How To Delegate

Everyone deserves the respect of clear communication, meaningful context, thoughtful support, and a tight feedback loop.

Apr 28, 2025

The best leaders do not just get things done. They develop the skills of the people around them who get things done.

Many managers resist delegation for understandable reasons. You may feel that explaining a task will take more time and effort than completing it yourself. As a result, you stay overwhelmed and overloaded.

Alternatively, you may send out quick, vague emails asking someone to "handle" something, only to find that the results bear little resemblance to what you had in mind.

Delegation resistance often stems from two mindsets:

A need for control, believing that others will not meet your standards. This can lead you to spend your valuable time formatting spreadsheets and polishing slide decks.
A sense of guilt, worrying that assigning work will burden your team. This can cause you to keep tasks that others would see as exciting opportunities for growth.

Both patterns keep you stuck and rob your team of chances to build skills and ownership.

Whether you are delegating to a senior colleague, a peer, or a junior team member, the principles of effective delegation remain the same.

Everyone deserves the dignity of clear expectations, meaningful context, thoughtful support, and timely feedback. Delegation is not about hierarchy. It is about partnership, growth, and trust.

👋 Hey, it’s Jess. Welcome to my weekly newsletter, Thought(ful) Leaders, where I share practical tools and frameworks, share research, and interview thoughtful leaders on the future of work.

⛑️ Work with me for 1:1 executive coaching or book a workshop for your team.

If you’re not a subscriber yet, here’s what you missed this month:

Subscribe to get access to these posts, and all future posts.

Why Delegation Matters

Delegation is a leadership skill that simultaneously strengthens your team and frees you to focus on the strategic work that only you can do. When you withhold delegation, you remove a development opportunity for someone else. You also delay your own growth into a higher-value leader.

When you find yourself holding onto a task, pause to ask:

Does this genuinely require my personal attention?
Who might do this better than I could, or at least equally well?
Who might view this as a learning opportunity rather than a burden?
What strategic work am I neglecting by doing this myself?
If I were to move on tomorrow, who would be prepared to take this on?

By answering these questions honestly, you begin to shift your mindset from "getting things done" to "building people who get things done."

Why Delegation Often Goes Wrong

Even when managers attempt to delegate, they often swing to extremes. Some over-brief, providing lengthy instructions that leave no room for creativity. Others under-brief, simply assigning tasks without context or clarity.

Effective delegation lies between these two extremes. It combines clarity, context, support, and trust.

Wes Kao offers a helpful framework called CDAF (Clarity, Context, Why This Person, and Feedback Loops) for structuring effective delegation (Kao, 2024). I recommend keeping this acronym in mind when you’re preparing to delegate and to double check that you’ve done it well.

Here are my top tips for delegating based on what I’ve admired in other leaders and what’s personally worked well for me.

1. Clarity: Make the Ask Clear and Simple

State the task plainly. Assume the other person knows less about it than you do. Use screenshots, demos, decks, or reference materials to illustrate what you mean. Consider recording a short video walk-through using tools like Slack Clips or Loom. A visual example grounds the conversation and gives them a resource to return to.

2. Context: Explain the Bigger Picture

People are more motivated when they understand the "why" behind the work. Share:

Why this task matters right now
How it ties to broader business goals or customer needs
Who will be impacted by the outcome
How their work will contribute to a larger mission

Context creates meaning. Meaning fuels motivation.

3. Why Them: Personalize the Opportunity

Share why you selected them for this task:

What unique skills or strengths do they bring?
How does this align with areas where they want to grow?
How might this project showcase their talents in a creative or strategic way?

People feel empowered when they know you see potential in them.

4. Define Results: Clarify Success

Paint a clear picture of what success looks like:

What are the standards of quality?
What constraints exist, such as deadlines, formatting, or approvals?
Who will use or rely on the completed work, and how?

Explain both the positive impact if the project succeeds and the risks if it misses the mark.

5. Resource and De-risk

Think ahead about what might go wrong. Share any common pitfalls you have seen on similar projects. Provide resources, such as documentation, templates, systems access, and introductions to people they might need to consult.

Proactive support prevents problems before they arise.

6. Validate and Connect

Rather than asking someone to parrot back instructions, engage them in conversation:

What are your initial thoughts on the project?
What challenges or obstacles do you foresee?
What do you think the best next step should be?

This approach builds a peer-to-peer relationship, invites collaboration, and creates psychological safety for asking questions.

7. Establish Tight Feedback Loops

Agree on early check-in points. Especially for new or less-defined projects, tighter feedback loops reduce the risk of misalignment.

Frame check-ins not as "checking up" but as opportunities to surface questions, unknowns, and adjustments together.

For example, you might say, "Take a first pass at the plan and let us review it together tomorrow. That way, we can catch anything early."

Short feedback loops build momentum and confidence.

What is the true purpose of this task? Remember to consider if this task should exist at all before pawning it off on someone else.
Who might benefit from the opportunity to take this on?
What is the minimum you must specify, and where can they decide independently?
How will you support them without micromanaging?
Can someone else completing this to seventy percent of your standard be better than you doing it at one hundred percent?

Delegation Pitfalls to Avoid

Do not delegate without context. Without understanding the bigger picture, people may misinterpret goals or quality standards.
Delegate authority along with responsibility. Empower them to make decisions within clear guardrails.
Maintain regular check-ins, even brief ones. Frequent touchpoints allow you to celebrate progress, correct course early, and continue coaching.

Final Thought

Delegation is not just about getting work off your plate. It is about building a team that feels trusted, challenged, and equipped to succeed. Whether you are delegating to a senior leader, a peer, or a junior colleague, the fundamentals stay the same.

Everyone deserves the respect of clear communication, meaningful context, thoughtful support, and a steady feedback loop. When you delegate with clarity, context, and care, you do not just get more done, you’re growing other thoughtful leaders around you.

If you need some support, book a free strategy call and we’ll walk through what’s working, what’s not, and where to begin.

If you want to support Thought(ful) Leaders, the best way is simple: share this newsletter. Forward the posts you love to a friend or colleague, or encourage someone to subscribe. That kind of word-of-mouth makes all the difference!

Thanks for being here. More soon.