Category

Business

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…

OnlyOnce, Part XX

I realize I haven’t posted much lately.  As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004.  That inspired me to create a blog for entrepreneurs and leaders.  I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO:  A Field Guide to Scaling Up Your Business back in 2013. Today is a special day in…

Sometimes a Good Loss is Better than a Bad Win

I just said this to a fellow little league coach, and it’s certainly true for baseball.  I’ve coached games with sloppy and/or blowout wins in the past.  You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game.  And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run.  You are sad about the L, but at least you left it all out on the field. Is that statement true in business? What’s an example of a “bad” win?  Let’s say you close a piece of business with a new…

Response to the Journal

(This post is running concurrently on the Return Path blog.) It is now widely understood that the Internet runs on data. I first blogged about this in 2004—14 years ago!— here.  People have come to expect a robust—and free!—online experience. Whether it’s a shopping app or a social media platform like Instagram, these free experiences provide a valuable service. And like most businesses, the companies that provide these experiences need to make money somehow. Consumers are coming to understand and appreciate that the real cost of a “free” internet lies in advertising and data collection. Today, the Wall Street Journal ran an article exploring the data privacy practices of Google and some of the third party developers who utilize their G Suite ecosystem….

Feedback Overload and Confusion – a Guide for Commenting on Employee Surveys

We run a massive employee survey every year or so called The Loop, which is powered by Culture Amp.  We are big fans of Culture Amp, as they provide not only a great survey tool but benchmarks of relevant peer companies so our results can be placed in external context as well as internal context. The survey is anonymous and only really rolled up to large employee groups (big teams, departments, offices, etc.), and we take the results very seriously.  Every year we run it, we create an Organization Development Plan out of the results that steers a lot of the work of our Leadership team and People team for the coming year. I just read every single comment that…