There’s been much coverage in the news of Saturday’s passing of President Ronald Reagan, but I will add a new wrinkle by trying to distill down what I know and remember of The Great Communicator’s leadership style into a few simple lessons of note for CEOs.

Lesson 1: Sunny optimism motivates the people you lead, but only when it’s balanced with hard-headed realism. Reagan’s message that tomorrow can be a better day than today was powerful and timely for the American psyche, but he didn’t just assume that because he said it, it would be true. He backed up his message with (a) an understanding that the American economy itself was in the doldrums in the late ’70s, and (b) policies designed to fix the economy. Whether you agree with those policies or not, you have to respect the fact that Reagan as a leader wasn’t just talk — he combined the talk with reality-based action. That’s super important when communicating key messages to a company of any size.

Lesson 2: Simplicity of messaging beats out measured intellectualism in broad-based communications. Reagan’s view of the 40-year-old Cold War when he took office was “we will win, and they will lose.” Much easier to rally around than messages of detente and containment (this quote came from an editorial by former Reagan staffer Peter Robinson in today’s Wall St. Journal). Similarly, the bigger and more diverse the group you’re talking to inside your company or in a speech or in the press, the more important it is to boil your key message down to something people can easily take away with them and repeat at home later to their spouse or friends.

Lesson 3: Nobody’s perfect, and you don’t have to be perfect either. He may have been, electorally, the most popular president of our generation, but Reagan certainly had his many and sometimes glaring faults. History will acknowledge his faults but overall judge him on his performance. It was noted (also in today’s Journal, I think) that Reagan got a lot of little things wrong, but in the end, he will be remembered because he got a few big things very, very right. Perfection is something that most mortals can’t achieve, certainly not in a high profile position like President or CEO of anything, whether a 10-person startup or a nation.

Love him or hate him, the man was one of the most prominent leaders of our time. I’m sure there are more lessons from Reagan’s legacy than these three for CEOs, but this is a start, anyway.

Academic Inspiration

I just read in my alumni magazine that at Opening Exercises for incoming freshmen this year, Princeton President Shirley Tilghman closed her remarks with the following:

For the next four years, you will be encouraged – and indeed sometimes even exhorted – to develop the qualities of mind that allowed Katherine Newman, Simon Morrison, and Alan Krueger to change what we know about the world.  Those qualities are the willingness to ask an unorthodox question and pursue its solution relentlessly; to cultivate the suppleness of mind to see what lies between black and white; to reject knee-jerk reactions to ideas and ideologies; to recognize nuance and complexity in an argument; to differentiate between knowledge and belief; to be prepared to be surprised; and to appreciate that changing your mind is not a sign of weakness but of strength.  We ask you to be open to new ideas, however surprising; to shun the superficial trends of popular culture in favor of careful analysis; and to recognize propaganda, ignorance, and baseless revisionism when you see it.  That is the essence of a Princeton education.

While some of these comments are more appropriate for an academic setting, how many of us who run businesses want to encourage the same behavior and thoughtfulness of our employees?  Here are a few examples taken from the above.

To change what we know about the world — a hallmark of a successful startup is to invent new products and services, to change the way the world works in some small way.  In our case, to fix some of the most critical problems with email marketing.

The willingness to ask an unorthodox question and pursue its solution relentlessly — reinventing some part of the world only comes by challenging the status quo.  Return Path was started by asking an unorthodox question:  why isn’t there an easy way for people to change their email address online?

To cultivate the suppleness of mind to see what lies between black and white; to recognize nuance and complexity in an argument — the longer I run a company, the less black and white I see.  When I do seev it, I think of it as a gift.  The rest of the day is spent trying to figure out the zone in between.  Making 51/49 decisions all day long is difficult, but it’s easier when the rest of the organization is capable of doing the same thing.

To appreciate that changing your mind is not a sign of weakness but of strength; to be open to new ideas, however surprising — perseverance in business is critical; stubbornness is deadly.  How does the old saying go?  The definition of Insanity is doing the same thing over and over again but expecting different results.  If the only thing we were still doing at Return Path is ECOA, we’d be long gone by now, or at least MUCH smaller than we are today.

I don’t know too many entrepreneurs that don’t espouse most of the above principles.  The trick is to build an entire company of people that do.

The Gift of Feedback

My colleague Anita Absey always says that “feedback is a gift.”  I’ve written in the past about our extensive 360 review process at Return Path, and also about how I handle my review and bring the Board in on it.  But this past week, I finished delivering all of our senior staff 360 reviews, and I received the write-up and analysis of my own review.  And once again, I have to say, the process is incredibly valuable. 

For the first time in a long time this year, I got a resounding “much improved” on all of my prior year’s development items from my team and from the Board.  This was great to hear.  As usual, this year’s development items are similarly thoughtful and build on the prior ones, in the context of where the business is going.  Since one of my prior year’s items was “be as transparent as possible,” I thought I’d share my development plan for the coming 12-18 months here on my blog.  If you’re reading this and you report to me, you’ll get a longer form debrief at our next offsite.

1. Continue making the organization more of a Hedgehog, lending more focus to our mission and removing distractions wherever possible.

2. Move the organization’s leadership team from “pacesetting” to “authoritative” management styles by focusing more on :

    a. standards of excellence around employee behavior and performance: develop a more clear performance management system, raise the bar on accountability around leadership and management issues, shift management training from tools to values-based coaching

    b. clear communication loops: balance open door policy with manager empowerment by getting the executive in charge to fix issues (instead of fixing them myself) and/or facilitating stronger manager-employee communication

    c. constant translation of vision into execution: foster clearer context and deeper employee engagement by not just communicating vision, but communicating HOW the vision becomes reality at every opportunity

3. Sharpen elbows further around leadership team: identify key attributes of success, weed out underperformers, re-scope other roles, and clarify “partner for success” opportunities as part of core responsibilities. Make each individual’s development needs public in the senior team (I guess this is the first step towards that!)

4. Make the organization more nimble, inspiring a bias for action through shifts in priorities and cross-functional swat teams where required

So there you go.  If you work at Return Path, please feel free to hold my feet to the fire in the coming months on these points!

Call Me

A fine song by Blondie from 1980 and from the soundtrack of the movie American Gigolo.  And also something that reminded me about the importance of not relying too much on email this past month. 

 I had surgery on my left wrist in early March to hopefully fix a nagging tendonitis problem.  And while I could still write and type post-op, I got sore pretty quickly every day, so I tried to keep those activities to a minimum.  As you might imaging, I do an awful lot of email and IM in my line of work.  So what was my short response to a huge number of emails and IMs for a few weeks?  “Call me.”

 My communications, especially with remote employees, not only didn’t suffer while I couldn’t type a lot – they were stronger than ever.  Even short, two-minute phone conversations – the remote equivalent of someone sticking their head in my office – are preferable to IM or email in many cases.  There’s nothing like the sound of someone’s voice to add real texture to a dialog and to avoid misunderstandings.

I just said this to a fellow little league coach, and it’s certainly true for baseball.  I’ve coached games with sloppy and/or blowout wins in the past.  You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game.  And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run.  You are sad about the L, but at least you left it all out on the field.

Is that statement true in business?

What’s an example of a “bad” win?  Let’s say you close a piece of business with a new client…but you did it by telling the client some things that aren’t true about your competition.  Your win might not be sustainable, and you’ve put your reputation at risk.  Or what about a case where you release a new feature, but you know you’ve taken some shortcuts to launch it on time that will cause downstream support problems?  Or you negotiate the highest possible valuation from a new lead investor, only to discover that new lead investor, now on your Board, expects you to triple it in four years and is way out of alignment with the rest of your cap table.

On the other side, what’s an example of a “good” loss?  We’ve lost accounts before where the loss was painful, but it taught us something absolutely critical that we needed to fix about our product or service model.  Or same goes for getting a “pass” from a desirable investor in a financing round but at least understanding why and getting a key to fixing something problematic about your business model or management team.

What it comes down to is that both examples – little league and business – have humans at the center.  And while most humans do value winning and success, they are also intrinsically motivated by other things like happiness, growth, and truth.  So yes, even in business, sometimes a good loss is better than a bad win.

Book Short:  Underdog Victorious

The Underdog Advantage, by David Morey and Scott Miller, was a worthwhile read, though not a great book.  It was a little shallow, and although I enjoyed its case studies (who doesn’t love hearing about Ben & Jerry’s, Southwest, JetBlue, Starbucks?), I didn’t feel like the authors did enough to tie the details of the success of the case study companies back to the points they made in the book.

That said, the book had some great reminders in it for companies of all sizes and stages.  The main point was that successful companies always think of themselves as the underdog, the insurgent, and never get complacent.  They run themselves like a political campaign, needing to win an election every single day.  A lot of the tactics suggested are timeless and good to remember…things like never declare victory, always play offense, always respond to attacks, remember to communicate from the inside out, and remember to sell employees on a mision and purpose in order to make them your main ambassadors.  The laundry list of tactics is the book’s greatest strength.

I’ve always thought that the ability to stare down adversity in business — or turning lemons into lemonade, as a former boss of mine used to say — is a critical part of being a mature professional. We had a prime example of this a couple weeks ago at Return Path.

We had scheduled a webinar on email deliverability, a critical topic for our market, and the moment of the webinar had come, with over 100 clients and prospects on the line for the audio and web conference. There was a major technical glitch with our provider, Webex (no link for you, Webex), and after 5 or 10 minutes, we had to cancel the webinar — telling all 100 members of our target audience that we were sorry, we’d have to reschedule. What a nightmare! Even worse, Webex displayed atrocious customer service to us, not apologizing for the problem, blaming it on us (as if somehow it was our fault that half the people on the line couldn’t hear anything), and not offering us any compensation for the situation.

As you can imagine, our marketing guru Jennifer Wilson was devastated. But instead of sulking, she turned the situation on its head. She rescheduled the event for three weeks out with a different provider who was technically competent and a pleasure to work with, Raindance, and sent every person who’d been on our aborted webinar a gift certificate to Starbucks so they could enjoy a snack on our dime during the rescheduled event. Not only did we have full attendance at the rescheduled event, but Jennifer received dozens of emails from clients sympathizing with her, commending her on her attitude, and of course thanking her for the free latte.

It’s hard to do, and you hate to have to do it, but successfully turning lemons into lemonade is one of the most satisfying feelings in business!

People rarely comment on this blog (or most non-political blogs, I’ve noticed), so feel free to share your best lemons-to-lemonade story with me in a comment, and I promise I’ll post the best couple of them pronto!

Counter Cliche:  No Conflict, No Interest

The entrepreneur’s take on Fred’s VC cliche of the week — "No conflict, No interest" is that it applies equally but differently to management teams. 

Our nation’s first president, George Washington, is often said to have brilliantly placed political enemies Thomas Jefferson and Alexander Hamilton on his first cabinet so he would have differing points of view from which to choose when deciding some of the complex and delicate issues that faced our nation in its infancy.  And many of those early decisions of the Washington administration — things like how to pay down the debt from the Revolution, or whether and how to put down the Whiskey Rebellion — were critical in forming our nation and deciding how much power to invest in our government.

The tension between one executive and another on a management team is, though perhaps less historically important, no different.  A management team that finds itself 100% in agreement, 100% of the time, is in trouble.  A management team that can have disagreements and use that tension productively to drive decisions is much better off.  Building such a team requires the CEO to seek out executives who view the world differently, who have the courage to speak their minds in the face of strong opposition, and who have the ability to see different points of view.

7 Years On

My last September 11 as a New York City resident. I walked down to the World Trade Center site this morning as I have each of the last six 9/11s and rang The Bell of the Unforgotten, which is the New York City Fire Department’s port-a-memorial that they bring out for the day. As a long-time member of the lower Manhattan community, the day always bring out a lot of reflection for me. Seeing the memorial flood lights on tonight will do the same and bookend the day.

The main thing I was thinking about this morning was why there’s been nothing really built yet on the site. World Trade Center 7 (which is actually adjacent to the main site) went up in a hurry a few years ago (pictured here under construction four years ago), but nothing else.

My general understanding of the situation is that the holdup has not been around clean-up or pre-construction the last several years, but all about legal, political, and insurance issues. And that smacks to me of a leadership problem. I realize there are a lot of parties involved, and a lot at stake, but it’s just embarrassing to America that we haven’t rebuilt the site — and fast. Set an example to the rest of the world that we react swiftly and don’t let the bad guys knock us down…and keep us down.

It feels to me like a President who actually understood leadership would have gotten all the parties in a room together and not let them out until there was agreement on a plan. Don’t just let “the system” play things out laissez faire, but actually play them out in a hurry so the country and city can move forward. It feels like the kind of thing Reagan or Clinton would have done.

As I reflect on this today, the one thing I’m happy about is that no matter who wins the White House, America will be getting a leadership upgrade.

Naked Talking

Naked Conversations:  How Blogs Are Changing The Way Businesses Talk with Consumers, by Robert Scoble and Shel Israel, would have been mildly interesting had I never read, let alone written, a blog.  So chances are if you’re reading this blog regularly, it’s not a great use of your time or money, but if you just ran across this post while trying to learn more about blogging – or really about any form of post-2002 Internet marketing – it’s probably worthwhile as a primer. But if you’re knee-deep in internet marketing or blogging, it may be a bit of a snoozer.

I find it entertaining that leading bloggers like Scoble and Israel, who are part of the ultra-small group of hardcore bloggers, as they describe, that “posts 50 times a day, mostly at 4 a.m.,” think blogs are really conversations.  Don’t get me wrong, I believe that blogs are revolutionary in that they allow anyone to run his or her own printing press.  I also think it’s critical for companies to have corporate blogs (Return Path had one of the first), for CEOs and other executives to blog (obviously I do), for companies to allow their employees to blog relatively unencumbered by corporate policy, and, perhaps most important, for companies to track and listen to what others who blog are saying about them and their products.

But let’s not get too caught up in our own euphoria as bloggers to think that what’s happening is actually a conversation the way we humans think of conversations.  Blogging allows more people to have their voices heard, and it certainly allows for transparency and authenticity, as the authors say, but there’s almost never dialog.  Many popular blogs don’t have comments at all.  Those who do allow comments have few if any posted.  And those who have comments posted rarely have any other readers who actually see the comments, since the blog is a publishing forum and RSS is a publishing format, neither is a truly interactive medium like chat.

I’m sure there are some blogs that have active commenters, particularly political ones, and hopefully someone, somewhere, reads and internalizes those comments when they’re relevant. And certainly, high circ bloggers who read and know each other participate in a dialog by talking AT each other via their blog postings, not via comments (meaning that for the “dialog” to make sense to the greater world, the greater world must read all blogs participating in a “conversation.”). But, please, let’s not pretend there is really a 20-million-way conversation happening.

An Execution Problem

My biggest takeaway from the TED Conference this week is that we — that is to say, all of us in the world — have an execution problem.  This is a common phrase in business, right?  You’ve done the work of market research, positioning, and strategy and feel good about it.  Perhaps as a bigger company you splurge and hire McKinsey or the like to validate your assumptions or develop some new ones.  And now all you have to do is execute — make it happen.  And yet so many businesses can’t make the right things happen so that it all comes together.  I’d guess, completely unscientifically, that far, far more businesses have execution problems than strategic ones.  Turns out, it’s tough to get things to happen as planned BUT with enough flexibility to change course as needed.  Getting things done is hard.

So what do I mean when I say that humanity has an execution problem?  If nothing else, the intellectual potpourri that is TED showed me this week that we know a lot about the world’s problems, and we don’t lack for vision and data on how to solve them.  A few of the things we heard about this week are the knowledge — and in many cases, even real experiences — about how to:

– Steer the evolution of deadly disease-causing bacteria to make them more benign within a decade

– Build world class urban transportation systems and growth plans to improve urban living and control pollution

– Drive down the cost of critical pharmaceuticals to developing nations by 95%

– Dramatically curb CO2 emissions

We have the knowledge, and yet the problems remain unsolved.  Why is that?  Unlike the organized and controlled and confined boundaries of a company, these kinds of problems are thornier to solve, even if the majority of humans agree they need to be solved.  Whether the roadblock is political, financial, social — or (d) all of the above — we seem to be stuck in a series of execution problems.

The bright spot out of all of this (at least from this week’s discussions) is that, perhaps more than ever before in the history of mankind, many of our most talented leaders AND our wealthiest citizens are taking more of a personal stake in not just defining the problems and solutions, but making them happen.  They’re giving more money, buiding more organizations, and spending more time personally influencing society and telling and showing the stories.  It will take years to see if these efforts can solve our execution problems, but in the meantime, the extraordinary efforts are things we can all be proud of.