How to Delegate Without Losing Your Mind (Or Your Team’s Respect)

How do you delegate so that things actually get done, your team feels empowered, and you don’t end up pulling all-nighters fixing everything? This guide will show you.

We’ve covered what to delegate and whom to delegate to in previous articles, so in this article we are focusing on the how.

But first, we need to look at a couple of essentials.

Before you start:

Remember what delegating is about

Delegation isn’t about throwing random tasks at people or avoiding things you don’t like, it’s strategic and purposeful. It’s about maximizing the results you get from each person on your team, not just you.

It’s also growing your people’s critical thinking, problem solving, and decision making capabilities. Your goal as a leader is to build a team that can run well without you and to raise future leaders that can replace you.

You aren’t controlling each detail, but you set clear outcomes and the context within which to operate, provide the resources and training, and release them to act on their own toward the outcome within the context given.

The level of delegation depends on the person and task

Your goal isn’t to control, but to set clear expectations and context, releasing your people to work within that, making the decisions and choices they need.

However, the level of “control” varies depending on the person. Dave Ramsey explained it like a rope. The more trust they have, the more rope you give them. The less, the shorter the rope.

If someone is new, you will likely be more involved in helping them learn, grow, and do it themselves. However, even in this process, your goal isn’t to control, but to help them grow to the point where they can do it on their own.

 A bad culture limits your delegation effectiveness

If you have a culture of fear and compliance, your effectiveness in delegating and achieving results will be limited. With a bad culture, people will fear innovating, speaking up, admitting mistakes, reporting issues, and disagreeing.

You want all of those things to be there when delegating. You want a culture where people feel safe speaking up, asking for help when needed, and admitting to you when they’ve made a mistake, so you can both work through it and fix it.  

Have the right mindset about mistakes and failure

It’s important to have the right mindset about mistakes and failure, and that begins with a growth mindset. When people fear making mistakes or failing, they don’t go above or beyond or focus on excellence. Instead, they focus on mistake avoidance. There’s a big difference.

Granted, a lot can depend on the task. If it’s a high-importance and high-stakes task with little room for mistakes, you will likely want to give it to someone who is experienced rather than someone brand new.

However, in many cases, it’s about learning. Innovation doesn’t happen without failures. They’re just stepping stones.

How you handle mistakes and failures matters a great deal when it comes to the work your employees will do, the communication they provide, and the results they achieve.

David Dodson in Deep and Deliberate Delegation says: “The clever delegator instills confidence, too, by framing the thing to be delegated not as a test to pass or fail but as an exercise in capacity development: ‘Lessons will be learned, and we will get there in the end’ is liberating, while ‘If you can’t do this there is something wrong with you’ is debilitating.”

Involve them in the planning

As much as you can, you want to involve them in the planning of the project or task they will be doing. This could be you both doing it together or them planning it themselves.

Whichever way you do it, the more you involve them in the planning, the more ownership they will have of the project or task.

How to Delegate

Now, let’s look at the steps you should take when delegating.

First, make sure you take a look at what needs to be done before having the conversation

Don’t rush in to give the task to someone. Take the time beforehand to examine the task.

Look at:

• The outcome you want to happen
• The skills that will be needed
• The resources that will be required
• Any systems, checklists, or helps that would be useful to the person doing the task or project
• The timeline of the project
• The importance of the project
• Potential issues, obstacles, and blockers
• They why behind the task/project

Also take time to look at the “who” to delegate to and the reasons why you want to delegate it to that person.

Granted, you may not always know or think of 100% of everything, and the person you delegate to may may come up with things or issues you didn’t think of. But by thinking through it, it helps prepare you for the conversation and process.

This doesn’t mean you go in and just lay out everything they need to do, when, how, etc. to them. You may work together or have them plan it, but by thinking through it yourself, you are in a better position to help them in the process.

Give the why

In general, your people should know the why, the mission, of your company, and how their jobs impact the mission, the organization, and its goals. They should understand the importance of their jobs.

At the same, when you delegate, you need to give the why of the project you are giving them. If there is no purpose or why behind it, then you need to rethink what you are doing. If it’s politics, that’s definitely something you need to work on.

Without a purpose, the task or project has no meaning. There’s not much motivation to do something that has no purpose in it.

When you are giving the project to someone, make sure the person understands the why of it and the context—how it fits into the big picture.

Give clear explanations

When sharing the project with someone, you want to set clear expectations and make sure that they are truly clear. (We have a whole article on how to set expectations here.)

Part of this is in the language you use. Make sure you use simple, clear language. When I say simple, I don’t mean that you should treat people as dumb, but the simpler it is, the easier it is to understand, and the less likely there will be confusion or misinterpretations.

Too many people try to be complex or use jargon or speak in complicated ways because they think it makes them look smart or because they think that is what business is supposed to be like.

But, #1, it’s not about you (and it doesn’t make you look smart, it just makes you look like you can’t communicate well), and, #2, that is not the way business is or should be. If you want good results, give clear, simple instructions.

Second is the content that you want to make clear. You want to make sure they can answer:

• What is the outcome?
• What are the measurements?
• How will a person know if they are on task and succeeding?
• What is their level of authority?
• What resources do they have?
• Who can they go to for help (besides you)?
• What is the timeline? The milestones?

You should have thought through this on your own beforehand, but some of this can be done together or by having them think through it on their own.

Make sure to be clear and watch your assumptions. It can be easy to assume people see things the way we see them and assume they understand what you mean when you say something.  

Remember, too, that there is a difference between high performance standards and perfectionism. You have high standards, and you hold them to them, but that’s different from being a perfectionist or being nitpicky about it.

Provide the context they should operate within

You have the outcome they are pursuing and the why and purpose behind it. That provides a good piece of the context they should operate within. But there may be other information you can give that provides context.

Your values of your organization may give context in what they do.

You may have certain systems in place that provides guidelines and context within which to operate.

There may be checklists they can use to guide them and parameters which they don’t need to cross.

You want to set clear expectations, give them the guidelines and parameters within which to operate, and then release them to act within those parameters while pursuing the outcome.

Pro tip: If you don’t have checklists or systems in place, you may want them to record what they do as they do it so it can be a guide for the future for others who do something similar.

Set clear deadlines and milestones

Sometimes projects have hard deadlines. Other times, they are more flexible.

If it’s a hard, inflexible deadline, make sure they know the deadline clearly. If it’s flexible, you may set a specific aim or you may work together or have them set one that they plan to aim for.

Especially for large projects, it can be wise to set milestones along the way to make sure you are on track. Some milestones may be obvious; other times, they may not be. You can set all of them upfront and adjust if needed as you go, but you may consider setting the first couple of milestones (especially if you are doing something newer) and then plan the next milestones based on how things go as you go.

Again, if possible, work out the milestones together during your discussion, or have them think through it and present their ideas to you.

Have them repeat the expectations back to you

Once you go through your expectations and set the context, have them repeat back the information to you.

Why?

To make sure what you said is what they heard. It’s easy, especially with hidden assumptions, to think people understand what you said—but often they don’t.

We all come from different backgrounds and experiences and see the world through different lenses.

Any easy way to ask is, “Just to make sure I was clear on everything, could you repeat back to me what’s expected for this project?”

And then you can keep asking questions if needed to clarify all the different areas of the project.

It’s better to fix a misunderstanding now than weeks down the road after miuch wasted effort, time, and frustration.

Equip them to succeed

What you provide will, of course, depend on the person and the task. You want to provide whatever training they need for the skills they will need for the project along with whatever resources they will need to complete it.

You may need to open doors or contact certain people for them.

If there are systems in place or checklists they can use, give it to them. If there are templates that can be helpful, do so.

If there are mentors or other people they can learn certain skills from or get help from, provide access to them.

If they are already overloaded with their current work, you may consider removing certain tasks or projects to help them focus on this one.

Make sure they have what they need to succeed.

Model and show them how to do it

If the task or project is new to someone, you likely want to model it for them first to teach them and make sure they understand how to do it well (or have someone else who knows how to do it).

There are different ways and models you can follow. When I taught elementary school, we followed the “I do, we do, you do” model.

I would show them how to do it, then we would do it together (and I would help correct any misunderstandings as we did it), then they would do it on their own (with me again, helping correct any misunderstandings).

Another method is one that John Maxwell mentioned in his book The Ultimate Guide to Developing Leaders. He said some nurses use ­the “Watch one, do one, teach one” method. They watch you do it, then they do it, then they teach someone to do it.

Having someone teach something really integrates it in their mind, so that can be a useful tool (even if they are teaching it back to you) depending on the task.

I mentioned this before, but checklists, again, also can be a useful took in this process.

However you do it, make sure you model and teach what they need.

Delegate the authority they need to accomplish it

Imagine a customer service representative who’s job is to resolve customer complaints, but every single solution requires them to go to the manager for approval. The customer gets frustrated waiting, and the rep gets frustrated with the inability to do anything (and loses ownership of the work), and you’re now pulled into issues you delegated in the first place.

One big mistake leaders and managers make when delegating is delegating responsibility without the authority to get the job done. It’s like handing someone a locked toolbox and expecting them to build a shelf.

As Dave Ramsey points out in EntreLeadership, “If you want to completely destroy the EntreLeader culture of your organization, there is one simple rule you can violate. The rule is, never give someone responsibility without the authority to perform.”

Why does this happen? It can be because managers:

• Fear losing control
• Don’t fully trust their team members
• Worry about potential mistakes
• Haven’t thought through what authority the person actually needs

When you delegate a task without the authority needed, you’re setting your team member up for failure. They’ll face roadblocks they can’t move, need constant approval for decisions, and eventually grow frustrated and disengaged. They will lose ownership in the work.

What authority might they need?

• Decision-making power within defined parameters
• Access to necessary resources, information, and tools
• Ability to communicate with key stakeholders or departments
• Budget authority (if applicable)
• Authority to request help from others

Ramsey also notes, “Titles don’t make leaders, and if you give someone the title and hold them to the results you must also give them the authority to act.”

Put it all in writing

Have you ever had a conversation where everybody remembers differently what you or they said or what you or they were supposed to do?

As mentioned earlier, it’s easy to make assumptions. We see things through different lenses. We also forget things or remember things differently.

If you don’t put what you’ve discussed and agreed in writing, then it can be easy for one (or all) to remember things differently, forget something they are supposed to do, and even work on the wrong things.

After you end your initial discussion (or as you have it), make sure to put it in writing and then send it out.

Communicate to all who need to know

When you delegate a task or project to someone, it’s not enough that just you and they know about it. You need to inform anyone who might be affected, anyone they need to collaborate with, or anyone whose authority might overlap with what you’ve delegated.

Who needs to know? Think about departments that might be impacted, other leaders whose teams might be involved, or individuals who typically handle similar tasks.

What should you tell them? Be clear about:

• Who you’ve delegated to
• What authority they’ve been given
• How this might affect existing workflows
• When the person will begin this responsibility
• Who to contact with questions (usually the delegate, not you!)

How should you communicate it? Depending on the significance:

• A simple email for minor tasks
• An announcement in a team meeting
• Direct introductions for major responsibilities
• Updates to organizational charts or responsibility documents

Without this communication, you create confusion that can undermine your delegate’s authority and effectiveness. They might waste time explaining their role repeatedly, face resistance from others who weren’t informed, or get stuck in organizational politics.

Follow up and support

You’ve delegated a task (or project), provided clear expectations, and given the necessary authority. Now comes a part many leaders miss or don’t do well—the follow up.

Have you ever delegated something (or had something delegated to you) and then… silence? No updates, no progress reports, just hoping everything’s on track? That’s a recipe for disaster.

Effective follow-up isn’t about hovering or micromanaging—it’s about providing the support and help your team needs to succeed. It’s like teaching someone to ride a bike: you don’t just give instructions and walk away, but you also don’t hold onto the bike the entire time.

How often should you follow up?

How often depends on a few factors:

• Experience level of the person (newer team members usually need more frequent check-ins)
• Complexity and importance of the task (higher stakes = more frequent check-ins)
• Timeline of the project (longer projects may need structured milestone check-ins)

That being said, ideally, you are already meeting your team on a weekly basis for a regular one-on-one. You can include follow-up during this time or set up a separate meeting for it. This allows for constant feedback, support, and course corrections that might be needed.

If you wait too long to meet, the other person may feel stuck, be wasting time with obstacles you can help with, or be off-track due to a misunderstanding and has been working on the wrong thing for a long time.

How to run the meetings

Generally, for your one-on-one meetings, it’s a good idea to have the team member lead it. This helps reinforce ownership and prevents the meeting from seeming like an interrogation.

Team members can discuss:

• Progress from the last meeting
• Current status
• Questions they have
• Obstacles or challenges they are facing
• Decisions they’ve made or need to make
• Resources or support they need
• Mistakes they’ve made
• Future plans
• Adjustments that may need to be made
• Or there may be some other aspect or topic that doesn’t fit this list

You can also ask questions to help in the discussion. Remember, your goal is to help and support, not “get” them. Open-ended questions are great questions to use.

Ask questions such as:

• What is your thought process in X?
• What did you learn from X (mistake or whatever happened)?
• What’s been working well so far?
• What accomplishments have you had?
• How can I help and support you?
• What obstacles or roadblocks are you facing?
• What do you think is causing these problems?
• What possible solutions have you considered?
• How do you think we should approach this challenge?
• What have you learned so far from this project?
• What do you think you will do differently?
• Do you need any additional resources or connections?
• Is there anything unclear or questions you have for me?

When things go off track

If progress isn’t where it should be, approach the situation with curiosity rather than judgment. Find out what is causing it to go off track.

Some common causes include:

• Your delegation: Did you provide clear expectations? Sufficient resources?
• External obstacles: Are there barriers outside their control?
• Skill gaps: Does the person need additional training or guidance?
• Personal factors: Are there other work demands or personal issues affecting performance?

If the other person made a mistake, focus on helping, supporting, and redirecting. As Ken Blanchard said in his book, Leading at a Higher Level, unless someone is just being lazy (or something similar – and don’t just assume that is what it is), a redirect is better than a reprimand.

Balancing ownership and support

To support your team members, it can be easy to jump in and try to fix it yourself. Don’t do that though. That keeps them from learning and growing, and it keeps you from focusing on what you need to do most.

Resist the urge to:

• Take the task back when challenges arise
• Solve all their problems for them
• Make decisions they should be making
• Insist they do things exactly your way

Instead, use questions to guide their thinking and help them develop their problem-solving muscles. You might occasionally share your experience or perspective, but try to always ask for their thoughts first.

Remember, the goal of delegation in general isn’t just getting a task done—it’s also developing your team members’ capabilities.

Finish well

You’ve met with the person, set clear expectations, followed up consistently, and now the project is done. Time to jump to the next task, right?

Wrong.

A big missed opportunity many leaders miss is what they do (or don’t do) at the end of the project. How you finish can make a big difference between continuous learning and improvement versus repeating the same mistakes.

The Debrief

Think of a debrief like a post-game analysis that great sports teams do. They study what happened­—both positive and negative­—so they can do better next time. Jocko Willink in his content also talks about doing the same thing after a military mission.

When the project ends, whether it was successful or not, you want to sit down with the person and debrief about the project. This isn’t about blame or even praise—it’s about learning.

Ask questions such as:

• What went well?
• What didn’t?
• What challenges did you face?
• What mistakes were made and what did they teach you?
• What did you learn from the process?
• If you could go back to the beginning, what would you do differently?
• What did you learn that might help with future projects?
• What advice would you give to someone else doing a similar project?
• What could I have done differently or better in the process?
• What did I do that helped you/hurt you?
• How did “luck” factor into it?

Depending on the project and current resources, you may even consider having the person document their process, key decisions, and lessons learned. This creates resources for others in your organization as time passes.

During this meeting or elsewhere, you also want to give whatever feedback you may have for them to improve. You want to share what they did well, but also areas that could get even better. Ideally you have a culture of feedback where it’s the norm, and your goal is about helping them improve and get better, not punish, put down, or vent.

Give Recognition Where It’s Deserved

Make sure you give credit where it is due. Give praise to the person and be specific about it. If the project is being presented to other people, make sure others know who did the work.

Make sure you give praise and appreciation to them privately, and depending on the person (some really hate it), publicly praise them in front of others.

A general good framework to use is Situation->Action->Impact. The situation could be the problem or things surrounding the delegated task (as well as the task itself), the action would be the work they did, and the impact is the results from the work.

Two more notes

One: don’t accept shoddy work – that’s what you’ll keep getting. This is something you should have addressed way earlier in your feedback sessions—if it’s still shoddy here at the end, you likely failed in some part in the process and need to evaluate so you can do better next time.

Two: Look at your role in the process and how you can improve. Part of the questions in the debrief is about you. Take time yourself to examine what you did well, what you can improve, and if things didn’t go as well as you wanted, what you could have and can do differently so that doesn’t happen again.  

Bonus: Premortems and contingency planning

One strategy you can use when planning the project with the person you are delegating to is to do premortems and contingency planning.

Premortems are where you say “It’s 6 months down the road and this project failed—why did it fail?” You list out all the ways it could have failed and then work on ways you can prevent those failures from happening.

Contingency planning is similar. It’s looking at the possible issues and problems that might arise and creating plans to overcome them if they do.

Just thinking through the process can help you and your team member better plan and make the project happen.

The impact of great delegation

Delegation isn’t just about freeing up your time—though that’s certainly a benefit. It’s about building a team that can accomplish more than you ever could alone. When done right, delegation multiplies your impact, develops your people, and creates an organization that doesn’t depend solely on you.

Remember that each time you delegate effectively, you’re doing more than completing a task. You’re:

• Building trust with your team members
• Developing your team members
• Creating systems that can scale beyond you
• Expanding your organization’s capabilities
• Teaching critical thinking and problem-solving skills

The first few times you do this might take longer than doing it yourself. That’s normal. But over time, as your team grows in capability and confidence, you’ll find yourself able to accomplish exponentially more through them than you ever could on your own.

What could you delegate this week that would free you to focus on your highest-value work? More importantly, who on your team needs the growth opportunity that delegation provides?

Your next great delegation could be the one that transforms both your team member and your organization.