Hiring the second lawyer on your team: what to look for and how to test commercial judgment

When a general counsel hires the second lawyer, the job is rarely to be a smaller version of the GC. Look for someone who can take a defined body of work off your desk, make sound calls without checking in every time, and tell you early when a matter is bigger than it looks. Test that with a structured exercise, not just a conversation about past roles.

What the second lawyer is for

Start by deciding which of three jobs you are filling, because they need different people.

• Capacity. You know what good looks like and need someone to do more of it. Look for speed, reliability and comfort with volume.
• Capability. You lack an area, such as privacy, employment or technology contracts. Look for depth, and for the ability to explain it to non-lawyers.
• Coverage and leadership. You want someone who could run the function when you are away or as it grows. Look for judgment about priorities and people.

Write the job as a list of recurring decisions the person will own, not a list of tasks. "Approves standard customer paper within agreed limits" says more than "reviews contracts."

What to look for

• Comfort being the only lawyer in the room. In a small team there is no senior colleague to ask. Probe for examples where they decided, escalated or declined.
• Business fluency. Can they describe how a company they worked for makes money and where legal helped or got in the way?
• Clear writing. A second lawyer's emails and summaries become the legal function's voice. Use a synthetic exercise written for a non-lawyer; do not request a prior client's work product merely because it can be redacted.
• Range of judgment. Someone who flags everything is as unhelpful as someone who flags nothing. Look for calibrated risk language.
• Fit with you. You will share decisions and workload. Ask how they like to be managed and what they do when they disagree with a decision.

How to evaluate commercial judgment

Commercial judgment is the ability to protect the company while helping the business reach a decision. Résumés show where someone worked, not how they decide. Use a structured exercise based on synthetic or explicitly authorized material, with the same competencies and rating criteria for each candidate. OPM's structured-interview guidance explains the value of job-related questions and consistent ratings.

Run a scenario exercise

Give every finalist the same short scenario, drawn from your own typical work, with a clear business goal, a counterparty with leverage, a deadline and a few risky terms. Ask them to talk through:

1. What they would accept, push back on and escalate, and why.
2. What they would want to know before deciding.
3. How they would explain the decision to a sales leader in two minutes.

Score each answer on the same four points: did they identify the real risk, did they weigh it against the business goal, did they propose a workable alternative, and did they know when to escalate.

Add a short work sample

A one-page written recommendation on the same scenario shows how they reason on paper. Keep it short and paid if it takes more than an hour.

Check references on judgment, not only on pleasantness

Ask former managers: when did this person decide something that turned out well or badly, and how did they handle it? Ask what they would trust this person to decide without supervision.

Consider a trial period

Some teams use a fractional or interim arrangement to see how someone works before making a permanent offer. Clio worked with a fractional lawyer who later joined full time, giving the team a chance to assess fit while the work continued. This is one route among several; it does not replace reference checks.

A scorecard to copy

For each finalist, rate one to five on:

• Owns recurring decisions without hand-holding
• Calibrated risk language
• Business fluency
• Written clarity
• Handling of the scenario exercise
• Reference feedback on judgment
• Working style fit with the GC

Write down what would be a deal-breaker before you start, so enthusiasm for one candidate does not move the bar.

Common mistakes

• Hiring a mini-GC when the need is capacity.
• Overweighting prestige of previous employers.
• Skipping the written work sample.
• Giving each finalist a different exercise, which makes comparison meaningless.
• Leaving out the people who will work with the new lawyer every day.

If you are not ready to hire permanently, we can help you find fractional in-house counsel to carry the work while you clarify the role.