A lot of professionals prepare for client and prospect meetings by thinking primarily about what they’re going to say. They review their experience, recent matters, capabilities and credentials and prepare to explain why they or their firm would be a good choice. That preparation has its place, but it can also lead to a meeting where the professional does most of the talking and leaves knowing very little more about the person sitting across from them.
Some of the best client meetings I’ve been part of have been much more conversational. You ask a good question, listen carefully to the answer and then ask another question based on what you just heard. The conversation can go somewhere you hadn’t anticipated, which is often where you learn the most useful information.
Think about what you could learn if you spent more of a client meeting listening. You might hear about a business priority that hasn’t been publicly announced, a frustration with another advisor, an upcoming leadership change, an expansion plan, a problem affecting several parts of the company or an issue that keeps an executive up at night. You may also learn what the person cares about outside the immediate reason for the meeting and what kind of advisor they actually want to work with.
This is also why I’m such a believer in preparing questions before an important meeting. You don’t need to march through a list of 10 questions like an interviewer. Choose a few that make sense for the person and the situation, then let the conversation develop naturally. The best follow-up question is often the one you couldn’t have prepared because it comes directly from something the other person just told you.
Here are 10 questions that can help you have better client and prospect conversations and learn much more about the people with whom you want to build relationships.
1. What’s taking up most of your attention right now?
This is a great way to open up a conversation because it gives the other person room to talk about what matters most to them. Their answer could be a major business initiative, an internal challenge, a transaction, a leadership issue, pressure from management, a new market or something happening in their industry. You’re allowing them to decide what’s important instead of immediately steering the conversation toward whatever you came there hoping to discuss.
Pay attention to what they choose to tell you and ask follow-up questions based on their answer. If they mention a major initiative, ask how it’s going. If they talk about a challenge, ask what has made it difficult. If they mention something unexpected, explore it. You’ll often learn much more from the second and third questions than you did from the first.
2. What has changed most in your business over the past year?
It’s easy to assume we understand a client’s business because we’ve worked with them for a long time. Meanwhile, their leadership may have changed, their competitive landscape may look completely different, they may have entered new markets or their priorities may have shifted significantly since the last time anyone asked.
This question gives you a chance to update what you know. It can also uncover needs outside the immediate work you’re already doing. A lawyer may hear about an issue involving another practice area. A consultant may learn about a business problem outside the current engagement. You may discover that an issue that barely registered a year ago has become one of management’s biggest priorities.
3. What are you hoping to accomplish over the next 12 months?
Understanding what someone is working toward gives you a much better picture of where the relationship could go. They may be planning acquisitions, expanding into another market, hiring, raising capital, launching something new, changing leadership or dealing with a major internal initiative. Those plans can help you understand what they may need from their advisors in the months ahead.
The answer also gives you something meaningful to remember and revisit. If someone tells you that expanding internationally is one of their priorities, make a note of it. When you speak again, you can ask how the expansion is progressing or send them something relevant to it. That follow-up has context because it comes from something they actually told you mattered.
4. Where are you seeing the biggest challenges or pressure?
People will often tell you what they want to accomplish before they tell you what’s making it difficult. Asking about challenges gives you another part of the picture and can help you understand what may be standing between where they are now and where they want to go.
When someone mentions a problem that falls squarely within your expertise, there can be a strong temptation to immediately start explaining how you would solve it. Spend a little more time understanding the situation first. Ask what they’ve already tried, how the issue is affecting the business and who else is involved. The additional context can completely change your understanding of what they actually need.
5. What are you seeing in your industry that more people should be paying attention to?
I love questions that give clients an opportunity to share their expertise because they change the dynamic of the conversation. Senior executives spend plenty of time listening to people pitch ideas and services to them. Asking what they’re seeing in their own market gives you an opportunity to learn from them and shows that you care about their perspective.
The answers can make you better at business development too. You may hear about a shift in customer behavior, a technology issue, regulatory pressure or an emerging trend that hasn’t received much attention yet. When similar themes start coming up across several conversations, pay attention. Those themes can inform future client programs, articles, webinars, events and other ways of engaging your market.
6. What do you value most in the outside professionals you work with?
This is one of the most useful things you can learn about a client because different people define a great advisor very differently. One person may care deeply about responsiveness. Another may want someone who understands the business without needing everything explained. Others may value practical advice, predictable fees, candor, creativity, industry knowledge or an advisor who brings them ideas before they ask.
Listen to the language the person uses because they’re telling you how they want to be served. That information can help you adjust the way you communicate and work with them, and it can also help the broader team understand what matters to that particular client.
7. Where could your current advisors be more helpful?
Asking someone whether they’re happy with their current advisors can put them in an awkward position and may produce very little useful information. Asking where advisors could be more helpful creates room for a much more interesting conversation about what they wish they were getting.
You may hear that they want more proactive communication, better industry knowledge, more practical advice or stronger coordination among different advisors. You might discover a specific gap where you can help, but even when there isn’t an immediate opportunity, you’ve learned something important about what the person values and what they may be looking for in future relationships.
8. Who else should we be getting to know?
This is particularly important with existing clients because many relationships remain concentrated among a small number of people. If one key person leaves the company, retires or changes roles, a relationship that seemed incredibly strong can suddenly look very different.
Ask about other people in the organization who would be useful for you or your colleagues to know. There may be executives, members of the legal department, business unit leaders or other people whose responsibilities overlap with areas where your organization can help. At the same time, consider whether there are people in your own network who would be useful for the client to meet. Some of the strongest relationships are built when you become someone who connects people and shares your network generously.
9. What would be useful from us between meetings?
Professionals send clients an enormous amount of content without ever asking whether they want it. Client alerts, newsletters, webinar invitations and event invitations can all be valuable, but different clients want different things and have different amounts of time to consume them.
Ask what would actually be helpful. One person may want a quick note when an important development occurs. Someone else may appreciate industry data, introductions, benchmarking information or invitations to small gatherings with other executives. Their answer gives you a much better idea of how to stay connected in a way that feels relevant to them instead of relying on generic outreach.
10. Is there anything we haven’t discussed that would be helpful for me to understand?
This is a useful question toward the end of a meeting because your agenda and the other person’s agenda may be very different. You may have spent most of the meeting discussing the issues you expected to cover while something else has been sitting in the back of their mind.
Giving them an opening to raise another subject can lead to information you never would have uncovered through your prepared questions. Sometimes there won’t be anything else to discuss, and sometimes the answer will take the meeting in an entirely new direction. Either way, you’ve given the person an opportunity to shape the conversation before it ends.
What You Do After the Meeting Matters Just as Much
The value of asking better questions comes from what you do with the answers. After the meeting, take a few minutes to capture what you learned while it’s still fresh. Write down the person’s priorities, challenges, upcoming initiatives, important relationships and anything you promised to send or do. Put relevant information into your CRM or whatever system you use so it doesn’t disappear into your notebook and get forgotten.
Your follow-up should reflect the conversation you actually had. Send the article you mentioned, make the introduction you promised or share the information they asked for. If they told you about something happening six months from now, make a note to reconnect closer to that date. If they mentioned a conference they’re attending, think about whether you or someone else from your organization will be there. These small details make follow-up much more personal and useful.
There also may be no immediate business opportunity, and I wouldn’t consider that an unsuccessful meeting. You’ve learned more about the person, their business and what matters to them. You’ve also created information you can use to make the next conversation better. Business development relationships are built through a series of interactions, and understanding someone more deeply gives you many more ways to stay connected between the moments when they actually need your services.
Preparing Differently for Your Next Client Meeting
Before your next client or prospect meeting, look at your preparation from both sides of the conversation. Of course you should know what you want to discuss and be prepared to explain how you can help, but also write down three or four things you genuinely want to learn about the other person, their business and their priorities.
Then pay attention to what happens once the meeting starts. If someone gives you an interesting answer, stay with it instead of rushing to your next prepared question or bringing the conversation back to yourself. Ask them to tell you more, understand the context and remember what they tell you. That kind of conversation gives you much more to work with after the meeting and usually makes the interaction more enjoyable for both people.
Over time, the information you collect through these conversations becomes incredibly valuable. You understand your clients better, you start recognizing patterns across an industry, you see opportunities to connect people and you have better reasons to reach out between matters. Most importantly, your relationships become based on knowing what people care about instead of continually reminding them what you can do.
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