To Err is Human, To Admit it is Divine

Forget about forgiveness.  Admitting mistakes is much harder.  The second-to-last value that I’m writing up of our 13 core values at Return Path is

We don’t want you to be embarrassed if you make a mistake; communicate about it and learn from it

People don’t like to feel vulnerable.  And there’s no more vulnerable feeling in business than publicly acknowledging that you goofed, whether to your peers, your boss, or your team (hard to say which is worse — eating crow never tastes good no matter who is serving it). But wow is it a valuable trait for an organization to have. Here are the benefits that come from being good at admitting mistakes:

• You’re not afraid to MAKE mistakes in the first place.  Taking risks, which is one of the things that vaults businesses forward with great speed, inherently involves making mistakes. If you’re afraid to shoot…you can’t score
• You teach yourself not to make the same mistake twice.  Being public about mistakes you make really reinforces your leanings.  It’s sort of like taking notes in class.  If you write it down, you’re more likely to remember it, even if you’re a good listener to the teacher
• You teach others not to make the same mistake you made.  Not everyone learns from the mistakes of others as opposed to the mistakes of self, but being public about mistakes and learnings at least gives other people a shot at learning

We’ve gotten good over the years at doing post-mortems (which I wrote about here) when a major snafu happens, which is institutional (large scale) admission and learning. But smaller scale post-mortems within a team and with less formal process around them are just as important if not more so, to make them commonplace.

We have also baked this thinking into our entire product development process.  We are as lean and agile as possible given that we are closing in on 300 employees now in 11 offices in 8 countries.  Our entire product development process is now geared around the concept of “fail fast” and killing projects or sending them back to the drawing board when they’re not meeting marketplace demand.  Embracing this posture has been one of the hallmarks of our success as we’ve scaled the business these past few years.

One trick here:  If this is something you are trying to institutionalize in your company — make sure you celebrate the admission of a mistake and the learnings from it, rather than the mistake itself. You do still value successful execution more than most things!

I’ve written a few times over the years about our Sabbatical policy at Return Path, including this post and this post about my experience as CEO when one of my direct reports was on his sabbatical, and this post about my own sabbatical.

People ask me this all the time, so I thought I’d write the policy out here.  This is the language in our employee handbook about them:

You have big dreams. We know. This is your chance to cross something off your life list. Whether it’s climbing Mt. Everest, learning Russian or taking your kids across the country in a Winnebago, we believe in rewarding longevity at Return Path and know that a good long break will leave you refreshed and energized!  As such, you are eligible for a sabbatical after your first seven (7) years of employment; then again after every five (5) years incremental employment. The sabbatical provides you with up to six (6) weeks of consecutive time off provided you have that time off approved by your manager at least two months prior to the start of your sabbatical.

You will be requested to sign an Agreement before your sabbatical: if you do not return to work after your sabbatical or if you leave employment within twelve (12) months of returning to work, you will be required to reimburse all amounts received while on sabbatical.  If a holiday occurs on any of of the days of absence, you will not receive holiday pay in addition to your sabbatical pay.  During your sabbatical, your benefits will continue and you will be responsible for making payments for the employee portion of insurance costs if applicable. The period you are on leave will be counted as employment for the purposes of determining your applicable level of benefits.  If you are eligible and have not taken your sabbatical and your employment with Return Path ends (for any reason), you will not be paid out for sabbatical time not taken.

I also wrote an email recently to someone internally that is worth reprinting here, which is How to Prepare for Your Sabbatical, which is aimed at both the person taking the sabbatical, and the person’s manager:

As the employee:

–          Prepare your team

• Make sure their goals and metrics for your time out are super clear
• Make sure they know who to go to for what
• Set their expectations of management coverage (see below). 
• Remember that your manager has a day job so you should look to see how your team members can take over some of the responsibilities.
• Give them stretch goals while you’re out

–          Prepare your individual contributor work

• Hand off all loose ends with extra details. 
• Make introductions via email if your manager/team member  is going to have to work with external parties
• Can be to your team, to your manager, to someone else

–          Prepare your manager

• Brief your manager thoroughly on everything going on with your team, its work, your individual contributor work
• Good topics to cover with your manager:Discuss specifics of team and 1:1 check-ins and agree on a plan for coverage.
  • What are the big initiatives that you’ll need coverage on
  • Which team members would you like the manager to spend a little extra time with?  Are there any work you would like the manager to help a particular EE with?

–          Prepare yourself

• Plan any personal travel early so you get good rates!
• Figure out how to keep your work and personal communications separate – your email (autoresponder, routing, disabling from your smartphone), your voicemail if you use Google Voice or Simulscribe, etc.
• Block out two full days immediately when you return to catch up on email and catch up with your manager and team

As the manager:

–          Prepare your team

• Make sure the rest of your team knows your time will be compromised while you’re covering
• Figure out what kind of coverage you need (either internal or external) while you’re covering

–          Rearrange your calendar/travel

• Add new team meetings or 1:1s as it makes sense.  You don’t have to do exactly what your employee did, but some portions of it will make sense to pick up
• If your employee works in another office with members of his/her team, you might want to plan some travel there to cover in person
• It’s ok to cut back on some other things a bit while you’re covering – just remember to undo everything when the employee’s sabbatical is over

–          While you’re in charge

• Surprise your employee with how much you were able to keep things running in his/her absence!
• Learn as much as you can by doing bits and pieces of his/her job.  This is a great opportunity of the employee to get some value from a fresh perspective.

–          Prepare for your employee’s return

• Keep a running tab of everything that goes on at the company, critical industry news (if appropriate), and with your employee’s function or team and prepare a well-organized briefing document so your employee can hit the ground running when he/she returns
• Block out an hour or two each of the employee’s first two days back to review your briefing document

My main takeaway from this post?  I am overdue my second sabbatical, and it’s time to start thinking about that!

I’ve always been a big believer in the consistent application frameworks for business thinking and decision-making.  Frameworks are just a great starting point to spark conversation and organize thinking, especially when you’re faced with a new situation.  Last year, I read Tom Friedman’s new book, Thank You for Being Late: An Optimist’s Guide to Thriving in the Age of Accelerations, and he had this great line that reminded me of the power of frameworks and that it extends far beyond business decision-making:

When you put your value set together with your analysis of how the Machine works and your understanding of how it is affecting people and culture in different contexts, you have a worldview that you can then apply to all kinds of situations to produce your opinions. Just as a data scientist needs an algorithm to cut through all the unstructured data and all the noise to see the relevant patterns, an opinion writer needs a worldview to create heat and light. 

In Startup CEO, I wrote about a bunch of different frameworks we have used over the years at Return Path, from vetting new business ideas to selecting a type of capital and investor for a capital raise.  I blogged about a new one that I learned from my dad a few months ago on delegation.  One of my favorite business authors, Geoffrey Moore, has developed more frameworks than I can count and remember about product and product-market fit.

But all frameworks can go stale over time, and they can also get bogged down and confused with pattern recognition, which has limitations.  To that end, Friedman also addressed this point:

But to keep that worldview fresh and relevant…you have to be constantly reporting and learning—more so today than ever. Anyone who falls back on tried-and-true formulae or dogmatisms in a world changing this fast is asking for trouble. Indeed, as the world becomes more interdependent and complex, it becomes more vital than ever to widen your aperture and to synthesize more perspectives.

Again, although Friedman talks about this in relation to journalism, the same can be applied to business.  Take even the most basic framework, the infamous BCG “Growth/Share Matrix” that compares Market Growth and Market Share and divides your businesses into Dogs, Cash Cows, Question Marks, and Stars.  Digital Marketing has disrupted some of the core economics of firms, so there are a number of businesses that you might previously have said were in the Dog quadrant but due to improved economics of customer acquisition can either be moved into Cash Cow or at least Question Mark.  Or maybe the 2×2 isn’t absolute any more, and it now needs to be a 2×3.

The business world is dynamic, and frameworks, ever important, need to keep pace as well.

We’ve been in business at Return Path for almost 18 years now.  We’ve seen a number of competitors come and go across a bunch of different related businesses that we’ve been in.  One of the things I’ve noticed and never quite understood is that many of our competitors expend a lot of time and energy publicly trash talking us in the market.  Sometimes this takes the form of calling us or our products out by name in a presentation at a conference; other times it takes the form of a blog post; other times it’s just in sales calls.  It’s weird.  You don’t see that all that often in other industries, even when people take aim at market leaders.

During the normal course of business, one of sales reps might engage in selling against specific competitors — often times, they have to when asked specific questions by specific prospects — but one thing you’ll never see us do is publicly trash talk a single competitor by name as a company.  I’m sure there are a couple people at Return Path who would like us to have “sharper elbows” when it comes to this, but it’s just not who we are.  Our culture is definitely one that values kindness and a softer approach.  But good business sense also tells me that it’s just not smart for four reasons:

• We’re very focused and disciplined in our outbound communications — and there’s only so much air time you get as a company in your industry, even among your customers — on thought leadership, on showcasing the value of our data and our solutions, and on doing anything we can do to make our customers more successful.  Pieces like my colleague Dennis Dayman’s recent blog post on the evolution of the data-driven economy, or my colleague Guy Hanson’s amazingly accurate prediction of the UK’s “unpredictable” election results both represent the kind of writing that we think is productive to promote our company
• We’re fiercely protective of our brand (both our employer brand and our market-facing brand), and we’ve built a brand based on trust, reputation, longevity, and being helpful, in a business that depends on reputation and trust as its lifeblood — as I think about all the data we handle for clients and strategic partners, and all the trust mailbox providers place in us around our Certification program.  Clients and partners will only place trust in — and will ultimately only associate themselves with — good people.  To quote my long time friend and Board member Fred Wilson (who himself is quoting a long time friend and former colleague Bliss McCrum), if you lie down with dogs, you come up with fleas.  If we suddenly turned into the kind of company that talked trash about competition, I bet we’d find that we had diminished our brand and our reputation among the people who matter most to us.  Our simple messaging and positioning showcases our people, our expertise, and our detailed knowledge of how email marketing works, with a collective 2,000 years of industry experience across our team
• Trash talking your competition can unwittingly expose your own weaknesses.  Think about Donald Trump’s memorable line from one of the debates against Hillary Clinton – “I’m not the puppet, you’re the puppet” – when talking about Russia.  That hasn’t turned out so well for him.  It’s actually a routine tactic of Trump, beyond that one example.  Accuse someone else of something to focus attention away from your own issues or weaknesses.  Don’t like the fact that your inauguration crowd was demonstrably smaller than your predecessor’s?  Just lie about it, and accuse the media of creating Fake News while you’re at it.  Disappointed that you lost the popular vote?  Accuse the other side of harvesting millions of illegal votes, even though it doesn’t matter since you won the electoral college!  Think about all these examples, regardless of your politics.  All of them draw attention to Trump’s weaknesses, even as he’s lashing out at others (and even if you think he’s right).  We don’t need to lash out at others because we have so much confidence in our company, our products, and our services.  We are an innovative, happy, stable, profitable, and growing vendor in our space, and that’s where our attention goes
• Publicly trash talking your competition just gives your competition extra air time.  As PT Barnum famously said, “You can say anything you want about me, just make sure you spell my name right!”

Don’t get me wrong.  Competition is healthy.  It makes businesses stronger and can serve as a good focal point for them to rally.  It can even be healthy sometimes to demonize a competitor *internally* to serve as that rallying cry.  But I am not a fan of doing that *externally.*  I think it makes you look weak and just gives your competitor free advertising.

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.

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.

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

Years ago, my co-founder Jack and I developed a training presentation to give to new employees who were not just new to Return Path but also new to the workforce.  This is another one of those things, like my last post on our sabbatical policy, that people ask me for all the time.

Bringing new people into the workforce is different from just bringing new people into an organization.  I know I got a huge amount of value in my first job in management consulting from just learning how to go to work every day and how to be successful professionally.  The process you need to go through is like Onboarding, but on steroids.

Not everyone has parents or older siblings or role models who work in business — or for that matter, who focus on any kind of workplace mentoring.  It may sound dumb, but even things like showing up on time for work, what to wear, and how to meet with your manager aren’t necessarily obvious even to smart and well-intentioned 21-year olds.

So with the caveats that it’s a little dated as is, and that it’s more relevant to the kind of company we are at Return Path (e.g., we serve business clients), here’s a SlideShare version of the presentation.

Feel free to plagiarize, customize, and share it from here if you’re interested.

Articulating the Problem is the First Step Toward Solving It

A while back, we were having some specific challenges at Return Path that were *really* hard to diagnose.  It was like peeling the proverbial onion.  Every time we thought we had the answer to what was going on, we realized all we had was another symptom, not a root cause.  We’re a pretty analytical bunch, so we kept looking for more and more data to give us answers.  And we kept coming up with, well, not all that much, besides a lot of hand-wringing.

It wasn’t until I went into a bit of a cave (e.g., took half a day’s quiet time to myself) and started writing things down for myself that I started to get some clarity around the problem and potential solutions.  I literally opened up a blank Word document and started writing, and writing, and writing.  At first, the thoughts were random.  Then they started taking on some organization.  Eventually, I moved from descriptions of the problem to patterns, to reasons, to thoughts about solutions. 

But what really put me on a track to solutions (as opposed to just understanding the problem better) was starting to *talk* through the problems and potential solutions.  It didn’t take more than a couple conversations with trusted colleagues/advisors before I realized how dumb half of my thoughts were, both about the problems and the solutions, which helped narrow down and consolidate my options considerably.

Even better than solving the problems, or at least a driver of being able to solve them, is feeling more in control of a tough situation.  That’s probably the best thing I’ve learned over the years about the value of articulating problems and solutions.  For a leader, there is no worse feeling than being out of control…and no better feeling than the opposite.  Some level of control or confidence is required to get through tough times.

I suppose this post is not all that different from any 12-step program.  First, admit you have a problem.  Then you can go on to solve it.  But the point I am trying to make is more than that – it’s not just admitting you have a problem.  It’s actually diving in deep to the potential causes of the problem, and writing them down and (better) speaking them out loud a few times, that puts you on the road to solving those problems.

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.