There are five reasons why a leader may fail to delegate work; understanding them for what they are is the first step on the path to learning to let go and start to delegate effectively. Key to the process is changing how you think about delegating – if you are “dumping and running” then you’re doing it wrong. Here we explore five ways to approach delegation in a new light that will make your organization stronger and make you even better as a leader.


Delegation is a critical skill that you as a leader must develop early on if you are going to be successful.  Today we’re going to talk about what it means to delegate, and a different way to think about delegating so that you can do it with confidence, improve your organization, and be successful as a leader!

Delegate or Die!

“You got to “Delegate or Die”  – that’s what one of my bosses told me long ago.  I was living in Panama at the time and had just stepped into a very busy job with a fast-paced Army unit.  We were responsible for planning and overseeing execution of everything that our unit of 500 paratroopers did every day.  We had people moving in every direction, flying in helicopters, jumping out of airplanes, training in the jungle, deploying throughout the hemisphere.

There were millions of things to think about, to coordinate, and to do.  And every bit of it seemed absolutely critical.  It was overwhelming.  My boss must have seen me struggling, and one day he pulled me aside, furrowed his heavy brow, pointed his beefy finger at me and told me, “Son, you got to delegate, or die!”

#Leadership survival tip: delegate or die! Click To Tweet

Like my unit so long ago, as your business or organization grows there are just so many things to do that it quickly becomes impossible for you to do them all.  Yet you see leaders arriving early and leaving late, constantly hounded by routine problems and issues, trying to juggle five things at once, and getting frustrated and worn out in the process.  Why don’t they let others do more of the work, even when there are people who could help them?

Five Reasons Leaders Fail To Delegate

There are a few reasons leaders may be reluctant to let go, but these reasons are often really traps that prevent them from focusing on what they should be doing to be successful.

1. Ease.  One trap is to think it’s just easier to do it myself.  They think that by the time they train someone, give them direction, answer all their questions, and possibly step in if things go wrong, it’s just a whole lot easier and quicker to just to it themselves.

2.  Perfection.  Another trap is the desire for perfection – the leader may also be the person who can do a particular task the best – he has the greatest skill, the most knowledge, and he can accept nothing less than the perfection, so he’s the one who has to do it – every time.

3.  Comfort Zone.  A third is comfort zone.  Not only is the leader is good at doing the task, frankly he would rather be doing that than some of the other things he should be doing.  So he stays busy down in the weeds doing the task because he likes doing it, but it is to the detriment of other aspects of the business that really deserve his attention.

4.  Control.  Yet another is the fear of losing control.  Leaders are often the “Type A” personality who naturally want to be closely involved in every aspect of the operation.  It’s probably what made them initially successful in the first place – they succeeded by doing everything themselves.  Letting someone else do a job means losing a bit of control, and giving some power and authority to someone else, and that can be a little scary.

Time to Think Differently

But if any of this describes your situation, it’s time to think differently about delegating, because if you don’t make a change, you are only going to wear yourself out and your organization will suffer.  It’s kind of like the guy who’s on a road trip, and his fuel gauge is pointing to empty, but he wants to keep going – he thinks he’s too busy driving to be able to stop for gas.   It’s time to do something before the tank runs dry.

Don't be so busy driving that you don't take time to fill the tank. Click To Tweet

It’s best to start by thinking of the reasons why you should delegate.  And the obvious first one is that if you don’t get some help, the situation will never improve, and your car will sputter to a halt somewhere out on a lonely desert highway 10 miles from the next gas station.

Four Good Reasons to Delegate

OK, got it, but it’s still hard to let go.  But here is where the change in thinking comes to help you take action:  It’s not about dumping your busy work on someone else, it’s about investing in your organization to make it better, stronger, and more capable.  It’s about making your team better so that it can continue to grow and succeed.  That’s what leaders should be focusing on, anyway, right?

1. It’s an Investment.  Begin by thinking of delegation as an investment in the growth and development of others within your organization.  Sure it will take a little time and effort at the front end, but at the same time, you are broadening the skill sets of your team members and increasing the depth of your organization.  And ultimately you are saving yourself much more time in the long run because they will be able to do the task every time it comes up, and with less and less need for you to be involved.

Delegating well is a form of investment in your people. Click To Tweet

2.  It Develops Trust.  At the same time, you are developing a higher level of trust with the person you’ve given the task to.  By taking the time to show them how to do the job, you are communicating that you have faith and confidence in them and their abilities, and they will want to deserve that trust by doing the best job that they can.  By pushing the ability and authority to act lower down in the organization, you are empowering your team to get things done faster and with less input from you.

3.  It Forces Clarity.  Beyond this, the act of delegating forces you to be clear about what needs to be done.  You have to be able to explicitly state the expected outcome, when it needs to happen, and why it is important.  If you are unable to do this, then it might be time to re-look the task in the first place.  As you go through this clarifying process, have someone write down what the task and procedure is, this way you end up with a written product as well as a trained person to do it.  You are creating an owner’s manual as you go.  If you lose the person you trained for some reason, you are still a step ahead on training the replacement.

4.  Allows You Time to Focus.  And finally, delegating allows more time for you to focus on what you should be doing.  Things like thinking strategically, setting vision and goals for the organization, managing the process, leading people.  So think of this as a better investment of your valuable time and skills as well.   The captain of the ship needs to be up on the bridge where he can command his vessel.  If he’s always down in the engine room shoveling coal, there’s no telling where the boat will end up.

The Takeaway

Twenty years ago, my commander was right – I was in the process of dying because I was failing to delegate.  But when I learned to trust my people, be clear about what was needed, and invested a little time to show them the way, we all ended up with a stronger team, and I was able to  back out of the weeds and focus on the bigger picture.

Now that we’ve talked about why delegation can be a good idea and a better way to think about it, in the next couple videos we’ll talk about how to pick the right tasks that you can delegate with confidence, and then how to go about the process of actually delegating them.

I hope you have found a nugget or two in this video that will help you as you develop your skills as a leader.  There are a bunch of other videos about leadership and how to become a good leader on my YouTube Channel.  I invite you to head there now if you’re not there already and check it out.   If you like what you see, go ahead and subscribe or share your thoughts in the comment section below – I’d love to hear from you.  Maybe you have a topic you’d like me to cover – let me know and I’ll take a look!

Until next time, thanks for watching!

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