9 Crucial Questions Every Owner Must Answer When Growing Their Team

Align Strategic | Founder Freedom
9 Crucial Questions Every Owner Must Answer When Growing Their Team

 By Cheryl Powers

Expanding a team is more than just adding bodies to your company—it's about finding the right kind of people who'll turbocharge your growth. As an owner, you need to be tactical and thoughtful about whom you bring into your fold. It's not just about filling positions; it's about enriching your team's dynamics and enhancing your company’s capabilities. 

The Complex Journey of Team Growth

When you're at the helm of a small or mid-market business, expanding your team is like navigating through uncharted waters. It's complex, it's challenging, and it's absolutely critical for your company's success. 

Let's break down this journey and understand the intricacies involved.

Understanding the Need for Expansion

The first step in this journey is recognizing when your team needs to grow. This isn't just about filling vacancies or reacting to work overload. It's about understanding the strategic direction of your company and how a larger team can propel you towards your goals. Are you entering new markets? Are you diversifying your product line? Answering these questions will help you pinpoint the exact moment when expansion becomes necessary.

Evaluating the Current Team Dynamics

Before you start drafting job descriptions, take a closer look at your current team. How are they performing? Is there an evident skill gap that's holding back your company’s potential? Sometimes, the key to growth lies not in simply adding more people but in maximizing the potential of your current team. Assess their strengths, weaknesses, and areas where they could benefit from additional support. This step - done correctly - will also help you understand precisely what sets your top performers apart from your average and below-average producers.

Balancing Quality and Quantity

It's easy to get caught up in the numbers game—more employees, more productivity, right? Not necessarily. The goal is not just to increase headcount but to bring in people who add real value. This means finding individuals who not only have the right skills, strengths, competencies, and DNA but also fit into your company culture and share your vision. Remember, one outstanding employee can be worth much more than several mediocre ones.

Cultural Integration and Team Harmony

As your team grows, maintaining the integrity of your company culture becomes a challenge. New hires need to be integrated in a way that they contribute to, rather than dilute, the existing culture. This requires a robust onboarding process that goes beyond mere training and focuses on immersing new employees in your company’s ethos.

Adapting Management Styles

With a larger team comes the need for more structured management. This doesn't mean micromanaging every aspect of your employees' work but rather developing a management style that empowers them and an operational mastery that leads to a self-managing operation. Effective communication, clear goal setting, and regular feedback are key. As a founder, you'll need to evolve from a hands-on doer to a strategic leader who delegates and oversees.

Promoting Interdepartmental Harmony

As your company grows, so do its departments and its need for managers. Ensuring that each department manager works in harmony with the others rather than in silos is critical. Encourage collaboration and open communication between departments. Create cross-functional projects and team-building activities to bridge gaps and foster a sense of unity.

Preparing for the Future

Team expansion is not just a solution for current challenges but also a preparation for future ones. As your team grows, so does your ability to tackle more ambitious projects, enter new markets, and innovate. Always keep an eye on the horizon and plan your team's growth in a way that aligns with your long-term vision.


Here Are 9 Crucial Questions Every Owner Wrestles With When Growing Their Team


When is the Right Time to Grow Your Team?

Timing is everything. Expand too early, and you risk stretching your resources thin; wait too long, and you miss crucial growth opportunities. Look out for signs like overworked staff or untapped market potential. But remember, the key is to strike a balance between seizing opportunities and maintaining your company's health.


In the high-stakes world of growing business value, timing your team's expansion, especially when it comes to hiring leaders, can be a game-changer. A real-world example that encapsulates the essence of this delicate timing is the story of Airbnb's strategic leadership hire during its early growth phase.


The Airbnb Example

In its early days, Airbnb, like many companies, was managed by its founders, who were deeply involved in every aspect of the business. As the company started gaining traction, the workload increased exponentially. The founders, Brian Chesky, Joe Gebbia, and Nathan Blecharczyk, were adept at handling the initial stages of the business, but as Airbnb began to scale, they faced challenges that were outside their areas of expertise, particularly in complex fields like international expansion, legal compliance, and sophisticated marketing strategies.

Recognizing these challenges, the founders made a strategic decision to bring in experienced leaders. In 2011, they hired Ed Baker from Uber to lead their growth team, and later, in 2015, they brought on Laurence Tosi from Blackstone Group as their CFO. These were pivotal moves. The timing was crucial; Airbnb was at a point where the founders had built a strong base but needed additional expertise to scale the business globally.

Impact of the Timely Hire

Expertise in Scaling

These leaders brought in expertise that was critical for Airbnb’s rapid scaling. Their experience in managing large, complex operations helped Airbnb navigate through the challenges of international laws, diverse market dynamics, and large-scale financial management.


Allowing Founders to Focus

With seasoned leaders managing key aspects of the business, the founders could focus on innovation and overall strategy. This division of labor is essential in a growing company, where strategic focus can often be diluted by operational challenges.


Market Expansion and Growth

The new leaders played a crucial role in Airbnb's expansion into new markets. They helped in identifying and exploiting untapped market potential, which might have been missed without their seasoned perspective.

Avoiding Overstretching Resources

By hiring these leaders at a time when the company had established a market presence but was not yet overextended, Airbnb avoided the pitfall of stretching its resources too thin. The new hires brought in needed efficiencies and strategies that optimized resource use.

The right time to grow your team, especially when it comes to hiring leaders, is when your company is at the cusp of a new phase of growth—where the challenges begin to surpass your expertise and that of your existing team. Many owners wait too long and cost themselves time and money. The lesson from AirBnB is clear: monitor your company’s growth trajectory closely and identify the moment when bringing in experienced leaders can turn potential growth into realized exponential growth without overburdening your existing resources.

How Do You Find the Right Talent?

Finding talent is one thing; finding the right talent is another. You're not just looking for competencies and skill sets; you're looking for people who vibe with your vision and culture. It's a mix of art and science, requiring a keen eye for potential, a strong discipline to understand and leverage the data from your team evaluation, and a knack for selling your company's dream.

Resist falling in love with a candidate who “looks the part” or worked for a big logo in your industry. Understand exactly what you need in each role and be relentless in finding the best candidate available to you. 

Utilizing Modern Recruitment Channels

Don't just stick to traditional hiring methods. Embrace social media, professional networks, and recruitment specialists. When we help clients fill their roles, we work with you to widen your net and help you pinpoint the talent that has the requisite skills and experience and that also resonates with your company's ethos.

What Skills and Roles Are Most Crucial?

Identify which roles and skills are non-negotiable for each of your roles. It's not just about the hard skills; soft skills are equally important. You want a team that's technically sound and adaptable, ready to pivot when the business landscape shifts.


Building a Diverse and Dynamic Team

Diversity isn't just a buzzword—it's your ticket to a plethora of perspectives and innovative solutions. Aim for a team that's rich in experiences and backgrounds, fostering a culture where learning and adaptability are the norms.

How Do You Maintain Company Culture with New Hires?

Your company culture is the soul of your business. As you expand, make sure new hires don't dilute it. Set up onboarding processes that immerse them in what your company stands for. It's about weaving them into the fabric and knowledge base of your company, not just adding them to the payroll.


Fostering a Collaborative Environment

Create an environment where collaboration isn't just encouraged; it's the default. This means open communication channels, robust feedback, and tackling the unique challenges of remote and hybrid work setups head-on.

Balancing Cost vs. Quality in Hiring Decisions

It's a classic business conundrum: do you “save” money or invest in top talent that takes you farther faster? Remember, skimping on talent can cost you more in the long run. Quality hires are an investment in your company's future—choose wisely.

Ensuring a Perfect Fit for Your Company

Are They a Fit for You, the Owner?

Every new hire, especially those you'll work closely with, should energize you, not drain you. If you're not looking forward to working with them or having meetings with them, that's a red flag. They should bring ideas and enthusiasm to the table that align with your vision and drive.

Are They a Fit for Your Customers?

Your team should understand and resonate with your customers. They need to speak their language and empathize with their needs. If they can't connect with your customer base, they're not right for your company.

Are They a Fit for Your Suppliers and Partners?

Your team's interaction with suppliers and partners should be smooth and synergistic. They must be able to maintain and nurture these critical relationships while deeply understanding their nuances and dynamics.

Are They a Fit for the Team?

This is crucial. Your new hires must gel with the existing team. They should complement and enhance the team dynamics, not disrupt them. Look for individuals who can collaborate effectively, respect diverse viewpoints, and contribute to a positive work environment.

Do They Deliver Results?

At the end of the day, they need to deliver. It's not just about fitting in; it's about contributing to your company's growth. Monitor their performance closely. If they're not meeting expectations, address it swiftly. Remember, good conflict is okay, but negativity and consistent underperformance are not.

Expanding your team is a multifaceted journey that requires careful planning, strategic thinking, and a deep understanding of your company's needs. It's about creating a team that's not just bigger but better—more cohesive, more efficient, and more aligned with your vision. As a founder, your role is to guide this expansion with a steady hand, ensuring that each new hire contributes to your company's growth and success.

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