The Messy Delegation Dilemma

If you’ve been a leader for long, you’ve likely encountered a situation where your valiant attempts at delegation backfired on you.  As you abandon your priorities in order to clean up the mess that was left behind, you can’t help but wonder, “Is it worth it?”  You’ve heard all the great speeches about empowering others.  You know the all too familiar cliché “you have to give up to go up.”  But no one really tells you how to handle it when delegation results in failure.  How do you handle when those you lead make mistakes?  What mistakes are necessary and good for development and which mistakes are flat out failures?

What do you do with the proverbial ball that’s been dropped or the wobbly plate that finally spun off its axis?  The analogies are well known for a reason.  These are the difficult parts of leadership.  They don’t come with quick fixes or formulas.  They come from instincts and intuition.

Early in my career I encountered the delegation dilemma.  Excited to be newly promoted and have a paid employee reporting directly to me, I arrogantly began barking orders.  Within a couple of days my frustration was growing.  This new wonderful employee was not doing things exactly as I had directed or requested.  Certain that he would see it my way, I wait straight to my boss to express my exasperation.  I expected my boss to pull the employee in and remind him that I was the boss and he needed to do things my way.  Instead my boss turned it into a teaching moment for me.  I’ll never forget what he said, “You’re not working with widgets, you’re working with people.”

He didn’t need to say anymore.  I wanted my employee to be a robot.  I wanted him to do what I said exactly the way I said it.  But leaders don’t lead robots.  Leaders lead intelligent people who have their own opinions and ideas, people who can add more knowledge to a task, people who want to spread their wings and learn by doing it their own way.  That was the day I learned leadership isn’t about barking orders; it’s about whispering possibilities.

Leaders understand that one of their chief responsibilities is developing people.  And sometimes developing people means loosening the reins on your personal preferences and giving those you lead the latitude to fail and learn for themselves.  Personally I would rather avoid a mess than clean up a mess, but in delegating we actually need to embrace the mess. We have to prepare ourselves for things to not work out perfectly every time.  We have to understand that things will get a little messy.

Great leaders are great guides.  They discern when to make helpful suggestions.  They know when to assist.  They use their intuition and instincts to allow just enough mess to create an environment of learning.

But what exactly does that look like?  How do you know when to guide and when to direct?  Here are some questions I ask myself when I’m facing the delegation dilemma:

• Am I more concerned about how I will look or how the employee will look?  In other words, am I afraid a little bit of failure will make me look bad? If it’s more about my image than about helping someone grow, I need to reevaluate my leadership priorities.

• Will what the employee gains in experience outweigh the consequence to the organization?  Any miss or failure is likely to have some impact on the organization but is it one that can be easily absorbed in order to help the employee learn from it?  Will the short-term cost be worth the long-term gain?  Count the cost and make the best decision for everyone involved.

• Will letting the ball drop allow them to learn?  Will it develop them further? Sometimes it will.  Other times you can teach them just as well by explaining the potential pros and cons of an idea or action before it’s taken.

Leadership is not easy.  It’s messy and complicated.  People are unique and different and therefore you will need to lead everyone just a bit differently to find the best way to develop them.  While delegation may be messy, the payoff of seeing someone grow and learn is worth any clean up required.   

Jenni Catron is a church leader and author of the book CLOUT: Discover and Unleash Your God-Given Influence.  You can follow Jenni on Twitter .