Category Archives: 5 questions

5 questions with Tim Walker

You may remember that I started a series of 5 questions posts awhile back. I haven’t put one up for awhile. The last one, a conversation with Kay Ballard, has such an atrocious introduction that I couldn’t put up a new one without ap0logizing publicly (I’ve already taken care of that privately), and I couldn’t figure out quite what to say.

However, the best way you do what you don’t know how to do, Tim Walker would probably say, is to do it.

So know that Kay is a good friend, all the more evident because of her graciousness in private as well as in public. We have known each other through twitter for a year or so, we tease each other, and talk by email. Sometime we might actually talk by phone. She encourages me more than you know (and likely more than she knows).

Now, go back and read 5 questions with Kay Ballard and then come back and read my conversation with the aforementioned Tim Walker.


Tim Walker lives in Austin and is working on a doctorate in history at The University of Texas (“hook ’em Horns”).  (He has a really cool day-job with Hoovers, too.)  We started talking because I was intrigued with the Austin connection (having a degree from there myself) and because he introduced me to the concept of “deliberate practice.”  That concept has shaped my thinking for the last year in remarkable ways.

Tim also keeps pushing me (and all of us) on getting rid of multitasking and just working. He’s really annoying that way. Which is, of course, why I wanted to ask him five questions.

1. You are, by training, an historian. Your writing for Hoovers is about the present. What aspects of being an historian shape how you write about (and think about) now (in contrast to the occasional delightful historical presentations you do (the Gutenberg one, for example)? (How much is the way of thinking, how much is the training of just being a scholar, how much is the long view, how much is ___)

I hope that my historical training brings me two things: (1) a long-view perspective, and (2) a critical eye for evidence. The second point should be common to all scholars, whether they’re in the humanities, the social sciences, the hard sciences, or a professional field like business or law. Good scholars constantly ask “But how do we know?” — and, when evidence is presented to answer that question, they then ask, “But how do we know this evidence is valid?”

Bringing that back to my work, I see many assertions about business — Twitter, for one, is full of them — that link causes to effects in ways that a scholar couldn’t support. Yes, I see that A happened and that B happened, but how do we know that A caused B? What if B caused A? What if A and B both arose from C? What if A and B arose one after the other by pure coincidence? Or by some much more complicated string of causes and effects? It pains me when people draw a straight line from A to B based on their own ideological leanings or their own shortsighted self-interest. So I try to provide a corrective for that.

Getting back to my first point about long-view perspective, it also pains me when people make assertions that are uninformed by historical knowledge — and especially when they make glib assertions about how something (poster child: social media) “is totally unlike anything we’ve ever seen.” Well, no, it isn’t totally unlike anything we’ve ever seen — and the parallels between Thing X and what’s gone before are actually quite instructive. So I try to instruct a bit, but always with a spoonful of sugar (humor, stories) to help the medicine go down.

2. You write against multitasking. I’ve been thinking about why we do bits of so many things at once. I’m wondering if, for pleasers in particular, it’s a way of keeping as many people partially happy as possible. Because there are so many “I can do that for you” commitments on the todo list, the pleaser does a little bit of every one of them to keep people happy. The result, of course, is that everything falls behind. Does this make sense?

It makes perfect sense, and in fact it’s common for extroverted ADD-ers (ahem) to be pleasers. We make sense of the world by relating to people, we have interests in a large number of things, we get frustrated or bored when we have to stick to any one thing for too long, and if we’re lucky we may even have talents that span many areas. So we try to do it all and please everyone.

The reason this is categorically unwise is that every single one of us is going to die.

Here’s what I mean: our time is finite. To make the most impact, we must — absolutely, incontrovertibly must — focus our attention on just a few areas if not on one. (You can be the exception to this rule if you’re Schweitzer or Goethe. I’m not.) Multitasking is a lazy, fearful, and death-aversive response to this reality.

(Aversion to thoughts of death, by the way, is a major problem for most people in our culture — but maybe that’s a topic for a separate discussion.)

3. You make your Hoovers writing have a very personal voice. However, it isn’t Tim the whole person because it is a business blog. You have, I think, struggled with keeping a personal blog going. When we write so personally for work, does that complicate the private blogging? (and does that question make sense?)

The question makes sense, but I don’t think that’s the logic that has hampered my personal blog. My lack of time- and priority-management has hampered my personal blog.

And, by the way, I think you’ll see a much higher output — on both blogs — in the months to come.

4. “Have you been working out?” You tweeted about someone saying that. Why are you going back to fitness (and what triggered it?)

We’re ridiculously spoiled in this country. We’re fat and lazy. This is not an effort to channel the colonel from Dr. Strangelove (“precious bodily fluids”), but just an observation about the ailments — physical and otherwise — that waylay us.

I figure I have several mutually reinforcing obligations to keep myself in good health:

  • Our bodies are a blessing to us, and we’re beholden to be good stewards of them.
  • As a father and husband, I’m intent on modeling healthy behaviors for my family.
  • As a friend to many, I’m intent on modeling healthy behaviors for those around me.
  • Being fit is important to me psychologically, to the point that if I don’t do it I feel like I’ve betrayed myself. That’s not a good spot to be in.

On top of all of this, lifting weights and running are fun and meditative activities for me.

5. Do I remember correctly that you grew up in a pastor’s family? What should we not assume about kids that grow up that way (including my own two kids)?

We shouldn’t assume that they’re fundamentally different from other kids, just that they grow up under more scrutiny for their behavior. And, to put it mildly, sometimes it’s the scrutiny itself that leads to adverse behavior.


5 questions with Kay Ballard

I wish I could tell you how I met Kay. I don’t know. Somehow on twitter, I think. We’re talked that way, some by email, some in comments on posts back and forth. I’ll let our 5 questions introduce her more.

1. You describe yourself as a “recovering lawyer.” I’m guessing that means that being a lawyer is an addiction? What is so addictive, and how is that different than most other professions? (Or did you mean that you mostly are about property recovery cases)?

I admit without shame that the description of myself on my twitter profile is somewhat disingenuous.  I call myself a recovering lawyer there because so many find that description amusing.  When I say it, it ALWAYS gets a laugh. This confounds and amazes me, yet I bask in it.

Here is how the lawyer thing happened. For years I said to myself, “I wish I had gone to law school.”  “I should go to law school.”  “I want to go to law school.”  Eventually I did–The Ohio State University College of Law. Here is the punch line: I never even noticed or thought about the fact that I had never said, “I want to be a lawyer.” This realization happened after the deed was done.

I had my own “boutique” estate planning firm in Ohio, serving clients who, at that time, had net worths of 3-10 $million.  I loved my clients and helping them with tax planning, philanthropic planning, business continuity planning, and legacy planning.  I had a successful practice, happy clients, and a fat bank account.  I worked very hard to build and maintain my practice, but I didn’t “burn out” as a lawyer. When I made the decision to dissolve my practice, it was because I wanted to try something new. And I did.

But,I shall always be a lawyer. I am licensed to practice law in Ohio and Illinois. Currently I am seeking the opportunity to be Of Counsel to an Intellectual Property / Technology firm. I am a good lawyer and an excellent rainmaker.  I suppose I shall never fully recover.

2. You are starting a soiree, a social media soiree. If I understand, that’s like a talking party, where people get to mingle and chat, but the music isn’t so loud that you have to shout, and people are getting intoxicated on words and ideas rather than cocktails. Why do you find ideas so intoxicating?

Thank you for asking your question about ideas by framing it around the Social Media #Soiree. As you know, the Social Media #Soiree is a project that involves a 30 member production team, most of whom share my love for ideas.  And, that I suppose is the point I would make–loving ideas doesn’t make me unique.

But, Jon, you use the word intoxicated to describe my orientation towards ideas, so perhaps you have sensed something more. Here’s the more:  Yes, I am intoxicated with ideas–my own ideas. I laugh as I write this because I laugh at the truth of it.  I am totally, crazy in love with my own ideas. Frequently, I am the only one who sees the beauty of my ideas. But fortunately, that arrogant belief in the beauty of my own ideas, a dangerous form of self-confidence, has mostly served me well.

3. A tax collector in first century Israel would have been a wealthy low-life. So when one of them had a big party and invited Jesus to come and meet his friends, the professional clergy were pretty critical. But why would they have invited Jesus anyway? Isn’t he the last person that would have been invited?

The story you tell is easy for me to imagine. Everything we know about Jesus would make us believe that he would be the perfect party guest.  He was charismatic and well-spoken. It was said that he performed miracles.  He was provocative and had powerful enemies. Anyone would have found him fascinating. Having him as a party “get” would ensure an interesting party that the tax collector’s friends would want to attend.

Your story reminds me of the industrial barons in this country who built huge, ostentatious mansions (“cottages”) in Newport, Rhode Island to permit them to meet and entertain an eclectic assortment of celebrities. I myself would like to own such a cottage so that I could invite guests as diverse as Henry Kissinger, Cher, Alice Waters, and you, Jon for a weekend pageant of a party.

4. You tweet. A lot. As far as I know, you don’t blog, and I keep waiting for more to show up at your website. Are 140 characters easier than paragraphs or are they different in some significant way?

Jon, I like to write. I mostly like the writing I do whether it is for business or pleasure. However, I tend to be too wordy and long winded. And my emails are widely known as Russian novels. Friends and colleagues actually begin to weep when they spot an email from me in their inboxes.

Several years ago, I had half a dozen blogs. Strangely enough, at the time, I didn’t really want any readers. I told myself that I needed first to “find my voice.”  One of my blogs was called “Can’t Marry Me.”  Everyday it featured a prominent man from the obituary section of the New York Times. I would speculate somewhat briefly about what my marriage to that particular man might be like but for the fact that he was, well, dead.

As you can see, I was no great loss to the world of blogging.

Despite that, I have every intention to return. I own over 80 domain names, and who knows?  I might end up having a blog on every one of them. I laugh at that notion.

As far as twitter, I just love it and have dozens and dozens of fun conversations with dozens and dozens of friends there. Since I fancy myself amusing, I tend to be rather silly there–when I am not being outrageous.  The truth is, I have made wonderful connections with any number of dynamic and high achieving people, you among them.

5. I just remembered that you lived in Chicago for awhile (or maybe it was that you visited).  So which is better: Gino’s East pizza or Texas brisket?

I have never lived in Chicago, but I have taken a bar exam there, seen Sarah Bernhardt’s one woman show there, discovered the art of Julian Schnabel there, raised money from major donors there, shopped like Paris Hilton on speed there–you get the idea. Chicago is a place to have fun. But for the bar exam, Chicago, for me, is and has always been, a destination. I love it. You can’t get a park downtown. It is deadly cold in the winter. But there are plenty of cabs and you can wear a fur coat on the street.  I love Chicago.


This is one in a series of 5 Questions conversations. For more information, go to my 5 Questions page.

5 questions with C.C. Chapman

C.C. Chapman loves his family. Although he does lots of social media stuff, he regularly mentions his family. That’s what got my attention a couple years ago or so when I first noticed him. That matters to me.

He also can explain social media well. I was driving through the mountains two years ago and sent him this text:

listened to the first half of your podcamp nyc managing hte gray podcast while driving through the mountains of tenneesse. thanks. battery dagerously low. hit send now.


In spite of that typo-ridden message, he replied and we’ve noticed each other since.  I loved asking him 5 questions, particularly because the questions … and his wonderful answers…helped me think more broadly about story.

(Funny. I never thought to ask what C.C. stands for.)

1. With The Advance Guard, you’ve been helping organizations tell stories using more than one medium. Some of us use stories to make a point in a post. Jesus told stories as the point. What you are doing is saying “You know that story you want to tell? That really big one about a clothing line or a social issue?  Use three posts and a face-to-face and a video and a treasure hunt.”  Am I understanding what you do correctly?

I never thought I’d hear a description of what my company does and what Jesus did in the same paragraph before, but when you boil it all down I could make a lot of comparisons between the two. As you know The Advance Guard recently was acquired by Campfire so now I may be working under a different banner but the goal is still the same.

Our clients want to engage a community and get them involved in telling the story about the movie, car, product or clothing line. At the end of the day it does not matter what you are selling. If you can get people excited and passionate about what you want them to be then your job is being done right. Companies bring in us to develop a compelling marketing campaign that will get people talking. This isn’t just about buzz, even though that is a big part of it, but rather about having a great story that people will want to tell others or better yet be part of. That is how I like to thank about what we are doing.

2. Are you trying to help us understand story differently or are you helping us understand that our lives are stories, lived in multimedia?C.C. Chapman and Chris Brogan

Wow man, that is a DEEP question that should be discussed at length in big leather chairs away from the world, but since you are asking me here I’ll take a stab at it.

I think it is a combination of the two. Many people hear the word “story” and think of picture books and novels. But, for me it is much more then that. When I get to know someone I want to know their personal story. Every day when they tweet, write, share and interact with me it is adding to that story.

I want people to realize that they have a story to tell and that they can be part of a brands story as well. This could be as simple as sharing their thoughts about it with a friend or as crazy as taking part in a live event that is part of a larger narrative. The Internet and all the great tools people are building to interact with it allow for complete strangers anywhere in the world to become part of the story and that is what excites me because we are just starting to cut into the edges of what can be done and honestly the sky is the limit pushing forward. It will constantly be a challenge for people like us to outdo ourselves.

3. I’ve heard that millennials are seeking experiences. It sounds like you are working to satisfy that need on behalf of organizations.

I pray that it isn’t just the millennials who are thinking this way. To say that others are not interested would be like everyone going to the theme park and no one riding the roller coasters. *grin*

But, yes we are working on trying to satisfy this thirst for something more than just the status quo. But, while people might think this only works with big entertainment properties or other things of that ilk we have also done it for other properties such as the Verizon FiOS  My Home 2.0 project where we had a home make over show that was complimented by offline neighborhood block parties and online DIY videos targeted to various verticals. Finding the mix is key.

4. So, I’m a church or a non-profit. I’m, in the words of Peter Drucker, trying to change the world. What does your understanding of story and experience and multiple-media experiences tell me about how to bring about that change? And how can we afford that?

I’d be lying if I said having a bigger budget doesn’t make things easier, but talk to any filmmaker and they will tell you that sometimes not having the budget is good because it forces you to be more creative. That is what it boils down to; you’ve got to get extra creative. I also think it is key to be surrounded by people who are equally passionate about changing the world with you. When you don’t have money, you need passion more then ever.

I’m a huge music fan and I have watched numerous indie artists think way outside of the box and figure out ways to get their music heard, make money and find new fans all with almost no budget. Yes, it takes good old-fashioned sweat equity to change the world when you don’t have a pile of cash.

How to answer this question? It isn’t an easy one for sure. I think you need to set goals. Set little ones and big lofty ones. Work on accomplishing the little ones while always thinking “how can I reach that brass ring that is so far away?” That will keep you and your team motivated. Use every tool and every opportunity to let people know you are changing the world and NEVER be afraid to ask for help from each person you meet. That is the best advice I can give you now.

5. How cool is it to watch your daughter make movies that make guys in Indiana try new ice cream products?

I can’t even begin to tell you how big of a smile this gives me. ( I’m very proud of Emily’s creativity and unbridled “let’s do it” attitude. I have a feeling as she grows over that will turn a little bit scary, but I want her to be a strong willed woman and I have no doubt she will be. I’m a very blessed man to have two awesome kids who are growing up way too fast.


This is one in a series of 5 Questions conversations. For more information, go to my 5 Questions page.

Photo of CC Chapman and Chris Brogan taken by CC Chapman

5 questions with Chris Bowser

Mike and Chris (on the right)

I met Chris Bowser about 18 months ago when we came to Grabill Missionary Church. We have talked a lot, face to face, on the phone. However, if you aren’t in our geography, you don’t know much about him at all. That’s why I asked him 5 questions. (Turns out, he could be a pretty good blogger. 🙂

1. You are, I think, a “here’s how we can do that.” kind of person. That’s different from a “should we do that” or a “what are three ways that a person could do that.” kind of person. Is that a fair characterization? If so, how did you get that way?

Your characterization of me being a “here’s how we can do that” kind of person is correct.  I am a problem solver; that’s how God made me, how He wired me per se.  I don’t mind analyzing a “should we do that” situation but am much more suited to figuring out how to do it.  I am flexible enough to accept that there are other ways to do “that” but willing to offer a solution (not the only solution).  I got that way primarily because of three things; a tremendous curiosity, extreme independence (not always good) and tenacity.  I grew up without my Dad being around.  I had to develop solutions to problems that arose in the house and in our family.  Whatever solution path I took, I took after careful observation and thinking it through (step by step visualization).  Often times, I made mistakes due to my independent nature but I learned from them as well.  My tenacity really paid off because I did not care how long it took to do something if it got done right and to my satisfaction.  In short, I never had time to ponder if something should be done or alternate ways to do something – I just had to do it; there wasn’t anybody else to do “it”.

2. One of the things you do is lead a team that tries to figure out how to help people who have financial needs. Why do you care so much about people who have pain in their lives?

I care because I know what it is to hurt.  Growing up we struggled financially.  Sometimes we worried about not having enough money to cover our basic needs.  Dad wasn’t much help.  He was more worried about his latest female conquest than providing for his fractured families (plural).  People helped.  God heard us cry out to Him.  I watched – and never forgot.  I have had to work for everything I ever got, but it made me appreciate hard work.  It made me understand what real struggle is like.  It made me appreciate having a job, a way to provide for my family.  I understand sacrifice, people sacrificed to help us.  Over 20 years ago, God blessed us with a little girl after multiple miscarriages.  After only a couple of days, He took her back.  We went home empty handed and shut the door to the nursery.  My arms ached to hold her.  They still do.  It took a long time, but I realized that Jesus carried me through this desolate wilderness.  He never left my side; He was there when we held Erin as she died, He cried with us, He loved us and He loved her.  He took her home.  For me, caring about people who hurt comes naturally.  I care because I hurt too.  God uses us to reach out to others in need.  He blesses us for a reason.  It isn’t to reward us for our “good” behavior, it is to help others.  Our reward is already laid up for us in heaven.  That said, why wouldn’t we want to help ease the burden of someone who hurts?

3. You struggled with high school (not IN high school, because that implies aptitude challenges. You have no problems with aptitude.) What made high school so annoying?

I am so unlike other people.  I have always felt like a square peg in a round hole.  Peer pressure for me was never a problem.  I was independent enough that I just didn’t care what others were trying or doing.  If I wanted to try something, I did.  If I thought it was a stupid idea, I didn’t do it.  Learning was the same way for me.  If I liked it, I did it and I did it well and put everything I had into it.  If I liked the teacher and felt they were competent to teach me their subject, I did well too.  However, if I felt the teacher was not up to the task or I didn’t like the subject or I failed to see the relevance of the subject to my studies, I did not try as hard or did only what I needed to do to get the grade.  I wasn’t right with God back then and it was obvious.  I was very critical of others even though I wasn’t on the right path.  My biggest problem with high school was all of the social cliques.  They seemed so stupid and petty.  Many of them worried about clothes, their hair, their cars (or lack of cars) and treated even good friends with very little respect. In short, they were concerned about things that didn’t really matter and had total disregard for things that did matter and that really ticked me off.  It was boorish.  I played a lot of practical jokes and my antics and bad attitude (not my grades) kept me out of National Honor Society (another clique).

4. When you look at God, what do you see?

When I look at God, I see the father that I never had on earth.  Someone who is always there.  Someone who cares about me even when I mess up.  I see an open lap.  The lap I often crawl up on when I pray.  He holds me and loves me.  He always accentuates the positive things I do without beating me up over the stupid things I do.  He loves me period.

5. You are on facebook, but you hardly visit. You don’t tweet or blog. So what’s the deal? Why are the limitations you see to your involvement in social media?

Wow. Now I’m getting beat up.  I don’t know how to tweet.  I don’t know how to get started blogging.  I can’t imagine anyone wanting to read what I have to say.  I have little time to spare (an excuse).  I very much prefer a face to face conversation.  I like to look people directly in their eyes when we talk.  I like to read body language and I’m good at it.  Being strange, it’s easy for me to be misunderstood and it’s easy for me to misunderstand.  Written conversations exacerbate those misunderstandings for me.  I do enjoy talking on the phone (as you know) to close friends who know me fairly well and are not apt to misinterpret what I say.  I do like short stuff on text messages…


This is one in a series of 5 Questions conversations. For more information, go to my 5 Questions page.

5 questions with Amber Naslund

coffee and klondike barsI met Amber Naslund at SOBcon 2009. Briefly. That’s the face-to-face part. She writes marvelously well about social media and listening. So I decided to ask her 5 questions about the connections between her learning there, in the rest of her life, and how we can interact in all of our worlds.

1. Radian6 is about listening. Much of my local community, the church I am on staff with, is not talking online, at least not about us. We are on facebook ( and have moved there on purpose, but if I used Radian6 to vanity search, it would be pretty quiet. But people are talking offline, I’m sure. How should we listen? What have you learned about online tracking that works offline?

Sometimes, listening is about paying attention to a broader conversation. So the idea of listening just for vanity searches can be limiting, especially for smaller or new communities. So the idea is to spark conversation that’s bigger than your “brand”; find out what larger topics and interests your community IS talking about and host conversations about the things that matter to them. It’s a give-first kind of approach.

As for offline, the same principle applies. Gathering your community together and being interested and helpful goes a long way. Find out what’s on their minds. Ask. Be attentive and invested in the discussions and issues that have their attention. You can bring those conversations, online or off, to whatever places they’re gathering. Your own brand becomes the architect rather than the subject of those conversations, but the trust and affinity builds as a result by demonstrating that the interests and needs of your community come first.

2. What lessons in remodeling your house teaching you about how someone could renovate a reputation, on and offline?

Patience and time. Patience and time. There is nothing consistent about home renovation except the unexpected. That means that being methodical, patient, and attentive to detail matters a great deal. And owning the mistakes – and taking the time to go back and repair them – is what ensures that a project all comes together.

Reputations are funny things; you have control over what you put out there, but not so much over how it’s interpreted. For businesses and individuals alike, online reputation is a balance of appearances, perceptions, and what you demonstrate actively to the world around you. Put out there the things you’re proud of. Be humble (no one does it alone). Own your mistakes, acknowledge them, and move past them. And recognize that humanity is one of the most powerful brand attributes of all.

3. You actually have communication degrees, right? (You’ve heard of rhetoric, I think.) How does the study of communication help you focus on effective use of media rather than the bright shiny objects?

Actually I don’t. 🙂 My degree (singular, in fact) is in Music Performance. I’m a classically trained flute player with a rusty couple of  piano hands. I’m terrible at guitar.

But I can tell you that music has its own kind of lessons (and I even wrote about it once: The bundle of all those things is probably that the culmination of an amazing piece of music takes dozens of moving parts – people, instruments, practice, practice – and it’s a marathon, not a sprint. Truly great performances come from months of rehearsal. Shiny objects in social media are the means, not the end, and it’s the mastery of the intent behind the tools that matters most.

4. In what ways does having a child help you (make you) think about social media differently?

Wow. Well, it definitely makes me more conscious of personal accountability on the social web. My actions don’t just affect me, they can potentially affect the people I love – and the choices are mine. So, it makes me careful to behave in a way that I’d be proud of 10 years from now, and that my daughter would be proud of when she’s an adult.

I definitely think it also highlights to me that evolution, growth, and progress are unstoppable. Things never really stay the same, and we have to learn to embrace change as much as we can. Finding the underlying intent (again) – being human, being helpful, being friendly, being kind – is the constant in social media. The rest is just how we get there. There’s nothing that can point that out to you sometimes more profoundly than the crystal clear, simple and unfettered views of the world through the eyes of a child (as she grows up much too fast).

5. There is a lot of talk about brand evangelists these days. You have done some of it yourself. What makes me smile is that many people who are leery of evangelists in the religious sense, embrace the word in the business sense. Further, part of the reason that there is distrust of the religious kind is because so often those people have been after the sale and haven’t done the ongoing teaching, living explaining. It’s what we call making disciples. Is there a risk that brand evangelists will run into that same problem…and that the solution is the same–make disciples rather than converts? Make followers rather than clones?

Absolutely. Without question. That’s the essence of it all, really.

Being an evangelist isn’t about barking a pile of bullet points. Evangelism, in its truest form, is about sharing why you think something is worth following or believing in. We often miss the mark in business because even we don’t believe what we’re saying; we’re just reading off of a script, and that shows. We’re not taking the time to understand our value and our importance in the eyes of the people we’re hoping to reach, and we’re certainly not doing it on a personable level often enough. We see ourselves as job descriptions with responsibilities, instead of stewards of a company, part of the same communities we hope to build, and caretakers of the people that support our business. Humanity and business success can and should coexist.

Disciples aren’t created, either. They’re invited, and the choice is theirs. They need to feel as though you’re investing in them as much as they’re investing in you. It’s a relationship of trust and shared belief in something, not transaction. And having the benefit of those kinds of advocates for your business means a long term investment in those people over time. It doesn’t scale well, it’s lots of work, it’s fraught with the unexpected, and it’s deeply rich and rewarding when you get it right.


This is one in a series of 5 Questions conversations. For more information, go to my 5 Questions page.

5 questions

fiveThere is never enough time. There is never enough space. There is never the right time to ask the kinds of questions I would like to ask. We are always on our way somewhere else. Whether we chat on twitter or facebook, by email or by telephone, by a trip to the keyboard or to the office down the hall, we don’t get to ask the interesting questions. We have to talk about what is next or how to fix this problem or what will happen when that doesn’t work.

I have a lot of great people I know. Some of them have been around me for decades. They know what I sound like when I talk without the aid of asychronicity, and I know where they live. Others have voices I have never heard, faces I have never seen. But I like to talk with them, to say “hi” at least. And I wonder what it would be like to sit with a cup of coffee and time and ask the kinds of questions that interviewers ask. Not cold, embarrassing, entrapping questions, but the kind of questions that invite reflection.

So I decided to do just that.

A few months ago, I had that kind of conversation with my friend Chris about a book he and Julien Smith were writing. I asked five questions, he answered, I clarified a point or two with him, and I published it. Then I tried it again with my friend Diana Scimone to help her with her tweethon to raise $81,000 in one day.

And then, I decided to start asking people who don’t have a campaign or a book.

There is nothing magic about the number five. And the questions are different for everyone, because they are different people and I know different things about them. But I love stopping and thinking about the person and giving them space to think and write about what they may not otherwise be asked.

I’ll start tomorrow. I’ve already got several “5 Question” conversations done. I’ll keep doing them (so don’t think, “Jon must not think I’m very interesting.”) I’m still looking for my own voice in these conversations.

Today, go back and read about Diana’s project and give the cost of three Happy Meals to keep kids from being sold as sex slaves.


Photo by Joanna Young, used by creative commons