How to Identify Leadership Gaps as Your Company Scales

As a company grows, the demands on its leadership team shift. Strategies that work at the startup stage will often need to evolve as the team expands, operations become more complex, and new challenges emerge. One of the most important tasks for growing businesses is identifying leadership gaps before they hinder growth.

Today, we’re exploring how leadership needs change at different stages of growth, how to spot potential gaps in your executive team, and what strategies you can use to fill leadership gaps before they become larger issues.

Why Leadership Gaps Emerge as Companies Scale

If the skills or capacity of your current leadership team no longer align with the company’s needs, leadership gaps arise. As businesses scale, roles that were once filled by flexible, generalist leaders may require more specialized expertise. If companies fail to address these emerging leadership challenges as they scale, they risk stalling their growth or making poor strategic decisions.

For example, in the early stages of business, a small team may not require a full-time Chief Financial Officer or Chief People Officer. However, as the business grows and adds more employees or explores new markets, gaps in financial oversight or HR strategy can quickly emerge. Recognizing these gaps when they develop is critical to sustaining growth momentum.

How to Identify Leadership Gaps as You Grow

A periodic, formal leadership assessment process can help you evaluate whether your current leadership team is equipped to meet the company's growth needs. It’s the first step to addressing leadership challenges.

Here’s a simple process to help you identify leadership gaps:

• Evaluate team capacity: Are your current leaders stretched too thin? Are they managing roles outside their core strengths?
• Look for missing skills: Are there functional areas (like finance, HR, or marketing) where your company lacks expertise?
• Assess leadership scalability: Do your leaders have the skills to scale their departments effectively, or have they reached their growth limits?
• Monitor team dynamics: Are you missing leaders who can drive cross-functional collaboration or manage new layers of complexity?

Companies that consistently assess their leadership teams can spot gaps early and prevent them from becoming more significant roadblocks. Creating a leadership roadmap that aligns roles with your company’s growth stage will help you identify needs before they emerge.

Practical Strategies for Filling Leadership Gaps

Once you identify current or potential leadership gaps, you’ll need to take proactive steps to fill them. These actionable strategies will help you scale your leadership team effectively:

1. Develop existing leaders: Invest in the development of your current leadership team. Coaching, mentorship, and professional development opportunities can help your team grow into the roles your company needs as it scales.
2. Hire specialized leadership: Sometimes, filling leadership gaps requires bringing in outside expertise. As your company expands, you may need to hire leaders with specialized skills, such as a CFO or a Head of Operations, to handle more complex organizational needs.
3. Create a leadership pipeline: Proactively developing a talent pipeline ensures you have future leaders ready to step into key roles. This approach addresses immediate gaps while also preparing your organization for long-term growth.
4. Conduct real-time leadership assessments: Regular leadership assessments can help you stay ahead of potential gaps and keep leadership challenges under control. 

Real-World Example: How SingleFile Addressed Leadership Gaps

In early 2024, SingleFile's customer pipeline skyrocketed when the Corporate Transparency Act went into effect. To prepare for growth, they partnered with Bolster for an executive talent audit. We consulted with the existing leadership team and clarified their goals for the future. Ultimately, SingleFile opted to hire a Head of Customer Success to help their team keep pace with skyrocketing demand and provide guidance throughout the scaling process.

The SingleFile team is proactive in addressing their leadership gaps and understands the need to bring in specialized talent to support their growth. Their open assessment of their leadership needs will continue to serve the growth of the business.

Unlock the Secrets to Building an Effective Executive Team

Ensuring your leadership team can meet new challenges as your company scales is critical to growth and success. By developing existing leaders, hiring specialized talent, and leveraging flexible leadership solutions, companies can overcome leadership challenges in scaling and continue to grow effectively.

Are you looking to scale your business but unsure what leadership roles are critical at each stage of growth? Download our comprehensive Leadership at Scale report, where we explore the evolving needs of executive teams from Pre-Seed to Series D. Learn how to align your leadership strategy with your business goals and discover the CXO archetypes that will take your organization to the next level.

Download the report now and start building the leadership team that drives success.