💚 A Practical Guide to Delegation

Hello & Happy Thursday!

A year ago, we wrote a newsletter on the struggle of delegation and it quickly became one of our most-read issues ever.

It’s no surprise. The desire to delegate is nearly universal. The ability to do it well? That’s a different story.

I can personally confirm this, as it’s been one of my personal focal points over the last 8-months while scaling both Want To Work There and Training for the Modern Manager. And - real talk - it’s not easy.

For me, the hardest part is taking the time to document and teach versus doing it myself. I logically know that delegating is smarter in the long run, but when I’m on a tight deadline to get something turned around I often lack the energy and focus is takes me to hand the task off.

So when I saw that my dear friend Amber was getting ready to publish a book on delegation, I couldn’t hit the order button faster. Seriously, I bought both a digital and paper copy. If there was an audio version, I’d scoop that up too. Because, if there’s one thing I know about Amber, it’s that she shares my passion for moving past theory into the practical and actionable advice needed to achieve a desired outcome. Even better, she was excited to share her thoughts with Want To Work There readers!

As the guest writer of today’s issue, Amber offers not just permission to delegate, but a powerful framework for doing it better. Her Five Levels of Delegation tool will help you communicate expectations, calibrate trust, and coach your team into ownership (without burning out in the process).

Yours in moving beyond “I’ll do it myself”,

—Jill

P.S. Amber has a suite of free delegation tools on her site at amberlgray.com. They’re a goldmine of resources to keep this momentum going!

A Practical Guide to Delegation with Amber Gray

In 2021, my US-based virtual assistant agency was riding a massive wave of success and growth, mostly thanks to the normalization of remote work following the lockdowns during the pandemic. Revenue jumped 107% in one year, and our close-knit team was buzzing with excitement. Maybe you can imagine the energy around the virtual office…as well as the chaos of keeping the plates spinning behind the scenes.

My business coach shared a discouraging maxim: “Every time you double your revenue, you break half your team and half your processes.”

My positive mindset helped me dismiss it and keep going – until I couldn’t. Unfortunately, I was one of the ones that broke, aka burned out. And with hindsight as my teacher, I realize now that it could have been avoided if I had recognized earlier that delegation done well cultivates trust, empowers others, and liberates leaders. (That’s what I call the trifecta of delegation.) Instead, I sunk into a state of reacting, not leading. My operational systems began to break down. Our culture had been a pillar of our success, but with more of us burning out than burning on, team retention became a new problem.

Here’s the brutal truth:

Delegation as a skill might be the most overlooked area high-achieving teams are deficient in, and its impact is far more costly than leadership typically will acknowledge. The reason for this is simple – too simple, actually! Delegation is so easy to understand in theory but complex in practice, especially in fast-paced people-centered roles like yours.

The good news is that I learned a lot through trial and error and from our clients demonstrating what makes delegation a success versus a failure. (Enough to write a book about it, actually!) And now that I’ve sold the company after 10 great years, I’m dedicating my energy to helping leaders take back their lives by learning to delegate effectively. My goal with this article is to guide you to explore delegation as self-care, learn how to use the Five Levels of Delegation Decision Grid tool, and ultimately work with less hustle and more flow. Let’s dig in.

Why Delegation Breaks Down

Before we can understand the framework for effective delegation, we need to first acknowledge why it often breaks down. Delegation failure is almost always due to one or more of these common blockers.

1. There is a trust deficit. It can easily go unnoticed and even more likely become the elephant in the room everyone avoids, but a lack of trust is usually at the root of the problem if delegation is not being encouraged by and practiced regularly by team leads. But before we assign blame for this touchy problem, consider that just as easily as this could be due to a person who doesn’t trust others, trust deficits can be the result of missing tools or systems that offer the level of transparency necessary for all roles to see how they contribute to the big, overarching goal.

2. Expectations are unclear. There are several elements to the delegation process:

• the person delegating

• the person being delegated to

• the thing being delegated

• the frontend communication that initiates the transfer

• and the feedback given along the way or after completion of the task

With so many parts – including humans – involved, there are plenty of chances for things to go sideways. It usually comes down to insufficient communication before, during, and after delegating.

1. Perfectionism is getting in the way of progress. Leaders working in high-stakes circumstances are often subconsciously guided by their own internal stories leading to habitually deciding to do it all themselves. These stories usually sound like, “I’m the best person to do this because I’ve got the most experience with XYZ,” or “If I delegate this, it won’t be done right,” and “it’s faster if I just do it myself.” We decide to hold onto tasks and decisions because we want to make sure things are done exactly right. Not only is this a perfectly prepared recipe for burnout, it also prevents the development of the rest of the team.

What Happens When We Get Delegation Right

Let’s revisit what I call the trifecta of delegation. Delegation done well cultivates trust across the entire team, empowers every seat on the org chart to consistently level up, and liberates leaders from the claws of overwork and burnout. If we can shift away from thinking of delegation as just dumping tasks we don’t want to do, and instead adopt a mindset that views delegation as the key to developing people and scaling our impact, we can see the value in a commitment to improving our delegation skills.

My burnout story was a result of blocker number three. I thought I was the only person that could handle sales and client success because I had the relationships. I was the one networking and generating leads, so I thought it made sense for me to close the deals. And further, since I had built rapport with those people who eventually became clients, I thought I was the best person to match them with their VA, answer their emails when they had a question or were upset about a deliverable gone wrong, and everything in between.

When I finally realized this attitude was the source of my pain, I began to train a part-time employee to help with client success. It was a process that started with me copying her on emails and inviting her to shadow my calls. I also recorded Loom videos as debriefs of what I had done to resolve client issues. I wrote rough drafts of SOPs, and eventually extended smart trust to this employee and let her take the driver’s seat without me hovering over her shoulder. She recorded her client calls, I watched those videos, and gave specific, actionable feedback for improvements to apply on the next call.

The result? She didn’t do things exactly like me. She made a few mistakes. I had to step in a few times, and it created extra work for me.

And every single time, we both got better. She built trust with clients and improved her outcomes. They started going to her instead of me when they needed support. I got really good at delivering feedback in a kind and effective way. I grew my leadership skills and learned how to clarify my expectations. And as her autonomy increased, our trust increased, and my workload started tipping back to something more manageable, allowing me to focus more on future planning and growth strategies. She was eventually promoted, and later moved into the sales role where she really thrived the most.

It didn’t happen overnight or even over a few weeks, and at times it felt like I was going backwards, but my commitment to delegation ultimately saved the day.

The Five Levels of Delegation: A Tool for Building Ownership

Delegating well isn’t a one-size-fits-all skill. Just like I had to move gradually from copying someone on emails to fully handing off the role, there are levels of ownership we employ with every handoff. To bring more clarity and intentionality to that process, I use The Five Levels of Delegation Decision Grid, a practical tool I adapted from a Harvard Business Review article that helps leaders delegate with clarity and intention at every stage of trust and capability. This isn’t a ladder to climb. It’s a communication tool that helps you calibrate your expectations, match the right task with the right level of trust, and grow capability over time.

Here’s a quick overview:

• Level 1: Do exactly what I ask. (No autonomy)

  ”Follow the SOP.”

  Ideal for clearly defined, low-risk tasks.

• Level 2: Research and report back. (Restricted autonomy)

  ”Gather information so I can decide.”

  Great for projects that have been sitting on the back burner.

• Level 3: Recommend a solution. (Directed autonomy)

  ”Bring your opinion and let’s decide together.”

  Similar to Level 2, but leaning on their expertise a bit more.

• Level 4: Decide and inform me. (Broad autonomy)

  ”You own it, I just want visibility.”

  Use this level when trust is established, and you are ready to delegate responsibility as well as execution of the task.

• Level 5: Own the decision completely. (Complete autonomy)

  ”You lead, I trust.”

  This level is earned through consistent demonstration of competency.

The value of this framework is that it creates a shared language between you and your team members, so no one is left guessing what “take care of this” really means.

To help you apply it, I created a simple worksheet that maps each level of delegation to two key factors:

• The risk of the task being done incorrectly

• The experience or expertise of the person being delegated to

[Download the Five Levels of Delegation Decision Grid]

(Originally written for VA/client relationships, but universally applicable across teams.)

Common Delegation Pitfalls (and How to Avoid Them)

Even with the best intentions, delegation can break down quickly if we’re not aware of a few common traps. Here are six I’ve seen most often, and how to navigate them:

1. Believing you need a full team to practice delegation.

What goes wrong: You assume delegation isn’t relevant to you because you’re a team of one (or nearly one). Tasks pile up, and burnout creeps in.

Try this instead: Think beyond org charts. Delegation can look like empowering a peer to co-own an initiative, bringing in a fractional contractor, or documenting a repeatable process so you can hand it off when support becomes available. Creating clarity now makes it easier to delegate later.

2. Holding on too long due to perfectionism.

What goes wrong: You believe no one else can do it quite like you, so you keep doing it yourself. Meanwhile, you’re the bottleneck.

Try this instead: Delegate before you’re ready. Your team can’t grow into new roles if you’re still filling the space.

3. Delegating outcomes without context.

What goes wrong: You assign an outcome but leave out the “why” behind it. The team member completes the task, but it misses the mark.

Try this instead: Frame your delegation with both the outcome and the context. Understanding the “why” behind a task invites ownership and better decision-making.

4. Asking for help too late.

What goes wrong: You wait until you’re underwater before looping someone in and then expect them to move at your pace without a ramp-up.

Try this instead: Delegate early, before urgency creeps in. Trust takes time, and early handoffs build momentum before it’s mission-critical.

5. Confusing authority with autonomy.

What goes wrong: You assign a task but don’t grant the decision-making power to go with it. The person feels disempowered or stuck.

Try this instead: Use the Five Levels of Delegation Decision Grid to clarify how much ownership the task includes, and say it out loud.

6. Not making space for feedback.

What goes wrong: You delegate, but there’s no loop for follow-up, questions, or improvement. That silence can breed uncertainty or resentment.

Try this instead:

Normalize feedback in both directions. Debriefs and micro-coaching build confidence and strengthen the working relationship.

Bringing It All Together

Delegation done well isn’t a productivity hack, it’s a transformational, people-centric discipline that strengthens teams from the inside out.

For the individual leader, it’s a form of self-care. It gives you back the space to think, to create, to lead. To bring your highest and most valuable contributions. It lets you focus on the work that truly needs your special touch. That’s the path to less hustle, more flow, and it starts with cultivating trust in your team and creating margin in your day for the work that matters most.

For People Ops and HR leaders, your role is twofold. You’re a leader who needs to delegate, and you’re the person others look to for the how. The more you model thoughtful, trust-based delegation, the more you empower others to do the same.

Start small. Name it. Test it. Talk about it. And when in doubt, remember: those who delegate aren’t just dumping tasks to someone else – they are building a culture where clarity, ownership, and growth are the norm.

Things We’re Loving Right Now

New book alert! 🚨 Another friend of Want to Work There, Kari Ginsburg, recently published Hey Glitterbomb! A No-BS Guide to Being Too Much, Taking Up Space, and Loving The Legacy You Create and it’s officially in stores today!

Job seeking and feeling down about it? Careerspan is offering their career-coaching, resume-enhancing, confidence-building tool free for job seekers this summer. Learn more here >>

Even more insights on Gen Z. Last week we published a research-backed newsletter on what Gen Z really wants from work. Continue the conversation with this report from Gallup on Gen Z’s view of fully remote work.