Category

Leadership

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…

Startup Boards, the book, and also why they matter more than ever these days

My latest book (I’m a co-author along with Brad Feld and Mahendra Ramsinghani), Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, is now live on Amazon – today is publication day! The book is a major refresh of the first edition, now eight years old. I was quoted in it extensively but not an official author – Brad and Mahendra were nice enough to share that with me this time. The book includes a lot of new material and new voices, including a great Foreword by Jocelyn Mangan from Him for Her and Illumyn. It’s aligned with Startup CEO and Startup CXO in look and in format and is designed to be an easy-to-read…

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…

Signs Your CFO Isn’t Scaling

Post 4 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO, When it is Time to Hire Your First Chief Financial Officer, and What Does “Great” Look Like in a CFO?) While all the functions of a team are needed, perhaps the most critical function to make sure your company is able to scale is the CFO. Cash flow, investments into the business, compensation, budgets—nearly everything that happens in a company flows through the CFO—and it should. So, getting this role right is one of the most important tasks of any startup team. But how do you know if your CFO is up to the task of scaling? For CEOs, one…

What Does “Great” Look Like in a CFO?

Post 3 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO and When it is Time to Hire Your First Chief Financial Officer.)  A lot of startups have a bookkeeper, accountant, or even a spouse of a founder or employee handle the finances when they first start out, and that’s fine. But at some point you’ll want to hire a CFO and if you’re dealing with a lot of chaos it’s easy to think, “well, anybody is better than what we have now.” But I would hold off on that thinking because the CFO, a great one, will do a lot more than just manage the finances, AP, and AR. A…

How to Get Credit for Non-Salary Benefits: The Total Rewards Statement

A couple weeks ago, I blogged about some innovations we’d made in People practices around basic benefits. But that post raised questions for me like “Why do you spend money on things like that when all people care about is their salary? When they get poached by another company, all they think of it the headline number of their base compensation, unless they’re in sales and think about their OTE.” While that is hard to entirely argue against, one thing you can do as you layer in more and more benefits on top of base salary, you can, without too much trouble, produce annual “Total Rewards Statements” for everyone on your team. We did this at Return Path for several…

Book Short: Intentionality in Life

I haven’t done short book summaries in a LONG time, but I’ll try to start adding that back into the mix as I read interesting and relevant books. Here’s one to add to your list: One Life to Lead, by Russell Benaroya. I was recently connected to Russell by a mutual friend, TA McCann at Pioneer Square Labs. TA had a sense Russell and I would hit it off, and we did. Russell is a multi-time founder/CEO, a Coach, and an author, so we have a lot in common. One Life to Lead is an excellent book. First, it is short and easy to get through. Unlike a lot of business books, it doesn’t go on too long or contain…

Open Expense Policy

I wrote a post the other day about innovating employee benefits practices, and I realized I’d never documented a couple other ways in which we have always tried to innovate People practices. Here’s one of them: the Open Expense Policy, which I wrote about in the second edition of Startup CEO in a new chapter on Authentic Leadership when talking about the problem of the “Say-Do” gap.  Here’s what I wrote: I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a…

Top 3 Mistakes Later Stage Founders Make

Last week, I blogged a podcast riff I did about the biggest mistakes early stage founders make and what to do about them. Here’s a summary of part 2 of what I said about later stage founders. Misreading Product/Market Fit or a lack of Product/Market Fit. Misread it high, and founders end up dumping money into sales and marketing too soon. Misread it too low, and you can fire a good sales or marketing team when it’s not their fault! On the high side, Product/Market Fit isn’t just coming from a healthy CAC/LTV ratio or by good early adoption. Early adoption can come from a small group of Visionaries (here I’m channeling Geoffrey Moore’s Technology Adoption Lifecycle curve from Crossing…

Top 3 Mistakes Early Stage Founders Make

I just did a podcast recording the other day for someone who asked me the biggest mistakes founders make and what to do about them. I divided my response into “early stage” and “later stage” founders. Here’s a summary of what I said about early stage founders. They cling to a “good enough person” or someone who is a good performer but a weak cultural fit because they either feel beholden to that person for their output, or worse, they’re actually afraid of losing them because they’ll miss a milestone or maybe trigger some other departure. The “what to do” of course is to have courage and make the change! I wrote an essay years ago in Brad Feld and…