Why Sales Feels Harder Than It Should - and What to Do About It

We gathered a group of senior leaders to talk honestly about what is changing in sales. No slides. No jargon. Just a real conversation about trust, technology, and the gap between activity and outcome. Here is what we heard.

There is a particular frustration that tends to sit just below the surface in most growing organisations right now. The team is working hard. The pipeline has activity in it. The CRM is being updated. Emails are going out. Messages are being sent. And yet, at the end of each quarter, the numbers feel harder to explain than they should.

It is not a lack of effort. It is rarely a lack of ambition. And it is almost never a technology problem, despite what most of the industry would have you believe.

We recently hosted a conversation with business leaders from across professional services, technology, media, and finance. The session was designed as a debate rather than a presentation. Bart Kowalczyk, CEO of AutomateNow, and Russell Dalgleish, our Non-Executive Director, led the discussion alongside a group of senior practitioners who had all experienced the same underlying tension: the feeling that sales, as it is currently practised in many organisations, has quietly stopped working the way it once did.

What follows is an honest account of what came up.

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The Megaphone Problem: When More Noise Creates Less Signal

Start with what has actually changed. Over the past few years, the tools available to sales teams have become extraordinarily powerful. AI can now draft outreach sequences in seconds. Platforms like Apollo, LinkedIn Sales Navigator, and dozens of others give anyone with a browser access to thousands of potential prospects, complete with job titles, company details, and recent activity.

On paper, this should make sales easier. In practice, it has made it considerably harder.

The reason is straightforward. When every team has access to the same tools, and those tools are all producing variations of the same message, buyers do not experience a surge of relevant communication. They experience noise. And they have become very good at filtering it.

Inboxes that once rewarded a well-crafted cold email now delete them by default. LinkedIn messages that once stood out now blend into a wall of AI-assisted outreach that all reads, somehow, exactly the same way. Buyers have developed what one participant in our conversation called a psychological spam filter. They can feel when something has been automated, even when it has been personalised with their first name.

Bart described it plainly during the session, and it is worth pausing on because the observation captures something important about where things stand.

"AI basically gave us a megaphone. Lots of megaphone, lots of noise. Everyone is shouting. But buyers just wanted a friendly phone call. People still love to buy. They hate to be sold to."

Bart Kowalczyk, CEO, AutomateNow, Linkedin

The image of a megaphone is a useful one. A megaphone amplifies whatever you put into it. If the message is clear, specific, and genuinely relevant, amplification helps. If the message is generic, rushed, or poorly aimed, amplification simply makes the problem louder and more visible.

What the best organisations are learning is that the answer to a noisy market is not a better megaphone. It is a clearer message, delivered to a more carefully chosen audience, with more patience than most sales cultures are comfortable with.

Trust Is Not a Soft Concept. It Is the Actual Reason Deals Close.

At some point in almost every serious B2B purchase, functionality stops being the deciding factor. This is especially true in markets where the shortlist of capable suppliers has narrowed down to two or three credible options. All of them can do the job. All of them have references. All of them have a reasonable answer to every question in the brief.

What breaks the tie is trust.

Not the word trust, used loosely in a pitch. The actual feeling that the people across the table will tell you the truth, stand by the project when things get complicated, and behave consistently whether they are presenting to the board or troubleshooting a problem on a Wednesday afternoon.

Russell spoke about this from both sides of the table. Before joining AutomateNow as Non-Executive Director, he ran organisations of significant scale and was a buyer of exactly the kinds of services many of us on the call were selling. His perspective on what actually closes a deal is worth hearing directly.

"In the UK, we typically do not buy on functionality. We buy on trust. When I was buying software for a 200 million pound business, the final three options all ticked the boxes. The decision came down to which supplier we believed would stand by us to make the process work — particularly through implementation."

Russell Dalgleish, Non-Executive Director, AutomateNow

What Russell describes is not unusual. It is, in fact, the norm in high-value B2B sales. And it points to a fundamental misalignment in how many sales teams spend their time and energy.

Most sales methodologies focus on the early stages of the funnel. They are built around generating leads, getting into conversations, and moving prospects towards a decision as efficiently as possible. What they tend to neglect is the slower, less measurable work of building the kind of trust that actually wins the deal at the end.

Trust is built through consistency. It is built through showing up with the same message, the same tone, and the same honesty over time. It is built through asking better questions than the competition. It is built through the willingness to say when something is not a fit, rather than pursuing every conversation as though it must become a client.

It is also built, increasingly, through digital presence. Russell observed during the conversation that LinkedIn in particular has become a trust surface in a way that many people have not fully internalised. Every post you put out, every comment you make, every story you share contributes to a cumulative picture of who you are and how you think. Buyers who are evaluating you are not just looking at your website or your case studies. They are reading your feed. They are forming a view.

The risk, as Russell pointed out, is inconsistency. A technology founder whose LinkedIn is full of personal political commentary creates a different signal to one whose presence is focused, thoughtful, and professionally coherent. Whether that is fair is beside the point. It is what happens.

The Data Paradox: Having Everything and Knowing Nothing

One of the more interesting tensions that emerged during the conversation was about data. Specifically, the gap between having access to enormous amounts of it and actually being able to use it well.

Russell framed it memorably. He described starting his sales career by getting the bus to the library, writing down the names of companies he wanted to call, travelling back to the office, and spending an afternoon working through a phone list. The gatekeeper on reception was the first obstacle. Getting through to the right decision-maker felt like a genuine achievement.

Today, he has tens of thousands of connections across LinkedIn, email, and CRM systems. The data problem is the opposite of what it once was. Instead of too little, there is too much. And the tendency, he argued, is to respond to that abundance by doing something counterproductive: trying to contact as many people as possible, as quickly as possible, with the tools that make that easy.

The result is the megaphone problem described above. But it is worth naming the data paradox more precisely. When you have access to a thousand potential prospects, there is a temptation to treat all of them as equally worth pursuing. Segmentation feels like slowing down. Prioritisation feels like leaving opportunity on the table.

In practice, the opposite is true. The organisations seeing the best results from their sales activity are not the ones with the longest outreach lists. They are the ones who have done the harder work of getting genuinely specific about who they are for, what problem they solve for that person, and why they are better positioned to solve it than anyone else.

Angus Hay, who leads AI-driven growth strategy work with a range of clients, put it clearly: when you drill down and get specific about who will actually get the most value from what you do, the messaging starts to resonate in a completely different way. Not louder. Sharper.

The practical implication is uncomfortable for most sales teams. It means being selective. It means accepting that a shorter, better-targeted list outperforms a longer, poorly-targeted one. It means investing time in understanding the buyer rather than simply reaching more of them.

Marketing and Sales: The Merger That Most Organisations Have Not Yet Made

For a long time, sales and marketing operated as distinct functions with distinct objectives. Marketing generated awareness and leads. Sales converted them. The two teams met occasionally, disagreed about lead quality, and mostly worked in parallel rather than in concert.

That model is breaking down. And the organisations that are adapting fastest are the ones where the line between the two has become genuinely blurred.

What is driving this? Several things. Buyers now do most of their research before they ever speak to a salesperson. The LLM-assisted buying journey means that by the time a prospect reaches out, they may already have a strong view of which providers are worth talking to and roughly what they should expect to pay. The educational work that sales teams once did in early conversations is increasingly happening before the first call ever gets booked.

This changes the job of both functions. Marketing needs to produce content that earns trust with buyers who are already making decisions, not just building awareness. Sales needs to maintain a visible, credible presence that supports the buying process rather than interrupting it.

Bart observed that the most effective salespeople today are investing in their own personal brand in a way that would have looked more like marketing a few years ago. They are producing content. They are sharing perspectives. They are showing up consistently in the channels where their buyers are spending time. The distinction between building pipeline and building reputation has collapsed.

Rebecca Wilson, a participant in the session, shared how she uses AI note-taking tools after every sales call to identify the most compelling stories from her own conversations, which she then turns into content. The AI is not writing for her. It is helping her notice things she said that resonated, and packaging them into material that serves the next buyer further up the funnel.

This is a genuinely useful reframe. The question is not how to use AI to do more outreach. The question is how to use AI to help you do your best thinking better, and then make that thinking visible to the right people.

What the Best Sales Conversations Actually Look Like

There is a version of selling that feels like a performance. The rep has a deck. The prospect has a set of questions. Both sides know the choreography. By the end of the call, neither party is particularly clearer about anything, but a follow-up has been scheduled and the CRM has been updated.

And then there is a version of selling that feels more like a diagnosis. The conversation starts with genuine curiosity about what the prospect is experiencing. The questions are not scripted prompts designed to qualify budget and timeline. They are honest attempts to understand what is going on, what has been tried, where things have got stuck, and what a genuinely good outcome would look like.

The difference between these two conversations is not technique. It is intent.

AutomateNow's approach to sales is built around the second version. We call it clarity first. Before we talk about what we do, we need to understand what you are dealing with. Because in our experience, most growth challenges are not caused by a lack of ambition or a missing tool. They are caused by misalignment: between teams, between processes, between what leadership believes is happening and what is actually happening on the ground.

This changes how we open a first conversation. Rather than presenting capabilities, we aim to understand what is driving growth and what is getting in the way. Rather than pitching a solution, we try to create enough clarity that both parties can make a genuine assessment of whether there is a fit.

Kevin, who leads a virtual reality company working in dementia care, shared something during the session that captured this principle well. When he describes what he does as a VR company that uses virtual reality as an empathy platform, the description is technically accurate but does not create much of a pull. When Russell described it instead as a way of seeing through the eyes of someone with dementia, the room came alive. The question was no longer what the product does. It was how on earth does that work.

That is what a good sales conversation does. It creates a pull. Not through pressure, but through a description of the problem so vivid and so accurate that the person across the table leans forward rather than back.

The Buying Process Has Changed. Most Sales Processes Have Not.

Mike Watson raised a point during the session that deserves more attention than it usually gets. He framed it as a question about effort: where, in the arc between buyer and seller, does the real work happen, and who is responsible for it?

His observation was that a lot of sales leaders and CEOs are currently trying to shift the effort to the buyer. They want the content to do the work. They want the automation to do the outreach. They want the buyer to arrive pre-educated, pre-qualified, and ready to move. The role of the salesperson, in this model, shrinks to closing.

The problem is that effort and trust are correlated. The work of genuinely understanding a buyer, crafting a message that speaks to their specific situation, and building a relationship over time before there is any urgency to close is not an inefficiency to be eliminated. It is the mechanism by which trust is created.

Russell made a related point about timing. You can want to sell someone something today. But they will want to buy it when they are ready. If you push before they are ready, you do not accelerate the deal. You damage the relationship. You become the person who was pushy, and that reputation is hard to undo.

The practical implication is that the best sales approach is not about generating the most activity. It is about being present and credible at the moment the buyer is ready to move. That requires patience. It requires consistency. And it requires a willingness to play a longer game than most quarterly targets encourage.

Jeremy Gray, who works across international markets and whose most recent clients found him rather than the other way around, put the point directly. If someone comes to you, the chances of closing are far higher than if you go to them. The work of being visible, useful, and trustworthy over time is what makes that happen. It is not passive. It is just differently active.

The Role of Community: Building Something That Outlasts Any Single Campaign

One of Bart's closing observations was about community, and it is worth investing in because it represents a meaningfully different way of thinking about how organisations generate sustained pipeline.

Most sales and marketing activity is episodic. There is a campaign. It runs. There are results. The campaign ends. There is a gap. There is another campaign. The pipeline rises and falls in waves, often in ways that are difficult to predict or control.

Community is different. Not a subscriber list. Not a newsletter that goes out monthly. A genuine community is a group of people who share a purpose, gather around a topic or a set of ideas, and whose engagement is driven by the value they get from each other as much as from the organisation that convened them.

What makes community powerful as a commercial asset is that it compounds over time. Trust is built gradually and then held. Relationships form between members that make the network stickier. People who become buyers are already part of something, which means the transition from contact to client feels natural rather than transactional.

Building something like that takes time and genuine intent. You cannot fake the purpose. You cannot shortcut the engagement. But once it exists, it becomes a sustainable source of relationships that no campaign can replicate.

A Practical Note on Using AI Well

It would be easy to read everything above and conclude that the message is simply to use less AI. That is not what anyone in the conversation argued.

The point is more precise. AI used to replace human judgement, human curiosity, and human relationship-building produces noise and damages trust. AI used to support and sharpen those things produces clarity and creates leverage.

Russell shared a habit that illustrates the distinction well. Before an important sales conversation, he asks his AI assistant to adopt the persona of the buyer he is meeting with. He then asks it to look at everything publicly available about him and identify what aspects of his background and experience that buyer would most likely find relevant or compelling.

The output is not a script. It is a set of angles and connections he might not have thought of himself. A five-year period working in banking that he had half-forgotten about. A LinkedIn post that touched on a subject directly relevant to the client's industry. It helps him prepare for a human conversation in a way that makes that conversation better.

Angus Hay made a similar point from the agency perspective. The companies he sees getting the best results with AI are not the ones using it to automate everything. They are the ones using it to empower the people doing the work, taking the time-consuming research and analysis off their plates so they can focus on the parts that require genuine human intelligence.

The analogy is simple but useful. AI is a very capable assistant. It works best when the person directing it is clear about what they are trying to achieve and capable of evaluating what comes back. It does not replace the clarity. It depends on it.

What This Means for Leaders Navigating Sales Right Now

If you are a CEO, Managing Director, or senior revenue leader reading this, some of what is described above will feel familiar. Growth that has become less predictable. Teams that are busy but not always moving in the same direction. Systems that exist but do not quite connect. Reporting that technically works but does not give you the confidence you need to make decisions.

These are not symptoms of a broken sales function. They are, more often than not, symptoms of a clarity problem. When leadership does not have a sharp, shared view of what is driving growth and what is getting in the way, everything downstream becomes harder than it needs to be.

The conversations we have with leaders at AutomateNow almost always start there. Not with a review of the CRM. Not with a technology audit. With the question of what is actually going on, in plain terms, and what would need to be true for the next twelve months to feel meaningfully different.

Sometimes that conversation reveals a process gap. Sometimes it reveals a team alignment issue. Sometimes it reveals that the right foundations are largely there but have never been clearly named or consistently applied. Wherever it leads, the starting point is always the same.

Clarity first. Growth next.

If any of what we have discussed in this piece resonates with what you are experiencing, we would be glad to have a conversation. Not a pitch. A genuine conversation about what clarity looks like in your business and whether there is something useful we can help you see.