Sullivan’s travels – tales of an in-house legal veteran

Should you share a campfire with a seasoned adventurer, you’re bound to hear a few stories, from fire-breathing dragons to mystic castles. If you stay awhile, you’ll hear about triumphs and woes. Pay particular attention to every lesson they learned because they’ve obviously lived to tell the tale.


When it comes to his career, James Sullivan, Chief Operating Officer and General Counsel at Ziglu, has had his fair share of adventures. He’s worked in private practice, telecommunications, financial services (including time as a fund director during the financial crisis) and been involved in three fintech start-ups. Oh, and did we mention he’s also found the time to complete an MBA. Travelling this varied pathway, he’s learned some valuable lessons:

Lesson 1: Trust is Everything, but don’t Trust Everything.

Throughout Sullivan’s travels, there has been one ever-present fundamental in every team he’s been part of, and that is trust. “The one thing that underpins a team is trust. Trust is the foundation, the bedrock of a happy team,” he says. “A core component of the trust relationship is trusting your manager to be able to have full and frank two-way dialogue. A lot of managers are reluctant to do that, so you’ve got to enable people to have full and frank conversations with you and challenge you.”

Without the ability to challenge and dialogue effectively, it is likely your team will feel they are being dragged along by your whims as opposed to forging their own destinies. Not so much a cohesive unit, rather a collection of dusty marionettes.

Sullivan says that integral to this process is creating an environment where it is possible to have these discussions without the threat of backlash. “Provide an environment of psychological safety. For a lot of people, it can be difficult working in an organization. You have to create an environment where people can come to you with difficult problems.”

“The key thing is that the person trusts that they come to you with anything and you’re not going to blame them. You’re just going to get to the solution and then look for the lessons learned.”

Lesson 2: Maintaining Morale

Imagine the scene: You’ve been chased away from a pile of treasure and kicked off a mountain by a dragon. You drag yourself back to the inn empty-handed, nursing bruised bodies and even worse, bruised egos. Your usually upbeat band of merry men and women and rogues are a little down in the mouth and no one has even touched their ale. Exchange the dragon for acquisition, large purchase or any other high-complexity piece of work an in-house counsel might face and the above is undoubtedly a familiar scenario.

Sullivan uses two key tools to maintain morale within his adventuring party. The first is to check in and see how they’re going.

“Make sure you’re having regular one to ones with your team. I fall down on that myself sometimes, but I do try to make time for my teams. Conversations with the leaders of my teams need to be not just about all the things you’re working on, they also need to include how you’re getting on, how are you feeling. Lots of open questions so it ends up being a conversation rather than an opportunity to report up.”

His second key tool is recognition and praise. “Giving recognition and making sure people feel they are appreciated and recognized by you costs nothing. It’s easy to do. But take this one step further, make sure people feel recognized publicly too. You’ve got to be able to show them recognition.”

The perfect time to employ these learnings is now. You take a step onto the table and regale the other patrons with the story of how, if not for one large breath of fire your team would’ve been safely off the mountain with more riches than they’d ever dreamed of. The inn erupts in cheers. Most importantly, all your team are beaming with pride having been publicly recognized for their heroics.

Lesson 3: Rising up the Ranks

You’ve completed your course at knight school and are ready for your first adventure. How do you know when you’re ready to make the step up from orcs and goblins to trolls and dragons? Sometimes it is not the size of the adventurer, but the size of the adventure which leads to the greatest progression.

“When I look back at my career, I think the thing that has progressed my career is not necessarily just changing jobs or being promoted, it’s taking on really large, chunky and impactful projects,” says Sullivan. “Things that made a big difference to the business and got me noticed by senior people within the business.”

The same also applies when you want your team members to progress. It is extremely difficult to make the pitch for promotion or a loftier piece of work if that individual isn’t recognized within the company or by the leadership team.

“You can provide people with really interesting projects, where they have access to stakeholders they wouldn’t otherwise have access to. That might mean they have to speak to someone on the board or present to the board. If it’s something so strategically important for the business, people will notice that person within the organization. That is a way you can provide progression: get people speaking in places which gets them noticed.”

Lesson 4: Off on a New Journey

Having earned your stripes clearing a local farm of marauding goblins, your party is on the hunt for a new adventure, ideally one with more treasure at stake. There’s no reason to jump at the first opportunity that comes along. It would be foolish to charge in without working out what comes next, and even more importantly, after. Take time to gain information. That was a lesson Sullivan learned early on.

“I’ve tended to be very opportunistic about my role changes, I don’t come with preconceptions. If something gets passed to me, I will look at everything and have that first conversation. I’m very open-minded. When I do look at a role seriously, I think about what comes afterward. I don’t think about that role being the end game, I think about it as a stepping stone to my career.

“What comes next if I do this role? What does it unlock for me that I wouldn’t have access to if I didn’t do that role?”

Interestingly, people’s drivers tend to change over time. When first starting out, you’re happy to rid a farm of goblins, not for what it brings next but because it provides you a handful of coins and a story. But a true adventurer is always looking towards what is to come.

“When you’re younger, earning a bit less and in non-senior roles, you’re looking for more money, progression and a senior title,” says Sullivan. “But once you’ve pretty much achieved many of these things, it’s more about do I believe in the mission, are these people I want to work with, can I make an impact, do I have the opportunity to have a voice, and can I influence decisions? Those things are much more important for me now.”

Lesson 5: From Adventurer to Juggler

After many quests, you’re now one of the most venerable adventurers in the land. You’ve fought dragons and trolls, found treasures great and small, and even managed to rescue a princess (or prince). The question is, how do you manage your family and your land while continuing your great journeys? According to Sullivan, the key in a word is prioritization.

“Ruthless prioritization. I’m very keen to find the things I want to do. I’m not a slave to the business, just reacting to everything that comes across my desk. I am very ruthless about the things I will do.

“Other than that, I think carefully about what the things are I can focus on that will make the biggest impact. Where can I add value that others can’t? Where are the opportunities to really move the needle, rather than grinding and being a slave to the work that comes in?”

For young adventurers who don’t as yet have the same luxury to ponder such points, Sullivan’s advice is the same but different.

“It’s about stakeholder management. It’s about understanding what’s a priority and what’s not in everyone’s mind. Everyone’s own work will always be their priority, and they also want their work done first. It is about having a conversation with your stakeholders and making them understand how you see priorities for the business. We are one person and we have only a certain number of hours in a day.”

Sullivan’s lessons are for adventurers’ brave, new and old. If you apply them next time you come up against a dragon, you may be able to slay the fire-belching beast and claim the gold.