How Creative Do You Have to Be?

To follow up on last week’s post about the two types of entrepreneurs, I hear from people all the time that they can’t be an entrepreneur because they’re not creative.  I used to say that myself, but Mariquita reminds me periodically that that’s nonsense…and as a case in point, I didn’t have the original idea that gave birth to Return Path James Marciano did.  And I didn’t have the original idea to create a deliverability business, George Bilbrey did.  Or an inbox organizer consumer application, Josh Baer did.

But I still consider myself an entrepreneur as the founder and leader of the company, as it takes a lot of creativity and business building acumen to get from an idea to a business, or from a small business to a big business.

Sure, you can invent something from scratch.  Someone created the first car.  The first computer.  The first telephone.  Harnessed the power of electricity for home/commercial use.  The first deliverability service or inbox organizer.  George and others will say you can create a process for this…but I think it’s a bit like lightening striking.

But sometimes the best ideas are ones that are borrowed from others or combined from other sets of existing things.  There’s nothing wrong with that!  And you can do this without stealing intellectual property.  For example, I took a ton of business trips my first few years out of college with a heavy duffel bag that caused a pinched nerve in my shoulder.  Then someone decided to put wheels, a relatively old and stable technology, on suitcases about 15 years ago.  Hallelujah.

Regardless of what type of entrepreneur you are, you can exercise business creativity in lots of different ways, not just by inventing a new product.

UPDATE:  This week’s Economist has an interesting article that fits right into this discussion.  It’s called In Praise of Misfits, and its telling subtitle is something like “Why business needs people with dyslexia, ADD, and Asperger’s.”  A great read on this theme.

What Kind of Entrepreneur Are You?

I think there are two kinds of entrepreneurs, and sometimes, you can be both.  There is the kind that starts businesses, and there is the kind that builds businesses.

The kind of entrepreneur who starts businesses but usually doesn’t like running or building them are typically serial entrepreneurs.  How can you spot one?  They:

• Have an idea a minute and a bit of ADD – they are attracted to bright shiny objects – they can’t focus
  • Would rather generate 1 good and idea and 19 bad ones than just 1 good one
  • Are always thinking about the next thing, only excited by the possibility of what could be, not by what is
  • Are more philosophical and theoretical than practical
  • Probably shouldn’t run businesses for more than a few months
  • Are likely to frustrate everyone around them and get bored themselves
  • Are really fun at cocktail parties
  • Say things like “I thought of auctions online way before eBay!”

The second kind of entrepreneur is the kind of person who can run businesses but may or may not come up with the idea.  Typically, these people:

• Care about success, not about having the idea
• Love to make things work
• Would rather generate 1 idea and execute it well than 2 ideas
• Are problem solvers
• Are great with people
• May be less fun at cocktail parties, but you’d want them on your team in a game of paintball or laser tag

It’s the rare one who can do both of these things well.  But you know them when you see them.  Think Dell or Microsoft…or even Apple in a roundabout way if you consider the fact that Jobs hired Cook (and others) to partner with them to run the business.

Book Short:  Internet True Crime

Fatal System Error: The Hunt for the New Crime Lords Who Are Bringing Down the Internet, by Joseph Menn (book, kindle) was a bit of a disappointment.  I was really hoping for more of an explanation of how the “business” of Internet crime works — what the economics are like, what the landscape/scope/sectors are like, who the players are.

What I got was a bit of a true crime novel, the story of Barrett Lyon and Andy Crocker, who are respectively a geek and a cop, and their very specific stories of tracking down a handful of internet criminals around a handful of technical tactics (DDOS attacks and botnets).  It wasn’t bad, the stories were ok and occasionally entertaining, but it was very narrow.

It felt to me like there is a much more interesting story to tell around criminals who USE the Internet to commit crimes as opposed to people attacking the infrastructure.  Has anyone ever run across a book like that?

You Can’t Teach a Cat How to Bark, But You Might be Able to Teach it How to Walk on its Hind Legs

My co-founder George and I have had this saying for a while.  Cats don’t bark.  They can’t.  Never will.  They also don’t usually walk on their hind legs in the wild, but some of them, after some training, could probably be taught to do so.

Working with people on career evolution sometimes follows that same path.  Lots of the time, an employee’s career evolution is natural and goes well.  They’re playing to their strengths, in their sweet spot, progressing along nicely.  But often that’s not the case.  And it goes both ways.  Some employees want something different.  The sales rep wants to be a sales manager.  The product manager wants to try marketing.  Sometimes the organization needs something different out of the person.  Be a stronger manager.  Be more collaborative.  Acquire more domain or functional expertise.

These transitions might or might not be difficult.  It completely depends on the person involved and the competencies required for the new role.  And that’s where the barking cat comes into play.  There’s more art than science here, but as a manager or as the employee, figuring out the gap between existing strengths/experience and the required competencies for the new job, and whether the missing elements *can* be taught or not is the exercise at hand.

I’m not sure there’s a useful rule of thumb here, either.  I had a boss once many years ago who said you can teach smart people how to do anything other than sales.  Another boss said you can teach anyone any fact, but you can’t teach anyone empathy.  Both of these feel too one-size-fits-all for me.  One thing we do at Return Path from time to time is encourage an employee facing some kind of stretch transition (for whatever reason) to participate in or run a short-term side project with a mentor that lets them flex some relevant new muscles.  Essentially we let them try it on for size.

OnlyOnce is 8 years old this week, which is hard to believe. So it is fitting that I got halfway through a new post this morning, then a little alarm bell went off in my head that I had written something similar before.  The topic is around moderation versus extremes.  I first wrote about this topic in 2005 in a post called Shifting Gears but I have thought about it more recently in a different way. 

Instead of phrasing this as a struggle between “Meden Agan,” which is Greek for “everything in moderation,” and “Gor oder gornischt,” which is Yiddish for “all or nothing,” I’d like to focus here on the value of occasionally going to an extreme. And that value is around learning. Let me give three examples:

-We were having a buy vs. build conversation at work a few months back as we were considering an acquisition. Some people in the room had an emotional bias towards buy; others toward build. So we framed the debate this way:  “Would you acquire the company for $1 instead of building the technology?” (Yes!) “Would you buy it for $10mm?” (No!) Taking the conversation to the extremes allowed us to focus on a rational answer as opposed to an emotional one — where is the price where buy and build are in equilibrium?

– With my colleague Andrea, I completed a 5-day juice fast a few weeks back. It was good and interesting on a bunch of levels. But I came away with two really interesting learnings that I only got from being extreme for a few days:  I like fruits and veggies (and veggie juices) a lot and don’t consume enough of them; and I sleep MUCH better at night on a relatively empty stomach

– Last year, I overhauled my “operating system” at work to stop interviewing all candidates for all jobs and stop doing 90-day 1:1 meetings with all new employees as well. I wrote about this in Retail, No Longer. What finally convinced me to do it was something one of my colleagues said to me, which was “Will you be able to keep these activities up when we have 500 employees?” (No) “So what is the difference if you stop now and save time vs. stopping in 6 months?” Thinking about the extreme got me to realize the full spectrum

It may not be great to live at the extremes, but I find extremes to be great places to learn and develop a good sense of what normal or moderate or real is.

I was talking to a CEO the other day who believed it was “wrong” (literally, his word) to meet directly 1:1 with people in the organization who did not report to him.  I’ve heard from other CEOs in the past that they’re casual or informal or sporadic about this practice, but I’ve never heard someone articulate before that they actively stayed away from it.  The CEO in question’s feeling was that these meetings, which I call Skip-Level Meetings, disempowers managers.

I couldn’t disagree more.  I have found Skip-Level Meetings to be an indispensable part of my management and leadership routine and have done them for years.  If your culture is set up such that you as CEO can’t interact directly and regularly with people in your organization other than the 5-8 people who report to you, you are missing out on great opportunities to learn from and have an impact on those around you.

That said, there is an art to doing these meetings right, in ways that don’t disempower people or encourage chaos.  Some of these themes will echo other things I’ve written in recent posts like Moments of Truth and Scaling Me.  My five rules for doing Skip-Level Meetings are:

1. Make them predictable.  Have them on a regular schedule, whatever that is.  The schedule doesn’t have to be uniform across all these meetings.  I have some Skip-Levels that I do monthly, some quarterly, some once a year, some “whenever I am in town.”
   
2. Use a consistent format.  I always have a few questions I ask people in these meetings – things about their key initiatives, their people, their roadblocks, what I can do to help, what their POV is about the company direction and performance, how they are feeling about their role and growth.  I also expect that people will come with questions or topics for me.  If I have more meaty ad hoc topics, I’ll let the person know ahead of time.
   
3. Vary the location.  When I have regular Skip-Levels with a given person, I try to do the occasional one over a meal or drink to make it a little more social.  For remote check-ins, I now always do Skype or Videophone.
   
4. Do groups.  Sometimes group skip-levels are fun and really enlightening, either with a full team, or with a cross-section of skip-levels from other teams.  Watching people relate to each other gives you a really different view into team dynamics.
   
5. Close the loop.  I almost always check-in with the person’s manager BEFORE AND AFTER a Skip-Level.  Before, I ask what the issues are, if there is anything I should push on or ask.  After, I report back on the meeting, especially if there are things the person and I discussed that are out of scope for the person’s job or goals, so there are no surprises.

 I’m sure there are other things I do as well, but I can’t imagine running the company without this practice.  Doing it often and well EMPOWERS people in the company…I’d argue that managers who feel disempowered by it aren’t managers you necessarily want in your business unless you really run a command-and-control shop.

Book Short:  Required Reading, Part II

Every once in a while, a business book nails it from all levels.  Well written, practical, broadly applicable to any size or type of organization, full of good examples, full of practical tables and checklists.   The Leadership Pipeline, which I wrote about here over six years ago, is one of those books — it lays out in great and clear detail a framework for understanding the transition from one level to another in an organization and how work behaviors must change in order for a person to succeed during and on the other side of that transition.  In an organization like Return Path‘s which is rapidly expanding and promoting people regularly, this is critical.  We liked the book so much that we have adopted a lot of its language and have built training courses around it.

The book’s sequel, The Performance Pipeline (book, Kindle), also by Stephen Drotter but without the co-authors of the original book, is now out — and it’s just as fantastic.  The book looks at the same six level types in an organization (Enterprise Manager, Group Manager, Business Manager, Functional Manager, Manager of Managers, Manager of Others, and Self Managers/Individual Contributors) and focuses on what competencies people at each level must have in order to do their jobs at maximum effectiveness — and more important, in order to enable the levels below them to operate in an optimal way.

This book is as close to a handbook as I’ve ever seen for “how to be a CEO” or “how to be a manager.”  Coupled with its prequel, it covers the transition into the role as well as the role itself, so “how to become a CEO and be a great one.”  As with the prequel, the author also takes good care to note how to apply the book to a smaller organization (from the below list, usually the top three levels are combined in the CEO, and often the next two are combined as well).  No synopsis can do justice to this book, but here’s a bit of a sense of what the book is about:

• Enterprise Manager:  role is to Perpetuate the Enterprise and develop an Enterprise-wide strategic framework – what should we look like in 15-20 years, and how will we get the resources we need to get there?
• Group Manager:  role is to manage a portfolio of businesses and develop people to run them
• Business Manager:  role is to optimize short- and long-term profit and develop business-specific strategies around creating customer and stakeholder value
• Functional Manager:  role is to drive competitive advantage and functional excellence
• Manager of Managers:  role is to drive productivity across a multi-year horizon, and focus
• Manager of Others:  role is to enable delivery through motivation, context setting, and talent acquisition
• Self Managers/Individual Contributors:  role is to deliver and to be a good corporate citizen

I could write more, but there’s too much good stuff in this book to make excerpts particularly useful.  The Performance Pipeline is another one of those rare – “run, don’t walk, to buy” books.  Enjoy.  For many of my colleagues at RP – look out – this one is coming!

Jim Collins, in both Good to Great and Built to Last talked about the BHAG – the Big, Hairy Audacious Goal – as one of the drivers of companies to achieve excellence.  Perhaps that’s true, especially if those goals are singular enough and simplified enough for an entire company of 100-1000-10000 employees to rally around.

I have also observed over the years that both star performers and strong leaders drive themselves by setting large goals.  Sometimes they are Hairy or Audacious.  Sometimes they are just Big.  I suppose sometimes they are all three.  Regardless, I think successfully managing to and accomplishing large personal goals is a sign of a person who is driven to be an achiever in life – and probably someone you want on your team, whether as a Board member, advisor, or employee, assuming they meet the qualifications for the role and fit the culture, of course.

I’m not sure what the difference is between Hairy and Audacious.  If someone knows Jim Collins, feel free to ask him to comment on this post.  Let’s assume for the time being they are one and the same.  What’s an example of someone setting a Hairy/Audacious personal goal?  My friend and long-time Board member Brad Feld set out on a quest 9 years ago to run a marathon in each of the 50 states by the age of 50.  Brad is now 9 years in with 29 marathons left to go.  For those of you have never run a marathon (and who are athletic mortals), completing one marathon is a large, great and noteworthy achievement in life.  I’ve done two, and I thought there was a distinct possibility that I was going to die both times, including one I ran with Brad .  But I’ve never felt better in my life than crossing the finish tape those two times.  I’m glad I did them.  I might even have another one or two in me in my lifetime.  But doing 50 of them in 9 years?  That’s a Hairy and Audacious Goal.

For me, I think the Big goal may be more personally useful than the Hairy or Audacious.  The difference between a Big goal and a Hairy/Audacious one?  Hard to say.  Maybe Hairy/Audacious is something you’re not sure you can ever do, where Big is just something that will take a long time to chip away at.  For example, I started a quest about 10-12 years ago to read a ton of American history books, around 50% Presidential biographies, from the beginning of American history chronologically forward to the present.  This year, I am up to post-Civil War history, so roughly Reconstruction/Johnson through Garfield, maybe Arthur.  I read plenty of other stuff, too – business books, fiction, other forms of non-fiction, but this is a quest.  And I love every minute of it.  The topic is great and dovetails with work as a study in leadership.  And it’s slowly but surely making me a hobby-level expert in the topic.  I must be nearing Malcolm Gladwell’s 10,000 hours by now.

The reason someone sets out on a personal quest is unclear to me.  Some people are more goal-driven than others, some just like to Manage by Checklist, others may be ego-driven, some love the challenge.  But I do think that having a personal quest can be helpful to, as Covey would say, Sharpen the Saw, and give yourself something to focus personal time and mental/physical energy on.

Just because someone isn’t on a personal quest doesn’t mean they’re not great, by the way.  And someone who is on a quest could well be a lunatic.  But a personal quest is something that is useful to look for, interesting and worth learning more about if discovered, and potentially a sign that someone is a high achiever.

Alter Ego

A couple people have asked me recently how I work with an Executive Assistant, what value that person provides, and even questioned the value of having that position in the company in an era where almost everything can be done in self-service, lightweight ways. At my old company (in the 90s), each VP-level person and up had a dedicated assistant – the world certainly doesn’t require that level of support any more.  In our case, Andrea has other tasks for the company that take up about half of her time.

I happen to have the absolute best, world class role model assistant in Andrea, who I’ve had the pleasure of working with for almost seven years now (which is a reminder to me that she has a sabbatical coming up soon!).

This is an important topic.  It’s tempting for CEOs of startups, and even companies that are just out of the startup phase, to want to do it all themselves…or feel like they don’t need help on small tasks.  My argument against those viewpoints is that your time is your scarcest resource as the leader of an organization, and anything you can do to create more of it for yourself is worthwhile.  And a good assistant does just that – literally creates time for you by offloading hundreds of small things from your plate that sure, you could do, but now you don’t have to.

I asked Andrea to write up for me a list of the major things she does for me (although she didn’t realize it was going to turn into a blog post at the time).  I’ll add my notes after each bullet point in italics on the value this creates for me.

• Updates and maintains calendar, schedules meetings and greets visitors – My calendar is like a game of sudoku sometimes.  I can and do schedule my own things, but Andrea handles a lot of it.  She also has access to all my staff’s calendars so she can just move things around to optimize for all of us.  Finally, she and I review my calendar carefully, proactively, to make sure I’m spending my time where I want to spend it (see another item below)
• Answers and screens direct phone line – The bigger we get, the more vendors call me. I can’t possibly take another call from a wealth management person or a real estate broker.  Screening is key for this!
• Plans and coordinates company-wide meetings and events – This is an extension of managing my calendar and accessing other executives’ calendars…and a pretty key centralized function.
• Plans and coordinates Executive Committee offsite’s – Same, plus as part of my theme of “act like you’re the host of a big party,” I like this to be planned flawlessly, every detail attended to.  I do a lot of that work with Andrea, but I need a partner to drive it.
• Collects and maintains confidential data – Every assistant I’ve ever had starts by swearing an oath around confidentiality.
• Prepares materials for Board Meetings and Executive Committee meetings – Building Board Books is time consuming and great to be able to offload.  We put together the table of contents, then everyone pours materials into Andrea, and poof!  We have a book.  For staff meetings, she manages the standing agenda, changes to it, and the flow of information and materials so everyone has what they need when they need it to make these meetings productive from start to finish.  In our case, Andrea is part of the Executive Committee and joins all of our meetings so she is completely up to speed on what’s going on in the company – this really enables her to add value to our work.  She’s also not just a passive participant – some great ideas have come from her over the years!
• Coordinates and books travel (domestic and international) – Painful and time consuming, not because Expedia is hard to use but because there is a lot of change, complexity, and tight calendars to manage and coordinate for certain trips.  And while it takes a while to get an assistant up to speed on how you like to travel or how you think about travel, this is a big time saver.
• Prepares expense reports – Same thing – you CAN do it, but easier not to.
• Manages staff gifts and Anniversary presents for all employees – This is a big one for me.  I send every employee an anniversary gift each year and call them.  Once a month, a stack of things to sign magically appears on my desk…and then gets distributed.  Andrea manages the schedule, the inventory of gifts, the distribution of gifts to managers.
• Manages investor database – I assume someday we’ll have a system for this, but for now, IR is a function that Andrea coordinates for me and Jack, my CFO.
• Assist Executive Committee with project as needed – The person in this role for you ends up being really valuable to help anyone on your staff with major projects.  Good use of time.
• Prepares Quarterly Time Analysis for CEO – This is a big one for me.  Every quarter, Andrea downloads my calendar and classifies all of my time, then produces an analysis showing me where I’m spending time my classifications are – Internal, External, non-RP, free, travel, Board/Investor.  This really helps us plan out the next quarter so I’m intentional about where I put my hours, and then it helps her manage my calendar and balance incoming requests.
• Help with communications – This one was not on Andrea’s list, but I’m adding it.  She ends up drafting some things for me (sometimes as small as an email, sometimes as large as a presentation, though with a lot more guidance), which is helpful…it’s always easier to edit something than create it.  I also usually ask Andrea to read any emails I send to ALL ahead of time to make sure they make sense from someone’s perspective other than my own, and she’s very helpful in shaping things that way.

This may not be true of all companies at all sizes and stages, but for companies like ours, I’d classify a great assistant as a bit of an alter ego, one definition of which is “second self” – literally an extension of you as CEO.  That means the person is acting AS YOU, not just doing things FOR YOU.  Think about the transitive property here.  Everything you do as CEO is (in theory) to propel the whole company forward.  So everything your alter ego does is the same.  A great assistant isn’t just your administrative assistant.  A great assistant is an overall enabler of company success and productivity.  You do have to invest a lot of time in getting someone up to speed in this role for them to be effective, and you have to pay well for performance, but a great assistant can literally double your productivity as CEO.

A Great American Experience

President Obama signed into law today a bill called the JOBS Act.  I haven’t read the full text of the law, but based on abstracts, my opinion of the JOBS Act is that it’s great for the startup community, but even greater for growth companies. I am less familiar with the Crowdsourcing components of the bill, but certainly that will make it easier for pure startups to attract micro capital.

The Sarbanes-Oxley reforms that make it easier and less costly to go through an IPO and be a public company will really enable growth companies like Return Path and many others in the Internet industry to go public a little earlier and with less difficulty. Tapping the public markets like that will enable the thriving Internet sector, which is one of the few truly high-growth segments of the economy, to grow even faster and create even more jobs.

Even better — George, Jack, and I were invited to attend the bill signing ceremony and speech in the Rose Garden at the White House!  Below are three pictures, one of the signing, one of the three of us, and one of me and Scott Dorsey, our friend and CEO of Exact Target, who we ran into there.

It was a great experience for the three of us overall.  Seeing the White House, the President, and a positive product of the legislative process up close and personal was great.  Hearing the President’s speech, which was a complete pep talk about the virtues of entrepreneurship and small businesses as the growth engines of the economy, was very inspirational.  And overall, the whole thing made all three of us so proud of everything that all 300+ of us, and our very strategic and patient investors and Board members, have accomplished at Return Path these past dozen years.  We ARE part of the global growth story.  And we should all be excited about that!

Scaling Me

Two things have come up over the last couple years for me that are frustrations for me as a CEO of a high growth company.  These are both people related — an area that’s always been the cornerstone of my leadership patterns.  That probably makes them even more frustrating.

Frustration 1:  Not knowing if I can completely trust the feedback I get from deep in the organization.  I’ve always relied on direct interactions with junior staff and personal observation and data collection in order to get a feel for what’s going on.  But a couple times lately, people had been admonishing me (for the first time) when I’ve relayed feedback with comments like, “of course you heard that — you’re the CEO.”

So now the paranoid Matt kicks in a bit.  Can I actually trust the feedback I’m getting?  I think I can.  I think I’m a good judge of character and am able to read between the lines and filter comments and input and responses to questions I ask.  But maybe this gets harder as the organization grows and as personal connections to me are necessarily fewer and farther between.

Frustration 2:  Needing to be increasingly careful with what I say and how I say it.  This comes up in two different ways.  First, I want to make sure that while I’m still providing as transparent leadership as I can, that I’m not saying something that’s going to freak out a more junior staff member because they’re missing context or might misinterpret what I’m saying.  Ok, this one I can manage.

But the tougher angle on this is having unintended impact on people.  Throwing out a casual idea in a conversation with someone in the company can easily lead to a chain reaction of “Matt said” and “I need to redo my goals” conversations that aren’t what I meant.  So I’ve done some work to formalize feedback and communication loops when I have skip-level check-ins, but it’s creating more process and thought overhead for me than I’m used to.

Nothing is bad here – just signs of a growing organization – but some definite changes in how I need to behave in order to keep being a strong and successful leader.