Free Chapter — You’re On Your Own

So your name is out there. You’ve shouted from the proverbial mountaintop. And hopefully, you’re starting to get some interest in your work.

This is where it pays to have a little bit of sales experience. If you don’t, the process might look like a lot of gladhanding, being enthusiastic when you don’t really care, and having uncomfortable conversations about money. And, I won’t lie, there’s a lot of each of those involved. But this doesn’t mean you have to sell your soul to run a solid sales program, especially if it’s just you at the moment.

To start, I’m gonna anticipate something you might be thinking right now…

Well, yes you are. Maybe you don’t want to be one, but you are.

The unfortunate reality is that a lot of us have our own ideas about what “sales” actually looks like. At its worst, every salesperson looks like a used car salesman: treacherous and duplicitous, trying to take your hard-earned money through unnecessary services and upsells, all done under the pretense of fabricated urgency. Faced with the idea of selling our own services, we can’t help but worry about becoming this person.

Well, yes you are. Maybe you don’t want to be one, but you are.

The unfortunate reality is that a lot of us have our own ideas about what “sales” actually looks like. At its worst, every salesperson looks like a used car salesman: treacherous and duplicitous, trying to take your hard-earned money through unnecessary services and upsells, all done under the pretense of fabricated urgency. Faced with the idea of selling our own services, we can’t help but worry about becoming this person.

But where that horrible potential exists, there’s also the opportunity to do things the right way. That idea you have in your head about the person you need to be to sell your business? Forget it. There may be a day in your business when you need to hire a professional sales wiz, but today, it’s just you.

With that in mind, let’s uncover some solid strategies to keep in mind as you approach sales scenarios.

In general: don’t pretend to be big

One theme that I will continue coming back to is the strength of being small. It’s so easy to feel the pull to pretend that you’re bigger or more experienced than you actually are. Just remember: this is the impostor syndrome in you speaking out. The little part of you that doesn’t believe you have the right to be here. The little part in you that will self-sabotage. This little part of you needs to fuck off.

There are many reasons why a smaller team and even a solopreneur will look attractive to your clients — adaptive process, less red tape, lower fees — but at the end of the day, I find that most clients find the directness and simplicity refreshing. What you see is what you get. You don’t need to check with anyone before making decisions. You aren’t hiding unskilled team members who will do the grunt work. Believe me when I say that sometimes a small team is a massive breath of fresh air.

Just remember that before you default to putting “We” on your website instead of “I”.

Owning the first meeting

With the interest in maintaining smallness in mind, let’s jump right into that first meeting.

First off, say “hello”. Perhaps follow up with “nice to see you”. If you’re feeling frisky, maybe even smile.

Alright, I’m kidding. You’re not that bad at sales (hopefully).

I am a firm believer in valuing personal connections above all else. This is why I often spend the first 15-20 minutes of a 30 minute meeting asking personal questions. Here’s the reality: almost regardless of which service you’re selling to people, you’re likely handing them a multi-month chunk of your life. I have clients I’ve been working with for years. Is it honestly worth it to do that with somebody you don’t like? And of course, this person should also at least pretend to like you back.

I love this part of running a consultancy. I get to meet new people every week and learn about their personal backstory, their family, their day-to-day life, their hobbies… and the key part here is that people are so eager to divulge. Another thing I believe is that most people spend a lot of their working day thinking about not working — even people who love what they do and are seemingly work-obsessed.

So, don’t be afraid for your first question to be “How was your weekend?” instead of “How can I help you?”. Of course, you can cut things off a little later in the meeting, clapping your hands together grandly and saying, “Oh, I guess we should talk about work.” But you’ve done the extremely hard work of forging a personal connection and making yourself memorable.

And of course, be a rigorous note-taker. This is a skill that will pay dividends later in this process. Even recording a call or grabbing a transcript is great.

The art of the fast follow-up

As I’m sure you’ll learn in that all-important first call, most clients come to the table feeling anxious and stressed about their situation. Your ability to truly listen and empathize with their concerns will always set you apart.

During that tail-end of your initial conversation, engage in active questioning. Ask things like, “How did you get to this point?” or “What would your goals be when working with someone like me?” Follow up with optimistic, forward-facing questions such as, “If we work together for a few months and you’re feeling much better, what would have changed?” This is your opportunity to be a journalist, digging deep to understand the full narrative of your client’s past, present, and aspirations for the future.

Earlier, I mentioned taking rigorous notes. Hopefully you’ve done that, because I find it helpful to follow up after sales calls with a “What I Heard” summary. This is a simple, point-form email I send on the same day following a call — 5-10 bullets that detail, in chronological order, the most important things I heard. This can be brass tacks business stuff, and also cheeky personal stuff that you learned.

Tie it all up with a simple “Did I get all that right?”, even if you’re sure you did. I can guarantee they’ll appreciate your dedication to hearing them, but also not making any assumptions about having them perfectly nailed down just from a single call.

Follow their lead, and the most underappreciated part of sales

Looking at all your notes, there’s probably a lot of information you can glean about the opportunity without even realizing that it might be valuable. These are the little nuggets that get dropped during the initial call or two that will inform how you proceed from here.

The main thing that all these variables will influence? Speed. Your ability to move fast as a small enterprise is so hugely underrated.

Think about it. If you have a call with them and they’re hurting, stressed, desperate for someone to come along and sweep them off their feet — and honestly, they probably are — moving fast could be just the superpower they’re looking for from a vendor. It’s so, so easy to hop off a call and think, “I’ll deal with the next steps in a few days,” but by then, you might have lost all the momentum and enthusiasm you had during that call.

So, if you sense urgency from the client, a simple email proposal that clearly outlines the terms and suggests an immediate start can be effective. Conversely, for larger projects involving a multitude of decision-makers and unclear goals, you might want to invest the time in crafting a polished, branded proposal that identifies any gaps in alignment.

More often than not, I hop off an initial call and say to myself, “Oh wow, they want to move fast — I should go write a proposal right now.” And when I have that instinct, I follow it. I don’t think it’s crazy to attempt to have a simple proposal in someone’s inbox an hour after a call.

The point here is: you want to pay attention to the details of the project at hand, but you also want to pay attention to their vibe, and make appropriate decisions about how you move them through your pipeline.

Stay straightforward

I’ll say it again: you don’t have to complicate things.

Sales often becomes unnecessarily complex because of preconceived notions about the process. You might feel caught between the straightforward approach of Paul Rand saying, “This is what it costs, and this is what you get,” and the pushy tactics of a car salesman in a cheap suit. I tend to see most people leaning toward the latter when they should be embracing the former.

Speed, urgency, and enthusiasm are your strongest allies. Show your clients that you understand this, and I really believe you’ll be finding yourself winning work more consistently than you ever thought possible.

Selling without pretending to be someone else.