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InSmartBudget > Leadership > You’re Making It Hard for People to Be Honest With You — Here’s How to Make Them Finally Speak Up

You’re Making It Hard for People to Be Honest With You — Here’s How to Make Them Finally Speak Up

News Room By News Room May 10, 2025 6 Min Read
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If you’re a manager, your team might hesitate to give you updates. If you’re a founder, your customers might not give valuable feedback.

This is awful, right? You don’t think of yourself as intimidating! But here’s the problem: You haven’t given them permission — because you didn’t think you needed to.

When you fix this, you’ll become a better friend, leader, and partner. So let’s start by looking at the power of permission, and then extend it to you.

My friend Jenny Wood is a former Google executive, and the author of a great new book called Wild Courage. She recently got into a Lyft that was freezing cold — but she didn’t feel comfortable asking the driver to turn the heat up. So she suffered silently.

Related: 5 Proven Tools for Developing Strong Relationships as an Entrepreneur

Then Jenny saw a sign the driver had hung in the back seat. It said: “If you need anything, feel free to ask.” So she did! “The sign gave me permission,” she told me. “It’s permission I didn’t even realize I needed.”

In theory, 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 your feelings, or worry that their request isn’t welcome. That’s why Jenny didn’t speak up in the cab at first — 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. So whether you like it or not, it is your job to continually create the opening. You must give others permission, just like that Lyft driver did, and then reinforce it over and over again.

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 forget. Or they worry that your offer expired.

Related: Why Creating a Culture of Feedback is Vital to Business Survival

I asked Jenny: Did she ever create permission while at Google, running a large organization with many direct and indirect reports?

“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: 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 that included “a project you’re excited about” and “a skill you want to develop.”

She also included some frivolous topics, like “something fun you did this weekend,” to lower the bar for conversation.

One of her Google colleagues went a step further: In addition to 20-minute blocks of time, they also offered five-minute blocks. “She wanted to send a signal,” Jenny said, “that you don’t have to have some fancy presentation to talk to the big boss.”

Given that, 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?”

→ 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. Invite them for a catch-up.

Related: 8 Strategies for Building Long-Lasting Business Relationships

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.

If you’re a manager, your team might hesitate to give you updates. If you’re a founder, your customers might not give valuable feedback.

This is awful, right? You don’t think of yourself as intimidating! But here’s the problem: You haven’t given them permission — because you didn’t think you needed to.

When you fix this, you’ll become a better friend, leader, and partner. So let’s start by looking at the power of permission, and then extend it to you.

Join Entrepreneur+ today for access.

Read the full article here

News Room May 10, 2025 May 10, 2025
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