Through The Messy Middle: 4 Strategies for Navigating Disruption

Author

Charlene Li
October 22, 2024

Hot take: If your leaders don't believe in disruption, your employees won’t either.

I’m not just talking about top executive leaders, either: I’m talking about leaders across an organization. If they don’t believe in what you’re doing, you’re going to have a hard time creating the change you know is necessary.

If you’ve been a leader for some time, you know that changes prompt challenges. Where and how do you begin in a landscape as disrupted as ours?

Here are four strategies to get you started.

1. Create Alignment for Buy-In and Transparency

This sounds straightforward, but in many ways, alignment is the biggest challenge facing disruptive leaders. To get everyone on the same page, assess your existing alignment. See if everyone can answer these three questions:

  • Who is your future customer?

  • What is your strategy to meet their needs?

  • How are you personally contributing to the strategy’s success?

Not fully aligned? This is where planning comes in. Where do you want to be 18 months from now? Take that vision, and get clear on how you will accomplish it. 

2. Embrace the Messy Middle—and Communicate Through It 

When you start from one place and reach toward another, you’re bound to hit the in-between. It’s this space—the messy middle—that prompts change fatigue. People know they will have to wade through it and don’t want to. It’s uncomfortable.

To navigate this messy middle effectively, leaders must prioritize clear and consistent communication. It’s not “one and done.” You need to: 

  • Describe the middle, and offer context for it. Tell your teams what the “after” looks like, and explain why you must go there. This also means you’ll need to share why your current state is no longer tenable. Your team needs this clarity to commit to the journey.

  • Reassure your teams that it’s going to be okay. Change is hard and scary, especially when the space you’re in now (the “before”) feels comfortable. Build up your relationships with your people, empowering them to speak up when and if the going gets tough. 

3. Disagree Well and Commit Completely

If people are able to disagree well, they’ll be willing to bring all ideas to the table.

We know that the bigger the change, the bigger the conflict. Your job as a leader is to create a culture of strong communication (this includes strong conflict resolution). This goes back to my first point: If everyone is 100% aligned with and committed to the vision, then the disagreements that arise are simply about how to get there. In this way, disagreement is a powerful, generative tool.

4. Embrace Setbacks and Failures

Disruption calls for leaders to reflect on their relationship with failure: What does it look like for you? What does it look like for your team? How do you move forward from the feelings of shame, regret, and disappointment? 

Part of this work involves giving yourself permission to change your mind. Most decisions are reversible. Of course, you want to be thoughtful and informed when you make choices, but sometimes, once you’ve gleaned more information, you need to go in a different direction—and that’s okay.

Every decision allows us to learn, improve, and advance the team. If you try something and it works, that’s great! But there’s value and benefit in trying something and realizing it doesn’t work.

What are some of your biggest disruption leadership challenges, and how do you address them? Hit reply and let me know!

-Charlene

What I Can’t Stop Talking About: 

  • Leveraging AI for career guidance. While Siri might not be able to help you brainstorm career moves, other AI models can help. From generating exploratory questions to analyzing your situation, here are 3 ways AI can kickstart your career reflection.

  • Leadership lessons from Burning Man. It's not just about the art, burns, and music. This unique environment offers profound insights for leaders. From embracing the unknown to fostering psychological safety, here are 5 takeaways to transform your organization's culture. 

  • "Do you have any clarifying questions?" Before asking AI to complete your request, start with this simple query. It's a game-changer for avoiding misunderstandings and maximizing results. Here’s how to get the most out of your chat. 

My Latest: 

  • Catch up on my webinars! You can still review the slides and recordings of my two new webinars. In “Unlocking The Power of Generative AI,” I explain how to set up a generative AI “playground,” three ways to elevate your leadership with step-by-step instructions, and the broad outlines of creating a strategy. In “Developing a Winning Generative AI Strategy for Competitive Advantage,” I walk through the steps needed to create a cohesive AI strategy. 

  • HR: Your Secret Weapon for AI Strategy Success. Is your organization grappling with AI anxieties? In Leading Disruption, I reveal why HR is crucial for effective AI integration. Learn how HR can drive AI literacy, develop governance policies, foster transparent communication, and cultivate an AI-ready culture. TL;DR: HR needs a seat at the AI table. 

  • Is your AI strategy lost in translation? Many leaders believe they're effectively communicating about AI, but the message often fails to reach its intended audience. Catch my most recent livestream, where I talked about how to bridge this communication gap. Then, join me Tuesday, October 29 at 9am PT / 12pm ET, where I'll dive into how to assess capabilities and initiative feasibility. As always, you can catch me on LinkedIn and Facebook Live.

My Upcoming Appearances:

If you want me to speak at an upcoming event or conduct a workshop with your executive team, please drop me a note at [email protected]. 

If this information was helpful, there’s plenty more!

📌 Sign up for updates and early access to my upcoming book, co-authored by Katia Walsh, which is all about creating a winning generative AI strategy.

📌 Want more? Check out my weekly publication, Leading Disruption, on LinkedIn.

Thank you for subscribing to The Big Gulp Newsletter, which goes out to thousands of disruptors every other week to help you on your disruption journey—plus a curated recommendation list of the things I can’t stop talking about. 

Charlene Li

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