Applying The Investors' Playbook To Legal Career Planning

In the early 2000s, I launched a business venture that brought me into the world of venture capital and public markets. Now, as a legal recruiter, nothing has been more instrumental than what I learned from a variety of hedge fund managers, venture capitalists and investment bankers — how to analyze a deal and make a decision quickly. Though they all have different names for their analysis structures, at the end of the day, I realized that it boils down to the traditional SWOT analysis — strengths, weakness, opportunities and threats.

With a sheet of paper and a four-quadrant grid that has strengths, weaknesses, opportunities and threats in each corner, deal junkies work magic in minutes to really understand the lay of the land and act quickly. Many industries could use their approach as a model, and in every one of my endeavors since, I’ve kept this decision-making style with me. Presently, I’ve found it particularly useful for analyzing legal careers.

Analysis Beyond Investments

Lateral movement is a common trend in the legal industry. Lawyers are often thinking about where to take their career next, but few have a clear picture of what that next step ought to be. The SWOT analysis quickly provides incredible clarity when examining a legal career. From the first time I chose to try out a SWOT analysis with a candidate, it worked just as I had predicted and hoped. My candidate was wrestling with the next step of her career and debating whether to take one of two offers or stay at her current firm. So, I pulled out the sheet of paper, drew the four quadrants, labeled each section accordingly and set out to fill in the blanks. Together, we went through the questions: What were the strengths, weaknesses, opportunities and threats at each firm?

Unsurprisingly, what were strengths at one firm turned out to be weaknesses at another. One firm had a deep bench of experts in certain areas — and another did not. Similarly, opportunities at one firm were threats at another. One had a growing practice area with rainmakers spread out where she would fit in nicely. The other had one rainmaker, and there was concern about whether the firm would still keep his practice area a priority if he left. The analysis helped boil down all of the factors into the information necessary to make an informed decision.

As lawyers analyze their work environments in the beginning stages of making career moves, they should reflect on the overarching factors that are important to them, and then think about each in the context of all of the SWOT elements. Some important questions to consider within each element include:

How is the firm positioned in the practice area (locally, regionally, nationally and internationally)?

How is the firm viewed from a diversity standpoint?

What is the bench strength of the firm in the practice area?

How is the firm financially?

Who are the firms' clients?

What is the percentage allocation of those who bring in the business?

What is the state of the firm's management?

Lawyers who drill down on what they value in firms will be better equipped to pursue those that are a true match in desired clients, work and culture.


SWOT analysis isn't limited to analyzing law firms; the exercise also expands lawyers' understanding of their individual qualities to help determine their next steps. When candidates come to me for advice on how they should approach their career trajectory, I pull out a sheet of paper, draw the same quadrants, add the headings and go to work, this time posing the questions to them as an attorney: "What are your strengths, weaknesses, threats and opportunities?"

This self-analysis becomes a little trickier as it’s often a challenge to be this introspective, especially when focusing on the negatives. When it comes to defining strengths, lawyers should consider where they excel in relation to others in the industry. The same applies when defining weaknesses — they should look at the areas where others outperform them. For each category, it may be helpful for lawyers to consider the following to jumpstart their brainstorming and fill out their own SWOT analysis.


  • Specific skills related to the job
  • Education and training
  • Clients, contacts and networks
  • Positive personality traits


  • Skills gaps
  • Negative personality traits
  • Client development
  • Limitations on experience


  • Client leveraging
  • Professional development
  • Career paths available
  • Ways to strengthen network


  • Obstacles
  • Competition
  • Restructuring
  • Education gaps
  • Market conditions
  • Physical health (often overlooked)
  • The unexpected — the proverbial "getting hit by a bus"

The answers that result from this type of reflection can be eye-opening and provide a deeper perspective. Studies show that people spend less time on their retirement planning than they do planning a vacation. And, I dare say, people probably spend even less time on career planning. In my experience, the analyses I have performed have provided lawyers with exceptionally useful insight in terms of developing career game plans. I challenge any lawyer thinking of making a move to take a moment, pull out a sheet of paper, draw the quadrants, fill in the titles and go to work like an experienced venture capitalist would.

This article was originally featured in LAW360, November 7, 2017.

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