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!

My name is Matt Blumberg. I am a technology entrepreneur and business builder based in New York City who just (in 2020) started a new company called Bolster.

Bolster is an on-demand executive talent marketplace that helps accelerate companies’ growth by connecting them with experienced, highly vetted executives for interim, fractional, advisory, project-based or board roles. Bolster also provides on-demand executives with software and services to help them manage their careers as independent consultants and provides startup and scaleup CEOs with software and content to help them assess, benchmark and diversify their leadership teams and boards.  We are creating a new way to scale executive teams and boards.

Before that, I started a company called Return Path, which we sold in 2019.   We created a business that was the global market leader in email intelligence, analyzing more data about email than anyone else in the world and producing applications that solve real business problems for end users, commercial senders, and mailbox providers.  In the end, we served over 4,000 clients with about 450 employees and 12 offices in 7 countries.  We also built a wonderful company with a signature People First Culture that won a number of awards over the years, including Fortune Magazine’s #2 best mid-sized place to work in 2012.

Early in my career, I ran marketing and online services for MovieFone/777-FILM (www.moviefone.com), now a division of AOL. Before that — I was in venture capital at General Atlantic Partners (www.gapartners.com), and before that, a consultant at Mercer Management Consulting (www.mercermc.com). And I went to Princeton before that.

Based on this blog, I wrote a book called Startup CEO:  A Field Guide to Scaling Up Your Business, which was published by Wiley in 2013 and updated in 2020.

I have been married for over 20 years to Mariquita, who is, as I tell her all the time, one of the all-time great wives. We have three great kids, Casey, Wilson, and Elyse.

I have lots of other hobbies and interests, like coaching my kids’ baseball and softball teams; traveling and seeing different corners of the world; reading all sorts of books, particularly about business, American Presidential history, art & architecture, natural sciences (for laymen!), and anything funny; cooking and wishing I lived in a place where I could grill and eat outdoors year-round; playing golf; lumbering my way through the very occasional marathon, eating cheap Mexican food; introducing my kids to classic movies; and playing around with new technology.

IF YOU WANT TO UNDERSTAND WHAT THIS BLOG IS ALL ABOUT, read my first two postings: You’re Only a First Time CEO Once, and Oh, and About That Picture, as well as my updated post when I relaunched the blog with its new name, StartupCEO.com.

Book Short:  The Little Engine that Could

Authors Steven Woods and Alex Shootman would make Watty Piper proud.  Instead of bringing toys to the children on the other side of the mountain, though, this engine brings revenue into your company.  If you run a SaaS business, or really if you run any B2B business, Revenue Engine:  Why Revenue Performance Management is the Next Frontier of Competitive Advantage, will change the way you think about Sales and Marketing. The authors, who were CTO and CRO of Eloqua (the largest SaaS player in the demand management software space that recently got acquired by Oracle), are thought leaders in the field, and the wisdom of the book reflects that.

The book chronicles the contemporary corporate buying process and shows that it has become increasingly like the consumer buying process in recent years.  The Consumer Decision Journey, first published by McKinsey in 2009, chronicles this process and talks about how the traditional funnel has been transformed by the availability of information and social media on the Internet.  Revenue Engine moves this concept to a B2B setting and examines how Marketing and Sales are no longer two separate departments, but stewards of a combined process that requires holistic analysis, investment decisions, and management attention.

In particular, the book does a good job of highlighting new stages in the buying process and the imperatives and metrics associated with getting this “new funnel” right.  One that resonated particularly strongly with me was the importance of consistent and clean data, which is hard but critical!  As my colleague Matt Spielman pointed out when we were discussing the book, the one area of the consumer journey that Revenue Engine leaves is out is Advocacy, which is essential for influencing the purchase process in a B2B environment as well.

One thing I didn’t love about the book is that it’s a little more theoretical than practical. There aren’t nearly enough detailed examples.  In fact, the book itself says it’s “a framework, not an answer.”  So you’ll be left wanting a bit more and needing to do a bit more work on your own to translate the wisdom to your reality, but you’ll have a great jumping off point.

Please go put Decide and Conquer: 44 Decisions that will Make or Break All Leaders by David Siegel on your reading list, or buy it. David’s book is up there on my list with Ben Horowitz’s The Hard Thing About Hard Things. It’s a totally different kind of book than Startup CEO, and in some ways a much better one in that there’s a great through-line or storyline, as David shares his leadership framework in the context of his journey of getting hired to replace founder Scott Heiferman as Meetup’s CEO after its acquisition by WeWork, including some juicy interactions with Adam Neumann, through the trials and tribulations of WeWork as a parent company, through COVID and its impact on an in-person meeting facilitator like Meetup, through to the sale of Meetup OUT of WeWork.

It’s hard to do the book justice with a quick write up. It’s incredibly concise. It’s clear. It’s witty. Most of all, it’s very human, and David shares a very human, common sense approach to leadership. I particularly like a device he uses to reinforce his main points and principles by bolding the key phrases every time they show up in the book: be kind, be confident, be bold, expand your options, focus on the long-term picture, be pragmatic, be honest, be speedy, do what’s right for the business, work for your people and they’ll work for you, be surprised only about being surprised. These all resonate with me so much.

One of the interesting things about the book is that David is a CEO, but not a founder (although he was sort of a re-founder in this case). A lot of CEO books talk about how to run a company, or give stories from the trials and tribulations thereof, but few focus on the elements of interviewing for the CEO job, or taking over the reins of a company in the midst of a turbulent flight. So the book is about getting the job, starting the job, doing a turnaround, leading a company through growth, a buy-out, and managing a company inside of another company. And because Meetup is such an iconic brand and business, it’s easy to understand a lot of the backdrop to David’s story.

I just met David for the first time a few weeks ago. We knew a bunch of people in common from his DoubleClick days. We instantly hit it off and traded copies of our books, and then were reading them at the same time trading emails about the parts that clicked. I just can’t recommend the book enough to any CEO or founder. In my view, it joins a pretty elite canon.

Book Short:  Tales of Two Cities

Return Path is basically dual-headquartered in New York City and Broomfield, Colorado, so two recently published books which provide history and insights into the tech industry in those two cities were both of interest to me.

Startup Communities: Building an Entrepreneurial Ecosystem in Your City, by Brad Feld (book, kindle) came out a few months ago and is part of Brad’s Startup Revolution series which will also include my upcoming book Startup CEO, to be published this fall.  In the book, Brad uses the example of the Boulder/Denver area and a few different sectors to demonstrate a blueprint to creating an entrepreneurial ecosystem – the kind that are popping up all over the world of late.

Tech and the City: The Making of New York’s Startup Community, by Alessandro Piol (kindle only) hits on many of the same themes and topics as they relate to New York City, although the book is more of a history of the New York tech scene than a framework with examples.  The book draws heavily on quotes from Fred Wilson, like Brad, a long time friend and Board member.  One of the things the book left me thinking about was what the New York tech scene will look like in 30 years after the new Cornell-Technion campus is up and running.  That plus the current momentum of the tech industry in New York, plus the sheer commercial scale of the city, could really produce an interesting environment down the road that actually starts to rival Silicon Valley, though rival probably isn’t the right word.

All in, these two books do a good job of chronicling the industry I work in, in the two cities where I work, but they also abstract nicely to broader principles about public-private collaboration as well as sector development.

5 Ways to Get Your Staff on the Same Page

[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]

When a major issue arises, is everybody at your company serving the same interests? Or is one person serving the engineering team, another person serving the sales team, one board member serving the VC fund, another serving the early-stage “angels” and another serving the CEO? If that’s the case, then your team is misaligned. No individual department’s interests are as important as the company’s.

To align everyone behind your company’s interests, you must first define and communicate those goals and needs. This requires five steps:

1. Define the mission. Be clear to everyone about where you’re going and how you’re going to get there (in keeping with your values).
2. Set annual priorities, goals, and targets. Turn the broader mission into something more concrete with prioritized goals and unambiguous success metrics.
3. Encourage bottom-up planning. You and your executive team need to set the major strategic goals for the company, but team members should design their own path to contribution. Just be sure that you or their managers check in with them to assure that they remain in synch with the company’s goals.
4. Facilitate the transparent flow of information and rigorous debate. To help people calibrate the success, or insufficiency, of their efforts, be transparent about how the organization is doing along the way. Your organization will make better decisions when everyone has what they need to have frank conversations and then make well-informed decisions.
5. Ensure that compensation supports alignment (or at least doesn’t fight it). As selfless as you want your employees to be, they’ll always prioritize their interests over the company’s. If those interests are aligned – especially when it comes to compensation – this reality of human nature simply won’t be a problem.

Taken in sequence, these steps are the formula for alignment. But if I had to single out one as the most important, it would be number 5: aligning individual incentives with companywide goals.

It’s always great to hear people say that they’d do their jobs even if they weren’t paid to, but the reality of post-lottery-jackpot job retention rates suggests otherwise. You, and every member of your team, “work” for pay. Whatever the details of your compensation plan, it’s crucial that it aligns your entire team behind the company’s best interests.

Don’t reward marketers for hitting marketing milestones while rewarding engineers to hit product milestones and back office personnel to keep the infrastructure humming. Reward everybody when the company hits its milestones.

The results of this system can be extraordinary:

• Department goals are in alignment with overall company goals. “Hitting product goals” shouldn’t matter unless those goals serve the overall health of your company. When every member of your executive team – including your CTO – is rewarded for the latter, it’s much easier to set goals as a company. There are no competing priorities: the only priority is serving the annual goals.
• Individual success metrics are in alignment with overall company success metrics. The one place where all companies probably have alignment between corporate and departmental goals is in sales. The success metrics that your sales team uses can’t be that far off from your overall goals for the company. With a unified incentive plan, you can bring every department into the same degree of alignment. Imagine your general counsel asking for less extraneous legal review in order to cut costs
• Resource allocation serves the company, rather than individual silos. If a department with its own compensation plan hits its (unique) metrics early, members of that team have no incentive to pitch in elsewhere; their bonuses are secure. But if everyone’s incentive depends on the entire company’s performance, get ready to watch product leads offering to share developers, unprompted.

This approach can only be taken so far: I can’t imagine an incentive system that doesn’t reward salespeople for individual performance. And while everyone benefits when things go well, if your company misses its goals, nobody should have occasion to celebrate. Everybody gets dinged if the company doesn’t meet its goals, no matter how well they or their departments performed. It’s a tough pill to swallow, but it also important preventive medicine.

Book Short:  Required Reading, Part II

Every once in a while, a business book nails it from all levels.  Well written, practical, broadly applicable to any size or type of organization, full of good examples, full of practical tables and checklists.   The Leadership Pipeline, which I wrote about here over six years ago, is one of those books — it lays out in great and clear detail a framework for understanding the transition from one level to another in an organization and how work behaviors must change in order for a person to succeed during and on the other side of that transition.  In an organization like Return Path‘s which is rapidly expanding and promoting people regularly, this is critical.  We liked the book so much that we have adopted a lot of its language and have built training courses around it.

The book’s sequel, The Performance Pipeline (book, Kindle), also by Stephen Drotter but without the co-authors of the original book, is now out — and it’s just as fantastic.  The book looks at the same six level types in an organization (Enterprise Manager, Group Manager, Business Manager, Functional Manager, Manager of Managers, Manager of Others, and Self Managers/Individual Contributors) and focuses on what competencies people at each level must have in order to do their jobs at maximum effectiveness — and more important, in order to enable the levels below them to operate in an optimal way.

This book is as close to a handbook as I’ve ever seen for “how to be a CEO” or “how to be a manager.”  Coupled with its prequel, it covers the transition into the role as well as the role itself, so “how to become a CEO and be a great one.”  As with the prequel, the author also takes good care to note how to apply the book to a smaller organization (from the below list, usually the top three levels are combined in the CEO, and often the next two are combined as well).  No synopsis can do justice to this book, but here’s a bit of a sense of what the book is about:

• Enterprise Manager:  role is to Perpetuate the Enterprise and develop an Enterprise-wide strategic framework – what should we look like in 15-20 years, and how will we get the resources we need to get there?
• Group Manager:  role is to manage a portfolio of businesses and develop people to run them
• Business Manager:  role is to optimize short- and long-term profit and develop business-specific strategies around creating customer and stakeholder value
• Functional Manager:  role is to drive competitive advantage and functional excellence
• Manager of Managers:  role is to drive productivity across a multi-year horizon, and focus
• Manager of Others:  role is to enable delivery through motivation, context setting, and talent acquisition
• Self Managers/Individual Contributors:  role is to deliver and to be a good corporate citizen

I could write more, but there’s too much good stuff in this book to make excerpts particularly useful.  The Performance Pipeline is another one of those rare – “run, don’t walk, to buy” books.  Enjoy.  For many of my colleagues at RP – look out – this one is coming!

Book Short: Plain Talk

An HR rock star I met with recently told me that “You can say anything you want to your people, as long as it’s true,” which of course is great advice.  Plain Talk: Lessons from a Business Maverick (book, kindle), by Ken Iverson, the long-time CEO of Nucor, pretty much embodies that.  If you’re not familiar with Nucor, it’s a steel company – right, steel – and the most successful one of the last 50-75 years, at that.  You may think an industrial company like this offers no lessons for you.  If so, you are wrong.

The reason Nucor has been so successful, if you believe their long time leader, is that they run the people side of their business differently than most companies like them.  Reading this book from the perspective of a knowledge worker business CEO was particularly interesting, since I had to transform my frame of reference a bit (and do a little mental time travel as well) in order to understand just how revolutionary Nucor’s practices were at the time.

But then I realized – they’re still revolutionary today.  How many companies – even the most progressive ones – don’t have performance reviews because they don’t need them in order to create a high performing environment?  Companies that spend a good percentage of their time and energies thinking about how to get their employees to do their best work, as opposed to focusing only on the goals of the business, do better than those who don’t.  It doesn’t matter what industry you’re in.  As Patrick Lencioni would say, you can outbehave the competition.

Plain Talk is a really short book, and a good, authentic read if you’re a leader who cares about your people and wants to learn a few nuggets here and there from one of the 20^th century masters of that discipline.  Anyone that can link a high degree of delegation to authority has a story worth telling.

Book Short:  Getting to MVP

Usually, when we hear the term MVP, we think Most Valuable Player.  But in my line of work, that acronym has come to mean something entirely different:  Minimum Viable Product.  Running Lean: Iterate from Plan A to a Plan That Works, by Ash Maurya, is an incredibly useful, practical how-to guide for any entrepreneur with an idea from concept through to MVP, or the smallest bit of functionality that you can get customers to pay for. This is one of the best books I’ve read that encapsulates most of the contemporary thinking and writing about product development in the early stages of a startup’s life from thought leaders like Steven Gary Blank and Eric Ries.

I read the book recently, as I was writing Startup CEO (original outline here), and I quoted liberally from it, including using his Lean Canvas graphic:

The basic principle behind the Lean Canvas is that the old way of doing a business plan was a ton of up front planning work, assuming you’re right, then building to spec.  The new way of doing a business plan is a really short series of hypotheses on a single page, then the time is spent de-risking the plan by systematically testing each element of it out.  The book includes several lists of checklists that walk you through how to test each box on the Lean Canvas.  As I’ve written about before, checklists are a really powerful management tool.

This is an essential read for entrepreneurs just starting a business.  But it’s also an excellent read for anyone running a growth company.  We have adopted more and more agile/lean methodologies over time at Return Path, and all of our product teams use the Lean Canvas with any major new features and projects.

(Side note – I’m writing this post on Friday, May 10, which is the 9th anniversary of my publishing this blog – 760 posts and one draft book later, it’s still an integral part of my business life!)

Years ago, I heard then General David Petraeus give a talk to a small group of us about leadership. He was literally coming to us live from his command center in Iraq or Afghanistan when he was running the whole theater of war over there. I realize he subsequently had some tarnish on his reputation after pleading guilty to a misdemeanor around handling classified information, but the main thrust of his talk, his Formula for Strategic Leadership, still stands as one of the more memorable talks on leadership I’ve ever heard and is no less relevant as a result.

Given that I still remember it vividly 14-15 years later, I thought I’d recreate it here with my own annotations after the four principles. It’s a simple 4-step formula:

1. Get the big ideas right. Obviously, you aren’t going to go down in history as a great leader if you consistently get the big picture wrong. That doesn’t mean you have to be right about everything and every detail. But if you pick the wrong market, bet on the wrong approach, happen to get your timing wrong by a few years…it’s hard to win.
2. Communicate them up and down the organization. Every mature leader knows that ideas and plans only go so far if they stay in your head or get filtered down through leadership teams. For your values to take root, for your strategy and strategic choices to make sense, and for people in the organization to be able to connect their daily execution to your company’s north star, you need to spend a lot of time communicating those things throughout the organization. Different groups, different meetings, different channels. And then, when you’re finally exhausted and sick of hearing yourself say those things over and over and over again…keep saying them.
3. Personally oversee their implementation. Leaders who throw things over the proverbial wall — “here’s what to do, now go do it while I move on to something else” — are not really strategic leaders. The devil is in the details. If you can’t bother to spend a few minutes overseeing the implementation of your strategy and carefully watching when and how it works and doesn’t (see next item), you may be a good visionary, but you’re not really a strategic leader.
4. Memorialize and institutionalize best and worst practices. This is where so many leaders fall down on the job. When something in your organization wraps up — a launch, a quarter, a project — you have to do a retrospective, curate learnings both good and bad, and publish them. That way your whole organization can have a growth mindset as a system.

There are about a zillion books on leadership out there. Most of them are probably between 200 and 400 pages long. While they may all have variations on this theme and colorful examples behind them, this still rings true for me as the essential formula for strategic leadership.

Book Short (and great concept): Moments of Truth

TouchPoints:  Creating Powerdul Leadership Connections in the Smallest of Moments, by Douglas Conant, former CEO of Campbell’s Soup Corporation, and Mette Norgaard (book, kindle), is a very good nugget of an idea wrapped in lots of other good, though only loosely connected management advice around self awareness and communication — something I’m increasingly finding in business books these days.

It’s a very short book. I read it on the Kindle, so I don’t know how many pages it is or the size of the font, but it was only 2900 kindles (or whatever you call a unit on the device) and only took a few Metro North train rides to finish.  It’s probably worth a read just to get your head around the core concept a bit more, though it’s far from a great business book.

I won’t spend a lot of time on the book itself, but the concept echoes something I’ve been referring to a while here at Return Path as “Moments of Truth.”  Moments of Truth are very short interactions between you and an employee that are high impact and, once you get the hang of them, low effort.  At least, they’re low effort relative to long form meetings.

Here are a few thoughts about Moments of Truth:

• They are critical opportunities to get things both very right and very wrong with an employee
• They are more powerful than meets the eye – both for what they are and because they get amplified as employees mention them to other employees
• They can come to you (people popping into your office and the like), you can seek them out (management by walking around), and you can institutionalize them (for example, one of the things I do is call every employee on their Return Path anniversary to congratulate them on the milestone)
• They are no different than any other kind of interaction you have, just a lot shorter and therefore can be more intense (and numerous)
• Their use cases are as broad as any management interaction — coaching, positive or negative feedback, input, support, etc.

What can you as a manager or leader do to perfect your handling of Moments of Truth?

First, learn how to spot them when they come to you, and think about a typical employee’s day/week/month/year to think about when you can find opportunities to seek them out.  Their first day on the job.  When they get a promotion.  When they get a great performance review, or new stock options.  Maybe when they get a poor performance review or denied a promotion they were seeking.

Second, learn to appreciate them and leave space for them.  If you have zero free minutes in every single day, you not only won’t have time to create or seek out Moments of Truth, you’ll be rushed or blow them off when they come to you.

Finally, like everything else, you have to develop a formula for handling them and then practice that formula.  The book does talk about a formula of “head, heart, hand” (e.g., being logical, authentic, and competent) that’s not bad.  Although I’d never thought about it systematically before writing this post, I have a few different kinds of Moments of Truth, and each one has its own rhythm to it, and its own regular ending.

But regardless of how you handle them, once you think about your day through this lens, you’ll start seeing them all over the place.  Recognize their power, and dive in!