Category

Business

How to Engage with Your CFO

It’s fairly rare in a startup or scaleup that you, as a CEO or CXO (Chief [fill in the function] Officer) of any kind, will have significant one-on-one time with other members of the executive suite; instead, you’re most likely to spend time with the team in executive meetings, at offsites, or during all-company events. So, when you do get that one-on-one time it’s important to make sure that it’s not only productive, but that it builds a stronger relationship between you and the other person. As a CEO I learned that the best way to help people grow and develop, and to further develop a better understanding of each other, is to engage with them in a mix of…

Momentum and Confidence: Everything Matters

As I stared at a dugout of dispirited 14 year old boys Saturday afternoon in our tournament championship game, I found myself talking to my fellow coach Mitch about a book I’d read a few years ago (turns out 14) called Confidence: How Winning Streaks and Losing Streaks Begin and End, written by HBS professor Rosabeth Moss Kantor. While that original blog post is pretty specific to something that was going on at that point in time in my prior company, the thinking in the book about momentum and the role it plays in our psychology, about sports, about business, and about life in general, is timeless. Watching this team of teens go through ups and downs within an hour was…

Lessons from the Pandemic: a Mid-Mortem

It feels like it may be a bit premature to write a post with this title here in the summer of 2021. Even as vaccines are rolling out fairly quickly, the combination of the Delta mutation of the COVID-19 virus and a bizarrely large anti-vaccine movement in the US, plus slower vaccine roll-outs in other parts of the world, are causing yet another spike in infections.  However, I read Michael Lewis’s The Premonition last week, a bit of a “mid-mortem” on the Pandemic, and it got me thinking about what lessons we as a society have learned in these past 18 months, and how they can be applied to entrepreneurs and startups. I am particularly drawing on the few weeks…

Should CEOs wade into Politics?

This question has been on my mind for years. In the wake of Georgia passing its new voting regulations, a many of America’s large company CEOs are taking some kind of vocal stance (Coca Cola) or even action (Major League Baseball) on the matter. Senate Majority Leader Mitch McConnell told CEOs to “stay the hell out of politics” and proceeded to walk that comment back a little bit the following day. The debate isn’t new, but it’s getting uglier, like so much of public discourse in America. Former American Express CEO Harvey Golub wrote an op-ed earlier this week in The Wall Street Journal entitled Politics is Risky Business for CEOs (behind a paywall), the subhead of which sums up…

How to Select a CEO Mentor or CEO Coach

(This is the second in a series of three posts on this topic.) In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them. Selecting a CEO Mentor is…

The Difference Between a CEO Coach and a CEO Mentor and Why Every CEO Needs Both

(This is the first in a series of three posts on this topic.) Harry Potter was lucky.  He had, in Albus Dumbledore, the ultimate wise elder, in his corner.  Someone who could teach him how to be a better human being (er, wizard), how to be more proficient with his wand and spells, how to think strategically and defeat the bad guys. All of us would benefit from having an Albus Dumbledore in our lives.  But most of us don’t — and most of the people we’d call on to be that wise elder in our corner aren’t capable of the full range of advice and counsel that Dumbledore is.  Why work with a Coach or a Mentor?  I’ll start…

The Tension That Will Come With the Future of Work

The Tension That Will Come With the Future of Work A lot has been written about the Work From Anywhere life that knowledge workers are leading right now due to the pandemic, and what will come next.  Fred has a great post on it, and I’m curious to see how his and Joanne’s “Home Office Away From Home” space called FrameWork does when it opens.  In that post, he references a few other posts and articles worth reading: Imagine Your Flexible Office Work Future – Anne Helen Petersen We’re Never Going Back – Packy McCormick The Future of Offices When Workers Have Choice – Dror Poleg Instead of entering the debate about what the future will look like, which no…

Second Verse, Same as the First…Except Way Better

Almost a year into my second journey as a startup CEO at Bolster, and I’m getting more and more questions from other CEOs about what it’s like doing a second startup after almost 20 years at the first one…and achieving pretty good scale by the end.  The short answer is, it’s the same, only it’s way better.  Here’s why. I’m more confident.  So is our whole founding team.  When Jack and I started Return Path, we were 29.  This time, we were 49 — and the average age of the founders was probably 46 or 47.  The bottom line is that we don’t know everything about the business we’re building, but we know what we’re doing in terms of building…

Introducing the Bolster Board Benchmarking Survey

Over the years,  I’ve had a list of nagging questions every time I’ve contemplated my board, but didn’t have anyone I could turn to who had deep, broad advice on this topic. Those questions were: How big should my board be at this stage?   How many independent directors should I have?  What is the right profile of an independent director?  How many options should I give a board member?  How do I find the best, diverse, talent for my board openings? That’s why Bolster is excited to announce the launch of our first CEO tool: Board Benchmarking. This application (which is free!) is the first of a series of tools that we’re designing to help CEOs understand the performance, design,…

Grit

I was honored this week to be in a small group “fireside chat” with Angela Duckworth, author of the book Grit: The Power of Passion and Perseverance, and to meet her and ask a question. I want to hit on one theme here from the book and dialog, but I’ll start by sharing a 2×2 matrix (remember, I’m an ex-consultant, I think in frameworks) that we’ve used at home with our kids periodically. For the most part, we use it to talk to them about why they should work harder on math homework, but it’s had other use cases as well. Hopefully it makes sense on the face of it… …but essentially the framework teaches that if you are talented…

What Job is Your Customer Hiring You to Do?

My friend George, one of our co-founders at Return Path (according to him, the best looking of the three), has a wonderful and simple framing question for thinking about product strategy:  what job is your customer hiring you to do?  No matter what I’m working on, I am finding George’s wisdom as relevant as ever, maybe even more so since I am still learning the new context. Why is this a useful question to ask?  It seems really simple – maybe even too simple to drive strategy, doesn’t it? It’s very easy in technology and content businesses (maybe other spaces too) to get caught up in a landslide of features and topics. In a dynamic world of competition and feature…