Serve Up, Coach Down

When you’re stuck between a demanding boss above and a team of employees below, how can you lead effectively without losing your sanity or your power? In Serve Up, Coach Down, Nathan Jamail argues that the most misunderstood and undervalued position in any organization—the leader in the middle—holds the greatest influence. He insists that leadership success doesn’t come from commanding authority or hiding behind helplessness—it comes from serving up to your bosses and coaching down to your people. These two intertwined disciplines form the core of Jamail’s leadership philosophy.

Jamail contends that the traditional idea of “servant leadership,” while noble, is misapplied. Leaders in the middle too often misunderstand “serving” as catering downwards to employees and protecting them from management decisions. In reality, true leadership strength lies in serving upward—making your boss look good, implementing the company’s direction wholeheartedly, and taking ownership of results—and coaching downward—developing, challenging, and holding your people accountable so they achieve more than they thought possible.

The Leader in the Middle: A Unique Power Position

According to Jamail, “leaders in the middle” include everyone who leads others while reporting to someone else—managers, directors, vice presidents, team leads, and anyone “sandwiched” within an organizational hierarchy. Far from being powerless middle managers, these individuals are the linchpins of organizational performance. They’re both translators and transformers—turning vision from the top into action at the bottom. But to do that effectively, they must avoid two traps: defending up (arguing with or resisting their boss) and protecting down (shielding employees from accountability or change). The alternative? A bold mindset shift toward accountability, humility, and commitment.

Serving Up vs. Sucking Up

One of Jamail’s central lessons is that serving up is not sucking up. To illustrate, he recounts a corporate meeting where a regional VP’s microphone fails mid-presentation. One director rushes to fix it; another mocks him as a “suck-up.” Yet Jamail reveals that the director wasn’t currying favor—he was serving up. He saw his role as making his boss look good and keeping the company mission on track. The difference between sucking up and serving up is intent: sucking up is selfish manipulation to gain attention, while serving up is selfless support driven by belief in leadership and the organization’s direction.

This section establishes one of Jamail’s recurring mantras: belief without proof. As a leader in the middle, you won’t always understand every decision from above. You may think you’re right, but your job isn’t to be right—it’s to execute the direction with conviction, even amidst uncertainty. Leaders who constantly challenge their bosses for validation cripple both themselves and their teams.

Coaching Down, Not Managing

Serving up is only half the story. The other half is coaching down, which Jamail differentiates sharply from managing. Managing, he argues, controls behavior after the fact; coaching builds skill and accountability before results are measured. Too many managers simply give feedback after something goes wrong, like armchair quarterbacks dissecting a game after the final whistle. Coaching, by contrast, means scrimmaging with your team—practicing scenarios, role-playing conversations, and demanding daily improvement through preparation. It’s active, not reactive.

Coaching down also redefines accountability. It’s not about punishment or micromanagement. It’s about belief: “I believe you can do better, so I’m holding you to that.” Leaders in the middle who coach down this way create what Jamail calls “high-intensity environments”—cultures fueled by energy, clarity, and performance—rather than “high-tension environments” plagued by stress and fear.

Creating Certainty in Uncertain Times

In a fast-changing business world, organizations face constant shifts—new technology, leadership transitions, or restructuring. Jamail shows that leaders in the middle are uniquely positioned to bring stability through belief and execution. Instead of obsessing over the “what” and “why” of change, they focus on the “how.” He uses vivid workplace examples—like a leadership transition or centralization initiative—to demonstrate how belief-driven middle leaders can keep teams aligned and moving forward even amid uncertainty. His recurring metaphor of driving into the “lake” from your GPS—trusting direction even when you doubt it—captures this ethos perfectly. Sometimes you have to “drive into the lake,” metaphorically speaking, because commitment and curiosity outperform skepticism every time.

Owning the Power in the Middle

Ultimately, Jamail believes that power isn’t given—it’s claimed. Middle leaders often feel powerless because they give their power away through blame, excuses, and ego. True leadership comes from owning the direction you’re given and inspiring your team to execute at the highest level. That means dropping the “us versus them” mentality between employees and management. There’s no “they” in great organizations—only “us.”

The book concludes by urging leaders to avoid complacency and commitment fatigue. Great leaders keep learning, reading, and growing (“Leaders are readers,” Jamail jokes), because personal growth fuels your ability to coach and serve others. He closes with a simple but transformative challenge: make serving up and coaching down your default daily mindset. By doing that, you’ll transform not only your own leadership but your organization’s culture from the middle out.

Serving up means embracing humility and total accountability to your boss and organization—a radical approach that requires conviction even when you don’t agree or understand. Jamail’s first case study, Steve, a director overseeing rehabilitation centers, demonstrates how defending up destroys credibility. When Steve lost a manager, he complained to his boss that the workload was impossible. He hadn’t restructured, trusted, or empowered his team—he simply protected them. Jamail advised him bluntly: “If I were your boss, I’d replace you.” Steve was defending up, not serving up.

Over time, Steve changed course. By demanding more from his managers instead of shielding them, he improved results without adding staff. He learned the essence of serving up: believe first, question to understand, and own execution. When you disagree, the right question isn’t “Why?” but “How would you like me to make this happen?”

Sucking Up, Defending Up, and Serving Up

Jamail distinguishes three leadership patterns:

• Sucking Up: Acting for selfish gain—flattery without belief. It’s manipulation dressed as loyalty.
• Defending Up: Arguing to be right, often hiding fear of accountability behind pride or logic.
• Serving Up: Executing direction with humility, assuming positive intent, and committing to results.

Serving up is rooted in trust. Jamail likens it to following a GPS—you follow it faithfully even when the road looks wrong. In business, your boss and company are the GPS. You lead best by trusting the direction and executing fully, then providing upward feedback after you’ve owned the implementation.

Choosing How to Respond

Jamail provides three choices when faced with directions you dislike:

• If you align with the direction, deliver it better than anyone else.
• If you’re uncertain, seek clarity respectfully by asking “how” questions instead of “why.”
• If you can’t align morally or strategically, move on—don’t undermine from within.

In serving up, leaders accept that their perspectives are limited. Those above have broader visibility, even if imperfect. Belief doesn’t need proof; it needs commitment. As Jamail puts it, “Your power comes from owning direction, not questioning it.”

Beyond serving bosses, Jamail emphasizes the power of “serving across” (collaborating with peers) and “serving out” (serving customers). These principles tear down organizational silos, transforming fragmented departments into cohesive, mutually supportive systems. Jamail describes a client company that began holding cross-departmental meetings dedicated not to sharing grievances but to asking, “What can we do to serve you better?” This simple shift—focused on giving rather than receiving—transformed the workplace culture into one where, as the CEO later said, “Our departments try to out-serve each other.”

Serving Across: Partnering with Peers

One standout example involves Ken, a sales leader frustrated with the design team. He accused them of delays and inflexibility, while they blamed his salespeople for sloppy orders. Jamail challenged Ken to “clean his side of the street first” and ask the designers what his team could do better. That conversation opened mutual respect and cooperation, flipping conflict into partnership. The moral is simple: serving across breaks the illusion of competition between peers and replaces it with shared accountability.

Serving Out: From Customer Service to Customer Servant

Great leaders, Jamail argues, don’t just teach customer service—they model customer servanthood. When you treat customers like honored guests in your home, giving them your best even when they’re unpleasant, they sense sincerity and return loyalty. As he writes, “Don’t let the reactions of others determine your servant actions.” The mantra is “ABS: Always Be Serving.”

True customer-centricity, Jamail suggests, springs from leaders who model servanthood inwardly. When teams see their manager serving peers and bosses selflessly, they naturally replicate that behavior outward to customers. Serving up, across, and out, therefore, forms a full-circle culture of value creation inside and outside the organization.

If serving up is about humility and execution, coaching down is about development and belief. Jamail dedicates significant focus to this concept, arguing that most companies train but don’t actually coach. Training, he explains, teaches new information; coaching develops mastery through repetition and feedback. And real coaches don’t just observe—they practice with their people.

From Managing to Coaching

Jamail contrasts typical managers, who rely on post-mortem feedback, with coaches, who prepare and scrimmage. A manager watches an employee interact with a customer and discusses it afterward. A coach revisits it the next day, rehearses new approaches, and builds confidence for the next encounter. Coaching is ongoing, not episodic. It converts feedback into preparation. Leaders who claim they lack time to coach reveal a tragic irony—they expect employees to care deeply about the business while failing to show care for their development.

Creating a Thriving Culture

Great coaching cultures, Jamail suggests, mirror strong sports teams. He cites Chicago Cubs manager Joe Maddon, whose mix of accountability and quirky team traditions created an environment where players didn’t just survive—they thrived. In business, thriving cultures come from consistent coaching rhythms: one-on-one sessions, practice meetings, “floor days” where leaders walk the workspace, and scrimmages where staff rehearse difficult conversations or scenarios. This isn’t “froofy stuff”; it’s how professionals progress from good to great.

Coaching down demands high standards—like practice, repetition, communication, and constant personal growth. As Jamail puts it, “Great coaches are coachable.” If you stop learning, you stop coaching.

One of Jamail’s most practical insights is the danger of lowering expectations to maintain comfort. He recounts the story of Lynne, a regional VP who realized her longest-tenured employees wouldn’t meet the same standards she set for job applicants. Why? Because managers were afraid of holding them accountable—they might quit, and replacing them was inconvenient. Jamail calls this mindset a recipe for mediocrity.

Raising, Not Lowering, the Bar

In coaching environments, accountability isn’t punishment—it’s respect. Holding people to high standards communicates belief in their ability. Lowering goals, on the other hand, undermines both trust and power. As Jamail says, “Don’t lower goals to match results. Raise efforts to match goals.” He shows how leaders who loosen performance expectations for comfort sacrifice long-term growth for short-term harmony.

High-Intensity over High-Tension

In bridging what he calls the “knowledge gap”—the space between knowing and doing—Jamail introduces two cultural modes: high-tension (lots of pressure, no coaching) and high-intensity (high expectations plus coaching). Leaders who fail to coach create fear; leaders who coach create energy. When leaders refuse to accept excuses, invest time in development, and continually follow up, knowledge turns into sustained results. “Old habits die hard,” he admits, “but discipline is the bridge between learning and leading.”

One of Jamail’s favorite refrains is that time management isn’t a skill problem—it’s a will problem. Most time crises, he argues, are the result of poor priorities, not full calendars. His memorable analogy compares adults’ work management to high school students’ schedules: if teens can handle seven classes a day for years, professionals can manage their obligations. The issue is mindset.

Important vs. Urgent

Jamail revisits Stephen Covey’s timeless matrix—urgent vs. important—and points out that leaders consistently choose the urgent because it provides instant gratification. Putting out fires feels productive; coaching, planning, and serving up don’t give immediate rewards. But the longer you ignore important activities (like one-on-ones or customer updates), the bigger the fires you’ll face later. As he warns, “The longer the delay of consequence, the larger the impact.”

The Must-Do List

To fix this, Jamail proposes replacing to-do lists (filled with urgent tasks) with must-do lists—activities that drive long-term success: coaching sessions, development meetings, follow-ups with customers, time for learning, and reports that keep bosses informed. He outlines three essentials for success: Mindset (own your time), Discipline (schedule non-negotiably), and Execution (no excuses). Leaders who live by their must-do lists build accountability up and down their chains.

Jamail’s later sections confront a tough truth: leaders often confuse loyalty with tenure. Two stories drive this home. First, an engineer who bragged, “They need me,” after ten years on the job. In reality, he’d grown complacent and cynical. His presence demotivated the team until a new boss, refusing to tolerate entitlement, coached him to improve or move on. After leaving, both he and the team flourished. Second, Jamail contrasts leaders who cling to “loyalty” with those who redefine it as consistent contribution. True loyalty, he insists, is earned daily through excellence, not accumulated through years served.

Loyalty vs. Accountability

Leaders may hesitate to hold veterans accountable out of fear they’ll leave, but that’s misplaced compassion. Protecting underperformers disrespects high performers and erodes credibility. “Everyone is important,” Jamail writes, “but no one is required.” In this philosophy, appreciation and accountability coexist. Gratitude for past effort matters, but current impact matters more.

Sacrifice vs. Choice

In Chapter 22, Jamail reframes work-life balance as intentional choice, not sacrifice. His metaphor—a marriage renewed every five years—illustrates how serving up to one’s spouse or boss first doesn’t diminish love for others; it strengthens relationships built on continual, deliberate effort. True loyalty, whether to family or company, is proactive—not owed.

In the final chapters, Jamail reveals that the ultimate reward for serving up and coaching down is power—the authentic power that comes from ownership, not position. Middle managers often surrender this power by complaining about decisions or promoting “us versus them” thinking. He shares the story of his own boss who admitted, “I’m just a highly paid sales rep,” and immediately lost his team’s respect. The boss’s loss of belief made him powerless, even though nothing externally changed.

Ownership Without Ego

True power lies in executing direction like it’s your own. When communicating company initiatives, strong leaders replace phrases like “They want us to…” with “Here’s what we’re doing.” It’s subtle but transformative—it communicates collective ownership. Jamail likens this to a head coach and assistant coaches on a sports team: the assistants don’t undermine; they co-own the game plan. When middle leaders act like cogs, they become cogs. When they act like co-owners, everyone rises.

Eliminating Complacency

The book closes with a personal challenge to continuous growth. Jamail urges leaders to commit to lifelong self-development—reading, learning, exercising, and practicing gratitude. He warns against complacency, which masquerades as contentment but slowly kills performance. Being content, he writes, means feeling grateful yet still striving for better. “Complacency starts at the top,” he notes, “and trickles down to mediocrity.”

Keeping your power, Jamail concludes, means opening your doors—literally and figuratively. Let your boss attend your meetings. Invite transparency. Confidence doesn’t hide; it welcomes scrutiny. Real leaders aren’t threatened by oversight because they know who they are. “There is no ‘me versus the world,’” he writes, “only us, fighting to win together.”