Impressing your boss is a good way to succeed in your role, but climbing the ladder often requires that you get on the radar of the larger leadership team – your boss's boss, or maybe your boss's boss's boss. No matter how complex the chain of command, there are often unspoken rules and stigmas about going over your boss's head. And breaking them could set you further back in your career.
It takes emotional intelligence to navigate these invisible boundaries. When done with self-awareness, soft skills, and the right motives, you can work toward building relationships with leaders in the organization – without stepping on your boss’s toes or breaking a cultural norm.
[ How does your EQ stack up? Read also: Emotional intelligence test: 5 self-evaluation tools for leaders. ]
Five rules for how to deal with your boss's boss
Consider these five etiquette rules, shared by veteran IT leaders, for interacting with your boss’s boss.
1. Focus on work and shared passions
It’s natural to want to be recognized by the leaders in your organization, and the best way to go about that is to focus on doing great work, says Matt Mead, CTO of SPR.
"First, employees should always work to master and excel in their job,” says Mead. “That is the necessary foundation upon which you earn the right to be promoted by your boss and the primary way that I’d recommend for anyone to get more visibility in their organization. Top performers organically get noticed – horizontally and vertically – in a healthy organization.”
Once you’ve made a name for yourself as a reliable, consistently high-performing member of the team, ask your boss for ways you can start to raise your profile even more.
“You can simply tell your boss that you are seeking to be more visible in the organization and why it is important to you,” suggests Mead. “Ask your boss for recommendations on tasks you can do to get more visibility by his boss and others in the organization. Unless you work in a very old-school environment, having a relationship with your boss’s boss is normal and encouraged.”
You could also investigate organic ways to have interactions with your boss’s boss, such as joining committees or working groups they’re involved in and passionate about, Mead suggests.
2. Go bold, respectfully
You can, of course, be somewhat bolder in getting the attention of the leaders in your organization by, for instance, scheduling a meeting or walking into their office. The key is to be respectful in your approach and remember who you are representing in your words and actions.
Jason James, CIO of Net Heath, suggests one surefire way to get on the radar of the organization’s leaders: “The best way to get the attention of your boss’s boss is by presenting to a larger audience.
“Be bold and ask your boss for the opportunity to present at an upcoming multi-departmental meeting or event on their behalf,” he continues. “Once given the opportunity, be prepared and polished as possible. You are representing not only yourself but your department and your boss. Presenting to a larger audience allows you to get on the radar of not only your boss’s boss but also other leaders in the organization.”
3. Bring your soft skills
It’s easy for leaders to recognize strong talent and career accomplishments in their employees. But if you want to form a relationship with your boss’s boss, you’ll have to bring your soft skills as well. These are core to developing a real connection and making a lasting impression.
“Be trustworthy and honest. Management is always looking for employees who they can trust, as confidentiality is key to keeping a business competitive. Being trustworthy is a valuable trait for any employee to have,” says Kassie Rangel, senior director of IT for HealthMarkets.
“Own your mistakes. Doing so will help senior management see you as an honest employee who isn’t trying to cover their tracks,” Rangel continues. “And remember to be confident, but not arrogant. Being a team player who brings confidence is key to being noticed, whereas being arrogant can be perceived as flaunting and may put off others.”
4. Don't leave your boss out
Forming a relationship with your boss’s boss is one thing. Leaving your actual boss out of the loop is another. Make sure that if you are going over your boss’s head, you have a good reason, says Jonathan Feldman, CIO for Asheville, NC.
“You need to think about why you are skipping the chain of command,” says Feldman. “It’s ok to do, but only when there’s a payoff for the organization. Is it time-sensitive? Is it critical? Will it be more efficient?”
When there are situations in which you communicate or work with your boss’s boss, be sure to let your boss know, Feldman advises. “It’s not only polite but also good for the organization and your survival and prosperity to make sure that you clearly and accurately communicate what went down to your immediate supervisor.”
5. Follow two golden rules for dealing with any leader
In any organization, there may be unspoken rules or cultural norms for interacting with the leadership team. If you want to play it safe, follow two golden rules when dealing with your boss, your boss’s boss, or people up the chain. Be transparent, and ask for help when you need it, says Sanjay Malhotra, CTO of Clearbridge Mobile.
These two things will not only make a good impression but will also help develop an open line of communication that will build trust and transparency, Malhotra notes. “Keep leaders informed, and ask for help and advice when needed. Combined, these two things show leaders that you not only take ownership of your work but show that you are invested in the company as well.”
Malhotra offers some advice on how to go about this: “Make a point to ask for a leader’s advice every so often, and make it count,” he says. “You don’t want to ask for advice on something trivial. By inviting leaders into the process of finding or validating a solution, you’re showing how much you value their opinion.
“Secondly, if you are experiencing challenges in your work, your leader should want to hear about them. Whether things are going well, or not so well, communicating with the leaders of an organization helps you build mutual trust and integrity.”
Bonus tip: How leaders should handle skip-level meetings
What is expected from leaders during skip-level meetings - where a leader "skips" over a manager to speak directly with an individual contributor? Jason Hall, senior product manager for SentryOne, encourages skip-level meetings as an team engagement technique. Consider these four practical tips for leaders that he recently shared:
- "Skip-level meetings should be shorter (maybe 15 minutes) and less frequent than one-on-ones. During skip-level meetings, you can learn amazing things about the people on your team and discover multiple opportunities to help them serve your customers and develop their careers."
- "Skip-level meetings also help you organize your team to ensure that it includes diverse skillsets that complement each other within a business function. They also let you know where to turn to meet business needs as they arise."
- "Before initiating skip-level meetings, be sure to give your direct reports a heads up. If you establish skip levels without discussing them with your team leaders first, you risk damaging the trust you’ve worked to build with them."
- "One final note: Once you’re in the habit of holding skip-level meetings, be wary of “grandparenting.” This happens when the leader (grandparent) appears to favor the individual contributors (grandchildren) and taking their direct reports (children) for granted. Grandparenting can cause your direct reports to feel neglected, while those who report to them feel glad to work with such fun and positive leadership. If you find yourself wondering, “Why do most people love everything I do while the people right next to me are having a tough time?” you might be grandparenting."
[ Do you make thoughtful decisions? Read also: 4 styles of decision-making: A leader's guide. ]
This article was originally published in 2019. It has been updated to include additional information and updated data.
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