Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, holds that nothing scales without a team you trust enough to challenge you. He explores this with Michael Cherney, co-founder and CEO of Cooler Logistics, who says asking for help and building a leadership team willing to push back produces faster, steadier growth than doing it solo, a principle he says shaped Cooler Logistics’ executive team, including COO Leigh Barnard, whom he credits directly for challenging his decisions.
Cherney spent 13 years scaling LoadDelivered Logistics before he stepped out to build his own company. Glenn Gow sat down with Cherney to find out what changes when a rising operator becomes the person responsible for everything.
This episode is for CEOs who are past the founding stage and starting to feel the strain of scaling communication, process, and their own leadership style at the same time.
Key Takeaways
- CEOs who try to manage a new office or division alone create their own biggest bottleneck. Cherney says his greatest opportunities for success came only after he learned to ask for help.
- Communication breaks down during scaling when roles are undefined, not just when values are unclear. Cooler Logistics builds clarity of role and clarity of objective into every leadership hire to prevent silos before they form.
- Process built too late costs a company its customer and employee experience. Cherney trains his team on new processes before they are fully needed rather than waiting until scale forces the issue.
- AI works as a force multiplier against operational bottlenecks like carrier sourcing, order entry, and documentation, but Cherney keeps human relationship-building central to Cooler Logistics’ service model instead of automating it away.
CEOs Prevent Communication Breakdown by Assigning Clear Roles
Michael Cherney, CEO of Cooler Logistics, ties most communication breakdowns during scaling to undefined roles, not unclear values. Silos form naturally as a company grows unless leaders intentionally build open, honest, and direct communication into how the team operates.
Cooler Logistics anchors that intent in named values: collaboration, leadership, integrity, metrics, and balance, applied to both internal and external relationships. Cherney says his leadership team knows exactly what their role requires and rarely needs him to mediate disagreements, because trust and clarity were built in from the start. “There’s clarity of role, clarity of objective,” Cherney says.
That clarity depends on hiring people willing to disagree with him. “I’m very fortunate my COO, Leigh Barnard, is that challenger every time,” Cherney says. He credits Barnard’s willingness to push back, alongside the rest of his executive team, with keeping Cooler Logistics’ decisions sharper than they would be with a team that simply agreed.
CEOs Build Process Before They Need It to Scale Without Cutting Corners
Michael Cherney holds a Lean Six Sigma Green Belt, and that training shows in how Cooler Logistics approaches process during growth. Rather than waiting for scale to force a process into existence, Cherney’s team builds and tests standard operating procedures ahead of time, then trains the whole company on them before they are strictly necessary.
“I’d rather err on the side of being over-prepared and training on something that we’re not actually doing yet,” Cherney says. He points to a previous fast-scaling stretch in his career, before Cooler Logistics, where cutting corners on process caused customer experience and employee experience to deteriorate. Building and training on SOPs early is how he avoids repeating that outcome.
Cherney is careful to separate discipline from rigidity. Processes still have to evolve as the business and its technology change, a continuous improvement mindset his Six Sigma background requires: keep checking whether a process is still efficient, and adjust it without abandoning what makes it work.
CEOs Use AI to Remove Bottlenecks Without Replacing Human Relationships
Michael Cherney treats AI as a tool for operational bottlenecks, not a replacement for the people who run Cooler Logistics. “AI is a force multiplier,” Cherney says, and in a service business like his, he adds that “human to human cannot be forgotten and it can’t be replaced.”
Cooler Logistics has deployed AI against three specific operational bottlenecks. Envoy AI, founded by Robert Nathan, helps the team identify the right carrier partner for a load, cutting the volume of purchasing calls needed to book freight from 100 calls for two loads down to 10 calls for 10 loads. Drumkit handles order entry and appointment scheduling, work Cherney describes as time-consuming and better suited to automation than to a person’s day. NABX manages paperwork, auditing, pricing, and documentation on the finance side.
Cherney draws a clear line around his own role in AI, positioning himself as a transportation provider who uses AI rather than one who builds it. The goal across all three tools is the same: remove the operational minutiae that consumes staff time so people can focus on relationship-building and revenue-generating work.
The Scaling Framework: What CEOs Can Take From Michael Cherney’s Playbook
| Principle | What it means in practice | Named evidence from this interview |
| Ask for help before you’re forced to | Treat requests for help as a leadership signal, not a weakness, especially the first time you run an office or team alone | Cherney’s greatest opportunities for success came only after he stopped trying to run LoadDelivered’s LA office by himself, a shift that shaped the executive team he later built at Cooler Logistics, including COO Leigh Barnard |
| Hire for clarity of role, not just cultural fit | Communication breakdowns during scaling trace back to undefined roles more often than unclear values, so define who owns what before conflict forces the question | Cooler Logistics’ role-clarity structure produces an executive team, led by COO Leigh Barnard, that surfaces disagreement directly with Cherney rather than letting it fester into the silos he saw form in less clearly defined teams |
| Build and train on process before you need it | Waiting until scale forces a process into existence risks the corner-cutting that erodes customer and employee experience, so train the team on SOPs ahead of the growth that will require them | Cherney’s Lean Six Sigma background led Cooler Logistics to test and train on SOPs early, a discipline he credits with avoiding the customer and employee experience decline he saw during a prior fast-scaling stretch |
| Deploy AI against bottlenecks, not against your people | Aim AI at operational bottlenecks like sourcing, entry, and documentation, freeing staff for the relationship-building AI cannot replace | Cooler Logistics uses Envoy AI to cut carrier-sourcing calls from 100 to 10 per ten loads booked, Drumkit for order entry and appointment scheduling, and NABX for documentation and pricing |
Quotes from This Episode
- “You can’t do it by yourself.” — Michael Cherney, Co-Founder and CEO, Cooler Logistics
- “I am a completely different person, leader and personally than I was day one.” — Michael Cherney, Co-Founder and CEO, Cooler Logistics
- “There’s clarity of role, clarity of objective.” — Michael Cherney, Co-Founder and CEO, Cooler Logistics
- “Human to human cannot be forgotten and it can’t be replaced.” — Michael Cherney, Co-Founder and CEO, Cooler Logistics
Frequently Asked Questions
How do CEOs build a leadership team that will challenge them instead of just agreeing?
Michael Cherney, CEO of Cooler Logistics, built his executive team around members who are given full clarity of role and permission to push back, including COO Leigh Barnard, whom he calls his most consistent challenger. When leaders trust each other enough to have healthy conflict, disagreements rarely need Cherney’s direct mediation, which he attributes to the intentional culture Cooler Logistics built from its earliest days.
How much process should a CEO build during a growth spurt?
Michael Cherney, a Lean Six Sigma Green Belt and CEO of Cooler Logistics, trains his team on standard operating procedures before the company actually needs them rather than waiting until growth forces the issue. He says this over-preparation protects customer and employee experience from the corner-cutting he saw during a previous fast-scaling stretch, while still allowing the company to evolve as long as it keeps its core tenets intact.
How can CEOs use AI to scale without losing the human side of their business?
Cherney treats AI as a force multiplier aimed at operational bottlenecks rather than a replacement for people. Cooler Logistics uses Envoy AI to cut carrier-sourcing calls, Drumkit to automate order entry and appointment scheduling, and NABX for documentation and pricing, freeing staff to spend more time on relationship-building and revenue-generating work that Cherney says AI cannot replace.
CEOs Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
