Senior executives across every industry are feeling the pressure. Investors are growing more impatient by the day. Technology is disrupting the workforce and uprooting traditional business practices.

Lawyers — in-house counsel in particular — are particularly at risk. Regulators are growing more assertive. Our political environment remains increasingly dynamic. To help companies navigate this complex business landscape, senior management is leaning more on their general counsel than ever before. This can make a GC’s job much more exciting, but it also increases the pressure.

Every company views success through a different lens. As a former general counsel in the financial services and technology space, I know this all too well. As a leader, I’ve learned to live by what I call the Kenny Rogers Rule of Business. In other words, you’ve got to know when to hold ’em; know when to fold ’em; know when to walk away, and know when to run. Growing into success as a legal executive is not only about learning business competencies — it’s also about knowing when to spot red flags and walk (or run!) away.

Competencies and Characteristics of Strong GCs

When we talk about the traits of anyone in a leadership position, we usually like to qualify these characteristics as learned versus innate. Wherever you stand in this discussion, I believe many of these traits can be instinctive and developed through learned experiences. This is why companies would do best to look for a general counsel who demonstrates a combination of sound judgment and a growth mindset. Many characteristics make strong legal leaders, but below is a list of some of the most prominent:

Tested Judgment

It’s vital that senior executives not confuse “good brains” with “good judgment.” I’m paraphrasing a Wall Street Journal article written by Peggy Noonan over a decade ago, but it’s still a powerful message today. GCs, in particular, must be able to evaluate and weigh the impacts of every single decision and course of action made by a company’s senior executives. In-house lawyers must also use their judgment to lead cross-functional teams. So when looking for a general counsel, don’t look just for intelligence, but rather for people who can show good and tested judgment.

Versatile Communication

GCs must regularly communicate with diverse audiences, from the company’s senior management team to the board to its employees. Whether you are the GC or looking to hire a GC, a good legal executive needs to adapt their communications to any group and simplify complex legal matters whenever necessary. Versatile communication skills are not just intuitive; they are learned through experience. Good communication skills are also a key part of a growth mindset.

Strategic Thinkers

When asked about choosing people for a team, General Colin Powell once said to look for those that “see around corners,” and I believe this applies to general counsels as well. GCs must anticipate and prepare themselves for issues and risks before and after they arrive. Strategy-oriented GCs can proactively identify solutions to eliminate risks and grow the business. A purely reactive lawyer without a strategic “see around corners” focus may react too soon or, worse, too late.

Cultural Fit

Anyone that works for a company must fit in with that organization’s culture, including the legal team. They must work directly with senior management while also meshing with the company’s other employees. If they aren’t a good cultural fit, it could be damaging to that company’s growth and success, as well as that of an in-house lawyer.

BUT, sometimes, the expectations senior management has for a general counsel are meant to cover up red flags within the business. GCs must look for these red flags, as many regulated businesses have personal liability for them.

Red Flags: Knowing When to Run

Serving as a general counsel or legal executive often comes with personal liability. Here are some business red flags I’ve uncovered during my time in-house:

Values Mismatch

If your values as a lawyer and those of the organization you’re serving don’t line up, it’s time for a new job. Whether the misalignment is because of the culture, diversity, or other issues within the organization, if senior management is cultivating these values, it may not be the place for you. In my parents’ era, people stayed in their jobs for decades, maybe even for life. However, as you grow your career, you can no longer be afraid of leaving a job that doesn’t align with your values because a short stint with an employer “doesn’t look good on your resume.” The costs to your reputation may be far higher for staying than for leaving quickly. The same goes for companies who hire lawyers whose values don’t align with those of the company!

Risky Business

As a lawyer, it is often your job to manage business risk. This can mean everything from financial risk to employment risk to premises risk. At first, risk management can seem like a way to work hands-on with senior management, but it can also have a darker side. If you believe people within your organization are hiding or misrepresenting risks to you, run, don’t walk away. 

Blame Game

This isn’t a popular thing to talk about, but occasionally, senior executives choose to “blame the lawyer.” As general counsels, we’ve all experienced this at one point. It’s a common refrain from the boardroom to the courtroom: “My lawyer told me I could do it.” 

If a company wants you to succeed, you’ll succeed. But if you’ve noticed any of these red flags working with your company, follow the Kenny Rogers Rule of Business and know when to run.

On New Year’s Eve 1999, as the clock was about to strike on Y2K, I set a goal to complete a list of 50 challenges in the first decade of the new millennium. In 2009, I found myself staring down at the very last item on that list: Run the New York City Marathon.

At the time, I wasn’t much of a runner. In fact, I could barely squeak out a 5k. But I had always been someone who set big goals. So over the course of 2009, I put my head down and I did the work. I found a training plan and I raised the money to obtain a charity entry to the New York City Marathon. And on the eve of the expiration of my bucket list, I crossed the finish line of the 40th New York City Marathon.

The hard work paid off, and I was hooked. Between 2009 and 2016, I went on to run 14 more marathons all over the world.

To this day, I’ve been surprised by just how impactful marathon running has been in my life. It’s given me purpose and meaning and has even brought me closer to family. But one area that surprised me the most was how much marathon running has affected my professional life.

It may seem ludicrous to make a connection between running and business, but the two run closer than you might think. I last crossed a marathon finish line in 2016. But the discipline I learned from running continues to influence me in my career today, especially as it concerns my long-term goal setting. 

You’ll work harder for something you love.

Running is hard. If you don’t find any enjoyment in it, you’re not going to be any good at it. I’m not saying you have to fall in love with running after your first attempt (if I’m being honest, not many people do). You’ll have good days and bad days. But for some, if you keep at it, you’ll eventually find those “finish line moments” that make running so worthwhile.

Success in marathon running requires long term planning to build up mileage. One doesn’t simply get off the couch and start with 26.2. But if you keep with it for weeks, months, or years and still resent it, then running just isn’t meant for you. And if you have zero passion for an activity, you’ll have zero motivation to get better at it. Can’t the same be said about your career?

If you don’t have a passion for (or at least believe in) your career or industry, you won’t feel that there’s any value in setting long-term goals for yourself. Why would you? If your heart isn’t in something, you aren’t going to care if you get better at it. You’ll accept stagnancy because challenging yourself to grow in your role and industry will feel like more work than would be worth the reward. The things you love don’t always love you back.

People often believe that consistent training, getting enough sleep, eating right, and stretching before a run are enough for a good performance. But really, you can still tear muscles, get winded, and even break bones — no matter how seasoned of a runner you are. The same is true in business. Projects you work on will flop. A colleague will let you down. Your manager will set expectations that may feel impossible to meet. Hardships will happen. If you don’t believe in what you do, you won’t be motivated to push yourself to succeed.

Success is a solo journey, but a team effort.

One of the things that attracted me to running the most was how it’s a combination of individual purpose and team effort. You are solely responsible for achieving your long-term goals. That doesn’t mean you have to be alone in your efforts, but no one can cross that finish line for you.

Every marathon runner shares similar goals of working on shaving minutes off of their time or gradually increasing their mileage. Because these are shared goals among marathon runners, you’ll eventually establish your own tight-knit support system of runners. It’s this group that will encourage you to push your limits. They will be there to console you when you fail, and they’ll be there to celebrate you when you accomplish a goal. And you’ll do the same for them. 

The only way to become a better runner is to pound the pavement every day (figuratively and literally). I couldn’t imagine how much harder this would have been without a great support system behind me. From the friends and mentors I ran with daily, to the folks who paced me on the marathon course, to the cheerleaders who showed up at every race.  

This is a mirror image of your career. Whether you’re an executive, manager, or brand-new employee, your entire company is all working towards the same goal of achieving organizational excellence. While you’re all in lockstep carrying out the strategic plans you set, each individual person has their part to play in meeting the business’s overall goals. But even though you have your own course to follow, deadlines to meet, and to-do list to complete, you also have the support and encouragement of your colleagues when things get tough.

If you fail, reorient yourself and try again.

There is no one-size-fits-all strategy to become a better marathon runner. What works for one person won’t necessarily work for you and your running goals. The way we often discover what works best for us is through failure. Don’t let this failure beat you down, but rather, turn it into an opportunity for improvement. 

Have you ever run a race and hit the dreaded “wall”? There’s a reason why it felt like your body was going to give out on you. Maybe you didn’t pace yourself like you should have, or perhaps you forgot to hydrate yourself appropriately. Recognizing the “why” of failure will help you avoid the same mistakes in the future.

Now think back to your career. Every professional will make mistakes that may put their work in jeopardy. If you own up to these mistakes and analyze every misstep that led you to this moment, you can take a step back, adjust your plan of action, and learn from what went wrong. 

In marathon running and in business, there is nothing more satisfying than that “finish line moment.” Setting big goals and having big dreams are both important. But crossing that finish line is unlikely unless you have the right discipline in place to get you there.