Boost Your Leadership Skills With These 5 Top Sales Tips

Leadership is fundamentally about your ability to sell.

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It’s common to find people who like to say that they “don’t do sales”, even though in reality they have to — it’s impossible to run a business without doing sales.

Whether your job title actually has “sales” baked into it, the basic principles of leadership require the basic skills of a salesperson. This is because leadership absolutely requires you to go somewhere where no one else has gone. This can be a “no one has ever gone here before, ever”-type leadership (e.g. a café exclusively serving owners of three-legged Jack Russell terriers), or it can be a “no one has ever gone here in this organisation before”-type leadership (e.g. getting a poorly-performing team to perform better).

If you don’t think you do sales in your day job — but as mentioned if you’re in a leadership role, you already do do sales — there are some things that you can do to “sell better”, and as a result, “lead better”. Here are five of them.

1. Sales is about pain

This is the absolute golden rule about selling — all sales are about solving the customer’s pain. The reason why the metaphor works is that by focusing on the customer pain — i.e. focusing on the customer’s problem — we are much more likely to be successful in making the sale. People do not buy unless there is something in it for them, and in all cases you can reframe the “why” into something that’s causing them pain. For example, it is much easier to sell a pack of paracetamol to someone who has a headache than it is to sell it to someone who doesn’t have one. And, it is far easier to sell Nike trainers to someone who is afraid of being judged by their peer group than it is to sell them Clark’s.

The actual mechanics of sales is that we have to actually draw out what the customer’s pain is, and reflect that pain back to them. This in and of itself is the single biggest difference between a good salesperson and a bad salesperson. Imagine a prospective customer says, “we need to buy a new customer relationship management system (CRM) for the business”. A good salesperson will ask “why?”, whereas a bad salesperson will start talking about the features and benefits of the CRM system that they happen to sell.

The good salesperson is asking a question related to pain. The customer will only be in the market to buy a CRM system if they are experiencing some sort of issue that they feel will be solved through the acquisition of a new CRM system. By asking “why?” the good salesperson is eliciting a conversation about the problem underneath the motive and can therefore craft their offering to more exactly match that problem.

The bad salesperson is just hooking on wherever they think the opportunity is. By reeling off the features and benefits of their solution, they’re hoping (more like, they are just assuming) that their offering will line up with whatever problem the customer may have. That might work, or it might not, but even if it does work, customers are more likely to buy from salespeople who “get them” — i.e. those that understand their problems — than from those who do not.

What this means that it is essential that whenever you are talking to a prospect — which can either be someone you are looking to sell or, or someone that you are trying to convince should do something for you — you need to focus on what’s in it for them, i.e. focus on how if they do this thing for you (place an order, release a resource, whatever), there is a decent upside for them.

A side note on this that is worth considering is that because “pain” is so important in the sales process, it is substantially easier to sell something that is a painkiller (i.e. it makes an unmanageable pain go away) than it is to sell a vitamin (i.e. it might be beneficial to have this, but actually if you don’t have it more likely than not you won’t notice). If you are considering a new business opportunity, think long and hard about whether what you’re doing is a painkiller or a vitamin, because it’s often not worth being in the business of selling vitamins.

2. Sales is a structured, repeatable, and improvable process

One of the things that I found hardest to get my head around when I started professionalising my sales is that at its core, sales is a very structured process.

The most common process-based metaphors in sales are the “sales funnel” and the “sales pipeline”. The purpose of a “funnel” is that this a structure that is wide at the top and narrow at the bottom — the top is generally considered to be the “leads” and the bottom is considered to be the “sale”. There are then a series of steps that align with the sales process, and as the prospect moves from one step to another, they either keep progressing down, or they opt-out of the process.

For example, imagine a prospect registers their interest on the website. At this point, it is a “lead”. A salesperson contacts the prospect trying to set-up a phone call to discuss the customers “pain”. At this point, the prospect will either engage or not — i.e. a call is scheduled, or the prospect is unreachable and/or refuses the appointment. This represents progression down the funnel, or not. The next stage might be to prepare a proposal — again, the prospect either wants a proposal or not, i.e. they either progress down the funnel or not.

The reason why this is drawn as a funnel is that at each stage only a percentage of people progress down. You might have ten leads come in, but set-up only nine calls. Only four of those calls want a proposal, and of those four, only one buys. It pinches and narrows down from ten leads (100%) to one say (10% of leads convert to sales) — hence the funnel shape.

(As an engineer, this is a wonky metaphor because the underlying principle of a funnel is that 100% of the material at the top emerges from the bottom… but there we go.)

As mentioned, the other side of this the sales pipeline. This is a way of visualising and confirming the health of the sales funnel over time. Sales processes are relatively static in terms of the proportions involved in the progression through the states. The number of leads you get it will be reliably linked to the amount of marketing that you do — spend £xk on Facebook marketing and you will get “n” leads. Spend twice that, get twice the number of leads; spend nothing, get no leads. Of the leads you get in, you will set-up “p%” of follow-up calls, and whatever percentage this is, it will be relatively static. You’ll produce “q%” of proposals, and again that will be a static percentage, and so on. You can improve and optimise the percentages over time, but it is unlikely that they would change erratically over time.

The pipeline is a snapshot of how many of each prospects are in what stage, and it is an essential part of sales forecasting. For example, if you know that you convert 25% of proposals to sales, if you have zero proposals in the pipeline, you can rely on getting no sales. Or, more happily, if you 60 proposals in the pipeline, you know that are likely to close 15 sales.

The reason why this matters is that unless you manage sales as a structured process, the whole affair can become very hit and miss and unmanageable. Seeing as your business will be utterly dependent on a reliable cashflow, it’s therefore essential that the sales operation is managed in a professional, structured, and improving fashion.

3. Sales proposals should demonstrate understanding of customer pain

Coming back to the point that sales is all about pain, the best way to build a sales proposal is based on the principle of listening to and reflecting back the customer’s pain. In terms of proposals, you can either think of this section relating to formal proposals that you send to the customer, or you can think of it in terms of just “proposing” a course of action.

When you’re talking to a customer in order to tease out their pain-points, the best method to take is one rather like a therapist might take. You need to ask open questions that allow the customer to express their pain, and then reflect back what they’ve said in order to demonstrate your understanding of what that pain is, and how it’s impacting on them.

When you’re writing a proposal — or ever just summarising the customer’s pain back to them — you should try and follow this structure:

  • Problem,
  • Pain,
  • Impact,
  • Vision,
  • Solution.

Taking an example of jotting down a quick email to a customer summarising a meeting before a more formal proposal was written, you might do this:

  • Problem — state what they’ve asked for, e.g. “Thank you for meeting with me yesterday to talk about your requirements for a CRM system”.
  • Pain — state what pain they are in/what need they have, e.g. “You told me that you have a recurring problem that when a customer phones in with an issue, you can’t see a history of your interactions with the customer previously”.
  • Impact — state why the pain is a problem, the intent of this is to demonstrate understanding of the pain, e.g. “This is causing the customers a great deal of frustration because each time they speak to someone new, they’re having to go back through history explaining how they go to where they are. You think customers are not getting the best impression of the business as a result, and are not recommending you into other customers. You also are aware that internally calls are taking, you think, about three-to-four times longer, increasing customer service costs, and causing more frustration to customers because they are waiting a long time for their calls to be answered”.
  • Vision — sketch out one solution that might solve the pain, but without making it specific to your product or service, e.g. “You told me how in your old company you had a proper CRM system that was able to capture a full history of the customer. When calls were answered at your old company, the customer service person could easily get a handle on what had gone on historically and was better able to offer immediate help to the caller”.
  • Solution — close the proposal by talking how your solution can solve their pain, e.g. “We spoke about how my company is able to deliver XYZ CRM system, and that given our conversation I felt that what we were able to offer to you should be a good solution. I mentioned in the meeting that a formal proposal would take about a week to produce, and I’m happy to say that a formal proposal will be with you on Friday”.

The reason why this structure works is that, fundamentally, it’s about the customer and not about you or the product. It is a classic example of “solution selling” — i.e. it builds up confidence within the customer that you are able to take their pain away by offering a solution to their problems.

When talking to the customer face-to-face (or on the telephone) as part of the sales process, by using this method where you are notselling what you do, you are able to get the customer to reach their own conclusion about what they need. It’s then not your fault that whatever they happen to need to buy happens to be exactly what it is that you sell.

4. Salespeople may be engaged when the customer is not ready to buy

The best way to sell anything is through relationship marketing — i.e. if you have a relationship with a customer, it is much easier to sell. This is because having a relationship with someone gives you an opportunity to build up their trust in your expertise, and someone is far more likely to buy from someone perceived to be an expert than from someone who is not.

But what actually does “having a relationship” mean? If you think about buying anything large and complex, such a house or a car, the actual point at which you are buying is one point on a continuum of behaviours. The start of this process is actually an unconscious dissatisfaction with the status quo — and this is where the customer’s pain starts to set in. Like any form of pain that we’re used to feeling as individual human beings, pain starts small and gets bigger, until such point as we have to do something about it.

What this means is that you need to be ready to engage with the customer regardless of whereabouts in their buying process they happen to be. (Albeit, you need to properly manage and control associated costs.) This is why things like content marketing and email marketing work — if you keep delivering value and building up perception of expertise with the customer over time before they are ready to actually buy, when they do get to a point where they want to buy they are much more likely to buy from you.

5. Sales is about positioning

The final point about sales is that it is all about positioning. From a purist’s standpoint, positioning is more about marketing than it is about sales, but my personal philosophy is that there is really no difference between these two disciplines. You cannot have one without the other, and you can’t do either well without fully understanding the other one.

The principle of positioning is all about focus. It’s a fairly deadly mistake in marketing to be all things to all people. We can see how this works by looking at any effective, well-known marketing strategy. Rolls-Royce do not make economy cars. The Coca-Cola Company as a business does make healthier drinks than Coca-Cola, but Coca-Cola itself is not marketed — i.e. not “positioned as” — a health-food drink. Aldi and Lidl sell on price, not quality; similarly, Waitrose sells on quality, not price.

Why positioning works comes down to conversations and relationships. We know that if we sell, we need to engage in conversation, because without that conversation we cannot learn about the customer’s pain, and without understanding the pain we cannot help them visualise a solution (which happens to involve them buying what we are selling). At the marketing stage, we haven’t had the conversation yet — we need to draw people in to that conversation. Very early on in that process, we have to demonstrate to the customer that the conversation will be worth it.

This requires focus — and this focus is done with positioning. Early on in the sales process you need to decide exactly what it is that you are selling. This is your position. It can either be strategic — i.e. it’s what your business does, or it can be tactically — i.e. it can be what you need now to achieve a specific goal as part of that strategy.

One you have the position sorted, you then turn your attention to the messaging. The messaging states the position to the market. Commonly, this is done with advertising, but any pre-sales interaction with the customer should be designed to reinforce the position. For example, at a board-level Aldi might agree that they want to be a “discount supermarket that offers own-brand goods more cheaply than other supermarkets, along with selected well-known brands”, and therefore this is their position. A message around that position might be advertising that shows a basket of Tesco products at one price, and a basket of equivalent Aldi products at a lower price.

To reiterate, the point, the reason why positioning is important is that you cannot sell anything without it. You cannot be “all things to all men” — and there is a reason why the some variation phrase “jack of all trades” appears in pretty much every spoken language worldwide. You cannot sell without focus.


In this article, we looked at five principles to professionalising sales, all of which will help improve your leadership. You can take all of these to heart, and I hope you do, but if you only want to take one thing away — always make sure that you are focusing on the customer’s pain.

The Startup

Medium's largest active publication, followed by +708K people. Follow to join our community.

Matt Reynolds (@mbrit)

Written by

I’m the founder of It’s What’s Next IT, the UK’s first IT support company that happens to be a social enterprise —

The Startup

Medium's largest active publication, followed by +708K people. Follow to join our community.

Matt Reynolds (@mbrit)

Written by

I’m the founder of It’s What’s Next IT, the UK’s first IT support company that happens to be a social enterprise —

The Startup

Medium's largest active publication, followed by +708K people. Follow to join our community.

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