These one on ones are called skip-level meetings and depending on the company, can be a common occurrence. They also have the potential to cause a huge mess and upset everyone, from those direct reports to the executives who are supposed to be leading them. First, to lay out a case for why skip-level meetings could be valuable:
1. The CEO wants information directly from the front lines
The CEO is ultimately responsible for the health and success of the business. That means s/he needs real information that is unfiltered to make the best decisions. Good CEOs know that even well meaning executives can filter information to look good in front of the boss. The best source of information may be someone else’s direct reports.
If the teams are doing weekly written recaps (using something like Weekly Update), the CEO could potentially be CCed or just login to the admin portal to glance through each team’s top objectives, concerns, etc. This is non-intrusive and allows the CEO to quickly get a pulse on what is going on in the front lines.
2. It is most efficient to avoid a middleman
Sometimes it is just inefficient to go to the VP Marketing when the matter is precisely related to product marketing, thus the Director of Product Marketing is going to have a much better answer.
3. The CEO needs a quick answer
Often the CEO is working on something (say an investor deck) and just needs some quick information. Chatting with the Business Ops Manager who can quickly pull a report from Salesforce sounds much easier than waiting for the busy VP Operations to delegate that task to the very same Business Ops Manager.
To avoid making a mess while doing these one on ones, and if a CEO feels there there is a need to do them, consider:
1. Make them ad-hoc, not regularly scheduled
It would definitely be out of place for the CEO to have a regularly scheduled one on one meeting with another executive’s direct report. If the CEO is interacting with that team member, it should be more ad-hoc as needed.
2. Give their manager a heads up
If the CEO does interact with someone else’s direct report, it is good form to give that executive a heads up. It can be as simple as “Hey John, I had a quick discussion with Anna this afternoon. We talked about X, Y, Z.”
3. Be careful what is discussed to avoid undermining
One way to quickly make a mess is by sending mixed messages that confuse the directive that someone may have gotten from their direct manager. In skip-level meetings, the CEO should be doing less talking and more listening.
4. Do not assign tasks
Never assign tasks to someone else’s direct report. As the CEO, you have no idea what is on their plate or what their manager has on the roadmap for tomorrow. By throwing a task at them, it creates conflict across the board because the employee places a premium priority on a task coming from the CEO, and now may not deliver against the measurable goals that his manager had already set.