Some Conversations Are Worth the Plane Ticket

Some Conversations Just Feel Different in Person

Every quarter, I get on a plane and fly to Texas.

It's not for a conference.

It's not for some elaborate leadership retreat.

And it's certainly not because I particularly enjoy navigating airports.

I go because roughly half of the engineers I manage are located there, and I make it a priority to have our quarterly performance and development conversations face-to-face.

Four times a year.

It's something I've intentionally incorporated into the way I lead.

Now, I recognize that we live in a world where technology has made it incredibly easy to connect with people regardless of where they happen to be.

I can open Microsoft Teams, schedule a meeting, turn on my camera, and have a perfectly productive conversation with someone hundreds of miles away.

And I do that all the time.

I'm grateful that technology gives us the flexibility to work together without having to occupy the same physical space.

But I've always felt that certain conversations carry a different weight.

Particularly the ones where we're discussing someone's performance, aspirations, opportunities, and professional future.

Those aren't just meetings to me.

They're opportunities to connect with someone on a much more meaningful level.

And while I absolutely believe those conversations can happen virtually, I also believe there's something uniquely valuable about sitting across from another human being, looking them in the eye, and giving them your undivided attention.

Because sometimes the most meaningful thing you can communicate to someone isn't what you say. It's the effort you're willing to make to say it.

These Aren't Just Performance Conversations

I've never particularly liked the idea of reducing quarterly conversations or end-of-year performance reviews to administrative exercises.

I understand why organizations have them.

There needs to be some degree of structure around evaluating performance, documenting accomplishments, identifying development opportunities, and making decisions about career progression.

Those things matter.

But I think we sometimes become so focused on completing the process that we forget about the person experiencing it.

Think about what a performance conversation represents to an employee.

They're sitting down with someone who has influence over their professional development, their opportunities, their compensation, and potentially their future within the organization.

They're hoping their efforts have been recognized.

They may be wondering whether their contributions have made the impact they intended.

They may have aspirations they're not entirely comfortable expressing.

They may be carrying frustrations they haven't figured out how to communicate.

And sometimes, they're simply looking for reassurance that the work they've been doing matters.

That's a lot to bring into a conversation.

And as a manager, I think there's a responsibility to recognize that.

What might look like another meeting on my calendar could be one of the most important conversations someone has about their career that quarter.

I try not to lose sight of that.

Because these conversations aren't just about evaluating what someone has accomplished.

They're about understanding the person who accomplished it.

Where they want to go.

What they're proud of.

What's been difficult.

What they've learned.

And what I can do to help them continue moving toward the things that matter to them.

I don't want those conversations to feel like I'm reading from a document and checking boxes.

I want them to feel like we're genuinely investing time in their future.

Why I Get on the Plane

I want to be clear about something.

I don't believe being physically present automatically makes someone a better leader.

I've worked with people who are remarkably effective at building relationships virtually.

And I've encountered people who sit in the same office as their teams every day but somehow remain completely disconnected from them.

Proximity doesn't guarantee connection.

And attendance doesn't guarantee engagement.

But I do believe being intentional about how we connect can make a difference.

When I travel to Texas, I'm creating dedicated space for conversations that matter to me.

There's something about sitting across from another person that changes the experience.

You notice things.

The moment someone smiles when talking about an accomplishment they're particularly proud of.

The slight hesitation before they respond to a question about their career aspirations.

The change in expression when you mention feedback they weren't expecting.

The way someone becomes more animated when the conversation shifts toward something they're genuinely passionate about.

Not every expression reveals some hidden truth, of course.

People communicate differently, and body language isn't a substitute for actually listening.

But those moments can invite curiosity.

They can prompt another question.

They can create opportunities to explore something that might otherwise have gone unspoken.

And perhaps most importantly, sitting together can make the conversation feel less like an evaluation being delivered and more like a discussion being shared.

That's what I want.

I'm not interested in spending an hour telling someone what I think about them.

I'm interested in spending an hour understanding how they see themselves, sharing how their contributions are being experienced by others, and working together to identify where we go next.

Performance conversations should be something we have with people, not something we do to them.

And if getting on a plane helps me create a more meaningful opportunity to do that, then I consider it time well spent.

Should Performance Reviews Really Contain No Surprises?

There's a common piece of leadership advice that gets repeated whenever performance management comes up.

Nothing in a performance review should ever be a surprise.

I've always found that statement interesting.

Because while I agree with the intention behind it, I'm not sure I agree with the absolute nature of it.

Let me explain.

If someone is consistently struggling to meet expectations, they shouldn't discover that for the first time during their end-of-year review.

If there's a significant concern about someone's behavior, performance, or ability to fulfill their responsibilities, we shouldn't wait months to bring it to their attention.

That's not fair.

And frankly, I don't believe it's particularly effective leadership.

People deserve timely feedback.

They deserve an opportunity to understand expectations, address concerns, and make meaningful improvements before those concerns become formal evaluations.

A performance review should never be the first time someone learns they're falling short of expectations.

But does that mean there should be absolutely nothing surprising about the conversation?

I don't think so.

In fact, I hope there are moments of surprise.

Positive surprises.

Unexpected perspectives.

Insights that someone hadn't previously considered.

Maybe an engineer discovers that their willingness to help a teammate made a much greater impact than they realized.

Maybe someone who doesn't view themselves as a leader learns that their peers consistently look to them for guidance.

Maybe a person who believes their greatest contribution is their technical expertise discovers that what others appreciate most is their patience, reliability, or ability to make complicated things understandable.

Those are incredibly meaningful discoveries.

And they're not always things people recognize about themselves.

I want performance conversations to create space for those moments.

Not surprises that make people question whether they've been receiving honest feedback throughout the year.

But surprises that help them recognize something new about their impact.

There shouldn't be surprises about where someone stands. But there should absolutely be opportunities to discover something about themselves they didn't know before.

To me, that's an important distinction.

Your Peers See Things I Never Will

One of the practices I've become particularly intentional about is incorporating feedback from an individual's peers into our performance conversations.

And not simply summarizing that feedback into some generic statement.

Whenever appropriate, I like to share the actual words people have used to describe someone's contributions.

Verbatim.

Because I believe there's something uniquely powerful about hearing how the people you work alongside experience you.

As a manager, I have a particular perspective.

I understand the expectations associated with someone's role.

I observe their contributions.

I evaluate outcomes.

I have conversations about career development and organizational priorities.

But I don't experience every interaction they have throughout the day.

I'm not necessarily the person sitting beside them while they work through a difficult technical problem.

I'm not always present when they stop what they're doing to help someone else understand an unfamiliar system.

I don't witness every moment when they demonstrate patience, creativity, leadership, or resilience.

Their peers often see things I don't.

And I think those perspectives deserve a place in the conversation.

Consider the difference between me telling someone:

Your peers appreciate your willingness to help others.

And sharing a colleague's actual observation:

Whenever I run into something I don't understand, they're one of the first people I feel comfortable asking. They never make me feel like my questions are stupid, and they take the time to make sure I actually understand the solution.

Both communicate something positive.

But the second carries a different kind of meaning.

It provides context.

It describes a lived experience.

It helps someone understand not just that they're appreciated, but why.

Of course, those kinds of examples should be shared responsibly. I don't believe peer feedback should become a mechanism for exposing private conversations or surprising people with anonymous accusations.

When I use someone's words, I want to respect the expectations of confidentiality, make sure feedback is appropriate to share, and avoid presenting a single person's opinion as an objective truth.

But when handled thoughtfully, I believe peer feedback can become one of the most valuable parts of a development conversation.

Because it offers a perspective that doesn't belong to the manager alone.

Sometimes the most meaningful feedback someone receives isn't about what they've accomplished. It's about the impact they didn't realize they were having on the people around them.

And I think that's worth recognizing.

Feedback Shouldn't Just Celebrate Strengths

There's another side to this.

Not all peer feedback is going to be positive.

And it shouldn't have to be.

Sometimes the people we work alongside recognize opportunities for growth that we haven't recognized ourselves.

Maybe someone is incredibly talented but has a tendency to dominate technical discussions.

Maybe an engineer consistently produces exceptional work but doesn't communicate progress as effectively as their teammates need.

Maybe someone believes they're being helpful by jumping in and solving problems, while their colleagues sometimes feel they're losing opportunities to learn independently.

These are valuable insights.

But they're also sensitive.

And that's why I believe the way feedback is delivered matters just as much as the feedback itself.

I never want peer observations to become ammunition.

I don't want someone leaving a performance conversation wondering which of their teammates said something negative about them.

And I certainly don't want to create an environment where people become hesitant to provide honest feedback because they're worried their words will be used carelessly.

Feedback needs context.

It needs thoughtful interpretation.

And it needs to focus on observable behaviors and their impact rather than personal judgments.

Most importantly, it should lead somewhere constructive.

If someone receives feedback that challenges how they perceive themselves, my job isn't simply to hand them that information and move on.

My job is to help them understand it.

To explore whether it reflects a recurring pattern or an isolated experience.

To consider what they might do differently.

And to recognize that another person's perspective is valuable without automatically treating it as an unquestionable fact.

Feedback isn't a verdict on who someone is. It's information they can use to become more intentional about who they want to be.

That's how I want it to be experienced.

The Conversation Is More Important Than the Rating

I understand that performance management exists within larger organizational systems.

There are expectations.

Competencies.

Ratings.

Promotion criteria.

Compensation considerations.

And sometimes very specific processes that need to be followed.

Those things aren't inherently bad.

Structure can create clarity and consistency.

But I've always believed there's a danger in allowing the structure to become more important than the conversation.

If someone leaves their quarterly review remembering nothing except the rating they received, I wonder whether we've missed an opportunity.

Because a rating can tell someone how their performance has been evaluated against a particular set of expectations.

But it doesn't necessarily tell them how to grow.

It doesn't always explain the influence they've had on the people around them.

It doesn't explore what motivates them.

And it certainly doesn't capture everything that makes them valuable as a person.

I want the engineers I lead to walk away from these conversations understanding more than where they stand.

I want them to understand why.

What are they doing exceptionally well?

Where are they creating meaningful value?

What might be holding them back?

What opportunities could help them grow?

What do they want from the next chapter of their careers?

And how can I help?

Sometimes those conversations involve difficult truths.

Sometimes they require us to acknowledge that someone's aspirations and their current capabilities aren't completely aligned.

Sometimes we have to discuss opportunities that simply aren't available yet.

Those conversations aren't always comfortable.

But I believe people deserve honesty.

And they deserve that honesty to be delivered with respect, empathy, and a genuine commitment to helping them move forward.

I don't believe in telling someone what they want to hear simply because it's easier.

But I also don't believe honesty requires us to abandon compassion.

The two should coexist.

Trust Is Built Between the Reviews

There's something else I think is worth acknowledging.

Flying to Texas every quarter doesn't mean much if the other eleven weeks of the quarter are spent being disconnected from the team.

A meaningful performance conversation isn't something you can manufacture by showing up four times a year.

It has to be supported by the relationship you've developed in between.

The regular one-on-ones.

The difficult conversations.

The moments when someone needs help.

The opportunities to celebrate accomplishments.

The willingness to listen when something isn't going well.

The consistency between what you say you value and how you actually behave.

Those are the experiences that establish whether someone trusts you.

And without that trust, even the most carefully prepared performance conversation can feel transactional.

I think of quarterly reviews as opportunities to bring together the many conversations we've already been having.

To reflect.

To identify patterns.

To recognize growth.

To examine where expectations and reality may have diverged.

And to make sure we're still moving in a direction that makes sense for the individual.

But I also want to leave room for new conversations.

New aspirations.

New concerns.

New perspectives.

Because people change.

What someone wanted six months ago may no longer be what they want today.

And I don't believe a development plan should become a rigid agreement that prevents someone from evolving.

The goal isn't to hold people accountable to the version of themselves they were at the beginning of the year. It's to help them make intentional progress toward the person they're becoming.

That's a much more meaningful conversation to me.

People Deserve to Feel That Their Growth Matters

Perhaps the biggest reason I make these trips is also the simplest.

I care.

I care about the engineers I have the privilege of managing.

I care about their careers.

I care about their aspirations.

I care about whether they feel supported, challenged, and recognized.

I care about the families and lives that exist beyond the work they do.

And I recognize that when someone trusts me to help guide their professional development, they're trusting me with something that can have a meaningful impact on their life.

That promotion someone is working toward might represent years of effort.

That opportunity to lead a project might help them discover capabilities they didn't realize they possessed.

That difficult feedback conversation might become the turning point that changes how they approach their work.

Those moments matter.

I don't want to treat them as administrative obligations.

I want to treat them as opportunities to make a meaningful investment in another human being.

And while I can't always control the outcome of every career decision, I can control how intentionally I approach the responsibility.

I can prepare.

I can listen.

I can be honest.

I can advocate.

I can challenge someone when I believe they're capable of more.

And I can make sure they understand that their development isn't something I only think about when performance review season arrives.

It's something I care about throughout the year.

Sometimes Leadership Means Showing Up

I've thought a lot about what I hope people remember about working with me.

I hope they remember that I challenged them.

That I helped them recognize their strengths.

That I created opportunities for them to grow.

That I listened when they needed someone to listen.

And that I cared about their lives beyond whatever projects we happened to be working on together.

I also hope they remember that I made an effort.

Not because I expect appreciation for getting on an airplane.

That's not the point.

And certainly not because traveling somewhere automatically makes a conversation more meaningful.

But because I want the people I work with to know that the time we spend discussing their careers is important to me.

Important enough to prepare for.

Important enough to gather perspectives beyond my own.

Important enough to have difficult conversations rather than avoid them.

And when it's possible, important enough to show up in person.

I don't believe every leader needs to travel to have meaningful performance conversations.

Different teams have different circumstances, and meaningful connection can take many forms.

But I do believe every leader should ask themselves whether the effort they put into these conversations reflects the importance they claim to place on their people.

Because if we're going to tell employees that they're our greatest asset, our most important investment, or the foundation of our success, shouldn't our behavior demonstrate that?

Shouldn't the conversations about their growth receive at least as much care as the conversations about the products we're building or the outcomes we're delivering?

I think they should.

And that's why, every quarter, I make the trip.

Not because I have to.

Because I've decided it's worth it.

At the end of the day, people may not remember every piece of feedback they received, every rating they earned, or every development goal they established.

But I hope they'll remember that when it came time to talk about their future, they were never just another meeting on my calendar.

They were worth showing up for.

And they always will be.