May 18, 2017

Being a CEO is Like Playing a Game of Hearts

Hearts was one of my favorite card games in college.  I remember staying up deep into the night regularly with my roommates playing it.  I recently taught our kids how to play and have been playing with them more regularly of late…and I was reminded how much I enjoy the game.  No metaphor or simile is perfect, and this one isn’t either, but it occurred to me the other night that being a CEO is a little bit like playing a game of Hearts. First and foremost, you have to play the hand that you’re dealt.  No matter how proactive you want to be about running your own agenda, things happen around you — with your people, your customers, your competitors, and you have to figure out how to react to situations. Second, you usually get to pass 3 cards to another player, but sometimes you have a “hold” hand.  Even within a situation you have to react to, sometimes you can mute the edges of it before you actually react (but occasionally, you can’t change the situation at all).  Consider the difference between a customer telling you they are about to churn (maybe you can still save them on […]


May 4, 2017

Why Our Executive Team Does Daily Standup Meetings

Another CEO with whom I trade notes on the craft of running a company asked me this question the other day, and I thought the answer would make a for a good blog post.  Any product team (or other kind of team) who has Agile practices, does some kind of a Daily Standup (DSU) meeting in which each team member reviews progress against goals for a given period and highlights issues where he or she is blocked and needs help.  I wrote about Return Path‘s journey to implement Agile across the whole company last year here. My meeting routines have been […]


April 17, 2017

A Two Week Vacation is More Than Twice As Good As a One Week Vacation

I’ve said this for years, but as I sit on the train commuting into work after a week off relaxing with my family for my Dad’s 75th birthday (or as he prefers to call it, the 46th anniversary of his 29th birthday), I feel particularly inclined to write it up! I love my job, so I almost never mind going to work. But I also love being on vacation and traveling with my family and try to do as much of it as I can. Years ago before we had kids and became tethered to school and sports schedules, we […]


April 6, 2017

What kind of team do you run? Of Generalists and Specialists…

A friend of mine just left his job as CEO of a growth stage company to become CFO of a Fortune 500 company.  That’s a big deal…and also a big change.  When I was talking to him about the move, he said the following to me: Some executive teams are like baseball teams.  You play shortstop, and you bat 8th.  That’s just what you do.  The team needs one of those because the sport is structured that way.  The CEO of my new company likes to run his executive team as a basketball team.  Everyone has a position, but everyone also has […]


March 30, 2017

Everything is Data, Part II – Get Those Expenses In

Everything is Data, Part II – Get Those Expenses In My friend and former colleague Angela Baldonero (used to run our People Team at Return Path, now is COO of super cool startup Procurify), used to say about her job as head of HR, “Everything is Data.”  She guest blogged about that principle on OnlyOnce years ago here , and she particularly cited this theory when talking about the recruiting and hiring process. I’ve thought about this principle a lot over the years, and I’ve occasionally come up with other examples where I think peripheral data can inform whether or not […]


March 16, 2017

Book Short – Blink part III – Undo?

Book Short – Blink part III – Undo? I just finished reading Michael Lewis’s The Undoing Project: A Friendship That Changed Our Minds, and honestly, I wish I could hit Life’s Undo button and reclaim those hours.  I love Michael Lewis, and he’s one of those authors where if he writes it, I will read it.  But this one wasn’t really worth it for me. Having said that, I think if you haven’t already read both Malcolm Gladwell’s Blink (review, buy) and Daniel Kahneman’s Thinking, Fast and Slow (review, buy), then it might be worth it.  But having read those […]


March 2, 2017

Stamina

Stamina A couple years ago I had breakfast with Nick Mehta, my friend who runs the incredibly exciting Gainsight.  I think at the time I had been running Return Path for 15 years, and he was probably 5 years into his journey.  He said he wanted to run his company forever, and he asked me how I had developed the stamina to keep running Return Path as long as I had.  My off the cuff answer had three points, although writing them down afterwards yielded a couple more.  For entrepreneurs who love what they do, love running and building companies […]


February 16, 2017

Reboot – Where do a company’s Values come from, and where do they go?

I’ve written a lot over the years about Return Path’s Core Values (summary post with lots of links to other posts here).  And I’ve also written and believe strongly that there’s a big difference between values, which are pretty unchanging, and culture, which can evolve a lot over time.  But I had a couple conversations recently that led me to think more philosophically about a company’s values. The first conversation was at a recent dinner for a group of us working on fundraising for my upcoming 25th reunion from Princeton.  Our guest speaker was a fellow alumnus who I’ve gotten to know […]


February 9, 2017

Book Short: Why Wait?

A Sense of Urgency, by John Kotter, is a solid book – not his best, but worth a read and happily short, as most business books should be.  I originally was going to hold off on writing this post until I had more time, but the subject matter alone made me think that was a mistake and that I should write it while it’s fresh in my mind.  <g> The three tools to fight complacency are the organizing framework for the book — bring the outside in, behave with urgency every day, and turn crises into opportunities — are all good thoughts, and […]


February 2, 2017

Book Short – A Smattering of Good Ideas that further my Reboot path

Book Short – A Smattering of Good Ideas that further my Reboot path Ram Charan’s The Attacker’s Advantage was not his best work, but it was worth the read.  It had a cohesive thesis and a smattering of good ideas in it, but it felt much more like the work of a management consultant than some of his better books like Know How (review, buy), Confronting Reality (review, buy), Execution (review, buy), What the CEO Wants You to Know ( buy), and my favorite of his that I refer people to all the time, The Leadership Pipeline (review, buy). Charan’s framework for […]


January 19, 2017

Reboot – Founders’ Dinner

Brad wrote a fun post a couple years ago about rituals, including one about The Annual Dinner that he and Amy, Fred and Joanne Wilson, and Mariquita and I have been having not quite annually for almost 15 years now.  His most poignant comment (other than that apparently he and I are both getting larger and greyer in sync with each other) is about the power of marking the passage of time together with the same group of people.  We have a similar tradition at Return Path that’s worth noting in the context of my reboot program since it happened a […]