity to execute it flawlessly. Imagine regaining the time and mental space to explore new opportunities, forge deeper connections with your audience, and amplify your impact in ways you’ve only dreamed of.

The path to outsourcing mastery starts with a single step, a willingness to confront the obstacles that have held you back and a commitment to finding the solutions that will propel you forward. Take that step today, and watch as your business soars to new heights, fuelled by the leverage and freedom you’ve always craved.


Over to you

What’s been your biggest challenge in outsourcing and delegating tasks to a VA or OBM? Share your experiences in the comments below, your story could provide the inspiration someone else needs to finally overcome their own outsourcing hurdles.