How to Quit Your Job

I sent an email out to ALL at Return Path a few years ago with that as the subject line.  A couple people suggested it would make a good blog post in and of itself.  So here’s the full text of it:

ALL –

This may be one of the weirdest emails you’ll see me (or any CEO write)…but it’s an important message that I want to make sure everyone hears consistently.  If nothing else, the subject line will probably generate a high open rate.  🙂

First off, I hope no one here wants to leave Return Path.  I am realistic enough to know that’s not possible, but as you know, employee engagement, retention, and growth & development are incredibly important to us.

But alas, there will be times when for whatever reason, some of you may decide it’s time to move on.  I have always maintained that there’s more than a Right Way and a Wrong Way to leave a job.  For me, there’s a Return Path Way.

I suppose the Right Way is the standard out there in the world of two weeks’ notice and an orderly documentation and transition of responsibilities.  The Wrong Way is anything less.

So what’s the Return Path Way?

It starts with open dialog.  If you are contemplating looking around for something else, you should let someone know at the thinking stage.  Ideally that would be your manager, but if you’re not comfortable starting the conversation there, find someone else — your department head, someone in HR, me.  Let someone who is in a position to do something about it know that you’re considering other options and why.  The worst thing that will happen is that the company isn’t able to come up with a solution to whatever issues you have.  I PROMISE you that no one here in any management position will ever think less of you or treat you differently or serve up any kind of retribution for this kind of conversation.

After the open dialog and any next steps that come out of it, if you are still convinced that leaving is the right thing for you, tell your manager and whoever you spoke to at the beginning of your search process, not at the end of it.  That hopefully gives the company enough lead time to find a replacement and provide for enough overlap between you and the new hire so that you can train your replacement and hand things off.

Why do we feel so strongly about this?

We invest heavily in our people.  I know we’re not perfect — no company is — but we do our best to take good care with everyone who works here.  Hopefully you know that.  And hiring great people is difficult, as you also know.  Losing a well trained employee is VERY PAINFUL for the company.  It slows our momentum and causes at least a minor level of chaos in the system.  And as shareholders or future shareholders (even if you leave – you can exercise your vested stock options), I’d hope that’s something none of you want to do.

I realize the Return Path Way that I am outlining here is unconventional (and potentially uncomfortable).  But Return Path is an unconventional place to work in a lot of ways.

As I said up front, I hope none of you wants to leave…but if you do, please take this request and advice to heart.

Thank you!

-Matt

Now…I sent this out when the company was a lot smaller, when losing a single employee was losing a real percentage of our workforce!  But I stand by every word in the email, even at a larger size.  This kind of dialog is, as I note in the email, both unconventional and uncomfortable.  But just as one of my management mantras here is “no one should ever be surprised to be fired,” another is “we should never be surprised when someone resigns.”  Ultimately, it’s up to each individual manager to set the right tone with his or her team, and also be in tune enough with each of his or her team members, to foster this.

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.

Book Not-So-Short:  Not Just for Women

At the request of the women in our Professional Services team, I recently read Sheryl Sandberg’s Lean In:  Women, Work, and the Will to Lead, and while it may seem like dancing the meringue in a minefield for a male CEO to blog about it, I think it’s an important enough topic to give it a shot.  So here goes.

First, given the minefield potential, let me issue a few caveats up front.  These are deep, ages old, complex, societal issues and behaviors we’re talking about here.  There is no quick answer to anything.  There is no universal answer to anything.  Men don’t have the same perspective as women and can come across as observers (which in some respects, they are).  Working moms don’t have the same perspective as stay-at-home moms, or as single women.  We try to be good about all these issues at Return Path, but I’m sure we’ve only scratched the surface.  </caveats>

Perhaps most important, my overall take on the book is that it’s a very good business book that everyone should read – not just women.  I have a strong reaction to the reactions I’ve read and heard about the book – mostly from women dismissing the book because Sandberg has immense financial resources, so how could she possibly know the plight of the ordinary mom, and how could she understand what it is like to be a stay-at-home mom?  That reaction is to dismiss the dismissals!  I found the book to be very broadly applicable.  Of course things about life with a two-working parent family are easier if you have more money.  But that’s completely not the point of the book.  And Sandberg doesn’t once criticize stay-at-home moms for that choice – in fact, she acknowledges feelings of guilt and inferiority around them and admiration for the work they do that benefits all families and kids, not just their own.

Here are a few of the biggest areas of thinking, AHA, or questioning, that the book gave me:

• One of Sandberg’s underlying points is that the world would be a better place with more women in leadership positions, so that’s an important goal.  It’s interesting that few enough of our leaders are women, that it’s hard for me to draw that same conclusion, but it makes sense to me on the surface, and there’s some research about management teams and boards to back it up.  As far as I can tell, the world has yet to see a brutal female dictator.  Or a fair share of political or corporate scandals caused by women.  There are definitely some horror stories of “tough boss” women, but probably no more than “tough boss” men.  It’s interesting to note that in our society, leadership roles seem to be prized for their power and monetary reward, so even if the world wouldn’t be a better place with more female leaders, it would certainly be a more fair place along those two dimensions
• I felt that a bunch of Sandberg’s points about women were more generalizations about certain personality types which can be inherent in men and women.  Maybe they’re more prevalent in women, even much more, but some are issues for some men as well.  For example, her general point about women not speaking up even if they have something to say.  I have seen this trait in women as well as more introverted men.  As a leader, I work hard to draw comments out of people who look like they have something to say in a meeting but aren’t speaking up.  This is something that leaders need to pay close attention to across the board so that they hear all the voices around their tables.  Same goes for some of the fears she enumerates.  Many male leaders I know, myself included at times, have the “fear of being found out as a fraud” thought.  Same goes for the “desire to be liked by everyone” holding people back – that’s not gender specific, either.  All that said, if these traits are much more prevalent in women, and they are traits that drive attainment of leadership roles, well, you get the point
• The fact that women earn 77 cents on the dollar in equivalent jobs for men is appalling.  I’ve asked our People Team to do a study of this by level, factoring in experience and tenure, to make sure we don’t have that bias at Return Path.  I know for sure we don’t at the leadership level.  And I sure as heck hope we don’t anywhere in the organization.  We are also about to launch an Unconscious Bias training program, which should be interesting
• Sandberg made a really interesting point that most of the women who don’t work are either on the low end or high end of the income spectrum.  Her point about the low end really resonated with me – that women who don’t earn a lot stop working if their salaries only barely cover childcare costs.  However, she argues that that’s a very short term view, and that staying in the workforce means your salary will escalate over time, while childcare costs stay relatively flat.  This is compounded by the fact that women who lean back early in their careers simply because they are anticipating someday having children are earning less than they should be earning when they do finally have children.
• The other end of the income spectrum also made sense once I parsed through it – why do women whose husbands make a lot of money (most of whom make a lot of money as well) decide to off-ramp?  Sandberg’s point about the “Leadership ambition gap” is interesting, and her example of running a marathon with the spectators screaming “you know you don’t have to do this” as opposed to “you’ve got this” is really vivid.  See two bullets down for more on this one.  But it might not be straight-up Leadership Ambition Gap so much as a recognition that some of the high-earning jobs out there are so demanding that having two of them in the household would be a nightmare (noting that Dave and Sheryl seem to have figured some of that out), or that moms don’t want to miss out on that much of their children’s lives.  They want to be there…and they can afford to.  Another related topic that I wish Sandberg had covered in more depth is the path of moms who off-ramp, then re-on-ramp once their youngest children are in school, whether into the career they left or a different one.  That would be an interesting topic on many fronts
• Societal influences must matter.  The facts that, in 2011 – Gymboree manufactured onesies that say “smart like Daddy” and “pretty like Mommy,” and that JC Penney teenage girl t-shirts say “I’m too pretty to do homework so my brother has to do it for me” are more than a little troublesome on the surface (unless Gymboree also produces “handsome like Daddy” and “wicked smart like Mommy,” which somehow I doubt).  The fact that women do worse on math and science tests when they have to identify their gender at the top of the test is surprising and shocking
• I am really fortunate that Mariquita only works part time, and it’s unclear to me how our lives would work if we both worked full time, especially given my extremely heavy travel schedule, though I am sure we’d figure it out.  And there’s no way that I carry 50% of the burden of household responsibilities.  Maybe 20-25% at best.  But I was struck by Sandberg’s comments (I am sure true) that in two-working-parent families, women still carry the preponderance of household responsibilities on their shoulders.  I totally don’t get this.  If you both work, how can you not be equal partners at home?  A quick mental survey of a couple of the two-working-parent families we know would indicate that the parents split household responsibilities somewhat evenly, though you can never know this from the outside.  This should be a no brainer.  Sandberg’s point that men need to “lean into their families” is spot on in these cases for sure
• On a related note, Sandberg’s comment that “as women must be more empowered at work, men must be more empowered at home…moms can be controlling and critical…if he’s forced to do things her way, pretty soon she’ll be doing them herself” made me smile.  I have definitely seen this “learned helplessness” on the home front with dads quite a bit over the years
• One really good point Sandberg makes is that younger employees who don’t have kids should be allowed to have a life outside of work just as much as women who do have kids.  And that she pays people for the quality and quantity of their output, not their hours.  These are principles that match our values and philosophy at Return Path 100%
• Probably the most startling moment in the book for me – and I suspect many other men – was Sandberg’s vignette about the young woman at Facebook who was starting to “lean back” because she might someday have a family – before she was even dating anyone!  This really gave me a lot of pause.  If widespread (and I assume it is), there are clearly societal forces at work that we need to do more to help women early in their careers overcome, if they want to overcome them
• Sandberg’s point that a rich and fulfilling career “is a Jungle Gym, not a Ladder” is spot on, but this is true for men as well as women.  It matches our philosophy of Scaling Horizontally perfectly
• Another very poignant moment in the book was when Sandberg talked about how she herself had shown bias against women in terms of who she called on in meetings or lectures during Q&A.  Again, lots of pause for me.  If female leaders have the same societal bias against women, that’s a sign that we all have real work in front of us to help level the playing field around giving women air time.  Similarly, her example of the Heidi/Howard study was fascinating around how women with the same characteristics are perceived differently by both male and female co-workers gives me pause (for the record, I know the Heidi in question, and I like her!).  Likewise, the fact that female leaders are often given unflattering nicknames like “The Iron Lady” – you’d never see something like that for a man in the same position.  At least Thatcher wore the name as a badge of honor

I hope this post doesn’t end up as a no-win piece of writing where all I do is touch a few nerves and inspire no ongoing dialog.  “Let’s start talking about it,” the ending theme of the book, is a great way to end this post as well.  As with all tough issues, articulating the problem is the first step toward solving it.  Women need to allow men (as long as the men are open-minded, of course!) to think what they think, say what they think in a safe space, and blunder through their own learnings without feeling threatened.  And men need to be comfortable having conversations about topics like these if the paradigmatic relationship between women and leadership is going to continue to shift instead of avoiding the topic or just calling in HR.

Hopefully this blog post is one step towards that at my company.  Return Path colleagues – feel free to comment on the blog or via email and share stories of how we’ve either helped you or held you back!  But overall, I’m glad I read this book, and I’d encourage anyone and everyone to read it.

Running a Productive Offsite

A couple OnlyOnce readers asked me to do a post on how I run senior team offsites.  It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.

My senior team has four offsites per year.  I love them.  They are, along with my Board meetings, my favorite times of the year at work.  Here’s my formula for these meetings:

–          WHY:  There are a few purposes to our offsites.  One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level.  So for us, these are the only times of the year that we are actually in the same place.  But even if we were all in one place, we’d still do them.  The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time.  The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics.  It’s critically important to build and sustain deep relationships across the Executive Team.  We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company.  As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical

–          WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total).  Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people).  That part is new as we’ve gotten bigger.  In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics

–          WHERE:  Offsites aren’t always offsite for us.  We vary location to make geography work for people.  And we try to contain costs across all of them.  So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel.  Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place.  Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night

–          WHEN:  4x/year at roughly equal intervals.  We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded.  Now we basically do them between Board meetings.  The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year.  Our general formula when it’s the smaller group is two days and at least one, maybe two dinners.  When it’s the larger group, it’s three days and at least two dinners.  For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.

–          WHAT:  Our offsites are super rigorous.  We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations.  The agenda for these offsites varies widely, but the format is usually pretty consistent.  I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union.  Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc.  We always try to spend half a day on team and individual development.  Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing.  Then we have a team development plan check-in that’s the same, but about how the team is interacting.  We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time.  Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!).  There’s also time at breaks for sub-group meetings and ad hoc conversations.  We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it.  Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m.  We usually have a closing check-out, next steps recap type of exercise as well.

–          HOW:  Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.

I’m sure I missed some key things here.  Team, feel free to comment and add.  Others with other experiences, please do the same!

Blogiversary, Part VII

Today marks the seventh anniversary of OnlyOnce.  I haven’t marked the date with a post in three years, but here was my last such post (with links to prior posts in it).  In sum up until now, my reasons for blogging have been written up as:

• “Thinking” (writing short posts helps me crystallize my thinking)
• “Employees” (one of our senior people once called reading OnlyOnce “getting a peek inside Matt’s head)
• My book reviews help me crystallize my takeaways from books and serve as a bit of a personal reference library
• I like writing and don’t get to do it often

After seven years, though, I’m going to add another important point of value for me for writing OnlyOnce:  now, at 672 posts (including 27 that are scheduled but not yet posted – easy a record for me), this blog now serves as a repository for me of my own lessons learned, best practices, anecdotes, and aphorisms.  Thanks to Lijit, it’s easy for me and others to search.  Thanks to the new WordPress format and design by my friends at Slice of Lime, the categories and tagging make it much easier to navigate.

I probably get one question a week from a fellow CEO or prospective entrepreneur or employee that, instead of typing out an answer or setting up a meeting, I can actually just send a link as a starting point.  Sometimes there are follow-up questions, sometimes there aren’t.  But the blog is proving to be a very efficient form of documentation.

What Separates Good Teams from Bad Teams?

Every once in a while, I have a conversation that forces me to distill an idea to a sound bite – those frequently become blog posts.  Many happen with members of my team at Return Path, or my friend Matt on our Saturday morning runs, or my Dad or Mom, or Mariquita.  This one happened at dinner the other night with Mariquita and my in-laws Rick and Carmen.

The subject came up about managing a senior team, and different iterations of teams I’ve managed over the years.  And the specific question we posed was “What are the most significant characteristics that separate good teams from bad teams?”  Here’s where the conversation went…“I believe that 100% of the members of good teams can, 100% of the time”

1. Get outside of themselves.  They have no personal agenda, only the best interests of the company, in mind.  They make every effort to see issues on which they disagree from the opposing point of view
2. Understand the difference between fact and opinion.  As my friend Brad says, “The plural of anecdotes is not data.”  And as Winston Churchill said, “Facts are stubborn things.”  If everyone on a team not only understands what is a fact and what is not a fact, AND all team members are naturally curious to understand and root out all the relevant facts of an issue, that’s when the magic happens

Of course there are many other characteristics or checklists of characteristics that separate good teams from bad teams.  But these feel to me like pretty solid ones – at least a good starting point for a conversation around the conference room table.

Book Short:  Steve Jobs and Lessons for CEOs and Founders

First, if you work in the internet, grew up during the rise of the PC, or are an avid consumer of Apple products, read the Walter Isaacson biography of Steve Jobs (book, kindle).  It’s long but well worth it.

I know much has been written about the subject and the book, so I won’t be long or formal, but here are the things that struck me from my perspective as a founder and CEO, many taken from specific passages from the book:

• In the annals of innovation, new ideas are only part of the equation. Execution is just as important.  Man is that ever true.  I’ve come up with some ideas over the years at Return Path, but hardly a majority or even a plurality of them.  But I think of myself as innovative because I’ve led the organization to execute them.  I also think innovation has as much to do with how work gets done as it does what work gets done.

• There were some upsides to Jobs’s demanding and wounding behavior. People who were not crushed ended up being stronger. They did better work, out of both fear and an eagerness to please.  I guess that’s an upside.  But only in a dysfunctional sort of way.

• When one reporter asked him immediately afterward why the (NeXT) machine was going to be so late, Jobs replied, “It’s not late. It’s five years ahead of its time.”  Amen to that.  Sometimes product deadlines are artificial and silly.  There’s another great related quote (I forget where it’s from) that goes something like “The future is here…it’s just not evenly distributed yet.”  New releases can be about delivering the future for the first time…or about distributing it more broadly.

• People who know what they’re talking about don’t need PowerPoint.”  Amen.  See Powerpointless.

• The mark of an innovative company is not only that it comes up with new ideas first, but also that it knows how to leapfrog when it finds itself behind.  This is critical.  You can’t always be first in everything.  But ultimately, if you’re a good company, you can figure out how to recover when you’re not first.  Exhibit A:  Microsoft.

• In order to institutionalize the lessons that he and his team were learning, Jobs started an in-house center called Apple University. He hired Joel Podolny, who was dean of the Yale School of Management, to compile a series of case studies analyzing important decisions the company had made, including the switch to the Intel microprocessor and the decision to open the Apple Stores. Top executives spent time teaching the cases to new employees, so that the Apple style of decision making would be embedded in the culture.  This is one of the most emotionally intelligent things Jobs did, if you just read his actions in the book and know nothing else.  Love the style or hate it – teaching it to the company reinforces a strong and consistent culture.

• Some people say, “Give the customers what they want.” But that’s not my approach. Our job is to figure out what they’re going to want before they do. I think Henry Ford once said, “If I’d asked customers what they wanted, they would have told me, ‘A faster horse!’” People don’t know what they want until you show it to them. That’s why I never rely on market research. Our task is to read things that are not yet on the page.  There’s always a tension between listening TO customers and innovating FOR them.  Great companies have to do both, and know when to do which.

• What drove me? I think most creative people want to express appreciation for being able to take advantage of the work that’s been done by others before us. I didn’t invent the language or mathematics I use. I make little of my own food, none of my own clothes. Everything I do depends on other members of our species and the shoulders that we stand on. And a lot of us want to contribute something back to our species and to add something to the flow. It’s about trying to express something in the only way that most of us know how—because we can’t write Bob Dylan songs or Tom Stoppard plays. We try to use the talents we do have to express our deep feelings, to show our appreciation of all the contributions that came before us, and to add something to that flow. That’s what has driven me.  This is perhaps one of the best explanations I’ve ever heard of how creativity can be applied to non-creative (e.g., most business) jobs.  I love this.

My board member Scott Weiss wrote a great post about the book as well and drew his own CEO lessons from it – also worth a read here.

Appropos of that, both Scott and I found out about Steve Jobs’ death at a Return Path Board dinner.  Fred broke the news when he saw it on his phone, and we had a moment of silence.  It was about as good a group as you can expect to be with upon hearing the news that an industry pioneer and icon has left us.  Here’s to you, Steve.  You may or may not have been a management role model, but your pursuit of perfection worked out well for your customers, and most important, you certainly had as much of an impact on society as just about anyone in business (or maybe all walks of life) that I can think of.

What Makes an Awesome Board Member

(This post was requested by my long-time Board member Brad Feld and is also running concurrently on his blog today)

I’ve written a bunch of posts over the years about how I manage my Board at Return Path.  And I think part of having awesome Board members is managing them well – giving transparent information, well organized, with enough lead time before a meeting; running great and engaging meetings; mixing social time with business time; and being a Board member yourself at some other organization so you see the other side of the equation.  All those topics are covered in more detail in the following posts:  Why I Love My Board, Part II, The Good, The Board, and The Ugly, and Powerpointless.

But by far the best way to make sure you have an awesome board is to start by having awesome Board members.  I’ve had about 15 Board members over the years, some far better than others.  Here are my top 5 things that make an awesome Board member, and my interview/vetting process for Board members.

Top 5 things that make an awesome Board member:

• They are prepared and keep commitments.  They show up to all meetings.  They show up on time and don’t leave early.  They do their homework.  The are fully present and don’t do email during meetings
• They speak their minds.  They have no fear of bringing up an uncomfortable topic during a meeting, even if it impacts someone in the room.  They do not come up to you after a meeting and tell you what they really think.  I had a Board member once tell my entire management team that he thought I needed to be better at firing executives more quickly!
• They build independent relationships.  They get to know each other and see each other outside of your meetings.  They get to know inviduals on your management team and talk to them on occasion as well.  None of this communication goes through you
• They are resource rich.  I’ve had some directors who are one-trick or two-trick ponies with their advice.  After their third or fourth meeting, they have nothing new to add.  Board members should be able to pull from years of experience and adapt that experience to your situations on a flexible and dynamic basis
• They are strategically engaged but operationally distant.   This may vary by stage of company and the needs of your own team, but I find that even Board members who are talented operators have a hard time parachuting into any given situation and being super useful.  Getting their operational help requires a lot of regular engagement on a specific issue or area.  But they must be strategically engaged and understand the fundamental dynamics and drivers of your business – economics, competition, ecosystem, and the like

My interview/vetting process for Board members:

• Take the process as seriously as you take building your executive team – both in terms of your time and in terms of how you think about the overall composition of the Board, not just a given Board member
• Source broadly, get a lot of referrals from disparate sources, reach high
• Interview many people, always face to face and usually multiple times for finalists.  Also for finalists, have a few other Board members conduct interviews as well
• Check references thoroughly and across a few different vectors
• Have a finalist or two attend a Board meeting so you and they can examine the fit firsthand.  Give the prospective Board member extra time to read materials and offer your time to answer questions before the meeting.  You’ll get a good first-hand sense of a lot of the above Top 5 items this way
• Have no fear of rejecting them.  Even if you like them.  Even if they are a stretch and someone you consider to be a business hero or mentor.  Even after you’ve already put them on the Board (and yes, even if they’re a VC).  This is your inner circle, and getting this group right is one of the most important things you can do for your company

I asked my exec team for their own take on what makes an awesome Board member.  Here are some quick snippets from them where they didn’t overlap with mine (with only two inside jokes that I couldn’t resist putting up for the Board):

• Ethical and high integrity in their own jobs and lives
• Comes with an opinion
• Thinking about what will happen next in the business and getting management to think ahead
• Call out your blind spots
• Remembering to thank you and calling out what’s right
• Role modeling for your expectations of your own management team – Do your prep, show up, be fully engaged, be brilliant/transparent/critical/constructive and creative.  Then get out of our way
• Offer tough love…Unfettered, constructive guidance – not just what we want to hear
• Pattern matching:  they have an ability to map a situation we have to a problem/solution at other companies that they’ve been involved in – we learn from their experience…but ability and willingness to do more than just pattern matching.  To really get into the essence of the issues and help give strategic guidance and suggestions
• Ability to down 2 Shake Shack milkshakes in one sitting
• Colorful and unique metaphors

Disclaimer – I run a private company.  While I’m sure a lot of these things are true for other types of organizations (public companies, non-profits, associations, etc.), the answers may vary.  And even within the realm of private companies, you need to have a Board that fits your style as a CEO and your company’s culture.  That said, the formula above has worked well for me, and if nothing else, is somewhat time tested at this point!

Several years ago, I blogged about the training program we created for entry-level employees at Return Path, including an embedded presentation that we used to use (which I hope still works on the blog after all these years).

My brother Michael, who is an experienced manager and leader in the digital marketing space, recently sent me this email that I thought I’d share along the same lines to colleagues who are new to the working world. Enjoy!

I signed up to give advice on LinkedIn, and had someone just starting her first job reach out to me asking for general advice. I came up with the attached, and thought it might make for a good blog post on Only Once. If you decide not to publish it, I’m totally cool with that, but thought I would share it. After all, you’re only a brand new employee once too 🙂

1) Listen as much as possible. One of my mentors was fond of reminding me, “God gave you two ears and one mouth!” You should listen at least twice as much as you talk. Get to know your environment and the people around you. Take notes. Observe as much as possible. Learn how others are able to provide value to the organization. Start to anticipate little things that need to be done, and then do them before your manager asks you to. Then bit by bit, use your creativity to start to develop bigger hypotheses about how you can provide even greater value. 

2) “In business, the best story wins.” That’s another quote from a former manager of mine that I have found to be universally true. People in business respond to many things: numbers, bullet points, graphs and visualizations. But they respond to all of those things better when they are wrapped in stories. A great book you can read about storytelling is not about business at all. It’s called “Story” by Robert McKee, and it’s about screenwriting. Despite its apparent lack of applicability, I assure you it will help you think about characters, goals, antagonists, drama, obstacles, and structure — all the elements that go into a good story. When you can present your hypotheses in the context of a story, about your business, your customers, what you want to achieve, how you will do it, and why it matters, you will build consensus and show leadership. Another great book you can read here, again, not about business at all, is “Sapiens” by Yuval Noah Harari. It really opened my eyes about how so much of human history and behavior is really just based on stories. 

3) Be lean. There is another book you should read, called “The Lean Startup”, by Eric Ries. This one is actually about business :). As you think about your hypotheses, think of them in the context of how you can get to market quickly and inexpensively. How you can easily perform experiments that will test your hypotheses. Some of your experiments will not achieve your desired result, but it’s not a failure if you can learn something that helps you pivot towards success. Learnings enable you to adjust and refine your hypotheses as you try to find more value for your organization. 

4) “Objections are requirements” and a corollary “ask questions, don’t make statements.” These two gems are from that first mentor in item number one. Even if you can tell great stories, and even if you can devise and execute lean experiments that achieve business results or provide validated learnings, sometimes “haters gonna hate.” There will always be inhibitors to your bold ideas, with reasons not to proceed with your experiments. Inertia is part of human nature. But don’t fear! When an inhibitor comes along, the first thing you do is start to ask questions. “Why do you object to x?” “Oh,” they’ll say, “because of y and z.” Then ask another question “So if we can resolve y and z, then can we proceed with x?” Rather than repeating yourself and making more statements, by asking questions you’ve just turned their objections into requirements. That inhibitor no longer has their reasons not to proceed with your bold idea. You’ve turned them from antagonists into allies. This kind of creative problem solving is critical to getting your experiments into market, and building consensus and showing your leadership without alienating anyone. 

5) Ok I know I said four, but this one is optional (albeit important). Have fun! Do not take yourself or your role too seriously. Show your personality. Be yourself. That sort of general approach to work and life will draw people to you. They will be relaxed and comfortable around you. They will look forward to meetings with you. You will be successful if you are a good listener, a creative thinker with bold ideas, a fantastic storyteller, an agile experiment developer, and a leader who can build consensus and drive value. But if you are all those things, and you’re fun to be around? Then you will be unstoppable.

Thank you, Michael, for the contribution!

The Advantage: Why Organizational Health Trumps Everything Else In Business is Patrick Lencioni’s newest book.  Unlike most or all of his other books (see the end of this post for the listing), this one is not a fable, although his writing style remains very quick and accessible.

I liked this book a lot.  First, the beginning section is a bit of a recap of his Five Dysfunctions of a Team which I think was his best book.  And the ending section is a recap of his Death by Meeting, another really good one.  The middle sections of the book are just a great reminder of the basic building blocks of creating and communicating strategy and values – about driving alignment.

But the premise, as the subtitle indicates, is that maintaining organizational health is the most important thing you can do as a leader.  I tell our team at Return Path  all the time that our culture is a competitive advantage in many ways, some quantifiable, and others a little less tangible.

A telling point in the book is when Lencioni is relaying a conversation he had with the CEO of a client company who does run a healthy organization – he asked, “Why in the world don’t your competitors do any of this?” And the client responded, “You know, I honestly believe they think it’s beneath them.” Lencioni goes on to say, “In spite of its undeniable power, so many leaders struggle to embrace organizational health because they quietly believe they are too sophisticated, too busy, or too analytical to bother with it.”  And there you have it.  More examples of why “the soft stuff” is mission critical.

Lencioni’s “Recipe for Organizational Health” (the outline of the book):

–          Build a Cohesive Leadership Team

–          Create Clarity

–          Overcommunicate Clarity

–          Reinforce Clarity

And his recipe for creating a tight set of “mission/vision/values” (the middle of the book):

1. Why do we exist?

2. How do we behave?

3. What do we do?

4. How will we succeed?

5. What is most important, right now?

6. Who must do what?

While there are lots of other good frameworks for doing all of this, Lencioni’s models and books are great, simple reminders of one of the CEO’s most important leadership functions.  We’re recrafting our own mission and values statements at the moment at Return Path, and we’re doing it using this 6-Question framework instead of the classic “Mission/Vision/Values” framework popularized a few years back by Harvard Business Review.

The full book series roundup as far as OnlyOnce has gotten so far is:

• The Three Signs of a Miserable Job (post, book)
• The Five Temptations of a CEO (post, book)
• The Four Obsessions of an Extraordinary Executive (post, book)
• Death by Meeting (post, book)
• The Five Dysfunctions of a Team (post, book, Field Guide)
• Silos, Politics and Turf Wars (post, book)
• Getting Naked (post, book)
• The Advantage (book)

How Do You Eat an Elephant?

Credit to my colleague Chuck Drake for this one…but How Do You Eat an Elephant?  One Bite at a Time.  The David Allen school of time management (post, book)  talks about breaking your projects down into “Next Actions” so they don’t become overwhelming and can easily move forward one step at a time.

I think the same is true of organizational projects – perhaps even more so.  Any time we find ourselves swirling around a big initiative at Return Path, we are at our best when we ask ourselves some questions along these lines:

• How can we be scrappier about this?
• It it ok to be messy here…or at least not perfect?
• What is the next milestone?
• What else needs to be done until we learn the likely outcome?

We had a great example of this recently around rolling out a new product to our sales and service team.  The team is now pretty large – over 100 globally.  It was a daunting task to try to get all those people trained up at once.  The answer?  We took a bite out of the elephant.  We picked a couple of sales reps and a couple of account managers and started by training them on the new product.  Now we can figure out how to institutionalize learnings from the limited roll-out and figure out the next step from there.  Much easier than what otherwise would have been a pretty high-stakes project without enough learnings behind it, even though it will take a little longer and be a little messier.