12 Scenarios Where Selling Strategy Prevents Headaches

Hopefully, you’ve read and implemented this 19-step cheat sheet for selling strategy. If you haven’t, I’ll skip straight to the punch line: I believe selling some form of strategy, ideation, or advice is an attainable, effective way for savvy freelancers to move up the value stream, make more money in less time, and future-proof their businesses in the era of AI.

This post covers specific situations where selling strategy saves you headaches and make you money.

First, though, let’s talk about the required paradigm shift.

Short-Order Cook Versus Trusted Advisor

My working assumption for years was that my clients knew what they wanted and that my job was to give it to them.

In that respect, I functioned like a short-order cook. When a client ordered double hashbrowns with American cheese, white toast, butter, jam, five strips of bacon, 4 sausage links, four eggs, and a 64 ounce French vanilla latte, my job was to give it to them. Vendors don’t push back. Knowing that they’re easily replaced, they do what they’re told.

Advisors and true partners, on the other hand, have a different mindset. They’re willing to disagree with a client’s “order” or prescribed course of action. They seek to protect positive outcomes, so when a client through cavalier attitude, stubbornness, or ignorance asks for a heart attack on a plate, the advisor points out how the client is acting against their own self interest.

Over 15 years’ worth of anecdotal data has convinced me that most clients, let’s say 70%, don’t make short-sighted decisions on purpose. The vast majority aren’t in the cavalier or stubborn camp. They simply don’t know any better; they’re ignorant. They may have an inkling of the what (the outcome), but most aren’t clear on the how (the strategy). If they had the clarity and expertise to come up with a better solution, they would have already done it.

This is true for everything from visual brand identity to SEO to marketing to operations. They’re not sure how to get from where they are to where they want to be. As the expert, you then have the opportunity to say, “Are you open to a different point of view? Here’s why I’d recommend against [a high-carb, high-fat, high-sugar, high-protein breakfast, clocking in at 3,000 calories and combined with a sedentary lifestyle].

I can tell you this, and you can acknowledge, “That makes a lot of sense. I’ve had some clients like that: dissatisfied or disoriented and unsure which trail leads out of the woods.”

Be forewarned, though: Most freelancers need time and reps before they can establish a permanent address in the advisor paradigm.

Why? Because we’ve built habits and structure—that is, muscle memory—around the order taker paradigm. When your commanding officer, the client, says, “Jump!” you’ve conditioned yourself to reply, “Sir, yessir, how high, sir?!” You may not be accustomed to nodding and responding, “Happy to jump, sir, but it seems prudent to put out that fire over there before we start our morning workout.”

Make no mistake, some clients will resist being more strategic.

I’ve always had a pretty good head on my shoulders. I was that kid who wanted to know why, and that curiosity about the inner workings of things and the reasons I was being asked to do something won me praise and got me in trouble. The mall cop with a chip on his shoulder responded to insouciance differently than the college professor who celebrated independent thinking.

Clients are no different when it comes to advisors who believe in the value of independent thinking. If you don’t respond with “How high?” to their every jump request, they’ll be confused, frustrated or even insulted. Others will respond with genuine enthusiasm to the logic of sharpening the ax before hacking away at the tree.

With the former, you have to decide:

• Do I shut up, take the money, and play the part of the good soldier?
• Or, do I continue to assert my point of view and potentially lose the gig?

I can’t make that decision for you, but I can offer an observation: The clients who don’t want to be more strategic at the beginning of the project and won’t invest in strategy delivered in tandem with your outside perspective won’t suddenly changed their stripes later in the relationship. They’ll always be reactive. You’ll get more of the same, and depending on your workload and finances, you may be content to be a glorified pencil or paintbrush. I took on plenty of projects simply to pay my family’s bills on time (usually).

Hold that thought, and put it alongside this one: Freelance long enough, and you’ll eventually have too much expertise, too well-defined of a point of view. You’ll know the patterns, and the personality types, and you’ll reach a crux. You can’t keep capitulating anytime a client says, “I want it my way,” because you know their way is counterproductive, ineffective, or even dangerous. You can’t in good conscience agree to give them what they want how they want it when they want it.

When you reach that crux, congratulate yourself. You’re now opinionated and ornery enough to be rewarded handsomely for your advice, and you’re gutsy enough to walk away from clients who won’t heed good advice, even when it hurts your pocketbook.

Those two things you’ll have to hold in tension: the need to make a living and the desire to make a positive impact.

Paid discovery is a good filtering mechanism.

One of the most deflating things about freelancing is the time and effort we put into building relationships with prospects who were never going to be a good fit for us. It’s easy to write it off: “That’s just the cost of doing business.” I agree with that sentiment up to a point. No one’s win rate with new prospects is 100%.

That’s a fact, but sigh-and-shrug resignation to this fact ignores the other options available to freelancers, namely selling some form of strategy before you sell a big project consisting mostly of implementation work.

What I’m saying is that you don’t have to create proposals for free all the time. You can charge for in-depth discovery. Paid discovery, or project roadmapping, accomplishes 3 things for freelancers:

1. It repels tire-kicker prospects who would gladly keep burning your time if you let them but were never going to pay you fairly for the big project.
2. It saves you the hours you must sink into creating comprehensive proposal for custom projects with no guarantee that you’ll win the project.
3. It gets you into relationship faster with those prospects who will pump the brakes temporarily and invest in a more strategic approach.

When can freelancers sell strategy? What are the “entry points”?

Now, the biggest obstacle to doing this isn’t finding clients who will pay for it. Of course, that’s the doubt that most of my 1-on-1 freelance coaching clients express to me at first: “None of my clients will go for this.”

My coaching clients are smart, capable, hard-working, and accomplished folks, evidenced by the fact that they can afford me, so I’m not knocking anyone’s intelligence. Their lack of success selling strategy wasn’t some inherent deficiency but a lack of training in knowing what to look for.

Imagine having a stall at a fish market, a big, lively one like you find in Sydney. Your specialty is Moreton Bay Bugs. How do you know when a customer is shopping for those out of a hundred other types of seafood?

Now, imagine parsing the many people roaming around the market. The lunch crowd have backpacks and purses. Buyers from restaurants might have some kind of cart carrying large coolers that can accommodate Ora King salmon from New Zealand.

The home cooks? They carry big shopping bags and small coolers, and that’s the group you target because they’re interested in quality over quantity and will pay a premium for it.

So, you train yourself to look for big shopping bags and small coolers. You get better and better and noticing the tell-tale signs of a customer who may want what you have to sell.

Selling strategy is like that, and yet unlike that because many clients who would benefit from strategy aren’t necessarily shopping for it. They may be problem aware but not yet solution aware. You must train yourself to notice the tell-tale signs of folks with problems that strategy can solve.

Here are or tell-tale signs or entry points where I sell paid discovery, or project roadmapping:

• The client wants to keep meeting as they try to make up their minds about budget.
• The client can’t give you a clear, ranked set of goals and associated priorities.
• The client struggles to communicate succinctly what the project even is.
• The client is sold on working with you, but you’re not sold on them!
• The client has many needs and no actionable plan.

In other situations, a one-off paid “strategy session” is what the not-sure-what-to-do doctor ordered:

• The client asks to pick your brain, get your thoughts, or ask questions about [your expertise].
• The client doesn’t have a business partner and needs a thought or sparring partner.
• The client has a budget but isn’t sure how to allocate it and connect it to goals.
• The client needs someone to identify creative solutions to various problems.

For the record, what you’re doing in each of these scenarios is consulting, and it’s valuable even if it’s easy for you.

Freelancers tend to undervalue ideas because we come by them so easily. However, many clients will gladly pay for your help generating, organizing, and improving ideas:

• The clients want help coming up with ideas for marketing, social content, products, anything.
• The client likes the way you think and wants unrestricted access to your beautiful brain.
• The clients wants help thinking through a new product, service, or launch.

Don’t get hung up on the word “strategy.”

Let me point out that “strategy” often doesn’t go by that name. Call it whatever you want: project planning, roadmapping, ideation, brainstorming, being a sounding board, vanilla ice cream made from unicorn milk with rainbow sprinkles on top.

I define strategy as the group of decisions somebody plans to make to get from where they are to where they want to be. Strategy answers the question, “How are we going to achieve our goals?” And, “What are we going to do and why?” And even, “How are we going to do that and when?”

What many freelancers I coach realize is that they’ve already been “doing” strategy for clients but not charging for it. Half the time, the burden falls to us to fill in the strategy gaps before we can do the job we got hired for.

You can start selling strategy even if any of the following are true:

• You don’t think you have the right personality because you aren’t combative.
• You don’t know how to solve all of your clients’ problems.
• Your current clients don’t come to your for strategy.
• You don’t think of yourself as a consultant.
• You don’t like being in front of people.
• You’ve always done strategy for free.
• You don’t have all the answers.

Since 2016, project roadmapping and the other strategy flavors have helped me bill for 100s of hours I otherwise might have lost to free discovery.

I, er, recommend it.

If you know this is something you need to start doing, then apply to join the private Freelance Cake Community. All of the advanced freelancers in it are exploring how to get paid for the advice they give and the way they think, not just their hard skills.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign (Group Coaching). Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.