The Little Black Book

It’s not just what you know. It’s who you know. And AI might help you discover that you know more people than you think.

There was a time when a successful businessperson’s most valuable possession wasn’t their office, their car, or even their bank account.

It was their little black book.

Not the kind containing the names and telephone numbers of former romantic interests, although that’s probably what first comes to mind.

I’m talking about the other kind. The one containing the names of influential people. Decision-makers. Business owners. Investors. People who knew people. People who could make things happen.

If you wanted to get something done, you didn’t necessarily need to know how to do it yourself. You needed to know somebody who did.

And if you didn’t know that person, perhaps you knew somebody who knew somebody.

That was the magic of the little black book.

Today, we have CRMs, LinkedIn, enormous contact databases, and more ways to communicate than at any other time in history.

But I wonder whether we’ve lost sight of something fundamental.

Business has always been about people. And it always will be.

Now, with artificial intelligence, we have an extraordinary opportunity to rediscover the power of human connections.

Not by replacing relationships with technology, but by using technology to make those relationships stronger.

You Don’t Do Business With Companies. You Do Business With People.

I’ve worked with customer relationship management systems for years, and there’s something interesting about how they’re structured.

Most CRMs distinguish between two fundamental types of records: companies and people.

The company record contains what I call tombstone data: the company name, address, telephone number, website, industry, number of employees, and so on.

Then there are the people associated with that company.

The president. The marketing director. The purchasing manager. The receptionist. The person who actually makes the decisions.

Typically, there’s a one-to-many relationship. One company, many people.

Which is more valuable: the company database or the people database?

I would argue that it’s the people.

A company doesn’t shake your hand. A company doesn’t trust you. A company doesn’t recommend you to a friend. People do.

Yet when businesses go looking for new customers, they often approach the problem as though they’re trying to establish relationships with corporations rather than human beings.

They build lists of companies. They send unsolicited emails to generic addresses. They call reception desks and ask to speak to whoever handles purchasing or marketing.

And then they wonder why nobody returns their calls.

The problem isn’t necessarily their product or service. They may simply be knocking on the wrong door. Or, more precisely, they don’t know whose door they should be knocking on.

Everybody Knows Somebody

Think about the people you know.

Your friends. Your neighbours. Your customers. Your former colleagues. Your suppliers. People you went to school with. People you’ve met at conferences, charity events, or business mixers.

Now think about all the people they know, and all the people those people know. It becomes an enormous network remarkably quickly.

This is the idea behind the familiar concept of six degrees of separation: the notion that we’re connected to other people through surprisingly short chains of acquaintances.

Stephen Covey wrote about circles of influence. Dale Carnegie taught generations of readers how to win friends and influence people.

And we’ve all heard the old expression:

It’s not what you know. It’s who you know.

There’s a reason these ideas have endured. Relationships create opportunities.

Every person is a walking, talking database.

Your neighbour might know an executive at a major corporation. Your accountant might have a client looking for exactly the service you provide. A former customer might have moved into a senior management position at another company.

You might know someone who knows precisely the person you’ve been trying to reach.

You just don’t know it yet. And perhaps neither do they.

We all carry enormous amounts of information about other people in our memories: their occupations, families, interests, experiences, and connections.

Some of that information is documented. Much of it isn’t.

That’s why, even in an age of search engines and artificial intelligence, there is still tremendous value in hearing somebody say:

“You should talk to Joe. Joe knows everybody.”

Joe might know something that isn’t published anywhere on the internet. More importantly, Joe might be willing to introduce you. And that introduction could change everything.

It Started Across the Street

Let me tell you a story from my own experience.

A few years ago, I was outside doing some yard work when I started chatting with a neighbour across the street.

Nothing unusual. Just two guys talking.

Eventually, we got around to talking about what we did for a living.

I discovered that my neighbour was an accomplished HVAC engineer.

He learned that I worked in marketing and technology.

Over time, we got to know each other better. There was no business agenda. No networking strategy. No sales pitch. Just a friendship developing naturally.

Eventually, he mentioned that he was starting a small business and wondered whether I could help with the branding and website.

I said sure.

It wasn’t a particularly large project, but it was an opportunity to work together, and it strengthened our professional relationship.

Then, sometime later, he invited me to lunch.

He wanted to discuss another business opportunity involving a company he was connected with. I did some research, looked at the company’s marketing materials, and put together an unsolicited marketing audit outlining some opportunities for improvement.

My neighbour shared the audit with the people involved. That opened the door.

Today, I’m actively involved in helping the company develop its brand, strengthen its marketing, and build a new website. What began as a casual conversation has developed into a substantial professional relationship with exciting possibilities for the future.

It all began with two guys doing yard work across the street.

No cold calling. No elaborate sales funnel. No expensive advertising campaign. Just two people getting to know each other.

Of course, artificial intelligence has become an important part of the work I’m doing for the company. I’ve used it extensively for research, analysis, planning, and website development.

But AI didn’t create that original relationship. A conversation did.

I work with the trades more than any other sector, and most of that work came through relationships like this one.

And that’s a distinction worth remembering.

The World’s Most Sophisticated Networking Tool?

Now imagine taking everything we’ve just discussed and introducing artificial intelligence into the picture.

Not as a replacement for the human relationship, but as a tool for understanding and nurturing it.

Let’s say you’ve been in business for 20 years.

You have thousands of contacts scattered across your CRM, accounting software, email accounts, calendars, spreadsheets, LinkedIn connections, and various other systems.

How many of those relationships have you forgotten?

How many potentially valuable connections are buried in that information?

And how many opportunities might exist between people in your network that you’ve never recognized?

This is where AI becomes particularly interesting.

In my previous article, I talked about business data being locked in a prison, inaccessible to the very people who could benefit from it.

I talked about unlocking that data and making it available to AI so that business owners could ask questions and discover insights that would otherwise remain hidden.

Now let’s apply that same thinking to your people database.

Imagine asking your AI assistant:

• “Who do I know who might be able to introduce me to someone in the commercial property management industry?”
• “Which of my former customers now work for companies that might need our services?”
• “Who haven’t I spoken to in the past six months that I should reconnect with?”
• “I’m going to a trade show in January. Help me identify people in my network who might be attending, and suggest some worthwhile meetings.”

Provided your AI has access to the appropriate information, it can help answer these questions. It can examine relationships across multiple data sources, identify possible connections, help you prepare for conversations, and suggest where further research might be useful.

Of course, AI can’t magically know every friendship, family relationship, or private association between people. Those connections need to be documented, discovered through legitimate research, or confirmed through conversation. Use only information people have shared with you or made public, and respect privacy rules.

But when the information is available, AI can connect dots that would be extraordinarily difficult for a human being to identify manually.

And that makes your little black book considerably more powerful.

From Cold Calls to Warm Introductions

Let’s return to the problem of getting your foot in the door.

Suppose you’ve identified a company you’d love to do business with.

You know they could benefit from your services, but you don’t know anybody there.

The traditional approach might be to call the company, send an email, or try to connect with someone on LinkedIn.

Maybe you get through. Probably you don’t.

You ask your AI assistant to help identify the relevant decision-makers and look for legitimate connections through your existing network.

It discovers that someone you worked with five years ago is now associated with the company. Or perhaps one of your current customers knows the person you’re trying to reach.

Suddenly, the conversation changes.

Instead of being a complete stranger, you might be introduced by someone the prospect already knows and trusts.

That’s a tremendous advantage. But there’s an important qualification: a connection isn’t permission to exploit somebody’s relationship.

You still need to approach people respectfully, ask whether they’re comfortable making an introduction, and give them a genuine reason to do so.

A warm introduction should be warm because the relationship is real, not because AI has manufactured the appearance of familiarity. The objective isn’t to manipulate people. It’s to discover genuine opportunities for people to help one another.

Whatever Happened to Just Dropping By?

When I was younger, people used to drop by each other’s homes unannounced. Friends would knock on the door just to see if you were around. You might call someone’s house and end up talking to their mother, father, or brother before getting the person you wanted. There was something wonderfully spontaneous about those interactions.

Today, we live in a world of scheduled meetings, calendar invitations, text messages, and carefully managed availability. Even making an unexpected telephone call can sometimes feel intrusive. We can communicate with almost anybody, almost anywhere, almost instantly. And yet, in some ways, we’ve made spontaneous human connection more difficult.

I’m not suggesting that everything was better in the past. I’ve spent much of my career working with technology. But I do believe we need to be careful that our digital conveniences don’t become barriers between us and other people.

What if AI could help reverse some of that isolation?

What if, instead of encouraging us to spend even more time interacting with machines, it helped us spend more meaningful time interacting with people?

What if it reminded us to pick up the telephone, reconnect with an old friend, arrange lunch with a former colleague, or introduce two people who might benefit from knowing each other?

That strikes me as a particularly worthwhile use of artificial intelligence.

Why Do We Still Go to Trade Shows?

I’m planning to attend CES in Las Vegas this January.

It’s one of the world’s major technology exhibitions. And yes, I’m going to see the technology. But I’m also going to meet people.

Why do companies still spend substantial amounts of money building exhibition booths, sending employees across the country, booking hotels, and entertaining prospective customers? We can demonstrate products online, conduct video conferences, and communicate instantaneously. Yet people still travel enormous distances to stand face-to-face with other people.

Because there is something about personal interaction that technology hasn’t replicated: the spontaneous conversation, the unexpected introduction, the casual exchange over coffee, the opportunity to discover a common interest that has absolutely nothing to do with the business at hand. These encounters create the conditions in which relationships begin, and relationships are often where opportunities originate.

AI can help us prepare for these events: research exhibitors, identify relevant contacts, organize schedules, and suggest conversations worth having.

But once we arrive, it’s up to us to shake hands and start talking.

The technology gets us ready. The people make it worthwhile.

Your Little Black Book Needs Attention

Here’s something else I’ve noticed over the years.

Business owners get busy. Very busy. They’re dealing with customers, employees, suppliers, invoices, deadlines, and a thousand other responsibilities.

And somewhere in the middle of all that activity, they forget to maintain the relationships that helped them build their businesses in the first place.

They forget to call an old customer, congratulate someone on a promotion, remember a birthday, or follow up after a promising conversation. Not because they don’t care, but because life gets in the way.

Now imagine having an AI assistant that helps you maintain those connections.

It could remind you that a valuable customer hasn’t heard from you in months.

It could suggest reaching out to someone you met at a conference.

It could help you prepare for a meeting by summarizing your previous conversations and shared interests, remind you about commitments you’ve made, and help you recognize when two people in your network might benefit from an introduction.

Not every contact needs to become a sales opportunity.

Sometimes the right thing to do is simply to say hello. Sometimes it’s to offer help without expecting anything in return. Sometimes it’s to remember that someone matters.

A good little black book isn’t merely a list of influential names.

It’s a record of relationships worth maintaining.

Build Your Business Around People

I’ve become increasingly convinced that businesses should be building their operations around AI-enabled access to their information.

Not simply adding an AI chatbot here or an automated email tool there, but creating an integrated business environment in which AI can work with the information that drives the enterprise.

Customer records. Financial information. Projects. Communications. Marketing data. Operational processes.

And, perhaps most importantly, relationships.

Your CRM shouldn’t be an isolated database that somebody updates occasionally.

It should be part of a living information system that helps you understand your business and the people who make it possible.

Of course, that requires thoughtful organization, appropriate permissions, accurate records, and respect for people’s privacy.

But the potential is enormous.

Imagine having the institutional memory of your business available whenever you need it.

Not just remembering what happened, but understanding how people, events, conversations, and opportunities relate to one another.

That’s much more valuable than a static contact list. It’s a modern little black book.

And unlike the little black books of the past, it can help you recognize connections you didn’t even know existed.

People Who Need People

There’s a wonderful song called People, made famous by Barbra Streisand.

One of its central ideas has always resonated with me: the importance of being someone who needs other people. I think there’s a profound business lesson in that.

We sometimes celebrate the self-made entrepreneur as though success were something achieved entirely through individual effort.

But when I look back over my own career, I see something different.

I see people. People who trusted me. People who introduced me to someone else. People who gave me an opportunity. People who believed I could help them. And people who became friends along the way.

Every significant business opportunity I’ve had can be traced, in one way or another, to a human relationship.

Those relationships helped me build my business, earn a living, and put food on the table, and I suspect the same is true for many entrepreneurs.

So here’s my advice.

Don’t become so immersed in technology that you forget the people around you. Don’t allow your contacts to become forgotten records buried in a database. And don’t assume that finding new business always requires finding complete strangers.

Sometimes the opportunity you’re looking for is already sitting somewhere in your network.

Maybe it’s a former customer, an old friend, or someone you met at a conference. Or maybe it’s the fellow across the street doing his yard work.

Use AI to help you find those connections.

Use it to organize your information, research opportunities, remember important relationships, and prepare for meaningful conversations.

But don’t expect AI to do the most important part for you.

That part is still wonderfully, unmistakably human.

Because the real value of your little black book isn’t the names inside it.

It’s the relationships behind those names.

And the next great opportunity in your life might begin with something as simple as saying hello.