A Leader’s Two Best Friends

As I mentioned previously I recently began a new position as Interim Director of Worship at Covenant Life Church in Sarasota, FL.  This position is my first step back into senior level leadership since 2009, and while I am excited about what God is going to do, I also know I have challenges ahead of me.

As a result I have been spending a lot of time writing and thinking about what it takes to grow a worship ministry.  So far I have written about

In order to lead well, however, I am finding I need to have close friends.  These friends are not the financial officer of my church, the executive pastor, the senior pastor, or even the chairman of the elder board, although good relationships with these leaders are highly necessary.

I have written several times about my mistakes when I began a new position in 2010.  I plowed ahead with my agenda, pulling everyone with me.  When I finally began to listen to my volunteers I was able to make changes and avoid burning everyone out.  I would have done well to engage the help of two friends right from the start.

These two friends are Questions and Observation.


Making questions your friend means focusing on asking questions rather than making statements.  Questions do several things:

  • Invite interaction.  A good question fosters communication and collaborative effort.
  • Demonstrate humility.  Asking a question shows people you do not have it all figured out and you are willing to learn.
  • Unearth information.  Obviously, asking a question guarantees you will learn more about those around you.  Refusing to ask questions prevents you from truly understanding your surroundings.
  • Direct discussion.  Sometimes the best way to lead a discussion is to asking a carefully crafted question.
  • Create ownership.  If you engage a volunteer in conversation with a question, that volunteer will own the ensuing decision.


Observing people and systems reveals critical information you will not discover by reading the employee handbook or studying staff biographies.  Here are just a few benefits of observation:

  • Reveals hidden attitudes.  Body language comprises the majority of our communication.  Watching body language in a conversation gives a much better picture of what the other person is thinking and feeling.
  • Reveals unresolved issues.  Avoidance, for instance, can communicate unresolved tension or a lack of interdependence between separate ministries or departments. Other behaviors such as sarcasm, avoiding eye contact, or abrupt communication can also tell you that something is not right.
  • Reveals broken systems.  If I observe, for instance, that the song lyrics displayed on Sunday are not in the correct order, I discover that either I did not give the proper information to the projectionist, the projectionist was not at rehearsal to fine tune the lyrics, the projectionist messed up during the service, or I made a change from the stage and the projectionist was not able to follow.  That observation can lead to a discussion that will improve the flow of information and guarantee better projection on Sunday.
  • Reveals pain.  If you observe that a co-worker or volunteer is more subdued than usual, a good question can often lead to an encouraging discussion and even prayer.  Worship leaders need to be particularly observant of the people they are leading in worship in order to respond and lead more effectively during the service.  Many people are hurting and need to know they are not alone.
  • Shows that you are listening.  In order to observe you have to stop talking and listen.  I am amazed at what I hear and understand when I shut my mouth and listen.  People love a listener, as I am certain you do, too.
  • Reveals what is going well.  As a teacher I was often reminded to “Catch someone doing something right.”  This rule applies in leadership as well.  Catch your volunteers doing something right and congratulate them.  Smile and cheer when your choir shapes a phrase correctly.  Be a cheerleader for your volunteers, friends and family and they will follow you wherever you go.

What other “friends” have helped you in leadership? 

Trello: One of My Favorite Productivity Tools

Trello is a collaboration tool that organizes your projects into boards.  In one glance, Trello tells you what is being worked on, who’s working on what, and where something is in a process.”

My brother, Matthew R. Overholt, recently introduced me to this tool and I have been using it ever since.  He and I are using Trello to manage a software development project. He loads updates of the software to the related card and I download it for testing.  I can upload drafts of my information and record my research for him to work through as he has time.  We find it immensely helpful.   I like Trello so much that I have started migrating some of my To Do lists there as well.

In the past I have tried many things to manage my To Do lists.  First, I did not have one.  OK, that failed miserably.  Somewhere along the way I decided to keep my list on my Palm (remember those things).  Not good.  The Palm platform did not offer enough flexibility and things would sit on there and I would end up ignoring it.  Next I tried an Excel spreadsheet.  At first I thought this would be the solution.  I could create lots of lists on different pages and notate what I was doing or had done or had to be done.  Being a bit of a perfectionist, however, I would get caught up keeping the list up to date and not actually doing anything.

After that I went to using yellow legal pads.  Why yellow?  Beats me.  I just seem to be able to read them better.  This way I could make a new one every week, cross things out as I go, and make notes at meetings.  These legal pads were my most successful method by far.  I still find that writing things down longhand is very good for me, even therapeutic (Check out my blog Ink for more of my thoughts on this.).

After quite a while I began experimenting with Evernote.  Thanks to Michael Hyatt I have really gotten into this flexible platform of keeping notes.  While I am driving on the road I can speak notes to myself, sing a new lyric idea, record a few new lines to a poem, or any number of things, and the information is immediately synced with the web and my computer.  I can do no better than Michael Hyatt in describing the use of this tool, so check out his blogs on Evernote.  For me, however, I like to be able to use bullets and other formatting tools when dealing with To Do lists, and these things do not sync well from computer to iPhone, which frustrated me immensely.

Enter Trello.com.  First of all, the Trello app is spectacular and perfectly mirrors what you do on your computer, which is vital for me.

Here is a brief description: A “Board” has a set of lists on it, defaulting to “To Do,” “Doing,” and “Done.”  You can add as many Lists as you want and rename them as well.  On one Board I have added a List called “Resources” where I am keeping information that I access regularly.  On each List you can place as many “Cards” as you wish.  Each Card is a task within the List.  For my church job I have a “Choose March Pianists” Card.  On that Card I have placed a checklist for the four Sundays in the month waiting to be checked off.  A handy progress bar indicates how far I am towards completing the checklist.  On the Card I can add notes on my activity as I go (02/10 – Emailed X pianist about playing on March 4), and I can upload attachments easily to the Card as needed.  I can also label Cards with colors to indicate urgency, and much more.

The only downside I have found up to now is that I cannot go in and add an update to an individual entry on the card, which is probably my perfectionism working overtime!  I imagine this is because the notes on the card are a record of progress, particularly in working with others, since this is primarily a collaboration tool.

I am just beginning to use this tool, but I highly recommend it.  I can easily move cards from list to list, manage the information, and not have 20 lists on my desk.

Do you use Trello.com?  If you do, what are your favorite features? If not, what do you use to manage your projects and To Do lists?