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Why Your Growing Business Needs an Experienced Outside Lawyer, Instead of Hiring a Chief Legal Officer

Why Your Growing Business Needs an Experienced Outside Lawyer, Instead of Hiring a Chief Legal Officer

Joseph Tung
A Silver Fox Advisor

Running a privately held business means wearing many hats. As your company grows, legal questions multiply: contracts need review, employees raise concerns, regulatory requirements shift, and strategic decisions carry legal weight. At some point, every business owner asks: Should I hire a chief legal officer, or work with an outside lawyer?

For most privately held businesses, the answer is clear: retain an experienced outside lawyer instead of hiring a full-time CLO. Here’s why.

Cost-Effectiveness Without Compromise

Hiring a chief legal officer means committing to a six-figure salary, benefits, office space, and ongoing overhead—even during slower periods when legal needs are minimal. For a privately held business, that’s a significant fixed cost that doesn’t scale with actual demand.

An experienced outside lawyer operates on a flexible model. You pay for the work you need, when you need it. Whether you’re negotiating a major contract, handling an employment dispute, or planning a business expansion, you get senior-level expertise without the burden of a permanent executive salary. This arrangement preserves capital for growth, operations, and other priorities that drive revenue.

Breadth of Experience Across Industries and Practice Areas

A chief legal officer typically brings deep expertise in one or two areas, such as corporate governance, perhaps, or employment law. But privately held businesses face legal issues across a wide spectrum: intellectual property, commercial litigation, risk management, cross-border transactions, regulatory compliance, and more.

An outside lawyer with broad business and legal experience, someone who has worked in major law firms, in-house legal roles, and their own practice, brings a toolkit built over decades. This type of lawyer has advised startups navigating early-stage challenges, helped mid-sized companies scale operations, and counseled established enterprises on high-stakes decisions. They’ve seen how legal strategies play out in real time, across industries like energy, technology, healthcare, and beyond.

That breadth is invaluable. When a legal question arises outside your CLO’s specialty, you’re back to hiring outside counsel anyway. With an experienced outside lawyer as your primary resource, you already have access to versatile, practical guidance tailored to your business.

Strategic Business Insight, Not Just Legal Advice

The best outside lawyers don’t just answer legal questions, they understand business. They know how to align legal strategies with your commercial goals, identify growth opportunities, and anticipate challenges before they become crises.

A lawyer who has served as a business advisor and legal strategist for startups, growing companies, and major enterprises brings more than technical legal knowledge. They bring judgment shaped by real-world outcomes: what works, what doesn’t, and why. This perspective helps you make informed decisions that balance legal risk with business opportunity.

For example, when negotiating a vendor contract, a purely legal review might focus on indemnity clauses and liability caps. A lawyer with business acumen will also consider cash flow impact, relationship dynamics, and how the terms affect your ability to pivot if market conditions change. That’s the difference between checking boxes and adding value.

Flexibility and Scalability

Your legal needs fluctuate. Some months require intensive work, launching a new product line, resolving a dispute, or restructuring operations. Other months are quiet. A full-time CLO sits idle during those lulls, yet you’re still paying their salary.

An outside lawyer scales with your business. Need intensive support for a major transaction? They’re available. Quiet period with routine questions? You pay only for the time you use. This flexibility is especially critical for privately held businesses, where agility and efficiency often determine competitive advantage.

Access to a Network of Specialists

Even the most experienced outside lawyer can’t be an expert in every niche area of law. But a well-connected lawyer brings something equally valuable: a network of trusted specialists.

When you need niche expertise, securities law for a capital raise, patent prosecution for a new invention, or immigration support for key hires, your outside lawyer can coordinate with specialists, manage the process, and ensure consistency across your legal strategy. You get the depth of a full legal department without building one.

Objectivity and Fresh Perspective

A chief legal officer is embedded in your company culture. While that has benefits, it can also create blind spots. Internal counsel may become too close to personalities, politics, or past decisions to offer fully objective advice.

An outside lawyer brings fresh eyes to every situation. They’re not invested in internal dynamics or prior commitments. Their loyalty is to the business outcome, not to office relationships. This objectivity is especially valuable when difficult decisions arise, restructuring leadership, addressing compliance gaps, or navigating shareholder disputes.

Proven Leadership and Mentorship

Many experienced outside lawyers have led legal teams, mentored young attorneys, and shaped organizational culture. They understand what it takes to build systems, develop talent, and foster collaboration.

For a privately held business, this leadership experience translates into practical guidance on building internal processes, training your team to spot legal issues early, and creating a culture of accountability. You’re not just hiring a legal advisor, you’re gaining a trusted partner who can help your business mature.

A Real-World Example

Consider a lawyer with more than two decades of experience across top law firms, in-house roles at a major global corporation, and their own successful practice. This type of lawyer has handled complex litigation, corporate transactions, risk management, and business development at every stage of company growth. They’ve served as a director at a collaborative law firm, mentored young professionals, and advised business owners through some of their most challenging decisions.

This breadth of experience, spanning industries, practice areas, and business contexts, is exactly what a privately held business needs. It’s the kind of versatile, practical expertise that a single CLO rarely brings, and it’s available on a flexible, cost-effective basis.

When Does Hiring a CLO Make Sense?

To be clear, there are situations where hiring a chief legal officer is the right move. If your business has reached a scale where legal issues arise daily, where regulatory oversight is constant, or where you’re managing dozens of active matters across jurisdictions, a full-time CLO may be justified.

But for most privately held businesses, even those with significant revenue and complexity, retaining an experienced outside lawyer delivers better value, greater flexibility, and access to a broader range of expertise.

The Bottom Line

Your business deserves excellent legal guidance. But that doesn’t mean you need a chief legal officer on the payroll. An experienced outside lawyer offers the strategic insight, versatility, and practical judgment you need, at a fraction of the cost and with the flexibility to scale as your business grows.

Before committing to the fixed overhead of a CLO, consider whether an outside lawyer with deep business experience, broad legal knowledge, and a track record of guiding companies like yours might be the smarter choice. The right lawyer becomes more than a service provider, they become a trusted advisor who helps you navigate challenges, seize opportunities, and build a stronger, more resilient business.

Joseph Tung, the Houston Office Director for Grable Martin, PLLC embodies this model with a full service firm that boasts experience at big law firms, in-house legal roles, and leadership positions. He and his firm offers strategic insight and broad expertise that growing businesses require, without the overhead of a full-time executive.

September Leadership Solution

THE LEADERSHIP TRAINING/MENTORING CORNER

In the August 2025 Newsletter, we started a series called “The Leadership/Mentoring Corner” in which we posed a thought-provoking situation for you to think about and put yourself into, asking yourself, “What are your next steps?” 

SEPTEMBER LEADERSHIP SITUATION

Charlie is a Vice-President at a small retail service business, a position he has held for three years. The business’ sales have been flat for the last five years at around $3.0 million a year. The President of the business has been in his position for about five years, and he and Charlie work well together. The owner of the business started the business some 30 years ago. The owner knows the specific retail service inside and out, but is not necessarily good with finances, marketing, or business planning. Over the 30 years the business has been in operation, there has been a high employee turnover due to the owner’s management style and lack of big-picture business strategy focus. 

The business just lost one of its largest clients that represented 30% of the total annual sales. The business owner blames the business’ President and terminates the President on the spot. 

Charlie is afraid the owner is going to ask him to move into the President’s position, and Charlie is not sure he even wants the position. Charlie has his resume out to a couple of placement firms and has a second interview scheduled this afternoon.