Category

Startup CEO

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….

Double Book Short: Framework of Frameworks

I love me a good framework. And Geoffrey Moore is the kind of good product/marketing frameworks for technology companies. Moore’s Zone to Win: Organizing to Compete in an Age of Disruption is a must-read for anyone managing a larger technology organization (start reading it when you get to 200-250 people – it’s never too early to worry about disruption). More important, it’s really a companion book or coda to Escape Velocity: Free Your Company’s Future from the Pull of the Past, so if you haven’t read that one, start there and read both sequentially. Zone to Win is quite short and punchy, and it doesn’t disappoint. I can’t believe is that I never blogged about Escape Velocity before since 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…

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…

The Concept of the Operating Philosophy

I’ve always been a big believer in the Operating Framework and the Operating System as two of the management underpinnings behind every well run company. The Operating Framework is the company’s Mission, Vision, Values, Strategic Objectives, and Key Metrics. Companies have all sorts of different labels for this, from Balanced Scorecard to Salesforce’s V2MOM to Patrick Lencioni’s 6 Questions. It’s what you have to define up front, refresh annually, and tweak quarterly so that people in the company are aligned and know where you’re going. The Operating System, as I wrote extensively about in Startup CEO, is the collection of practices, meetings, mailing lists, routines/rhythms, and behaviors that your company and team use and depend on to run the business…

Second Lap Around the Track

I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap. Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is…

What a CEO Should Do

Fred Wilson wrote an iconic blog post years ago entitled What a CEO does. In it, he outlined three broad themes: A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank. I wrote a response in a post entitled What Does a CEO Do, Anyway?, in which I added some specificity to those three items and added three key behaviors of successful CEOs. I also added to Fred’s list when I wrote Startup CEO, CEOs have to build and lead a board of directors, CEOs have to manage…

Open All-Hands Meetings

I love stealing/borrowing other people’s good ideas for management and leadership when they’re made public, and I always encourage others to do so from me. I call it “plagiarizing with pride.” So I was intrigued when I saw a new way of doing all-hands meetings published by my friend Daniel Odio (DROdio) on his founder community called FounderCulture. You can see the original post here. We’ve experimented with different formats and cadences for all-hands meetings over the years. They tend to vary with the size of the company and complexity of the material to cover. Larger companies usually fall into the rhythm of doing quarterly all-hands meetings sometime after the end of the quarter, usually around a Board meeting, with…

Book Short: New to the Canon of Great CEO Books

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…