Reconnecting with Former Clients: Harvesting the Low-Hanging Fruit in a Way that Feels Comfortable

No one cares how much you know until they know how much you care —Theodore Roosevelt

Keeping in contact with past clients is a great way to build your practice. Former clients can be a good source of additional business and referrals. But if you are like most of the lawyers I coach, once a client matter has been resolved, your energy generally shifts to the next client or the next matter. Staying in touch falls way down on your priority list.

In my opinion, failing to stay in contact with former clients is a big missed opportunity for most lawyers. It takes a lot of time and energy to build a trusted relationship with clients. That trust is essential in getting clients to hire you in the first place. Once that trust is built, clients are likely to think of you if they have a legal need or if they hear of someone else who has a legal need.

Clients who know, like, and trust you are generally your best referral sources. If they were happy with your service, most clients are happy to make a referral.

The reality is that the opportunity to hire you again or make a referral is episodic. That is the nature of most legal work. It could be months or years before a client needs your services again or is in the position to make a referral. In the interim, the memory of the great work you did may fade.

Therefore, staying top of mind over time needs to be a critical part of your marketing plan. Knowing when and how often to follow up is an important part of that (see Persistence, Follow-Up, and Avoiding Fatal Attraction: Tips for Building Your Network).

Why Do Most of Us Drop the Ball?

If you are wired like many of the lawyers I coach, reaching out to former clients feels “salesy.” Many of us don’t like it when stockbrokers and other service providers reach out to us to set up a time to talk. It feels as if they are just trying to sell us something.

If your mindset is that you are reaching out only because you want more work from this client, then that makes sense. Your internal dialogue is going to be, “Client X is going to think I’m just trying to get more work from her.”

On the other hand, if you think about connecting as an effort to build the relationship in a mutual way, then it is easier to send an email to schedule a time to reconnect.

Another reason that many of us avoid reaching out is that we are not sure what to say once we are meeting clients for coffee, by phone, or on Zoom.

So here is the reframe: Reconnecting with a former client in a way that strengthens your professional relationship may open doors to new opportunities, but it is also a way to add value to the relationship beyond doing more client work. Doing so requires a thoughtful and tactful approach.

What follows are some suggestions about how to structure your follow-up conversations with former clients. By planning these follow-up conversations in advance, you can come to meetings feeling more comfortable and knowing that you will be able to give more value.

Approach Old Clients as You Would Old Friends

There is a good chance that former clients will be happy to reconnect. If you achieved a good outcome for them and provided good customer service, most clients are happy to speak. I generally recommend sending an email that goes something like this:

Hi, Jim. It has been a long time since we last connected. My apologies for being out of touch. I enjoyed working with you on [describe matter], and I’m curious about how things turned out with [describe]. I’d love to hear what you are up to and what challenges you are facing. I’m also trying to expand my business, and if you are open to it, I’d like to pick your brain about that. Are you free the third week of [fill in the blank] for coffee or a Zoom? I look forward to catching up!

Once you have your meetings set up, it’s time to prepare. Do your homework and think about the questions you might ask. Below are my suggestions, but there may be very specific questions that you can come up with based on your prior relationship, what you know about the person, and what you’ve read about this person’s company or industry.

General Reconnection and Updates

• How have you been? In many ways, this is the most important part of the conversation. Ask about their family or anything personal you know about them or their personal interests: Are you playing guitar? Have you been to any [name of sports team] games lately? How was your son’s graduation? How is your mom adjusting since your dad passed away? Ask if they have any vacation plans, if they did anything fun last weekend, or if they will be doing anything fun this weekend. Make sure to open the conversation in this way. But don’t forget to shift the conversation after a few minutes. If you have been keeping notes about the client in your contact manager, review your notes before you meet.
• What’s new with [their company] since we last worked together? Follow up with more specific questions based on your preparation for the meeting: How did things work out with [client matter]? I saw that [thing you read about the company in the news or company website, then ask a follow-up question about that thing].

Offering Value

• What are some of your greatest challenges right now? Depending on how they answer, ask lots of follow-up questions and be a great listener. Listen for ways you can be helpful. This includes referring them to resources or other contacts that might be helpful to them. These can be resources that are helpful to them professionally or personally (e.g., maybe you know a good plumber they can call, or maybe you can recommend a good restaurant or podcast.)
• What is a good introduction for you? This question is focused on helping them meet individuals who can help grow their business.
• Are there any resources I can connect you with? Here, you may want to be a little more specific based on what you’ve already heard. If you are being a good listener, you may find out that they are looking for another business resource or even a personal resource where you can be of help (this could be anything from an accountant to a house painter to an article on choosing a summer camp for their kids).
• A lot has been happening in [area of law where you counseled them previously]. Would you be interested in an article we published on that or in setting up a time to give you a quick briefing?

Exploring Further Collaboration

• We worked with you on [matter you worked on]. We would love to expand our relationship with [company]. Can I tell you about some of our firm’s other capabilities?
• Is there a project or initiative you’re excited about? How are you planning to tackle it? This can open the door for the client either to make referrals or identify more potential work for you.

Seeking Referrals and Expanding Network

• I really enjoy working with clients like you who are [describe qualities such as “innovative,” “forward-thinking,” etc. or describe their industry]. Do you know other professionals in your industry who might be facing similar issues or could use someone to bounce ideas off? Try to be somewhat specific about what a good introduction looks like for you.
• I’m trying to better understand the broader trends affecting your industry. Could you recommend events or groups that you find valuable for networking or professional development?

Ending on a Positive Note

• Thank you for taking the time to meet today. I look forward to staying in touch, and I am always here if you need anything. How can I best support you going forward? This reinforces your willingness to be a resource, regardless of immediate business opportunities.

Follow-Up and Summary

After the meeting, send a thank-you note summarizing key points of interest and any commitments you made. This keeps the lines of communication open and ensures that your client feels valued and remembered.

Mark in your calendar a time to follow up in the future (if nothing has happened organically before that date).

By focusing on building a relationship based on mutual respect and interest rather than just business transactions, you position yourself as a trusted advisor and a valuable network contact. That will keep you top of mind with other professionals, and ultimately, it will help you grow your business.