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Feb 16, 2025

Feb 16, 2025

Feb 16, 2025

Lessons learned: The Problem with Being "Too Chill" as a Manager

Lessons learned: The Problem with Being "Too Chill" as a Manager

Lessons learned: The Problem with Being "Too Chill" as a Manager

Stephanie Goldman

Stephanie Goldman

Stephanie Goldman

Founder at Gridlines

Founder at Gridlines

Table of Contents

Lessons learned: The Problem with Being "Too Chill" as a Manager: Finding Balance Between Autonomy and Authority

"Just do your thing" - that's been my management philosophy since day one. I've always believed in creating a work environment where independence reigns supreme. Where talented professionals can spread their wings without a manager constantly hovering over their shoulders. It sounds perfect in theory, right?

But recently, my husband pointed out something that hit home. After overhearing one of my team calls, he noticed a pattern I'd been blind to: my dedication to being "chill" was making my management style ineffective, particularly when giving feedback or direction.

The Autonomy Paradox

Here's the thing about being a laid-back manager: it's great until it isn't. While fostering independence is crucial for team growth and satisfaction, there's a fine line between being hands-off and being unclear. I've learned that sometimes, in our attempt to be non-confrontational and maintain that easy-going atmosphere, we dilute important messages to the point where they lose their impact.

Consider these two ways of addressing the same issue:

Too chill: "Hey, when you get a chance, maybe think about updating the project timeline... it seems like we might be falling a bit behind."

Effectively direct: "I need you to revise the project timeline by Wednesday to account for the two-week delay we're experiencing."

The first version might feel more comfortable to deliver, but it fails our team by:

  • Creating ambiguity about expectations

  • Downplaying the urgency of the situation

  • Leaving room for misinterpretation

  • Potentially requiring multiple follow-ups, which actually creates more work and stress for everyone

Finding the Sweet Spot

The good news? You don't have to choose between being approachable and being effective. Here's how to maintain your laid-back leadership style while ensuring your team gets the direction they need:

1. Reframe Direct Communication

Think of clear, direct communication as a tool that enables independence rather than restricts it. When you provide explicit expectations, you're actually giving your team the framework they need to operate autonomously. They can make confident decisions because they understand exactly what success looks like.

2. Structure Your Feedback

Use the Situation-Behavior-Impact model to keep feedback clear and professional:

  • Situation: Identify the specific context

  • Behavior: Describe the actual actions taken

  • Impact: Explain the consequences

3. Create Regular Check-in Rhythms

When you establish regular one-on-ones and team meetings, direct feedback becomes part of the natural flow of work rather than feeling like confrontation. These consistent touchpoints also prevent small issues from snowballing into bigger problems that require more intensive intervention.

4. Use Clear Language

Replace hedge words with direct statements:

  • Instead of "maybe you could," say "please do"

  • Instead of "when you get a chance," say "by Friday"

  • Instead of "it might help if," say "I need you to"

The Path Forward

Being a "chill" manager doesn't mean being an ineffective one. The key is recognizing that clear direction and autonomous work environments aren't mutually exclusive - they're complementary. By providing clear expectations and direct feedback, you're actually enabling your team to work more independently because they understand exactly what they're working toward.

The next time you need to give feedback or direction, try this approach:

  1. Be clear about what you need

  2. Explain why it matters

  3. Set specific timelines

  4. Express confidence in their ability to execute

Remember, your team isn't looking for a friend who happens to be in charge - they're looking for a leader who can help them succeed. Sometimes, the most supportive thing you can do is be crystal clear about what that success looks like.

Your relaxed management style is an asset - it helps create a positive work environment where people feel trusted and valued. Just make sure you're not sacrificing clarity in the pursuit of being easy-going. After all, the most stressful thing for employees isn't a manager who's direct - it's a manager whose expectations are unclear.

About the Author

Stephanie Goldman

Stephanie Goldman

Founder at Gridlines

I enjoy the intersection between finance and software engineering. I previously worked at Barclays as an Investment Banking Analyst and at GI Partners as a Private Equity Associate.

I enjoy the intersection between finance and software engineering. I previously worked at Barclays as an Investment Banking Analyst and at GI Partners as a Private Equity Associate.

I enjoy the intersection between finance and software engineering. I previously worked at Barclays as an Investment Banking Analyst and at GI Partners as a Private Equity Associate.

Boosting analyst efficiency by automating document analysis and slide creation for investment banks

Product

AI-Powered slide creation

Data validation

Use Cases

Pitch book creation

CIM development

Client presentations

Ad hoc materials

Due diligence analysis

Market updates

Industries

Investment Banking

Private Equity

Consulting

Company

About Us

Careers

Gridlines, Inc. © 2025. All rights reserved

Boosting analyst efficiency by automating document analysis and slide creation for investment banks

Product

AI-Powered slide creation

Data validation

Use Cases

Pitch book creation

CIM development

Client presentations

Ad hoc materials

Due diligence analysis

Market updates

Industries

Investment Banking

Private Equity

Consulting

Company

About Us

Careers

Gridlines, Inc. © 2025. All rights reserved

Boosting analyst efficiency by automating document analysis and slide creation for investment banks

Product

AI-Powered slide creation

Data validation

Use Cases

Pitch book creation

CIM development

Client presentations

Ad hoc materials

Due diligence analysis

Market updates

Industries

Investment Banking

Private Equity

Consulting

Company

About Us

Careers

Gridlines, Inc. © 2025. All rights reserved