A Guide to Delegating, Letting Go (and Growing)


Scott D. Clary
Scott D. Clary
6 min readMay 20, 2024


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I’m writing to you today about a challenge that has plagued entrepreneurs since the dawn of time: delegation.

You know the feeling.

You’ve got a million things on your plate, each one screaming for your attention.

You’re juggling clients, managing employees, strategizing growth plans, putting out fires, and maybe even trying to squeeze in a workout or a family dinner.

It’s exhilarating, it’s exhausting, and it’s often unsustainable.

But here’s the kicker: as much as you might enjoy being the linchpin of your business, the truth is that you can’t do it all.

At least not if you want to scale. Delegation isn’t just a nice-to-have, it’s a non-negotiable.

So why is it so damn hard?

The Delegation Dilemma

Delegation is a delicate dance. It’s a paradox of control and trust. You want to maintain the quality and vision of your work, but you also need to empower others to take ownership.

You’re afraid of things falling through the cracks, but you’re also terrified of becoming a bottleneck.

The good news is, you’re not alone. Every successful entrepreneur has wrestled with these fears at some point. Even the most brilliant minds have their limits.

The even better news is that delegation, like any skill, can be mastered. It’s a matter of mindset, strategy, and practice.

So, buckle up, my friend. We’re about to dive deep into the art and science of delegation. Over the next few emails, we’ll explore:

  • The When: How to know when it’s time to let go
  • The Who: How to identify the right people to delegate to
  • The How: Proven strategies for effective delegation
  • The What: Which tasks you should delegate first

By the end of this newsletter, you’ll have a framework for delegating with confidence, freeing you up to focus on what truly matters: actually growing your business.

The When: How to Know When It’s Time to Delegate

As an entrepreneur, your time is your most valuable asset. So it’s crucial to use it wisely. Delegation is one of the most effective ways to do that.

But how do you know when it’s time to delegate a task? Here are a few signs:

  • The task is repetitive or time-consuming. If you’re spending hours on tasks that could be easily handled by someone else, it’s time to delegate.
  • The task is not your core strength. If you’re not particularly good at a task, it’s better to delegate it to someone who is.
  • The task is preventing you from focusing on more important things. If you’re feeling overwhelmed or stuck, it’s probably a sign that you need to delegate some tasks.

Of course, there are always exceptions. Some tasks are so critical or confidential that you may need to keep them in-house. But for the most part, delegation is a powerful tool that can help you free up your time and focus on what you do best.

The Who: How to Identify the Right People to Delegate to

Once you’ve identified the tasks you want to delegate, the next step is to find the right people to do them.

Here are a few tips:

  • Look for people with the skills and experience necessary to complete the task.
  • Choose people who are reliable and trustworthy.
  • Make sure the people you delegate to are clear on your expectations.

It’s also important to consider the personality of the person you’re delegating to. Some people are more independent and self-directed, while others need more guidance and supervision.

Ultimately, the best way to find the right people to delegate to is to experiment and see who works best for you.

The How: Proven Strategies for Effective Delegation

Delegation isn’t just about handing off a task and hoping for the best. It’s a deliberate process that requires clear communication, trust, and accountability. Here are some proven strategies to help you master the art of delegation:

  1. Set Clear Expectations: Don’t assume that people know what you want. Be explicit about the desired outcome, the deadline, and any specific requirements. Provide context for the task so they understand how it fits into the bigger picture.
  2. Match Tasks to Skills: Align tasks with the individual’s strengths and interests. This not only ensures better results but also boosts morale and engagement.
  3. Provide Resources and Support: Give your team the tools, training, and authority they need to succeed. Be available to answer questions and provide guidance, but avoid micromanaging.
  4. Establish a Feedback Loop: Regular check-ins are essential to track progress, address challenges, and offer constructive feedback. Celebrate successes and acknowledge effort to build trust and motivation.
  5. Let Go of Perfection: Don’t expect things to be done exactly your way. Embrace different approaches and allow for some autonomy. Remember, the goal is to achieve the desired outcome, not to control every detail.
  6. Empower, Don’t Burden: Delegation should be seen as an opportunity for growth, not a punishment. Frame tasks as challenges, not chores.
  7. Celebrate Success: Acknowledge and reward good work. Public recognition can be a powerful motivator and reinforce a culture of delegation.

The What: Which Tasks You Should Delegate First

Now that you have a framework for effective delegation, it’s time to start putting it into practice. But where do you begin?

Here are a few tasks that are often good candidates for delegation:

  • Administrative tasks: Email management, scheduling, data entry, travel arrangements, etc.
  • Repetitive tasks: Social media posting, content creation, reporting, etc.
  • Tasks outside your core expertise: Accounting, legal work, IT support, etc.
  • Tasks that are not urgent or critical: Research, brainstorming, etc.

By delegating these tasks, you can free up your time to focus on the high-level strategic work that only you can do.

The Art of Letting Go

Delegation is more than just a productivity hack.

It’s a mindset shift that allows you to unleash the full potential of your team and yourself.

It’s about trusting others, empowering them to grow, and creating a culture of collaboration and accountability.

Remember, delegation isn’t a sign of weakness.

It’s a sign of strength.

It takes courage to let go, but the rewards are immense.

So take a deep breath, trust your team, and watch your business soar.

The Challenges of Delegation (and How to Conquer Them)

Delegation isn’t always smooth sailing.

In fact, it can be downright messy.

But the key is to anticipate these challenges and have strategies in place to overcome them.

The Fear of Losing Control: This is perhaps the biggest hurdle for many entrepreneurs. You’ve built your business from the ground up, and the thought of relinquishing control can be terrifying. But remember, delegation isn’t about giving up control; it’s about sharing it. By trusting your team, you’re actually expanding your capacity to achieve more.

  • Solution: Start small. Delegate low-risk tasks first, gradually increasing the level of responsibility as you build trust. Establish clear communication channels and regular check-ins to stay informed and address any concerns.

Micromanagement: The urge to hover over your team and correct every little detail is a natural instinct, but it can be counterproductive. Micromanagement stifles creativity, erodes trust, and demotivates employees.

  • Solution: Focus on outcomes, not processes. Give your team the freedom to find their own solutions. Provide guidance and support, but resist the urge to dictate every step.

Lack of Trust: If you don’t trust your team, delegation will always be a struggle. Trust is built over time through open communication, transparency, and a track record of success.

  • Solution: Invest in your team’s development. Provide training, mentoring, and opportunities for growth. Celebrate their wins and acknowledge their contributions.

Communication Breakdowns: Unclear expectations, misaligned goals, and lack of feedback can derail even the best-laid delegation plans.

  • Solution: Be crystal clear about your expectations. Set SMART goals (Specific, Measurable, Achievable, Relevant, Time-bound) and provide regular feedback. Encourage open communication and create a safe space for questions and concerns.

Overwhelm: If you try to delegate too much too soon, it can overwhelm both you and your team.

  • Solution: Start slowly and gradually increase the workload. Delegate tasks in manageable chunks and provide adequate resources and support.

The Rewards of Delegation

Overcoming these challenges is worth it. Delegation is a game-changer for entrepreneurs. It can:

  • Free up your time: Focus on high-level strategic work that only you can do.
  • Empower your team: Boost morale, engagement, and productivity.
  • Improve decision-making: Tap into the collective wisdom and diverse perspectives of your team.
  • Increase scalability: Build a sustainable business that can grow without you being the bottleneck.
  • Reduce stress and burnout: Achieve a better work-life balance.

Delegation is an investment in your business and yourself.

It’s a journey of trust, growth, and transformation.

So embrace the challenges, celebrate the wins, and watch your business thrive,




Scott D. Clary
Scott D. Clary

👋 scottdclary.com | Host @ Success Story Podcast 🎙️ | I write a newsletter to 321,000 people 👉 newsletter.scottdclary.com