My Nine Questions (Who Do You Listen To?)

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[May 5, 2018]

I love to learn. I suck at reading fiction, but I am willing to bet that I’ve already read your favorite book on business or self-improvement.

Lately, I’ve been loving learning about myself. It’s amazing how much a forty-three-year-old man hasn’t known about himself up until this point in life — whether it relates to family and relationships, or business and occupation, or whatever.

College never taught me much about any of it. I don’t believe in college.

I mean, I believe in college as a thing that exists — like a tree or something — but I don’t think that college is worth the price you pay for it. Not unless you want to be a doctor or go into some profession that warrants that kind of niche expertise.

I saw a guy post something on Twitter the other day who said, “YouTube is a college for free.”

That’s probably an overstatement, but in our day and age, I do think that one can just as easily create her version of a trade school. She does that by following the experts who are teaching whatever she wants to learn, directly — maybe buying their e-courses and learning specifically about how to make her passions sustainable — without all the absurd prices of general education indebting people to the system.

Of course, my daughter wants to go to college because — as an Enneagram No. 1 — it’s the right way to do it. So, despite what I think, God may decide to giggle and give me that thorn in the flesh.

Anyway, I’m getting off on a tangent that I’ve already written about, but the point is this:

Who do you listen to? Who do you learn from?

And not only when it comes to education specific to schooling, or what you do, or want to do.

What about who you are?

I’ve heard an author say that most people end up becoming more Human Doings than Human Beings. This is the kind of education I’ve been most excited about lately, and it’s a lot more about who I am than what I do.

Most people I know are learning about or working on a lot of what they’re doing, but very few are invested in self-awareness or — if they somehow have that — doing anything about what they know.

They say that college is supposed to prepare you for life. Maybe that’s another reason I’m skeptical. I went to college, but most of what I’ve learned has been self-taught and tested through trial and error, and over the past couple of years, I’ve begun to invest more in various types of atypical education, like people I trust.

I’ve paid for classes to learn from the best in the fields applicable to my business — copywriting, Facebook advertising, product launch formulas-you name it.

I’ve also paid for more counseling and therapy — in various forms (personal, marital, familial, spiritual, etc.) — than ever before.

I joined Jeff Walker’s Platinum Plus Mastermind group so that I could replace “trial and error” with “tried and true.” It’s funny, I bought in for business, and though it has undoubtedly been helpful there, the invaluable lessons I’ve learned have had far more to do with family, faithfulness to them and the life we want to build and live together.

Years ago, my friend Drew Melton decided to start paying for a life-and-business coach. It completely transformed his world.

Over the years, I’ve come to realize that I, too, have become an expert (of sorts) in my field of work. For some reason, that feels like an embarrassingly egoic statement to make, but I’m only paying forward the words of other people in my life who have helped me accept it as true.

When I consider it, I do suppose that I have become a go-to guy for answers to questions that my friends have, especially — it seems — when related to business and family.

Last year, I applied for a position at a life-coaching firm. I love helping people fix problems and move past barriers in their lives, and had been a sort-of coach for a handful of friends for a while by that time, anyway. I was curious about what “going official” was all about. I wanted to try it. See what the process was like. See if I could be an educator, of sorts, in this kind of one-on-one, licensed-stamp-of-approval world. See if I’d like it at all.

It turns out; I didn’t. It wasn’t for me, but I’m glad I tried. Had I not explored the possibility, I would have missed out on one of the single-most impactful exercises I’ve ever undertaken in my life.

As a part of the application process, I was required to send a list of nine questions to a minimum of five friends or family members who I trust the most, and ask them for honest answers:

  1. Why do you think I will make a good coach?
  2. What do you see as my greatest challenges in becoming a powerful coach?
  3. How could I get in my own way?
  4. How would you rate my integrity?
  5. Do you trust me?
  6. Tell about a time I have hurt you or you have been frustrated or disappointed with me?
  7. When have you seen me at my best?
  8. My worst?
  9. If you could wave a magic wand what would you want to see happen in my life that isn’t currently happening?

To say that asking these questions — let alone reading the answers — was a vulnerable process is an understatement. It didn’t take long to realize how invasive the responses might feel. Nevertheless, I paid them forward and — knowing how intimidating it might be for some of my friends-and-family members to respond truthfully — promised that my feelings would not be hurt by whatever they had to say.

I’m Michael Scott. Roast me, Dunder Mifflin.

What follows is a summary of what I learned, specific to each question asked.

  1. Why will I make a good coach?

I want to see people succeed — to see their dreams come true — and will do what I can to make sure that it happens. I can see the problem — whatever is holding someone back from success — very quickly, and I won’t bullshit them about what needs to change. I take a big-picture perspective and cut straight to the point, challenging people to think outside the box and see what they might not currently be able to.

2. What are my greatest challenges in becoming a powerful coach?

By far, the most consistent feedback I received from everyone on this question was concerning impatience (which includes unclear communication), and a lack of empathy. It makes sense, and is — to me — a perfect example of the adage: “Your greatest strengths are your greatest weaknesses.” The positive side of fixing problems quickly is, well, problems quickly get fixed. But not everyone works like me, and it comes across negatively when I see where people “should be,” and get frustrated when it takes them too long to get there (whatever “too long” means). When it comes to empathy, I find it difficult to put myself in someone else’s shoes. Sometimes, that leads to generalizing or misunderstanding the problem at hand and coming across as insensitive or dismissive.

3. How can I get in my own way?

The responses here were a bit more varied, but what stood out most to me were the descriptions intimidating and lack of compassion. That sucks to hear. I place a high premium on clear-cut, no-nonsense answers. I know I’m opinionated, too, which isn’t inherently wrong, but if I think something or someone is pathetic, for instance, I could also stand to figure out a better word for expressing it.

4. Am I a person of integrity?

Yes. Flying colors, unanimously. So, that’s encouraging.

5. Am I trustworthy?

Yes across the board.

6. When have I hurt or disappointed my friends and family?

These responses sucked to read. I know I’m nowhere near perfect, but asking for straight, specific answers to a question like this is hard. I suppose they come as no surprise, especially as I learn more and more about myself. I place too much pressure on my wife — spiritually, emotionally, relationally. I publicly berated a coworker and left him feeling incompetent. I dropped a relationship when I felt like it wasn’t worth fighting for. I’ve joked at other people’s expense. I’ve made dumb decisions and justified them instead of humbling myself and apologizing.

7. When am I at my best?

It’s funny; this one seems to have the most to do with presence and leadership, particularly in a fatherly role (though it applies to both family and business). My wife told me that “it is has done wonders for our family to see you breathe and be present.” Nearly everyone had something to say about the way that they’ve seen my anxiety lessening, and my ability to lead well increasing because of it, so nearly all of the “best times” are more recent experiences. That’s encouraging and feels progressive like it will continue.

8. When am I at my worst?

Unfortunately, I received almost identical feedback from everyone in response to this question, all related to the way that I handle conflict. Words like “belittling,” “insulting,” and “intimidating” are not adjectives that a boss, father or husband wants to be described by, and although “playing the victim” — I suppose — makes sense in conjunction with the rest, it’s equally disheartening. Coming face-to-face with your inconsistencies (or, your less-than-helpful consistencies) isn’t comfortable, especially when every person you ask raises their hand in unanimous assent to that ugliness.

9. What would people make happen in my life that they don’t currently see if they could wave a magic wand and see it appear?

I think the gist of these responses can be summarized by the same words people used to describe me at my best: when I slow down. My wife straight up said just that, whereas others had more nuanced ways of getting there. For example: “strategize instead of quick-starting everything.” I’ve got to slow down to do that. “Delegate tasks.” As someone who is used to wearing every hat, I’ve got to take them all off (slow down) for long enough to know what or how to delegate, and then trust whoever takes over enough to slow down.

Sitting with everyone’s responses at the end of this exercise was an eye-opening experience equal to any other form of education I’ve previously received. Here, laid out in front of me, was a series of answers from my closest friends and family about who I am and how I function.

When I say “eye-opening,” it’s not necessary to infer that I discovered something new, but rather: what I know is now confirmed. Bluntly, blatantly and unavoidable. There is even unanimity in the feedback, so I can’t argue my way out of the discomfort, and now that all of these people know I’m in the process of understanding myself and progressing where change is needed, the question becomes:

What am I going to do about it?

After all, information is not synonymous with transformation.

When I switched glasses, so to speak, and began to look at all of this feedback through a pragmatic lens, I was able to come to concrete conclusions and start to implement change.

Practically, when it comes to my weaknesses:

  • If people are telling me that I suck at communication over text and email, I’m going to start using Voxer — a voice messaging, walkie-talkie style app — and give them more context that way.
  • If people are telling me that I am dismissive in our conversations because I’ve overbooked phone calls and meeting times for the day, then I’m going to start using Calendly to make sure that I am available and that they feel more appreciated, and less like a task box that needs checking off.
  • An addendum to the above; it’s great that I have a calendar system set up for phone calls, but what boundaries should I place on that? When and on what days those calls should take place?
  • If I lack empathy, then I want to surround myself with people who are better at it and can help me say what I mean to. I hired Levi to help me with most everything — including what you’re reading right now — because he’s the best empathetic writer I know, and when he did this “Nine Questions” challenge, everyone responded the same.
  • If I’m spread too thin, then I need to have some difficult conversations with people. I need to drop clients. I need to stop working on things — some of the perfectly fine and good things — that aren’t my things. Like Greg McKeown says, “If it’s not a hell yes, it’s a no.”
  • If I’m overworking, then I’m probably not enjoying the life that I’ve created — and neither is my family. I need Sabbath. We need to rest. I’m not going to be good at what I am good at without the rest necessary to fuel my work. I need to create healthy rhythms to function inside of.
  • If I tend only to change when life forces it upon me, then how can I learn to ask people for feedback before it gets so bad that we’re devastated by it? Before my wife comes to me and says, “I refuse to live another twenty years like this. Change, or I’m out.”
  • If I’m not good at details, but Jeanette needs them to function, then how can we learn to lean into one another’s strengths and work in complementary ways rather than feeling as though we’re just taking on one another’s shit leftovers, and things the other doesn’t want to do?

On the flipside, this questionnaire also helped me confidently acknowledge my strengths. It became more comfortable for me to make these changes because I now have the affirmation of those who know me best saying, “Do it, Craig. Pursue the things that you’ve been too afraid of stepping out in faith for because you are good at them. Our responses are staring you in the face, cheering you on. There’s no excuse to hold back anymore.”

So, I’ve done a lot since then, including doing less, more and what I’ve kept or started, better.

I know that I’m good at connecting people, so I created a mastermind of my own, with the people who I love and think stand to benefit from that connectivity, most. I built a room. (And, I made everyone in that room pay these questions forward to five of their friends and family members, too. The snowball is rolling.)

I created, as well, which has allowed me to outsource many of the hats that I’d previously wear myself for our ministry endeavors, as well as other projects we run as subcontracted through that entity.

I’ve led our family through considerable changes in the way that we function — many of which I’ve already written about, and more than I want to share with people moving forward.

The question is this:

How do you find clarity?

What are the things that you shouldn’t be doing?

What are the things that you should be doing?

This was an unspeakably clarifying exercise for me, and after suggesting that many more of my friends, coworkers and family members risk the susceptibility it takes to do the same and ask others for feedback, I’d like to recommend it to you, as well.

Trust me, from someone who has been personality-typed as having the most challenging time with vulnerability; I promise it won’t return void. Not a few of my friends have commented upon it as the single most beneficial thing they’ve ever done. For their businesses? Sure. But more-so for themselves, and every relationship within their proximity.

Of course, not everyone wants to be a life coach, so let me offer an edited, more applicable version of these questions for you to use as you wish. This series has replaced “coach” with “leader,” as everyone — in one way or another — leads someone.

If you need to hone it in even more specifically for your circumstance, feel free, but for now:

  1. Why do you think I am a good leader?
  2. What do you see as my greatest challenges in my business?
  3. How could I get in my own way?
  4. How would you rate my integrity?
  5. Do you trust me?
  6. Tell about a time I have hurt you or you have been frustrated or disappointed with me?
  7. When have you seen me at my best?
  8. My worst?
  9. If you could wave a magic wand, what would you want to see happen in my life that isn’t currently happening?

Two more things (and this is me working on my empathetic side):

First, I’ve realized — through frustration at past challenges given to friends and left unfulfilled — that not everyone has five people close enough to trust with questions like these. Whether that is truth or perception, I’ve got to be gracious there.

I’d encourage you not to get stuck on a number. Send the questions to a couple of people, or one person. Hell, Levi sent his list to his mom. No one’s not the right person if they have your permission to speak into your life this way.

Brene Brown says that “courage starts with showing up and letting ourselves be seen,” and that, “vulnerability is the birthplace of love, belonging joy, courage, empathy, and creativity… our source of hope.”

She also says that shame can’t survive in an environment filled with understanding, and no matter how uneasy I was about the answers I might receive, I found that to be true, as well.

Healthy and authentic relationships, it seems, are built off of both the permission to be and the ability to receive things that are both tough and tender from one another. No matter how alone you may feel; you aren’t. Maybe sharing these questions is an opportunity — a challenge, even — to risk the vulnerability necessary to start building the kinds of relationships you want to have in the first place.

Do it.

Oh, and finally: if you want to go to college; whatever.


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