Skip level 1 on 1

Skip level 1 on 1

photocredit: @amyhirschi | unsplash
[content developed based on Lighthouse blog: 55 Skip Level Meeting Questions to Improve Your Managers and Engage Your Employees]

How to set up skip level 1 on 1

Set expectations to remove the risk of people having the wrong idea coming into them and explain to people the reason for skipping level meetings. The skip level meeting is about improving communication and the flow of information. As a manager of managers, here are some benefits of the skip level 1 on 1

  1. Demonstrate care personally 
  2. Team pulse
  3. Build trust. 1 on 1 meeting is a two-way conversation. The meeting provides a rare opportunity to let team members know what you are working on to help the team
  4. Find out how you and your managers are doing, getting feedback.

Here are the three steps to set up expectations and scheduling skip level 1 on 1

  1. Tell your managers 
  2. Tell your skip level team members 
  3. Schedule them in a manageable way

Mindset for skip level 1 on 1 meetings

In the past, we tend to praise all the superstars. As Kin Scott has reminded us that keep in mind, the rock-starts provide stability in the organization. Many of us have been in and out of each column at different phases of our careers. Keep an understanding of where your people fall at the given moment will help frame the conversation. 

I like this framework over the nine-box performance review framework, because this framework focuses on people’s strength rather than labeling people. As Kim Scott pointed out, “I don’t think there is any such thing as a low-potential human being.” Think about this, sometimes a person’s poor performance might just be the boss’s fault. As we are not setting up this person for success, or utilize their strength. Instead of thinking about performance management, think it as GROWTH management.

“Superstar”“Rock Star”
Change agentForce for stability
Ambitious at workAmbitious outside of work or simply content in life
Want new opportunitiesHappy in the current role
Be a Kick-Ass Boss Without Losing Your Humanity (p. 45). St. Martin's Publishing Group. Kindle Edition. 

Skip Level Meeting Questions to Improve Your Managers and Engage Your Employees

Table of Contents:

Skip Level Meeting Questions to Build Rapport—Care personally

As Camille Fournier, author & former CTO of Rent The Runway, has championed in a post on her blog:

“As a leader, you will lead people who want Relatedness in their job. They want you to know about their family, their hobbies. They want to chat with you about their weekend, their trips away. They want to get lunch sometimes.”

I am a big fan of Kim Scott’s Radical Candor. “Care personally, Challenge directly”. The foundation is to care personally. Build Rapport is a natural place to start the skip 1 on 1 relationship. (It is the start for any manager to reports relationship.) To start, is to understand what motivates each person on the team.

Here are some questions 

  • What do you like to do in your free time? What are your hobbies?
  • If they have children: How is [name of child] doing? (Ask something related to their age like starting school, playing sports, or other interests.)
  • What drives you? What motivates you to come to work each day?
  • Where did you grow up? Where did you go to college?
  • What’s your favorite part about living in [your city/town/region]?
  • What’s your favorite book you’ve read / podcast you’ve listened to / movie you saw recently?
  • What made you decide to become a(n) [engineer/marketer/sales person/customer success/role]?
  • Who do you think makes the best (regional food for your area: BBQ, burritos, etc)?
  • Have a trip planned or one recently you really enjoyed?

In the past, we were taught to belive that people do better work when they find that work meaningful. This is true, and it is on us (managers, leaders) to provide that meaningful work. But we do need to understand that there is nothing wrong with working hard for a paycheck to support the lifestyle we have/want. As professionals, people can be responsible and do a good job. For this reason, I love this perspective

…your job is not to provide purpose but instead to get to know each of your direct reports well enough to understand how each one derives meaning from their work.” I believe this applies to direct reports and people who roll up to them. 

Scott, Kim. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity (p. 51). St. Martin's Publishing Group. Kindle Edition.

Skip Level Meeting Questions to check team pulse

Asking questions for feedback on teams is a great way to uncover them as Steven Sinofsky writes:

“For a larger organization, there’s a benefit to spending time in skip-level dialogs on the efficacy of the work environment. Asking questions about the velocity of code, collaboration, getting things done, and so on. In any organization of size, a manager of managers is where action can (and should) be taken to avoid the perils of a stagnating organization.”

To avoid a “stagnating organization” here are some questions:

  • What has been the work highlight/lowlight from the past (time period)?
  • What’s one thing your team should stop doing? Why that?
  • What’s the biggest bottleneck or blockers that affect you and your team doing their jobs well?
  • If we had a budget to get you any one thing for you to make you better at your job, what would you want?
  • How is you / your team’s workload? Do you feel it’s too little, too much, or the right amount?
  • What are your biggest concerns about [recent change y]?
  • What tweaks would you make to [change x] to help you and your teammates?
  • What’s your favorite part about working on your team?
  • If we made [change z], how would you feel about it? What do you like / dislike about that?
  • What’s one thing we could improve based on how <last major project they were on> went?
  • What do you think your team does really well? What should we be sure you’re able to continue doing?
  • What’s the most important thing we do to help you be successful working (remotely)?
  • Who do you believe are the valuable people on your team? What makes them essential?

While taking a team pulse, look for problems as well as positives. It is an excellent opportunity to hear from the team about past efforts, what is working, what can be even better.

Skip Level Meeting Questions to build trust.

Same as any 1 on 1 meetings, skip level meeting is a place for conversation. It is important to learn how team members are doing. At the same time, it is also an opportunity for the managers to communicate, articulate what is on our plate. Get the members to be involved in the initiatives that we are focusing on.

  • I have been trying (X). What’s one thing I can do to improve the performance of the team?
  • I am working on (X). If you were managing the team, what would you do differently?
  • Is there anything that would be productive for me to re-explain to our team?
  • Am I providing enough clarity on our direction?
  • (X) is something I am working on. Do you have any suggestions that team members can contribute to it?
  • (X) is a challenge I am facing right now, do you have any suggestions on how team members can contribute and help?

Showing vulnerability is hard. But showing vulnerability is human. Many times, being a manager of managers, the belief is to shelter the team from problems. There is much truth to it. Sheltering the members from problems can help the team focus on their own work rather than being distracted. But we know, telling people what to do doesn’t work. The only way to drive results is collaboration. That includes collaborating with skip-level team members. Rally the team behind us to achieve a common goal. As managers, we will get more done if we listen and incorporate team members’ thinking in ours andours into theirs. I commonly refer to moving the team as a fleet towards the same destination rather than individual sailboats bobbing along with the tide. I often catch myself that I am moving too fast without the alignment of the team. I left too many people out of the decision-making process. To help the team better decide how to decide, I recently ran a workshop on “Leadership decision making” based on Dr. Vroom’s theory and research. The skip level 1 on 1 meetings are great opportunities for managers to present the challenge and align the team. No one is superhuman, showing that your frustration and get help from team members are human.

Skip Level Meeting Questions to get feedback for you and your managers.

Feedback is a method we employ to help ourselves grow and help the managers who report to us to grow. When gathering feedback, my mindset is to learn how I can be better and how I can help my managers be better, rather than what was wrong. Feelings are real, and we can’t tell people what to feel. By now, I hope we’ve built understanding, Rapport, and trust for members to provide candid feedback safely. (Read more about Michael Dearing’s Orange Box described in Kim’s book Page135.) When gathering feedback, my preferred framework is “Situation, Behaviour, Impact“. For these questions, dig deeper to understand the situation, focus on actions, not the person. What is the underlying cause of the situation, what is the impact on the person you can follow up to address/help? If we can gather information from several members of the team, we will get a fuller picture of the situation and then improve.

Here are some ways to ask for feedback:

  • If you were in charge of the team you work on, what’s one thing you would do differently? Why?
  • What could I do (or your manager do ) for you to be successful in your current role?
  • What do you need less from me (or your manager) for you to be successful in your current role?
  • Do you feel you’re getting enough feedback from your manager? Why/Why not?
  • When was the last time you had a conversation with your manager about your career? How did it go?
  • Are you happy with your career progress here? Why/why not?
  • What is a recent situation you wish your manager or I handled correctly or could have handled differently?
  • What’s the best part of working with <their manager>?
  • What’s the hardest part of working with <their manager>?

What to do with the feedback? Some of the feedback will guide us to correct the course, some of the feedback will guide us to refine our approaches. Some other feedback will guide us to be a better coache to the managers we manage. Not to forget that some of the feedback needs our immediate attention. (Read more about Managers Fix-it week described in Kim’s book. P135.)

We want to align the team, solve problems. But we also don’t want to undermine the managers. We don’t wish teammembers to form a habit to always go around the managers. Sometimes, a well-intentioned member might bring some ideas to us, and the ideas sound great. Be very diligent in what we do with these ideas. If we say “That sounds great” without a modifier to the comments, it can be interpreted as “That sounds great, go ahead do it”. As a result, the member will run with the idea and left their managers to feel we are undermining their authority or the members are undermining their authority. To avoid this we can ask:

  • Would you bring this idea to your manager, or would you like me to discuss your idea with your manager on your behalf?

Skip Level Meeting Questions to ask Every Time

Depending on the situation and growth stage of the team, the skip level 1 on 1 meetings can be an opportunity to give praise and recognition (do this in person, do this frequently, do this with specifics); triage problems, and manage crises. Many factors affect what questions to ask during the skip 1 on 1 meetings. Not every meeting will result in follow-up action. But if things surfaced during the meeting requires a follow-up action, be sure to recap it at the end of the session. Based on the discussion, identify what team-member is accountable to do and what we are accountable to do. Fail to follow through, we will lose the trust we built. 

“Leadership is solving problems. The day soldiers stop brining you their problems is the day you have stopped leading them. They have either lost confidence that you can help or concluded you do not care. Either case is a failure of leader ship — Colin Powell”

One question I always ask is:

  • What could I do or stop doing that will make it easier to work with me?

Wrap up

Remember what’s at stake.

Care personally, challenge directly. A skip level 1 on 1 meeting is a place for conversation. For both people to benefit from these meetings, stay organized, stay prepared, follow through when appropriate. When we build enough trust, we can use the skip level meeting tp challenge our members directly. Guidance is a gift. Many members desire clear guidance, want to hear from their manager’s manager. They want to know what is the North Star for the team. Don’t save up the “challenge directly” to the end-of-year performance review.

Here is what Kim Scott suggested how to frame it: “I’m going to describe a problem I see; I may be wrong, and if I am I hope you’ll tell me; if I’m not I hope my bringing it up will help you fix it.”

Last reminder when thinking about what is the best use of the skip level 1 on 1 meetings:

Praise in public, criticize in private. 

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