For years now, entrepreneurs have championed the mantra “fail fast, fail often”, or “fail forward” or “fail better.”

The idea sounds nicely counterintuitive and Ted Talk-y, plus Elon Musk and Richard Branson once said it. Needless to say, it’s been regurgitated and rehashed and retweeted ad infinitum.

But what if you’re trying to grow a small business with a limited runway, and you’ve got revenue targets to hit and skepticism to overcome? In my experience working with these types of companies, there’s usually real pressure coming from someone at or near the top to definitely, by all means, NOT fail.

I get it. Sure, it must be nice for the generously funded tech startups in Silicon Valley to have the luxury of working the kinks out in the beta version and reading user comments with detached amusement from their historic Mission District loft as they sip Cognac and feed caviar to their albino tiger, Blanca. (At least, I assume this is what Silicon Valley workers do.)

I’m not going to argue that small businesses should make it a point to start regularly failing with abandon on a grand scale, but there is a type of failure that is unavoidable and should always be leveraged: rejection from your market.

Generating Feedback from Rejection

Rejection sucks. It’s painful. As humans with egos, we tend not to dwell on these dark moments; instead, we try to protect our egos and move past them as quickly as possible.

But when businesses move on from customer rejection too quickly without learning from it, they miss out on an important opportunity to better understand the market.

Whether it’s a prospect who declines to move forward with the subscription after the trial period, the customer who switches over to a competitor or the lead who doesn’t place an order after trying the sample, these moments of rejections – as disappointing as they may be – are great sources of first-hand market intelligence should you choose to tap into them.

Reading and absorbing the feedback is the hard part; generating it is fairly easy. Once it’s clear that your prospect is no longer your prospect – or that your customer has moved on – send them a short email, automated and personalized if possible, and ask what happened.

Below is a sample of this type of email:

Subject: Quick question

Hi [NAME],

Thanks for trying our free trial; I’m sorry our platform didn’t meet your needs.

I have a question that, if you could answer, will help us better serve our clients: Why did you decide not to move forward?

If you can reply with your feedback, I’d really appreciate it.



This is just an example, but if you keep it simple and avoid pleading for their business or inserting any undercurrent of hurt or anger, most people won’t be bothered by this kind of question. It shows that you care about their opinion, and in fact, people generally like to know that their thoughts are valued. If they don’t want to share them with you, then they won’t respond – and there’s no harm done.

What You Gain from the Pain

There’s virtually no limit to what you might learn from rejection, but here are a few big lessons that you may walk away with.

  • Market preferences. Your market probably isn’t going to tell you what they don’t like about your product or service – unless you ask them. Yes, you’re asking for more pain – but this pain is good for you. Sometimes, what you think your market wants and what they actually want are two very different things. (There’s more to dig into there, but we’ll save it for another post).
  • Your competitors. When a customer moves from you to a competitor, it’s tempting to dismiss it as a moment of temporary insanity on their part because of course your competitors are inferior to you. Maybe that’s the case – or maybe your competitors are gaining an advantage in a way you wouldn’t know about if you didn’t ask.
  • Your tactics. Analytics are useful for assessing some marketing tactics, but they don’t always tell you the full story. For example, maybe your market likes your yoga studio, but they hate the fact that you send your entire list politically charged emails every week with no way to unsubscribe.

Acting on it

Here’s an example of how one of our clients recently turned rejection into a valuable learning experience. After sending out samples and follow up emails to prospects, our client received a very thoughtful response email from a prospect letting them know that though they liked the sample, they weren’t the primary decision maker.

Furthermore, this prospect also informed them that the process of choosing a new product took weeks – sometimes even months – due to the number of locations and regulatory guidelines that need to be taken into account.

From this one email, the client a) developed a clearer picture of who is involved in the decision making process, which has helped inform targeting, and b) recalibrated expectations about the potential timeline of sales cycles for similar types of companies, which allowed them to sharpen their projections and revenue forecasting.

Not all feedback will be equal, and not every potential customer has to be placated – some lost prospects are better lost because they weren’t good fits to begin with. But if you keep this feedback channel open, trends will emerge and insights will be gained that can be used to improve your marketing – and your business.

Digging into moments of failure and rejection may be painful at times, but when you’re using this practice to your benefit, there should be less of them in the long run.