What makes teams actually healthy over the long haul?

In this conversation with Brian Cromer, we talk about the fundamentals that never stop mattering: caring for people before correcting them, giving the "gift of clarity" (not just big vision), and building cultures where people feel heard and own the mission.

Brian also opens up about navigating "church hurt" without becoming bitter, and the work he's done to grow in empathy and keep his heart soft.

01:00:00 Intro - food talk and skyline chili
01:01:41 Longevity in friendship - why it matters more now
01:04:38 Building healthy teams - care as the first leadership test
01:06:36 "Do leaders really care?" - leading with care in non-church workplaces
01:10:26 The gift of clarity - clear vision vs big vision
01:13:48 Competency vs character - integrity of heart and skill of hand
01:18:22 Vision and execution - systems that deliver vision
01:23:04 Conviction and unity - how to know vision is clear
01:24:15 Meetings and perspective - the water bottle metaphor
01:30:36 Leadership duality - pastor, boss, friend and family culture
01:32:07 "Hat on, hat off" - clarity down and maturity up
01:41:37 Church hurt and heart health - staying soft
01:44:45 Hurt by people, not the church - empathy and grace
01:49:42 Sanctification and grace - leaving room for people's process
01:52:31 Wrap-up and gratitude

About Sidecar Leader:

Sidecar Leader is committed to helping church leaders move further, faster - without going alone.

Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose.

Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more at sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader

If you've got a lot of options in front of you right now and the emotions are high… this episode is for you.

In this early-2026 conversation, we talk about the difference between vision decisions and emotional decisions - and why leaders often get stuck when the water gets muddy. Then we walk through five questions to clarify vision and five principles to communicate it in a way that people can run with.

You'll leave with a framework you can use immediately for your church, business, nonprofit, or team - so you're not just doing more this year… you're doing the right things.

Key:
The clearer the vision, the fewer the options, the easier the decisions.

CHAPTERS

01:00:03 Favorite gift + 2026 hiking talk
01:01:01 Coaching call: high emotions, too many options
01:01:39 Vision decisions vs emotional decisions
01:02:08 "Go to the mountain" - but bring a framework
01:03:14 Without vision, people cast off restraint
01:04:59 Vision must be clear and portable for people to run with it
01:06:28 Practical framework: 5 vision questions + 5 communication principles
01:06:45 Sidecar masterclass ad
01:07:12 Question 1: what are we moving people toward?
01:12:47 Question 2: why this matters most + saying no
01:13:15 Unprioritized vision becomes exhaustion
01:14:13 Sidecar coaching ad
01:14:46 Question 3: can you repeat this all year?
01:17:12 Question 4: what changes because of this vision?
01:20:47 Question 5: who are we becoming?
01:22:27 Sidecar team coaching ad
01:23:22 Static buzz + transition
01:23:28 Bonus: "prophetic vision" = divine guidance, not copying others
01:29:48 Communicating vision principle 1: clarity of purpose
01:30:09 Principle 2: one breath vision + clear over clever
01:30:42 Sidecar planning off-site ad
01:31:37 Principle 3: vision leaks, repetition matters
01:34:53 Principle 4: people need a role in the vision
01:38:52 Principle 5: vision is formation, not just construction

ABOUT SIDECAR LEADER

Sidecar Leader is committed to helping church leaders move further, faster - without going alone.

Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose.

Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more: sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader

Excellence is more than polished services and clean environments – it's a spirit that permeates everything you do as a leader. In this Sidecar Leader conversation, Pastor Jason unpacks a biblical and practical vision for excellence in both church and organizational life. Drawing from the story of Solomon and the Queen of Sheba, he paints a picture of excellence that literally "takes people's breath away" – not for our glory, but to honor God and serve people well.

00:00 – Why excellence is always on our mind
01:39 – Excellence that takes your breath away
04:57 – Excellence vs perfectionism & consistency
07:18 – Excellence that honors God & inspires people
10:21 – Presence, details & setting the table
12:42 – Leading your team toward excellence
15:21 – Fresh eyes, feedback & staying a learner
19:27 – Modeling what you want multiplied
23:30 – Pursuing excellence without crushing your team
27:31 – Equipping through the dip & developing leaders
32:52 – Excellence, creativity & effectiveness

About Sidecar Leader:

Sidecar Leader is committed to helping church leaders move further, faster—without going alone. Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose. Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more at sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader

In this conversation, Jason sits down with Beth, a longtime kids and next gen leader at Church of the Highlands, to unpack how you build a thriving kids ministry that actually recruits, retains, and disciples volunteers and families.

Beth shares how she went from music major and worship leader to executive assistant, then into leading Highlands Kids across multiple campuses—without a traditional kids ministry résumé. She talks about why Pastor Chris chose her anyway, why "heart of the house" beats past experience, and how one small group called "Baby Praise" changed the trajectory of her calling.

They dig into the real challenges of recruiting kids volunteers, how Highlands built a team of nearly 5,000 kids Dream Teamers, the power of story-based vision casting, and why students are your secret weapon. Beth also unpacks what she's learning about Gen Alpha, why questions are central to discipleship, and how Highlands redesigned kids ministry around circles and conversation instead of just content.

Finally, Beth speaks directly to leaders—especially women—about walking into male-dominated rooms with confidence and humility, dealing with insecurity and pride as "two sides of the same coin," and what she's most excited about in this new season of life and ministry.

0:00 – Worship Leader to Executive Assistant: Beth's Ministry Journey
4:30 – From Baby Praise to Leading Highlands Kids Across 12 Campuses
9:30 – Heart of the House vs. Experience: Why She Got the Role
13:30 – Recruiting with Confidence, Not Desperation (and 5,000 Kids Volunteers)
18:30 – Students as a Secret Weapon in Kids Ministry
23:30 – Building Healthy Volunteer Rhythms, Belonging, and "HK for Life"
28:30 – Understanding Gen Alpha: Questions, Authenticity, and Circles
35:30 – Training Leaders to Handle Hard Questions and Say "I Don't Know"
41:00 – Confidence, Humility, Pride vs. Insecurity, and Walking into Any Room
46:30 – What to Prioritize in a New Kids Ministry and Beth's Vision for Her Next Season

About Sidecar Leader:

Sidecar Leader is committed to helping church leaders move further, faster—without going alone. Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose. Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more at sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader

Most organizations don't have a vision problem—they have an execution problem. In this conversation we unpack why consistency beats creativity, the real cost of poor follow-through, and the practical tools leaders can use to close the gap between ideas and implementation: ownership, roadmapping, time-blocking, check-ins, and the "eat the frog" principle. If you feel stuck, this one's for you.

00:00 – Cold open & today's topic (execution isn't sexy—it's essential)
01:00 – Why consistency beats creativity for great leadership
02:32 – The "executor" pastor: seven years of small, focused steps
06:33 – Vision isn't the problem; follow-through is
08:22 – Ad Spot: Essentials Leadership Masterclass (7 skills you can use now)
09:18 – The real costs of poor execution: frustration, credibility, missed windows, waste, stuck 13:35 – Ad Spot: Sidecar Coaching (clarity, objectivity, accountability)
14:14 – Why teams lack execution: urgent vs important, "do the work," pain of staying the same 18:13 – Decision-making vs implementation: arranged-marriage lesson (maintain the decision) 22:55 – Tools that close the gap: eat the frog, ownership & buy-in, roadmaps, time-blocking, check-ins

About Sidecar Leader: Sidecar Leader is committed to helping church leaders move further, faster—without going alone. Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose. Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more at sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader

Australian church planter Chris Carmona shares the gritty, unfiltered path of planting in Chicago—fast growth, painful pruning, pandemic shutdowns, losing a house two days before Christmas, a cancer diagnosis, and the revelation that changed his leadership: stop trying to attract people, start attracting God. We unpack culture vs. charisma, hiring fast vs. building people, leading without fear of loss, and his scrappy "use what you have to get what you need" launch play that traded AV upgrades for free rent. It's a masterclass in resilient leadership, healthy culture, and long-game faith.

Topics: church planting in a hard city, culture shaping, confronting with courage, building people, StrengthsFinder, resilience through crisis, scrappy creativity, leading without fear of loss.

01:00:00 - Intro & "you've walked through hell…still life-giving"
01:00:38 - Effort vs. God's timing, humility after early "wins"
01:04:00 - Fasting & the pit-bull resolve ("Even if this takes me to my destruction…")
01:05:59 - Breakthrough year → motive check → pandemic shuts it down
01:07:14 - Ad Break: Essentials Leadership Masterclass
01:08:49 - Attract God, not people → leading without fear of loss
01:10:17 - Pandemic fallout, house lien, cancer diagnosis & a promise
01:14:09 - Ad Break: 1:1 Leadership Coaching
01:14:57 - Culture > comfort: confront, build people, Strengths Finder mapping
01:30:00 - "Use what you have to get what you need" ($50k launch hack) + wrap

About Sidecar Leader: Sidecar Leader is committed to helping church leaders move further, faster—without going alone. Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose. Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more at sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader

Seasons determine seasons. In this candid conversation, our guest (a senior pastor and church planter) unpacks the real tensions of transition—shifting from staff to lead pastor, inviting your leaders into the process, and walking out integrity when timelines and decisions don't go your way. We talk honesty and honor, calling vs. ambition, counting the cost for your family, and how senior leaders can send people with love without sacrificing mission.

Along the way: the difference between Great Commission urgency and Great Commandment love, why "slow is wise" at the turn, and practical scripts for hard conversations—whether you're the youth pastor sensing a new assignment or the senior pastor shepherding someone out.

00:03 Seasons shape seasons: integrity in transition
01:20 Staff → Lead pastor: invite your pastor in
03:52 Slow at the turn: discernment over speed
08:16 Honor ≠ agreement; honesty + honor
11:03 Coaching someone sensing a move; calling vs. timing
14:01 When leadership disagrees: clarity, cost, and family
21:55 Senior pastor lens: Great Commission and Great Commandment
28:26 Father & stewardship lens; sending well and staying open-handed
33:19 Reconciliation over time, own your part, model Jesus & close

About Sidecar Leader: Sidecar Leader is committed to helping church leaders move further, faster—without going alone. Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose. Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more at sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader

Respectful debate sharpens leaders. In this episode, we unpack how to argue with honor, why truth + love increases impact, and a simple lens for diagnosing problems: spiritual, practical, or clinical. We pull from early church debates, coaching calls, spans of care, and the Jethro Principle—then land on a usable one-on-one framework (the 4Cs: Care, Cover, Correct, Communicate) you can apply this week. If you lead people (church or marketplace), this is a toolkit episode.

00:00 – Why respectful debate matters
05:35 – Peter vs. Paul: correction with honor
10:40 – Spiritual vs. Practical vs. Clinical
17:25 – Early church on responsibility
22:05 – Medicine, miracles & outcomes
27:30 – Diagnosing org problems (S/P/C)
33:50 – The 4Cs one-on-ones
41:05 – Belonging → engagement → performance
48:20 – Spans of care & Jethro Principle
55:20 – Structure vs. "robotic" leadership

About Sidecar Leader:

Sidecar Leader is committed to helping church leaders move further, faster—without going alone. Through strategic coaching, creative services, and a proven three-phase process (Discover, Design, Deliver), Sidecar partners with pastors and leadership teams to clarify their vision, overcome challenges, and execute with purpose. Whether you're scaling your church, shifting your strategy, or simply need clarity in your next step, Sidecar helps you lead with confidence.

Learn more at sidecarleader.com
Contact: info@sidecarleader.com
Follow on Instagram: @sidecarleader