Bob Goldman
Need a career boost? Schedule a “skip-level meeting.”
That’s a meeting that skips the person who directly manages your job and your paycheck to schmooze with some dingbat two steps higher on the org chart, who doesn’t know you exist.
The concept of a skip-level meeting was news to me — news I received from Melody Wilding, author of “How to Have a Successful Skip-Level Meeting with Your Boss’s Boss,” a recent post on the Forbes website.
If you’re a person who starts sweating when their boss’s name appears in your inbox, or worse, when their body appears in your doorway, you may balk at scheduling a meeting with your scary boss’s even scarier boss.
If your manager is confident enough to not feel threatened by the thought of you whispering sweet nothings in their manager’s ear, executive coach Wilding offers a number of strategies for pulling off a successful skip-level. If your manager is a frightened little mouse, afraid of their own shadow, I have added some twisted logic gained after decades successfully navigating corporate life without ever meeting with my manager, my manager’s manager or my manager’s manager’s manager. Not to mention the doomed souls who considered their manager to be me.
Give it a whirl! You could certainly do worse, though I’m not sure how.
No. 1: Clue into your workplace culture.
Some organizations “value open dialog and employees taking initiative.” Some organizations have warm, gluten-free cinnamon buns waiting when employees come in every morning and send warm gluten-free cinnamon buns to their homes when they don’t.
To take the measure of your organization’s affinity for employees who are not bound by archaic rules of corporate hierarchy, put a sign on your door. Something not too controversial, such as “Failure isn’t an option here; it’s a way of life,” or “My manager isn’t an idiot, but they’re working on it.”
If the feedback is positive, you’re safe to schedule a skip-level. (Don’t have a door? Might as well go for it; you’re doomed either way.)
No. 2: Involve your immediate supervisor.
Wilding says, “be transparent.” This shouldn’t be difficult, since you’ve spent most of your career trying to be invisible. Wilding advises that you “make it clear that your goal is not to undermine your boss’s authority.” Your manager may believe you. They may also demand you wear a wire, not because they’re nervous, but because it allows them to send in a bunch of HR goons if they don’t like the way the conversation is going.
My advice is that this is a situation where it’s better to apologize later than to ask permission before.
“Sorry I didn’t mention that meeting,” you say when your manager comes bursting into your office, steam coming out of their ears. “I apologize.”
Be sincere and humble and maybe your manager will help you pack your boxes.
No. 3: Define your skip-level meeting goals.
Your manager’s manager did not rise to their exalted position by wasting time. Keep your agenda lean and mean, with only a few minutes at the beginning of the meeting to show photos of your family’s summer vacation. Better yet — show photos of the last summer vacation taken by your manager’s manager’s family, which you had the company’s AI bot scrape off Instagram.
Once you’ve bonded, proceed to your main goal, showing that while your manager is a wonderful person, who has totally earned your respect, you could do their job a whole lot better for a whole lot less money. I guarantee that your willingness to sabotage anyone and everyone, regardless of title or position, all for the sake of furthering your own career, will be appreciated, though this may not be the time to schedule a skip-level with your manager’s manager’s manager.
No. 4: Build the relationship.
Follow up after the meeting, thanking your manager’s manager for their time and their wisdom. Assure them that you will fill in your manager on everything the two of you agreed they are doing wrong, and the areas the two of you decided would be better handled by you.
To keep the relationship strong with your new corporate BFF, suggest regular meetings, preferably at weekend barbecues, and do point out that your manager does not have to be invited. The elevated nature of your conversation would only confuse them, and they would likely eat all the hot dogs.
This effort is almost guaranteed to work, but do be careful if one of your underling’s underlings asks to have a skip-level with you.
Frankly, I’d skip it.
Bob Goldman was an advertising executive at a Fortune 500 company. He offers a virtual shoulder to cry on at bob@bgplanning.com.
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