Browsing posts in: Management & Leadership

Some of the best management advice I’ve seen this year from an Imgur product director

One of the best posts of management advice I’ve seen this year so far is, “21 management things I learned at Imgur,” from Sam Gerstenzang, a former product director at Imgur now at the tech investment firm a16z, which reminded me  of and reinforced a lot of hard lessons I’ve learned over the years.

There’s so much in this succinct piece that’s valuable but a handful of the first three are really hitting home right now (I’m dealing with an unmotivated person on a side project):

1. It’s terribly difficult to manage unmotivated people. Make your job easier and don’t.

2. Different people need different kinds of management. Be adaptable to figure out what drives each person’s best performance.

6. Fire quickly. If you don’t fire bad performers fast, you’re at risk of losing your good performers. Don’t underestimate the effect bad performers have on good performers. Your team will likely move faster even with fewer bodies. Finally, firing for bad performance is easier than having to fire good people because you’ve run out of money, so fire the bad people before you have to fire the good people too.

Check out the full list and save it to back to periodically. Repetition is sometimes necessary to learn these hard management lessons.





Quote of the week: “When you say ‘no’ to something, you are saying ‘yes’ to something else.”

This past week I was struck by a quote from Tim Stringer on the Coaching for Leaders podcast:

“When you say ‘no’ to something, you are saying ‘yes’ to something else.”

I’ve heard and believed similar things, but not heard this so succinctly and perfectly. Especially in our society — and doubly so in DC — where it’s a badge of pride to CHOOSE to be ‘constantly busy.’ Most people don’t acknowledge much of what we do is a *choice* to be busy when it comes to work-life balance.

I, and a lot of people, think if we’re not running at 120% capacity, it’s very easy to say yes to things just to fill up your calendar but it’s good to have the bandwidth and space to say ‘yes’ to impromptu or urgent things, rather than having to book and plan out your ‘extra/side project’ schedule months in advance (which I actually just did for the next quarter… I’m glad I’m planning it, but after writing this realize I might need to just book 10% time for new/experimental things).

I’m right now wrestling with some side projects that I might need to wind down or walk away from because the initial commitment I offered has grown exponentially and unfortunately when other leaders in the organization have seen the extra work I’ve put in, they’ve lumped more on me, backed away and/or stepped down. I hoped that seeing someone putting in extra effort would inspire the culture and make the others reinvigorated to pull their fair share and work harder, but for some it’s had the opposite effect. There is one champion who I think is really excellent and working with me to improve the process and culture, and hopefully we can weather this storm and get some allies who will put in the time and effort needed. I’d hate to walk away from her getting re-inspired and her positive energy. Anyway that’s all to say, I’m thinking a lot about commitments, time, impact and how to choose wisely what to say yes and no to a lot lately so this quote struck me pretty hard at the right time.

If you don’t listen to the Coaching for Leaders podcast, you should check it out. It’s been one of my long-time favorites for podcasts on positive, realistic management approaches for all sorts of organizations.


How to become an expert in emerging technology: Own it. Do it. Talk about it.

I have no idea what I'm doing dog

Here’s some career advice I have to keep re-learning:

“Own it. Do it. Talk about it.”

I wrote this down on a scrap of paper while traveling last month and listening to podcasts but I can’t seem to find which one it came from and googling doesn’t provide any clarity (so forgive me whoever this is from but I found it particularly profound and something I regret not embracing in the middle of my career).

This is especially important in the emerging skill and digital technology areas. *Everyone* is learning as they go. The experts and ‘big names’ get elevated because they own it. They do it (and dive deep experimenting in it). *AND* they talk about it (what they learned, what worked, what didn’t, how to improve, etc.).

I did this really well early on and gained some notoriety as a early tech journalism blogger at Journerdism. As I continued through my career though and especially after I went really deep into mobile technology during my Fellowship at RJI, I started to retreat and feel burned by people who would take my work and ideas, and claim them as their own with no attribution or credit. I went out of my way to cite and praise those that came before me and give them credit and when people took my work and built upon it but didn’t share the credit it really bothered me and took a while to get over it. But eventually I learned that’s not how we move forward as a society and culture.

In a world of proprietary vs. open source, open source will always do more societal/cultural good, exponentially faster and stronger than closed systems. But you gotta check your ego, be open and willing to share and learn with others, even if it means sometimes someone will step on your face to climb above you while using your work. Sometimes they aren’t trying to hurt you when they step on you, they’re just trying to move things forward. The irony here is I can’t find who said the quote so I’m not properly attributing it, but I hope they’ll forgive me and take my appreciation and any impact sharing this forward makes as credit for making the world better.

Watch this: Inspirational and transformational management strategies from The Profit

The Profit

I’m not a reality TV junkie by any means, in fact, I avoid almost all of them (and most TV in general). But one show I’ve been hooked on over the past year has been The Profit, a CNBC show about turning around failing businesses with investor and consultant Marcus Lemonis who invests his own money, sweat equity and expertise to right the ship.

What I love about this show:

  1. As someone who’s dedicated his live to trying to fix, improve and impact legacy organizations from media to the government with varying levels of management, process and product issues, I really enjoy seeing Lemonis’ process and how he drops in to any type or size of organization– from Key Lime Pie bakers to car dealerships to a custom furniture family business — and applies a simple formula to fix it. And most of the time, he seems to pull it off.
  2. His simple formula is fantastic. Focus on improving: People. Process. Product.
  3. It’s real. Sometimes the deals don’t always work out or things explode and then end up in litigation after the business backs out of agreements or didn’t disclose debts or other issues. One of the things that drive me nuts about most reality shows is their predictable story arcs that make them seem scripted (and without a doubt, some are). The Profit doesn’t always have a happy ending and I appreciate the realness of that.
  4. Lemonis’ interpersonal skills have been really inspirational to me. The way he drops into these organization, finds allies, champions and diamonds in the rough, then raises them up and helps them rebuild were instrumental in my leadership strategy in the last year at the BBG. Most of the time, the core issue with the business is the people. Process and product are generally easier to fix. People are often the hardest thing to change in failing businesses, especially changing a culture or a hard personality (without just firing away the problem which sometimes you can’t). Often in the show (and in real life at these kind of flailing organizations) issues are caused by people who refuse to give up control, refuse to try a new way or hand over control to the next generation of leaders. So learning his tools and emotional intelligence strategies has been incredibly helpful for me as a manager.

Check it out on CNBC prime time, the web on Hulu (how I watch it).

Hold less meetings, get out of the way and ship more stuff.


One of the difficult things that I had to work on as I rose through the management ranks was managing communication. And specifically meetings.

When you move out of technology and into management your work creations are not a design or a website or a piece of documentation/white paper — they’re facilitating and expediting the teams that do that content creation.

Making that jump is really difficult for some — it was for me — part of me wanted to still be in code and design, and as I realized that I needed to get out of the way and step back and let the team do their jobs, I felt the need to have some sort of tangible ‘things’ for my time, and that started to become meetings. I started to feel that if I had a full schedule of meetings and was preparing and going to and leaving meetings I felt like I was doing my job well. It couldn’t have been further from the truth though, and luckily I learned this quickly thanks to some frank feedback and open communication lines with my team.

Discussing this with other young managers making the transition this seemed to be a common theme. The costs of chronic meetings isn’t just spent time not creating, it disrupts the energy of your day and your focus and ‘flow’, context shifting slows overall productivity and literally costs money by the minute like an Uber. We found solace and got better sharing our mastermind with each other about strategies and sharing amazing new management and work bible’s like Getting Real from 37 Signals:

Do you really need a meeting? Meetings usually arise when a concept isn’t clear enough. Instead of resorting to a meeting, try to simplify the concept so you can discuss it quickly via email or im or Campfire. The goal is to avoid meetings. Every minute you avoid spending in a meeting is a minute you can get real work done instead.

(Seriously, read the whole book, it’s a quick and awesome piece.)

Some people never grow out of this; one of the worst bosses of my life has a chronic problem with this and I tried to work with him on it, but he refused. (And thankfully is no longer my manager or anyone’s manager, luckily).

A recent HBR article reminded me of this challenge we all must fight — balancing doing productive work vs. holding many meetings — and they provided a great quick and easy test of four questions for deciding if it’s time to take everyone away from their work to hold a meeting:

  • Have I thought through this situation?
  • Do I need outside input to make progress?
  • Does moving forward require a real-time conversation?
  • Does this necessitate a face-to-face meeting?

And an easy flow chart of options for deciding if meetings are necessary:

Should I hold this meeting

How to exponentially impact the world — a recipe from “Bold” an inspirational book by Peter Diamandis and Steven Kotler

The 6 Stages of Exponential Growth from Peter Diamandis

The book “Bold: How to Go Big, Create Wealth and Impact the World” is the next big thing I’m excited about from Peter Diamandis, the Chairman of the X Prize, who helped create all sorts of futuristic amazing things like Singularity University, Hyperloop and Space X, and Steven Kotler. They prescribe to create ground-breaking, world-changing, exponential businesses (the kind Peter Thiel talks about in Zero to One) to focus on opportunities:

Digitalization. This idea starts with the fact that culture makes progress cumulative. Innovation occurs as humans share and exchange ideas. I build on your idea; you build on mine. This type of exchange was slow in the early days of our species (when all we had as a means of transmission was storytelling around the campfire), picked up with the printing press, then exploded with the digital representation, storage, and exchange of ideas made possible by computers. Anything that could be digitized—that is, represented by ones and zeros—could spread at the speed of light (or at least the speed of the Internet) and became free to reproduce and share.

Deception. What follows digitalization is deception, a period during which exponential growth goes mostly unnoticed. This happens because the doubling of small numbers often produces results so minuscule they are often mistaken for the plotter’s progress of linear growth. Imagine Kodak’s first digital camera with 0.01 megapixels doubling to 0.02, 0.02 to 0.04, 0.04 to 0.08. To the casual observer, these numbers all look like zero. Yet big change is on the horizon. Once these doublings break the whole-number barrier (become 1, 2, 4, 8, etc.), they are only twenty doublings away from a million-fold improvement, and only thirty doublings away from a billionfold improvement. It is at this stage that exponential growth, initially deceptive, starts becoming visibly disruptive.

Disruption. In simple terms, a disruptive technology is any innovation that creates a new market and disrupts an existing one. Unfortunately, as disruption always follows deception, the original technological threat often seems laughably insignificant. Take the first digital camera. Kodak took great pride in things like convenience and image fidelity. Neither were present in Sasson’s original offering. His camera took twenty-three seconds to snap and store a .01 megapixel, black-and-white photograph. Well, no threat there…

Demonetization. This means the removal of money from the equation. Consider Kodak. Their legacy business evaporated when people stopped buying film. Who needs film when there are megapixels? Suddenly one of Kodak’s once-unassailable revenue streams came free of charge with any digital camera.

Dematerialization. While demonetization describes the vanishing of the money once paid for goods and services, dematerialization is about the vanishing of the goods and services themselves. In Kodak’s case, their woes didn’t end with the vanishing of film. Following the invention of the digital camera came the invention of the smartphone—which soon came standard with a high-quality, multi-megapixel camera. Poof! Now you see it; now you don’t. Once those smartphones hit the market, the digital camera itself dematerialized.

It has me really thinking about life, my accomplishments and impact on the world.

Welcome to Kaizen Will

Kai Zen - "Good Change" in Japanese

Kai Zen – “Good Change” in Japanese

Welcome to Kaizen Will, a new site about living a life of continuous improvement.

I have to thank my parents for my curious thirst for knowledge and constantly improving nature; they were both teachers whom with modest means, medium salaries and resources constantly strove for excellence, balancing frugality with finding a high quality of life and sought constant improvement and education to achieve this.

Throughout my life those values have influenced my journey. When I finished my Masters degree at Northwestern University, I made a promise to myself that school was not over; I was just beginning my voyage of continuous, lifelong learning and improvement.

I couldn’t have envisioned how massive, rapid and constant change came (and still comes) to the media and technology industry. But embracing kaizen helps you face that challenge. It translates to “continuous improvement” or “good change.”

This constant thirst for knowledge was channeled into into (one of the early leading online media blogs), more than a decade of attending, speaking, leading and organizing workshops and training for the rapidly evolving media.

This practice also crosses over to my professional life. While at The Palm Beach Post, working as Interactive Projects Editor, a brilliant colleague, W. Mark Hartnett pointed me to the revolutionary business and management book, The Toyota Way, which discusses the practice of kaizen.

As I advanced in my career through project management and leadership positions, this principle continued to become a reoccurring theme in my life. From Jim Collins’ book Good To Great to getting certified as a scrum master building products with Agile processes — the same kaizen concept has been reinforced again and again in different forms and with different names.

This year I decided I wanted to get back on the horse and start creating some content and sharing my experiences and advice with the world. I wrestled with a lot of concepts for how to tackle my focus, but kept coming back to kaizen. How to change and evolve to get better and better and better. To go from having a good life, a good family, a good relationship to a great–the greatest life.

Will synonyms

And since I’m Will Sullivan, “Kaizen Will” seemed to fit perfectly.

The attitude.

The resolve.

The passion.

The discipline to create a life of continuous improvement.

Let’s start the journey and see where it takes us. :)

To start off, I believe I’ll focus on these Kaizen Will categories and topics (subject to change/grow/shrink as the blog evolves):

  • Management & Leadership – Throughout my career I’ve been fortunate to have some amazing mentors and bosses and a couple some terrible bosses — and I’ve learned immensely from both, as well as extensive study on how to develop as a manager and leader in the modern tech and media business and entrepreneurship world. I’ll share best practices, advice, lessons learned and things “I wish someone had told me” so that you can improve yourself.
  • Money & Personal Finance – Being fiscally responsible, frugal and smart about your spending, saving and investing helps give you the resources to enjoy time, stuff and share with people, so I’ll share what I’ve learned to help you get this in line.
  • People & Relationships – People are the most important part of my life. From inspirational mentors, family, friends to speakers, authors or even characters in fiction, our humanity and relationships are what helps humans to survive and thrive. Growing from a socially-awkward, introverted teenage nerd up to a professional executive has had it’s growing pains and plenty of bruises and bumps along the way. I’ll share what I’ve learned to help others on my journey, as well as stories about people who have been inspirational.
  • Travel & Adventures – Travel and finding adventures ‘exploring the infinite abyss’ is a huge part of my life. From finding quirky local secret spots to backpacking across Asia alone, I love exploring new cultures, places and perspectives. I’ll share some of my best practices and pro tips here.
  • Recommended Gear, Books & Stuff – I was raised rather frugally and to appreciate a Spartan, non-consumerist life, relish libraries and shared resources, so this definitely isn’t a shopping blog or anything, but also to appreciate and take care of the things you do purchase.
    • Best Purchases of … – The past few years I’ve really relished a few purchases that have changed or enhanced my life. These might not be indestructible “Buy It For Life” items, but they’ve really been great purchases that have added a lot of value for me.
    • Buy It For Life – Gear that will last your entire life (or close to it) that you can give to your grand kids (largely inspired by the BIFL Sub-Reddit I’m a huge fan of).
    • Treat Yo SelfLike Tom and Donna on Parks and Rec said, sometimes you gotta treat yo self. This is once-in-a-blue-moon stuff to splurge on that I’ve found worthwhile. They might not be ‘buy it for life’ or the best purchases, ever, but they were worth it on special occasions.

Welcome to Kaizen Will.

Let’s all get better together.