Helping Legal Leaders Thrive: A Conversation with Executive Coach Trinnie Houghton
In the high-pressure world of law, leadership often requires more than just sharp legal skills. It demands clear communication, resilience, and the ability to guide teams through complex challenges. Few understand this better than Trinnie Houghton, a Boston-based executive coach who has spent nearly 15 years helping senior attorneys, partners, and emerging leaders transform how they lead — and how they sustain themselves in demanding roles.
With a background as an attorney at top Boston firms and deep expertise in leadership development, Trinnie brings a unique blend of analytical thinking and human insight to her coaching. She has worked with clients across industries and continents, helping them navigate everything from team dynamics and enterprise strategy to mental health and career growth.
In this interview, Trinnie shares her insights into the unique leadership challenges facing lawyers today — and how coaching can help legal professionals at every level thrive in their careers while maintaining well-being and authenticity.
You’ve worked with professionals across industries — what’s unique about coaching lawyers and legal leaders?
I believe coaching leaders share many common threads across industries — after all, we’re all human. But what makes coaching attorneys unique is how they’ve been trained and the specific demands of their profession. A coach working with legal leaders needs to understand their context — from how they think and communicate to the values that guide their practice.
It’s been a privilege to coach attorneys. In my experience, many legal leaders tend to have a strong sense of duty — they care deeply about doing the right thing and protecting both their clients and their organizations.
One thing that stands out is how much attorneys appreciate well-crafted questions. They seem to enjoy thinking through prompts from multiple angles. When appropriate, I also bring in relevant resources or frameworks — they tend to value that kind of rigor and specificity.
What dynamics or challenges stand out in the legal space compared to other sectors?
A common challenge I’ve observed is the shift from a lawyer mindset to a leadership mindset. Lawyers are trained to protect, defend, and reduce risk — which serves them well in their practice. But that same mindset can sometimes bleed into how they manage people or influence organizational dynamics. The most successful corporate attorneys I’ve worked with understand this. They know their role goes beyond legal counsel — it’s about taking an enterprise-wide view and leading people effectively. They’ve learned to flex between legal expertise and leadership presence, navigating both their teams and the broader political landscape of their organizations.
Another dynamic I’ve noticed is that advancement opportunities in legal departments can be limited, depending on how the team is structured. That can create frustration for talented individuals looking to grow — and it’s often a coaching opportunity to explore influence, visibility, and long-term career strategy.
How do you approach mental health and well-being in your coaching work, particularly with high-performing legal professionals?
This is near and dear to my heart and not just limited to coaching attorneys. In most high-performing professions, the pressures of the job take a deep toll on well-being – not just mental, but physical, emotional as well. My experience has been to understand first whether the client leader understands how well-being fits into being better able to perform their job well, and what steps have already been taken. If they haven’t been taken, we talk about the cost of not doing anything. We talk about trade-offs at work. We talk about being intentional about what that would look like and what might result. We also talk about small steps, and what permission from themselves that needs to be given.
What are some strategies you’ve found effective for helping them manage pressure and stress?
(1) Being intentional. For example, planning vacations well in advance, blocking them on the calendar, or planning no-work weekends. (2) Getting outside. Walking in nature, whether it be a forest path or botanical garden. A corollary is having plants in your office or home. Research is replete with evidence on how being outdoors, or near trees or even pictures of them, can settle the nervous system. (3) Movement. This does not require a heart-pounding exercise routine, unless that is enjoyed, too. Walking and yoga are also helpful. (4) Seeing friends and building community. Spending time being with people that support you and make you laugh. Doing something you love outside of work with others also helps clear the mind and put things into perspective. There is much evidence on how rest, taking time away, or having fun doing something enjoyable makes us more productive when we return to work.
Ariel Group emphasizes leadership presence and authentic communication — how do those skills show up in the legal profession?
Attorneys are well-spoken and clear writers. Word choice is very intentional, and they excel here. My experience has been that leadership presence shows up best when they are aware of the whole enterprise. This means acknowledging other perspectives and building those relationships to do good work together.
Where do lawyers and firm leaders often struggle or thrive in this area?
My experience has seen lawyers struggle when other perspectives cannot be acknowledged and they seem stuck in a position, unwilling to budge. Or when genuine relationships are not built cross-functionally. Attorneys tend to thrive using their good communication skills. Very skilled attorney leaders leverage their communication through nuancing it to better understand, build rapport and contribute as a thought leader. At times, they learn to adopt a more informal tone when the situation calls for it.
You coach everyone from new managers to the C-suite. How does your approach shift depending on where someone is in their legal career?
Newer managers tend to focus on building their teams, developing peer relationships for leadership cross-functionally, delegating, and working through their teams. They are learning to put more emphasis on strategic thinking and influencing through others. More senior level partners/General Counsel positions are more focused on the business’s overall success and leveraging an enterprise mindset. They have developed relationships with peers, understanding the ways in which the business works together and where legal fits into a successful pathway forward. They also have a clear vision for their department, ensuring their team is working as a high-performing team. They attend to their direct reports’ development, and succession planning. They are constantly thinking strategically and using their connections to get things done.
Do you find certain leadership skills are more critical at the partner level?
My experience has been relationship building is key at the partnership or C-Suite level, as is the ability to think strategically and knowing how to lead through others. There can also be an emphasis on leadership in their community to build business relationships with those stakeholders and other sectors.
What leadership traits do you think are most essential for law firm leaders right now — especially as the industry evolves rapidly?
Enterprise thinking – the ability to shift into a business leadership mindset, staying open to other perspectives to forward the business’s priorities – seems to be essential across a variety of companies. Relationship building and management (influencing across) is equally as important.
There’s often a stigma in law around asking for help — whether for mental health or leadership coaching. Do you see that changing?
I’m not aware of such a stigma and have not worked with anyone for whom that was an issue. Perhaps by having a coach, they have already asked for help, and their firm’s/company’s culture has normalized coaching as an investment in high performers.
For law firms or companies where asking for help is difficult or not accepted by their culture, then this would seem infinitely more difficult for coaching. As I mentioned earlier, the very nature of legal work is one of justice and protection, so asking for help may be viewed as being too vulnerable, and that would seem too risky.
How do you help clients move past that hesitation?
If clients are unsure or hesitant, we take time to discuss all questions and concerns, especially noting confidentiality within the coaching engagement. I also might share other resources to help clients learn more about coaching first and give some small, safe options as to where to begin.
Law firms can be competitive environments. How do you help lawyers move from a focus on individual achievement to more collaborative leadership?
It helps to have a common project that they can collaborate on together, both within their roles and outside of them. For example, a cross-functional, co-associate, or co-partner initiative on a particular new law or regulation, educating peers or clients on new regulations and the impacts across the company or on clients, or co-leading a company initiative to mentor college graduates who aspire to be attorneys.
For law firm leaders investing in coaching, what does success look like?
I suppose it is different for each law firm, and/or legal department in a corporation. For some law firms, having senior associates and junior partners (high potentials) prepared to understand the business leadership aspects of running a law firm, as well as working well with their people. This might include delegating, prioritizing, building relationships and taking care of themselves to bring their best to work. It also might include strategies for building a book of business.
For corporate law firms, developing an enterprise mindset among their attorneys, having a team that is high-performing where attorneys work well together, and contribute in thought leadership. It may also include the legal department being seen as a thought partner in the enterprise. Additionally, it may mean developing a succession pipeline where direct reports develop leadership plans that they refine over the years. It might also include delegating, prioritizing, relationship building and appropriate self-care.
How do you measure the impact of coaching on performance or firm culture?
I would first define what does success look like to that company’s or firm’s culture. For example, are there specific leadership behaviors to be cultivated and celebrated? The coaching works best when it fits into those cultural values.
Typically, we measure the client’s current performance in leadership through a customized 360 that reflect those cultural leadership values. During the coaching engagement, feedback measures are built into a leadership plan with stakeholder engagement. Then towards the end of the engagement, we measure progress by selecting a few stakeholders and asking how much progress has been made (or not) in certain areas outlined by the plan. The client leader and those sponsors can determine where the leader is on their path at that point and what plans are made to sustain progress. Ideally, the coaching catalyzes leadership performance, which supports cultural values.
