Book Short:  Scrum ptious 

I just finished reading Scrum: The Art of Doing Twice the Work in Half the Time, by Jeff Sutherland and JJ Sutherland. This reading was in anticipation of an Agile Facilitation training my executive team and I are going through next week, as part of Return Path’s  Agile Everywhere initiative. But it’s a book I should’ve read along time ago, and a book that I enjoyed.

Sutherland gets credit for creating the agile framework and bringing the concept scrum to software development over 20 years ago. The book very clearly lays out not just the color behind the creation of the framework, and the central tenets of practice again, but also clear and simple illustrations of its value and benefits.  And any book that employs the Fibonacci series and includes Theodore Roosevelt’s “Man in the Arena” quote — my all-time favorite — is off to a good start by me.

I’ve always appreciated a lot of the underlying philosophy of Agile, such as regularly checking on projects, course correcting in response to feedback from customers or other stakeholders, and working hard to remove any impediments to progress in real time.

One of the author’s most poignant points is that “multitasking makes you stupid.”  I hadn’t focused in the past how agile allows you to clear away context shifts to focus on one task at a time, but that’s another great take away from the book.

Our Agile Everywhere initiative, which is designed to improve productivity across the organization, as well as increase accountability through transparency, is even more critical in my view after having read this book.

The thing that I am left struggling with, which is still very much a work in progress for us, and hopefully something that we will address more head on in our training next week, is the application of the agile framework to teams that are not involved in the production of a tangible work product, such as executive or other leadership teams.  That is something that our Agile Everywhere deployment team has developed a theory about, but it still hasn’t entirely sunk in for me.

I can’t wait for next week’s training session!  If you have any experience applying the agile framework to different types of teams in your company I’d love to hear more about it in the Comments.

One of the things I’ve learned over the years is that as the organization scales, you have to be all-in, until you’re not.  What the heck does that mean?

It means that, other than confiding your indecision to a very small number of trusted advisors on a given issue, indecision is poison to the people around you and to the organization in general.  So even if you’re thinking of doing something new or different or making a tough call on something, you generally need to project confidence until you’ve made the call.

One example of this is around a decision to fire someone on the team, especially a senior executive.  Public indecision about this reminds me of years ago when George Steinbrenner owned the Yankees.  Every time he contemplated firing a manager, which was often, he was very public about it.  It turned the manager into a lame duck, ignored by players and mocked by the press.  No good for the manager or for the players, unhelpful for the team as a whole.  It’s the same in business.  Again, other than a small group of trusted advisors, your people have to have your full backing until the moment you decide to remove them.

Another example of this is a shift in strategy.  Strategy drives execution – meaning the course you chart translates into the goals and activities of all the other people in your organization.  Mobilizing the troops is hard enough in the first place, and it requires a tremendous amount of leadership expressing commitment.  If you’re contemplating a shift in strategy, which of course happens a lot in dynamic businesses, and you share your thinking and qualms broadly, you risk paralyzing the organization or redirecting activities and goals without intending to or without even knowing it.

Some people might look at this concept and cry “foul – what about Transparency?”  I don’t buy that.  As I wrote recently in The Difference Between Culture and Values, “When you are 10 people in a room, Transparency means you as CEO may feel compelled to share that you’re thinking about pivoting the product, collect everyone’s point of view on the subject, and make a decision together. When you are 100 people, you probably wouldn’t want to share that thinking with ALL until it’s more baked, you have more of a concrete direction in mind, and you’ve stress tested it with a smaller group, or you risk sending people off in a bunch of different directions without intending to do so. When you are 1,000 employees and public, you might not make that announcement to ALL until it’s orchestrated with your earnings call, but there may be hundreds of employees who know by then. A commitment to Transparency doesn’t mean always sharing everything in your head with everyone the minute it appears as a protean thought.  At 10 people, you can tell everyone why you had to fire Pat – they probably all know, anyway.  At 100 people, that’s unkind to Pat.  At 1,000, it invites a lawsuit.”

The Difference Between Culture and Values

This topic has been bugging me for a while, so I am going to use the writing of this post as a means of working through it. We have a great set of core values here at Return Path. And we also have a great corporate culture, as evidenced by our winning multiple employer of choice awards, including being Fortune Magazine’s #2 best medium-sized workplace in America.

But the two things are different, and they’re often confused. I hear statements all the time, both here and at other companies, like “you can’t do that — it’s not part of our culture,” “I like working there, because the culture is so great,” and “I hope our culture never changes.”  And those statements reveal the disconnect.

Here’s my stab at a definition.  Values guide decision-making and a sense of what’s important and what’s right.  Culture is the collection of business practices, processes, and interactions that make up the work environment.

A company’s values should never really change. They are the bedrock underneath the surface that will be there 10 or 100 years from now.  They are the uncompromising core principles that the company is willing to live and die by, the rules of the game. To pick one value, if you believe in Transparency one day, there’s no way the next day you decide that being Transparent is unimportant. Can a value be changed?  I guess, either a very little bit at a time, slowly like tectonic plates move, or in a sharp blow as if you deliberately took a jackhammer to stone and destroyed something permanently.  One example that comes to mind is that we added a value a couple years back called Think Global, Act Local, when we opened our first couple of international offices.  Or a startup that quickly becomes a huge company might need to modify a value around Scrappiness to make it about Efficiency.  Value changes are few and far between.

If a company’s values are its bedrock, then a company’s culture is the shifting landscape on top of it. Culture is the current embodiment of the values as the needs of the business dictate. Landscapes change over time — sometimes temporarily due to a change in seasons, sometimes permanently due to a storm or a landslide, sometimes even due to human events like commercial development or at the hand of a good gardener.

So what does it mean that culture is the current embodiment of the values as the needs of the business dictate?  Let’s go back to the value of Transparency. When you are 10 people in a room, Transparency means you as CEO may feel compelled to share that you’re thinking about pivoting the product, collect everyone’s point of view on the subject, and make a decision together. When you are 100 people, you probably wouldn’t want to share that thinking with ALL until it’s more baked, you have more of a concrete direction in mind, and you’ve stress tested it with a smaller group, or you risk sending people off in a bunch of different directions without intending to do so. When you are 1,000 employees and public, you might not make that announcement to ALL until it’s orchestrated with your earnings call, but there may be hundreds of employees who know by then. A commitment to Transparency doesn’t mean always sharing everything in your head with everyone the minute it appears as a protean thought.  At 10 people, you can tell everyone why you had to fire Pat – they probably all know, anyway.  At 100 people, that’s unkind to Pat.  At 1,000, it invites a lawsuit.

Or here’s another example.  Take Collaboration as a value.  I think most people would agree that collaboration managed well means that the right people in the organization are involved in producing a piece of work or making a decision, but that collaboration managed poorly means you’re constantly trying to seek consensus.  The culture needs to shift over time in order to make sure the proper safeguards are in place to prevent collaboration from turning into a big pot of consensus goo – and the safeguards required change as organizations scale.  In a small, founder-driven company, it often doesn’t matter as much if the boss makes the decisions.  The value of collaboration can feel like consensus, as they get to air their views and feel like they’re shaping a decision, even though in reality they might not be.  In a larger organization with a wider range of functional specialists managing their own pieces of the organization, the boss doesn’t usually make every major decision, though guys like Ellison, Benioff, Jobs, etc. would disagree with that.  But in order for collaboration to be effective, decisions need to be delegated and appropriate working groups need to be established to be clear on WHO is best equipped to collaborate, and to what extent.  Making these pronouncements could come as feeling very counter-cultural to someone used to having input, when in fact they’re just a new expression of the same value.

I believe that a business whose culture never evolves slowly dies.  Many companies are very dynamic by virtue of growth or scaling, or by being in very dynamic markets even if the company itself is stable in people or product. Even a stable company — think the local hardware store or barber shop — will die if it doesn’t adapt its way of doing business to match the changing norms and consumption patterns in society.

This doesn’t mean that a company’s culture can’t evolve to a point where some employees won’t feel comfortable there any longer. We lost our first employee on the grounds that we had “become too corporate” when we reached the robust size of 25 employees. I think we were the same company in principles that day as we had been when we were 10 people (and today when we are approaching 500), but I understood what that person meant.

My advice to leaders: Don’t cling to every aspect of the way your business works as you scale up. Stick to your core values, but recognize that you need to lead (or at least be ok with) the evolution of your culture, just as you would lead (or be ok with) the evolution of your product. But be sure you’re sticking to your values, and not compromising them just because the organization scales and work patterns need to change.  A leader’s job is to embody the values.  That impacts/produces/guides culture.  But only the foolhardy leaders think they can control culture.

My advice to employees: Distinguish between values and culture if you don’t like something you see going on at work. If it’s a breach of values, you should feel very free to wave your arms and cry foul. But if it’s a shifting of the way work gets done within the company’s values system, give a second thought to how you complain about it before you do so, though note that people can always interpret the same value in different ways.  If you believe in your company’s values, that may be a harder fit to find and therefore more important than getting comfortable with the way those values show up.

Note:  I started writing this by talking about the foundation of a house vs. the house itself, or the house itself vs. the furniture inside it.  That may be a more useful analogy for you.  But hopefully you get the idea.

Book Short:  Continuing to make “sustainability” a mainstream business topic

The Big Pivot: Radically Practical Strategies for a Hotter, Scarcer, and More Open World, by my friend Andrew Winston, is a great book.  It just got awarded one of the Top 10 business books of 2014 by Strategy+Business, which is a great honor.

Andrew builds nicely on his first book, Green to Gold:  How Smart Companies Use Environmental Strategy to Innovate, Create Value, and Build Competitive Advantage (post, book link) (and second book, which I didn’t review, Green Recovery), as I said in my review of Green to Gold, to bring:

the theoretical and scientific to the practical and treat sustainability as the corporate world must treat it in order to adopt it as a mainstream practice — as a driver of capitalistic profit and competitive advantage.

Andrew’s central thesis, with plenty of proof points in the book for our planet of 7 Billion people, rapidly heading to 9-10 Billion, is this:

Whether you take a purely fiscal view of these challenges or look through a human-focused lens, one thing is clear: we’ve passed the economic tipping point. A weakening of the pillars of our planetary infrastructure— a stable climate, clean air and water, healthy biodiversity, and abundant resources— is costing business real money. It’s not some futuristic scenario and model to debate, but reality now, and it threatens our ability to sustain an expanding global economy… If this hotter, scarcer, more transparent, and unpredictable world is the new normal, then how must companies act to ensure a prosperous future for all, including themselves?

Andrew’s writing is accessible and colorful.  The book is full of useful analogies and metaphors like this one:

Climate can also seem easy to write off because the warming numbers don’t sound scary. A couple degrees warmer may sound pleasant, but we’re not really talking about going from 75 to 77 degrees Fahrenheit on a nice spring day. As many others have pointed out, the right metaphor is a fever. Take your core body temperature up one degree, and you don’t feel so great. Five degrees, and you’re sick as a dog. Ten degrees, and you’re dead.

The book also does a really nice job of looking at the externalities of climate change in a different way.  Not the usual “I can pollute, because there’s no cost to me to doing so,” but more along the lines of “If I had to pay for all the natural resources my business consumes, I would treat them differently.”

Some of Andrew’s points are good but general and maybe better made elsewhere (like the problems of short-termism on Wall Street), but overall, this book is a great think piece for all business leaders, especially in businesses that consume a lot of natural resources, around how to make the challenge of climate change work for your business, not against it.

Two things occurred to me during my read of The Big Pivot that I think are worth sharing for the people in my life who still don’t believe climate change is real or threatening.  The first is Y2K.  Remember the potentially cataclysmic circumstance where mission critical systems all around the world were going to go haywire at midnight at the turn of the millennium?  The conventional wisdom on why nothing major went wrong is that society did enough work ahead of time to prevent it, even though the outcomes weren’t clear and no one system problem alone would have been an issue.  I was thinking about this during the book…and then Andrew mentioned it explicitly towards the end.

The second is something I read several years ago in my personal news bible, The Economist.  I couldn’t find the exact quote online just now, but it was something to the effect of “Even if you don’t believe man created climate change, or that climate change is real and imperiling to humanity and can be fixed by man, the risks of climate change are so great, the potential consequences so dire, and the path to solve the problem so lengthy and complex and global…it’s worth investing in that solution now.”

Let’s all pivot towards that, shall we?  If you want to download the introduction to the book for free, you can find it on Andrew’s web site.  Or for a three-minute version of the story, you can watch this whiteboard animation on YouTube.

Book Short: Faster Than The Blink of an Eye

Michael Lewis is one of those authors for whom my general point of view is “read whatever he writes.” Flash Boys: A Wall Street Revolt  was no exception.  It’s a book about the high-frequency trading business, how a difference in microseconds can make a difference, and how the complexity of trading has led to enough confusion that virtually no one on Wall Street actually understands how it works any more.

I am a capitalist through and through, and I never begrudge Wall Street for making money, even though I do have moments where I doubt the amount of value that finance creates relative to the amount of income they swallow up.  However, that all goes out the window when there is evidence that some pocket of Wall Street isn’t playing by the rules.  I define “the rules” as either the law, or as something more like “a basic sense of morality and fairness.”

Some of what has been going on in the high-frequency trading business, as Lewis describes in this book, may or may not be legal (let’s assume it is), but is almost certainly not following a basic sense of morality and fairness.  It’s worth noting that I am purely going off what Lewis wrote in the book, so to the extent that his research is incomplete or his writing is misleading, I am happy to retract that statement.  But based on what I read, I’d challenge some of the people in the HFT business to defend what they’re doing publicly, to their mothers or to their own clients.  That’s the ultimate test of morality or fairness.

It’s amazing to me that this topic hasn’t gotten more play in the media or with regulators.  Maybe it’s just too complicated for anyone to understand or to articulate.  In any event, even though not strictly a business book, it’s fascinating and worth a read, as I think all Michael Lewis books are.

Book Short:  Like Reading a Good Speech

Leaders Eat Last, by Simon Sinek, is a self-described “polemic” that reads like some of the author’s famous TED talks and other speeches in that it’s punchy, full of interesting stories, has some attempted basis in scientific fact like Gladwell, and wanders around a bit.  That said, I enjoyed the book, and it hit on a number of themes in which I am a big believer – and it extended and shaped my view on a couple of them.

Sinek’s central concept in the book is the Circle of Safety, which is his way of saying that when people feel safe, they are at their best and healthiest.  Applied to workplaces, this isn’t far off from Lencioni’s concept of the trust foundational layer in his outstanding book, Five Dysfunctions of a Team.  His stories and examples about the kinds of things that create a Circle of Safety at work (and the kinds of things that destroy them) were very poignant.  Some of his points about how leaders set the tone and “eat last,” both literally and figuratively, are solid.  But his most interesting vignettes are the ones about how spending time face-to-face in person with people as opposed to virtually are incredibly important aspects of creating trust and bringing humanity to leadership.

My favorite one-liner from the book, which builds on the above point and extends it to a corporate philosophy of people first, customer second, shareholders third (which I have espoused at Return Path for almost 15 years now) is

Customers will never love a company unless employees love it first.

A couple of Sinek’s speeches that are worth watching are the one based on this book, also called Leaders Eat Last, and a much shorter one called How Great Leaders Inspire Action.

Bottom line:  this is a rambly book, but the nuggets of wisdom in it are probably worth the exercise of having to find them and figure out how to connect them (or not connect them).

Thanks to my fellow NYC CEO Seth Besmertnik for giving me this book as well as the links to Sinek’s speeches.

Secrets to Yawn-Free Board Meetings

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

The objective of board meetings should always be to have great conversations that help you and your executive team think clearly about the issues in front of you, as well as making sure your directors have a clear and transparent view of the state of the business. These conversations come from a team dynamic that encourages productive conflict. There’s no sure-fire formula for achieving this level of engagement, but here are three few guidelines you can follow to increase your chances.

Schedule board meetings in advance, and forge a schedule that works. Nothing is more disruptive – or more likely to drive low turnout – than last minute scheduling. Make sure you, or your executive assistant, knows board members’ general schedules and travel requirements, and whether they manage their own calendar or have their own executive assistant. Set your board meeting schedule for the year in the early fall, which is typically when people are mapping out most of their year’s major activities. If you know that one of your board members has to travel for your meetings, work with the CEOs of the other companies to coordinate meeting dates. Vary the location of meetings if you have directors in multiple geographies so travel is a shared sacrifice.

In the startup stage of our business at Return Path, we ran monthly meetings for an hour, mostly call-in. In the revenue stage, we moved to six to eight meetings per year, two hours in length, perhaps supplemented with two longer-form and in-person meetings. As a growth stage company, we run quarterly meetings. They’re all in-person, meaning every director is expected to travel to every meeting. We probably lose one director each time to a call-in or a no-show for some unavoidable conflict, but, for the most part, everyone is present. We leave four hours for every meeting (it’s almost impossible to get everything done in less time than that) and sometimes we need longer.

Many years, we also hold a board offsite, which is a meeting that runs across 24 hours, usually an afternoon, a dinner, and a morning, and is geared to recapping the prior year and planning out the next year together. It’s especially exhausting to do these meetings, and I’m sure it’s especially exhausting to attend them, but they’re well worth it. The intensity of the sessions, discussion, and even social time in between meetings is great for everyone to get on the same page and remember what’s working, what’s not, and what the world around us looks like as we dive into the deep end for another year.

Build a forward-looking agenda. The second step in having great board meetings is to set an agenda that will prompt the discussion that you want to have. With our current four-hour meetings, our time allocation is the following:

I. Welcomes and framing (5 minutes)

II. Official Business (no more than 15 minutes unless something big is going on)

III. Retrospective (45 minutes)

a. Target a short discussion on highlighted issues

b. Leave some time for Q&A

IV. On My Mind (2 hours)

a. You can spend this entire time on one topic, more than one, or all, as needed.

b. Format for discussions can vary—this is a good opportunity for breakout sessions, for example.

V. Executive Session (30 minutes)

This is your time with directors only, no observers or members of the management team (even if they are board members).

VI. Closed Session (30 minutes)

This is director-only time, without you or anyone else from the management team.

This agenda format focuses your meeting on the future, not the past. In the early years of the business, our board meetings were probably 75 percent “looking backwards” and 25 percent “looking forwards.” They were reporting meetings—reports which were largely in the hands of board members before the meetings anyway. They were dull as anything, and they were redundant: all of our board members were capable of processing historical information on their own. Today, our meetings are probably ten percent “looking backwards” and 90 percent “looking forwards”—and much more interesting as a result.

Separate background reading and presentation materials. Finally, focus on creating a more engaging dialogue during the meeting by separating background reading from presentation materials. In our early days, we created a huge Powerpoint deck as both a handout the week before the meeting and as the in-meeting deck. That didn’t create an engaging meeting.

There’s nothing more mind-numbing than a board meeting where the advance reading materials are lengthy Powerpoint presentations, than when the meeting itself is a series of team members standing up and going through the same slides, bullet by excruciating bullet—that attendees could read on their own.

When we separated the background and presentation materials, people were engaged by the Powerpoint—because it delivered fresh content. We started making the decks fun and engaging and colorful, as opposed to simple text and bullet slides. That was a step in the right direction, but the preparation consumed twice as much time for the management team, and we certainly didn’t get twice the value from it.

Now we send out a great set of comprehensive reading materials and reports ahead of the meeting, and then we have a completely Powerpoint-free meeting. No slides on the wall. This changes the paradigm away from a presentation—the whole concept of “management presenting to the board”—to an actual discussion. No checking email. No yawns. Nobody nodding off. Everyone—management and board—is highly engaged

Getting the Most out of Your Investors

Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  The first two posts were mine on selecting investors and Fred’s on selecting investments.  This is my second one…and Fred’s post on the other side of the topic is here.

Once you’ve done a venture financing and the smoke clears, you have to transition the relationship you have with your new investor from the courting phase to building a CEO-Director relationship for the long haul.  Here are a few thoughts on how best to do optimize the relationship once it’s established.

1. Take onboarding seriously.  I always say that the hiring process for new employees doesn’t end when the employee starts…it ends 90 days later after some deliberate onboarding and a two-way review to check in and see how things are going.  Adding a new Board member is the same.  Onboard him or her with some of the same rigor and materials with which you’d onboard a new executive.  Touch base a lot early on.  Schedule an in-person 1:1 check-in after a few months to see how things are going
2. Give news early and often.  CEOs who wait until Board meetings to share all news are missing out on the point of a good director relationship, as well as missing the point of how communications work in the 2010s.  This is especially true with bad news.  No one likes to get it, but the earlier people hear it, the more they can thoughtfully process it and provide help
3. Ask for and give feedback early and often.  Though there are certainly some exceptions, venture investors are notoriously bad about giving and receiving feedback.  If you set the tone by asking for feedback regularly – then being sure to internalize and act on it and check back in to see if improvements are obvious – you can get even the most reticent director to speak up.  And there’s no reason you shouldn’t be providing feedback in near-real time as well.  Just because a director is your boss doesn’t mean he or she is meeting your expectations, and it’s a partnership, not a true hierarchical relationship
4. Ask for help and give assignments.  As a friend of mine says to her kids all the time, You don’t A-S-K, you don’t G-E-T.  If Board members don’t have specific things to work on, they either do nothing, or they do things you don’t need help on.  Drive the work like you would with any team member
5. Foster independent relationships with your team and other directors.  The hourglass model – where the CEO sits in between the Board and the management team and filters all dialog and data from one group to the other – is outdated.  A director will be much more able to add value to you and to the organization if he or she has an independent point of view as to what’s going on with your team and what other directors are thinking
6. Encourage directors to speak their minds.  As awful as company politics are, Board politics are worse.  Try to create an environment where directors aren’t shy about saying what’s really on their mind.  You don’t want to get through a Board meeting and then have someone pull you aside and say “what I really think is…”  This means you need to ask them direct questions, not be defensive in your verbal or body-language reaction, and make sure you allow for Executive Sessions at Board meetings
7. Hold directors accountable.  If you give a Board member an assignment, make sure it gets done on time and the way you asked for it.  If you have a director who is sitting in your Board meetings doing email the whole time, politely (and maybe privately, at least the first time) call him out on it.  If you don’t hold directors accountable, then just like your staff, they will learn that you don’t really mean what you say
8. Use their time wisely.  No one likes to waste time – certainly not professional investors who sit on a dozen boards.  Get Board materials out early, run productive Board meetings, and while you include some social element like a dinner or outing, make sure even that has the right group and is at the right kind of venue
9. Augment the Board with independent directors.  Venture directors can be amazingly helpful resources for you and your company.  But they typically have limitations as to their range of operating experience.  If you want to build a great Board and add some counterweights to your VCs, add one or more independent directors who are experienced business operators with experience serving on Boards as well

Year ago when we both first started blogging, Fred and I wrote a whole series of Venture Cliché and Counter-Cliché posts.  Writing these two makes me realize how much fun that was!  I’m looking forward to the class at Princeton next week and to seeing the kinds of questions these four posts inspire.

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.

Stamina

A couple years ago I had breakfast with Nick Mehta, my friend who runs the incredibly exciting Gainsight.  I think at the time I had been running Return Path for 15 years, and he was probably 5 years into his journey.  He said he wanted to run his company forever, and he asked me how I had developed the stamina to keep running Return Path as long as I had.  My off the cuff answer had three points, although writing them down afterwards yielded a couple more.  For entrepreneurs who love what they do, love running and building companies for the long haul, this is an important topic.  CEOs have to change their thinking as their businesses scale, or they will self implode!  What are five things you need to get comfortable with as your business scales in order to be in it for the long haul?

Get more comfortable with not every employee being a rock star.  When you have 5, 10, or even 100 employees, you need everyone to be firing on all cylinders at all times.  More than that, you want to hire “rock stars,” people you can see growing rapidly with their jobs.  As organizations get larger, though, not only is it impossible to staff them that way, it’s not desirable either.  One of the most influential books I’ve read on hiring over the years, Topgrading (review, buy), talks about only hiring A players, but hiring three kinds of A players:  people who are excellent at the job you’re hiring them for and may never grow into a new role; people who are excellent at the job you’re hiring them for and who are likely promotable over time; and people who are excellent at the job you’re hiring them for and are executive material.  Startup CEOs tend to focus on the third kind of hire for everyone.  Scaling CEOs recognize that you need a balance of all three once you stop growing 100% year over year, or even 50%.

Get more comfortable with people quitting.  This has been a tough one for me over the years, although I developed it out of necessity first (there’s only so much you can take personally!), with a philosophy to follow.  I used to take every single employee departure personally.  You are leaving MY company?  What’s wrong with you?  What’s wrong with me or the company?  Can I make a diving catch to save you from leaving?  The reality here about why people leave companies may be 10% about how competitive the war for talent has gotten in technology.  But it’s also 40% from each of two other factors.  First, it’s 40% that, as your organization grows and scales, it may not be the right environment for any given employee any more. Our first employee resigned because we had “gotten too big” when we had about 25 employees.  That happens a bit more these days!  But different people find a sweet spot in different sizes of company.  Second, it’s 40% that sometimes the right next step for someone to take in their career isn’t on offer at your company.  You may not have the right job for the person’s career trajectory if it’s already filled, with the incumbent unlikely to leave.  You may not have the right job for the person’s career trajectory at all if it’s highly specialized.  Or for employees earlier in their careers, it may just be valuable for them to work at another company so they can see the differences between two different types of workplace.

Get more comfortable with a whole bunch of entry level, younger employees who may be great people but won’t necessarily be your friends.  I started Return Path in my late 20s, and I was right at our average age.  It felt like everyone in the company was a peer in that sense, and that I could be friends with all of them.  Now I’m in my (still) mid-40s and am well beyond our average age, despite my high level of energy and of course my youthful appearance.  There was a time several years ago where I’d say things to myself or to someone on my team like “how come no one wants to hang out with me after work any more,” or “wow do I feel out of place at this happy hour – it’s really loud here.”  That’s all ok and normal.  Participate in office social events whenever you want to and as much as you can, but don’t expect to be the last man or woman standing at the end of the evening, and don’t expect that everyone in the room will want to have a drink with you.  No matter how approachable and informal you are, you’re still the CEO, and that office and title are bound to intimidate some people.

Get more comfortable with shifts in culture and differentiate them in your mind from shifts in values.  I wrote a lot about this a couple years ago in The Difference Between Culture and Values . To paraphrase from that post, an organization’s values shouldn’t change over time, but its culture – the expression of those values – necessarily changes with the passage of time and the growth of the company.  The most clear example I can come up with is about the value of transparency and the use case of firing someone.  When you have 10 employees, you can probably just explain to everyone why you fired Joe.  When you have 100 employees, it’s not a great idea to tell everyone why you fired Joe, although you might be ok if everyone finds out.  When you have 1,000 employees, telling everyone why you fired Joe invites a lawsuit from Joe and an expensive settlement on your part, although it’s probably ok and important if Joe’s team or key stakeholders comes to understand what happened.  Does that evolution mean you aren’t being true to your value of transparency?  No.  It just means that WHERE and HOW you are transparent needs to evolve as the company evolves.

• Get more comfortable with process.  This doesn’t mean you have to turn your nimble startup into a bureaucracy.  But a certain amount of process (more over time as the company scales) is a critical enabler of larger groups of people not only getting things done but getting the right things done, and it’s a critical enabler of the company’s financial health.  At some point, you and your CFO can’t go into a room for a day and do the annual budget by yourselves any more.  But you also can’t let each executive set a budget and just add them together.  At some point, you can’t approve every hire yourself.  But you also can’t let people hire whoever they want, and you can’t let some other single person approve all new hires either, since no one really has the cross-company view that you and maybe a couple of other senior executives has.  At some point, the expense policy of “use your best judgment and spend the company’s money as if it was your own” has to fit inside department T&E budgets, or it’s possible that everyone’s individual best judgments won’t be globally optimal and will cause you to miss your numbers.  Allow process to develop organically.  Be appropriately skeptical of things that smell like bureaucracy and challenge them, but don’t disallow them categorically.  Hire people who understand more sophisticated business process, but don’t let them run amok and make sure they are thoughtful about how and where they introduce process to the organization.

I bet there are 50 things that should be on this list, not 5.  Any others out there to share?

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.