So, your company is growing. You’ve moved past the initial startup phase, deals are getting more complex, and the sheer volume of contracts, regulations, and potential risks is becoming a daily concern. Relying solely on outside counsel is no longer sustainable, so it’s time to hire your first in-house lawyer.
This is a pivotal moment. Your first legal hire will shape your company’s culture of compliance, risk management and business partnership for years to come. Get it right, and you gain a strategic ally. Get it wrong, and you could face costly missteps and missed opportunities.
At Leonid, we’ve guided countless companies through this critical hiring process. Based on our experience, here are the five most common mistakes to avoid.
Mistake #1: Hiring a clone of your external counsel
The pitfall: It’s natural to look at the partner at your prestigious law firm - the one who brilliantly handles your litigation or complex M&A - and think, “We need someone like that in-house.” This is often a misstep.
Why it’s a problem: The skills that make an excellent law firm partner are not always the same ones that make a great first in-house counsel. Private practice lawyers are often specialists and “project-based” problem-solvers. Your first in-house lawyer needs to be a generalist and a “product-based” business partner. They must handle everything from HR issues and sales contracts to data privacy and compliance, often on the same day. They need to be proactive, practical and comfortable with ambiguity. Deep, billable-hour expertise in one area simply won’t work in this environment.
The answer: Look for a business-minded generalist with a “preventative” mindset. Prioritise versatility, pragmatism and the ability to translate legal jargon into actionable business advice over a narrow, specialised pedigree.
Mistake #2: Underestimating the cultural fit
The pitfall: Focusing on legal credentials, number of years’ experience and technical skills as a priority, while treating cultural fit as an afterthought.
Why it’s a problem: Your first in-house lawyer isn’t ‘just’ a lawyer; they are a key member of your leadership team. They will need to build trust with every department, from sales and marketing to finance and engineering. A lawyer who is overly rigid, risk-averse or unable to communicate effectively with non-lawyers will quickly become isolated and ineffective. They will be seen as the “Department of No,” stifling innovation rather than enabling it safely.
The answer: LeonidLive! At Leonid, we provide all of our clients with video shortlists of the top 3-5 candidates, with a series of questions which are designed to assess cultural fit. These videos enable employers to quickly assess personality and soft skills, such as how well they communicate. These are things which can never be gleaned from a CV alone and can save hiring managers many hours in the screening stages.
When it comes to the interview stages, be sure to involve key stakeholders from different teams. Present real-world business scenarios and ask how they would approach them. Gauge their communication style. Do they explain concepts clearly? Are their answers practical and business-enabling, or purely defensive? You’re hiring a partner, not just a practitioner.
Mistake #3: Defining the role too narrowly
The pitfall: Writing a job description that focuses too much on immediate priorities – for example reviewing contracts - and risks presenting too narrow a picture of the true nature of the role.
Why it’s a problem: A narrow focus attracts narrow candidates. While contract review may undoubtedly be a significant part of the job, your first lawyer will also be your de facto risk officer, compliance manager, HR advisor and corporate secretary. If you hire someone who only wants to do contracts, you’ll soon find yourself still needing outside counsel for everything else, thereby defeating the purpose of the hire.
The answer: Create a job description that reflects the true breadth of the role. Emphasise the need for a strategic thinker who can build a legal function from the ground up. Highlight responsibilities across compliance, corporate governance, employment law, and risk management. You’re not just hiring for today’s tasks, but for the challenges of the next 3-5 years.
Mistake #4: Waiting until it’s a crisis
The pitfall: Delaying the hire until a major legal issue - whether it is a lawsuit, a regulatory investigation or a disastrous contract - forces your hand.
Why it’s a problem: Hiring under pressure leads to bad decisions. You lack the time to run a thorough process, assess cultural fit and find the right long-term partner. You end up with a “firefighter” who is brought in during a state of emergency, which sets a negative tone for their entire tenure. Furthermore, the cost of the crisis itself may far exceed the salary of a lawyer who could have prevented it.
The answer: Be proactive. The right time to hire your first lawyer is when you see the legal workload consistently impacting business velocity, when the annual outside counsel bills are becoming a significant expense, or when you’re entering a new market or product line with substantial regulatory hurdles.
Mistake #5: Failing to set clear expectations with the business
The pitfall: Hiring a great lawyer but not preparing the rest of the company for how to work with them.
Why it’s a problem: If your teams are used to getting quick, informal answers from outside counsel (or making decisions with no legal input at all), they may see the new in-house lawyer as a bottleneck. Without clear communication from leadership, the lawyer will struggle to integrate and demonstrate their value.
The answer: Before your new counsel starts, communicate their role and mandate to the entire company. Explain that they are a strategic resource designed to help the business grow safely. Encourage teams to involve them early in projects, not just at the contract stage. Position the legal function as an enabler, not a barrier.
Build your foundation for success
Hiring your first in-house lawyer is one of the strongest signals that your company is maturing. It’s an investment in your future stability and growth. By avoiding these common mistakes, you can find not just a legal expert, but a true business partner who will protect your company and help it navigate the path to success.
At Leonid, we specialise in connecting innovative companies with exceptional legal talent. If you’re considering building your in-house legal team, please get in touch with Phil Redhead today for a confidential discussion.
