We’ve all seen millennial co-workers pouring over study prep for the GRE/GMAT/LSAT/WNNPs [relax overachievers, I made that last one up] within the first few months of starting their first job. And sure, on the surface that employee probably looks quite confident.

“She’s here two weeks and already she’s thinking about Law School.”

In fact, I’ve been amazed at how many times friends have told me that their bosses just kind of expected them to be confident without any real workplace experience or coaching from their managers. And I think that is where that perceived confidence begins to work against millennials. Confidence is something that everyone strives for at some point in their life, and for a lot of C-Suite executives it’s a defining characteristic for those who are tapped to move up the rank-and-file. It’s a check-mark on the list of being a “Good Executive,” because it has become synonymous with being a driven, hard-working professional who can get the job done.

But when an experienced manager sees a millennial studying for the GMAT on day one, how is that interpreted? In the case of the young woman mentioned above, her studying for Law School was actually viewed negatively in this specific case, because the manager thought it signaled that she was uninterested in her current job and already thinking about moving on. So, in this instance, was a millennial appearing confident actually a bad thing?

Millennial Communication Styles: How Leaders Can Communicate Across Generations

Before I get too far ahead of myself, let’s back up and dissect how many of us actually view ourselves as being confident to begin with. I’ve seen over a hundred millennials studying for grad school or working on that first big project through lunch at dozens of companies across the country. But I can’t remember ever seeing anyone who looked remarkably sure of themselves with their head in a study book, cursing themselves for not remembering how to multiply fractions. In one hilariously unfortunate case, I saw a new employee mistakenly adding hot sauce to their 2pm coffee while they were frantically trying to remember PEMDAS.

If we look at the assumed confidence stereotypes of millennials and this observed, frantic behavior simultaneously, then each millennial is floating somewhere between thinking that they invented PowerPoint and their fourteenth nervous lap around the supply room. So, for the last question from our small survey, I wanted to know how each of the participants honestly felt about starting to build their career.

So let’s go back and put this into perspective with the case of the young millennial woman studying for the LSAT in her first two weeks. We so often hear the phrase that “confidence is key,” and according to our survey results, more millennials have it (or think they have it), than don’t. Yet in this woman’s case, having the drive and self-assertive discipline to begin prepping for an arduous testing process for law school actually hurt her in her manager’s eye. Is that entirely fair? No, it isn’t. And I’m in no way arguing for anyone to set their ambitions aside. But perhaps if nothing else, this last survey question serves to underscore the divide of how managers and millennials interpret things differently. The millennial is just doing what she’s been doing through high school and college, planning ahead and trying to succeed. But the manager sees a strong indication that it’s not worth investing time in the millennial, because the latter is indicating that she will leave soon anyway.

But how do we put this whole survey together? What does our initial portrait of “the real” millennial look like? The most popular answers to each question would suggest that a millennial chooses their first job based on the industry (34%), intends to be named the CEO (36%), will stay in their first job tentatively, but will always be keeping an eye out for new opportunities (46%), and are moderately nervous about their careers (54%). Yet the second most popular choices paint a very different image. They suggest a millennial chooses their first job based on salary or work-life balance (25%), intend to be upper-level management but not the CEO (29%), don’t see any future at their current company (27%), and are confident in the direction of their career (33%).

Both of those sketches are not terribly far apart, but they suggest two significantly different employees. So it would appear that we didn’t discover a set “millennial mold.” But for the generation that is allegedly the most diverse, that shouldn’t be too surprising. If there is one set takeaway from our first survey it’s that even though we all approach our careers differently and our paths are diverse, we all start from base camp, looking up.

Millennial Communication Styles: What Millennial Communication Styles Mean for Leaders Today

The original survey behind this article captured millennials at a particular moment. Many were entering the workplace, choosing their first jobs and trying to understand what professional success would require.

That context matters. Especially when it comes to millennial communication styles.

Today, many of those same millennials are managers, executives, business owners and experienced specialists. They are no longer simply the young employees being discussed by senior leaders. They are often the leaders making hiring decisions, coaching emerging talent and trying to interpret the expectations of another generation entering the workplace. This includes millennial communication styles.

Yet the central lesson of the survey remains relevant: confidence is easy to misread.

An employee may appear self-assured while privately questioning every decision. An ambitious career plan may be interpreted as a lack of commitment. A relaxed communication style may sound disengaged to one leader and authentic to another.

Understanding millennial communication styles requires leaders to look beyond the first impression and ask what the behavior actually means.

Millennial Communication Styles: Generational Labels Cannot Explain Individual Behavior

Generational research can help leaders recognize broad changes in workplace expectations. It can provide useful context for how technology, education, economic conditions and cultural experiences have influenced employees.

But a generational label should never become a substitute for getting to know the individual.

Not every millennial wants the same career. Not every employee prefers the same communication channel. Not every ambitious professional intends to leave. And not every person who sounds confident feels prepared.

When leaders rely too heavily on assumptions, they begin interpreting behavior before understanding it.

An employee who asks about advancement may be highly committed to the organization. An employee who wants frequent feedback may be trying to improve rather than seeking constant reassurance. Someone studying for another degree may be expanding skills that could eventually benefit the company.

The behavior alone does not reveal the motivation behind it.

Strong leaders stay curious long enough to learn the difference.

Millennial Communication Styles: Confidence and Competence Are Not the Same Thing

Millennial communication styles have sometimes been characterized as unusually confident, casual or direct. But confidence and competence do not always develop at the same pace.

A young professional may speak comfortably in a meeting because they have been encouraged to participate throughout school. That does not mean they understand every workplace expectation surrounding the conversation.

Another employee may have considerable expertise but communicate hesitantly because the audience, culture or situation is unfamiliar.

Leaders should avoid rewarding confidence as though it automatically proves readiness. They should also avoid interpreting nervousness as a lack of ability.

Instead, consider three separate questions:

• Does the employee understand the work?
• Can the employee communicate that understanding clearly?
• Can the employee adapt the message and style to the situation?

Those questions provide a more useful view of professional readiness than confidence alone.

Millennial Communication Styles: Explain the Expectations That Experience Usually Teaches

Experienced professionals have absorbed countless unwritten workplace expectations. They know when to speak, how much context to provide and what level of formality a senior audience expects.

Early-career employees may not know those expectations yet.

A manager may believe a communication habit is obvious because it has become automatic. The employee may have no idea that the habit exists.

For example, “Be more executive” is not actionable feedback. Neither is “Read the room,” “Show more confidence” or “You need better presence.”

Leaders must explain what effective behavior looks and sounds like.

That could mean saying:

• Begin with your recommendation before sharing the background.
• Explain why this issue matters to the business.
• Pause after making your central point.
• Bring two options and tell us which one you support.
• Ask questions before assuming you understand the concern.
• Adjust the amount of detail based on who is listening.

Specific guidance gives employees something they can practice. Broad judgments usually leave them guessing.

Millennial Communication Styles: Make Feedback Part of the Working Relationship

Employees cannot adapt to workplace expectations they never hear about.

When managers avoid feedback, they may assume they are protecting the relationship or giving the employee time to learn independently. But silence often creates more confusion.

The employee continues repeating a behavior while the manager becomes increasingly frustrated. Eventually, the feedback arrives with more emotion and urgency than the situation required.

Consistent feedback prevents that buildup.

It also makes feedback feel like a normal part of development rather than a sign that something has gone terribly wrong.

Leaders can make feedback more useful by focusing on three elements:

The behavior: What did the employee say or do?

The impact: How did that behavior affect the audience, decision or outcome?

The adjustment: What should the employee try next time?

For example, a manager might say, “You gave us a great deal of useful detail, but the recommendation did not appear until the end. In the next executive conversation, begin with what you want the group to decide and then provide the information that supports it.”

That feedback is direct without being personal. It helps the employee understand both the expectation and the reason behind it.

Millennial Communication Styles: Ask Before You Interpret

A great deal of intergenerational tension begins with interpretation.

The employee sends a short message, and the manager reads it as dismissive. The manager requests an in-person conversation, and the employee assumes something is wrong. One person sees initiative while another sees overconfidence.

Before reacting, ask a question.

“What are you hoping to accomplish?”

“Tell me more about how you reached that conclusion.”

“How do you see this fitting with your role here?”

“What type of feedback would be most useful?”

“What did you want the audience to take away?”

Questions create room for context. They allow a leader to test an assumption before treating it as fact.

They also model an important communication habit for the employee. Curiosity is often more productive than certainty, especially when people bring different experiences and expectations into the same conversation.

Millennial Communication Styles: Communicate the Why Behind Workplace Decisions

Employees are more likely to understand an expectation when they know why it exists.

A leader may ask someone to attend a meeting in person, prepare a shorter summary or follow a particular decision process. Without context, those requests can feel arbitrary.

Explaining the reason changes the conversation.

Perhaps the in-person meeting involves a sensitive issue that will benefit from a more personal setting. Perhaps the executive summary must be brief because the leadership group is comparing several recommendations. Perhaps a particular process exists because the decision affects multiple functions.

Providing the why does not mean every decision must become a debate. It means leaders give employees enough context to understand how their work fits into a larger situation.

That context is especially important in a multigenerational workplace, where people may have very different assumptions about how, when and why communication should occur.

Millennial Communication Styles: Adapt the Channel to the Message

Discussions of millennial communication styles often focus on digital communication. But the more useful question is not which generation prefers which channel.

It is which channel best serves the message.

A quick clarification may be handled efficiently through chat. A complicated decision may require a scheduled conversation. Feedback involving emotion or nuance may be more effective face to face or through video. A formal recommendation may need written documentation after the discussion.

Leaders should establish shared expectations around:

• When to use email, chat, video or an in-person conversation
• How quickly different messages require a response
• Which decisions need written confirmation
• When a conversation should move out of a digital channel
• How communication expectations change during urgent situations

Clear norms reduce the likelihood that employees will interpret channel preferences as personal rejection, unnecessary formality or a lack of respect.

Millennial Communication Styles: Recognize That Ambition Can Signal Engagement

The original article describes a manager interpreting an employee’s law school preparation as evidence that she was already planning to leave.

That interpretation may have been accurate. It may also have missed an opportunity.

Ambitious employees often think ahead. They consider future degrees, certifications, positions and experiences. That does not necessarily mean they are disengaged from their current work.

A productive manager could begin with curiosity:

“What interests you about law school?”

“How does that connect with the work you want to do?”

“What skills are you hoping to build?”

“Are there experiences here that would support that goal?”

Those questions help the manager understand whether the employee’s ambition can be developed within the organization.

Even when an employee’s long-term plan eventually takes them somewhere else, investing in that person can still produce valuable work, stronger relationships and a positive impression of the organization.

Retention is important, but fear of eventual departure should not prevent leaders from developing capable people.

Millennial Communication Styles: Create Opportunities to Practice Leadership Communication

Confidence becomes more credible when it is supported by experience.

Leaders can help employees develop that experience by creating opportunities to communicate in increasingly challenging situations. An emerging leader might begin by providing an update, then explaining a recommendation, facilitating part of a meeting or responding to questions from a senior audience.

The assignments should be accompanied by preparation and feedback.

Before the conversation, ask:

• What is your central message?
• What does this audience care about?
• What questions are you likely to receive?
• What outcome do you want?
• How do you want to be perceived?

Afterward, discuss what worked, what the audience appeared to understand and what the employee should adjust next time.

This turns communication development into an ongoing leadership practice rather than a single training event.

Millennial Communication Styles: Use Content, Style and Situation

SW&A evaluates communication through three connected dimensions: Content, Style and Situation.

Content is what the person communicates. Is the message clear? Is the main idea easy to identify? Does the employee provide the right amount of support?

Style is how the person communicates. Does the employee sound confident, tentative, casual, defensive or prepared? How might the delivery influence the listener’s interpretation?

Situation is the context surrounding the interaction. Who is the audience? What does that audience expect? How much authority does the employee have? What organizational dynamics may affect the conversation?

This framework is particularly useful when examining generational communication styles.

What appears to be a style issue may actually be a content problem. What sounds overly casual in one situation may be perfectly appropriate in another. A message that works with peers may need to change when delivered to senior executives.

The goal is not to teach every generation to communicate in exactly the same way. It is to help leaders and employees make intentional choices based on the audience and desired outcome.

Millennial Communication Styles: Better Communication Begins With Fewer Assumptions

The most useful conclusion from the original survey was not that millennials fit a particular mold. It was that they did not.

Some participants were highly confident. Others were nervous. Some planned to stay with their organizations, while others were already considering what might come next.

That variety still exists within every generation.

Leaders communicate more effectively when they replace assumptions with questions, explain expectations clearly and provide feedback employees can use. Employees grow more quickly when they understand how their communication is being interpreted and learn to adapt without losing their authenticity.

Millennial communication styles may have started the conversation. But the larger leadership lesson applies to everyone: people want to be understood as individuals, and they need enough guidance to understand others in return.