I am fortunate in my current job to spend a lot of time talking to other founders and CEOs. I mentor and coach them, my company and I help counsel them on executive and board searches, and I spend time with them at conferences and seminars. Even when I am giving them advice, I always take time to learn what they’re doing, what works, and what doesn’t work. I’ve noticed a consistent set of behaviors and practices common among the successful founder operators – the ones who go on to lead their companies through multiple chapters of growth and sometimes never hire the “seasoned operator” to come in and take over. #1 – They are students of the game. It’s…
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Entrepreneurship
My end of year routine (Taking Stock, Part III)
I have an end of year work routine that’s a pull-up and self-assessment. I’ve been doing this for years, and I’ve written about its evolution in Part I and Part II of this series. I’ve always taken a few minutes at this time of the year to ask myself these four questions: Am I having fun at work? Am I learning and growing as a professional? Is my work financially rewarding enough, either in the short-term or in the long-term? Am I having the impact I want to have on the world? If I answer at least 2.5 of these questions as yes, I feel like things are on track. If I am below that, or even at 2.5 sometimes,…
What Does Great Look Like in a CMO?
(This is the second post in the series… the first one When to Hire your first Chief Marketing Officer is here). Whether you have someone in your company that can level up to greatness or you need to bring in a CMO, the characteristics and skills of a great CMO you should aspire to include some of the following. A great CMO understands that the marketing budget starts with drivers and business results and works backwards in a modular way to spend, not the other way around. Yes, they will get some resources but rather than spend that money to fill in the gaps on their team to make the Marketing function strong or powerful, they’ll look at the business…
Book Short: It’s All About Creative Destruction
I was excited to read Launchpad Republic: America’s Entrepreneurial Edge and Why It Matters, by Howard Wolk and John Landry the minute Brad sent it to me. I love American history, I love entrepreneurship, and I’m deeply concerned about the health of our country right now. I have to say…on all fronts, the book did not disappoint! The authors make several points, but the one that sets the tone for the book is that like our country’s origins and culture in general, entrepreneurship is itself rebellious. It’s about upstarts challenging the status quo in some way or other with a better way to do something, or with a new thing. The balance between protecting private property rights and allowing for…
How to engage with Your CRO
(Post 4 of 4 in the series on Scaling CROs – other posts are, When to Hire your First Chief Revenue Officer, What Does Great Look like in a Chief Revenue Officer and Signs your Chief Revenue Officer isn’t Scaling) Assuming your CRO is on track and scaling with the company so that you’re not having to mentor or coach them, I’ve found a few ways to engage with the CRO that have been particularly fruitful. Here are a few tips on making every moment with your CRO well-spent. One of the easiest ways to carve out quality time with your CRO is during travel time, or in and around events. Particularly if you’re a B2B company that engages with…
Startup Boards: VCs and CEOs need to do their jobs!
Was anyone else as appalled as I am by the contents of Connie Loizos’s recent article, Coming out of COVID, investors lose their taste for board meetings? The stories and quotes in the article about VCs reducing their interest and participation in Board meetings, not showing up, sending the junior associate to cover, etc. are eye opening and alarming if widespread. The reasons cited in the article are logical—overextended VCs, Zoom fatigue, and newbie directors. Connie’s note that “privately, VCs admit they don’t add a lot of value to boards” is pretty funny to read as a CEO who has heard a ton of VCs talk about how much value they add to boards (although the good ones DO add a…
The Impact of a Good Coach
I’m pretty close to the executive coaching world. My wife Mariquita is an extraordinary CEO coach. I’ve worked for decades with Marc Maltz from Hoola Hoop, who helped me transform everything about how I lead organizations. I’ve been friends with Jerry Colonna of Reboot fame for years (I did a fun podcast with Jerry last year called “Everyone is Scalable). I’m pretty good friends with Chad Dickerson. Bolster’s marketplace helps place CEO coaches and even has a programmatic approach to coaching and mentoring called Bolster Prime. The list goes on. My friend Mitch, a fellow baseball coach, gave me a fun book a couple years ago that is a page-a-day called Coach: 365 Days of Inspiration for Coaches and Players,…
Best and Worst Practices (Plus FAQs) for Layoffs
Short of declaring failure and shutting down your company, laying off employees is the worst thing you may have to do as a startup CEO. I’ve had to lay people off on three separate occasions. It was difficult and emotional—those days were the worst of my career, and probably rank in the top 10 worst days of my life, period. This isn’t firing for cause—employees aren’t being asked to leave because of their own failings. They’re being asked to leave because the company can no longer afford to keep them. It’s not their fault. It’s a truly awful process. Some CEOs will fall into the trap of thinking that because it’s invariably messy, it doesn’t matter how you do it….
The Evolution of Feedback in Our Organizations
Across 22 years and two companies now, our system of giving performance feedback has evolved significantly. I thought I’d take a pass at chronicling it here and seeing if I had any learnings from looking at the evolution. Here’s how things evolved over the years: Written performance reviews. The first year of Return Path, we had a pretty standard process for reviews. They were more or less “one-way” (meaning managers wrote reviews for their direct reports), and they only happened annually. Written 360 reviews. We pretty quickly moved from one-way reviews to 360s. I wrote about this here, but we always felt that being able to give/receive feedback in all directions was critical to getting a full picture of your…
What Men’s Rooms Can Teach Us About Leadership and Management
I hope this post doesn’t gross anyone out or offend anyone. I admit it’s a little weird, and that it’s more accessible to men. Hopefully everyone can get my point, even if men get it a bit more. I’m channeling Brad as I write this. So bear with me. Here is a picture of a men’s room with floor mats under the urinals. The difference between using a men’s room that has floor mats and using a men’s room that does not have floor mats is profound in multiple ways. I’ll leave out the specifics, but you can imagine the comparative experiences if you haven’t had one or both. A really good floor mat, from a quick scan of Amazon…
Our Operating Philosophy – the Mostly Self Managed Organization (MSMO)
Last week, I wrote about the concept of the Operating Philosophy, and how it fits with a company’s Operating Framework and Operating System and defines the essence of who you are as a company…what form of company you are. While we had a loose Operating Philosophy at Return Path, we never really crisply articulated it, and that caused some hand-wringing at various points over the years, as different people interpreted our “People First” mantra in different ways. So this time around at Bolster, we’re trying to be more intentional about this up front. We have labeled our company a “Mostly Self Managed Organization” or MSMO (pronounced Miz-Moh). We made those up. Our Operating Philosophy – we are a Mostly Self-Managed…