When I began my career more than two decades ago, the world looked very different. We did not have smartphones, social media, or instant access to information the way we do now. In many homes, there was not even a computer with dial-up internet. Fax machines were still heavily used, and while some companies had started using email, it certainly was not sitting in anyone’s hand all day long.
Selling and marketing looked different too. People met in person. They attended events, played a round of golf, grabbed lunch, and built relationships in a much more traditional way. There was more time spent getting to know people, understanding what mattered to them, and building real rapport before expecting a result.
Some of those traditional ways of connecting still exist, but we are now living in a time where companies want speed, impact, the latest tools, and the quickest possible way to the finish line.
There may still be some budget set aside for in-person activities or relationship building, but with rising costs and constant pressure to show efficiency, many companies are looking for faster wins. From a time-to-revenue standpoint, they want the shortcut.
And that is where things can start to go wrong.
Back then, relationships were built differently, and the way people researched a potential buyer or client was different too. Today, with technology and instant access to information, that heavy lifting can look completely different. Research is easier. Access is faster. Tools are smarter. But the outreach itself has also changed, and not always for the better.
Take account-based marketing, for example. Another acronym in the marketing world, usually shortened to ABM. It sounds like a great strategy in a boardroom, especially when growth has slowed and the pressure is on. It sounds focused. Strategic. Targeted. It gives leadership something hopeful to point to. A new play. A new path. A way to reach revenue goals in a competitive market.
And yes, it can be.
But also no.
ABM can absolutely be an effective way to connect with companies that are a strong fit for your product or service. The problem is that many companies approach it with a quantity-over-quality mindset, which is exactly what ABM is not supposed to be.
I have seen it happen time and time again. A company gets excited about a new automation tool. They upload a list of contacts from a target account. Someone pulls together just enough information to make it seem targeted, then uses AI to generate outreach at scale. On paper, it looks efficient. In practice, it often lacks strategy, nuance, and any real sense of human connection.
And that is where automation and AI can backfire.
These tools are powerful, but if you do not have a clear strategy, a well-defined ideal customer profile, and most importantly a properly trained team, you are simply scaling bad behavior faster. Think about a typical salesperson. They may be excellent at starting conversations, building rapport, giving demos, closing deals, and handling the day-to-day motion of selling. But that does not automatically mean they understand the power, risks, or implications of using automation tools and AI-generated content in outreach. It also does not mean they understand what happens when that outreach starts eroding trust instead of building it.
Does your company actually have best practices in place? Does the team know what to do, what not to do, and what the goal of the outreach is in the first place? Is the goal to get the email opened? To book a demo? To spark interest? To start a real conversation? Too often, that part is not clearly defined.
The many tools we have today to communicate at scale and watch for signals are not the problem on their own. They can be useful. But they can also lead to unsubscribes, disconnection, and a complete miss on the value you are trying to communicate.
I remember reviewing a targeted email sequence that had been built by a sales rep on our team. Not to call him out or suggest he had done anything wrong intentionally, but the emails were awful. Inserting a first name does not make something personal. Mentioning that someone uses a competitor does not automatically make the message more relevant. Sending a series of unsolicited emails that offer no real value and show no real understanding of the recipient is not personalization either.
What had gone wrong was not that the rep lacked effort. It was that he had been given very basic instructions: create a targeted account list, use ChatGPT to write the emails, build the sequence in HubSpot so it runs on autopilot, and in parallel follow the prospects on LinkedIn and start liking their posts.
That is not a strategy. That is activity.
And it is definitely not a set of guardrails designed to protect connection, trust, or relationships.
The truth is that most people experience the same thing today. Endless generic emails. LinkedIn messages that all claim to be personalized. A steady stream of outreach that sounds slightly polished, slightly targeted, and completely forgettable.
This is where I think we need to look backward for a moment and ask a better question. What did we do differently when relationships actually mattered more? How did we make people feel? What was it about those older ways of doing business that created trust and better outcomes?
Because the answer is not to reject modern tools. The answer is to bring traditional values into a modern strategy.
Use AI as a research tool, not a spam machine.
Use it to build a more comprehensive picture of the company and the individual. While you may not get access to every personal detail, you would be surprised by how much you can learn when you make a real effort. What causes do they care about? What kind of content are they engaging with? What organizations are they involved in? Are they active around certain events, communities, or even sports? What are they commenting on? What are they liking? What conversations seem to matter to them?
If you read between the lines, there is often hidden gold there, but it requires effort.
That is the part many teams skip.
They want the output without the work. The personalization without the thought. The relationship without the investment.
But if you are trying to stand out, especially in a noisy market, real personalization still requires discernment. It requires timing. It requires tone. It requires understanding not just who someone is on paper, but what might actually matter to them in the moment they receive your message.
That is where AI can be useful.
Not in helping you blast more emails into the world, but in helping you do better research, identify patterns, organize insights, and prepare smarter outreach rooted in actual relevance.
A Better Way to Use AI in Outreach
If you are using AI in outreach, the goal should not be to generate more emails faster. The goal should be to understand the company and the person more deeply before you ever write the message.
AI can help you summarize company background, pull together recent announcements, identify likely business priorities, and organize research into something useful. It can help you review a prospect’s public activity, surface themes in the content they engage with, and point out details that may help you understand what matters to them. It can help you compare competitor tools, uncover likely pain points, and prepare a stronger point of view before you ever hit send.
That is a much better use of AI than asking it to write a personalized email from scratch.
A smarter workflow might look something like this.
Start with the company. Ask AI to summarize what the business does, what has changed recently, where it appears to be focusing, and what may be relevant based on the role you are targeting.
Then move to the individual. Review their LinkedIn activity, public posts, interviews, company bio, or anything else that is publicly available and relevant. What are they paying attention to? What are they speaking about? What language do they use? Are there clues about priorities, frustrations, or current initiatives?
Then ask AI to help organize the information into a short brief. Not a fake personalized email. A brief. Something that helps you think more clearly before you reach out.
From there, use AI to pressure-test your angle. Ask whether your message feels generic, overly familiar, weak in relevance, or too self-serving. Ask what would make it more useful. Ask whether the timing even makes sense.
That is where AI starts becoming valuable.
Not when it writes the email for you. When it helps you earn the right to send one in the first place.
Here are a few examples of how to use it better.
Prompt 1
Based on the information below, create a concise account brief on this company. Include likely priorities, possible pain points, recent signals of change, and relevant talking points for outreach.
Prompt 2
Review this person’s public LinkedIn activity, company role, and recent content themes. What topics seem to matter most to them, and what would be the most natural angle for outreach?
Prompt 3
Using the notes below, identify what would make outreach to this account feel genuinely relevant rather than generic. Focus on timing, likely business context, and useful points of connection.
Prompt 4
Draft three possible outreach angles based on this account research. Do not write the final email. Focus on why each angle might matter to the recipient.
Prompt 5
Review this draft outreach email and tell me where it feels generic, overly automated, presumptuous, or weak in relevance.
That last step matters more than people think. AI should be helping you refine judgment, not bypass it.
Because the real opportunity is not to sound personalized at scale. It is to use modern tools in a way that still respects the human on the other side of the screen.
In the end, the goal is not to sound personal.
It is to be personal and those are not the same thing.
Want more practical shortcuts like this?
Explore my curated library of AI tools, prompts, and workflows at resources.taneilcurrie.com