Leadership Archives - 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

Stop focusing on your startup valuation!

It never ceases to amaze me how hung up entrepreneurs get on the valuation of their startup as they raise money. It came up in a coaching session again yesterday. In the abstract yes, valuation matters. It tells you how much of your company you are going to sell in order to raise money. It sets a baseline for you which you will (hopefully) exceed on your next raise. It's a validation that your work has value. But it is NOT a measure of pride, or ego, or size. Your [...]

By Penny Herscher|2020-06-17T11:18:17-07:00June 17, 2020|Leadership|Comments Off

What impression are you leaving once you leave?

It can be a strain to be aware of your actions 24/7 but as a leader it is critical. You leave an impression every time you interact with anyone, and if you are a busy person you may be leaving the impression in a few seconds. Think about when you enter a meeting room, realize you are in the wrong room and leave. What did you say? Did you come across as simply having read the wrong room on your calendar, or as a disorganized ditz. How about when you [...]

By Penny Herscher|2019-01-04T09:56:57-08:00January 3, 2019|Leadership|Comments Off

Don’t argue in front of your customer!

We've all been there. You're in a meeting with a prospect or customer and someone on your team says the wrong thing. You're infuriated and your knee jerk reaction is to correct your teammate in front of the customer. Or get angry with your teammate. Not a good idea. This can happen when you take a junior engineer into a meeting and she feels she has to tell the customer everything that's wrong with the product. Or a senior executive who commits you to a schedule you know you can't [...]

By Penny Herscher|2019-01-04T09:57:25-08:00December 7, 2018|Leadership|Comments Off

Winning as a CEO takes courage – does your CEO have it?

It takes courage to be a great CEO and yet our world is populated with mediocre ones so how do you assess a company CEO before you chose to join his company, or whether you have the mettle to be one yourself? The evidence is there if you know where to look. It’s not just about a CEO who can give a rallying speech (although it’s fun to watch a CEO like Marc Benioff do it). It’s not just about a brilliant technical founder CEO who can talk product and [...]

By Penny Herscher|2019-01-04T10:02:33-08:00April 24, 2018|Leadership|Comments Off

It’s time for economic equality for women: WE2

Sometimes it’s just time. I am more deeply convinced now in 2018, than ever before, that the long-term path to a more sane, peaceful world is equality for women in society. The research is conclusive. Investing in girls and women transforms economies, and healthy, growing economies are more peaceful. But I am not a politician, I am not a Sociologist, I am a tech executive and so I need to practice what I know in order to do my part. Women, and men, need to invest in women. Invest in [...]

By Penny Herscher|2018-01-05T22:51:54-08:00January 4, 2018|Equality, Leadership|Comments Off

Five tough lessons on being a mentor

Coaching and mentoring is increasingly popular, everyone wants one, everyone has one. This is somewhat a result of the explosion in the number of startups over the last ten years, but also because the word is out that getting a good mentor can really help you grow faster at any stage of your career. And women want to help women! I have mentored on and off for the last 20 years but in the last 2 years since I stepped down as CEO I have focused almost entirely on women, [...]

By Penny Herscher|2019-01-04T10:07:19-08:00November 10, 2017|Leadership|0 Comments

5 reasons it’s critical to truly understand your P&L

In the last month I have had the experience of three small business leaders talking to me about their P&L in moment-in-time terms. Something like this... for this quarter (or this year) we'll make $X, we spend $Y less than I thought so we're $Z ahead. Usually followed by why $X and $Z are so great, and how they'll spend those extra dollars they are ahead, or why their company is successful as a result. Naive. Unless you have a steady business that has been the same for a while, [...]

By Penny Herscher|2019-01-04T10:12:19-08:00July 20, 2017|Leadership|0 Comments

The importance of being humble

Photo: At the Jordan river where Christ was baptized and Israeli and Jordanian soldiers watch each other, guns cocked We’ve all met this person in our professional lives. Smart but self-absorbed, in love with their own success so far, or with the self-importance of their title, or the size of their business, or how attractive they are. Executives who are so used to everyone catering to their every need that they forget to be courteous. VCs who are so used to entrepreneurs beating down their doors they forget to be kind (or [...]

By Penny Herscher|2017-12-07T10:33:34-08:00July 16, 2017|Leadership|1 Comment

When to tell your employees to take a hike

Small companies are like families. They are full of tension, tight relationships, dreams and disappointments and they form a culture all of their own. And when they are small how each and every employee behaves affects the culture of the company. What it is like to come to work every day, how people solve problems, how they interact and help each other, or don't. In every group of employees you hire you are bound to hire a few non performers, and it's management 101 that you know you have to [...]

By Penny Herscher|2020-01-09T11:23:39-08:00May 13, 2017|Leadership|0 Comments