I’ve been spending a fair amount of time on LinkedIn lately, reconnecting with people, catching up with former coworkers, and exploring new opportunities after nearly ten years with the same company.

For the most part, it’s been a really good experience. I’ve heard from people I haven’t spoken to in years, and quite a few have gone out of their way to help. It’s been a good reminder of how valuable those relationships can be.

But I had an interaction recently that honestly left me scratching my head.

Someone reached out about a potential opportunity. We had a former employer in common, although we’d never actually worked together. They were apparently working on something interesting, needed someone with my background, and thought I might be a good fit.

Great. I’m looking at opportunities, and I’m always interested in hearing what people are working on.

So I asked a few questions.

Who are you working with? What’s the role? What kind of project are we talking about?

Apparently, those weren’t questions that could be answered without a phone call.

A Connection Isn’t a Relationship

Now, I don’t have anything against talking on the phone. Sometimes it’s a much easier way to have a conversation, particularly when you’re trying to explain something complicated.

But I don’t think asking for a little context beforehand is unreasonable.

I wasn’t looking for confidential customer information or details about something that hadn’t been announced. I was just trying to figure out what was actually being proposed.

Was this a full-time position? Consulting work? Someone putting together a team for a project?

I asked again, trying to make it easier to answer without disclosing anything sensitive.

The conversation went downhill pretty quickly.

Which was honestly surprising. Someone had reached out because they thought my experience might be valuable, but apparently asking what they wanted me to do was a bridge too far.

The more I thought about it, though, the more I realized there was something worth considering beyond that particular exchange.

We sometimes seem to assume that having a professional connection in common should establish a certain level of trust.

I’m not sure that’s how it works.

Shared History Isn’t Shared Trust

I spent nearly ten years with my previous employer, and during that time I worked with some incredibly talented people.

There are former coworkers I’d happily work with again tomorrow. I know how they approach problems, how they communicate, and how they handle things when something doesn’t go according to plan.

But I trust those people because I’ve worked with them.

We’ve solved problems together. We’ve disagreed about technical approaches. We’ve dealt with situations where the original plan didn’t work and had to figure out what came next.

That’s where those relationships came from.

Working for the same organization might give us something to talk about, but it doesn’t automatically mean we know each other.

And when you’ve worked for a large company, that’s especially true. There are probably thousands of people who could legitimately describe themselves as former coworkers whom I’ve never actually met.

That’s not a criticism of anyone. It’s just the reality of working in a large organization.

Confidentiality and Transparency Aren’t the Same Thing

The other thing that bothered me was the idea that nothing could be discussed without a phone call because the opportunity was somehow confidential.

I’ve worked with enterprise customers for years. I understand that there are things you can’t share, and sometimes there are very good reasons for that.

But I think there’s a difference between confidentiality and not providing any useful information.

You don’t have to tell me who your customer is, what their infrastructure looks like, or what they’re planning to build.

But surely there’s a way to explain whether you’re looking for an employee, an independent contractor, or someone to help build a consulting business.

Maybe there are situations where even that information is sensitive. I can appreciate that.

But if that’s the case, I also think it’s reasonable for someone to decide they don’t have enough information to continue the conversation.

Neither side has to be wrong for that to happen.

Asking Questions Isn’t an Accusation

It’s funny, because this is something I’ve spent a lot of time thinking about in software development lately.

We put a tremendous amount of effort into making sure requirements, expectations, and constraints are understood before we start building something.

At least, we should.

I’ve spent the last several years working on automation, and one thing I’ve learned is that assumptions can become expensive very quickly.

If someone asks for something and we don’t understand what they actually want, we can build something technically correct that completely misses the point.

That’s why I’ve become such a believer in documenting decisions, making expectations clear, and understanding intent before jumping into implementation.

Not because I don’t trust the people I’m working with, but because I want everyone involved to understand what we’re trying to accomplish.

Why wouldn’t we approach professional conversations the same way?

When someone asks what you’re proposing, what the expectations are, or how something is supposed to work, that doesn’t automatically mean they’re questioning your integrity.

Sometimes they’re just trying to understand.

And I’d argue that’s a pretty reasonable place to start.

An Opportunity Is a Two-Way Conversation

There’s another part of this that’s worth mentioning, particularly for people who are looking for work.

When you’re exploring opportunities, it’s easy to feel like you should be grateful whenever someone expresses interest.

And I am grateful. I’ve had people in my network go out of their way to help me recently, and I genuinely appreciate it.

But that doesn’t mean every conversation has to turn into an interview, or that every opportunity is something you have to pursue.

The person reaching out is trying to figure out whether you’re someone they’d want to work with.

You’re doing exactly the same thing.

You want to understand the role, the expectations, the people involved, and whether it’s something that makes sense for you.

I don’t think those are unreasonable things to ask.

And I don’t think asking them should somehow be interpreted as being difficult.

Where I Landed

I still don’t know what the opportunity was, and at this point I probably never will.

Maybe it was something interesting. Maybe it would have been a great fit.

But if asking a few basic questions is enough to end a conversation, I’m not sure there was much of a working relationship to begin with.

What struck me about the experience wasn’t really the missed opportunity. It was how quickly a simple request for information turned into something confrontational.

I wasn’t questioning anyone’s credibility. I was trying to understand what I was being asked to consider.

And I think that’s the larger lesson here.

Having a company, a connection, or a professional background in common might be enough to start a conversation.

But trust is something we build through those conversations, not something we should expect to already exist.

And sometimes, asking a few simple questions is exactly how that starts.