The Best Question Ever And How To Help Others Grow

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Lead or be liked is bogus.

No doubt, one of the most challenging parts of leadership is facing into the conversations no one else will, but someone must. It’s also the most rewarding.

That’s where it’s at.

Growth happens in the last one percent, in the ‘thing behind the thing’ that most are unwilling to point out. And that’s why—leaders say what peers wish someone would say to their co-workers.

Unfortunately, that means not everyone will like you; but they will have to respect you—if you do it well.

I’m human.

I like to be liked, but I’ve learned to love watching others soar more.

So how do we help others grow?

We care enough to share what’s holding them back and walk with them through whatever’s next. 

When we do that, they begin to grow. And when your people start growing, they have no interest in going anywhere.

Simple right?

But there’s a catch.

If you don’t genuinely care, you need to focus there first. And possibly buy a nice tent. After that, it might be time for some camping.

That will make sense later. I promise.


Change can only happen when we’re made aware

I was sitting on the couch, aimlessly surfing the web on my phone, when I heard my wife say this doozy: “You’re gonna kill me for saying this, BUT there’s some cool stuff going on in temporary tattoos for eyebrows right now.”

We weren’t talking about eyebrows. I wasn’t asking about tattoos, and yet there I was, quickly deciphering the cryptic code she was sending.

My response: “Let me get this straight. I’m bald, and I have no eyebrows. So I’m PAC-MAN!!!! Am I missing anything?”

The truth is like an ice-cold shower: shocking at first but the fastest way to wake up.

Turns out my eyebrows aren’t what they used to be. Now that it’s been brought to my attention, I can do something about it. Not sure what, but something. Sharpie? Tattoo? –Thanks babe.

Approach is everything; being right is less important than being heard, which hinges on approach.

How’s yours?

If you can believe it, I would put the tattoo callout in the helpful category, but that’s ONLY because I married an Enneagram 8.

Hard truth is our equivalent of whispering sweet nothings to each other.

I knew what I signed up for so…

  • At home, that was music to my ears.
  • At work, that would make anyone want to resign.

For leaders, simply bringing “truth” is not good enough. We want to bring it IN A WAY that is easily digestible and actually fixable.

Translation: Doesn’t make people wanna quit.


The Best Question Ever

A former boss, mentor, and friend named Ray sat me down about five years ago and asked me the best question ever:

“If there was something holding you back from being the best leader you can be, would you want to know about it?”

Is this a trick question? Is it even possible to say NO without being a total clown?

My mentor.

He went on to tell me about a meeting he was in where a group of my colleagues were discussing a project deadline. Someone said, “Dave will follow up,” and there was collective laughter. Why? Well, clearly, they didn’t expect to hear from me.

I was a visionary without a daily planner. And I had a shadow reputation forming that I knew nothing about—until someone had the guts to tell me. Someone who loved me enough.

The clarity was blinding and ironically opened my eyes to reality.

It was a gift. I was awake.  

That was one of the best days of my leadership life. Sure, it was tough to hear but equally true and ultimately liberating.

It led me to actively identify people on my team with complementary strengths and find small systems (hacks) that could help mitigate my official ‘lack of follow-through’ diagnosis.

That said, I’m never going to be organized or “on it” in a Type-A way, but five years later, I have grown exponentially in this area, and no one is laughing anymore. At least about that.

And contrary to common fears, I like Ray even more today.


So, what did Ray do that allowed me to hear him AND want to change?

  • He cared enough to share.
  • He made me aware.
  • He did it in a way that I could hear.

Important reminder: You can’t control how people respond, only how you handle it.

Let’s break down his approach even more:

1. Be for, before.

  • He was for me.
  • He wanted what was best for me, not just at work, but also for the rest of my life.
  • And he made it clear well before the conversation.

Be for them, before the meeting.

Ray is an anomaly. When he was my boss, he made an absurd amount of time for me.

He took me camping, for crying out loud… twice!

It certainly doesn’t scale, but it was a crash course for me in building trust. Grabbing coffee is another great way to connect if you’re not a camper, or have more than one direct report.


2. When we ask, we make it theirs to own.

  • He asked if I even wanted to get better.
  • Some don’t… (wanna get better)
  • He didn’t assume I wanted to be the next Tony Robbins.   

Ray was higher on the org chart. He didn’t need my permission. But by asking, he made it mine to own.

Nine times out of ten, being intentionally curious about what’s driving a behavior will unearth a deeper understanding. Ten times out of ten that increases our empathy.

Asking questions means talking less. And just because you called the meeting doesn’t mean you should do all the talking!


3. Encouragement becomes powerful when contrasted with coaching.

  • He cared enough to tell me the whole truth.
  • He didn’t sugarcoat.
  • There was enough sting to get my attention.

The best leaders are like pineapple pizza. (Which we all know is the worst kind of za.) They bring the salt and the sweet, the coaching and encouragement. We have to do both.

If it’s only sweet, it’s incomplete—and likely insincere.

It takes no courage to only encourage.

What’s my point?

When you always sugarcoat, it can be hard to taste the truth.

Also…

When you always sugarcoat, it can taste really sour on the rare occasion when you don’t.

Specific examples are the best way to bring clarity without it tasting sour (feeling personal). Examples are more objective, give context to the problem, and allow you to offer up an alternative approach—which is often the lightbulb moment.

Ray’s story left little room for secondary narratives to form. So, I didn’t leave wondering if I was an all-around failure; I just needed to figure out my calendar.


Leading IS Leaning In

I’m living proof (based on how hard I office these days) that change lives on the other side of a hard conversation.

The sooner you can learn to hear what’s true, the faster you can become the best version of you.

What Ray did for me that day made me loyal for life but…

…it’s also a blueprint for building a culture that attracts and retains top talent.

Why? Because people want to grow.

When we are willing to help them see and set them free from what’s holding them back, they are unwilling to leave. (Am I Dr. Suess?)

The great resignation is not about salary; it’s about opportunity to grow and having somewhere to go in the organization.

Great cultures do both.


Leaders Help People Grow

The hardest words to hear have helped me grow the most. I’m so grateful for people like Ray, who cared enough to help me see what I could not.

Are you willing to be that for someone you lead?

If the answer is—you’re not quite ready to confront, you can always go camping.

Either way, be like Ray. Go change someone’s trajectory today.


Thanks as always for reading and reacting!

I hope it was helpful. If so, please let me know. If not, I’d love to know what would be in the comments below. What resonated? What made no sense? I want the salty and the sweet!

Subscribe if you want more insight about leading teams and building magnetic culture.

For all other inquires, hit me up!

9 Replies to “The Best Question Ever And How To Help Others Grow”

  1. I love reading your blog. It reads like I’m sitting across from you, idea leading to idea, the occasional tangent. (eyebrows?) I love that you are building the next generation of leaders with wisdom, self-deprecating humor, humanity, and grace. I’d follow you anywhere. Except to the tattoo parlor.

    1. ha! and wow. your words are SO encouraging Mike. every month I wonder if it’s worth it. -this fuels me to keep going. also, i’m not sure I’ve ever been able to tell the difference between tangents and main points….🤓

    1. wow thank you so much! your name shows up as “someone” -i’m so curious who you are. either way, thanks for reading and commenting. it means the world!

  2. I’m not always great at giving hard feedback… often too much sugar is included. You inspired and challenged me – I needed to hear this!

    1. Jamie! you and 99% of the world. We all default to sugar -thanks for reading and commenting. and btw, if you had to tip one way or the either, you’ve chosen wisely.

  3. This is such great insight. It is giving me clarity. I actually stepped away from a space about 6 months ago BECAUSE of poor leadership so everything you said hits home. Making the hard move has already caused growth in my life and hopefully in theirs, too. Many phrases stood out but I love this nugget… The sooner you can learn to hear what’s true, the faster you can become the best version of you. So many people are unwilling to hear truth but it does refine!

    1. so many! we all hear through a filter and it only hurts us in the end. thank you so much for reading and commenting. glad to hear your decision has led to growth, although i’m sure it hasn’t been easy. i’m curious what industry you work in???

  4. Once again I discovered numerous quotable lines in your blog. I agree wholeheartedly with your pineapple za analogy. Ray’s approach is clearly a winning strategy and you can’t underestimate the lasting impact of Boundary Water camping with your boss sans sanitary living conditions! Love your introspection and self-analysis with the goal of improving yourself, your staff and other leaders.

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