Dear Founder

Dear Founder,

If you opened this letter you’re probably looking for ways to avoid nasty surprises. I always say that problems don’t get better with age. Therefore, I’m always on the lookout for potential issues and conflicts in the hope that we can surface them early—and fix them fast.

I wrote this letter to share the benefits of being proactive rather than reactive. Let me give you a real-life example of what I’m talking about. One time, at Yahoo! we had a long-scheduled board meeting. Unfortunately, it had never been communicated to several new board members. I had repeatedly asked about it, but the company wasn’t sure it still wanted to have a meeting. Ultimately, it was necessary to hold the meeting in order to file our proxy by a certain time. While there was no choice about having the meeting, that didn’t mean that it would be easy to ensure that all board members could attend. So, the scramble began to try and get the board together. Of course, by this time four of the thirteen members couldn’t attend due to conflicts. I proactively reached out to all four, apologized for the churn (which is almost always avoidable and was in this case), explained why the meeting had to happen, and let them know I would be happy to represent them and their point of view in the meeting. One of the four hadn’t heard anything about the meeting and was very suspicious, which then required my taking time to carefully explain everything to alleviate the concerns. Personally contacting them was pivotal. If we had conducted the meeting without proactively reaching out first, I’m certain there would have been much more fear and that it would have ignited trust issues.

Allow me to share another recent example of solving an issue before it became a problem: One of my WIN Labs founders was sending me weekly status updates (I did not force him to do this, but I appreciate that he does it). I had been away on vacation and I didn’t get one. The next week I didn’t receive one, either. I proactively asked him where his status was and he said, “I sent it to you.” I was with him, so we went to my email to check and I confirmed I definitely hadn’t received it. We discovered that he was sending the updates to a WIN alias that I wasn’t on. Had I not checked up, he would have continued sending these weekly reports assuming I was getting them and probably wondering why I hadn’t commented on any of his communications. And I would have continued to miss all the great information he was sharing in his weekly statuses. While this would not have been the end of the world, if left unchecked, it could have led to a schism between investor and founder. Instead, we solved it when it was simply a miscommunication.

In other letters, I’ve talked about productivity and forcing functions. Productivity is all about getting way more done than the average person—and we all know nasty surprises often derail you from great productivity. Forcing functions (including 1:1s and status reviews) help surface problems early and provide you with an opportunity to immediately address any issues that arise, making them useful tools to help increase productivity.

Yet it’s not enough to assign tasks and integrate forcing functions. There are soft skills that matter here, too. I make a habit of spending time focused on getting to know most of the key people on every project. This includes checking in with them frequently and observing body language to get a deeper sense of what else may be happening. It also includes observing the chemistry of the team. I learned the value of observation while I was at eBay and sat in a cubicle. Initially I hated sitting in a cube! I had been in an office for years and had often retreated to my office to hide when things got tough. Now, everything was out in the open. When there was tension, it was palpable. And that made it easier to intuit what was going on. With that, something amazing happened—issues were resolved much faster because we didn’t want to live with these problems anymore.

Some thoughts on how to solve problems early, or even prevent them from happening:

• Be respectful of each other’s time. Communicate early what you need and by when. Obtain a commitment to have people get back to you when needed. If you’re always in crisis mode and changing meetings and times, you are causing massive churn for others on your team. This, in turn, can lead to massive churn for their teams.

• Teach your team that identifying problems should be encouraged and that early warnings are also appreciated. It’s much harder to solve problems when you are out of time to do so. Of course, you need to also teach your team how to come up with solutions on its own as well.

• Check in frequently on the things you care the most about. Have formal check-ins and frequent 1:1s, as well as informal and impromptu check-ins.

• Pay attention to all the signals that exist. I’ve often had to probe deeply with somebody whose behavior, attitude, or patterns have changed, and in doing so I’ve discovered early signs of a problem. Look out for changes in cadence around communication and listen to what other people are saying. As they say, where there’s smoke, there’s fire.

• Always do the postmortem. When you end up with a problem that could have been solved earlier, take the time to debrief the team on how to do better next time. Set expectations on what’s expected when similar situations arise.

I promise you that if you inculcate the practice of surfacing problems early and fixing them fast, your job as CEO will become far easier AND more fun!

All the best,

Maynard

P.S. If you are receiving this too late and you already have a nasty problem, see the “When you have a crisis” letter in the next chapter!