You’ve done the work. You’ve taken your passion and talent and built an infrastructure around them. You’ve earned a following, putting yourself out there and creating a customer base by providing quality free content. You’ve invested time and capital into the hope of monetizing your unique expertise. All that’s left to do now is to convert this work into its ultimate reward.

It’s time to sell.

Or is it? Knowing when to solicit sales can be tricky and intimidating for new entrepreneurs. There’s a certain stigma to salesmanship, the product of generations’ worth of snake oil and pyramid scheming from “entrepreneurs” with the moral compass of a tapeworm. On top of which, even honest salespeople run the risk of seeming otherwise by being over-eager and pushy. All of this can make the transition from giving to receiving an awkward one.

When is it appropriate -and effective- to finally hit “send” on sales offers? How do you know when it’s time to convert the trust and authority you’ve earned into money?

There are a few schools of thought when it comes to the correct timing. Each has their advantages, but all of them have two things in common: that they include consistent, quality free content throughout, and that each sales offer include some kind of enticement, usually a coupon code or other discount.

Having tried different approaches myself, I know which one works best for my business. However, it’s worth exploring several options before deciding for yourself when the iron is hot enough to strike.

Option 1: On The Customer’s Schedule

Some businesses time their sales offers according to a schedule with each individual customer. After a certain number of content-only emails, an offer is sent, no matter what. The idea is that there’s a formula by which one can balance the free content/sales offer ratio in a way that usually leads to conversions.

The logic is sound. The opportunity to solicit sales should be something that the customer gives you in exchange for quality content. How many opportunities per how much content will vary, but the basic idea remains the same: as long as the customer enjoys your content, you have the right to do a certain amount of advertising.

While sensible, though, this strategy isn’t always effective. This is because the offers come arbitrarily. From the customer’s point of view, whatever offers are enticing after five emails are just as enticing after three, or seven. The offers, in this strategy, have nothing to do with any opportunity for them. They simply come like clockwork, and represent no particularly good time to buy other than a coupon code that’s being held back until they’ve endured enough content.

It may work for some, but for others this approach may be too impersonal to generate consistent sales in the long term.

Option 2: On Your Schedule

Others time their offers to the rhythms of their business. When offers come, they come to every customer on the email list regardless of how long they’ve been on it. They may come on a set schedule, as in a monthly sale. They may come as part of an effort to promote a particular product or clear inventory. Whatever the reason for the offer, it’s particular to the conditions of the business.

This approach doesn’t reward any particular loyalty, or require any commitment from the customer other than being on the list. It’s less aggressive than targeting customers individually, but more logical. It’s also more transparent; if customers understand that there’s a genuine reason for the offer, it’s no longer an arbitrary ploy. You’re simply letting them in on the fact that now is a good time to for them to buy, for specific reasons that benefit both of you.

This approach works because it’s honest. It’s less cynical than dangling offers like bait regardless of your business conditions. It feels more personal than sending offers out randomly. Because of this, it has the potential to make customers pay closer attention to all of your emails. It’s a way to time offers that encourages and relies on transparency, which encourages trust.

Option 3: Always, and Never

Finally, some business don’t make sales offers at any particular time, or on any particular schedule, or because of anything customers do or don’t do. They simply focus on creating content that is mostly salesmanship-free, and offer it to their base in the hopes that customers will decide for themselves to make purchases.

The blogs, videos, and emails in this strategy simply contain a footer or other link to a standing offer that anyone enjoying the content can make use of, whenever. It requires the least effort in terms of salesmanship. It’s the least aggressive strategy, the least proactive, and the least pushy or intrusive.

It’s also the least effective.

The fact of the matter is that customers who get nothing from you but content will soon see you as simply that: a source of free content, not a business. If no attempt at sales conversions are made, few will occur spontaneously. While it’s high-minded to think that customers who enjoy your content will come to you when they’re ready, the simple reality is that customers need to be reminded that great free content is only the tip of the iceberg, and that beyond it is something worth paying for.

Which strategy is right for you? Clearly, I’ve found Option 2 to be the most effective. Other businesses may reach other conclusions, but I find it to be in the perfect “Goldilocks zone” between overly aggressive and overly passive. It’s salesmanship, but it’s salesmanship based on the very essence of capitalism at its best: the honest search for mutual benefit.

Your results may vary. The key is not to look for the “trick” to timing your offers. Simply seek the best opportunities to exchange genuine value for genuine value, and trumpet them to your customer base. If you keep this principle in mind, the time to sell should reveal itself.