Why Entrepreneurs Make Good Product Managers

What makes a good product manager? I once asked this question to a number of product executives. Several of them gave me an answer like this:

A good product manager thinks like a CEO.

What does this mean?

It means you know all aspects of the product – its market, its customers, its operations, its team of talent, etc. You know your product’s and your team’s strengths & weaknesses. You know the market’s current state, potential trends, major players, economic factors, regulatory issues, etc. You know your customers and how they currently solve the problem you are trying to solve.

It means you care about the product deeply. It’s not just a job. It’s a calling, a passion. You have a strong, compelling vision and are willing to work hard to make it happen. And you know how to inspire others with your vision as well.

It means you are pragmatic because this is your livelihood. You are constantly gathering & analyzing data to make your decisions. And when you don’t have enough information – which you rarely will – you are willing to make an informed, yet bold decision.

It means you find people smarter than you and spend a lot of time rallying them. They are the lifeblood of your product and the means to bring flesh to the vision, and you know it. Roadblocks in their path are demolished feverishly & quickly.

It means you are flexible. The world is constantly changing. Your product and your team will need to change with it. Mistakes are embraced and learnings and shared enthusiastically. You’d rather move quickly and course-correct often with your eyes open, than to pick a single direction and go forward blindly.

Product manager, CEO, entrepreneur, business owner – in the end, they all share the same basic mindset. They are trying to build a product that people will love, use, and tell their friends about.

Photo by: Joi

Business Scalability

Scales I’m obsessed with scaling.

Not in the technical, keep-the-Fail-Whale-away sense. In the business sense.

Every time I work on a particular business issue, I can’t help but think: “How can I scale this process?” What can I do to increase efficiency, to produce more with less effort?

This is, of course, rooted in laziness. As Carl Stoddard said: “If necessity is the mother of invention, then laziness must be its father.”

Have you thought about how you can be more lazy with your business? About how you can make your business operations more efficient?

Thinking About Scalability in a Service Business

To get you thinking about business scalability, here are some processes we’ve set into place for our web development agency, WebMocha. A service business like ours is different from a product business, so keep those differences in mind if your business is of the latter type.

Scaling Resources

Revenue potential in a service business is tied directly to your resource capacity. The more talent you have, the more client projects you can take.

However, resources are finite. So how can you scale your resources?

By increasing their productivity. This can be done through training & mentoring, providing them with efficient frameworks & methodologies, automating repetitive tasks, and removing roadblocks from their paths. Doing this well requires careful examination of their workflow, since a well-intentioned but unenlightened process addition can sometimes hurt more than help.

This is why service companies that have been around for years tend to be better than newer shops. Assuming they’ve been actively scaling their business, they’ve had more time to study and improve their methodologies. The result is more value for their company and their customers.

Scaling Clients

Another revenue driver of a service business is the number of client projects you can get. The more paid projects you have, the more revenue you are making.

However, finding customers is difficult. So how can you scale your clients?

By increasing the number of projects you get from existing clients. Since customer acquisition costs are high, if you can encourage current & previous customers to pay for your services again, you’ve skirted those acquisition costs. This requires providing high-quality work, personalized attention, thoughtful follow-up, going above & beyond, and an attitude of “we’re all on the same team” as opposed to “us vs them.”

Another way to scale your clients is to streamline the customer acquisition process. This requires exploring various channels and analyzing which offer the most efficient conversions. For some companies, it’s SEM. For others, SEO. Yet others, social media. For us, it’s the use of brand champions and word-of-mouth marketing. An analysis of our channels has taught us to focus on what works best. The other channels are de-emphasized: we do a little SEO and social media marketing, but no SEM at all.

What Can You Do?

Look at your business processes. Your resources, customer acquisition process, marketing tactics, inventory, distribution channels, etc. If you have the data, examine each one to see where you can be more efficient. If you don’t, instrument your processes to get some data. Or interview your employees to get some qualitative information.

Then you’ll need to think creatively. The answer isn’t always obvious. Talk to a mentor if you have one. Post a question on LinkedIn Answers or Bright Journey if you want outside help. Or even better, talk to your employees. The people doing the actual work will often have lots of good ideas. After all, this will be making their lives easier.

Then you can sit back and revel in your laziness.

Photo by: ~Brenda-Starr~

Creating Rock Stars

Circus at the Taste of Chicago You know what’s better than hiring rock stars? Creating your own.

This entry is the third entry of a three-part series on rock stars.

The Rock Star Series

Creating rock stars is definitely possible. And cheaper. Also, internally-grown rock stars tend to be more loyal than those from the outside, since they appreciate the investment you’ve made in their careers. Hiring outsiders can cause dissatisfaction amongst the current staff too. In short, it is much better to grow your own rock stars than to hire them.

Once you know how to do this, you can replicate the formula throughout your organization. So instead of giving you fish, now I’m going to teach you how to fish.

Hire individuals with potential
There are several elements hiring managers typically seek: current skills, relevant work experience, personality fit, and innate talents. When hiring individuals with the potential to become rock stars, emphasize innate talents & personality fit and deemphasize current skills & relevant work experience. A talent is an aptitude with which an individual is born. Look for a talent that is relevant to your role. The right personality fit includes not only a cultural team fit, but an eagerness & ability to learn, a comfortability with making mistakes, a passion for the work, a strong sense of integrity, and the inclination to be proactive and take initiative. Skills & experience can be gained later. Note that there’s a slight bias towards younger employees here, but I’ve always been a believer that you can teach an old dog new tricks.
Identify good teachers and mentors
Good teachers and mentors are hard to find, perhaps just as hard as finding rock stars. Also, rock stars don’t necessarily make good teachers, and vice versa. A good teacher is someone who can break down the fundamentals in a meaningful & digestible way, apply those concepts into actionable & real-world situations, and understand each student well enough to educate them in their particular learning styles. Teachers should also have enough subject competency that the students respect their knowledge. If such individuals don’t exist, ask for volunteers amongst your rock stars and send them to training on how to be effective mentors. Self-motivated individuals make the best mentors.
Offer lots of training opportunities
If you don’t have good teachers on staff, seek out group training opportunities outside of your organization. Not all workshops & seminars are created equal, so it will take some effort to find the good ones. The effort will be worth it though. Workshops & seminars aren’t the only options. In the software development world, paired programming, code reviews, and project post mortems can also be extremely helpful. One more tip: asking someone to hold a workshop can also be an effective training tool for that person. Sometimes, the best way to learn something is to teach it to someone else.
Set up a mentorship program
While you seek out group training opportunities, establish a mentorship program with your willing & able mentors. Personally, I think formal mentorship programs aren’t organic enough to grow rock stars. They do a fair job transferring skills, but don’t imbue apprentices with rock star habits and mental models. For that, you need something with deeper involvement. Proximity, exposure, and having someone officially in the role of the mentor is important. In the software development world, paired programming can do this, as can shadowing and being placed on the same projects. Mentors & apprentices should have some kind of regular dialogue, though I’m undecided about the effectiveness of structured lesson plans and goals. Feedback from both parties is essential, however, so the mentoring relationship can grow.
Cultivate a culture of learning
Your apprentices need time to learn the right chords and practice their arpeggios before they can become full-fledged rock stars. This requires an environment that encourages education, such as tolerating mistakes, celebrating achievements, sharing lessons learned, and solving problems collaboratively. Learning is and should be fun; if your fledglings are enjoying their apprenticeships, they’ll become masters very soon. Books like The Fifth Discipline can also offer more tips from an organizational standpoint.

How do you create rock stars in your organization?

The Rock Star Series

How to Manage Rock Stars

Musicians at Gordon & Mona's Wedding Now that you’ve hired a rock star, what do you do? After writing about the recruiting process for rock stars, I decided to expand to a three-part series. This is the second topic on my series about rock stars.

The Rock Star Series:

Contrary to popular belief, dealing with rock stars isn’t necessarily easier than poor performers, and certainly not easier than average performers. In order to keep your rock stars productive, on your team, and still jamming out hits, you’ve got to manage them differently.

A quick word about my management style. I use what I call a talent-driven management style, adopted from books like First, Break All the Rules & Now, Discover Your Strengths, the latest management research, and my own experiences as a people manager. My techniques are biased to my particular style and may not work in all situations, though they’ve worked well for me.

Rock stars need to be managed differently
Despite what you might think, you shouldn’t manage everyone on your team in the same way, just like you shouldn’t raise all of your kids in the same way. Every individual is unique, with different motivations, working styles, and temperaments. So really, this tip is good for everyone on your team, not just the rock stars.
Rock stars need effective work environments
Those who were rock stars at previous companies may have reached that status because of the environment there. Try to replicate as much of that environment as you reasonably can, while giving them opportunities to learn how to best work in your environment.
Rock stars need interesting & challenging work
A large reason why rock stars are rock stars is because they thrive on challenging work they care about. Align them with work that matches their personal passions. Make sure you give them a steady stream of such work to keep them motivated. Grunt work may be inevitable, but be aware that rock stars are more apt to leave if they become bored because there are so many opportunities for them elsewhere.
Rock stars need to be monitored closely
You don’t want to lose any of your employees, but you especially don’t want to lose your rock stars. Check on them every so often, both from a workload standpoint and a personal standpoint. See how they’re doing and how they’re feeling. It does mean more work from you, but if they are happy with their jobs, they’ll remain productive. However, be careful not to hover over or micromanage them.
Rock stars can be used to train others
With all that knowledge & skill in their heads, why not try to spread it around? If they are willing and able to, ask your rock stars to hold workshops and seminars for the rest of your team. Knowledge sharing can be very powerful, both in building relationships, providing recognition, and increasing the productivity of others.
Rock stars need to be recognized
Most people enjoy recognition as a reward, and rock stars are no different. Asking them to hold training sessions is one way to recognize their expertise. Giving them positions of authority is another, such as team lead, planner & architect, project evangelist, etc. Awards and monetary compensation are other good methods.
Rock stars need to be inspired
Since they have so many employment options, if they are not doing something that they are passionate about, don’t feel a genuine concern for their welfare, and are not being rewarded appropriately, they will leave. You need to give them a reason to be loyal and inspire them to stay. If you can do that, you’ll have a rock solid team.

How do you manage your rock stars?

The Rock Star Series:

How to Hire Rock Stars

I’m sure you want them. Rock stars, I mean. Whether you’re a start-up or a large corporation, you need the cream of the crop on your team. So how to you find & hire these elusive stars?

I don’t mean to brag, but…

While I was an engineering manager at Yahoo! (YHOO), I was constantly involved in recruiting activities. I did it before I was formally a manager, I did it as a hiring manager, and I did it to help other teams. I quickly realized that I had a strong fascination for the art of recruiting. Who knows, maybe I was a recruiter in a previous life.

During that time, the developers I hired won Superstar awards (an internal award given to only a select few every year) and became managers, directors, & architects. Some even went on to form start-ups.

I devoted a lot of time studying the process, and art, of recruiting. So I think I have a fair bit of knowledge about how to hire rock stars. Looks at fingernails, rubs them on shirt. Ahem.

UPDATED 5/5/2010: I’ve turned this entry into the first part of a series.

The Rock Star Series:

So how does one find and recruit rock stars? Here’s how.

Rock stars usually hang out with other rock stars
This is no secret. Like-minded people tend to associate with each other. That’s why employee referrals are so powerful. But when referrals aren’t bringing in enough candidates, look at where your rock stars spend their time. If you’re hiring software developers, do your rock stars frequent particular forums, mailing lists or open source projects? Check them out for more potential rock stars.
Rock stars aren’t always the best judge of rock star quality
In direct contradiction to the previous tip, sometimes rock stars aren’t able to reliably tell you if other developers are true rock stars too. This isn’t always the case, but on occasion, likability usurps actual abilities. I’ve known a few stars who’ve highly recommended their friends, only to find that their friends aren’t that great.
Rock stars may have particular personality patterns
Get into the heads of your current rock stars. Interview them to understand their temperaments, core values, points of view, motivations, backgrounds, etc. Look for broad patterns. These findings can be a template from which to do your candidate evaluations. But be careful not to follow such patterns strictly. For instance, the rock star developers I hired tended to have strong analytical dispositions, yet have artistic hobbies. Many were also introverts, though I didn’t make that a pattern to follow, because I’ve hired extrovert rock stars as well.
Rock stars already have jobs
You’ll rarely find a rock star posting a resume on Craigslist or some job board. Rock stars are almost constantly employed. So you’ll have to find a way to woo them from their jobs, which isn’t easy – especially if the rock star is loyal and excited about the current position.
Rock stars need to be wooed by other rock stars
If you are a recruiter or middle manager, you’ll have a hard time attracting rock stars from their current jobs. What you need is a rock star from your team who can speak the same language as the candidate. Rock stars need to be impressed by someone they respect. Exceptions exist, of course. Well-known industry visionaries can have a lot of clout over candidates of any background.
Rock stars can be expensive
This isn’t always the case, but the law of supply and demand, coupled with small social networks within industries, means rock stars may constantly be getting offers. Be prepared to pay them well enough so competing offers don’t lure them away. Money isn’t and shouldn’t be the main reason they are coming to work with you, but you’ll need to compensate them competitively.
Rock stars need to feel passionate about their work
Some of the best rock stars I know really care about their discipline. That’s why they are rock stars. More than money or stock options is the promise your company offers. It has to match their passions on some level. Learn about the candidates, read their blogs, and find out what motivates them. If you’re trying to attract a social media rock star to your internal banking product, for instance, then you may want to spend your resources elsewhere.
Rock stars are the sum of their talents & their environments
It’s true. Rock stars are so good at their jobs not just because they are talented, but because they’ve optimized their workflows for their current work environments. If you’re lucky enough to attract a rock star, don’t expect them to hit the ground running. You’ll need to work hard to set up a similar environment and be patient while they learn about your company, your people, and your processes. Do this while you’re waiting for the paperwork and background checks to be completed.
Rock stars need to be hired right away
So you’ve found a rock star who’s willing to come work with you. What are you waiting for? Cut through whatever red tape is in your way and get the star into your office now! Start-ups will have an advantage over large corporations here, though if you know the right people, it’s possible to get the star into your corporation quickly.

What have you done to hire rock stars?

The Rock Star Series:

Ten Great Interview Questions

There is an art to interviewing employee candidates.

You have a limited amount of time to ask maximally effective questions. The right questions should give you an accurate-enough impression of the candidate and how he/she will perform at your company.

If you are of the Microsoft (MSFT) or Google (GOOG) mindset, then you probably favor puzzles and creative problem solving questions. Those are great and have their place.

Here are ten more great interview questions that seek to gain a better impression of the candidate.

  1. How do you personally define and measure success?This is a two-part question. The first part aims to discover the candidate’s motivations and aspirations. The second part judges the candidate’s ability to realistically determine if and when those goals are reached. Most people have some idea of success, but haven’t defined ways to measure it. If that’s the case for this candidate, being able to come up with an impromptu answer can demonstrate quick-thinking and analytical ability.
  2. What are you doing to improve yourself, physically, mentally, or spiritually?This question assesses the candidate’s desire and past actions toward self-improvement. A candidate who has actively sought self-improvement will be able to answer quickly. A candidate who has not may hesitate and try to make up something on the spot.
  3. What were your expectations when you began working in your last job?This question discerns whether or not the candidate had realistic expectations of their last role. If the candidate’s expectations did not match the previous position, you can delve deeper to find out why and what the candidate did to rectify the situation. The answer may demonstrate how the candidate solves role-oriented problems.
  4. In what kind of work environment do you do your best work?This question determines in which work environments the candidate will thrive. Hopefully your company’s environment matches the candidate’s preferences, otherwise there may be a mismatch. A preference doesn’t mean the candidate will necessarily perform poorly, but he/she may not operate at an optimal capacity.
  5. How do you alleviate stress?This question seeks out the candidate’s coping mechanisms for the inevitable stress and frustrations that come with any job. The answer should include realistic & positive activities or outlets.
  6. What tools or habits do you use to keep organized?This question looks at previous behavior as a determinant of future behavior, specifically, in the candidate’s organizational prowess. Everyone says they are organized, so hopefully the candidate can prove it by discussing specific tools and habits.
  7. When I call your previous employer and references, what are they likely to tell me?This question examines the accuracy of the candidate’s self-awareness. It can be surprising how many people choose references that may speak poorly of them, or perceive themselves differently than how others perceive them.
  8. If you were hired for this position, what would you do in your first week here?This question gives you an idea of how much a self-starter this candidate is, and whether or not this candidate understands the role well enough to get started quickly. Although this question is more suited for experienced candidates than recent college graduates, it can test the creativity of a recent graduate as well.
  9. How would you react if I told you your interview has been terrible so far?This is a bit of a trick question designed to see how a candidate will react on his/her feet when startled and disappointed. If the interview is indeed going well, you can follow up with some reassurances. If not, then, well…
  10. Ask a question that may trigger the candidate to say, “We can’t do that.”You will have to be a bit creative here with the question you select. The goal is to assess the candidate’s creative problem solving skills. A poor answer is how your particular request is not possible. A good answer is, “Here’s what we can do instead.” The candidate should offer viable alternatives and be able to discuss trade-offs.

Some of these questions come from Becky Regan, an HR consultant mentioned in the Entrepreneur magazine article 6 Weeks to a Better Bottom Line and Nick’s Pizza & Pub from the Inc. Magazine article Lessons From a Blue-Collar Millionaire.

Do you have any other great interview questions?

Comic from: Dilbert

Reading True North: Knowing Your Authentic Self Exercise

How well do you know yourself? The fourth chapter of True North: Discover Your Authentic Leadership strives to help develop self-awareness by assessing your leadership strengths, shortcomings, and development needs.

The True North exercises:

Basic Self-Awareness Assessment:

The following questions compare how others view me with my own perception. I asked several friends & colleagues to rate me. Below, my self-rating is provided, followed by the averaged score from the others. A 10 is a “very,” 5 is a “moderately,” and 1 is a “barely.”

Question Self-Rating Feedback Rating
How self-confident are you? 8 8.5
How aware are you of your moods and emotions? 9 9
How effective are you in regulating your moods to minimize their impact on other people? 8 9
When confronted with situations that are displeasing to you, how well do you take the time to think clearly about them before responding or reacting? 8 8.25
When you receive critical feedback from others, how well are you able to take in the feedback and respond in a constructive manner without acting defensively? 7 9.25
How well do you understand the emotional makeup of others and their needs? 9 9.25
How sensitive are you in relating to others’ needs and helping them? 8 9.25
How skillful are you in building lasting relationships? 7 9.5
How well do you network with others and create networks of people with common interests? 8 9
How effective are you in leading teams? 8 8.75
Do others follow your lead voluntarily? 9 9
How persuasive are you in convincing others of your mutual interests? 8 8.5

After reviewing the feedback, to what extent do you see yourself as others see you? How strong is your basic self-awareness right now?

I honestly thought I was being a little cocky with my self-assessment. Instead, it seems I am a little hard on myself. Just a little. To be cocky again, I would say my self-awareness is pretty darn good right now.

Strengths and Development Areas

What are your strongest capabilities or talents?

One of my strongest capabilities lies in an empathic nature that enables me to connect with others.

Way back in fifth grade, my teacher told me, “Never judge a person until you’ve walked a mile in his shoes.” That maxim stuck with me, permeating my everyday thoughts and interpersonal encounters. Every time I engage in a discussion or debate, I put myself into the other person’s shoes to understand his/her point of view.

Oddly enough, this happens so much that I sometimes find it difficult to be righteously indignant with people if I can understand why they’re being insulting or arrogant, even if I feel like I should be righteously indignant with them. Go figure.

Other capabilities and talents I consider as strengths are an analytical temperament, the ability to think critically, the comfort of making mistakes and learning from them, and the desire to constantly set and strive for long-term goals.

What are your strongest attributes as a leader?

As a leader, my empathic nature allows me to build strong relationships and inspire others. I know I’m not an expert in every field I want to be an expert in, so I’m thankful for the brillant friends I’ve made.

There’s this anecdote about Henry Ford that I like. During an interview, he told a reporter to ask him any question he wanted about his business’ operations. So the reporter asked for an obscure detail, like how many nuts and bolts go into a Model T. Ford then picked up his phone, called one of his lead engineers, and and gave the reporter the answer.

Ford’s effectiveness as a leader was not that he knew everything there was to know about his business’ operations. It was the relationships he made, the people who worked with him, and his social network. I aspire for the same kind of effectiveness.

What are your greatest needs for development as a leader?

There are situations where I am nervous and out of my element. Public speaking, approaching investors, talking to the media, and similar situations can be nerve-wracking. I’m sure I’m not alone in these. But as a leader, these are necessary skills to learn.

Toastmasters was one solution I used to use. Once my schedule clears up, I plan on finding a local chapter and continuing. The best way to approach investors, in my opinion, is to not need them, bootstrap, and build a great business. Then they’ll come to us. As for speaking to the media, well, perhaps I’ll attend a media training workshop when the time comes.


Do you need structure in your job? To what extent are you comfortable with ambiguity and change?

I love ambiguity & change, personally. Too much structure & routine bore me. My attention span at any particular role is about one year. After that, I tend to need drastic change. Before joining Yahoo! (YHOO), I stayed at companies for approximately one year. While at Yahoo, I was lucky enough to change roles & responsibilities significantly enough to keep myself engaged. My career there progressed this way: web developer -> technical manager of a small team -> technical manager of first-line managers and a larger team -> senior product manager. Each role was on a new property with a new team; each was different enough that I was always challenged. That’s the way I like it.

What level of financial security will allow you to feel comfortable?

I know how to live within my means. It is a cross between bare necessities and a handful of luxuries. To be honest, I’m fairly comfortable right now, though I will be getting married and starting a family soon, so my financial needs will be increasing.

To what extent do you need to be leading a team?

That’s a good question. I never thought about it as a need. But I sure enjoy being a leader in some way. If I won the lottery and never needed to work again, I would still start a business or non-profit venture. So perhaps I do have a need to lead.

How much time do you need with your family or loved ones each week?

Family comes first, always. I need as much time as they need me. Way back in college, I planned on entering this industry because of the ability to work from home. That meant being able to take my kids to softball games & guitar lessons, spend time with my wife, and take care of my parents if & when they need me to.

How much personal time do you need each week to recharge?

Perhaps a few hours a day. I’m not a morning person, so the first couple of hours in the morning are generally spent slowly charging up and getting ready for the day. Then at night, I like to unwind with my family or a good book. Writing also serves as a way to recharge.

Your Authentic Self

What are your vulnerabilities, blind spots, and shadow sides?

I certainly have some pet peeves. I’m impatient with impatience. I’m close-minded about close-minded people. And people who speak in absolutes absolutely bug me.

I know, I just wrote that I’m empathic and can walk in other peoples’ shoes. But I have my limits, especially if someone’s ignorance, arrogance, or obnoxiousness is directed toward someone I care about. If it is aimed at me, that’s fine. I can take it. I can even take criticism; I’m far from perfect and I know it. But leave my loved ones alone.

Admittedly, my memory isn’t as sharp anymore. To compensate, I’ve gotten into the habit of relying on digital solutions to extend my memory. This means using Google Calendar (GOOG) to manage my schedule, Gmail to manage my tasks, and my Apple iPhone (AAPL) to give me access to those tools wherever I am. It’s an efficient system, though I really need to do some brain teasers & memory games so I’m not a total moron when I’m a grandfather.

To what extent do you use defensive armor as a shield to protect yourself from exposing your vulnerabilities with others?

Everyone has defense mechanisms to protect their vulnerabilities to some extent, that’s only natural. I am a fiercely private person, if you can believe it. There are aspects of my life I will never share online, especially if they pertain to my family. But everything else is filtered appropriately. Even my online presence is part of my privacy strategy – if I can control what appears online (my personal brand, so to speak), then I can control what is seen and what is hidden. The genericness of my name also helps with the hidden part.

Back to vulnerabilities. This could be the New Yorker in me, but I’m laced with what I consider a healthy level of trust (or lack thereof) for complete strangers. I don’t share my vulnerabilities with a stranger, nor do I believe they are out to screw me over. As I get to know someone, my trust & comfort level with them increases; inversely, my defensive armor decreases. But to a point. To see any more of my vulnerabilities means you need to get into my inner circle of family, friends, and colleagues.

At the same time, I believe most people strive to be good and not overtly malicious, though we are all born selfish. I give most people the benefit of the doubt. So I share my thoughts, lessons learned, and whatever advice I’ve picked up with complete strangers. It’s my small effort in perhaps helping one other person in this huge world of ours. To the extent where I can share a vulnerability and connect with that person safely and without consequence to me or my family, I will do it.

How can you become more comfortable in sharing your vulnerabilities with others?

I am comfortable with my vulnerability sharing levels at the moment. I don’t think it serves any good to pour my heart out to a prospective client, for example. Nor should I hold all of my frustrations in. Everyone needs an outlet. I have mine, which include my inner circle. My circle of trust, where I keep nothing from you, you keep nothing from me, and round and round we go.

How comfortable are you with who you are right now?

I am very comfortable with who I am. I am an idealistic realist; I am content with my life, but not satisfied. This means I’m unsatisfied enough to strive for more. At the same time, I’m content, happy, and very grateful for the life I have and the decisions I’ve made. And I look forward to the future eagerly.

How would you answer these questions?

The True North exercises:

Reading True North: Your Greatest Crucible Exercise

What is your greatest crucible? The third chapter of True North: Discover Your Authentic Leadership explores the experiences that involved the greatest pressure, stress, and adversity in one’s life. Here is the exercise that follows that chapter.

The True North exercises:

  • Introduction Exercise
  • Chapter 1: Your Story Exercise
  • Chapter 2: Losing Your Way Exercise
  • Chapter 3: Your Greatest Crucible Exercise
  • Chapter 4: Knowing Your Authentic Self Exercise
  • Chapter 5: Practicing Your Values and Principles Exercise
  • Chapter 6: Your Motivations and Motivated Capabilities Exercise
  • Chapter 7: Building Your Support Team Exercise
  • Chapter 8: The Integrated Leader Exercise
  • Chapter 9: The Purpose of My Leadership Exercise
  • Chapter 10: Empowering Other Leaders Exercise
  • Chapter 11: Honing Your Leadership Effectiveness Exercise

Write freely about your greatest crucible and describe it in the following ways:

  • How did you feel at the time?
  • What resources did you call upon?
  • How did you resolve the issues, if you have?
  • How did it shape you and your views about the world?

It’s tough to choose just one experience as my greatest crucible. There have been many difficult experiences that altered my life. Here is one that comes to mind.

Back at Yahoo! (YHOO), I was given the honor of managing a large group of talented web developers. However, the team grew quite large, larger than my experience could handle at that time.

In one incident, a few members of my team helped launch a redesign of a major Yahoo! property. Unfortunately, this redesign was plagued with some troublesome bugs, a few of which were my team’s responsibility. Those few, unfortunately, were high-profile showstoppers and took a long time to fix. Too long. Soon, the bugs caught the attention of a VP, who sat me down to talk.

I still remember sitting there with a huge knot in my throat, trying to explain how the errors occurred. Fortunately, my team finally fixed them. But the VP did not see this as a sufficient solution. He saw a break in communications and our organizational structure that exacerbated the problem more than it should have been.

I also remember saying the words, “This is ultimately my responsibility and I take the blame. I will continue working with our teams to come up with a better solution.” And I think I might have even uttered the words, “I fucked up” in there too.

My face was red and hot. I thought that was the end of my career at Yahoo!. I imagined getting a call from HR and being shown the door. Part of the problem was that I didn’t catch this issue sooner, and I didn’t do that because I was overwhelmed by a large team. I knew that, and so did the VP.

Eventually, a long-term solution was implemented. There was a reorganization of my department. The incident wasn’t solely in my team, it was endemic to my department and the nature of our relationship to other teams at the company. While the reorg was a bummer to many, and resulted in a smaller, more focused team for me, it made sense from an organizational standpoint.

The VP didn’t blacklist me or have me fired. The incident taught me to be cognizant of my strengths and weaknesses, to balance my stretch goals with my abilities, and to think holistically from an organizational standpoint. As a crucible, it was damn tough – it was one I will never forget.

Describe any relationships, such as those with mentors, that had a transformative effect on you and your leadership. What did you learn from that relationship and how did it shape who you are?

I’ve never had a formal mentor, though I’ve always wanted one. In lieu of that, I’ve always looked at people that inspired me and emulated their effective traits.

Throughout my career, I’ve been lucky to have lots of great managers. Each excelled in some way. One is a technical genius with fantastic foresight into the high-tech industry, another is relentlessly customer-focused and data-driven, and another knew how to play the game of office politics well (I wish this knowledge wasn’t necessary or useful, but in large corporations, it sadly is).

Each has enhanced my world view and repetiore of skills. I can’t say I replicate them as well as these managers do, but I strive to. Each also challenged me, both directly and indirectly, to stretch past my comfort zones and evolve my skills. For that, I am eternally indebted to these inspiring individuals.

Describe any other experiences that triggered significant leadership development.

I’m guessing this question is seeking more crucible-like experiences, so let me this other incident:

While serving as the president of a cultural community service club in college, I was responsible for a street carnival. Unfortunately, I overslept that day. Since I’ve already written about it, I won’t go over all of the details. But it was definitely a harsh learning opportunity.

All in all, I would say I’ve had a lucky life. Now that I’ve formally started a profitable business of my own, I expect to face more crucibles. And I look forward to them.

In looking back on those experiences, what did you learn from them?

The debacle in college taught me to delegate properly, have faith in my delegates, and to make sure I get a good night’s rest before a big event.

In what ways have they helped you to grow?

They’ve all stretched me and taught me management skills. Be aware of the whole situation. Understand our dependencies and consequences. And like the Boy Scouts, Be Prepared.

How can you use these experiences to reframe your life story and to understand yourself and your life more fully? Are there ways in which these experiences are holding you back today?

One pattern I’ve noticed in my life is the constant push outside my comfort zones. I am and have always been an ambitious and demanding person. I always strive for personal success and demand a lot out of myself. Because of this, I frequently push myself outside my comfort – and ability – zones.

So when I fall far outside of my abilities, the consequences can have quite an impact.

Don’t get me wrong. Mistakes are good. Mistakes are fantastic learning opportunities. I celebrate a culture that allows experimentation, self-improvement, and forgiveness of mistakes.

However, there’s a practical limit to how disastrous a mistake can be. If it kills your organization, lands you in a lawsuit, and ends your marriage, that’s not a good kind of mistake. So as I continue to push myself, I will need to be mindful of my abilities’ limits.

Transformation from “I” to “We.”

Are you on “the hero’s journey”? Do you ever see yourself as the hero of your own journey?

I’ve always felt myself on a journey. The destination is surprisingly clear too, though I know I have to work hard for it – to be a good father and husband, to be an entrepreneur and business owner, to enact some kind of long-lasting beneficial change to my society and environment, and to leave a legacy.

However, I wouldn’t use the label “hero” for myself. That’s a little much. I see myself more as a catalyst that enables others to help make the vision a reality.

Though, I’d sure love to be a hero to my kids one day.

Have you made the transformation from “I” to “We”? If so, what triggered this transformation for you?

I like to think I have. In Stephen Covey’s book “The 7 Habits of Highly Effective People“, he describes three sequential phases of growth:

  1. Dependence – We all start life being dependent on someone else, like our parents. Some remain at this level their whole lives.
  2. Independence – Many strive for this level. For some, this means self-reliance. For others, it means being a loner.
  3. Interdependence – Few reach this level. This is when you realize and behave as if the sum of two or more people (such as a spouse, teammates, etc) is greater than the parts.

While being a manager, I learned the power of interdependence. That may seem odd, since one view of a manager is as an autocratic entity working alone to control others. But that’s not always so. My management philosophy means working closely with my team and, in many ways, letting them lead the way with me in a supporting role – a catalyst for their ideas.

If you have not yet made this transformation, what would have to happen in your life and leadership for a transformation like this to occur?

I would say I’ve made that transformation already.

How would you answer these questions?

The True North exercises:

  • Introduction Exercise
  • Chapter 1: Your Story Exercise
  • Chapter 2: Losing Your Way Exercise
  • Chapter 3: Your Greatest Crucible Exercise
  • Chapter 4: Knowing Your Authentic Self Exercise
  • Chapter 5: Practicing Your Values and Principles Exercise
  • Chapter 6: Your Motivations and Motivated Capabilities Exercise
  • Chapter 7: Building Your Support Team Exercise
  • Chapter 8: The Integrated Leader Exercise
  • Chapter 9: The Purpose of My Leadership Exercise
  • Chapter 10: Empowering Other Leaders Exercise
  • Chapter 11: Honing Your Leadership Effectiveness Exercise