The Grassy Road

Why I put together a retreat for public company board chairs on how to find a new CEO

I was intimately involved in three CEO searches in 2024. I wish I had known at the beginning of the year what I know now. I serve on the boards of three public companies and one private company. I chair the board of two; three of my companies, for different reasons, required a CEO search last year. The theory of CEO succession is fairly simple: it’s planned, it’s smooth, it’s an ongoing discussion, it takes about 6-9 months–but that is textbook, not reality. In theory you are having discussions with [...]

By Penny Herscher|2025-11-02T08:51:11-08:00September 4, 2025|Boards, Leadership|Comments Off

Are you coin operated?

What does it look like when someone is coin operated? This is the person who, any time compensation comes into play, deeply cares how much money they will make. Their focus on their earnings outweighs any other circumstance: what is best for the company, what is best for their own future, how the situation impacts their peers – and they are often oblivious to how it makes their peers see them. And how they view the people around them comes into play too. Yes, sometimes I joke that sales people [...]

By Penny Herscher|2025-03-31T11:11:26-07:00March 27, 2025|Career Advice|Comments Off

The challenge of FOMO in your career

FOMO today is typically about missing out on something cool – someone’s vacation on Instagram, a restaurant they ate at, their new car. Merriam-Webster defines it as “fear of missing out : fear of not being included in something (such as an interesting or enjoyable activity) that others are experiencing”. But in the rat race of our modern careers FOMO happens around your choice of profession too. I see this many times when coaching people at transition points in their careers. You’re working at a large company (in a good [...]

By Penny Herscher|2025-01-24T08:49:08-08:00January 23, 2025|Career Advice|Comments Off

Why Goldman Sachs’ behavior in Bully Market by Jamie Fiore Higgins is just not that unusual

I have just finished reading Bully Market – the story of how Jamie Fiore Higgins rose to MD at Goldman Sachs while hating the culture but loving the money. It’s a fast fun read, not great literature but a compelling insight into the behaviors women have put up with in the last 30 years that are all too common, and yet still egregious enough to be shocking. She’s brave to write so frankly about what she experienced – hats off to her. You can read the NY Times review here. The [...]

By Penny Herscher|2022-11-08T13:29:58-08:00November 7, 2022|Career Advice|Comments Off

Visiting the Luiss Business School in Rome

I was fortunate enough to be asked to speak at the Luiss Business School in October - in Rome no less! The discussion centered on tech, subjects like AI, China, Semiconductors and then the role and importance of diversity. And all within a gorgeous 16th century papal palace. Professor Pierluigi Matera graciously interviewed me in two settings: One on one and then with a group of students. Here are the two videos. My comments on diversity start at ~35:00 in the first one, and thread through the second one. https://www.youtube.com/watch?v=MIpKJWhWDBA [...]

By Penny Herscher|2021-11-05T14:51:11-07:00November 5, 2021|Career Advice|Comments Off

The choice we make to be loyal, or not

Is loyalty a good thing – or is it a dirty word? Depends on the context – politics, business, your family? But when talking about professional loyalty it can be a double-edged sword. Fundamentally to be loyal to another person is a choice you make. You may have several different reasons to choose to be loyal. You may admire the person – their intellect, their effectiveness, their values. You may be grateful to them for helping you through a tough situation. Maybe they made you money, or promoted you and [...]

By Penny Herscher|2021-09-15T05:56:09-07:00September 14, 2021|Career Advice|Comments Off

The unexpected lessons I learned from my cardiac arrest

In the early morning of Nov 7, 2020, walking alone on a beach in Maui, my heart stopped. It didn’t beat for about 4 minutes before I had the incredible luck of being found by a doctor who did CPR and saved my life. Obviously, a lot more drama happened after that, including being put into a therapeutic hypothermia coma for a couple of days and a long stay in hospital with a beautiful view of the West Maui mountains but the definitive moment of luck/grace/lightning was being found by someone who [...]

By Penny Herscher|2021-02-09T10:30:58-08:00January 30, 2021|My Personal Journey|Comments Off

The critical difference between Governance and Management when you are on a board

This question comes up a lot when teaching wannabe directors. And it comes up with employees who are under the mistaken belief that their board actually manages the company. So let me demystify it now. We don't manage. At all. The critical difference is that the board is in place to provide oversight, not to make decisions. Oversight to ensure shareholders are well served. Oversight to ensure the law is followed. That, over time, the decisions the leadership team makes are good ones. Oversight to ensure the company is not [...]

By Penny Herscher|2021-01-28T10:05:38-08:00January 27, 2021|Boards|Comments Off

Men to avoid: the ones who tell you to slow down

There is nothing more demotivating than someone above you in your chain of command telling you to slow down, to be less ambitious. Especially if you are a woman and the teller is a man. This behavior is, of course, not new. So many of our mansplaining experiences are captured in the new book Men to Avoid in Art and Life by Nicole Tersigni - I'm using one of her captioned paintings here to illustrate my message. A laugh-out-loud joy of a book and Twitter meme. I was coaching a [...]

By Penny Herscher|2021-01-28T10:02:30-08:00January 19, 2021|Career Advice|Comments Off

The velvet-lined rut

I’ll start with a disclaimer. I am a privileged Silicon Valley executive with no grounded reason to complain. I have my home, my family (our adult kids came home) and a living that creates a comfortable lifestyle. So don't feel sorry for me. But here I am, in the middle of a global pandemic, back in lockdown in a state where the infection numbers are going in the wrong direction, turning sixty today. Wow - that's a big number. I'm not afraid of it, but as I look back on the [...]

By Penny Herscher|2020-07-16T15:29:21-07:00July 16, 2020|My Personal Journey|Comments Off