This article explores what Microsoft’s Hackathon and Garage activities reveal about employee behavior—and how those behaviors connect with psychological safety, self-directed growth, cross-functional collaboration, Learning Agility, coaching-based management, and next-generation leadership development.
When people think of Microsoft, they often think first of products such as Windows, Azure, Microsoft 365, and Copilot.
But this time, we are looking at something different:
the behavior of the people who work there.
What happens when employees notice a problem, cross organizational boundaries, ask for help, and act without waiting to be told?
Through a conversation between Dash and Peemo, we explore what those behaviors reveal about Microsoft’s Smart Work.
Employees Who Don’t Say, “That’s Not My Job”
Dash:
Peemo, let’s start with what employees actually do.
What stood out to you?
Peemo:
One thing is how easily people seem to cross boundaries.
At Microsoft Hackathon, employees from very different functions come together.
Engineers.
Salespeople.
Marketers.
Designers.
Researchers.
Different departments.
Different countries.
Different areas of expertise.
But if they see an idea worth pursuing, they look for the people they need and form a team.
Dash:
So they are not necessarily waiting for the company to assign them a project team?
Peemo:
No.
Some people bring their own ideas.
Others find a project they want to join.
And if they need expertise they do not have, they look for someone who does.
They may even approach people they have never worked with before.
Dash:
That is interesting.
In some companies, the response might be:
“That’s not our department’s responsibility.”
But here, the behavior seems closer to:
“I noticed something. Let’s see what we can do.”
That connects strongly with cross-functional collaboration and autonomous action.
Peemo:
Exactly.
The interesting part is that collaboration is not only a formal structure.
It becomes something employees initiate themselves.
Not Protecting Your Own Idea
Dash:
What happens after the team comes together?
Peemo:
The original idea often changes.
They try something.
They show it to others.
They get feedback.
If it does not work, they change it.
Then they try again.
Dash:
That sounds simple, but it is not always easy.
People naturally become attached to their own ideas.
Peemo:
Right.
But what matters is not protecting the original idea.
What matters is improving the outcome.
Dash:
That connects with Learning Agility.
The key question becomes less:
“How much do you already know?”
and more:
“How quickly can you learn from experience and change what you do?”
Peemo:
That is one of the behaviors we keep seeing.
If something does not work, the response is not necessarily:
“We failed.”
It is more like:
“What do we need to change next?”
Being Able to Say, “I Don’t Know”
Dash:
There is another point I find interesting.
Microsoft has many highly capable people.
But highly capable people can sometimes find it difficult to say, “I don’t know.”
Peemo:
That is where Microsoft’s emphasis on being a:
“learn-it-all” rather than a “know-it-all”
becomes important.
Instead of proving that you already know the answer, you acknowledge what you do not know and continue learning.
Dash:
So in everyday behavior, that means:
Ask when you do not know.
Listen to people who see things differently.
Change your own thinking when necessary.
Peemo:
Yes.
And those behaviors are closely connected with psychological safety.
Dash:
Psychological safety is often misunderstood as simply creating a friendly workplace.
But perhaps it is more practical than that.
Can I say:
“I don’t know.”
“I disagree.”
“I made a mistake.”
“I need help.”
If people can say those things, learning becomes much easier.
Peemo:
And so does collaboration.
Managers Are Not Expected to Have Every Answer
Dash:
What about managers?
Peemo:
Microsoft uses the framework:
Model, Coach, Care
to describe the role of managers.
The “Coach” element is especially relevant here.
Managers are not expected simply to provide answers.
They ask questions.
They listen.
They help employees think through problems for themselves.
Dash:
So the role changes from:
“Because I am the manager, I should know the answer.”
to:
“Because I am the manager, I should help you think.”
Peemo:
Exactly.
That is close to what HR often calls coaching-based management.
And it also supports self-directed growth.
The goal is not to make employees dependent on the manager.
It is to help them think, decide, and act for themselves.
Leadership Before the Title
Peemo:
There is another behavior worth noticing.
Employees do not need a leadership title to act like leaders.
They notice a problem.
They bring people together.
They propose an idea.
They test it.
They involve others.
Dash:
That is an important point.
Leadership does not necessarily begin after promotion.
It can appear much earlier, in everyday work.
So perhaps next-generation leadership development should not focus only on:
“Who should become a leader?”
It should also ask:
“How do we bring out leadership behavior in more employees?”
Peemo:
That may be one of the most useful lessons here.
What Are We Really Seeing?
Dash:
If we step back, what patterns do you see?
Peemo:
A few are especially clear.
Employees:
cross boundaries.
ask for help.
work with people who are different from them.
test ideas.
learn from feedback.
change course when necessary.
act without waiting for a title.
Dash:
And when we translate those behaviors into HR language, we see familiar themes:
Psychological safety.
Self-directed growth.
Cross-functional collaboration.
Learning Agility.
Coaching-based management.
Next-generation leadership development.
But I do not think Microsoft employees are consciously thinking about those terms every day.
Peemo:
Probably not.
The more interesting question is:
What makes these behaviors possible in everyday work?
Dash:
Exactly.
Is it the culture?
The way managers behave?
The way teams are formed?
Or perhaps something deeper—
the way people ask questions, think, and engage with one another?
Peemo:
That is where Microsoft’s Smart Work becomes especially interesting.
The visible behavior is only the surface.
The next question is what kind of thinking and dialogue make that behavior possible.
Akira Chida / Dash
SmartWorks