“If you can’t measure it, you can’t manage it” goes an adage that is often recited as if it were some kind of profound truth (misattributed to Deming). And of course there is some logic here. Let’s say you own a website and you want to grow it. Measuring traffic to the site will help you figure out whether you are succeeding with that. But even this seemingly trivial example helps us understand a crucial point which could be summarized as “You manage to what you measure.” Suppose that page vi...

And now for something different: just some pragmatic advice. You should run all hands meetings in your company. They are a key bonding and communication opportunity. You can have them until you are quite large – for instance, Twilio, which as gone public, still does them. Here is the key though: make sure to solicit questions and topics ahead of time. You should even make it possible for employees to do so anonymously. For some people that seems obvious but I have seen quite a few situations ...

Six years ago I wrote three tips on making your board effective (tip #1, tip #2 and tip #3). Since then there is a lesson that I keep on relearning and so I am writing this tip #4 as much as a reminder to myself as anything: your board cannot be effective if it only talks to you, the CEO. Instead, you should make sure that members of your board also have relationships with execs on your senior team. Now I have a feeling that quite a few VCs/board members and also CEOs will disagree with this....

Yesterday, Twitter laid off about 8 percent of its employees or roughly 1 in 12 people. Most entrepreneurs dread a moment like that more than anything else. It takes the pain of firing an individual employee and massively amplifies it. And yet it is often unavoidable on the path to building a company and sustaining it for the long term. Some of the criticism of Twitter’s layoffs took the form of arguing that Twitter shouldn’t have hired those employees in the first place. That criticism amoun...

The first week on my first job after college I came into work super early and left super late. At the end of the week my then boss called me into his office and said: “it’s great that you are so enthusiastic about this job, but you are setting a high bar for everyone’s expectation of you — what will they think when you come in a bit later next week?” I have never forgotten that because it embodies a critical lesson: what others expect of us is in no small part determined by our own behavior (...

Today one of our portfolio companies is holding their internal management training in our offices. They have asked me to talk a little bit about my own experience with the challenge of going from being an individual contributor to being a manager. I remember this being a very rough transition for me and it took me quite a long time to get comfortable as a manager. I went from individual contributor to founder and didn’t have the benefit of management training! Looking back the biggest insight...

Yesterday we had our portfolio company summit with the CEOs of most of our active investments in our office. It is always a really fun day because there are great discussions about a far ranging set of topics from hiring to business models. This year as an opener we went around the room and everyone talked briefly about a lesson learned in the last 12 months. There were a ton of really good insights there and some really funny ones, such as “it is better to have a hole than an asshole” (about...

I have written about the topic of prioritization before, but maybe with a title that was too oblique – “Applying Engineering Business: Binding Constraints.” There I made the point that at any one time a startup tends to have only one binding constraint. It’s the problem the startup needs to solve to get to the next level. That could be the next financing, or hiring people or finishing a key project. But what about more fine grained prioritization? What about the long list in front of the prod...

I have had the privilege of observing a number of founders grow their companies from just a few people to over a hundred employees. Leaving all the other growth challenges aside, I have come to conclude that personal scaling is the most important issue. By personal scaling I mean figuring out how to go from mostly doing to mostly managing. There are many aspects to this transition but the central one would seem to be trust. A map at 1:1 scale isn’t useful. And as I discovered yesterday during...

A quality that I find hugely important but increasingly rare in people is the willingness to admit mistakes. Growing up I wasn’t really part of a culture in which mistakes are openly discussed and used as an opportunity to learn. For a long time, my own approach was therefore one of just moving on or trying to fix things without admitting to any mistakes (often compounding the initial mistake in the process). But as I started to manage people I came to realize that if you want them to try thi...