How to delegate

One of the hardest things for many leaders is delegation. This is especially true for start-ups and small businesses/nonprofits where founders/CEOs wear many hats and often feel they lack resources to get the right support.

Although, they’re not the only ones. 

Delegation skills are an expression of several personal and leadership qualities, so regardless of the support system, or the lack thereof, we’ve all known people who’re great delegators, but also those who aren’t. 

So, if you have a couple of minutes, let’s tackle this topic together. 

Do you struggle at delegating and why?  

Before I share my thoughts, take a moment and write down three reasons why you struggle to delegate: 

At the root of delegation, there are five intertwining themes—I call them themes, because they’re complex.

  1. Control 

  2. Awareness

  3. Trust

  4. Resources 

  5. Structure / Process


I’ve written a lot about control and our need for control. 

But if you don’t have time to read that, what’s the simplest way I can explain why we [try to] control?

We are afraid. 

In the context of delegation, we might feel, “what if the person fucks up … what if it’s not as good… what if we lose a client… what if … fill in the fear.”

What are you afraid of? 

In the personal context, this fear might mean … what if you fall in love and you get hurt (so you don’t give relationship a real chance); in work, what if you ask someone to do something and they don’t do it as well as [you think] you would (so you try to do it all by yourself); 

Can you really control these things without negative consequences (i.e. losing an awesome person, getting burnt out, etc…)?


In order to let go of control, and make good, unafraid decisions, awareness is key.

Indeed, awareness is essential to becoming and being a good leader.  

Sure, there are things you can do better than anyone else.

But you are definitely not the best at everything. 

What are three top things you bring to your company, job, nonprofit, etc? 

You have to be brutally honest with yourself—this is where a coach can be helpful—and understand what your competitive advantage is. What is that one thing *no one* can do but you?

In my line of work, for people who want to see me, could I delegate one-on-one coaching or my leadership talks?


But I could delegate social media, marketing, or sales, right?

What if my intern makes a typo on that post, it reflects poorly on me, right? 

But what if they don’t? 

(See how control crept in there?)


The next step is to build [a culture of] trust, so even when mistakes do happen, and they will, we know our team did their best and will learn from it. 

Trust is essential in any dynamic, work or personal. This includes self-trust.

Trust, of course, requires trustworthiness (you cannot be trusted unless you’re trustworthy). But when we are intentional about building both through honesty, consistency, vulnerability, communication, awareness, among others—we are poised to thrive. 

There’s a great book on this, The Speed of Trust by Stephen Covey (the son of the original personal development guru, also named Stephen) 

Without trust, there are no quality relationships or teams. Whenever there is trust, people can thrive. Now imagine your venture (or life) enveloped with the culture of trust!

Alright, back to delegation. 

Why do you not delegate?

Likely because you are afraid, therefore trying to control.

How do you stop trying to control?

Understand that you’re doing it and why (we cannot change what we aren’t aware of); then, bring awareness into it: understand what your key contributions / drawbacks are. Then, build a culture of trust so that delegating is safe—knowing that people have your best interest in mind can help you loosen up your grip (if you choose to let it, of course). 

Once this deeper, broader dynamic is out of the way, we look at who will do the delegated tasks and how we will structure the process.


A lot of leaders try to do it all instead of getting the best people to do it.

I get this a lot.

Why do I need a coach/advisor/facilitator, can’t my HR person do it? Well, for the same reason I need a hairstylist or a doctor.

Therefore, a wise leader will know to identify resources to help them on their quest. And if they don’t know how to get those resources, they will seek help from someone who does. 

It was Steve Jobs who said, “It doesn’t make sense to hire smart people and then tell them what to do. We hire smart people so they can tell us what to do.” 

Identify your resources in all areas of your business (or life) and then utilize them! 

This will free you up greatly to focus on what truly matters and what you’re best at. 

Structure & Process

I often tell leaders and managers: define the floor and the ceiling, and let your people do their best work in-between those two anchors. 

The final key to effective delegation is building the structure and process:

Step 1: identify the right person for the task (don’t assign random tasks to available people)

Step 2: communicate clearly the parameters (ceiling / floor)

Step 3: create a feedback loop so you know the project is on track

If you have taken care of your resources properly (i.e. hired the right people), identifying the right person for your delegated tasks will be easy.

When communicating what needs to be done, use the old journalistic approach of 5W’s and an H: what, why, where, when, who, and how… this is a great test to see if you’re being clear. Just make sure you are first clear with yourself.

Trusting environment will help make sure that people feel comfortable to ask for clarification.

Communication and feedback loop will be most constructive and effective when you’re aware of your own tendencies as we discussed above. Your awareness of your controlling tendencies and your own strengths will prevent you from, well, being a control freak and overbearing, making your follow up and the whole delegation mechanism work and people feeling comfortable to share where they’re at and/or ask for help.

Since these are personal and leadership skills, there is a lot more to delegating and learning how to delegate than reading a blog post, but I hope this gives you a good start. 

Please let me know if you have questions about this post or topics you want to me to cover in the future. 

Now go and delegate!

Adi Redzic