How to have deeper conversations with your clients and win more work


Lawyers are client-centric by definition. They’re experts in their clients’ businesses and dedicated to meeting their needs.

Regardless of their industry, every client will be facing a huge array of challenges right now – from technological disruption, to sustainability, to shifting customer expectations, and more. So there are more potential ways for lawyers to help them than ever before – and new avenues for growth for law firms.

Here, Treehouse’s El Tong and Jennifer Ramsey from stage – a women-owned business development and marketing venture focused on relationships, revenue, and growth for legal services – share six tips to help lawyers have deeper conversations with their clients and identify other problems they can help them solve.

1. Go deeper with your research

Of course you’re already well-versed in your client’s business and their sector, but to take your conversation to the next level, adopt a mindset of curiosity. Go deeper with your research and try to find something meaningful about what they’re personally passionate about to talk about. What can you learn about their interests, both at work and beyond? What are they proud of?  

Curiosity doesn’t come naturally to everybody, but you can train yourself to be curious by developing a habit of preparing in this way. Gather as much insight as you need to feel comfortable having a really good, open conversation. Remember, it’s not creepy to look at someone’s LinkedIn page – it’s a compliment!

2. Have an open conversation

It’s human nature to go into a conversation thinking about what you need to get out of it. But then you lead with bias from the get-go. You frame the conversation around what you need and when that’s your focus, opportunities to expand the conversation will pass you by. This is where curiosity comes in again.

Instead of starting with questions about specific business needs or projects you’re aware of, ask broader, more open questions, such as:

What’s on your plate right now?

What’s on the horizon for you in the next few months?

What’s most important to you at the moment?

You can then build on what they say and show your genuine interest. You might say:

That’s interesting, can you tell me more about why that matters to you?

I’m interested to learn more, why do you think you’re struggling with that?

Why is this such an important issue for you at the moment?

By asking why, you give the other person permission to share more deeply. They’re more likely to tell you what else is going on, which you probably wouldn’t have known about otherwise.

When you approach conversations in this way, you naturally start to build empathy and trust, which puts you in a great position to start looking for solutions to challenges together. Rather than ‘touchpoints’ the stage team coaches its clients to think of these interactions as ‘trustpoints’, as it’s trust you’re seeking to build.

You might worry that you’re going to cross a line by asking someone these kinds of questions, but it’s all about getting the tone right. Keep it light and conversational and demonstrate genuine curiosity, and people will feel safe to share.

3. Silence is a powerful tool

It’s very tempting when you ask somebody ‘Why’ to feel the need to suggest possible answers yourself. But try to hold back. If you jump in and say ‘Is this happening because XYZ’ you will immediately steer the conversation in a certain direction, and you will miss the chance to hear their gut response and may miss opportunities.

There may be silence while they think about their answer, but that’s OK. Hold your nerve and see what comes. People are generally quite forthcoming, and especially when they can tell that you genuinely care.

Active listening is a companion of curiosity – they go hand in hand. It’s not an exact science but aim to speak around 10% of the time in a discovery conversation, as your main job is to listen and create a great conversation experience.

4. Co-create the solution together

Now that you’ve developed a shared understanding of the challenge they’re facing, you can naturally start exploring what a good solution could look like.

It’s not about putting all your offers and services on the table, but instead discussing what might help. If you have ideas for solutions, put them out there in a general way, without inserting yourself into it – for example:

I wonder how it would feel if you could plan out your caseload for the next year?

I wonder if it would be useful if you had an easy way to understand how that regulation change will affect you – what do you think?

So you’re suggesting a solution that might help, but you’re not presenting it as a deal you have to sell. This allows you to test the water and see if this is something they’re actually looking for, and to build towards an answer. Continue to hold the curious approach you’ve taken so far, and explore together what they might need.

Remember that you don’t need to work it all out in one conversation. If you’ve built a genuine rapport, you will undoubtedly be invited back to chat again, and then you can put forward how you can help.

A great quote to keep in mind is from Maya Angelou –

“People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

5. Follow up

Never underestimate the power of a thank you note! Whether it’s handwritten or an email, a thank you note is always worth sending. It’s a great opportunity to summarise the main points you discussed, and confirm any actions you took away and when you will come back to them.

Quick follow-up is another ‘trustpoint’ and a great way to keep that door open for future discussions.

6. Remain curious

We give a lot of thought to the questions we ask at the beginning of a relationship, but we need to maintain that approach throughout because situations change.

Even when you think you’ve agreed on a solution for a client, keep talking to them as you develop it. Keep checking in and get their reaction to what you’re building. Ask them: How does it make you feel? Can you give me your gut reaction to it? 

Too often people will put loads of time and energy into perfecting a solution, only to show it to a client and discover it’s not what they were expecting. Stay curious, keep asking questions, and you’ll land on a solution that gives you a happy client – and happy partners too.

At Treehouse, we help law firms get closer to their clients, differentiate in the market, and identify new avenues for growth. Find out more – and schedule a consultation with a senior member of our team.

More from the blog

8 lessons I’ve learnt from over a decade running a business

You learn something new everyday when running a business. That’s one of the many reasons I love it. Our ten year anniversary here at Treehouse technically happened in 2020. But, as you might expect, we […]

Read more
Managing Partner Magazine – Innovation Cover Story

Design thinking is new to legal services, but as innovation continues to rise as a top priority for law firms, the age of the ‘design thinking law firm’ may be upon us.

Read more
AI + human-centred design: Why you need both

The extraordinary rate of technological change we are experiencing right now is being felt in virtually every sector. With around 250 new artificial intelligence (AI) applications launching every week, the challenge to ‘stay current’ is […]

Read more
Read enough? Get in touch
Drop us a line to discuss the learning objectives you have for your people with one of our training specialists.

Let's talk

If you can spare the time for a 30 min ZOOM call, a member of our senior team would be happy to discuss your aspirations and challenges, and explain how we can help.

Send us a message

Please enter your name

We use HubSpot as our CRM platform. By submitting this form, you acknowledge that your information will be transferred to HubSpot for processing. Learn more about HubSpot's privacy practices here.