Meeting Skip-Level Boss!

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 companys 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 Donts suggestions:

Dont
1.Casually just sauntereven when scheduledinto the executives office and start chatting about your life in general or start complaining about your problemspersonal 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. Dont 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 companiesespecially your competitorsand make invidious comparisons (Now even Yahoo! is providing free meals to its employees. Why cant we do the same?)
7.Dont 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 cant 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.
Do
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 theyve 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 executives 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 relationshipand trustwith the companys higher ups. Use these guidelines to get the most out of such meetings, both for yourself and for your organization.
Good luck!

About Author

Dilip has distinguished himself as LinkedIn’s #1 career coach from among a global pool of over 1,000 peers ever since LinkedIn started ranking them professionally (LinkedIn selected 23 categories of professionals for this ranking and published this ranking from 2006 until 2012). Having worked with over 6,000 clients from all walks of professions and having worked with nearly the entire spectrum of age groups—from high-school graduates about to enter college to those in their 70s, not knowing what to do with their retirement—Dilip has developed a unique approach to bringing meaning to their professional and personal lives. Dilip’s professional success lies in his ability to codify what he has learned in his own varied life (he has changed careers four times and is currently in his fifth) and from those of his clients, and to apply the essence of that learning to each coaching situation. After getting his B.Tech. (Honors) from IIT-Bombay and Master’s in electrical engineering(MSEE) from Stanford University, Dilip worked at various organizations, starting as an individual contributor and then progressing to head an engineering organization of a division of a high-tech company, with $2B in sales, in California’s Silicon Valley. His current interest in coaching resulted from his career experiences spanning nearly four decades, at four very diverse organizations–and industries, including a major conglomerate in India, and from what it takes to re-invent oneself time and again, especially after a lay-off and with constraints that are beyond your control. During the 45-plus years since his graduation, Dilip has reinvented himself time and again to explore new career horizons. When he left the corporate world, as head of engineering of a technology company, he started his own technology consulting business, helping high-tech and biotech companies streamline their product development processes. Dilip’s third career was working as a marketing consultant helping Fortune-500 companies dramatically improve their sales, based on a novel concept. It is during this work that Dilip realized that the greatest challenge most corporations face is available leadership resources and effectiveness; too many followers looking up to rudderless leadership. Dilip then decided to work with corporations helping them understand the leadership process and how to increase leadership effectiveness at every level. Soon afterwards, when the job-market tanked in Silicon Valley in 2001, Dilip changed his career track yet again and decided to work initially with many high-tech refugees, who wanted expert guidance in their reinvention and reemployment. Quickly, Dilip expanded his practice to help professionals from all walks of life. Now in his fifth career, Dilip works with professionals in the Silicon Valley and around the world helping with reinvention to get their dream jobs or vocations. As a career counselor and life coach, Dilip’s focus has been career transitions for professionals at all levels and engaging them in a purposeful pursuit. Working with them, he has developed many groundbreaking approaches to career transition that are now published in five books, his weekly blogs, and hundreds of articles. He has worked with those looking for a change in their careers–re-invention–and jobs at levels ranging from CEOs to hospital orderlies. He has developed numerous seminars and workshops to complement his individual coaching for helping others with making career and life transitions. Dilip’s central theme in his practice is to help clients discover their latent genius and then build a value proposition around it to articulate a strong verbal brand. Throughout this journey, Dilip has come up with many groundbreaking practices such as an Inductive Résumé and the Genius Extraction Tool. Dilip owns two patents, has two publications in the Harvard Business Review and has led a CEO roundtable for Chief Executive on Customer Loyalty. Both Amazon and B&N list numerous reviews on his five books. Dilip is also listed in Who’s Who, has appeared several times on CNN Headline News/Comcast Local Edition, as well as in the San Francisco Chronicle in its career columns. Dilip is a contributing writer to several publications. Dilip is a sought-after speaker at public and private forums on jobs, careers, leadership challenges, and how to be an effective leader.

Disclaimer: Please use this channel at your own discretion. These articles are contributed by our users. We are not responsible or liable for any problems related to the utilization of information of these articles.