Climbing the corporate leader surely can be rewarding. Bigger impact, fancy corporate title, maybe even some nice, fat paycheck. But being a senior leader is not just bells and whistles. Many dangers are waiting for inexperienced leaders and leaders isolation is perhaps the most dangerous one.

You can use many tools to escape your Ivory Tower and break the isolation bubble. One of the most powerful ones are skip level meetings.

What is Skip Level Meeting

The idea of a skip-level meeting is simple. It’s a 1:1 meeting with your non-direct report. You go 2 - 3 levels (or more!) down the hierarchy and meet with the people that your managers are managing.

For you, the purpose of the meeting is to get out of your bubble. Learn how do people feel about the work they do. What do they think about the culture, the processes and the organisation around them? What could be done better? What issues need to be resolved?

Skip-level meetings are beneficial for the employees, as well. It’s an opportunity for them to talk to you. Raise their concerns. Get to know you and see the face and the real person behind the fancy corporate title. It’s a place to discuss the organisation’s long-term plans and strategic direction. Does it resonate with them? Do they understand its impact?

Unfortunately, skip-level meetings can backfire if done wrong. You have to juggle three players in this game. Yourself, your non-direct reports and a manager you are “skipping”. It’s a game of trust as your manager can easily consider your skip-level meetings as a sign of mistrust and an attempt to find “dirt” on him. It’s a delicate situation that needs to be played carefully.

Powerful leadership tool. Simple in theory, complex in practice. Let’s see how you can use it well.

How to run effective skip-level meetings

As usual, preparation is the key. You need to prepare your managers, non-direct reports and yourself. Start with the managers.

Prepare your managers

Open and clear communication is key here. Talk with your managers and tell them you will meet with their reports. They may get a bit anxious so explain your intentions and the goal you want to achieve with those meetings. This is a critical step. They have to feel safe that this is not a process that will be used against them. That it’s not some kind of witch hunt to find something that will be later brought up during their performance review. Tell them what questions you will be asking and how you will work with the information you receive. You need to bring them on your side as you will need their help to prepare yourself and work with the feedback you will gather.

Prepare your non-direct reports

People in your teams also need a heads-up. A sudden, unexpected 1:1 meeting with a senior manager can bring some people on the edge of a heart attack. Let’s try to avoid that. Hiring is hard after all.

Same as with your managers, let them know what to expect, what questions you will be asking and what your intention is with those meetings.

Prepare yourself

Finally, you need to prepare yourself. Work with your manager to get to know people in your teams. Ask him about their work and career growth details, any issues they are dealing with and even some basic personal stuff. You don’t want to start the meeting by asking “Ok, so who are you anyway?“. That will look really, really bad. Make sure you do your research. This will make a much better impression on your teammates and show them that you are interested in them.

Schedule the meetings

Scheduling skip-level meetings can be challenging. If you have many reports, you might need to reserve more time in your calendar to meet with them regularly. As a rule of thumb, you should meet with every non-direct report at least once per quarter. There is an important aspect of making skip-level meetings a regular, recurring event. It normalises them. People will get used to those and will treat them as a normal part of the process. That’s good, that will reduce their stress and will help them open up.

If you don’t have a regular skip-level schedule and you set those ad-hoc, it will always create an impression that you are jumping to action because “something” has happened.

Run a meeting

Same as with 1:1 meetings, having a well-thought-out agenda will help you to guide the conversation and put a helpful framework for your reports to follow. Don’t be too strict though. Your goal here is not to tackle all the checkboxes on the list but to get first-hand information on what’s happening on the front lines. So if you notice something interesting, just follow it and don’t worry too much about missing some agenda point.

Agenda for skip-level meetings

The purpose of skip-level meetings is significantly different than 1:1s. Your goal is not to manage or grow those people. That’s your manager’s role. You are here to understand what they are dealing with in their everyday work. To gather the information that will allow you to build a detailed picture of what is happening inside your teams and make strategic decisions based on it.

Start with a quick check-in, asking about their well-being and how they feel. Try to set an informal and chilled energy for the meeting. The more relaxed they will be, the more they will open up and give you honest information.

Then ask them a few open-ended questions. Keep the conversational form, don’t make it an interrogation. If you see something interesting in their response, don’t be afraid to dig deeper and follow on the topic. Sometimes the most precious piece of information is just around the corner. Don’t focus just on the negatives. It’s also important to know what works and what your teams are happy about.

Questions for skip-level meeting

You can find some example questions below. You don’t have to ask all of those at once, but it’s good to ask about different aspects of your reports’ work to get more holistic results.

General feedback

1. What, in your opinion, works well in the company right now?
2. What areas are not working well?
3. What is the biggest obstacle that is slowing down you or your team?
4. What do you think is our biggest strength?
5. If you could change one thing, or improve one process in the company, what would it be?
6. On a scale from 1 - 5 how much would you recommend working in our company to your friends?
7. What is the one thing I should pay more attention to?

Culture and collaboration

1. How would you describe our company’s/team’s culture using just three words?
2. What are the most important values and principles we follow in our daily work?
3. How often do you have a chance to help or support people from other teams?
4. How often did you receive support from other teams?
5. How well, in your opinion, our daily live aligns with our official values?

Growth and personal development

1. Do you feel your work gives you an opportunity to learn and grow as a specialist?
2. Do you feel you receive enough support and guidance on your personal development path?
3. Do you see a path for yourself to grow and be promoted within the organisation?
4. What would help you grow more and improve as a specialist?
5. What was the last thing you’ve worked on that helped you grow and learn?

Vision and roadmap

1. What do you think about the company’s vision? Do you think it puts us on a proper path as an organisation?
2. Are your team’s goals aligned with your expectations of what the team should be working on?
3. What, in your opinion, is the most important part of our strategy?
4. How would you summarise the long-term goal of your team?
5. What do you think was missed or should be emphasised more in our long-term plans?

Focus on issues, not on people

The key aspect of successful skip-level meetings is to keep the focus on objective issues, not on people. Your goal is to get as objective information as possible, focusing on facts, not on speculations and interpretations. It’s very easy to switch to personal feedback mode, but you should avoid it at all costs. Gather the information, positive and negative, and understand what are your teams dealing with. Later, once you gather enough data, from different people and different perspectives, you can analyse it and conclude whether there are some issues with people or processes that need to be addressed. On the meeting itself, focus on listening.

Be a sponge.

Keep your reactions and body language in check. It’s natural, when receiving negative feedback, to jump right away to explaining and refuting it. “Let me explain to you why you are wrong… ” is the surest way to never receive honest feedback again. Even if you truly disagree with the feedback, focus on why this person thinks that way and incorporate this information into your research.

Don’t play a manager

A common mistake senior leaders make in skip-level meetings is overstepping their bounds and overriding their managers.

You don’t want to do that.

Everything between people in the organisation works on trust. High-trust organisations are lean and effective, whereas low-trust are oppressive and bloated. If you undermine your manager, give an impression to his reports that you are acting against him or using skip levels to find dirt on him, you will create irreversible damage to the trust between you, him and his team.

You want to give your manager space to be a manager to their direct reports. While you might be ultimately running the entire team, department, or organization, it’s their direct reports, not yours.

Don’t make decisions. Your manager should be the one making decisions within the scope of their team and domain. You may undermine them if you make immediate decisions in that skip-level meeting without consulting them.

Don’t jump into action If you hear something surprising or distressing, resist the urge to immediately act on it or even comment. Again, you are here not to manage, you are here to listen. Instead of jumping to action, thank the person for the feedback and give yourself time to calibrate and analyse it. If needed, bring this topic to the manager and work with him on resolving it.

Follow up

Make sure you follow up on any action points you’ve agreed in the meeting. Showing your employees that their feedback is important to you is a crucial part of a successful feedback loop. It helps to reinforce the trust and gives you credibility as an effective leader.

Bring all related concerns and issues you’ve gathered to the manager. Work with him to resolve them. If needed, coach and provide support but give them space to work on solutions. This way you avoid overstepping your role and still use the information from skip-level meetings to improve your teams and grow your managers.

People in the team will trust you because they see that bringing feedback to you works. Your managers will trust you because you are not working against them but instead, you help them grow. This is the way.

Sometimes you will receive feedback that is hard to address. Feedback about topics that are outside of your reach. Above your pay grade. Realistically you are not able to solve everything. Even senior managers have limits and your people know it. But you can at least let your teammates know that you did what you could, for example by raising this topic with someone from the executive leadership team or on a related leadership group.

It’s not easy to break the bubble

Running well-prepared skip-level meetings with all your reports is a lot of effort and can be quite a stretch for a busy senior manager. As difficult as it may be, it’s still the best tool you have in your hands to break the leaders’ isolation and be aware of what is happening on the front lines of your organisation.

And if you think the cost of staying in touch with your teams is high, trust me, the cost of being detached and isolated in your ivory tower is incomparably higher. You just pay it later.

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