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Sales Fundamentals: 4 Steps to Dramatic Improvement

Sales Fundamentals: 4 Steps to Dramatic Improvement

Liston Witherill
Liston Witherill
17 min read

Not everyone needs to be the best at sales. But every business owner, consultant, and professional service provider needs to be good enough at sales to close the clients they should.

In this article, you’ll get just the fundamentals of selling.

Not as in, “I don’t have any understanding of how sales works.” But as in, “I understand sales, and there’s more to learn than I actually need, so what small set of actions can I take that’ll have the biggest impact?

Think of the sales fundamentals like the 80/20 of sales. Only the smallest set of things you can do that’ll make an outsized impact on your success in winning new clients.

And there are exactly four skills that I’d map as mission-critical to radically transforming your ability to sell, in any environment, and to any client:

Chapter 1: Agendas and Next Steps

When I was very early in my career, a year or two out of grad school, I took Sandler Sales Training as part of my leadership role. Most of the training was outdated, like aggressively pushing your client to make a decision on your timeline. No thanks. But some of it was timeless.

You should always have an agenda on every call, meeting, or interaction you have with a client. It’s certainly the polite thing to do, and ensures you won’t be wasting your own time, or your clients.

But it also forces you to think about what should be on the agenda. As in, at any given stage of your sales process, what are you trying to achieve? Closing a deal is a moment in time. Reaching that moment requires a series of actions and decisions.

Securing Commitments

What you need is escalating commitments from your client in order to move a deal forward – what are they? The commitments you need from your client and when – that goes on your agendas at different stages of your sales process.

Agendas also force an important principle of persuasion called consistency. We like to act consistently with the commitments we make. When we do, we’re seen as trustworthy, which is important for our social capital and thus our survival. Everyone but the sociopaths among us want to be seen as consistent. Which leads to the age old wisdom, “don’t be a sociopath.”

When you use agendas and gain the commitment of your prospects, they’ll be more inclined to act consistently with their commitments.

So for example, if you say “by the end of the call today I’d like to know if you’re interested in working together,” and your client agrees, you’re more likely to get an answer from them. That’s the power of an agenda, and that’s the power of consistency.

Defining Next Steps

Related to an agenda is next steps. Agendas are done at the beginning of your calls, while next steps are always set at the end of your calls. Both reflect the things that need to happen in order to execute a deal to conclusion, win or lose.

The reason next steps are so important is that they give both you and your client tremendous clarity in the buying process. In order to tell your client what comes next, you must have a roadmap in mind.

Think about Google Maps. If you’re going out for dinner – back in the day when that was still a thing – you needed to have a destination in order for Google Maps to tell you where to turn next. You had a current location, relative to your destination, and a series of steps – turns – that would eventually bring you to your destination.

In the case of selling, your destination is a yes or no decision. Your next steps – the turn-by-turn directions you give your client – will allow you both to reach the destination faster.

In practice, next steps should be set and agreed upon at the end of every call or meeting. This summons consistency, once again, and will accelerate the decision-making process for your client.

It’s easy enough to understand, but the real skill comes in making it feel seamless to your client. Or dare I say, even natural. I can hit a forehand just like Serena Williams can, but her years of practice, coaching, fine-tuning, and drive make her forehand…well, better than mine, to say the least.

Set agendas, set next steps, do it every time, and it’s the single biggest change you can make that’ll help you dramatically improve the way you sell. For more on how to do this, check out The SDS Method – a complete sales process for professional services.

Chapter 2: Asking Probing Questions

“Peeling back the layers of the onion.”

I don’t know who decided on that phrase, but it’s something you have to do in sales. You could also think about it as “digging deeper.” However you think about it, what you see on the surface isn’t necessarily the same as what you’d see under the surface.

Dr. Gregory House – the fictional, curmudgeon-of-a-doctor on the TV show House – would tell his staff that everybody lies. It was a sort of golden rule that he lived by. He mostly meant it literally, but I give people more credit than that. Some lie consciously, but most tell lies of omission. When you’re working with a client, they don’t know necessarily know what’s most important for you to know, and what they can skip over.

Which means it’s up to you to ask good questions and keep probing so that you learn everything you need to. But asking probing questions isn’t just about what you can learn. When you ask sharp, open-ended questions, your client will have plenty to learn, too.

What Questions Do to the Brain

Let’s nerd out on the obvious for a second. What happens when someone asks you a question?

Well, first you’re trained to answer them. It’s the polite thing to do. Your mind focuses singularly on finding and articulating an answer. You begin searching the depths of your brain, your thinking hijacked by the question you were asked. It’s difficult for you to focus on anything else until you find and offer a response.

The same thing happens to your prospects. When you ask them a question, they’re instinctually and involuntarily searching for an answer. And that answer may surprise them. It may cause them to experience something from the past. And it should always elicit an emotional reaction.

And that, my friend, is critical because asking the right questions can give you everything you need to get a deal done. Things like:

  • Insight into the pain your client is experiencing
  • The motivation for your client to make a change (you know, to buy from you)
  • Whether there’s urgency for your client to implement a solution, and when
  • Your client’s ultimate goals, and what it’s worth for them to change, financially and emotionally

Leading Your Clients to Insights

Asking good questions means open-ended questions that will lead your client to self-discovery. It’s like the Socratic method of selling: rather than telling your clients what they should do, asking the right questions can lead them to the conclusion on their own.

Let’s use an example relevant to our relationship. Here’s a question for you, and I’d like you to think about it and respond in your head:

Do you ever lose deals with clients you know you should close?

It’s a yes or no question, with only three possible answers: yes, no, or maybe. I’ll reframe it, this time as a why question, since we all (me included) occasionally lose clients we should close and I already know the answer is yes:

Why do you think you lose clients you know you should close?

When you’re asked a why question, you’ll almost certainly respond with a “because” answer. The problem with why questions is that everyone will attempt to provide a cause-and-effect explanation, but “people are generally not very good informants about the reasons or causes of their behavior.”

As House would say, “everybody lies.” But in this case you’re supposed to be House, and House would never ask a client to diagnose themselves. That’s your job, dear expert. So let’s reframe this question once again, this time as a “what” question:

What steps are you taking to ensure you close clients who are a good fit?

Now we’re getting somewhere. I’m still looking for the same information, but the slight changes in the question will lead you to a much more information-rich response. I’m not looking for an explanation as to why you’re not closing more clients. I’m asking you a question that you’re well-qualified to answer: what you’re doing now. Anyone can answer this question truthfully enough to make House proud.

Finding the Depth of the Problem

As you dig for an answer – peel back the layers of the onion – you’ll be more inclined to discover a bigger, underlying problem. In this case, that you’re not sure which steps you should be taking, or that you’re not taking the right steps consistently, or that you’re not taking enough steps, or….

You get the idea. When asked properly, a question can focus the mind and shine a light on a problem that can grow in size and importance.

But it’s not enough to just ask good questions. You have to listen, too. You have to give your client a chance to fully and completely answer without interruption or derailment. Obviously. But here’s the thing: in the course of a normal conversation, most people are inclined to turn the conversation back to themselves. They “listen,” insofar as they quietly wait their turn to talk again.

The reason is that we all have a deep need to be liked. Unfortunately, being liked isn’t enough to win new clients. Neither is being right, which is a related drive to “sound smart” and be accepted. It can help, but articulating and harnessing your client’s motivation to change is far more powerful than being liked. And it’s even more powerful if they discover their motivation on their own: their pain, goals, and the value of changing.

And that, in a nutshell, is the importance of asking probing questions.

Chapter 3: Knowing Your Value

I was listening to a podcast over the weekend and was struck by a story about a guy who went camping with his friends.

One of his friends is ultra wealthy, with over $1B to her name.

Someone on the trip brought a boomerang. They all took turns throwing it. When the $1B woman took a turn, it was clear she had plenty of money, but not much in the way of throwing skill.

One of the other campers said to her, “in a hunter-gatherer society, you’d be a gatherer.” The skills she used to amass over $1B in wealth didn’t translate into throwing a boomerang, and she’d probably make a poor hunter. In one society she may have starved, but in today’s society she can afford to pay a live-in chef to cook three gourmet meals every day.

Luckily, she doesn’t have to be a hunter to get her food. She can use her money for that.

Her value as a member of society is highly contextual.

How to Get Paid What You Deserve (Without Negotiation)

The value you provide is highly contextual, too. For some people, your value proposition will be an absolute no-brainer, but others may find it less compelling.

When you sell, you must know your value to get paid what you deserve. And value is defined as “the importance, worth, or usefulness of something.” Take each one of those components separately and you’ll quickly find that the word “value” means a lot of different things to a lot of different people.

I’ll show you.

Think about your least favorite fast food restaurant. How much would you pay them for a meal right now? Probably not much – maybe they’d even have to pay you to eat their food.

Now imagine you’re starving. Your stomach actually hurts from the hunger pains. All you can think about is eating something – anything would do. You start having delusional thoughts about eating socks and couch cushions. Then you find the only place in the world that would serve you a meal: your least favorite fast food joint. How much would you pay for that same meal that you would’ve refused under normal circumstances?

If you’re hungry, you’ll pay more for food, and you’d even consider eating things that you’d otherwise refuse.

This is the importance of pain in the sale. It’s far more powerful as a motivating force than gain – an effect that’s well-documented. I’ve recorded a podcast episode about it, and it’s core to my training. Simply put, if you can’t identify and deepen your client’s pain, they’ll be less motivated to make a change.

Selling Is Just Change Management

And that’s what you’re proposing whenever you sell: a change. The trouble with change is that it’s really hard. Information isn’t enough for most people to change. There’s something called the status quo bias, which simply means we prefer to keep things the way they are. There’s inertia. And new information on its own won’t change us.

Is 42% of America obese because of a lack of information? For some maybe, but mostly not. People know that if they just ate healthy and exercised, they’d lose weight. They also know that In-N-Out Burger doesn’t serve health food. So what’s going on then?

The clue is in the definition of the status quo bias (emphasis added):

The current baseline (or status quo) is taken as a reference point, and any change from that baseline is perceived as a loss.

To overcome the status quo bias, the loss of doing nothing must be greater than the loss of change. Not that we’re all little value calculators – far from it, actually. I’ll demonstrate.

The Myth of Rationality, and How We Really Buy

I’ve been working on the side yard at my house. The house is a corner lot and sits closer to one corner than the other, so we have a strip of land next to our garage that could be a patio, but instead was used as a garbage dump. Literally – we’ve found broken bottles, rusty metal, and other artifacts of yesteryear there.

Being the ambitious person I am, I convinced my wife that we’d take on the whole project ourselves. That meant: removing all of the weeds and plant life, cutting down a tree, tilling the soil, grading the whole area, putting down a layer of gravel, adding a layer of sand, installing pavers, filling in the cracks with more sand, building a fence, adding planters, making a rain garden…and that’s just the stuff we know about going in.

So I got a quote from a contractor who can do it all for us. We expected something over $10k for the project. He came in with a quote of $8k. Done deal.

Notice that I originally set out to do the whole project without help. It was only after my wife and I spent several weekends working on the project that I was open to paying someone to do it for us. It’s a lot of work! And as for our decision-making process, it was way more emotional than rational. Here’s what a rational decision process would look like:

  • Calculate the cost of raw materials
  • Estimate the time it would take to do the project, and multiply that by the value of our time
  • Do an opportunity cost analysis to see if we could spend that time in a more valuable way
  • Calculate how the patio would impact the value of our home
  • Collect as many quotes as we could to choose the highest value contractor
  • Line it all up on a spreadsheet and make a completely rational decision based on cost-benefit analysis

Of course our actual decision process looked nothing like this. Here’s what actually happened:

  • We tried doing the project and learned it was really hard work (especially compared to typing this email)
  • We began planning out the project by picking the kinds of fences, pavers, and other materials we liked
  • We dreamed about having coffee, friends, and BBQs on the patio
  • Our vision of the patio was so compelling that we decided having a patio would be awesome and we desperately wanted it
  • We then rationalized our decision by saying it was a good price and it’d be worth the money to have it done right, and done this summer so we could use it

Now, some of your clients may make decisions the first way, but it’s incredibly unlikely. I felt the pain. I called the contractor. He could solve all of the pains I was going through, and I was emotionally motivated to do the deal. The monetary value of the patio is ancillary – just a story I told myself to feel good about the purchase.

Value Is Emotional First

The value you provide is economic and emotional, and the deeper motivation comes from the emotional stuff you do for people.

For this contractor, the real value he provides is bringing families together for BBQs so they can spend quality time together. He gives me another place to work when I can’t go to the coffee shop during social distancing. He gives us more pride in our home. He gives our dog a place to run around like a maniac. And he takes over the hard physical labor and know-how it takes to build the patio.

Sure, it may add some value to our home, but that’s only one small piece of it.

Knowing the value that you provide is critical in having the ability to tell a transformational story like this to your clients.

And that’s exactly what I want you to do. For more on this topic, check out my article on value-based selling.

Chapter 4: Telling Transformational Stories

I visited Rome, Italy and took a bike tour of the aqueduct system. The cobblestone roads weren’t the best, but they were original, so we were riding over history.

The immensity and scale of the aqueduct system is stunning, even now. Aqueducts stretched hundreds of miles across Rome, dotting the landscape with arches to deliver water wherever it needed to go.

The first of the Roman aqueducts was Aqua Appia, built in 312 BC, along the Via Appia military road in the city. This first, unsophisticated aqueduct stretched over 10 miles.

How do you sell such a high-risk project?

It’s unclear, because it’s missing from the historical record. But here’s my guess: you tell a story.

A story about erasing drought in the city. A story about improved sanitation, carrying away waste and disease, and keeping Romans healthy so they’re stronger soldiers. A story about how the aqueduct would make the citizens of Rome more loyal to the government and their leadership. A story about an aqueduct as a legacy and testament to greatness.

The Romans were adept engineers and mathematicians. They had the tools they needed to create a cost-benefit analysis about their public works projects. Perhaps they did. But a vision of how great Rome could be? That’s more powerful than any number.

Envisioning the change and what’s possible is the inspiring part.

Most scholars estimate that language developed about 200,000 years ago. Exactly how it started or how it evolved is a subject of great debate. We just don’t know, and we never will. But the history of writing can be traced back to the cuneiform script in Mesopotamia, in 3200 BC.

The spoken word has a massive head start over the written word. Our brains are pretty good at remembering language when it’s properly organized – like when it’s organized into stories. And stories have been proven to be more memorable and more persuasive than a collection of facts.

The Problem With Your Business Case

At some point or another you’ve been tempted to pinpoint the value you can provide to client down to dollars and cents. You should still do that, but it has to be secondary to the story you tell. The problem with making a business case your primary or only pitch is that it’s an appeal to rationality, but we know that buying decisions are emotional.

The way we typically make decisions is that we become emotionally invested in them, then rationalize the decision based on the facts at hand.

“I really want that new iPhone. Plus my phone is getting old and slow, and my time is valuable, so I should upgrade.”

Emotional first, then rational.

The other problem with the business case is that it’s not a story. It’s a collection of assumptions presented as facts that can be easily picked apart. Numbers on a spreadsheet won’t help anyone imagine how different their life would be.

The story the numbers tell is more important than the numbers themselves. If you’re in the cost-savings business, perhaps your story is about the new hires a company can make once it cuts expenses, and how those new hires will contribute to culture, and how that new culture will be just what the company needs.

Stories have meaning, numbers don’t.

If your client can save 20% of what they’re currently spending, that’s important, but so what? Will they get a promotion? Can they start a new initiative they’ve wanted for years? Will they increase bottom-line profit? What’s the meaning of saving 20%?

And finally, my last bone to pick about business cases: they’re bullshit. If you have a gold-standard, rock-solid business case, then you’ve built your assumptions on mountains of data across thousands of clients, parsed and segmented to include only the most analogous situations. But…who has that? And even if you do have it, it’s still a guess. History isn’t necessarily predictive of future results.

So tell a story first. And if you plan to make a business case, make it secondary.

“But I can’t hold your services…”

Your services aren’t tangible. No one can try, touch, or interact with them. They have to take your word for it. That’s why I advocate so strongly for making them more tangible – more like products – to make your sales process that much easier.

But no matter how much you transform your services into something that looks like a product, you can’t give your clients the experience of working you before they actually do. They have to take your word for it. And the best way to simulate that experience is to make the sales process intrinsically useful (you know, “serve don’t sell”), and tell a story about the transformation you can deliver.

Most days I eat lunch with my wife while we watch a segment or two of Shark Tank. The Sharks often compliment presenters on their sales abilities on the show. After watching hundreds of episodes of Shark Tank, I can tell you with absolute confidence that there are only two reasons a Shark will compliment someone for being a good salesperson:

  1. They were able to clearly answer every question
  2. They were adept and enthusiastic storytellers

That’s it. According to hundreds of episodes of Shark Tank, that’s what five mega-rich investors look for in a quality salesperson.

Be prepared. Tell stories.

Which leads me to a related point: the story is only effective when it’s exciting and you actually believe it. Your belief and excitement in the story is infectious. If you don’t believe it, don’t present. And perhaps start looking for a different line of work.

What’s your story about?

You can think about your sales story as a sort of future case study. What would happen with your client to make them so successful that they’d be the flagship case study you present now and forever? Tell that story.

I won’t nerd out on Joseph Campbell’s monomyth, but it’s basically a story of transformation. You don’t need to go into the level of the full story structure of Joseph Campbell.

I recommend something far simpler:

  • The pain your client is in
  • Why the pain is worse than they think, and the implications of doing nothing
  • How the future could be for your client if they addressed their pain and reached their deep, valuable goals (emotional and economic value)
  • How you can help them get there, and an example of how you’ve done it in the past (case study or testimonial)
  • The specific solution you provide and your offer

That’s it. You can do this whole thing in 10 minutes if your product is well-understood or relatively simple. Certainly you can run through the entire story in an hour no matter what you’re selling.

And once you go through the whole process, invite your prospective client to share their reaction. Your story should elicit conversation, and a discussion about how you might work together.

This process, of course, is done after you’ve established your client’s pain, goals, and the value they’re seeking. Truth is, that stuff won’t change all that much from client to client. Neither will your solution or offer. And the better prepared you are initially, the faster you’ll be able to do this moving forward.


When it comes to sales fundamentals, there aren’t a lot of changes you need to make to the way you’re doing things. The key changes aren’t so much mindset as they are behaviors. If you do the right things, your results will improve.

Just to quickly recap, the four selling fundamentals are:

  • Agendas and next steps: be clear with yourself and your prospects about the purpose of every meeting, and what needs to happen afterward to drive the sale to conclusion
  • Ask probing questions: have a carefully selected list of questions you can draw from to help your clients reach valuable insights and understand the depth of their own motivation
  • Know your value: value is contextual to each client and each situation – understand the drivers of the value you provide and focus on clients who need your services the most
  • Tell stories: focus on the transformation and impact you can make by telling stories rather than giving facts, figures, and try feature run-downs

Additional Reading

  • Get the fundamentals, tools, and setup you need to improve your remote selling
  • Build a sales strategy that matches up with your firm’s growth goals