My Biggest Worry Most Days

There were a lot of concerns I faced as CEO. Some problems we had to resolve, some ongoing issues that would raise up at various times. Life at a startup has an unending stream of challenges.

But there was one concern, one worry, that was front of mind most days. Easily my biggest issue. And it was not making our sales numbers. Nor was it hiring. Those were constantly there but a distant second.

My #1 worry was the employees. Were they happy at Windward, were they motivated, and were they focused on our priorities. Those three questions are tightly interrelated and if the answer is no to any of them - we're fucked. On the flip side, if it's a strong yes to all of them then we're in good shape and we're unlikely to have anyone leave.

First comes happy. We did a number of things here. We surveyed constantly, especially on the Gallup Q-12 questions. In the monthly 1:1s we asked "What change could Windward make so that you would never leave" - which was an inviting way to ask people what they were unhappy with. We went to great lengths to explain again and again (7 times x 7 ways) what our goals were and why. The why being the more critical part. We used OKRs (7 Geese - highly recommended), but by team not individual (things changed too fast for individual).

Second comes working on the right things. In our case we stressed that we were loosely coupled/tightly aligned. And further stressed that key to this working is that it was a key responsibility of everyone to understand where we are going and that once the decision was made, do their best to achieve it. And point out that the big danger of this approach is it gave people room to go in their own direction - and why that was so harmful. And again, in the monthly 1:1s there was the question "Is there anything in our goals that you do not understand.

Keep in mind, this did not mean everyone agreed with the goals. What it meant is they say that their thoughts were heard and considered. And we then based on the discussions decided what to do. In other words, argue on the way in, salute on the way out.

Third were they motivated? If you have the above two handled well, then people who want to accomplish great things will be very motivated. And people who would rather sit on their ass, and in the above case will often be less happy because there is no excuse for mediocre performance, will not get much done. And those people you need to fire. A high energy super productive company is not for everyone. And you're unlikely to change something so fundamental in a person.

And how did we do at Windward? All of this was learn as we went. We got better at it over time. Towards the last couple of years I think we got pretty good at it. But even at our best there was still room for significant improvement. But the key thing is, we kept getting better at it.