How to Follow Up Without Becoming a Pain in the Ass

Hello, this is Mark Satterfield, and welcome to the Velvet Rope Playbook, tonight's chapter. How to follow up without becoming a pain in the ass. Jonathan Mercer had a $180,000 prospect sitting in his pipeline and he was slowly killing the deal one polite email at a time. Jonathan was 52 and ran a boutique leadership consulting firm in Atlanta. He'd spent the first 18 years of his career inside a Fortune 500 company, eventually becoming the guy they sent into divisions when talented executives had somehow stopped talking to each other. He was very good at fixing complicated people problems. He was considerably less comfortable selling himself. Jonathan grew up in a small town in Western Pennsylvania where his father owned a hardware store and believed there were two rules for doing business, return every phone call and never make anyone feel pressure. Jonathan had inherited both. So when Rebecca called well, the 58-year-old CEO of a family-owned manufacturing company contacted him about helping her senior leadership team, Jonathan was careful not to push. Rebecca was an interesting woman. Her grandfather had started the company with six employees shortly after returning from Korea. Rebecca had joined the business after Harvard Business School despite her father's suggestion that she spent a few years somewhere where her last name wasn't on the building. She eventually became CEO, grew the company to more than 700 employees and was now preparing her daughter to become the fourth generation of the family in the business. But the transition wasn't going particularly well. Rebecca's daughter and two long-time executives had very different ideas about the future of the company. Rebecca could see trouble coming and thought Jonathan might be able to help. They had an excellent first meeting. Jonathan proposed a six-month engagement for approximately $180,000. Rebecca told him this makes a lot of sense. Let me think about it and talk with a couple of people. That's when Jonathan's problems began. Five days later, Jonathan sent Rebecca an email. Just checking in to see if you had a chance to discuss the proposal. Rebecca responded that things were hectic and she'd get back to him. A week later, Jonathan tried again. Wanted to circle back and see if you had any questions. Nothing. Ten days later, another email. I know you're busy, but I wanted to keep this on your radar. Still, nothing. Jonathan began wondering what most people would wonder. How often should I follow up without becoming annoying? Should he wait two weeks, a month? Should he call instead? At what point does persistence turn into desperation? But I think Jonathan was asking the wrong question. Because the problem wasn't necessarily how often he was contacting Rebecca. The problem was that every time Rebecca saw Jonathan's name in her inbox, she knew what was coming. He wanted something from her. Had she made a decision? Was she ready to move forward? Could they schedule another call? Every communication created another small obligation, and eventually avoiding Jonathan became easier than responding to him. About three weeks later, Jonathan saw an article about family businesses where the next generation wanted to modernize the company faster than the existing leadership team was comfortable with. He immediately thought of Rebecca. He sent it to her with the two sentence notes. "Rebecca, I saw this and thought about our conversation. The section about separating disagreements over strategy, over succession struck me as being particularly relevant to what you're dealing with." Thought you might find it useful. No request for a meeting, no mention of the proposal, no just checking in. Rebecca replied twenty minutes later, "This is exactly what we are struggling with." That started another conversation. A few days later, Jonathan sent her three questions he thought Rebecca and her daughter should discuss before their next leadership meeting. Again, he didn't ask Rebecca to hire him. He simply helped her. Two weeks later, Rebecca called Jonathan, the engagement moved forward. There's an important lesson here if you're selling expensive services, particularly to affluent or highly successful people. People don't necessarily become annoyed because you follow it up too frequently. They become annoyed when every follow-up asks them for something. Have you made a decision? Are you ready to move forward? Can we get something on the calendar? After a while, you're not staying in touch. You're chasing them. So here's a practical rule that I like. For every follow-up where you ask for something, try to have at least two where you give them something. And it doesn't have to be complicated. You might send an article directly related to your conversation, introduce them to someone useful, share an observation you had after your meeting, send them a resource that addresses something they mentioned. You might simply write, "I've been thinking about what you said Tuesday. Here's something I think you should consider before you make a decision." That's a completely different kind to follow-up. You're no longer saying, "Remember me," you're saying, "I remember you." And that's an enormous difference. When you're dealing with successful people, a prospect can be genuinely interested in working with you and still do absolutely nothing for the next three months. They're traveling, they're selling a company, their spouse has an opinion, and another problem suddenly becomes more urgent. Or the issue you solve simply hasn't become painful enough yet. Just and readiness are not the same thing. That's why disappearing after two unanswered emails can cost you very good clients. But endlessly asking whether they're ready, ready can cost you those clients too. Your objective is to remain relevant without becoming a nuisance. And one of the easiest ways to do that is to make your follow-up useful. Jonathan eventually developed a simple habit. After every significant prospect conversation, he wrote down three things the person had mentioned that weren't necessarily about the immediate sale. The problem they were thinking about, something they were trying to accomplish, an issue affecting their industry. Those three things gave Jonathan reasons to stay in touch that had nothing to do with asking, "Are you ready to hire me yet?" And something else happened. Just began experiencing Jonathan's expertise before they hired him. Every useful follow-up quietly demonstrated how he thought, what he noticed, and what having him as an advisor might actually feel like. That's much more persuasive than another just checking in email. So the next time you're wondering how frequently you should follow up, don't obsess over whether it's been seven days, fourteen days, or thirty days. Ask yourself a better question. If this person sees my name in their inbox today, will they be glad they opened the message? If the answer is yes, you're probably not following up too much. You're simply staying valuable. And if you'd like my help, developing a client attraction and follow-up system that keeps you in front of great prospects without constantly chasing them, visit GetWealthyClients.com where you can find information about all my books, my programs, and even about how to work with me personally. And before you go, if you're enjoying the Velvet Road Playbook, make sure you subscribe so you don't miss the next episode. And if you know someone who's trying to attract more affluent clients and would find these ideas useful, please pass this episode along to them. It helps me grow the podcast, and hopefully it helps someone you know land a few more of the clients they really want. This is Mark Satterfield, thanks for listening to this chapter of the Velvet Road Playbook. I'll be back at you soon with something new, but until then, bye for now.