The chess master's guide to sales excellence

Your sales team spends more time wrestling with tools than it does selling.

How do I know this? Forbes recently reported that sellers now spend a staggering 62.8% of their time in sales tech, rather than selling.

This stat completely changed how I think about sales productivity.

Here’s what to do about it…

What chess can teach you about better sales process

Here's something unexpected: chess and sales have more in common than you might think. Both require strategic thinking toward long-term goals while making the right tactical decisions in the moment. In chess, you're working toward a checkmate. In sales, you're closing deals and hitting quotas.

But here's where it gets interesting.

When researchers studied the difference between chess grandmasters and amateurs, they discovered something counterintuitive: grandmasters actually think less than amateurs. But – and this is crucial – their thinking is ruthlessly focused on winning.

Take my seven-year-old, Robbie (proud owner of a silver medal from the St. Albans local chess league). When he plays, his mind races: "Should I castle? Who has more pieces? Did I make a mistake? What's for dinner?" Meanwhile, Magnus Carlsen, the five-time world chess champion, operates differently. Most of his moves are automated by his subconscious, freeing his mind to focus solely on strategy and victory.

The Bobby Fischer approach to winning

Remember the legendary 1972 match between Bobby Fischer and Boris Spassky? Fischer didn't just play chess on the board – he played it everywhere. He complained about dates, venues, and flight times. He showed up late, disheveled, and created chaos with complaints about everything from his water to imaginary surveillance.

Fischer lost the first three games terribly. But here's the genius: it was all calculated. Boris was so rattled by Fischer's behavior that when Bobby finally focused in the second session, he demolished his opponent. Fischer had won the match before moving a single piece with intent.

The lesson? When you focus ruthlessly on winning, when every action serves your strategic goal, you achieve extraordinary results.

From chess to sales: The time crisis

So what does this mean for sales? Ask yourself: do we want our sellers thinking more or thinking less? The answer might surprise you. We want them thinking less about administrative tasks and more about winning deals.

Currently, sellers split their attention between:

• Updating the CRM
• Finding and tweaking pitch decks
• Hunting for product details
• Logging calls
• Building deal rooms
• Calculating commissions

How much time remains for actually selling? Not nearly enough.

The centralization fallacy

Here's where most companies go wrong.

We've spent the last decade centralizing everything. We move from local spreadsheets to cloud CRMs, from desktop folders to SharePoint, from email attachments to deal rooms. And yes, the business benefits:

• Process adherence
• Data consistency
• Better reporting
• Improved decision-making

But what about the seller? They now know where to find things (probably), and they get some reporting help. But remember that 62.8% statistic? These "solutions" have become time sinks, not time savers.

The real solution: Automation over centralization

Let me paint two pictures for you.

The centralization approach:

1. Seller receives content request from prospect
2. Goes to content library/SharePoint
3. Searches through folders
4. Checks multiple documents
5. Downloads everything
6. Opens PowerPoint
7. Customizes content
8. Worries about brand compliance
9. Finally sends to prospect

Time lost: 52 minutes per request.

The automation approach:

1. Seller provides basic information (products, region, industry)
2. System automatically selects relevant content
3. System assembles on-brand materials
4. Seller reviews and sends

Time lost: 2 minutes per request.

One of our enterprise clients discovered their sellers were spending 191 hours per year just on content management. That's £62,000 in lost productivity per seller annually. By switching to automation, they could reclaim 184 of those hours. Across 100 sellers, even with conservative estimates, that's £2.3 million in additional revenue potential.

The AI revolution: Structured vs. unstructured data

Sales is messy. Customer pain points, competitive landscapes, and buying signals don't fit neatly into CRM dropdowns. Traditionally, sellers have served as translators, converting complex reality into structured data that systems can understand.

But here's what's changing: modern AI can handle unstructured data (conversations, emails, documents, etc.) and extract meaning without human translation. As I like to put it: AI lets computers think like humans so humans don't have to think like computers.

This isn't just about data entry. AI can:

• Listen to calls and update CRMs automatically
• Identify patterns in successful deals
• Surface risks and opportunities
• Generate personalized content
• Draft contextual emails

The agentic sales future

Imagine a single AI agent that knows everything about your business – products, CRM data, customer interactions, market intelligence. As a seller, you could ask:

• "Who should I focus on this week?"
• "What should I discuss with this prospect?"
• "What did this contact last purchase?"

But it goes further. That same agent could:

• Draft your outreach emails
• Create customized pitch decks
• Update your CRM
• Schedule follow-ups
• Analyze engagement data
• Learn from what works

Each action feeds back into the system, making it smarter. Email opens, content engagement, and meeting outcomes all inform future recommendations. It's a self-reinforcing ecosystem that handles the chess piece movements while sellers focus on winning the game.

Why salespeople still matter

Someone asked me recently: "With all this AI, why do we need salespeople at all?"

Great question. My answer: as long as humans are buying, humans will be selling. People want to buy from people, especially for complex, high-stakes decisions. Trust, relationships, and human judgment still matter enormously.

Will this change when AI starts handling purchasing decisions? Possibly. But buying is inherently more complex than selling – it requires understanding multiple stakeholders, existing systems, and broader business context. That complexity will take longer to automate.

The path forward

The future of sales productivity isn't about working harder, it's about working smarter. We need to:

1. Stop centralizing and start automating. Moving problems to the cloud isn't solving them.
2. Embrace AI as a bridge. Let it handle the translation between messy reality and structured systems.
3. Focus on time as money. Every minute spent on non-selling activities is revenue lost.
4. Build agentic systems. Create AI agents that don't just store information but take intelligent action.

The goal isn't to replace salespeople but to free them. When sellers can focus entirely on strategy, relationships, and winning – like chess grandmasters who've automated the basics – that's when extraordinary results happen.

Remember Bobby Fischer. He won by focusing everything on victory. Your sales team can too, but only if you give them back their time. In the future, the most successful sales organizations won't be those with the most tools. They’ll be those who've learned to make their tools invisible.

As Marshall McLuhan said, "First we shape our tools, then our tools shape us." It's time to reshape our sales tools to create the sellers we need: strategic thinkers focused on winning, not administrators drowning in busywork.

The chess clock is ticking. How will you help your sellers win the game?