I gave a presentation to a few hundred Return Path employees in January at an all-hands conference we did called “How to Manager Your Career.”

The presentation has three sections — The Three Phases of a Career, How to Get Promoted, and How to Wow Your Manager.

While it’s not as good without the voiceover and interactivity, I thought I’d post it here…see the presentation on Slideshare.

As I said to my audience, if there’s one thing to take away from the topic, it’s this:

Managing your career is up to one, and only one person – you. 

It doesn’t matter how great a corporate culture you have, or how supportive your manager is.  You’re the only person who cares 100% of the time about your career, and you’re the only person with a longitudinal view of what you love, what you’re great at, where you’ve been, and where you want to go.

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.

Return Path’s Newest Board Member: Jeff Epstein

I’ve written before about how much I love my Board. Well, I’m pleased to announce I have a new reason to love it – today, I’m officially welcoming Jeff Epstein to the Return Path Board of Directors. He is joining an all-star cast that includes Greg Sands, Fred Wilson, Brad Feld, Scott Weiss and Scott Petry.

I first met Jeff back in 2000 when, as CFO of DoubleClick, he and DoubleClick CEO Kevin Ryan agreed to invest in Return Path as our first institutional investor, along with Flatiron Partners.  He is one of the few people who have seen the company grow from its infancy to today.  Jeff has been a formal advisor to the company for more than a year, and he recently agreed to join as a director.

Jeff has all the qualities that make for an awesome board member and he’s already been an influential voice with uncommon insight and an impressive background that complements the rest of our board. As CFO of Oracle Jeff helped guide one of the world’s preeminent technology companies. He’s also served as CFO for large private and public companies including DoubleClick, King World Productions, and Neilsen’s Media Measurement and Information Group, and is a member of the boards of Priceline.com, Kaiser Permanente, Shutterstock, and the Management Board of the Stanford Graduate School of Business. Jeff is currently a partner at Bessemer Venture Partners and a senior advisor at Oak Hill Capital.

Building and managing a board of directors is one of the key functions of a CEO, and the entire Return Path team benefits from a close relationship with great industry leaders. Jeff’s appointment is a perfect example. He’s steered successful organizations through many of the same decisions and challenges that we’re facing. He evaluates issues from multiple points of view – as a senior executive, as a board member, as an investor. And he’s not quiet. On our board, that’s essential. We’re a group of strong personalities—we challenge ideas, we analyze everything, and our views don’t always have to agree.

I’ve said that one secret to running an effective board is to ask for members’ opinions only when you want them. In Jeff’s case I definitely want them. So, on behalf of the board and the entire team at Return Path, Jeff, welcome!

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.

The Value of Paying Down Technical Debt

Our Engineering team has a great term called Technical Debt, which is the accumulation of coding shortcuts and operational inefficiencies over the years in the name of getting product out the door faster that weighs on the company’s code base like debt weighs on a balance sheet.  Like debt, it’s there, you can live with it, but it is a drag on the health of the technology organization and has hard servicing costs.  It’s never fun to pay down technical debt, which takes time away from developing new products and new features and is not really appreciated by anyone outside the engineering organization.

That last point is a mistake, and I can’t encourage CEOs or any leaders within a business strongly enough to view it the opposite way.  Debt may not be fun to pay off, but boy do you feel better after it’s done.  I attended an Engineering all-hands recently where one team presented its work for the past quarter.  For one of our more debt-laden features, this team quietly worked away at code revisions for a few months and drove down operational alerts by over 50% — and more important, drove down application support costs by almost 90%, and all this at a time when usage probably doubled.  Wow. 

I’m not sure how you can successfully scale a company rapidly without inefficiencies in technology.  But on the other side of this particular project, I’m not sure how you can afford NOT to work those ineffiencies out of your system as you grow.  Just as most Americans (political affiliation aside) are wringing their hands over the size and growth of our national debt now because they’re worried about the impact on future generations, engineering organizations of high growth companies need to pay attention to their technical debt and keep it in check relative to the size of their business and code base.

And for CEOs, celebrate the payment of technical debt as if Congress did the unthinkable and put our country back on a sustainable fiscal path, one way or another!

As a long Post Script to this, I asked our CTO Andy and VP Engineering David what they thought of this post before I put it up.  David’s answer was very thoughtful and worth reprinting in full:

 I’d like to share a couple of additional insight as to how Andy and I manage Tech Debt in the org: we insist that it be intentional. What do I mean by “intentional”

•  There is evidence that we should pay it
• There is a pay off at the end

 What are examples of “evidence?”

•  Capacity plans show that we’ll run out of capacity for increased users/usage of a system in a quarter or two
• Performance/stability trends are steadily (or rapidly) moving in the wrong direction
• Alerts/warnings coming off of systems are steadily or rapidly increasing

 What are examples of “pay off?”

•  Increased system capacity
• Improved performance/stability
• Decreased support due to a reduction in alerts/warnings

 We ask the engineers to apply “engineering rigor” to show evidence and pay-offs (i.e. measure, analyze, forecast).

 I bring this up because some engineers like to include “refactoring code” under the umbrella of Tech Debt solely because they don’t like the way the code is written even though there is no evidence that it’s running out of capacity, performance/stability is moving in the wrong direction, etc. This is a “job satisfaction” issue for some engineers. So, it’s important for morale reasons, and the Engineering Directors allocate _some_ time for engineers to do this type of refactoring.  But, it’s also important to help the engineer distinguish between “real” Tech Debt and refactoring for job satisfaction.

Connecting the Dots

Although I still maintain that the three primary roles of a CEO are to set Strategy and communicate it, develop Talent, and ensure that the business has proper Resources to run (see post here), I am increasingly finding that I play a fourth role in the organization that’s probably somewhat important, which is Connecting the Dots.

What do I mean by Connecting the Dots?  I mean helping others network internally, or helping others connect their work to the work of others, or helping others connect their work to the mission of the company, or even to the outside world.

Here are a few examples of how I’ve done this kind of work recently:

 –          I joined an Engineering all-hands and stood up after each segment to talk about the business impact of that team’s work during the prior quarter

–          I met with a new senior employee and connected him to someone internally that he wouldn’t have otherwise met with…but with whom he had a common outside interest

–          I helped a team that’s a classic “support team” understand why their work was directly, but not obviously, contributing to one of the company’s strategic initiatives

–          I connected someone in one of our international offices who had expressed an interest to me in a new role with an operational leader in the US who was thinking of adding someone to his team outside the US

–          I talked to our professional services team about a customer visit I’d recently done where we got really good feedback on the next release of a product but which also pointed out some needs for services that we hadn’t focused on yet

As a business leader, you are in a really good position to help Connect the Dots in a growing organization because you have a pretty unique view across the organization – and you tend to spend time with people internally across different functions and teams and offices.

I am not going to change my position that there are three primary roles, because I’m not sure that a CEO is required to Connect the Dots – hopefully that role can be delegated and replicated.  It’s something to think about, for sure.  But in the meantime, I like doing that and find it useful for me as well as the organization.

First in my series of posts around creating the best place to work  is to Surround yourself with the best and brightest.  This one is simple.  Build the best team you can possibly build…as you need it.

As a founder, you may be the best person at doing everything in your company, especially if you are a technical founder.  But as my long-time Board member at Return Path Greg Sands always says, when the organism grows, cells start to specialize.  Eventually, you need a liver and a brain.  Just like companies need a head of sales and a CFO (not to imply that Anita likes the occasional cocktail or that Jack likes math – turns out both like both).

How does this come into play as a CEO?

-Don’t be afraid to hire people better than you at their specialty – older, wiser, more experienced, more expensive

– Check references carefully – don’t get suckered in by resume or rolodex – some successful big company people don’t actually know how to do work or build a business, so you have to dig and find back-channel references

– Don’t overhire before you’re ready, but especially as a start-up, better to hire 3 months before you need the position, not 6 months too late

-Remember that you are the CEO.  Even if you hire very experienced people in specific roles, you have the best global view of everything going on in the company.  And you need to pay attention to people on your team and actively manage them, even experts who are older or wiser than you are

Surrounding yourself with the best and brightest can be daunting and even threatening to some CEOs.  But you have to do it to grow your business.  And you have to keep doing it as you keep growing your business (and your staff has to do the same!).

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

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

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

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

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

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.

This is the hardest thing I’ve ever had to write in 12 years as Return Path’s CEO. I hope it never has an equal.

One of our long-time employees, J.D. Falk, passed away last night after a year-long struggle with cancer. J.D., which most people don’t know was short for Jesse David, was only 37 years old. Although I cannot claim to be a close friend of J.D.’s, I have known him fairly well in the industry going back about eight years, and he has been a trusted member of our team here for the last four+ years.

J.D. did great work for us at Return Path, but my admiration for him goes beyond that. I admire him first for his willingness to work for the common good as much as, or even more than, his own good. J.D.’s tireless pro-bono work with anti-abuse non-profits MAAWG, CAUCE, and the IETF complemented the work he did here for a salary. And although he had a very positive and enduring impact on us at Return Path in terms of how we run our business and think about the delicate balance between email senders and receivers, he had an even bigger, broader impact through his standards work, papers, and tireless work on event programming and committee chairmanship. He did all that work not for money, not for thanks, but because it was, he felt, the right thing to do.

I also admire J.D. tremendously for his extremely principled, but thoughtfully considered, approach to life. His principles around internet users are well known and very “Cluetrain.” And yet, in a world increasingly filled with people whose opinions are intransigent, he was always open-minded and willing to engage in productive dialog with people who had different points of view than his own, sometimes changing his own thoughts and actions as a result of those conversations. That quality is all-too-rare in today’s society.

J.D.’s wife Hope told me a great story that sums up the fiber of J.D.’s being earlier this week. Just last weekend, from his hospital bed, J.D. realized that he and Hope had concert tickets they would be unable to use because of his illness, so he wanted to give them to friends. However, the tickets were only in electronic form on J.D.’s work laptop. Hope said, “J.D., just give me your password, and I’ll go home and print them out so we can give them away.” His response? “I can’t give you my password – that’s against company policy, but bring the laptop here to the hospital, and I can log in myself and forward you the tickets.”

Today is a sad day for me and for all 300 of us at Return Path as we lose a friend and colleague for the first time in our company’s history. And of course today is a sad day for the anti-abuse community that J.D. has been such an integral part of for his entire career. But more than that, today is a sad day for the internet and for the billions of humans that use it – sadder in some ways because they don’t even know that one of the people integrally involved in keeping it safe for them has left us.

I will post again as soon as I can with details of the memorial service for J.D. as well as details of where to make some kind of donation or contribution in his honor. I will post again as soon as I can with details of the memorial service for J.D. as well as details of where to make some kind of donation or contribution in his honor. In the meantime, I encourage J.D.’s many friends and colleagues around the world to post their memories to this memorial site.

The Best Laid Plans, Part I

One of my readers asked me if I have a formula that I use to develop strategic plans.  While every year and every situation is different, I do have a general outline that I’ve followed that has been pretty successful over the years at Return Path.  There are three phases — input, analysis, and output.  I’ll break this up into three postings over the next three weeks.

The Input Phase goes something like this:

Conduct stakeholder interviews with a few top clients, resellers, suppliers; Board of directors; and junior staff roundtables.  Formal interviews set up in advance, with questions given ahead.  Goal for customers: find out their view of the business today, how we’re serving them, what they’d like to see us do differently, what other products we could provide them.  Goal for Board/staff: get their general take on the business and the market, current and future.

Conduct non-stakeholder interviews with a few industry experts who know the company at least a little bit.  Goal: learn what they think about how we were doing today…and what they would do if they were CEO to grow the business in the future.

Re-skim a handful of classic business books and articles.  Perennial favorite include Good to Great, Contrarian Thinking, and Crossing the Chasm.

Hold a solo visioning exercise.  Take a day off, wander around Central Park.  No phone, no email.  Nothing but thinking about business, your career, where you want everything to head from a high level.

Hold senior staff brainstorming.  Two-day off-site strategy session with senior team and maybe Board.

Next up:  the Analysis Phase.