Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to achieve a breakthrough at work — and build a career or company you love.
Today’s edition is sponsored by Vanta — the all-in-one trust management platform. Details at the end of the newsletter.
You may not realize it, but someone is afraid to talk with you.
If you’re a manager, your team might hesitate to give you updates.
If you’re a business owner, your customers might not give you valuable feedback.
If your friends or partners are in need, they might not turn to you first.
This is awful, right? You want to be warm and welcoming! And you don’t think of yourself as intimidating.
So what’s the problem? It’s this: You haven’t given them permission — because you didn’t think you needed to.
Today, I’ll show you how to fix this problem — making you a better friend, leader, and partner.
But first, let’s look at a small moment where someone was afraid to speak up:
“Um, excuse me…”
My friend Jenny Wood is a former Google executive, and has a great new book called Wild Courage: Go After What You Want and Get It.
In the book, she tells a brief story that I really related to. Here it is:
The other day, I got into a Lyft to the airport. The car was freezing. However, I shivered silently instead of asking the driver to turn on the heat. The truth is, I didn’t want to make the driver uncomfortable, even though I had every right to avoid frostbite.
Ugh, this is so me. Like, if I’m getting a massage at a spa, and the pressure is so intense that I’m in pain, I will literally grit my way through it instead of asking the masseuse to lighten up.
But then Jenny noticed something: Her Lyft driver had a sign in the backseat that said, “If you need anything, feel free to ask.” And that included AC/heat. Like this:
With that, Jenny felt comfortable speaking up. “The sign gave me permission,” she told me, when we talked about this. “It’s permission I didn’t even realize I needed!”
Now here’s why this story is so powerful:
We should all be giving permission.
If people want something from us, they should just ask. Right?
But let’s deal with reality: They probably won’t ask. They may fear being a burden, or don’t want to hurt our feelings, or worry that their request isn’t welcome. That’s why Jenny didn’t speak up in the cab, and why I don’t interrupt the masseuse. Instead, we all stay quiet — leading to a worse experience for everyone.
If people are not asking you for what they want or need, that’s inhibiting your ability to build stronger connections and become a better leader, friend, and partner.
Maybe you think you’ve already covered this. If you’re a manager, you might tell people you have “an open-door policy.” You might tell your friends, “I’m here for you anytime.” But as time passes, people might forget. Or they worry that your offer expired.
So whether you like it or not, it is your job to continually create the opening. You must give others permission to approach you, just like that Lyft driver did, and then reinforce it over and over again.
I asked Jenny: Did she ever do this when she was at Google?
“Yes!” she said. “People on my team were nervous to meet with me. They weren’t sure what would justify taking my time.”
So she set out to fix that…
What permission can look like
Jenny ran a large org at Google, with many direct and indirect reports, and she wanted them to feel consistently welcome approaching her. So she created a weekly block of time for “office hours”, and sent the invite to everyone.
It said that anyone can book a 20-minute slot with her — and then, to alleviate any anxiety about what’s worth discussing, she provided conversation topics.
Here’s what it looked like:
She intentionally included some frivolous topics, like “something fun you did this weekend,” because she wanted to lower the bar for conversation.
One of her colleagues at Google went a step further: They offered 5-minute blocks of time, not just 20. “She wanted to send a signal,” Jenny said, “that you don’t have to have some fancy presentation to come talk to the big boss.”
You can also give permission directly
As I talked to Jenny, I was reminded of my friend Jordan Harbinger, who hosts a big podcast. Every few months, I get a text from him that basically says: “Hey, how you doing? Anything I can help with?”
I love those texts. They prompt us to catch up — and every so often, yeah, I actually do have something he could help me with.
But now I realize something: In those texts, Jordan is really giving me permission to ask him for favors!
Yes, in theory, I could always ask Jordan for help. But I might have hesitated otherwise. It’s anxiety striking again — I might think, “Jordan offered to help a few months ago, but maybe he’s not in the mood anymore. So I won’t ask.”
That’s why Jordan needs to renew the permission.
Want to get next-level with this? Get ready: Jordan literally keeps track of people in a CRM, the way salespeople track their clients. I know that I’m in that CRM. I still like it. Because although his system may be automated, the connection is human.
Give someone permission today!
Here’s a challenge I hope you’ll take: Today, you should give someone permission.
- Maybe it’s your team. Like Jenny, you could find a simple and lasting way to invite them in.
- Maybe it’s a partner. You could ask: “Hey, it’s been a while since we’ve checked in. How are you feeling about the project? Any concerns we can discuss?” That might open a conversation they’ve kept to themselves.
- Maybe it’s a friend. If they haven’t heard from you in a while, they might wonder if you’re too busy for them, or if your feelings about them have changed. Invite a catch-up.
Relationships are like bridges. Some are big and strong, like a friendship or partnership. Some are narrow and temporary, like a customer in your Lyft. But no matter what, most people will eventually wonder: “Can I still cross that bridge?”
It’s time to put up a giant, flashing, neon sign that says YES! When you renew people’s faith in the bridge, they will cross it. And you will both be stronger for it.
I am giving you permission to do this.
That’s how to do one thing better.
And for real, I really do recommend Jenny’s book, Wild Courage. It’ll make you bolder!
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