Some executives make it a practice to meet regularly with employees that work under their direct reports (DRs). The reasons for such meetings can be many: To connect with the front-line employees and to get a sense of the world they live in; to check on the leadership of their DRs; to groom high-potential employees for advancing their careers; and, to get a first-hand view of the impact of their own leadership a few levels down on the working-level employees.

 

Even though such skip-level encounters are planned and done as a common practice with some executives, skip-level employees must take them seriously to both protect their reputation and to use these encounters to win some brownie points with the company’s executives to improve their career standing. Such encounters are not just limited to the first-level skip in an organization. Sometimes, a CEO may decide to catch-up with someone in their organization several levels down just to get the pulse of their organization. 

 

Since I often get requests from my clients for tips on how to prepare for such meetings and how best to leverage such opportunities for building the right “rapport” with your skip-level boss (and with those above them), I decided to write this blog in the form of Dos and Don’ts suggestions:

 

1. Casually just saunter—even when scheduled—into the executive’s office and start chatting about your life in general or start complaining about your problems—personal or work-related.

2. If you do decide to bring some querulous topic in your discussion make sure that you are not just bringing up something highly transactional (“yesterday the mail server was down and I had to stay late just to catch up with my emails.”), but has some import organization-wide and long-term. Don’t just complain about the problem, but go with a few suggestions to deal with the problem.

3. Assume that this is a forum for a bitch session and start telling them about how screwed up everything is around you and how difficult it is for you to get anything done.

4. Bad mouth your own boss by getting specifics about their habits or management style that you find annoying (“Sally always expects my work to be accurate and on time and I cannot always please her with that.”) because of your own shortcomings.

5. Gossip about your colleagues and go into the details about how your work suffers because of something they do that does not quite suit you.

6. Bad mouth your company by bringing up other companies—especially your competitors—and make invidious comparisons (“Now even Yahoo! is providing free meals to its employees. Why can’t we do the same?”)

7. Don’t discuss issues of policy that originate from the highest levels of the company. One of my clients (an FP&A specialist) complained to her skip-level VP boss that the billions of dollars of investment in China the company had announced over the next several years would be a waste of money.

8. Discuss any politics (inside or outside) by injecting your point of view in it. Stay completely out of this area. Same recommendations apply to anything religious (“Why can’t we get a day off for Divali?”)

9. Just start rattling off from a list of items you have compiled for this meeting; engage in a meaningful discussion with the executive, instead.

10.Go around telling your colleagues how you bad-mouthed your boss in this skip-level meeting and how you plan to continue to do this in your future such encounters until your boss straightens out.

 

 

1. Plan your meeting by preparing with specific topics that will help both the executive and you as a result of that meeting. E.g., “The recent change in the timeline for submitting the monthly and quarterly financials has helped us better prepare with our stories. We can do even better if we institute a common template for all the incoming data from 12 sources. I can create that template and show you how it will further streamline our process for you to get a more coherent story.”

2. Ask your peers about their experience with the skip-level meeting they’ve had and what works and what does not. Do not just go in blind and find out on your own.

3. Inform your direct boss that you are getting ready to meet their boss at the request they made and you plan to discuss with your boss the topics that you have decided to pull-together.

4. Cull down your original list of topics for discussion after meeting with your boss and develop a mental script of how you are going to use your time to discuss what you have planned. Even though this meeting is between you and your skip-level (or higher) boss, pretend that your boss is present in that meeting, listening to what is being said.

5. As you enter the executive’s office first thank them for asking you to meet with them and for their time. Even though you may have been given a certain time slot for this meeting ask again before settling down how much time they now have for this meeting.

6. Tell them that you have listed down topics in order of your priorities and would like to go through them one-by-one. After presenting your first item assess the response you are getting. If they are taking notes as you talk this is a good sign. If, on the other hand, they seem impatient, anxious to get to the next topic, and are evasive skip to the next topic.

7. Engage in a dialog and see how they are taking in your suggestions and inputs. Watch their body language carefully to manage how you steer your discussion. Be willing to pivot around a topic that seems to strike an unfavorable cord.

8. Stay upbeat and positive throughout.

9. Bring up positive aspects of your boss’ leadership that is helping you and your workgroup (remember #4 above!).

10.Do send an email with the summary of your discussion, thank the uber boss, and send a copy of that email to your boss.

Encounters with higher-level executives in your company must be seen as your opportunity to make an impression and to establish a positive relationship—and trust—with the company’s higher ups. Use these guidelines to get the most out of such meetings, both for yourself and for your organization.

Good luck!