Legal Voices: Jamie Pennington, Business Coach and Trainer

Learn who your fellow community members are and share in their journeys.

The Centre for Legal Leadership

Interviews: Legal Voices Series on 14/07/25

Jamie Pennington will be familiar to delegates of our 'Lead In-house Lawyer' course. 

The former Army officer is Director of training company, Pennington Hennessy and Business Development Lead at AI driven learning business, Qinect. Jamie is also a Visiting Professor at the University of Law.

Tell us about your journey from the military to business coaching

In the Army, where I started my career and went on to spend 19 years, my specialism was change management. I learned that the challenges were less to do with change, which is externally applied, than transition, the work of motivating people to do things differently.

When I left the Army with my MBA from London Business School, I began working with a friend who ran a change management consultancy. From there I joined one of my clients, a law firm. I love working with lawyers. Firstly, they’re clever - they get things quickly. Secondly, my focus on behavioural skills complements the cerebral nature of the legal profession. I can absorb what people say and explain it to others in ways that empower them to change their behaviour.

Later, I did a Masters in Coaching at the University of Warwick and have been coaching now for 25 years. Through my work with the University of Law I got involved with the in-house community. This led me to collaborate with CLL to develop the 'Lead In-house Lawyer' course.

How does training in-house lawyers differ from training private practice lawyers?

One big difference is the commercial aspect of the in-house environment. Yes, the in-house lawyer advises the internal client in line with risk profiles but they must also be trusted to give general business advice. They need to tailor their contributions around the bigger commercial picture and the organisation’s strategic goals. This means understanding the business at a much deeper level than a private practice lawyer advising a client.

The in-house lawyer needs to understand the minds, the motivations and the challenges of the CEO and all major stakeholders in the organisation. Another consideration for in-house lawyers is the need to let go of perfectionism. Perfection is the enemy of the good, so the ability to decide what is good enough is part of what I teach in-house lawyers.

What’s your advice to in-house lawyers looking to step up?

Accept that you’ll need to act like a GC and exhibit Head of Legal attributes before you’re offered such a role. Start by understanding your stakeholders in detail. For example, go beyond getting to know, say, the marketing director. Dig deeper to learn exactly what the whole marketing function does. What are its main challenges? What’s happening across the sector and how is that influencing marketing decisions? Find time for this. You’ll need to make a big investment in yourself as nobody will do it for you. Next, ask stakeholders what they want from a GC/Head of Legal.

The role varies hugely from one organisation to another, so knowing where to add value and how to manage expectations is critical. And find a mentor. I’m constantly blown away by how generous GCs are with their time. They’ll help you understand the pressures and challenges that come with the role – and decide if it really is for you.

What are the three biggest challenges facing in-house lawyers today?

Time is the first one. In-house lawyers need to balance the need to get things done quickly against the need to do them properly. They also need quality time with their bosses. Many GCs like to report to the CEO as that sounds important but too often struggle to get their attention. Sometimes it’s better to settle for one level down, such as the CFO.

The second big challenge is technology. In-house teams are far from the cutting edge when it comes to using tech and keeping stakeholders abreast of what’s happening in legal.

The last one is resourcing. In-house legal teams are an overhead. For this reason, they must plan and budget effectively, then communicate their achievements to the wider organisation, otherwise their budgets will be consistently cut.

To what extent will AI impact in-house teams?

A lot of routine work will be done by machines to a sufficient standard and this will reduce vacancies for junior lawyers. And with lawyers trained during the pandemic around two years behind those trained outside it, employers are questioning the value of juniors versus ChatGPT. However, AI can’t determine what questions to ask or lay the foundations of trust. The components of trust are credibility, reliability and intimacy and AI can’t replicate these. So the in-house lawyer needs to focus on critical thinking and relationship building skills. Lawyers see the world differently and can, when they enter the room, help people relax. 

What are your takeaways from training in-house lawyers?

I love seeing how eager in-house lawyers are to understand and add value to the businesses they work in. The quality of the questions they ask and the discussions they have among themselves show that they’re more than just lawyers. They’re curious and prepared to look beyond the parameters of legal to benefit from well-rounded learning. They’re ambitious, too. They genuinely want to progress and, as a result, engage in the sessions to greater extent than delegates in private practice groups.

I get a real sense of community with in-house. They care about one another. I liken private practice lawyers to golf players who focus on their own game. They come together once every two years to form the Ryder Cup team, then return to their own turf. Lead in-house lawyers, by contrast, continually foster a whole team mentality. 

Away from the office, how do you unwind?

I’m normally on the move, so I love reading as I can pick it up and put it down as time allows. At any one time I have a fiction, history and business book on the go. At home I love to spend time with my family, which includes our foster children. I’m also teaching myself to fly a drone. Its not as easy as you may think!

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