How to be Great at Worrying
Top 10 SaaS PPC Agencies (2026)
Equity Is the Most Expensive Currency Your Startup Has. Stop Treating It Like Bar Peanuts.
Can Startups Be a Team of One?
Why are We Really Building a Startup?
We Rarely "Control" Our Startups
The Problem With Never Being Done
What Should My Expectations Be?
What Actually Happens if I Run Out of Gas?
The Value of Side Quests
The Key to Success Is Mastering Failure
We Can't Predict the Future Anymore
We Wanted Efficiency. We Got Isolation.
Startups are the Future of Employment
The Founder "Hard Reset"
Where Does Our Optimism Come From?
When Popularity Destroys Productivity
Will Getting Bigger Make Us Better?
"Just Be Yourself" is Terrible Startup Advice
Embrace How Messed Up You Are
The Great Remote Workplace Reset
Can I Hire Someone to Run My Startup for Me?
How Founders Get "Fired by Promotion"
Burnout is a Treatable Injury
Stop Pretending You Don't Have Enough Time
Are We Aligned with Everyone Around Us?
Will the Payout be Worth the Sacrifice?
How Founders Blow Their Fortunes
When Should We STOP Asking for "More"?
Can Entrepreneurship Help Alleviate Poverty?
Should Employees Really be Our Friends?
Can Founders be Replaced by AI?
The Best Startup Fractional CMOs and Growth Leaders
The Best Growth Marketing Agencies: How to Choose Them and Who They Are
What if We Run Out of Goals?
Reinvention is Our Only Constant
We're So Connected — And Totally Lonely
The 10 Best Growth Agencies for Startups
My Roadmap to Becoming a Confident Leader
Is College a Waste of Time for Founders?
Are We Preventing Our Startup From Evolving?
Building a Startup That Loves You Back
When Our Friends Resent Our Success
When Our Startup Outgrows Us
When Being in the 1% Feels like Failure
We Need Outside Interests that Consume Us
If You're Not Terrified, You're Doing it Wrong
Why do Founders Suck at Asking for Help?
The Ideal Client Profile Is Your Startup’s North Star (Stop Ignoring It)
Are We Growing or Just Getting Fat?
Let's Get Back to Our Why
Does Startup Success Validate Us Personally?
How We Secretly Lose Control of Our Startups
Should Kids Follow in Our Founder Footsteps?
The Evolution of Entry Level Workers
Assume Everyone Will Leave in Year One
Stop Listening to Investors
Was Mortgaging My Life Worth it?
What's My Startup Worth in an Acquisition?
When Our Ambition is Our Enemy
Are Startups in a "Silent Recession"?
The 5 Types of Startup Funding
What Is Startup Funding?
Do Founders Deserve Their Profit?
Michelle Glauser on Diversity and Inclusion
The Utter STUPIDITY of "Risking it All"
Committees Are Where Progress Goes to Die
More Money (Really Means) More Problems
Why Most Founders Don't Get Rich
Investors will be Obsolete
Why is a Founder so Hard to Replace?
We Can't Grow by Saying "No"
Do People Really Want Me to Succeed?
Is the Problem the Player or the Coach?
Will Investors Bail Me Out?
The Value of Actually Getting Paid
Wait a Minute before Giving Away Equity
You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
Never Share Your Net Worth
A Steady Hand in the Middle of the Storm
Risk it All vs Steady Paycheck
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Why Having Zero Experience is a Huge Asset
My Competitor Got Funded — Am I Screwed?
The Hidden Treasure of Failed Startups
If It Makes Money, It Makes Sense
Why do VCs Keep Giving Failed Founders Money?
$10K Per Month isn't Just Revenue — It's Life Support
The Ridiculous Spectrum of Investor Feedback
Startup CEOs Aren't Really CEOs
Series A, B, C, D, and E Funding: How It Works
Best Pitch Decks Ever: The Most Successful Fundraising Pitches You Need to Know
When to Raise Funds
Why Aren't Investors Responding to Me?
Should I Regret Not Raising Capital?
Unemployment Cases — Why I LOOOOOVE To Win Them So Much.
How Much to Pay Yourself

Every One-on-One Meeting Should Ask This Question

SH
Shay Howe
Every One-on-One Meeting Should Ask This Question

one-on-one meeting

It’s not “How are you feeling?”

For years I’ve been having one-on-one meetings with my employees. These meetings are invaluable for building trust, providing feedback, and sincerely understanding how I may help each employee. They’re my favorite meetings as they’re also the most productive.

During each one-on-one meeting I go over the questions provided by Lead Honestly. These questions ensure we’re continually discussing new topics, creating new insights, learnings, and feedback.

There is also one question I ask during every one-on-one meeting. Given the nature of a one-on-one meeting, and it’s focus on an employee’s emotions, many are quick to guess that this question is “How are you feeling?” It’s not.

I’ve tried this question without much luck. For one, it’s a difficult question to start with. Opening the conversation with “How are you feeling?” can startle an employee, especially if they need priming before opening up. Moreover, after a handful of other questions, I should have a pretty good sense of how they’re feeling.

The better question I’ve found is…

What else is on your mind?

I ask this question towards the end of every one-on-one meeting, after the employee is comfortable and we’ve established a safe environment. It’s an open ended question that allows employees to air any thoughts or concerns that may be weighing on them. Additionally, it provides an inviting way for them share what else is important to them that we haven’t yet discussed.

Some of the best discussions I’ve had with employees have been driven by this question. If I may, I’d encourage you to give it a try. You may be surprised with the responses and the effectiveness you can create from such a simple question.

Find this article helpful?

This is just a small sample! Register to unlock our in-depth courses, hundreds of video courses, and a library of playbooks and articles to grow your startup fast. Let us Let us show you!

OR

GoogleLinkedInFacebookX/Twitter

Submission confirms agreement to our Terms of Service and Privacy Policy.