A few days pass and they start wondering whether they should get in touch. Another couple of days pass and now they're worried that following up will make them look desperate. Eventually they either send one of those slightly awkward “just checking in” emails, or they leave it altogether because they don't want to be a nuisance.
I've always thought this was interesting because following up in sales isn't the same as chasing someone. Done properly, it's simply the next part of the conversation.
And there is a very big difference between the two.
When following up starts to feel like chasing
I think we've all received the emails that say “Just following up on my previous email”, followed a few days later by “Just bringing this back to the top of your inbox.”
I'm not particularly keen on sending them because they don't really give the other person anything. What we're actually saying is “I'd quite like you to reply to me now.”
No wonder that can feel uncomfortable.
A good sales follow up has a purpose. It might clarify something you discussed, provide information they were waiting for, answer a question, or simply continue with a next step you had already agreed.
That isn't chasing. That's managing a sales opportunity professionally.
The best follow ups actually start during the sales conversation
This is something I've learnt over many years in sales. If you regularly find yourself wondering how or when to follow up, the problem may have started before you ever sent the email.
Imagine finishing a meeting with:
“I'll send you the information and perhaps we can catch up sometime.”
It sounds perfectly friendly, but what exactly happens next?
Compare it with:
“I'll send that across tomorrow. Shall we have a quick chat next Thursday once you've had a chance to look through it?”
Now both people know what happens next. Nobody has to chase anybody because you've agreed the next step together.
It's a tiny change, but it's one of those simple things that can completely alter how your sales follow up process feels. You aren't trying to manufacture another reason to contact somebody. You're continuing a conversation that already has some momentum.
Silence isn't necessarily a no
This is another area where we can make sales unnecessarily difficult for ourselves.
Someone doesn't reply and our brain helpfully fills in the gap.
They're not interested.
Maybe they're not. But perhaps they've got a customer problem, somebody is off sick, a project has gone sideways or your email is sitting somewhere underneath another 147 messages.
I've certainly opened emails, thought “I'll come back to that” and then completely forgotten about them. I suspect most of us have.
Your proposal might be important to you, but your prospect has an entire business going on around it.
A thoughtful follow up can actually be useful. And if the answer genuinely is no, that's useful too. I'd much rather know that an opportunity isn't going anywhere than keep it sitting hopefully in a pipeline for the next six months.
Give them a reason to hear from you
One of the simplest things you can do when following up in sales is ask yourself:
“Why would this person be pleased to hear from me?”
Perhaps you've remembered something from your conversation that might help. Maybe you've found some useful information. Perhaps you've thought of a better way of approaching part of their problem.
It doesn't need to be complicated. It just needs to have a little more purpose than “Have you made a decision yet?”
This is also why good sales conversation skills matter so much. When you've listened properly and understood what someone is trying to achieve, following up becomes much easier because you actually have something relevant to talk about.
Sometimes the problem isn't confidence. It's clarity.
I've spoken to plenty of people who tell me they lack the confidence to follow up. Sometimes that's true, but quite often, when we dig into it, they simply don't know what they're following up for.
That's a clarity problem.
If you know what the next step is, when it should happen and why it matters to the customer, following up becomes far less awkward.
It's a good example of why the three parts of Confident Selling™ work together. Clarity gives you direction. Confidence helps you have the conversation. Conversion comes from helping genuine opportunities keep moving rather than simply hoping they'll move by themselves.
So next time you're staring at an email wondering whether you're becoming a nuisance, ask yourself a slightly different question.
Am I chasing them for an answer, or am I giving them a useful reason to continue the conversation?
If it's the second one, follow up.
You're not being pushy.
You're doing your job.
Want a little help putting this into practice?
If following up is one of those parts of selling that you tend to overthink, there are a couple of ways I can help.
You can sign up free to the Confident Selling™ Sales Momentum app, where you'll find practical tools and activities designed to help you put more structure and confidence into the way you sell.
And if you'd prefer something you can keep beside you, Confident Selling™: The Core Guide goes much further into building a practical sales approach that doesn't rely on pressure or uncomfortable sales techniques. In fact, learning to follow up naturally without feeling awkward is one of the things I specifically wrote it to help with.