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From Success to Succession: Five Rules For Building Lasting Leadership

By Dan Haley

success transformation concept

Dan Haley, General Counsel and Corporate Secretary at Guild Education, has experience building and leading world-class legal departments at both publicly traded and private companies in the health information technology, marketing technology, and education technology spaces.

January 16, 2024

How do I define “success” as a general counsel?

In my experience, the answer is simple: A successful GC identifies, motivates, prepares, and retains a successor, and then gets out of their way. This principle, a key tenant of “Jack Welch and the GE Way,” remains a gold standard for leadership.

That approach has held up, and it applies equally to any executive leader. When we come to the end of a run, how do we assess whether we have succeeded? In a word: Succession. That was certainly the case for me in 2023, when I left my GC role at Sprinklr and moved on to a new opportunity at Guild.

I recently stumbled upon one of my favorite photos of the legal team at my first company, athenahealth, taken at a rowing-based team-building event we did in the summer of 2016.

Dan Haley, photo of first legal team at athenahealth

As I examined this photo years later, I was struck by the fact that six of the 30 people standing on that dock with me — a full 20% — have gone on to lead their own legal departments, as GCs. Two of them succeeded me directly, at two different companies. And multiple others currently lead large and impactful teams and functions, at athenahealth and elsewhere. It is impossible to adequately express, never mind quantify, the pride I feel in them and their accomplishments.

I don’t claim access to any secret succession alchemy, but I am mindful of the fact that this kind of success(ion) does not just happen. Here are my Top Five Rules for Effective Succession Planning:

  1. Hire people who want your job and are capable of doing it (eventually). There is a raft of corporate clichés around this basic notion: hire people who are smarter than you are. This is 100% true. Smart, ambitious people make your team better, they make you look good, and they set your team up for durable success that outlasts your tenure.
  2. Caretakers care. Time spent getting to know the members of your teams, including on a personal level, has immeasurably high ROI. Understand, and then follow and help actively to guide, their ambitions. Create opportunities for them to shine, even—or especially! —when that requires you to take a back seat. Encourage them to stretch outside of their comfort zones, and to explore new areas of expertise. Backstop them when they face challenges or run up against failures. Most importantly, do all of this as part of your regular operating cadence, not just during the annual review cycle.
  3. Retention is about more than money! Any professional worth his or her salt expects to be compensated fairly. But retention based entirely on money is short-term retention, at best — talent who comes to or stays with you purely for cash is not an invested member of your team; he or she is a mercenary who will almost certainly leave when a higher offer comes along. Retention based on fair compensation in addition to learning and growth opportunities, scope expansion, trust, mutual support, team dynamics and culture, and mission alignment? That is where the magic lives.
  4. If you love somebody, set them free. Gordon Sumner had this one right! A legal department, like most corporate organizations, is a pyramid. There is progressively less room at each successive level. If you succeed in building a great team peopled by strong and ambitious performers, you will inevitably—frequently, even —face the risk of losing a key team member to an external opportunity. When that happens, it is a deep compliment to you as well as to your possibly departing team member. Treat it as such! First and foremost, always be happy for that person (see rule #2!) and offer to be a reference for them. Do not unleash a guilt trip or make this be about you. Retention efforts should be all about one question and one question only: is there anything about this new opportunity (scope, learning opportunities, exposure) that we can replicate here to keep you? Handle a valued colleague’s departure the right way, and you may well work together again down the road.
  5. Intent is not a plan. Like cleaning out the garage, succession planning too often lives on the “I’ll get to it… eventually” end of the busy exec’s to-do list. If you take one thing away from my ramblings, let it be something I already noted above: The preconditions for succession success are a long-term commitment.

Good hiring without subsequent, focused attention to development and retention will leave you with high turnover and no bench. Caretaking with insufficient ‘care’ will result in low levels of engagement, loyalty, and performance on your team. Exclusive focus on compensation will give you, at best, a high-performing team of short-termer mercenaries, and at worst a group of self-oriented, internally competitive free agents. And playing blocker against opportunities that come at your team from the outside will undermine trust and damage morale.

Conversely, a GC who combines deliberate adherence to the five rules above will find him or herself with a high-performing and resilient team that will succeed during and long after his or her own tenure in the role.

Most importantly, as I have learned twice now to my extreme pride and deep satisfaction, a succession plan will enable you to be open to your own unexpected opportunities. You will be secure in the knowledge that should you leave, your company and your team will be in good and steady hands.

That’s a pretty good definition of success.

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