Category

Management

The Evolution of Feedback in Our Organizations

Across 22 years and two companies now, our system of giving performance feedback has evolved significantly. I thought I’d take a pass at chronicling it here and seeing if I had any learnings from looking at the evolution. Here’s how things evolved over the years: Written performance reviews. The first year of Return Path, we had a pretty standard process for reviews. They were more or less “one-way” (meaning managers wrote reviews for their direct reports), and they only happened annually. Written 360 reviews. We pretty quickly moved from one-way reviews to 360s. I wrote about this here, but we always felt that being able to give/receive feedback in all directions was critical to getting a full picture of your…

What Men’s Rooms Can Teach Us About Leadership and Management

I hope this post doesn’t gross anyone out or offend anyone. I admit it’s a little weird, and that it’s more accessible to men. Hopefully everyone can get my point, even if men get it a bit more. I’m channeling Brad as I write this. So bear with me. Here is a picture of a men’s room with floor mats under the urinals. The difference between using a men’s room that has floor mats and using a men’s room that does not have floor mats is profound in multiple ways. I’ll leave out the specifics, but you can imagine the comparative experiences if you haven’t had one or both. A really good floor mat, from a quick scan of Amazon…

Our Operating Philosophy – the Mostly Self Managed Organization (MSMO)

Last week, I wrote about the concept of the Operating Philosophy, and how it fits with a company’s Operating Framework and Operating System and defines the essence of who you are as a company…what form of company you are. While we had a loose Operating Philosophy at Return Path, we never really crisply articulated it, and that caused some hand-wringing at various points over the years, as different people interpreted our “People First” mantra in different ways. So this time around at Bolster, we’re trying to be more intentional about this up front. We have labeled our company a “Mostly Self Managed Organization” or MSMO (pronounced Miz-Moh). We made those up. Our Operating Philosophy – we are a Mostly Self-Managed…

The Concept of the Operating Philosophy

I’ve always been a big believer in the Operating Framework and the Operating System as two of the management underpinnings behind every well run company. The Operating Framework is the company’s Mission, Vision, Values, Strategic Objectives, and Key Metrics. Companies have all sorts of different labels for this, from Balanced Scorecard to Salesforce’s V2MOM to Patrick Lencioni’s 6 Questions. It’s what you have to define up front, refresh annually, and tweak quarterly so that people in the company are aligned and know where you’re going. The Operating System, as I wrote extensively about in Startup CEO, is the collection of practices, meetings, mailing lists, routines/rhythms, and behaviors that your company and team use and depend on to run the business…

Giving Away Credit – Added Rationale

I just finished up a coaching call with a late-stage CEO client, and we were talking about a situation where he helped tee up a couple successes for a new senior executive on his team and then promptly gave the exec credit for the successes. That’s good form as a leader – you take the blame when things go wrong but give away credit when things go well. But my client articulated a selfish reason to this that goes beyond the “good leadership form” argument that I’d never thought of before: “When you give them the credit, you win twice.” What he meant by that is that you get your first win when you bolster the person on your team…

Second Lap Around the Track

I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap. Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is…

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…

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…