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. On a number of occasions I have heard this approach characterized as “going around the CEO” or as “undermining the CEO.” Let me be super clear here: if a CEO can be undermined simply by talking directly to someone on his or her senior team, then there is already a massive problem. In fact, I am now using this as an indicator the other way round. I try to stay away from backing founders who are not comfortable with me talking to some or all of the members of their senior team directly.

Why do I feel so strongly about this? Because you cannot help in a situation where you don’t know enough. Almost all the mistakes that I have made as a board member can be traced back to not having enough information about a critical issue. Just like doctors are likely to make the wrong diagnosis if presented with none or only some but not all symptoms, so board members cannot help guide to the right decision if they are somewhat or completely in the dark about what is actually going on in the company.

But how can you be in the dark if you are being presented with lots of information even by team members directly in board meetings? Because it is super hard for people to say things in a board meeting that aren even remotely controversial inside the executive team. These could be disagreements among senior team members about strategy, or implementation specifics or even about the performance of the CEO. Information on these difficult topics only really comes out in one on one conversations with senior team members.

Now of course there is a way to do this wrong as a board member. You could in such a one-on-one meeting say things that would effectively undermine the CEO. This is no different than in any other “skip level” meeting, e.g. the CEO meeting with someone lower down in the organization. In such meetings one has to be a listener first and foremost and if asked for a comment one has to acknowledge what one has heard but abstain from making a judgment.

I will write a follow up post to this that talks more about how I have come to understand the ultimate role of a great board member: helping a founder understand his or her weaknesses and how those are reflected in the organization. There is little chance of that happening without getting feedback directly from senior team members.