How to Hold an Effective Skip-Level Meeting and What Questions to Ask

How to Hold an Effective Skip-Level Meeting and What Questions to Ask

How to Hold an Effective Skip-Level Meeting and What Questions to Ask

Do you know what’s going on in your business? What’s REALLY going on behind the smoke and mirrors?

Or do you get all your information from your direct reports? Leaders that are disconnected from the day-to-day reality of their teams can face problems further down the line. It gets harder to implement the vital changes needed to scale your business. You’ll meet resistance and negativity, with little buy-in for your goals and strategies.

The answer? It’s simple. Introduce skip-level meetings. You may feel they’re too big a time commitment. But I can tell you one thing. Every one of our clients who have implemented them has seen a massive difference. Suddenly, they have no holds barred insight from the people doing the work. 

What is a Skip-Level Meeting?

A skip-level meeting is a 1:1 session between a team member and their boss’s boss. Importantly, this happens with the full knowledge of the person’s manager. For example, a department head could set up a meeting with someone who doesn’t report directly to them. Or a vice president could arrange to “skip over” the sales manager to meet with a salesperson directly.

Why Use Skip-Level Meetings?

These meetings will allow you to ask questions about things which wouldn’t normally cross your desk. They can reap so much information. Whether it’s weaknesses in your current architecture, difficulties with a certain manager or organisational changes that are getting people worried, you now have a view that hasn’t been filtered through senior management. This is invaluable.

They’re an ideal opportunity to learn how staff are getting on, hearing this directly from the horse’s mouth. Senior leaders can use these insights to speak with greater knowledge about how things are going for their organisation and its people. Strategies and OKRs can be shaped accordingly.

Skip-level meetings also improve visibility for both people involved. For the senior leader, it’s a chance to demonstrate their interest in people’s wellbeing. They can build rapport and trust – essential ingredients for a healthy, high-performing culture. By being more approachable, they can break down any sense of ‘them and us’. 

For the team member, it’s a chance to get noticed and can be great for their career prospects. They hear about plans and feel their view is appreciated and welcomed.   

How Should You Prepare? 

Open and honest communication is essential before you embark on skip-level meetings. Make clear your expectations beforehand – these meetings are not about giving direction or upending any established decision-making. Your people should understand that you’re not trying to subvert anybody on the team or display a lack of trust in a particular individual. Skip-level meetings are a regular and repeated practice you want to implement for everyone.

It can be helpful to spell out the value exchange of these meetings, so people appreciate why you’re introducing them. Tell everyone that the meetings will provide context on what’s happening at a senior level and coaching or mentorship over specific things. 

Don’t try to meet with everybody, as the meeting cadence may get too big. But make sure you meet people from all your teams, gaining some granular detail at all levels.

What Questions Should You Ask in a Skip-Level Meeting? 

Keep these meetings informal and relaxed. Remember, they’re about building a rapport, which is easiest if there’s a certain level of informality. The person you’re speaking to may be nervous, so put them at ease and reassure them with open questions. We tell clients to start every meeting with good news to get them talking about something positive. Here are some suggestions for possible questions you could use. 

Q1. What projects have you particularly enjoyed in recent weeks?

Here you’re getting to grips with their feelings about their job. You’ll get an insight into their talents and strengths. This can be helpful for future projects as you’ll start to build a picture of people’s enthusiasm for tackling different work areas.

Q2. What makes you feel proud (either at home or work)?

You could talk about hobbies here as well as their family life. This is how you start to understand what makes people tick. Equally, they may want to tell you about something they’re particularly proud of at work. And you can say thank you for their hard work.

Q3. Are any big challenges getting in the way of you doing a good job?

You must work out if they’re unhappy with certain aspects of their role. They may not feel comfortable talking about these things with their direct manager, but encourage them to open up to you. Perhaps you can find ways to address any issues before they blow up into something bigger. The last thing you want is negativity to take root in your teams.

Q4. Is anything about our current strategy or vision unclear?

There’s no point in having a strategy if your teams don’t understand it. Here’s an opportunity to convey your business’s priorities and ensure they’re ‘landing’ with your staff. It’s also a good place to discuss how their role directly supports the company’s goals.  

Q5. Where do you see yourself in three years?

Get inside the head of this person and understand their motivations. Do they want to stay in the same department? Are they interested in becoming a manager? This will help you identify your future leaders. By understanding their ambitions, you can develop and foster them. And they’re less likely to jump ship.  

Q6. What do you wish your manager would change/do more of?

Make it clear that this question isn’t about blame or attribution. It provides you with general feedback when coaching your direct report and their immediate boss. This question is an open-ended chance for team members to offer their opinions about how their boss could improve. Thank them for their honesty and coach them on how to raise this feedback with their boss.

Q7. Tell me about your favourite book, podcast or movie

Finish on a lighter note. Get chatting about the latest book they’ve read or a film they’ve watched. Get to know them on a personal level and continue to build rapport. They will appreciate the time you’ve devoted to this conversation. You’re making your people feel valued, which is always good. 

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Dominic Monkhouse

Leadership Expert

Dominic Monkhouse is a proven architect of business growth with a demonstrable track record. As managing director, he scaled two UK technology companies from zero revenue to £30 million in five years. Since 2014, Dominic has worked as a CEO and executive team coach, helping ambitious CEOs and their leadership teams reach their full potential and achieve sustainable growth. He is the host of “The Melting Pot with Dominic Monkhouse” where he talks with some extraordinary thought leaders, fellow business authors, and CEOs to absorb their wisdom. Dominic is the author of F**K PLAN B: How to scale your technology business faster and achieve plan A, an exciting blueprint for cultural change and business transformation.


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