Managing by Checklist

The Checklist Manifesto:  How to Get Things Right, started as an article in The New Yorker a few years ago by Atul Gawande and then turned into a book as well (book, Kindle).  I haven’t read the book; the story in the article is about life-and-death issues and how Intensive Care Units in hospitals work most successfully when they “manage by checklist” — they keep thousands of small steps performed by different people in order.

The story is very telling for business as well and reminiscent of David Allen’s productivity books, Getting Things Done: The Art of Stress-Free Productivity and Ready for Anything: 52 Productivity Principles for Work and Life. The reality as far as I’m concerned is that no matter who you are, no matter what role you play in an organization, my guess is that there are some routine or recurring tasks you perform where having a tight checklist is a no-brainer.  Between eliminating missed steps and increasing productivity by not having to reinvent the wheel…we may not be saving lives in dramatic fashion in most businesses, but we all have jobs to do and want to do them as well as possible.

Thanks to my colleague Tami Forman for pointing me to this.  At a minimum, the article is a great read.  And oddly, I had this post drafted for quite a while – I decided to post it today when I saw Jeff Ogden’s post about the same topic in reference to yesterday’s emergency landing at JFK.

A Little Quieter Than Usual, For Now

As many of you know, I’m writing a book called Startup CEO:  a Field Guide to Building and Running Your Company, which is due to the publisher in a few weeks.  I’d originally thought the book would be an easy project since the idea was to “turn my blog into a book.”  But then it turned out that for the book I wanted to write, I’d only written about 1/3 of the content on the blog already!

So the past few weeks I’ve been writing my brains out.  I now have a nearly 100,000 word draft, which needs to be edited down quite a bit, charts and tables inserted, outside contributors added in.

For the next handful of weeks, I’m going to post a bit less frequently than usual – probably every other week – as a result.  But once I get through this period, I’ll come roaring back with TONS of new content written for the book!

Blogiversary, Part VII

Today marks the seventh anniversary of OnlyOnce.  I haven’t marked the date with a post in three years, but here was my last such post (with links to prior posts in it).  In sum up until now, my reasons for blogging have been written up as:

• “Thinking” (writing short posts helps me crystallize my thinking)
• “Employees” (one of our senior people once called reading OnlyOnce “getting a peek inside Matt’s head)
• My book reviews help me crystallize my takeaways from books and serve as a bit of a personal reference library
• I like writing and don’t get to do it often

After seven years, though, I’m going to add another important point of value for me for writing OnlyOnce:  now, at 672 posts (including 27 that are scheduled but not yet posted – easy a record for me), this blog now serves as a repository for me of my own lessons learned, best practices, anecdotes, and aphorisms.  Thanks to Lijit, it’s easy for me and others to search.  Thanks to the new WordPress format and design by my friends at Slice of Lime, the categories and tagging make it much easier to navigate.

I probably get one question a week from a fellow CEO or prospective entrepreneur or employee that, instead of typing out an answer or setting up a meeting, I can actually just send a link as a starting point.  Sometimes there are follow-up questions, sometimes there aren’t.  But the blog is proving to be a very efficient form of documentation.

I’ve always thought my grandmother was a remarkable person. At age 92 (sorry to publish it, Gma), she is pretty hip — drives a Lexus, plays a mean game of bridge, carries a cell phone, and until recently, used WebTV.

She was getting tired of the slow connection via dial-up, so Mariquita and I gave her an old laptop we had and installed a cable modem (I have to commend Cablevision of Westchester/Optimum Online on a very smooth and easy installation process), so now she’s the world’s newest computer user. Those of us who work with computers every day take some of the basics for granted, but if you’ve never used Windows or a mouse before, this stuff is not easy to learn.

But I’m proud to say that Grandma Hazel, after three short days, is using Outlook, used Return Path to announce her change of email address to her address book, set up 1-click on Amazon and bought a couple books, read my blog, and even subscribed to receive email alerts when I post.

After 5 years of WebTV, I think she’s in for a real treat with how fast the web can be and how much there is to explore out there. And if anyone can figure out how to use this stuff, it’s her. Welcome to the web and to blogs, Gma!

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.

Jim Collins, in both Good to Great and Built to Last talked about the BHAG – the Big, Hairy Audacious Goal – as one of the drivers of companies to achieve excellence.  Perhaps that’s true, especially if those goals are singular enough and simplified enough for an entire company of 100-1000-10000 employees to rally around.

I have also observed over the years that both star performers and strong leaders drive themselves by setting large goals.  Sometimes they are Hairy or Audacious.  Sometimes they are just Big.  I suppose sometimes they are all three.  Regardless, I think successfully managing to and accomplishing large personal goals is a sign of a person who is driven to be an achiever in life – and probably someone you want on your team, whether as a Board member, advisor, or employee, assuming they meet the qualifications for the role and fit the culture, of course.

I’m not sure what the difference is between Hairy and Audacious.  If someone knows Jim Collins, feel free to ask him to comment on this post.  Let’s assume for the time being they are one and the same.  What’s an example of someone setting a Hairy/Audacious personal goal?  My friend and long-time Board member Brad Feld set out on a quest 9 years ago to run a marathon in each of the 50 states by the age of 50.  Brad is now 9 years in with 29 marathons left to go.  For those of you have never run a marathon (and who are athletic mortals), completing one marathon is a large, great and noteworthy achievement in life.  I’ve done two, and I thought there was a distinct possibility that I was going to die both times, including one I ran with Brad .  But I’ve never felt better in my life than crossing the finish tape those two times.  I’m glad I did them.  I might even have another one or two in me in my lifetime.  But doing 50 of them in 9 years?  That’s a Hairy and Audacious Goal.

For me, I think the Big goal may be more personally useful than the Hairy or Audacious.  The difference between a Big goal and a Hairy/Audacious one?  Hard to say.  Maybe Hairy/Audacious is something you’re not sure you can ever do, where Big is just something that will take a long time to chip away at.  For example, I started a quest about 10-12 years ago to read a ton of American history books, around 50% Presidential biographies, from the beginning of American history chronologically forward to the present.  This year, I am up to post-Civil War history, so roughly Reconstruction/Johnson through Garfield, maybe Arthur.  I read plenty of other stuff, too – business books, fiction, other forms of non-fiction, but this is a quest.  And I love every minute of it.  The topic is great and dovetails with work as a study in leadership.  And it’s slowly but surely making me a hobby-level expert in the topic.  I must be nearing Malcolm Gladwell’s 10,000 hours by now.

The reason someone sets out on a personal quest is unclear to me.  Some people are more goal-driven than others, some just like to Manage by Checklist, others may be ego-driven, some love the challenge.  But I do think that having a personal quest can be helpful to, as Covey would say, Sharpen the Saw, and give yourself something to focus personal time and mental/physical energy on.

Just because someone isn’t on a personal quest doesn’t mean they’re not great, by the way.  And someone who is on a quest could well be a lunatic.  But a personal quest is something that is useful to look for, interesting and worth learning more about if discovered, and potentially a sign that someone is a high achiever.

My name is Matt Blumberg. I am a technology entrepreneur and business builder based in New York City. I am CEO of Markup AI, the leading provider of Content Guardian Agents to companies of all sizes looking to scale their use of AI to generate content smartly and safely. We are defining a new category in the Generative AI space and crushing it.

Before that, I started a company called Bolster, which was an on-demand executive talent marketplace.  We created a new way to scale executive teams and boards aimed at early and mid-stage tech companies. The business sort of worked and sort of didn’t work. We wound it down in 2025 and decided to focus on helping the portfolio companies we invested in via Bolster Ventures and help our friends with talent referrals on a more informal basis.

My longest career stint was Return Path, a company I started in 1999, 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 followed that by co-authoring a book with a number of my fellow executives from Retutrn Path and Bolster called Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams; as well as the second edition of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors along with Brad Feld and Mahendra Ramsinghani. I hosted a podcast called The Daily Bolster, with over 200 micro-episodes (mostly 5-6 minutes long) where I interview other CEOs to share their stories and hacks.

I have been married for over 25 years to Mariquita, who is, as I tell her all the time, one of the all-time great wives. We have three great kids now in their late teens, 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. I hosted a limited edition podcast series called Country Over Self which explored the topic of virtue in the Oval Office along with a dozen prominent presidential historians.

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.

RSS Advertising

This is two-day-old news by now, but in case you missed it, we just announced than we – Return Path – are partnering with Feedburner to take RSS advertising to the next level (coverage here, here, and here).

As you probably know if you receive my feed or other ones, Feedburner has been doing some experimenting with ad units at the bottom of feeds for months now, first using Amazon and more recently Google AdSense to serve up ads.  And as you may know if you look at ads closely, neither of those services has done a great job making the ads truly relevant.  I can’t tell you, for example, the number of times I write a posting about a book, and the ad has absolutely nothing to do with books, let alone the book or author I’m writing about.  My favorite one was a posting Fred wrote called “Why a Conservative Turns Liberal,” with an ad called “Meet Conservative Singles” — probably not Fred’s intent, although it certainly brought a smile to my face.

Anyway, what we’re doing with Feedburner is very simple.  Our Customer Acquisition Solutions group sells lead generation products to hundreds of advertisers each month in the form of either email list rental or web-based lead gen based on categories of interest expressed by consumers who sign up with our Postmaster Direct service.  Feedburner has categorized a number of the 100,000+ feeds they publish as “Consumer Electronics” or “Computing and Technology,” which are two of the strongest categories we have, both in terms of consumers and in terms of advertisers.

So our salesforce is going to add “RSS” as an option for our advertisers in those categories, and we will work with Feedburner to insert demo-targeted ads into select feeds.  We and Feedburner both acknowledge this is an experiment, but we’re very optimistic about the results: the demographics should line up perfectly and provide our advertisers with a new channel as part of their existing campaigns.  I’m sure Dick or someone else at Feedburner will blog about it as well at some point, and if we learn anything  truly interesting after the first few months, we’ll let the world know!

Last week, I wrote about Bringing People Along for The Ride by involving people in the process of ideating and creating change in your organization. That’s the most important thing you can do to make it easy for people to handle change.

But what about the people you don’t or can’t bring along for the ride in that way? If you organization has more than 10 people in it, there will inevitably be people where you’re IMPOSING CHANGE ON THEM. And honestly, even people who are involved in designing change still have to live through its impact.

Today’s post is about managing the actual impact.

The best thing you can do as a leader in helping your organization navigate change is to be empathetic to the fact that, even if you involve people in designing the solution, you are, in fact, making changes to their day to day lives. One of the best books I’ve ever read on this is Transitions: Making Sense of Life’s Changes, by William Bridges. And while there’s a lot more to the book than this one point, I’ll share two graphics from the book and its offshoots that say a lot.

Bridges’ basic concept is to think about changes as having three phases. The end of the old thing, the beginning of the new thing, and the time between the two – when the new thing has been announced, but the it hasn’t taken effect yet. Here’s a look at one powerful graphic on this front, where the point is that productivity (the red line) tanks briefly during the time of uncertainty with the overlay of human emotions at each phase.

Next let’s look at Bridges’ model for how to think about these three phases. This part is critical. They are not discrete phases, where everyone finished “ending” and moves onto “neutral” and then moves on to “new.” From the moment a change is in the offing, until after the change is implemented, people are simultaneously operating in all three zones at the same time, in different proportions.

That means when change starts, you’re already helping them understand that there will be a period of confusion followed by a bright new future. And it means that even when the bright new future has arrived, you’re still mindful of the confusion as well as the things that were special about the past.

I wrote about this a little bit in the second edition of Startup CEO and in this blog post on transitions and integration. The paragraph I’ll call out is:

For ourselves as leaders and me as CEO, knowing most of us would leave almost immediately post-deal, I wanted to have as elegant an exit as possible after 20 years. Fortunately, I had a good partner in this dialog in Mark Briggs, the acquiring CEO. Mark and I worked out rules of engagement and expenses associated with “the baton pass,” as we called it, that let our execs have the opportunity to say a proper goodbye and thank you to our teams, with a series of in-person events and a final RP gift pack. This was a really important way we all got closure on this chapter in our lives

The Baton Pass is a helpful analogy to think about this process. In a relay race, the two runners run alongside each other for a little while until they are at the same pace and proper spot, THEN one hands the other the baton. It’s the time when the past and the future collide, in a neutral zone. When you mark the great things and painful learnings that came before and launch into the bright new future.

The best thing you can do as a leader who is driving change through an organization is to Bring People Along for the Ride. Part of that is involving people in the creation of the new world. But it’s also recognizing that humans have to process change, and that takes time.

Happy Leap Day!

One of the better books I’ve read in the last 6 months is James Clear’s Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones, which provides a great framework around habits. It’s worth a read, whether you’re talking about business habits/routines or personal ones. This isn’t a book review, but quickly while I have you – here’s a summary of his “laws”:

HOW TO CREATE A GOOD HABIT
The 1st Law: Make It Obvious
The 2nd Law:Make It Attractive
The 3rd Law: Make It Easy
The 4th Law: Make It Satisfying

HOW TO BREAK A BAD HABIT
Inversion of the 1st Law: Make It Invisible
Inversion of the 2nd Law: Make It Unattractive
Inversion of the 3rd Law: Make It Difficult
4th Law: Make It Unsatisfying

Add to that my other key takeaway, which is that you have to tie habits not just to outcomes but to identities, and…great book! Anyway, my story today is about decisions, and I’m going to quote James Clear’s email newsletter here, at the end of which he credits Tim Ferriss for sparking his thinking. So this is, what, third hand thinking. But it’s a great way to think about decisions, something I’ve written about a lot, including here.

I think about decisions in three ways: hats, haircuts, and tattoos.

Most decisions are like hats. Try one and if you don’t like it, put it back and try another. The cost of a mistake is low, so move quickly and try a bunch of hats.

Some decisions are like haircuts. You can fix a bad one, but it won’t be quick and you might feel foolish for awhile. That said, don’t be scared of a bad haircut. Trying something new is usually a risk worth taking. If it doesn’t work out, by this time next year you will have moved on and so will everyone else.

A few decisions are like tattoos. Once you make them, you have to live with them. Some mistakes are irreversible. Maybe you’ll move on for a moment, but then you’ll glance in the mirror and be reminded of that choice all over again. Even years later, the decision leaves a mark. When you’re dealing with an irreversible choice, move slowly and think carefully.

As someone who loves hats, has had (and seen) his fair share of bad haircuts, and has a tattoo, I can totally relate!

Agile Reading

While not exactly a laugh a minute, Lean Software Development:  An Agile Toolkit, by Mary and Tom Poppendieck, is a good read for anyone who is a practitioner of agile development — or anything agile.  (Note:  if you want a laugh a minute, read Who Moved My Blackberry?, which as Brad says, is hilarious — kind of like The Office in book form).

As I wrote about here and here, Return Path now does both agile development and agile marketing.  The book draws many interesting comparisons between manufacturing and engineering, which I found quite interesting, and not just because I’m a former management consultant — there’s something that’s just easier to visualize about how an assembly line works than about how code is written.  The foundation of the book is writings and sidebar anecdotes about 22 Tools, all of which are helpful to understand the principles which underly and power a successful agile process.

Concepts such as seeing and eliminating waste, empowering a team while still managing to lead it, and why small-batch work and application of the theory of constraints makes sense across the board are made easy to understand and easy to apply by the authors.

Thanks to my colleague Ed Taussig for this book.