The Value of Skip-Level Meetings and How to Leverage Them

Do you have a relationship with your manager’s manager, the ‘big boss’? For many, the answer is ‘not really’ or ‘limited’. And yet, building relationships with those higher up in your business is vital, and a skip-level meeting can be your key to unlocking numerous benefits. I think there’s tremendous value in this article from Harvard Business Review, which I’ve summarised below: 

What is a Skip-Level Meeting?

A skip-level is a direct meeting between you and your boss’s boss, offering a unique opportunity to connect with senior leadership.

Why is it Important?

Regardless of where you stand in the organisational ladder, skip-level meetings become even more crucial as you climb. Here’s why:

  • Broaden Your Horizon: Direct interaction with senior management helps you align better with the company’s strategic direction.
  • Build Trust: Developing a rapport with your boss’s boss establishes trust, which is essential during transitional phases.
  • Promote Advocacy: These meetings are a platform to highlight achievements and garner support for team resources and personal growth.

How to Navigate Skip-Level Conversations

Gauge your workplace culture to see if such a request is appropriate or viewed as a threat.

Reflect on previous feedback and interactions with your immediate supervisor to get a sense of their expectations.

Involve Your Immediate Supervisor

If you decide a skip-level meeting would be beneficial it’s important to have a candid conversation with your immediate boss.

  • Communicate the benefits of the meeting for you and the entire team.
  • Seek your boss’s advice on maximising the outcome and respecting workplace dynamics.

Define Your Objectives

Prepare for the meeting by:

  • Setting clear expectations.
  • Outlining specific challenges and opportunities.
  • Presenting data that would appeal to senior management, emphasising impacts and results.

Ask Meaningful Questions

Your primary goal is to listen. Follow the 70/30 rule (listen 70% of the time and speak 30%). Some strategic questions you might want to consider asking:

  • What do you see as the main challenges for our team?
  • How do you envision our team’s future role?
  • What market trends should we focus on?
  • What are your long-term aspirations for our company?

Foster the Relationship

Building a lasting relationship involves:

  • Demonstrating respect, integrity, and initiative.
  • Expressing appreciation post-meeting via emails summarising key points.
  • Being accountable for promises made during the meeting.
  • Scheduling follow-up meetings to nurture the relationship.

Investing in upward relationships, especially with skip-level managers, is crucial for career growth. Leadership isn’t just about managing downwards but also adeptly navigating the dynamics above. 

A really useful idea.



Search the whole etc Playbook...

We have 100's of articles to help you with leadership, growth, talent and running a better business.

Agency Founders Surgery - free 1 to 1.

If you have something on your mind, a challenge you’re wrestling with or just want an alternative point of view, I’d be very happy to lend an ear and maybe help you start to unpick the issues.