Training Session 37: (Becoming) 2nd Mile Servant Leaders

To cultivate 2nd mile servant leaders

Key Scriptures
Matthew 5:41; Luke 9:46-48; Luke 22:24-26; Mark 10:35-45


“Servant leadership is en vogue right now” writes Sameer Dholakia, CEO of SendGrid.1  One of the most compelling reasons servant leadership is en vogue in our culture right now is because it works.  We like things that work. We like strategies that increase the bottom line. Dr. Bob Liden, professor of management at the University of Illinois at Chicago and a leading scholar in servant leadership research, summarizes the benefits found by scholars who have studied servant leadership in corporate and professional settings.2  Scientific research has shown that servant leadership…

  1. Enhances people’s self confidence in their ability to perform specific tasks well (study done by Walumbwa, Hartnell, and Oke, 2010)
  2. Creates a service climate and a fair workplace (Walumbwa, Hartnell, and Oke, 2010)
  3. Fuels creativity among employees (Liden, Wayne, Liao, and Meuser, 2014)
  4. Positively impacts job satisfaction (Mayer, Bardes, and Picccolo, 2008), psychological contract fulfillment (Panacccio, Henderson, Liden, Wayne, & Cao, 2015), and organizational commitment and worker engagement (Van Dierendonck, Stam, Boersma, Windt, and Alkema, 2014).
  5. Yields greater employee commitment to the organization, job performance, and community citizenship behavior (Liden, Wayne, Zhao, and Henderson, 2008).
  6. Positively influences the relationship between goal clarity, team potency, and performance (Hu & Liden, 2011).

Followers of Jesus, however, aren’t interested in servant leadership merely because it works; we are interested in servant leadership because Jesus called us to servant leadership.  Jesus said if you want to find your life, lose it through service (Matthew 10:39); if you want to be great, serve (Matthew 20:26). Regardless of whether it works in the sense of yielding greater profits or any of the benefits listed above, we’re under orders to serve from our High King.  He wasn’t ambiguous or vague. He said, “whoever wants to be great among you must be your servant” (Matthew 20:26).

This will never happen without humility, which is why we began by laying a foundation for servant leadership in last week’s training session on humility.  Servant leadership builds on the foundation of humility because it is the way to live out humility.  Humility, as we explored last week, is valuing others’ interests above your own (Philippians 2:3-4).  Nothing values someone like saying, “You matter. I value you enough to put your interests above my own by serving you.”   In our training session this week, we’re going to explore how to activate humility through 2nd mile servant leadership so that we can become 2nd mile servant leaders.  Let’s examine each one of those key terms.  2nd mile.  Servant.  Leadership.  They all matter.

2nd MILE

Jesus teaches about the importance of going the 2nd Mile in one of the most ethically challenging sermons ever given, the Sermon on the Mount. Buried in the middle of His hard-hitting Sermon on the Mount is a leadership principle that can and will change your life, if you are courageous enough to try it. And fail.  And try it again, and fail again, and keep trying it every day until you get better and better and better. Here’s the teaching: ”If someone forces you to go one mile, go with him two” (Matthew 5:41).

Hear that.  Jesus gives humility and servant leadership a very practical goal—go the 2nd mile.  When we hear this, we’re not shocked.  We should be. First century listeners would have been shocked, if not outright offended.  Here’s why. They all knew the legal requirements placed on them by the occupying Roman army.  Jews and Gentiles alike were required, by law, to carry anything a Roman soldier asked them to carry for up to one mile, in any direction.

As a result, Jews and Gentiles did their best to avoid Roman soldiers, at all cost.  So many bad things could happen in the presence of Roman soldiers, including being asked at any moment to carry a really heavy burden a long way.  On average, it takes about 20 minutes to walk a mile. Throw in a heavy burden and a hot sun and that time increases to 45 minutes to an hour, easy.  Now double it, and you realize Jesus was telling them to go 2 plus hours out of their way (if they’re hoofing it), not to mention the perks of sweat-stained clothes, nefarious body odors, and dust in every crack and crevice of your body.

Now we’re starting to see why the 2nd mile was both shocking and offensive in the first century.  It was asking too much of them and it feels the same way to us.  Very few of us will take over two hours out of our day to do anything for anyone, especially if we have to sweat doing it.  Maybe, if momma calls, but this isn’t momma. Jesus says do it for the person who is the bane of your existence (like the Roman soldiers!) Why?  Why does Jesus ask this of us?

Because the first mile is expected; the 2nd mile is expectation shattering.  In so many ways and in so many places, Jesus calls His followers to not simply meet expectations, but shatter them.  Morally, He calls us to “Live such good lives among the pagans that, though they accuse you of doing wrong, they may see your good deeds and glorify God” (1 Peter 2:12).  Financially, He calls us to shock the world with our generosity (Luke 21:1-4). Emotionally, He calls us to “do everything without grumbling…then you will shine among them like stars in the sky” (Philippians 2:15).  Professionally, He calls us to a standard of excellence, doing everything (including our job!) for the glory of God (1 Corinthians 10:31).  We could go on and on and the message is always the same. Don’t just meet expectations—shatter them! Doing so both glorifies God and grows opportunities of influence.

How?  By going the second mile. Let me illustrate.  I was driving to work recently and had a Super Big Gulp cup  filled with my daily and delicious green smoothie. Tragically, the moisture on the side of the cup led to a fumble.  I watched with horror as my Super Big Gulp, filled to the brim, splashed all over the beige interior of my new ride (well, new-to-me).

Turns out 50 ounces of blueberries and kale don’t enhance the look of beige interior.  What now? I knew I needed help. Fast. I exited the interstate and thought, “Well, there is a Chick-Fil-A.  They will spare a few napkins.” I ran in and said, “I’m so sorry. I just spilled my smoothie all over my car.  Can I use some of your napkins?” The woman behind the counter said, “You need more than napkins baby. You need help. I am coming to help you.”

I laughed.  She grabbed a bottle of cleaning spray, 4 towels, a bucket of soapy water, and headed out to my car.  I insisted on cleaning it up myself. She wouldn’t have it. She was Rock-of-Gibraltar strong in her insistence that she was going to serve and I had better get with the program, so I did.  For 20 minutes, she sprayed, wiped, and scrubbed every ounce of blueberry sludge out of my car. I thanked her profusely. Guess what she said? Shocker. “It’s my pleasure.” That is 2nd mile servant leadership.

Offering napkins would be the first mile.  I expected that from any fast food restaurant, especially Chick-Fil-A.  The spray bottle, towels, and 20 minutes of scrubbing shattered my expectations.  That’s what the second mile does. It shatters expectations. It establishes a culture.  It creates questions.

Ironically, a few hours after my Chick-Fil-A smoothie experience, I ate lunch at another restaurant which must not be named.  I was given a number to place on my table. The waitress brought our food. She was kind. She wore a huge smile and said, “Is there anything else I can help with?”

There was.  Since I had never dined here before, I queried, “Where is the silverware?”  She pointed, “Right by the drink machine.” She turned and headed back to the cash register.  That’s first mile service. She delivered the food with a smile and fulfilled her job responsibility.  It wasn’t in her job description to get silverware for customers. Someone else was responsible for putting it out and the silverware was there for the taking.  In her defense, she did nothing wrong. Expectations were met, but the difference between scrubbing a smoothie and pointing to a fork is all the difference in the world.  The first mile is expected; the second mile is expectation shattering.


What we’ve been describing is the type of leadership Jesus calls us to: 2nd mile servant leadership.  We just covered the 2nd mile part of the equation; now, let’s talk about our role as servants.  There are different leadership theories in life and in the business community, such as the transformational leadership model and the leader-member exchange theory of leadership.  Jesus believed leaders serve. Period. If we’re honest, we prefer to be kings, not servants. The disciples of Jesus had the same hankering for the top of the food chain, not the bottom.  Not once, not twice, but thrice they got all hot and bothered about who would have the most impressive job title with the corner office (Luke 9:46-48; Luke 22:24-26; Mark 10:35-45).

Despite hearing Jesus teach and model servant leadership for three years, the disciples just couldn’t get it.  Or maybe they didn’t want to get it, like us.  Hours before the ultimate servant leader paid the ultimate price of service, the disciples were still arguing “which of them was considered to be the greatest” (Luke 22:24).

Jesus mercifully resisted cracking them over the head and instead took one last crack at teaching servant leadership.  He says, “The kings of the Gentiles exercise lordship over them…but not so with you. Rather, let the greatest among you become as the youngest, and the leader as one who serves” (Luke 22:26). Greatness, in His eyes, is measured differently.  The greatest are the greatest servants.

But what does Jesus’ principle of leading by serving look like in a competitive business context?  Can I still compete? Let’s allow two business consultants to answer this question. Ken Blanchard, author of over 60 books including the One Minute Manager, Raving Fans, and Lead Like Jesus, says servant leadership in business requires the leader to flip the traditional business pyramid.  “You must philosophically turn the instrument upside down because you now work for your people.”3 In a servant leadership culture, strategic leadership serves operational leadership; operational leadership serves the frontline employees; and frontline employees serve the customers.


The difference is, well, everything.  One results in frontline employees cleaning up blueberry sludge because of a culture of 2nd mile servant leadership; the other results in frontline employees pointing to silverware because it’s not in their job description. Kevin Kruse, author of Employee Engagement 2.0: How to Motivate Your Team For High Performance, described the impact of 2nd mile servant leadership on the culture at Chick-Fil-A that explains my experience.  “Chick-fil-A employees have helped Chick-fil-A become just as known for its “Second-Mile Service” and delivering the signature response of “It’s my pleasure” as it is for delicious chicken.  Every time an executive chooses to be last in line, or a restaurant staff member runs out in the rain to escort a mother and her children inside under an umbrella, Chick-fil-A founder Truett’s example of servant leadership lives on.”4  Dan Cathy, the President and CEO of Chick-Fil-A, puts it this way, “We make sure the first mile is taken care of,” noted Dan. “And then we go beyond that to the second mile. We provide hostesses, carry trays if necessary, have table tray liners. We’ve even gone so far as to change a tire for someone.”5  Changing tires and wiping up blueberry sludge—it all began with a culture of 2nd mile servant leadership.

Consider the impact 2nd mile servant leadership has on marketing and sales.  Donald Miller, a marketing consultant and author of Building a Storybrand, argues that a servant leadership culture in marketing leads to a paradigm shift whereby “the customer is the hero of our brand’s story, not us.  When we position our customer as the hero and ourselves as their guide, we will be recognized as a sought-after character to help them along their journey.  In other words, your audience is Luke Skywalker. You get to be Yoda.”6 Servant leaders are guides, not heroes. You still compete, but you compete at becoming the best possible guide you can be.  The goal is to guide your customer to be wildly successful. They are the hero. You are the guide.

Servant leaders, as Andy Stanley states, ask one key question over and over again, “How can I help?”  They are, as he states, essentially saying, “How can I leverage me for you?” This principle of 2nd mile servant leadership is so impactful that Andy Stanley calls it “the most powerful, the most transformational, the most inspirational leadership principle on the planet.”  He goes on to say, “you can lead without it, but you will not be a leader worth following without it.”7


Only one more word to explore.  Leadership. Some of you may not think of yourself as a leader.  Jesus thinks of you differently. He made you in His image (Genesis 1:27) and He has invited you to take dominion over the earth (Genesis 1:28).  Think about who Jesus chose as leaders. Jesus chose people who wouldn’t have necessarily been tabbed as leaders in the first century. He chose the hated tax collectors, the smelly fishermen, and the average Joe to lead the greatest movement the world has ever known.

Jesus seemed to believe ordinary people can be leaders.  Why is that? Because ordinary people have influence, and “leadership is influence, nothing more, nothing less,” writes John Maxwell.8   All of us have some level of influence, whether that is in our home, in our sphere of work, in our rec league, and in the ordinary things we do in life.  The question then becomes how we lead by leveraging our influence. As we’ve seen today, Jesus is calling us to leverage our influence to serve others around us in a way that shatters expectations.  Our service doesn’t end with contractual obligations (the first mile); our service goes over and above what is required (by going the 2nd mile).  No task is too low; no person is too unimportant.  We simply serve, with a humble confidence, as “servants of all” (Mark 9:35).  We’re unflinchingly committed to leveraging the influence we have been given for the flourishing of friends, enemies, colleagues, neighbors, and family members.


The challenge of 2nd mile servant leadership is actually far more daunting than climbing El Capitan in Yosemite without a rope.  Some of you may have seen the documentary Free Solo, which features Alex Honnold’s death-defying free solo climb.  Alex scaled a 3,000 foot vertical face featuring wicked overhangs, giant cracks, and smooth sections of slipperiness that mimicked an ice-skating rink. To date, no one besides Alex Honnold has been capable of conquering El Capitan without a rope.

Similarly, only one man ever climbed the mountain of 2nd mile servant leadership without falling off (hint, it was the same man who issued the challenge, from the top of the Mount).  Jesus, you guessed it. As the greatest servant leader in all of human history, Jesus leveraged His unrivaled heavenly influence and chose to make “Himself nothing, taking the very nature of a servant” (Philippians 2:7).  In so many ways, He took up the towel and basin and served. In doing so, He met the expectations God has for all of us in the first mile of His earthly life.  Then He went the second mile. The burden He carried on His 2nd mile was far heavier than any burden any we are asked to carry in ours and it took more than a few hours.  He had to carry the burden of our sin. His 2nd mile was filled with whips, a crown of thorns, spikes, the wrath of God, separation from God, and a descent into the pit of hell itself, enduring all that Satan and his comrades could throw at Him.

Then Easter happened.  Hope leapt out of the grave.  Things changed. Ordinary people, like the disciples, fresh off of arguing about being the greatest, willingly became servants, all unto death.  The book of Acts documents how the early church began to carry out this principle over and over and over again (see Acts 2:42-47; Acts 4: 32-37).  They served across racial lines, class lines, and every imaginable barrier. They served Christians and non-Christians alike. When the plagues struck, the Romans expelled the sick into the street to preserve their own lives; Christians, on the other hand, went the 2nd mile and took the sick into their homes and either nursed them back to health or went to their grave with them. Dionysius, writing in the 1st century, states, “Many in nursing and curing others, have transferred their death to themselves and died in their stead…The heathen behaved the opposite way…they pushed the sufferers away and fled from their dearest, throwing them into the road before they were dead.”9

The church literally exploded through 2nd mile service.  Rodney Starks, a sociologist, notes the church went from 12 disciples to comprising 56.5% of the population and 33, 882,008 people.10

In conclusion, while the disciples struggled mightily to carry out the principle of 2nd mile servant leadership before the Resurrection, there was a decided shift after the Resurrection.  Like them, we won’t carry it out perfectly, but if we grasp on again and again and again, by faith, to the Great Servant Leader himself, we too can go the 2nd mile.  And when we do, look out!


Discussion Questions

  1. Read Matthew 5:41.  Discuss 2nd mile servant leadership in the 1st What were Jews required to do to meet Roman laws/expectations?
  2. Why did Jesus call them to go the 2nd mile?  What happens in the 2nd mile?
  3. Read Luke 9:46-48; Luke 22:24-26; Mark 10:35-45.  Discuss your thoughts about these passages.
  4. Discuss how 2nd mile servant leadership impacts a business? A home? A church?
  5. Leadership is influence.  Discuss how you can leverage your influence for the sake of others.  What does that look like?
  6. Describe how the Resurrection brings hope for 2nd mile servant leadership.
  7. What is the thing you were most impacted by in today’s training session?

Going Deeper (Suggestions by Author & Pastor Rankin Wilbourne)











[9] Anne??








Stephen Phelan is a beloved son of God, husband to Bradford, dad of 4, crazy about his family in Alabama and former church family in San Diego, pastor of a mortgage company (what???), and joyfully astonished by the grace of God and the power of the Spirit.

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