Kris Duggan: 7 Books Every First-Time CEO Should Read Before Hiring a VP

Hiring a VP is one of the most consequential decisions a first-time CEO will make. This person will shape key departments, influence culture, and represent the company’s leadership both internally and externally. Getting it right requires more than good instincts. According to Kris Duggan, author of Business Gamification For Dummies, “Founders should pause before hiring and do something often overlooked – read.”

Duggan has worked with dozens of early-stage companies. He’s seen how a thoughtful reading list can prepare founders to evaluate candidates more critically, set expectations clearly, and avoid common mistakes. 

He recommends checking out these seven books, which offer practical guidance on leadership, hiring, and team dynamics—insights that are hard to absorb mid-crisis or after the wrong person is already in place.

1. The Hard Thing About Hard Things by Ben Horowitz

This book doesn’t romanticize startup leadership. Horowitz writes candidly about the mental strain, tough calls, and lonely moments that come with being a CEO. For founders about to hire a VP, it’s a reality check.

One key idea is that leadership isn’t about avoiding problems—it’s about handling them when everything goes wrong. CEOs who internalize that will look for VPs who have managed through failure, not just scale. The book also emphasizes the value of decisiveness and communication under stress—traits that don’t always show up in a résumé.

That mindset is especially relevant in light of data from Exploding Topics, which shows that up to 90% of startups fail, with 10% failing in the first year and nearly 70% between years two and five. These are often the stages when leadership mistakes become most visible. Horowitz’s insights help CEOs recognize the kind of resilience and clarity they should be hiring for—especially as early-stage challenges turn into operational complexity.

2. High Output Management by Andrew Grove

Andy Grove’s classic is a manual for how management actually works. He breaks down systems, processes, and performance in a way that’s both analytical and applicable to any team size.

For CEOs hiring a VP, Grove’s concept of “task-relevant maturity” is especially helpful. It encourages evaluating whether a candidate can succeed in this role, at this stage—not just whether they’ve held the title elsewhere. The book also reinforces the importance of measuring output clearly and frequently, helping CEOs establish structure with new executives from day one.

3. Who: The A Method for Hiring by Geoff Smart and Randy Street

Who is a practical guide to building a repeatable hiring process. It introduces a structured method that starts with a “scorecard”—a document that defines what success looks like in the role. This approach helps founders shift from hiring on gut feel to evaluating candidates based on outcomes and capabilities.

The book also includes a specific interview format designed to uncover patterns in behavior and decision-making. For first-time CEOs, this process prevents common traps like overvaluing charisma or vague claims of experience. And it’s worth the effort—according to the U.S. Department of Labor, a bad hire can cost up to 30% of that employee’s first-year earnings. Some estimates go much higher, ranging from $240,000 to $850,000 per employee when accounting for lost productivity, team disruption, and recruiting costs.

4. First, Break All the Rules by Marcus Buckingham and Curt Coffman

Based on Gallup research, this book challenges traditional assumptions about what makes a good manager. It argues that effective leadership comes from focusing on people’s strengths, not fixing weaknesses.

For CEOs hiring a VP, this insight matters. Too often, founders look for a “well-rounded” candidate, when what they need is someone with sharp skills in key areas. The book also helps readers identify signs of strong management—like creating clarity for teams and encouraging accountability—which are essential in early-stage companies.

5. The Five Dysfunctions of a Team by Patrick Lencioni

Lencioni’s book is built around a simple model: trust, conflict, commitment, accountability, and results. It explores how even high-performing individuals can create dysfunction when placed in the wrong environment—or when misaligned with others.

First-time CEOs often overlook how much influence a VP can have on team cohesion. This book teaches how to spot behavioral red flags, how to build alignment early, and how to avoid bringing in someone who prioritizes personal wins over team success.

6. Measure What Matters by John Doerr

Doerr’s book introduces OKRs (Objectives and Key Results), a goal-setting framework used by companies like Google. It’s not just a tool for scaling—OKRs force leaders to articulate what success looks like and track progress rigorously.

When hiring a VP, OKRs offer more than structure. They create accountability. CEOs who understand this framework can better evaluate whether a VP candidate thinks in outcomes or activities. It also helps avoid mismatched expectations down the line.

7. Radical Candor by Kim Scott

Scott’s book explores how to build strong working relationships while maintaining direct, honest feedback. It’s especially useful for founders transitioning from being “one of the team” to managing other leaders.

Hiring a VP changes a company’s internal dynamics. This book teaches CEOs how to challenge directly while still showing care—a balance that prevents resentment, confusion, or disengagement. It also sets a clear expectation for how feedback should flow in both directions.

How These Books Work Together

Individually, each book offers a focused perspective—on hiring, managing, goal-setting, or communication. Together, says Kris Duggan, they build a cohesive mental framework that helps first-time CEOs approach VP hiring with clarity and confidence. Instead of relying on instinct or advice from peers, founders who read across these areas gain structured ways to evaluate candidates and think critically about what their company truly needs.

The combination of strategy, operations, people management, and culture gives CEOs a more complete view of what makes leadership effective. Horowitz’s and Grove’s books cover decision-making and execution. Smart and Buckingham focus on how to assess people. Lencioni and Scott address interpersonal dynamics and team health. Doerr closes the loop by tying performance to measurable outcomes. None of these topics stand alone in a functioning organization—they influence each other every day.

First-time CEOs can’t afford to specialize too narrowly. The best hires operate well across disciplines and bring balance to a leadership team. These books help founders understand how to identify and support people who can work across those boundaries. They also help CEOs articulate their own leadership style and build a structure around it, rather than assuming others will just adapt. For a real-world perspective on how to apply these principles, Thumbtack CEO Marco Zappacosta’s advice on assembling an executive leadership team offers grounded insights on building a cohesive, high-performing team from the ground up.

The ultimate benefit is intentionality. CEOs who think through these dimensions aren’t just trying to “fill a gap.” They’re building the leadership core of the company. A VP hired through that lens isn’t just another team member—they’re a partner in building something sustainable.

Hiring a VP Is a Craft, Not a Checklist

Too often, early-stage hiring gets reduced to urgency. A team is growing fast, responsibilities are piling up, and the CEO is stretched thin. The instinct is to hand things off to someone “senior.” But leadership roles are too important to fill based on pressure alone.

Each of these books adds structure, perspective, and depth to a decision that deserves careful consideration. Reading them doesn’t make someone an expert, but it raises the floor. It makes conversations with candidates sharper, evaluations more objective, and onboarding more thoughtful. It also helps prevent problems before they start—misaligned priorities, fuzzy responsibilities, or vague definitions of success.

The stakes couldn’t be higher. While around 90% of startups fail, only 1.5% of those that survive achieve an exit of $50 million or more within the top eight U.S. startup ecosystems, according to Startup Genome. That means every leadership decision—including who you bring in as VP—can have outsized consequences for your company’s future.

For any founder preparing to hire their first VP, the best advice is to slow down and learn before acting. Read with purpose. Reflect on what your company actually needs—not just what looks good on paper. Then build a hiring process that matches that intention.

Hiring a VP isn’t just about filling a seat. It’s about building a company that works when you’re not in every meeting, solving every problem. As Kris Duggan says, “That starts with choosing the right person—and knowing why they’re the right fit.”