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The Biggest Mistake Leaders Make In Delegation (Learn To Delegate Like A Pro)

I recently took my team to Leadercast 2014.  During our lunch break I was asking everyone on our team what their greatest takeaway from the morning was.  Our 20 year old program director, Meredith, floored me with her response.  I realized that I had learned the same lesson after years of struggling with delegation.  However, she picked up on it and put words to my greatest challenge with delegation in a few hours.  I learned a lot at Leadercast, but I didn’t expect this lesson on how to delegate tasks.

How to delegate to my team.

Image courtesy of Stuart Miles /

Back to my conversation with Meredith.


Me to Meredith; “What’s your greatest takeaway so far?

Meredith; “I’m good at delegating tasks.  I’m terrible at delegating decisions.

And there it was my friend.  I realized I had mastered task delegations years ago.  In fact, pretty quick into my leadership journey I had delegating tasks down.

  1. Identity the next action step required.
  2. Decide the best equipped person to handle the action step.
  3. Assign it to them.
  4. Record the assignment in whatever task management system I was using at the time.  (I’m now 100% on Nozbe and loving it thanks to Jackie Bledsoe Jr.).
  5. Followup with the person when the action step requires it depending on difficulty, due date, etc.

Pretty simple.


But, I never felt like I was getting ahead.


How about you?  Do you feel more or less free to dream about the vision of your organization and how to reach it as you delegate more and more?  I for one was always confused.  Why was I still so swamped when I had everything delegated out?


Enter Dave Ramsey book Entreleadership.


From Mr. Ramsey, I learned and use the 3 suggestions rule.  (Actually, I only require 2.)  The rule is this.  When you bring me a problem, come with 3 (or 2) suggestion on how to fix it.  After I’m presented the problem and the suggested solutions I decide on a course of action.  I make sure the person knows why or why I’m not using one of their suggestions.  Over time, I learn how my team thinks and they learn how to think like me when solving problems.  After a few rounds of this, I can eventually say; “You no longer need to bring problems like this to me.  I trust you to decide.”

Overall, this has been working great.  And Meredith helped me see what I was actually doing in this process.  I was delegating decisions.

When I would simply delegate task in the past without delegating the authority to make decisions….I was setting my team up to have to come back to me with questions.  However, once I started passing on the responsibility to make decisions I started noticing more time in my day to focus on the things that only I can do.

With Dave Ramesy’s approach I am teaching my team how to make decisions.  Thus, delegating decisions making when the team member is ready.  Now that Meredith has helped me connect the dots, I’m going to be able to be even more intentional.


What I Have To Stop Doing.


I also had another light bulb moment.  And, that lead to me apologizing to my team.  Recently I would reply like this when asked about something I didn’t need to be involved in.  “You decide, I don’t care.”

What I thought I was saying was this; “You can decide this.  I trust you.  I don’t need to care about this, because you have it covered.”

What I now realize I was covertly communicating.  “You decide.  I don’t care about small things like this.  It’s such a small decision, it’s beneath me.  You are only capable of handling this kind of small thing and I don’t care.  Only bother me with the big important stuff.”

Not what I thought, felt nor meant.  But the words we use matter.

Now, I will simply reply;  “Thanks for asking.  However, I trust you.  I’d like for you to decide.  I’ll support you whatever you decide.”  And, after saying this a few times, I’ll just cut it down to; “You can decide this.  I trust you.”

What About You?  Do you delegate decisions as well as you delegate tasks?


What Do You Know?


I would appreciate any insight you can share on delegation in the comments or by sending me an email.



Why and How To Lead With Grace


Leading can be messy.

Leading can be exhausting.

Leading can be the most rewarding thing you ever do.

There are so many opinions on what “THE KEY” to being a great leader is.

Frankly, there isn’t one. Leadership is the high school janitor’s giant ring of keys. Leadership is complex and multifaceted.

Image courtesy of graur codrin at

Image courtesy of graur codrin at

With that image in mind. We now have this questions. “What is the key ring?”

What’s the thing that keeps all of the keys of successful leadership held together?

I believe the key ring of leadership is Grace.

Let’s define Grace. If you are speeding down the highway and get pulled over, here is what could happen.

  1. You get a ticket. This is because you are under the law and your ticket is justice, and what you deserve.
  2. You get a warning. This is forgiveness. The cop could have given you the ticket, but decides to be forgiving.
  3. The cop walks up to your window and gives you a jelly donut. You are getting something you don’t deserve for being in the wrong, this is Grace. (Just a side note to my fellow believers of Christ…consider this analogy for a moment in your relationship with God. Powerful to consider God gives us jelly donuts everyday.)

When’s the last time you extended Grace to someone you lead?
How are you going above and beyond the expectations of those you lead?

Don’t you want Grace extended to you? My marriage wouldn’t be what it is if my wife and I didn’t exchange Grace regularly. My relationship with my children…same thing. My team at work, ditto.

Now, before someone comments that, “but sometimes you don’t have a choice. As a leader a time will come when you have to fire someone.” True. But do it with Grace. Make sure you really know the whole story first. I’ve never fired anyone who was surprised. Everyone is gifted and capable at doing the right work, But if you judge a tree for it’s ability to have empathy and walk with an upset costumer towards a resolution, you’ll end up with the a big pile of wood chips and no oxygen.


Hand Out Jelly Donuts Every Day


  • Look for new ways to develop the skills of your team.
  • React to screw ups by working with them to fix it.
  • Overreact to right decisions and under-react to mistakes.
  • Get out of your office every day and be present with your team.
  • When you think you have given enough, you have almost started giving enough.
  • Remember, what gets rewarded gets repeated.
  • Create a great environment by getting the wrong people off the team.
  • ?What other Tips and Suggestions Do You Have?


  • Consider a situation you are facing. What will the jelly donut look like?


Question: What other tips do you have to lead with Grace? Where do you disagree with me in this analogy of Leadership? What do you believe the key ring is?  I’d appreciate your thoughts, please comment. 



How To Make Feedback a G.I.F.T.


I recently heard a guy at church tell this story about his son, we will call his son Ted.

Ted goes golfing for the first time with some friends.

His friends were all hitting the ball more then 150 yards.

Image courtesy of pat138241 at

Image courtesy of pat138241 at

Now Ted, golfing for the first time, could only hit the ball 50 yards.  And, he had a terrible slice.  His ball kept landing almost off the fairway, but at least he was still in the open fairway and could see his ball.  One of the other kids had a pretty much equal slice.  But, he was hitting his ball about 200 yards…his ball was in the trees, in water, in the sand…pretty much anywhere it shouldn’t be.

The only difference at play between Ted and the other kid was distance.

We also see this principle in workplace leadership.

The further you allow someone on you team, or the team itself, to go in the wrong direction..the greater the error.

If you avoid a conversation with someone because it will be uncomfortable, the eventual conversation will just be worse.

If someone is causing dissension amongst the team with a negative attitude, negative talk, laziness, gossiping etc.  The longer you allow the issue to go…the greater the damage.


Error Increases With Distance.


  • Don’t wait for annual reviews to give feedback.
  • Have regularly scheduled one-on-ones with your direct reports.
  • Empower supervisors to immediately address problems.
  • Make Gossip a fireable offense.  (Here’s a post with more on that)
  • What gets rewarded gets repeated.  (tweet that) Pay more attention to positive decisions and beneficial attitudes then to negative ones.
  • Make feedback a GIFT:
    • Genuine – Don’t give blanket statements such as, “Good Job”.  Read Matt McWilliams post for more on this.
    • Immediate – Don’t wait, give feedback as soon as possible.
    • Friendly – Don’t be a jerk. You aren’t in your position because no one else can do your job, you are there because you got there first.  Check your ego at the door.
    • Tailored – Read The Five Languages of Appreciation in the Workplace.  Reinforce desirable decision making by showing appreciation to each person on your team in the manner that they most appreciate.  For some it will be a quick email.  For others a conversation at lunch.
  • Never put an end date on your training for new hires.  Training never ends.  Perpetual training, mentoring, coaching…whatever you want to call it…fosters the greatest teams.
  • ?What other Tips and Suggestions Do You Have?


  • Order The Five Languages of Appreciation in the Workplace. If you already have it, read or reread it.
  • List all of your direct reports.  Schedule a reminder for each person this week to check in with them.
  • Consider having a weekly or bimonthly one-on-one meeting with each direct report.
  • When’s the last inservice you had?  Maybe it’s time to schedule another one.
  • Subscribe to my blog so you never miss a list of suggestions and tips for better leadership.


  • What variations or alterations would you suggest?


Thanks For Reading

Nothing Leads Like The Truth

This post appeared in Frontline Festival. A blog carnival full of wisdom and oozing practical leadership advice on leading frontline team members. Check it out. Frontline Festival

Every player on a NFL football team towers in size over the Referees.  But these “little” guys with their little yellow flags and little toy whistles have complete authority.


The players choose to give them authority.

99% of the time, the Referee sees and knows the truth because of their position in the game and knowledge of the rules.

As leaders, we should be asking for the authority to lead and then watch for and share the truth constantly.

Nothing moves people more effectively then truth. (I’m blushing, but can tweet that)


Courtesy of Brit_2 via @Flickr

Courtesy of Brit_2 via @Flickr


I train 30 college students every summer to be leaders at camp.

We spend the first 24 hours of training on one thing:


Build a bridge strong enough to bear the weight of truth..



  • Hire character over anything else. People with character tell the truth.
  • Model well, more is caught than is taught.
  • Train both sides of leadership.  Following well is part of the equation.  Don’t just teach leadership, teach following.  People need to learn how to tell the truth well and how to hear the truth with integrity.
  • Train your staff to take conversation the last 10%. Many leaders walk away from conversations thinking, “What I should have said was….”  If it’s not mean spirited, but is truth meant to build the bridge, say it!

?What other Tips and Suggestions Do You Have? Please Comment


  • Always tell the truth.
  • Remember training never ends. Keep the mindset of facilitator, coach, mentor, leader..whatever it takes to keep from thinking of yourself as supervisor, boss, in-charge, etc.
  • Get to know each persons Language of Appreciation in the Workplace and learn to speak these languages. I have found nothing that builds trust and strengthens relationship better. (affiliate link)
  • Spend time eating a meal with your team with no “shop talk” allowed. If you can, cook the meal together. This builds relationships
  • MBWA Manage By Walking Around.  Let your team see you doing your job, takes the mystery out of it.  It will be easier to trust you.
  • Don’t allow or participate in Gossip, ever.

?What other Tips and Suggestions Do You Have? Please Comment 


  • Resolve with a pre-decision to never lie, no matter what.
  • Write a mission statement for your leadership.
  • Write a letter to your team with goals and promises about your leadership. Imagine you will give it to them on their last day on your team.  Then, develop a plan to achieve the goals and meet the promises you make.
  • Read The Five Languages of Appreciation in the Workplace
  • Find a mentor.

What variations or alterations would you suggest? Please Comment


Thanks For Reading

Reach For Excellence By Staying In The Middle


Icarus was the son of Daedalus. They were imprisoned on an island together. Daedalus used his skills as an inventor to build wings for himself and Icarus. He used wax and string to fasten feathers to reeds of varying lengths to imitate the curves of birds’ wings.

Leadership Lesson On Reaching for Excellence Based on the story of Icarus

Courtesy of by EC_Hallex 


As they stood on the highest cliff about to take flight, Daedalus warned Icarus to fly at medium altitude.  He warned, If they flew too high, the sun could melt the wax of their wings.  Fly to low, and the sea water would dampen and weigh down the feathers.  Either way, the wings would fail and death would be unavoidable.

As any young boy would, Icarus became exhilarated once in flight. Ignoring his father’s warning, he flew higher and higher. Sure enough, the sun melted the wax holding his wings together, and Icarus fell into the water and drowned.

This story has a great cautionary lesson for leaders.

Excellence is found by a continues pursuit of providing sustainable delivery of the mission better than you did the day before.  (tweet that)

Sustainable, that’s the key.  I could grow our organization very quickly.  I have the knowledge and skill to, and I’m sure that’s the same with you.

But what good is rapid growth, without the systems and ability to maintain it over time?  In business we can’t work from a wristwatch, we have to work from a calendar.  I learned this lesson the hard way, through failure.

We should always always always be reaching to deliver the best.  But, that doesn’t mean reaching up…it means reaching out.  Like Icaras, fly to high and you will get burnt.

Here are some ways flying to high can bring an organization down:

  • Using debt to expand your business.
  • Growing by adding new staff too quickly.
  • Hiring staff without a ridiculously thorough screening and interview process.
  • Declining quality in the pursuit of quantity.
  • ??? Add to the comments your warnings of flying to high.

But wait.

Icarus was also warned about flying to low.

Here are some ways flying to low can bring an organization down:

  • Settling for the states quo.
  • Getting caught up in, “we’ve always done it that way”.
  • Buying into the praise and hype of your most thrilled customer, which will cause you to become complacent.
  • Trying to please everyone by not standing firm in your convictions.
  • ??? Add to the comments your warnings of flying to low.

As a leader, I must be ever watchful for the dangers of flying to high.  But, I must also make sure we don’t get comfortable or lazy and fly to low.  I want us to continue moving into the ever expanding horizon of our future.  I want us to use wisdom to achieve excellence.

How do you keep your organization flying “just right”?  What other lessons can you pull from Icarus?  If you disagree with me, why?

Thanks For Reading

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