[2026/11/02-Event Report] Even if AI can select projects, can it select your “next career”? — Dialogue between people protected by agents

Introduction

A live talk held every Monday at 10:00 PM in the LINE OpenChat “Freelance Engineer” group.
This time, we welcomed a guest who has experienced the field as an engineer, has been involved in introducing freelance projects, and is currently working on improving information systems within the agency company “Teraseek”.

The topics ranged from the work of agents, AI matching, and engineer development, to community building. We bring you a digest of this wide-ranging conversation.
Project requirements can be matched by AI.
But, can project descriptions alone convey what you “want to do next”?
This was the question that made me think the most this time.

From engineer to sales, and then to information systems. My career path was not a straight line

The guest worked as a freelancer after gaining experience in SIer, Azure technical support, and insurance company development sites. Later, they shifted to sales, connecting engineers with companies, and are now involved in organizing internal information and systems.
There could have been a path to continue pursuing technology as an engineer. Yet, they moved on to a different role. Moreover, their development experience supported their conversations in sales, and the field issues identified in sales led to improvements in internal systems.
“Is the title I hold now going to be the entirety of my work from here on out?”
It was a story that made me want to ask that same question of my own career path.

I tried AI matching. But the quality of introductions did not improve

What left a particular impression this time was the guest’s experience of trying AI-based project matching at their workplace.
Matching skill sheets with project descriptions is not difficult in itself. However, they said that the system they tested did not provide enough of a sense of satisfaction, and it did not lead to actual project participation.

This is not a general statement that “AI matching is useless,” but rather a story about a trial conducted within that specific organization. The guest themselves did not deny the possibility that it could work depending on the maturity of the system.

Even so, there is a difference that cannot be overlooked. Even if the conditions match by 90%,

• when you have an interview, you realize “this is different from the work I imagined”

• even if it matches your current skills, it is different from the career you want to aim for next

Matching conditions and being satisfied are not the same thing.
That discrepancy cannot be seen through numerical match rates alone.

Who listens to the “beyond” that isn’t written in the project description?

According to the guest’s explanation, the sales representatives at their company look at both the company side and the engineer side. They can sense things not just from the company’s recruitment requirements, but also from the nuances of conversations with the person in charge and their history of working together.

On the other hand, engineers also have hopes and hesitations that cannot be fully written on a skill sheet. Someone who knows both sides thinks about “what this person wants to experience next” and “what kind of growth might lie beyond this project” when making an introduction.
It is not just a matching of conditions, but a proposal that includes their career.
When you are looking for your next project, you probably communicate your desired rate and remote work conditions. But,
have you been able to talk to anyone about what you want to become beyond that?

The reason people gather through referrals lies in the accumulation of relationships rather than advertising

The guest said that instead of relying heavily on advertising, they have expanded their connections with engineers based on referrals and human relationships. They also hold regular social gatherings and networking events, where conversations that go beyond just work continue.

Meeting people does not in itself guarantee project acquisition.
However, there are people who know not just the facts written on a resume, but also the person’s way of thinking and future hopes. That relationship might change the amount of information available when choosing the next job.

Is an agent just someone who brings projects? Or are they a partner with whom you can think together about what kind of work you want to choose? Depending on how you build the relationship, the view you see may change.

AI helps with internal work. But what will happen to the field of development and training?

Meanwhile, the guest also mentioned using AI to organize internal information, develop business tools, conduct screen testing, and build systems for event management. While prioritizing human dialogue in matching, they actively use AI for routine tasks and system building. This distinction in how they are used is quite interesting.

In the second half, the discussion turned to new employee training in the AI era.
While experienced professionals and AI can speed up work, what will happen to the opportunities for beginners to grow through hands-on trial and error?
Various opinions were shared by participants, including the difficulty for companies to bear the costs of training.
This is not a settled issue for the industry as a whole. However, increased efficiency through AI is not the same as the growth of the next generation. There is still room for us, the users of this technology, to think about this.

“Connecting” is not the goal, but a means to increase future options

Toward the end, the conversation expanded to include offline meetups, YouTube content planning, and sharing project information in open chats. While some plans are still in the consideration stage, the common direction was to increase opportunities to meet and foster relationships where people can consult with one another.
Instead of looking for people only when you don’t have a project, express your expertise and interests on a regular basis. Get to know what others are good at, too. Such small points of contact might one day lead to new work or learning opportunities.

Things to ask yourself before choosing your next project

The projects you can apply for with your current experience are not necessarily the same as the projects you want to build your life around. You cannot control market trends or the hiring decisions of others. However, you can choose what to learn next, who to talk to, and what aspirations to put into words.
What do you want to increase in your next project?

Before looking for a project, put your next career into words.
Before updating your skill sheet, try putting that answer into words once.
Furthermore, try talking to someone you trust. This LiveTalk became a night to think about taking that step.

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