Sitemaps
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
Why do Founders Suck at Asking for Help?
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
The 9 Best Growth Agencies for Startups
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
Heat-Seeking Missile: WePay’s Journey to Product-Market Fit — Interview with Rich Aberman, Co-Founder of Wepay
The R&D technique for startups: Rip off & Duplicate
Why Some Startups Win.
Chapter #1: First Steps To Validate Your Business Idea
Product Users, Not Ideas, Will Determine Your Startup’s Fate
Drop Your Free Tier
Your Advisors Are Probably Wrong
Growth Isn't Always Good
How to Shut Down Gracefully
How Does My Startup Get Acquired?
Can Entrepreneurship Be Taught?
How to Pick the Wrong Co-Founder
Staying Small While Going Big
Investors are NOT on Our Side of the Table
Who am I Really Competing Against?
Why Can't Founders Replace Themselves?
Actually, We Have Plenty of Time
Quitting vs Letting Go
How Startups Actually Get Bought
What if I'm Building the Wrong Product?
Are Founders Driven by Fear or Greed?
Why I'm Either Working or Feeling Guilty
Startup Financial Assumptions
Why Every Kid Should be a Startup Founder
We Only Have to be Right Once
If a Startup Sinks, Founders Go Down With it
Founder Success: We Need a Strict Definition of Personal Success
Is Quiet Quitting a Problem at Startup Companies?
Founder Exits are Hard Work and Good Fortune, Not "Good Luck"
Finalizing Startup Projections
All Founders are Beloved In Good Times
Our Startup Culture of Entitlement
The Bullshit Case for Raising Capital
How do We Manage Our Founder Flaws?
What If my plan for retirement is "never retire"?
Startup Failure is just One Chapter in Founder Life
6 Similarities between Startup Founders and Pro Athletes
All Founders Make Bad Decisions — and That's OK
Startup Board Negotiations: How do I tell the board I need a new deal?
Founder Sacrifice — At What Point Have I Gone Too Far?
Youth Entrepreneurship: Can Middle Schoolers be Founders?
Living the Founder Legend Isn't so Fun
Why Do VC Funded Startups Love "Fake Growth?"
How Should I Share My Wealth with Family?
How Many Deaths Can a Startup Survive?
This is Probably Your Last Success
Why Do We Still Have Full-Time Employees?
The Case Against Full Transparency
Should I Feel Guilty for Failing?
Always Take Money off the Table

A Simple Trick for Less Awkward, More Effective One-on-One Meetings

Kennedy Collins

A Simple Trick for Less Awkward, More Effective One-on-One Meetings

A Simple Trick for Less Awkward, More Effective One-on-One Meetings

We’ve all read the articles, seen the reports, heard the advice: one-on-one meetings are key to running a startup effectively. So why is it that only a third of managers actually follow that advice and meet with their employees on a weekly basis?

In my experience, it’s because most one-on-one meetings are bad. They’re difficult in the best of circumstances, and that difficulty is often compounded by managers at startups being less experienced on average. The result is meetings that are poorly run, poorly planned for, and really, really awkward.

As humans, when we’re faced with an uncomfortable situation that will theoretically help us succeed in the long term but will be painful in the short term, we’re just not going to do it. This is true for going to the gym, for studying, for anything.

We’re wired to dramatically devalue rewards that exist far in the future and highly value rewards that are very near. This idea is so important to how we think that it’s a cornerstone of behavioral economics, where they call the concept hyperbolic discounting.

In practical terms, hyperbolic discounting means we’re wired to avoid one-on-one meetings. It’s rational to pick the near term relief of not going through an awkward one-on-one over the long term value of that one-on-one, unless we can either (a) internalize the idea that one-on-ones are in fact super duper valuable or (b) make them a lot less awkward. Let’s try to do both.

One-on-one MEETINGs are in fact super duper valuable

Former Intel CEO Andy Grove probably said it best:

“Let’s say you have a one on one with your subordinate every two weeks, and it lasts one and a half hours. Ninety minutes of your time can enhance the quality of your subordinate’s work for two weeks, or for some eighty-plus hours, and also upgrade your understanding of what he’s doing.”

 

One-on-one meetings are one of the most valuable things you can do to improve your company, hands down.

As a manager, you need to know how your employees are doing and what’s going on in your company in order to lead effectively. There are formal ways of collecting that information, such as status reports and task management systems like Basecamp and Jira, but formal systems track  formal work — they almost never pick up the half baked ideas, office politics, and non-work issues that constantly swirl around the formal stuff, and are often the real blockers in a business.

As an employee, the one-on-one meeting should be your venue to give feedback to your manager and the company at large, explore new ideas, and get feedback on your work — feedback you need to improve. Any manager or company that doesn’t provide that to you is not only robbing you of a healthy working environment now, but a brighter future as a more effective employee tomorrow.

To quote another former CEO, this time Ben Horowitz in The Hard Thing About Hard Things:

“If you are an employee, how do you get feedback from your manager on an exciting, but only 20% formed idea that you’re not sure is relevant without sounding like a fool? How do you point out that a colleague that you do not know how to work with is blocking your progress without throwing her under the bus? How do you get help when you love your job, but your personal life is melting down? Through a status report? On email? Yammer? Asana? Really? For these and other important areas of discussions, one-on-ones can be essential.”

 

There’s already lots of good advice out there about why one-on-ones are valuable, and how to make them effective in the traditional sense, so I won’t belabor the point. Horowitz has a good list of questions to ask on the a16z blog, there are also companies that help with the process such as 15Five, Lattice, Know Your Company, and Lead Honestly. All work, as long as you keep in mind that this is not a status report, it’s a discussion of how things are going outside formal channels.

It’s the employee’s meeting, not the manager’s. As such, the employee should be setting the agenda, and should be talking most of the time. The manager should be asking questions to tease out important issues, and then shutting up.

The simple trick for making one-on-one MEETINGs less awkward and more effective

Even when run well, the first couple one-on-ones with a new employee can be profoundly awkward. We’re talking tinder first date, meeting the parents, knowing no one at a party levels of awkward. Sitting in a room with someone you’re not close with and asking personal questions about their life and work is a categorically uncomfortable experience.

It’s not fun to experience, and it’s definitely not fun to watch. But we can take a cue from one of my favorite shows on how to make meetings more fun and dynamic: go for a walk.

In The West Wing, director Thomas Schlamme would spice up Aaron Sorkin’s dialogue heavy scenes by making them walk-and-talks through the hallways of the White House. At the time, those scenes were mocked for being unrealistic, but walking one-on-ones are actually used by some of the most well-known leaders around: Jack Dorsey and Mark Zuckerberg are both fans, having allegedly gotten the bug from the late Steve Jobs, as is LinkedIn’s Jeff Weiner; even non-fictional president Barack Obama used the walk-and-talk while he was still in office. You don’t just have to blindly follow their lead, either—there’s strong scientific backing as to why this is a classic trick of the powerful and effective.

The benefits of walking one-on-ones

By shifting the object of focus from one another to the sidewalk in front of you, both people in the meeting are able to focus on their thoughts and less on reading the reactions of the person next to them — serving the same purpose as a therapists couch. Physical activity also reduces anxiety and tension, which is key for diffusing awkward situations.

Reducing awkwardness is only the beginning of why you should do walking one-on-one meetings. If you’ve read anything else I’ve written, then you know how much I love to talk about how physical activity can improve cognition. The boost that walking gives to creative ideation and mood are particularly important for problem solving and building rapport, respectively, two of the key pieces of valuable one-on-ones.

Walking one-on-one meetings

Just make sure you’re walking somewhere where you can walk automatically. Research from the University of Michigan has shown that walking along paths and in parks can improve working memory, but all of those improvements are erased by the distractions of city walking. If you’re weaving through traffic,waiting at stoplights, and avoiding other pedestrians, then you’re not paying attention to the conversation at hand.

Back when I was working in downtown Chicago, we had a path along the riverfront that we would use for longer one-on-ones and other walking meetings. When we just needed a quick check-in, we would circle the block. In the winter, we would circle the office or just retreat into a conference room and have a catch. As you look for your walking path, remember: you need to be able to focus on the conversation — you’re looking for just enough stimulation to get the blood moving, not enough to distract.

Common Objections

  • I need to take notes. No you don’t. For most one-on-ones, simply jotting down action items at the end of the meeting is enough. Either start and end at the office (so you can review your previous notes at the beginning and make a couple quick notes at the end), or bring a pocket notebook.
  • I don’t have a good place to walk. Okay, do something else physical. Like I said earlier, one of my favorite meeting activities is tossing a ball back and forth. When was the last time you had a catch with someone? It’s really fun, and it’s proven to reduce anxiety.
  • Physical activity is too distracting. If what you’re doing is distracting, then you’re doing the wrong kind of physical activity. You probably shouldn’t be playing ping pong or doing pushups for the same reason that you need to have an “automatic” walking path — the point here is to keep your mind and body occupied without burning extra mental cycles, not to get a workout in at work.

If you have any other objections, I’d love to hear them. But for now, if you’re not already doing one-on-one meetings, start. Don’t overthink it. That’s beauty of working at a startup: you can make this change right now if you want. Just pick a few questions from the resources above, grab an employee — or your boss — and ask them to go for a walk with you. You’ll be making a measurable improvement in your team, your company, and your own well-being.

When it comes to health and fitness, it’s a lot easier to read advice than it is to put it in practice. That’s why I wrote a little booklet to help you get to the gym and follow through on your goals. Get it here: Five Scientific Strategies to Actually Get Yourself to the Gym.

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!

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

Already a member? Login

No comments yet.

Register to join the discussion.

Already a member? Login

Create Free Account