Running a Productive Offsite
Running a Productive Offsite
A couple OnlyOnce readers asked me to do a post on how I run senior team offsites. It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.
My senior team has four offsites per year. I love them. They are, along with my Board meetings, my favorite times of the year at work. Here’s my formula for these meetings:
–         WHY: There are a few purposes to our offsites. One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level. So for us, these are the only times of the year that we are actually in the same place. But even if we were all in one place, we’d still do them. The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time. The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics. It’s critically important to build and sustain deep relationships across the Executive Team. We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company. As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical
–         WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total). Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people). That part is new as we’ve gotten bigger. In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics
–         WHERE: Offsites aren’t always offsite for us. We vary location to make geography work for people. And we try to contain costs across all of them. So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel. Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place. Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night
–         WHEN: 4x/year at roughly equal intervals. We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded. Now we basically do them between Board meetings. The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year. Our general formula when it’s the smaller group is two days and at least one, maybe two dinners. When it’s the larger group, it’s three days and at least two dinners. For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.
–         WHAT: Our offsites are super rigorous. We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations. The agenda for these offsites varies widely, but the format is usually pretty consistent. I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union. Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc. We always try to spend half a day on team and individual development. Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing. Then we have a team development plan check-in that’s the same, but about how the team is interacting. We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time. Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!). There’s also time at breaks for sub-group meetings and ad hoc conversations. We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it. Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m. We usually have a closing check-out, next steps recap type of exercise as well.
–         HOW: Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.
I’m sure I missed some key things here. Team, feel free to comment and add. Others with other experiences, please do the same!
Book Short: Loving the Strengths Movement More Than the Book
Book Short:Â Loving the Strengths Movement More Than the Book
I’m a big believer in the so-called Strengths Movement — that we would all be better served by playing to our strengths than agonizing over fixing our weaknesses. I think it’s true both in professional and personal settings.
The books written by Marcus Buckingham that come out of Gallup’s extensive research into corporate America, First, Break All the Rules (about management) and Now, Discover Your Strengths (self-management) are both quite good. Another book written by someone else off the same research corpus, 12: The Elements of Great Managing is ok, but not as good, as I wrote about here.
Buckingham’s newest, Go Put Your Strengths to Work: 6 Powerful Steps to Achieve Outstanding Performance, is fine and has some good points but is way too long, a little hokey, and has a lot of online companion material that is far more interesting sounding than it is actually useful.
The book does build nicely on Now, Discover Your Strengths by giving you inspiration and a framework for taking those signature themes from the prior book and translating them into action — stuff you actually do every day that plays to your strengths and draws out your weaknesses. And that’s helpful. Some of his suggestions for what you do with that information are ok but a bit common sense only and way too drawn out (“here’s how to talk to your boss…”).
To be fair, I am going to do some of the work that Buckingham recommended doing — so I guess that says something about the power of the book, or at least the movement underlying it. But not the best read in the world.
Book Short: Tech Founder? Varsity Basketball Captain? Both! At the Same Time!
Book Short: Tech Founder? Varsity Basketball Captain? Both! At the Same Time!
Ben Casnocha’s My Startup Life has some of the same appeal as The Mousedriver Chronicles (which I reviewed years go here) in its tale of a startup, its successes, failures, and lessons learned. If you like that kind of book or are starting a company and are looking for kindred spirits, it’s a good book for you.
Ben’s story is more remarkable in some ways because he started his eGovernment software (SaaS of course) company Comcate at the age of 13. That’s right, 13. When I was learning how to shave, having a bar mitzvah, and dealing with acne and a voice dropping at terminal velocity. Starting a business was the furthest thing from my mind. Though to be fair, teenage entrepreneurs are a featured new demographic in Mark Penn’s Microtrends (also worth a read). Perhaps if I were Ben’s age today, I would be a startup junkie, too.
I’ve had the pleasure of meeting Ben a couple times via Brad — I think Brad MUST have been a lot like him 20ish years ago. The advice in the book is good and relevant and incredibly mature for a 20-year old, and Ben, I mean that in an impressed way, not a patronizing one. It’s not necessarily revolutionary, but it’s a very quick and light read if you like the genre/premise.
Book Short: Great Marketing Checklists
Book Short:Â Great Marketing Checklists
Trade Show and Event Marketing: Plan, Promote, and Profit, by our direct marketing colleague Ruth Stevens, is hardly a page-turner, but it is a great read and well worth the money for anyone in your B2B marketing department. That’s true as much for the event marketing specialist as the marketing generalist.
The author brings a very ROI-focused approach to planning and executing events – whether big trade shows or smaller corporate events, which are becoming increasingly popular in recent years for cost, focus, and control reasons. But beyond events, the book has a number of excellent checklists that are more general for marketers that I found quite useful both as a reminder of things we should be doing at Return Path as well as ways we should be thinking about the different elements of our B2B marketing mix.
Some of the best tables and charts include: strengths, weaknesses, and best applications of trade shows vs. corporate events; comparative analysis of marketing tools by channel (this was great – talks about best applications for all major tools from events to newsletters to search to inside sales); 12-month exhibitor timeline for trade shows; a great riff on bad booth signage vs. good booth signage (hint: don’t make the visitor do the work – be obvious!); business event strategic planning grid; pre-show campaign and post-show follow-up checklists; dos, don’ts and options for corporate events; a great section on qualifying and handling leads that extends well beyond trade shows; and several good case studies that are show-focused.
Thanks to Ruth herself for an autographed copy! Team Marketing and sales leaders at Return Path – your copies are on the way.
Book Short: You’d Never Run Your Business This Way…
Book Short:Â You’d Never Run Your Business This Way…
I am an unabashed conservative, so you might wonder what I was doing reading A Country That Works, by union chief Andy Stern, the President of SEIU (Service Workers International Union) this weekend. Well, part of it is that my mother-in-law Carmen works for him. Part was that he was quite inspiring during his recent appearance on the Colbert Report a week or two ago. And part was that I always like reading about different points of view, especially with the current, somewhat dismal state of the Republican leadership in Washington.
The book was very short and a worthwhile read. I may not agree with Stern on some of his illustrations of the problems — his statistical presentations were a bit apples-to-oranges at times — and some of his solutions, which were a bit high on the big-government-tax-and-spend side for me, but the book was very plain-speak, apolitical, and solution-oriented, all of which I found refreshing.
He certainly had at least one underlying premise about “labor as electricity ” (compete on something else other than forcing wages to go lower) that is making me think hard about my long-standing philosophical opposition to federally-mandated minimum wages. His notion of the importance of a global labor movement to act as a check/balance on corporate globalization both make sense. Actually, now that I think about it, those two things put together start working well as one plank in a solution to global poverty.
But the best part of the book was the fact that Stern is clear that, like his ideas or hate them, he is at least proposing that we DEAL with them. America is missing serious debate about some critical issues facing our society. Anyone who doesn’t think we have serious problems facing our future around retirement savings, education, and health care is not facing reality. The debate happening in Washington today is weak at best, and over-politicized.
The bottom line is that I think we’re in danger as a country of boiling the frog when it comes to some major structural issues in our society, and, most important to me, You’d Never Run Your Business This Way. Any good entrepreneur knows that when danger lurks around the corner, you have to reinvent yourself, and we as a country aren’t doing that at this moment when we’d benefit from it greatly for the long term. Stern displays that mix of optimism for the future and serious reality check today known as the Stockdale Paradox and revered by Jim Collins in his two books on corporate leadership, Good to Great and Built to Last.
My biggest criticism of the book was that it was too short. It was basically 1/3 Andy’s story, 1/3 SEIU’s story, and 1/3 labor’s story — and it could have been at least twice as long and gone into more detail on Stern’s points, especially in the last chapter where he starts spelling out his plan to get America back on track. But presumably when Stern runs for national office or gets a cabinet appointment someday (no inside knowledge here, but the book certainly reads that way), he’ll flesh things out a bit!
Book Short: Loved Loved
I enjoy reading books written by people I know. I can always picture the person narrating the book, or hear their voice saying the words, I can periodically see their personality showing through the words on the page, and books bring out so much more detail than I’d ever get from a conversation. Loved: How to Rethink Marketing for Tech Products, by Martina Lauchengco, is one of those books. Martina is an operating partner at Costanoa Venture Capital, an investor in both Return Path and Bolster, and I’d known Martina for several years before she joined Costanoa through Greg Sands. She’s the best product marketer on the planet. She’s the also one of the nicest people around.
Product Marketing is a tricky discipline. A brand marketer on my leadership team years ago referred to it somewhat derisively as a “tweener” function, one of those things that’s not quite marketing and not quite product. We didn’t get the function right for many years at Return Path because we treated it that way, thinking “well, it’s neither fish nor fowl, so we’re not quite sure what to do with it.” Then we hired Scott Roth, who has gone on to have a storied career as a multi-time CEO. Scott’s background was in product marketing. He said to me in his interview process, “Product Marketing isn’t a tweener function with no home. It’s a glue function. It holds product and marketing together.” It’s amazing how that simple change in framing, combined with great leadership, led us to completely rethink the function and make it one of the most important functions in the company.
Martina brings that to live with Loved. Simply put, Loved is a handbook or a field guide to running the Product Marketing function. I can imagine it being a section of Startup CXO in that way — it’s incredibly practical, hands-on, how-to, and rich with examples from Martina’s amazing career at Microsoft, Netscape, Silicon Valley Product Group, and Costanoa. And she believes in Agile Marketing, which is always a plus in my book (and I find rare in marketers).
Martina has lots of great frameworks and stories in the book – key responsibilities of product marketing, key metrics, the release scale, the connection to Geoffrey Moore’s TALC, strategies for messaging, pricing and packaging, and more. I won’t spoil more than one here, but I will paraphrase one that I found particularly impactful, a bit of a checklist on the essence of great product marketing:
- Share data around shifting trends in buyer behavior
- Connect your product’s purpose with broader trends
- Rebrand to make your product seem bigger than it is (and save room for expansion down the road)
- Make it free, especially if you’re defining a new category
- Share the “why” and advance access with influencers
If the measure of a book’s impact is how many pages you dog ear or highlight, this says it all about Loved.

Book Short: Blink Part II
Book Short:Â Blink Part II
Years ago I wrote a post about Malcolm Gladwell’s excellent book, Blink (post, buy). While my post has lots of specifics in it for entrepreneurs, for VCs, and for marketers, my quick summary was this:
Where The Tipping Point theorizes about how humans relate to each other and how fads start and flourish in our society, Blink theorizes about how humans make decisions and about the interplay between the subconscious, learned expertise, and real-time inputs. But Gladwell does more than theorize — he has plenty of real world examples which seem quite plausible, and he peppers the book with evidence from some (though hardly a complete coverage of relevant) scientific and quasi-scientific studies.
I recently finished another book, Thinking Fast, and Slow, by Daniel Kahneman, which was very similar. I’d call it the academic version of Blink, or that Blink is the journalistic version of it. Kahneman breaks down our ability to think and process information into what he calls System 1 (quick and intuitive) and System 2 (slower, rational and logical). As he puts it:
In summary, most of what you (your System 2) think and do originates in your System 1, but System 2 takes over when things get difficult, and it normally has the last word.
The book is rich in examples, and while it’s a bit long and sometimes slow going, it is an excellent read if you want to learn more about how the brain works. The work applications are many – we do a lot of work at Return Path on understanding and avoiding Unconscious Bias at work – and this book gave me a bunch of good ideas around that. It’s clear that it’s impossible to become a true master of your intuition vs. logic, but you can design some systems, or at least insert some checks and balances into other systems, to blunt the impact of faulty intuition or lazy logic. The book also has an overwhelming number of labels it applies to common situations – great, but hard to keep them all straight (the priming effect, anchors, endowment effect, etc.).
Perhaps the most interesting thing for me to ponder as an entrepreneur, though, was the section on Loss Aversion (another great label). It turns out we humans are motivated more by fear of loss than by the prospect of gain. A poignant example in the book is that professional golfers make a higher percentage of putts (I forget the actual number, but a real one, like 3-5%) for par than for birdie, when the putts are like-for-like in terms of distance and difficulty. Saving par is more of a motivator than being under par. The application for work is interesting. As companies get larger, it can be difficult for founders and management teams to maintain the same level of bold risk-taking they did as smaller organizations. Having something to lose is harder than having nothing to lose. And yet, as they say, fortune favors the bold. Growth stage companies need to figure out how to institutionalize risk taking and experimentation, including putting enough resources into those activities that will generate future growth, rather than simply protecting what’s already running. (Of course, what’s already running needs investment, too.)
Thanks to my colleagues Dragana and Richard for recommending this book, and to Jamie for facilitating our office book club around it this month!
Startup CEO (OnlyOnce- the book!)
Startup CEO (OnlyOnce – the book!)
One of the things I’ve often thought over the years since starting Return Path in 1999 is that there’s no instruction manual anywhere for how to be a CEO. While big company CEOs are usually groomed for the job for years, startup CEOs aren’t…and they’re often young and relatively inexperienced in business in general. That became one of the driving forces behind the creation of my blog, OnlyOnce (because “you’re only a first time CEO once”) back in 2004.
Now, over 700 blog posts later, I’m excited to announce that I’m writing a book based on this blog called Startup CEO: A Field Guide to Building and Running Your Company. The book is going to be published by Wiley & Sons and is due out next summer. The book won’t just be a compendium of blog posts, but it will build on a number of the themes and topics I’ve written about over the years and also fill in lots of other topics where I haven’t.
The catalyst for writing this book was Brad Feld. Brad has been a friend, mentor, investor, and Board member for over a decade. We’ve had many great times, meals, and conversations together over the years, not the least of which was staggering across the finish line together at the New York City Marathon in 2005. Brad started writing books a few years ago, and I’ve been peripherally involved with them, first with Do More Faster: TechStars Lessons to Accelerate Your Startup (I contributed one of the chapters) and then with Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist (I wrote all the “Entrepreneur Perspective” sidebars).
Those are great books, and they’ve been incredibly well received by the global entrepreneurial community. But then Brad got the bug, and now he’s in the middle of writing FOUR new books with Wiley that will all come out over the next year. They are:
- Startup Communities:Â Building an Entrepreneurial Ecosystem in Your City
- Startup Life:Â Surviving and Thriving in a Relationship with an Entrepreneur
- Startup Metrics:Â Making Sense of the Numbers in Your Startup
- Startup Boards:Â Reinventing the Board of Directors to Better Support the Entrepreneur
These four books, plus the two earlier ones, plus Startup CEO, are all part of the Startup Revolution series. While I’ll continue to do most of my blogging and posting here on OnlyOnce, I’d also encourage you to check out the Startup Revolution site and sign up to be a member of that community. I’ll be doing some things on that site as well in connection with Startup CEO, and it’s a more concentrated place to post and comment on all things Startup. In addition, we’ll be putting a bunch of add-ons to the book on that site closer to publication time.
I hope Startup CEO becomes a standard for all new CEOs. I don’t think I have all the answers, but at least others can benefit by learning from my 13 years of successes and mistakes! Now all I have to do is go write the darned thing.
Book Short: A Good Dose of Introspection
Book Short:Â A Good Dose of Introspection
I rarely blog about non-business books since this is a business blog — and I read a lot of them! But occasionally, one manages to slip in, and this time, it’s The Five People You Meet in Heaven, by Mitch Albom. From the author of Tuesdays With Morrie, which I also liked quite a bit, this one is excellent. And a very, very quick read.
The book, in short (i.e., a book short <g>), is about a guy who dies, and who, in heaven, meets five people who have shaped his life and died before him. Some he knows well, some he knows barely, some he’s never met. Each one tells him a story that explains some part of his life to him and in doing so, helps him understand more about himself and why/how he lived on earth.
The book, as I said, is a short read. But more than that, it’s a wonderful story and provides an opportunity for a structured moment of introspection, one that I found very valuable. Quite frankly, this book should be a “once every year or two” read.
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 two books, The Undoing Project had too much overlap and not enough “underlap” (to quote my friend Tom Bartel) – that is, not enough new stuff of substance for me. The book mostly went into the personal relationship between two academic thinkers, Daniel Kahneman and Amos Tversky. It also touched on some of the highlights of their work, which, while coming out of the field of psychology, won them a Nobel prize in Economics for illuminating some of the underlying mechanics of how we make decisions.
The two most interesting pieces of their work to me, which are related in the book, are:
First, that human decision-making is incredibly nuanced and complex, and that at least 25% of the time, the transitive property doesn’t apply. For example, I may prefer coffee to tea, and I may prefer tea to hot chocolate, but that doesn’t necessarily mean I prefer coffee to hot chocolate.
From the book, “When faced with complex multidimensional alternatives, such as job offers, gambles or [political] candidates, it is extremely difficult to utilize properly all the available information.” It wasn’t that people actually preferred A to B and B to C and then turned around and preferred C to A. It was that it was sometimes very hard to understand the differences. Amos didn’t think that the real world was as likely to fool people into contradicting themselves as were the experiments he had designed. And the choice created its own context: Different features might assume greater prominence in the mind when the coffee was being compared to tea (caffeine) than when it was being compared to hot chocolate (sugar). And what was true of drinks might also be true of people, and ideas, and emotions. The idea was interesting: When people make decisions, they are also making judgments about similarity, between some object in the real world and what they ideally want. They make these judgments by, in effect, counting up the features they notice. And as the noticeability of features can be manipulated by the way they are highlighted, the sense of how similar two things are might also be manipulated.”
Second, what Kahneman and Tversky called Prospect Theory, which is basically that humans are more motivated by the fear of loss as opposed to the greed of gain. I’ve written about the “Fear/Greed Continuum” of my former boss from many years ago before. I’m not sure he knew about Kahneman and Tversky’s work when he came up with that construct, and I certainly didn’t know about it when I first blogged about it years ago. Do this experiment – ask someone both of these questions: Would you rather be handed $500 or have a 50% chance of winning $1,000 and a 50% of getting nothing? Then, Would you rather hand me $500 or have a 50% chance of owing me $1,000 and a 50% chance of owing me nothing? Most of the time, the answers are not the same.
For fun, I tried this out on my kids and re-proved Prospect Theory, just in case anyone was worried about it.
Anyway, bottom line on this book – read it if you haven’t ready those other two books, skip it if you have, maybe skim it if you’ve read one of them!
Book Short: A Brand Extension That Works
Book Short:Â A Brand Extension That Works
Usually, brand or line extensions don’t work out well in the end. They dilute and confuse the brand. Companies with them tend to see their total market share shrink, while focused competitors flourish. As the authors of the seminal work from years ago, Positioning: The Battle for Your Mind, Jack Trout and Al Reis would be the first people to tell you this.
That said, The New Positioning, which I guess you could call a line extension by Jack Trout (without Reis), was a fantastic read. Not quite as good as the original, but well worth it. It’s actually not a new new book – I think it’s 12 years old as opposed to the original, which is now something like 25 years old, but I just read it and think it’s incredibly relevant to today’s world.
Building on the original work, Trout focuses more this time on Repositioning and Brand Extensions — two things critical to most businesses today. How to do the impossible, to change people’s minds about your brand or product mid-stream, whether in response to new competitive activity or general changes in the world around you. And how to think about brand extensions (hint: don’t do them, create a new brand like Levi’s did with Dockers).
The book also has a very valuable section on the importance of sound and words to branding and positioning, relative to imagery. Trout has a short but very colorful metaphor about women named Gertrude here that’s reminiscent of the research Malcolm Gladwell cited in Blink.
If you haven’t read the original Positioning, that should be on your wish list for the holidays. If you have, then maybe Santa can deliver The New Positioning!