What To Do When Your Leader Is Stuck In The Weeds

Leadership involves a high-level view, guiding a team or organization towards long-term goals. But what happens when a leader gets lost in the minutiae, or as we often say, gets “stuck in the weeds”? Here’s how to navigate this tricky situation:

Recognize the Signs: Firstly, learn to recognize when your leader is losing sight of the overarching objectives. These symptoms might manifest as an obsession with minor details, delays in decision-making, or a sudden drop in team morale and productivity. Understanding the early signs will equip you with the insights needed to intervene at the right moment.

Open a Dialogue: Once you’ve spotted the issue, the next crucial step is to initiate a candid conversation. Opt for open-ended questions like, “Do you think we are focusing on the right priorities?” or “How do you feel our current projects align with our long-term goals?” These questions serve as reflective prompts, encouraging your leader to think critically about their current approach.

Offer to Shoulder Some Burden: If you find your leader overwhelmed with micromanagement, propose a reallocation of responsibilities. Identify tasks that other competent team members can execute effectively. Explain how this redistribution allows your leader to concentrate on strategy, problem-solving, and other higher-order functions that require their unique expertise.

Suggest Delegation and Trust: Delegation can be a transformative skill for any leader. Frame it as an opportunity for team growth, illustrating that delegation can help develop junior team members while freeing the leader to engage in more cerebral tasks. Encourage your leader to entrust smaller, manageable tasks to other team members as a start.

Advocate for Strategic Planning Sessions: Recommending scheduled strategic planning sessions can help your leader regain their focus. During these sessions, actively review and realign long-term objectives. Discuss key performance indicators (KPIs) and other metrics that can serve as markers of success, helping your leader rise above the weeds and realign their vision.

Provide Constructive Feedback: Conclude by providing tactful yet impactful feedback. Consider doing this during a formal review session or as part of routine one-on-one meetings. Your critique serves as a mirror, reflecting both the good and the areas needing improvement, thus providing a much-needed reality check for your leader.

A leader stuck in the weeds can slow down an entire team’s progress. By recognizing the issue and tactfully addressing it, you contribute to a more functional and focused work environment.

Lead from Within: When you help your leader see beyond the weeds, you’re not just clearing a path for them—you’re paving the way for the entire team’s success.



#1 N A T I O N A L  B E S T S E L L E R

The Leadership Gap
What Gets Between You and Your Greatness

After decades of coaching powerful executives around the world, Lolly Daskal has observed that leaders rise to their positions relying on a specific set of values and traits. But in time, every executive reaches a point when their performance suffers and failure persists. Very few understand why or how to prevent it.

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Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR, Inc.com, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.

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