In Part 1, we examined the essentials of hiring, beginning with self-awareness and creating a team that matches your company’s culture and tempo. However, as your business expands, the stakes become higher. Hiring entry-level and mid-level workers is one thing; assembling your leadership team presents an entirely different challenge. These individuals will shape your company’s future, influence its culture, and decide whether your growth is steady or chaotic.
Executive-level recruitment is more than just hiring—it’s a strategic alliance. The wrong leader can undo years of progress, fracture the culture, and cost much more than their salary. The right one acts as a force multiplier, boosting your vision and addressing gaps you weren’t even aware of.
Why Leadership Hiring Is Different
When you’re hiring for your leadership team, you’re not just assessing skills and experience. You’re also evaluating strategic thinking, decision-making under pressure, and the ability to lead others through uncertainty. These individuals need to operate with minimal oversight—they’re the adults you trust to manage critical parts of your business while you focus on the larger vision.
At the executive level, cultural fit becomes even more essential. A VP or director doesn’t just operate within your culture; they actively influence it. They set the tone for their departments, demonstrate the behaviors you want to see, and either strengthen or weaken your company’s values through their daily actions. One misaligned leader can cause ripples that impact morale, productivity, and retention across entire teams.
Structure Before Hiring
Before recruiting executives, clarify your organizational structure. Many growing companies hire senior leaders reactively —when someone leaves or workloads become unmanageable —and rush to fill the gap. This often results in overlapping responsibilities, unclear authority, and frustration everywhere.
Take time to plan your leadership structure now and in two years. Which functions require dedicated executive oversight? Where are the essential gaps in your current team? What additional skills does your leadership team need?
This clarity serves two purposes: it helps you identify exactly who you need, and it provides candidates with a clear understanding of where they fit and how they can make an impact. Top executives want to know they’re stepping into a well-defined role with full authority and clear expectations, not a chaotic situation where they’ll spend months just figuring out their mandate.
Look for Complementary Strengths
When assembling a leadership team, avoid the temptation to hire people who think exactly like you. Yes, shared values and vision are important, but you also need leaders who bring different perspectives and strengths to the table.
If you’re a big-picture visionary, you need detail-focused operators who can transform strategy into actionable plans. If you excel in chaos and move quickly, bring in leaders who can develop systems and processes that support growth. The best leadership teams have creative tension, people who challenge each other’s thinking while staying aligned on the ultimate mission.
This is where honest self-assessment becomes essential again. What are your blind spots? Where do you lose interest or energy? Those are precisely the areas where you need strong executive leadership to supplement your approach.
The Interview Process for Executives
Executive hiring demands a different interview approach. Beyond evaluating competency, you’re trying to understand how someone leads, handles adversity, and whether they can operate with the autonomy your business needs.
Ask about specific situations: How did they handle a major failure? When have they had to make an unpopular decision? How do they build and develop their own teams? What’s their approach when they inherit underperforming talent? These questions reveal character, judgment, and leadership philosophy in ways that hypothetical questions never will.
I also believe in having extended conversations over several meetings. Leadership chemistry is essential. You need to observe how someone thinks through complex problems, how they handle pushbacks, and whether the relationship can withstand the pressure that naturally comes with growth.
Autonomy with Alignment
Once you hire executives, grant them full authority. Nothing is more discouraging for a senior leader than being second-guessed on every decision or constantly needing approval. We hire adults who can take initiative, solve complex problems, and own their areas.
That said, autonomy doesn’t mean isolation. Your leadership team should function as precisely that—a team. Regular strategy sessions, open communication about challenges, and precise alignment on company priorities ensure everyone is working toward the same goals, even as they operate independently within their areas.
Clearly define decision rights, financial authority, and involvement points. This helps prevent frustration and ensures the autonomy you give doesn’t lead to chaos or misalignment.
Investing in Leadership Development
Building a leadership team isn’t a one-time event; it’s an ongoing investment. Even the best executives have areas for growth, and markets change, requiring new skills and approaches. Make room for your leadership team to develop—whether through formal training, peer learning, or simply giving them time to think strategically instead of constantly firefighting.
The Multiplier Effect
A strong leadership team creates exponential value. They don’t just handle their own responsibilities; they develop other leaders, improve systems, and solve problems before they reach your desk. They give you the bandwidth to focus on strategy, relationships, and the next phase of growth rather than getting pulled into operational details.
But more than that, the right leadership team creates momentum. When talented people see strong leaders above them, they want to stay and grow. When clients and partners interact with competent, empowered executives, trust builds quickly. When you’re not the bottleneck for every major decision, the entire company moves faster.
Building your leadership team is perhaps the most valuable investment you’ll make as your business grows. Take the time to do it right, empower them to lead, and observe your business transform in ways you couldn’t achieve alone.