How long should you chase a prospect for?

How long should you chase a prospect for?

Most people give up too soon. A few chase for too long and in the wrong way. Getting this right is one of the most valuable things you can do for your sales results, because the gap between a lost deal and a won deal is often just one more well-timed follow-up.

But before we talk about how many times to chase, it's worth being honest about why prospects go quiet in the first place.

Why prospects don't get back to you

When prospects don't get back to you, it's easy to assume silence means no. Sometimes it does. But more often, there are specific and fixable reasons why someone has stopped responding, and understanding them changes how you approach the follow-up.

The most common ones I see are these. The initial outreach wasn't strong enough to make them want to respond in the first place. The follow-up has stopped, because the salesperson is waiting for the prospect to come back to them rather than staying in contact. Or the person they've been speaking to isn't actually the decision-maker - just someone they get on well with, who has no authority to move things forward.

If any of those sound familiar, the answer isn't to chase harder. It's to fix the underlying problem first.

How many times should you follow up?

There's no single answer that works for every situation, but here's a framework I've developed from working with hundreds of clients across different types of businesses. The numbers go up the bigger the organisation, and for good reason - the bigger the organisation, the more people involved in a decision, the longer everything takes.

• Solopreneurs: 3-4 attempts
• Small businesses: 5-6 attempts
• Corporates: 11-12 attempts, sometimes more

I've seen coaches say you should never follow up more than three times. I understand the logic, but it doesn't match the reality of how corporate sales actually works. Several of the corporate clients I've won - including Exertis, Terex, and Carousel Logistics - took between three and fourteen attempts before the deal was done. If I'd stopped at three, I'd have lost every one of them.

What following up actually looks like in practice

Here's a real example. A client I started working with came via a recommendation in April. Here's every step it took to get from that introduction to being paid.

• Recommended to them in April.
• Followed up by email. Heard nothing.
• A week later, sent useful content by email. Heard nothing.
• A week later, sent a video asking whether their priorities had changed. They set up a meeting.
• Two weeks later, we had the meeting. I sent a proposal.
• They went quiet.
• A week later, sent more useful content by email. Heard nothing.
• A week later, commented on the MD's LinkedIn post. She said thanks, nothing else.
• A week later, sent a recommendation from a previous client showing the results people get from working with me.
• It worked. The MD apologised - she'd been busy. A meeting was set for August.
• Won the client and invoiced them in August.
• Sent a thank you card in the post and a signed copy of my book, The Easy Guide to Sales for Business Owners, as a gesture of appreciation.
• They paid.

Thirteen steps. Several months. One client who has since become a great working relationship.

How to vary your follow-up so it doesn't feel like pestering

Look back at that list and notice something. Every touchpoint is different. An email, then useful content, then a video, then a meeting, then a proposal, then more content, then a LinkedIn comment, then a recommendation, then a card in the post.

That variety is deliberate. Sending the same email seven times with slightly different wording isn't follow-up - it's spam. What works is showing up in different ways, with something genuinely useful each time, so the prospect experiences you as someone worth hearing from rather than someone who won't take a hint.

The types of touchpoints worth rotating include direct emails, useful content relevant to their business, video messages, LinkedIn engagement on their posts, sharing relevant case studies or recommendations, and - when the time is right - something physical like a card or a book. Each one says something slightly different about who you are and how you work.

When should you actually stop chasing?

This is the question nobody wants to answer, but it's worth being clear about. You stop when you've genuinely exhausted the right number of attempts for that type of prospect, when every touchpoint has been varied and valuable, and when continuing would damage the relationship rather than preserve it.

Stopping doesn't have to mean burning the bridge. A final message that says something like "I don't want to keep filling your inbox - I'll leave it with you and please do get in touch if the timing changes" is polite, professional, and leaves the door open. Some of the clients who came back to me months later did so because I'd handled the end of the chase well, not just the beginning.

The goal is to be the person they think of when they're finally ready. That doesn't happen if your last message felt like pressure.

What to do when you finally win the client

Winning the deal is not the finish line. It's the start of the relationship, and how you handle those first few days sets the tone for everything that follows.

In the example above, I sent a thank you card and a signed copy of my book. Not because I had to, but because it's the kind of gesture that people remember. It costs very little and it tells the client immediately that they've made a good decision - that the person they've just hired pays attention to the details and values the relationship.

Most salespeople move straight on to the next prospect the moment a deal is signed. The ones who build long-term client relationships pause and acknowledge what's just happened. It's a small thing that makes a significant difference.

If you want to work on your follow-up process, your outreach, or how your team handles the full sales cycle, take a look at my sales training or coaching programmes, or get in touch and let's talk about what you need.