The Leader’s Toolkit: Questions That Unlock Truth in One-on-Ones

“Tell me one thing you really like about the organization, and one thing that frustrates you about the company?”

“Tell me what you do here, that’s not in your job description, that you think is really critical?”

“Tell me something you think I don’t know, that you think I should know, that is important?”

These questions come from The Corner Office, a former New York Times column by Adam Bryant, where he interviewed CEOs about how they lead. They remain as apt today as ever for senior executives looking to spark honest conversations in one-on-one interactions.

Other leadership thinkers have expanded this questioning approach. In Reinventing Leadership, Robert Townsend and Warren Bennis, and in The Hard Thing About Hard Things, Ben Horowitz, recommend CEOs ask questions such as:

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Fooling Ourselves: The One Question Every Leader Should Ask

A number of years ago, I asked members of my Mastermind group** to respond to the following question:

“How do I fool myself by holding a perception that is lesser or greater than reality?”

I posed this question because I know I have blind spots about how others perceive me.

Understanding how I come across – through the eyes of trusted colleagues – helps me avoid fooling myself about my impact.

Here’s the text of the email I sent after that Mastermind group meeting:

Subject: Thanks in advance / How do I fool myself by holding a perception that is lesser or greater than reality?

Hi Everyone,

At our last Mastermind meeting I asked Alan, John and Don to help me out. I asked them to consider this question about me:

“How do I fool myself by holding a perception that is lesser or greater than reality?”

…and to email me their thoughts.

I invite you Peter & Ian to do the same. I asked the guys to be as direct as possible.

The reason I’m seeking this feedback is because I know I have blind spots about how I come across or blind spots about how I am perceived by others.

For example: I may perceive myself as being inspiring, while another person might perceive me as overwhelming.

Knowing more about how others perceive me will help me understand myself better. Then I can take action – if warranted – to adjust how I behave, think, etc.

Be assured: whatever you say, I won’t take it personally. All of your perceptions are valid.

Thanks for considering this and for any feedback you provide.

Cheers,

Michael K

In addition to feedback about my vitality and energy I projected, one person offered a gem I was unaware of. Namely:

That I came across as a bit of a know-it-all.

Since then, I often acknowledge this perception early in my client work. I might say:

“I know I can come across as a know-it-all. I want to assure you I definitely don’t believe I know everything about this topic – though I’m always striving to improve.”

There are formal tools (like 360-degree feedback instruments) designed to give insight into how others see us. But these can be cumbersome, time-consuming, and often fraught.

By contrast, when asked of someone you trust, this “How do I fool myself?” question can provide valuable, actionable feedback –  quickly and directly.

**(A Mastermind group is a group of like-minded people (in my case solo business owners) who meet regularly to help each other in a particular venture or interest. Here is a link to a PDF by Jack Canfield on how to set up and run a Mastermind group).

Own the Conversation

In the next seven days, take a risk:

Send your own adapted “How do I fool myself?” request email to someone you trust.

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P.S.Here’s a prior post of mine, that might interest with advice from jazz great, Theolonius Monk, titled Thelonious Monk and memorable speaking

My analysis of Konstantin Kisin’s powerful speech at ARC 2025

Some of you may have seen this stellar and provocative 15-minute presentation by Konstantin Kisin at the February 2025 ARC Conference, delivered to an audience of world leaders.

Leaving aside the merit of Kisin’s ideas, here’s my analysis of his performance as a communicator:

 What Kisin Did Well

  • Hooked the audience early

    He opened with a deadpan comment about not complaining about Britain, followed by a tongue-in-cheek comparison to Aleksandr Solzhenitsyn – drawing a warm, unforced chuckle. (Every presenter should aim for a sincere, early smile or laugh from the audience.)

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Why Your Voice Matters More Than Your Looks

Is having a “pretty voice” more important than having a pretty face? According to research by Miron Zukerman and his associates at the University of Rochester, the answer is yes. They found that college students with highly attractive voices were rated as having more pleasant personalities than those with less attractive voices. Interestingly, while facial attractiveness also played a role, the impact of voice was stronger.

This research, as shared in the book Why We Don’t Talk to Each Other Anymore, raises an important question: Do you have an attractive voice? And should you even aim to have one?

The truth is, striving for a “pretty voice” is the wrong goal. Instead, focus on understanding how your voice is perceived by others and learning how to use it more effectively to enhance your influence.

To begin mastering your voice, it’s essential to confront a reality most people avoid: listening to their own recorded voice. This often feels uncomfortable because your voice sounds different on recordings than it does when you speak.

Here is a post explaining why your voice sounds different on an audio recording

Own the Conversation

The First Step to Vocal Influence

Start by recording short audio clips of your voice. Here’s how:

1.In the seven days leading up to your next presentation, use your smartphone to record the opening 45 seconds of your presentation.

2. Listen to this clip three times a day at four-hour intervals.

3.Repeat this process daily until the day of your presentation.

Why This Works

By repeatedly listening to your voice, you’ll gain a deeper understanding of how it truly sounds, reducing your aversion to hearing it on recordings. More importantly, you’ll create a mental “audio file” that you can draw upon to deliver your presentation with greater confidence and authority.

Are you ready to make your voice work for you instead of against you?

World Champion Toastmaster Speech: What Worked & What Didn’t

Some of you may have seen the impressive 7:50-minute presentation by Mohammed Qahtani (MQ), the 2015 Toastmasters International World Champion.

My Analysis of the Presentation

Overall, Qahtani’s delivery was world-class. His opening hook was one of the best I’ve ever seen. He kept the audience engaged through:

• Expertly paired facial expressions and words

• A well-controlled speaking cadence

• Strategic pauses

• Unexpected, deadpan humour balanced with serious points

A clearer takeaway message would have made the presentation even stronger.

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The Power of Simplicity: Why Clear Messaging Matters More Than Ever

“Verbal expression is the mirror of the mind. Clear thoughts become clear statements, whereas ambiguous ideas transform into vacant ramblings.”

Clarity in communication is deceptively difficult. The world is complex, and forming truly lucid thoughts requires focused mental effort. Until that clarity is reached, Mark Twain’s timeless advice remains true:

“If you have nothing to say, say nothing.”

Simplicity isn’t where we begin—it’s the result of careful thinking and refinement.

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Can You Handle the Truth? The CEO Feedback Challenge

Do You Want to Keep Me as CEO?

Over the last three months, did I get better at this job or worse? Why?

Phillip Rosedale, founder of Linden Labs, challenges every CEO to ask their employees these direct questions—every quarter.

Rosedale put this into practice during his tenure as CEO, using anonymous surveys to gather unfiltered feedback. The results? Reduced friction, improved communication, and a more cohesive workplace.

In an interview with Kevin Rose, Rosedale explained how this process worked. Here’s a breakdown, along with his insights from Executive Careers:

“The beauty of the survey lies in its simplicity.”

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Crafting the Perfect Best Man Speech: Proven Tips and Ideas

I recently worked with a client who was feeling a bit nervous about delivering a best man speech. Before our one-on-one session, I crafted a few potential openings for him, as well as some key pointers on structure and delivery. Here are some of the ideas I shared, which might help you or someone you know who’s preparing for the big moment.

Opening Section
The first sentence of a speech is critical—it should hook the audience immediately. Here are a couple of options for an impactful start:

  • “This, is a happy day… This… is a very happy day.”
  • “I never thought this day would come, but I am so glad it has.”

A strong, memorable opening sets the tone for the rest of the speech, so take time to craft it.

Middle Section
For the body of the speech, stick to three key points or anecdotes to keep it structured and engaging. Here’s a guide:

  1. When you met the groom: Share a fun or heartfelt story from the early days of your friendship.
  2. A memorable experience: Talk about a special or humorous moment you’ve shared.
  3. The significance of your friendship: Highlight what the friendship has meant to you over the years, using a personal example.

People remember things in threes, so keeping it concise and focused will make your speech more impactful.

Closing Section
A classic closing is a toast to the couple. For example, “Please stand and join me in toasting [Groom] and [Bride].”

Here are a few extra tips to make your speech stand out:

  • Timing is key: Speak for no more than four minutes (240 seconds). Less is more!
  • Add a light touch: Aim to get an early, un-cheesy smile or chuckle from the audience to put everyone at ease, including yourself.
  • Own the conversation: Project confidence and sincerity. This is your moment, so embrace it fully.

Own the Conversation

Implementation Idea
If you or someone you know is preparing for a best man speech, these tips could make all the difference. Save or share them as a helpful guide for crafting a memorable and heartfelt speech.

Let me know if you’d like more detailed advice for an upcoming event!