Nov 122015

You Have To Be All In, Until You’re Not

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.”

Aug 272015

The Joy of Coaching

I was the head coach of my two older kids’ little league team this past spring.  The whole thing was a little bit of an accident – I vaguely volunteered for something and ended up in charge.  The commitment was a little daunting, but I was ok with it since the season was only a couple months long, it was both Casey and Wilson, and both kids, especially Wilson, are really into baseball.  Other than helping out a bit here and there, I’d never coached a sports team before.

What started off as an unclear assignment ended up as one of the most fun and fulfilling things I’ve done in years.  I loved every minute of it, looked forward to our practices and games, was hugely bummed out when we got rained out, and never had a moment where I couldn’t make the time for it (though clearly the hours had to come from somewhere!).  Given some of the overlap between leading a sports team and leading a company, I thought I’d reflect on the experience a bit here.  There are some common themes between this post and something I wrote years ago, Parenting and Corporate Leadership, with the same caveat that no, I don’t think employees are children or children are employees.  But here are some things I take away from the experience and apply or compare to work.

We established a clear philosophy and stuck to it.  That’s a step that lots of coaches – and managers in the workplace – miss.  The other coaches and I discussed this before the first practice, agreed on it, and shared it directly with the kids.  For this age group in particular, we felt that we were there first and foremost to have fun; second to learn the game; and third, to play hard and fair.  Note there was nothing in this about winning, and that we were really specific about the order of the three objectives.  Even 7 and 8 year olds know the difference between “win at all costs” and “have fun and play ball.”  We reinforced this at every practice and at every game.  Being intentional about a philosophy and communicating it (and of course sticking to it) are key for any leadership situation.

We got lucky.  As I repeatedly said to the parents on the team, we had a group of awesome kids – happy and generally paying attention, and not one troublemaker in the bunch; and we had a group of awesome parents – responsive, supportive, and not a single complaint about what position a kid was playing or where someone was in the batting order.  I’d heard horror stories about both kids and parents from other coaches ahead of time.  It’s possible that the other coaches and I did such a good job that both kids and parents were great all the time…but I think you have to chalk most of that up to the luck of the draw.  Work isn’t all that different.  Having stakeholders who are consistently positive forces is something that sometimes you can shape (you can fire problematic employees) but often you can’t, in the case of customers or even Board members.  Luck matters.

Stakeholder alignment was a critical success factor.  Having said that, I do think the coaches and I did a good job of keeping our stakeholders aligned and focusing on their needs, not ours.  We put extra effort into a regular cadence of communication with the parents in the form of weekly emails and a current web site.  We used those emails to highlight kids’ performance and also let parents know what we’d be working on in practice that week.  We made sure that we rotated kids in the batting order so that everyone got to bad leadoff once and cleanup once.  We rotated kids so that almost every kid played half of each game in the infield and half in the outfield.  We took any and all requests from kids who wanted to play a specific position for a few innings.  Many of these basic principles – communicating well, a clear operating system, listening to stakeholders, a People First approach – are lessons learned from work as a CEO.

Proper expectations and a large dose of patience helped.  After the first couple games, we were 0-2, and I was very frustrated.  But I reminded myself that 7 and 8 year olds are just kids, and my frustration wasn’t going to help us achieve our objectives of having fun and learning the game.  So I recalibrated my expectations and took much more of a laid-back attitude.  For example, any time I saw one kid goofing off a little bit in practice, I gently got him or her back in line.  But when I saw multiple kids’ attention fading, I took it as a sign that whatever I was doing as a coach wasn’t working, called a break, and did something else.  This kind of “look in the mirror” approach is always helpful at work, too.

Reward and recognition were key.  We definitely adopted a Whale Done! approach with the kids.  We got the kids in the dugout fired up to cheer on batters.  First base coaches did big high fives, smiles, and literal pats on the back for every hit.  Post-game huddles and emails to parents focused on highlights and what went right for the kids.  One of my favorite moments of the season was when one player, who only had one hit all year and struck out almost every time at bat, had two hits, an RBI, and a run scored in our final game.  Not just the coaches, but the other kids and all the parents went absolutely BANANAS cheering for this player, and it brought huge smiles to all our faces.  I am 100% certain that the focus on the positive encouraged the kids to try their hardest all season, much as I believe that same philosophy encourages people to take risks and work hard at the office.

The biggest thing I take back to the workplace with me from the experience.  I was reminded about how powerful achieving a state of “flow,” or “relaxed concentration” is.  I recounted these principles in this blog post from a couple different books I’ve read over the years – Mihaly Csikszentmihalyi’s Flow and Tim Gallway’s Inner Game books – Golf, Tennis, and Work.  The gist of achieving a state of flow is to set clear goals that are stretch but achievable, become immersed in the activity, pay attention to what’s happening, and learn to enjoy immediate experience.  All leaders – in sports, business, or any walk of life – can benefit from this way of living and leading.

I loved every minute of coaching.  It helped that we ended up with a really strong record.  But more than that, building relationships with a bunch of great kids and great parents was fun and fulfilling and incredibly thankful and rewarding.  The “thank you ball” that all the kids autographed for me is now a cherished possession.  Working and getting extra time with my own two kids was the icing on the cake.  All I want to know is…is it time for next season yet?  I am ready!

This post is really for Coaches Mike, Paul, and Oliver; and players Emily, Casey, Lauryn, Mike, Josh, Holden, Hudson, Wilson, Drew, Kevin, Matthew, and Christian.

Oct 092014

Book Short: Way, Way Beyond Books

Book Short:  Way, Way Beyond Books

The Everything Store: Jeff Bezos and the Age of Amazon, by Brad Stone, was a great read.  Amazon is a fascinating, and phenomenally successful company, and Jeff is a legendary technology leader.  The Everything Store is a company and personal biography and totally delivers.

Forget about the fact that Amazon is now almost $100B in revenues and still growing like mad.  I find it even more amazing that a single company could be the largest ecommerce site on the planet while successfully pioneering both cloud computing services and e-readers.  The stories of all these things are in the book.

As a CEO, I enjoyed reading more of the vignettes behind the things that Amazon is reputationally known for in the tech world – doors as desks, their unique meeting formats, the toughness of the culture, the extensive risk taking of growth over profits, and what works and does not work about Bezos’ authoritative and domineering style.  And it’s always great to be reminded that even the biggest and best companies had to cheat death 10 times over before “arriving.”

This is good fun and learning for anyone in the business world.  It reminded me most of Walter Isaacson’s biography of Steve Jobs ,which I wrote about here, although it’s more of a company history and less of a biography than the Jobs book.

Filed under: Books, Entrepreneurship

Tags: ,

Sep 112014

The 2×4

The 2×4

I took a Freshman Seminar in my first semester at Princeton in 1988 with a world-renowned professor of classical literature, Bob Hollander.  My good friend and next-door neighbor Peggy was in the seminar with me.  It was a small group — maybe a dozen of us — meeting for three hours each week for a roundtable with Professor Hollander, and then writing the occasional paper.  Peggy and I both thought we were pretty smart.  We had both been high school salutatorians from good private schools and had both gotten into Princeton, right?

Then the first paper came due, and we were both a bit cavalier about it.  We wrote them in full and delivered them on time, but we probably could have taken the exercise more seriously and upped our game.  This became evident when we got our grades back.  One of us got a C-, and the other got either a D or an F.  I can’t remember exactly, and I can’t remember which was which.  All I remember is that we were both stunned and furious.  So we dropped by to see Professor Hollander during his office hours, and he said the same thing to each of us:  “Matt, sometimes you need a 2×4 between the eyes.  This paper is adequate, but I can tell it’s not your best work, it’s decent for high school but not for college, and almost all the others in the class were much more thoughtful.”


Ever since then, Peggy and I have talked about the 2×4, and how it helped us snap out of our own reality and into a new one with a significantly higher bar for quality.  That phrase made it into Return Path‘s lexicon years ago, and it means an equivalent thing — sometimes we have to have hard conversations with employees about performance issues.  The hardest ones are with people who think they are doing really well, when in reality they’re failing or in danger of failing.  That disconnect requires a big wakeup call — the 2×4 between the eyes — before things spiral into a performance plan or a termination.

Delivering a 2×4 between the eyes to an employee can feel horrible.  But it’s the best gift you can give that employee if you want to shake them back onto a successful trajectory.

Aug 142014

How to Manage Your Career

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.

Mar 202014

Secrets to Yawn-Free Board Meetings

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

Mar 062014

Open Vacation

At Return Path, we’ve had an “open vacation” policy for years, meaning that we don’t regulate the amount of time off people take, and we don’t accrue for it or pay out “unused” vacation if someone leaves the company.  I get asked about this all the time, so I thought I’d post our policy here and also answer a couple follow-up questions I usually get about it.

First, here’s the language of our policy:

Paid Time Off

You’re encouraged to take as much time off as you can while maintaining high performance and achieving your goals. We don’t count the hours you work, so why should we count the hours you don’t? (Unless you’re a non-exempt employee, and only then because we have to!) Take what you need, when you can, and make sure to arrange coverage with your team. If you haven’t had a vacation in a while, you can expect to get a friendly nudge from your manager to get away from the office!

Use your Paid Time Off (PTO) for planned vacations, days off for appointments, religious, or personal holidays that are not offered in your country, community service days, or if you need an unanticipated, last-minute day off to care for a sick child or family member. Statutory or legally protected leaves of absence, such as medical leave, maternity/parental leave, family medical leave or unpaid leave, are governed by separate regulations that will not be affected by our PTO policy. See the Regional section for a list of statutory leaves of absence in your country.

Paid Time Off scheduling is subject to approval by your manager, who has sole discretion to approve or deny requests under this policy. Requests of greater than two consecutive weeks or more than two weeks in one three-month period require approval of your Executive Committee member.

The first question I always get is, “Wow – does that really work?  What issues have you had with it?  My response:

No issues with it at all, other than it’s a little weird to apply internationally, where we have 50 people across 7 countries, since most of those countries have significantly more generous vacation policies/customs than the US.  But we generally make it work.

The second question I get is whether people abuse it or not:

In all the years we’ve done it, we only ever had one person attempt to abuse the policy, one time.  People do still have to ask their managers if it’s ok to take time off, and they do still have to get their jobs done.

Finally, people ask me for general advice on implementing this kind of policy:

Continue to track days off and generate reports for managers every quarter so they at least know whether their people are taking not enough or too much – generally people will take not enough, and you will need to encourage them to take more.  Also, our managers were *really* worried about launching this, so we had to do some hand-holding along the way. 

The results of this policy for us have generally been great.  People take about the same amount of true vacation they used to take, maybe a little more.  They definitely take more half-days and quarter-days where they probably still get a full day worth of work done, without worrying about counting the hours.  Best of all, there’s a strong signal sent and received with this kind of policy that we trust our team members to do what they need to do in order to live their lives AND get their jobs done.

Feb 132014

HR/People Lessons from Netflix

It feels as if almost everyone in our industry has read the famous Netflix culture deck on Slideshare, and with over 5mm views, that may not be too far off.  If you haven’t looked at it before, and if you care about your organization’s culture and how productive and happy employees are the best kind of employees, then take the time to flip through it.

As part of a benchmarking exercise we did on employers with unique and best HR/People practices a few years ago, a few of us did either site visits or at least live interviews with leaders at four companies, all of whom are pretty well known for progressive People practices that are also in-line with our company’s culture:  Morningstar, Gore, Nucor, and Netflix.  As part of this, we met in person with Patty McCord, Netflix’s long-time head of People.  It was a really informative meeting.

Now Patty has written a longform article in Harvard Business Review that shares a lot of what we learned from her in her office that day. It’s absolutely worth a read.  Netflix does have a pretty distinct culture and gets positive but mixed reviews on Glassdoor, so as with everything, I’m not advocating adopting everything they do lock, stock, and barrel.  But I can guarantee that some of the lessons that Patty shares are valuable no matter what your company is like.

Jan 072014

Startup CEO: The Online Course

As most of you know by now, I wrote a book that was published last fall called Startup CEO:  A Field Guide to Scaling Up Your Business.  I’m excited to announce that, starting on January 20th, the book has now been turned into Kauffman Fellows Academy (KFA) online course called Startup CEO.  Similarly, Brad Feld and Jason Mendelson’s highly successful Venture Deals is also going to launch as Venture Deals KFA online course on February 24th. Both will be offered initially on the NovoEd platform.

The parties involved in getting it off the ground (besides me) were the team at Kauffman Fellows Academy and NovoEd.  Clint Korver, a serial entrepreneur and Stanford adjunct professor, spearheaded the project, and between filming the course and now, he switched jobs from KFA to be the COO at NovoEd, so he has been on all sides of this.   NovoEd is a very unique online educational platform that gives students the ability internationally to work together in teams and collaborate on assignments and peer review one another’s work.  So far over 1,300 people have signed up for Startup CEO from countries as far-flung as the China, Brasil, Iran, the U.K., Australia and, of course, Silicon valley..  This is an exciting extension of the book for me to watch unfold.

The class itself is a very unique format, a bit of “the entrepreneur’s studio” model.  For each chapter of the book (there are 48), I filmed a 5-10 minute Q&A with Clint in front of a live audience of a dozen startup CEOs in New York.  This was a serious production – much more than I expected – with a three-person former CNN production team of Kevin Rockwell, Chuck Afflerbach, and led by former Emmy Award winning CNN Correspondent Rusty Dornin.  Preparing for the class this way was fun and gave me a good opportunity to further crystallize the main point or theme of each chapter.  Having a live audience was super helpful to see what worked and what didn’t work.

Jan 022014


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!