Stories about Software


It Turns Out Your Prospects Don’t Like When You Assume They’re Stupid

I’ve been traveling a lot lately.  And, while this is good for the vagabond’s soul, it’s not good for recording videos.

So instead of continuing to treat you to niche case studies (those are coming, though), I’m getting back to my roots and writing.  I’m going to classify this, like all of my other recent posts, as “business of freelancing.”  But it’s really a bit of an interlude, since it’s not a logical continuation of my last post, which was about how to conduct market research to identify niches.

For today’s post, let’s assume that you’ve either found a niche, or else are just flailing around as a generalist, and you’re doing some prospecting.  I want to talk about prospecting — specifically, one great way not to do it.

What is Prospecting?

Perhaps before we go barreling too far down the road to business acquisition anti-pattern, I should define what I mean by prospecting.

I’m not talking about going out and looking for oil or whatever, and I don’t really have a formal, official definition.  Instead, I’ll explain what this means to me so that you understand what, exactly, I’m talking about for the rest of the post.


  • Marketing is the process by which you create awareness of your offering.
  • Sales is the process of maneuvering leads (ideally, ones brought about through your marketing), through your sales process and to customers.

Clever readers may notice a gap here.

What if I don’t really have any marketing to speak of, and my phone isn’t ringing with inbound business?  How do I get leads into my sales process?

The various hustling you do to address this situation, dear reader, is known as prospecting.  (Please don’t confuse this with marketing.)

A Prospecting Example

If I were in your shoes, interested in learning about business concepts, I’d want a concrete example.  So, in true Golden Rule spirit, let me offer that.

My business, Hit Subscribe, is a specific kind of marketing partner.  We help dev tools companies make engineers aware of their offerings (usually via blog posts).  These days, I’m doing 2-3 sales calls per week, and here are the ways those come about:

  1. Inbound leads through word of mouth.  Current customers refer people they know, or customer contacts switch companies and bring us along for the ride.  This is an instance of marketing.
  2. People reach out because they read a guest post of mine somewhere or saw a talk.  This is another instance of marketing — specifically content marketing.
  3. I hang out places where our customers hang out, introduce myself, and forge relationships.  This is prospecting.

In the loosest sense, I think of marketing as strategies to facilitate passive (from your vantage point) awareness.  If Hit Subscribe impresses a customer into a referral, or someone reads a blog post I wrote and reaches out, we’re expending no specific effort to reach this person.

But prospecting is active and tailored.  You’re identifying and targeting possible customers.

And because you’re initiating the relationship, you need to exercise a lot more care in how you do this.  Which brings me to the meat of the post.

The White Knight Partner Anti-Pattern

Last week, I was minding my own business, when I received an email.  Er, more accurately, my spam folder received an email, presumably because “usamarketingexpert.com” just screams “non-US-based spam.”

Here is the meat of that email, one that anyone who owns a website with non-trivial traffic sees all the time.  I’d been looking for one in my spam folder, specifically to walk through for this post.

When I read this, I nearly spit out my coffee.  Heaven forfend!

I had no idea that I was “losing lots of traffic and conversion,” but I had to start fanning myself because learning this positively gave me the vapors.  Luckily, Willium and his crack team of “consultant” were there to swoop in, resplendent in their shining armor, and white-knight me squarely in the face with a Black Friday special.

And then our hero rode off into the sunset, taking his website, domain registration, and any trace of being a real company with him.  Farewell, mysterious champion.

Deconstructing The White Knight Tactic in Detail

Let’s set aside how comically spammy this message is because, honestly, that’s a distraction.  You’re probably laughing at this for the obvious typos, the fact “USA Marketing Expert” copy was clearly not written by a native speaker, and the textbook race to your inbox’s spam folder.

But you’re also probably going to do something like this to prospects without even realizing it, if you’re not careful.  You’ll just do it with a more tailored message and better grammar.

So to avoid that, let’s unpack with a bit of a play-by-play of the implications.  Here’s the gist:

  1. Dear person I don’t really know: you have a problem, but you’re too naive and inexperienced to realize it.
  2. Luckily, I came along and was able, at a quick glance, to figure out your biggest issue.
  3. Now, since you clearly have nothing better to do, let’s schedule a call to discuss my various notes for how to fix your business.
  4. And since you have nothing better to spend your money on, I’m certain we can come to an arrangement.

Notice that there’s nothing specific to spammers and SEOs in the abstraction I’ve created here.  It’s the same prospecting (anti) pattern used by MLMs, shady auto shops, and people looking to pay the bills the world over.

And it’s also used by freelance software developers.

Don't sacrifice your positioning strategy to code-jousting sites, as illustrated by this joust-ready knight.

What the Freelance App Dev White Knight Looks Like

If you’re failing to make the leap, let me walk you through a very plausible situation.  Let’s say that you, a web developer who favors Rails, happens on a SaaS that you’re signing up for.  And, from a flaky oAuth implementation to a terrible user experience in the info capture form, you note all sorts of substandard tradecraft that they need help with.

And this mediocrity will not stand, Man.

So you reach out.

  1. Dear SaaS company: you suck at writing software.
  2. Luckily, I’m a software developer with opinions, and I know what you need.
  3. Would you like to schedule a call so that we can discuss how I’ll go about fixing the various errata that I’ve noted?
  4. My hourly rate is normally $100, but I’m passionate about this, so I’ll discount it to $80.

This all seems perfectly reasonable to you.  But to your prospects, you look like Willium.

If you’re lucky, they’ll notice you enough to get annoyed or have a laugh, but they’ll probably just delete your message after barely skimming it.

Salaried App Dev Teaches You a Bad Lesson.  Unlearn It.

I’m planning to do a post, at some point, about the attractive nuisance of labeling and branding your work as “high quality,” so I won’t spend too long on this digression.  But I would like to briefly explain why freelance engineers are so likely to blunder into this play, like someone that can never remember whether the castles move diagonally or straight.

The entire software engineering job application and promotion process is founded squarely on a barely plausible veneer of meritocracy.  Theoretically, 20 programmers interview, and the “best” one earns the job.  And then everyone in the department codes away for a while, and the “best” programmers earn promotions.

So it is any wonder that we lurch out awkwardly into the business world, trying to earn business by “besting” our prospects in some kind of imagined programming skills competition?  Is it any wonder that our every instinct tells us to “win the job” by flashing superiority, not just to other candidates, but to the engineers on staff?

“Don’t try to win business from people by telling them that they’re dumb and you’re smart” seems glaringly obvious… in every context but our own, as engineers.

From the Prospect’s Vantage Point

One thing that I’ve notably elided so far, except obliquely, is the prospect’s rebuttal, were the prospect to bother.  Mostly, they won’t, but let’s assume, for rhetorical sake, that someone held a gun to their head and forced them to deal with your simultaneously desperate and arrogant overtures.

Rebuttal Example: Willium on DaedTech’s SEO

If I were to bother explaining the situation to Willium, and assuming he wasn’t a Drift bot or something, I’d say this:

Hello, Willium, and thanks for your good intentions, however naively expressed.  In the first place, DaedTech has minimal commercial interest, and isn’t aimed at earning revenue.  And, inasmuch as the property generates any revenue at all, it’s through book sales and the fact that my audience is largely follower/influencer based, rather than organic and transactional.

So, to recap.  You’ve completely failed to understand the purpose of my site, the nature of my audience, my goals in creating content, and, come to think of it, pretty much everything.  So, as sweet a deal as Black Friday blowout consulting for $150 sounds, I’ll have to reluctantly pass for the moment.

Rebuttal Example: The Rails SaaS

Now, let’s consider what the founder of the SaaS business might say to your notes, in a realistic hypothetical world.  I’ll do this one as a list, since there are any number of reasons that they might not avail themselves of your services:

  • We don’t have any budget for additional contractors.
  • The team is already working on a holistic overhaul of the onboarding workflow.
  • The fact that you didn’t like the onboarding experience doesn’t mean that anyone else doesn’t like it.
  • Though experience isn’t the best, it’s not actually causing abandonment during sign-up, so it’s not worth fixing right now.
  • The fact that you can recognize a bad user experience in no way qualifies you, ipso facto, to fix the problem.
  • We’re actually pivoting to an entirely different business model (but can’t say so).

I could go on, ad infinitum.  And that’s important, because it means that the list of context you lack stretches out into infinity as you sit there, armchair quarterbacking, in the hopes that this person you’re insulting will give you money.

What To Do Instead: Prospecting Like a Non-A-hole

In a lot of cases, it’s far easier to call out the problem than to offer constructive solutions.  This isn’t one of those cases, luckily.

It’s a straightforward, two-step process:

  1. Stop telling people what’s wrong with what they’re doing.
  2. Start asking people what they’d like help with.

What you’re trying to do as a freelancer is to make sales.  And, however much we like to kid ourselves that we and others make logical buying decisions — that we carefully and soberly weigh all options and then pick one based on merit — we make buying decisions emotionally.

Fear-Based Sales Isn’t the Path to Joy

When you dial up the ol’ White Knight Partner anti-pattern, the emotion you’re (probably unwittingly) trying to leverage is fear.  You make your buyer afraid and then try to inspire relief by offering a solution.

And, from the world of salaried app dev, this is particularly ironic, since you probably think that you’re trying to inspire confidence and trust.

Trust-Based Sales Is

If you want to make sales based on confidence and trust, however, you need to go with option (2).  Ask people how you can help.

A good marketing apparatus (or word of mouth referrals) will build trust ahead of time, which is why those are ideal.  But if you don’t have that, you need to build trust during the prospecting process.

That’s admittedly not the easiest thing to do with strangers, in a short time window.  Nevertheless, it’s the effective thing to do.

So your task, as a prospector, is to start thinking of how you can give free value, inspire trust, and help your prospects.  And that doesn’t start with insulting them and trying to cow them into cookie-cutter solutions.  It starts with making an effort to understand them.