Lost In The Weeds: When Leaders Lose Direction

“Generally, when a leader struggles, the root cause behind the problem is that the leader has leaned too far in one direction and steered off course.”

Jocko Willink.

While “steering off course” may be intentional, “getting lost in the weeds” (less intentional) is another way to describe when a leader loses direction. Leaders are not invincible – just like their team members, they are human and sometimes need a little extra support from that team to keep the organization from faltering. This blog is for leaders and their team members, helping each other understand the signs and implications and maneuvering through being lost in the weeds.

What Makes a Leader?

Leadership requires a high-level view, guiding a team or organization toward long-term goals. A leader does not necessarily need to be able to do everything their team can do. Effective leadership means understanding and leveraging the strengths of each team member and providing guidance, support, and resources to help the team achieve its goals. A leader’s role is to provide direction, make decisions, and foster a positive and productive work environment rather than personally possess all their team members’ skills and abilities. It’s important for a leader to recognize their limitations and to trust and empower their team to contribute their expertise.

All leaders have varying areas and degrees of responsibility – it’s no wonder they can easily fall victim to losing direction and “getting lost in the weeds.”

How Do Leaders Get Lost in the Weeds?

When the going gets tough at work, most people’s first reaction is to roll up their sleeves and work harder, faster, and longer. Stress levels go up, productivity goes down, and perspective is lost. While it may feel good at first because you’re doing lots of stuff, you’re tangled in the weeds, gulping for air and desperately thrashing around before you know it. It’s not a great place to be. You’re getting your “hands dirty,” being a team player, and gaining the respect of your team, but in the long run, you risk becoming ineffective and, at the same time, making your team ineffective.

When leaders cannot get out of the day-to-day and focus on the bigger picture, they become stuck in the weeds. When a leader refuses to let go of minor projects so they can focus on more business-critical ones, they become stuck in the weeds. When they spend too much time in the weeds deciding to do tasks usually reserved for direct reports or other resources, they risk abandoning their core responsibilities to provide strategic leadership.

The Weeds are a Messy Place!

Chances are there are many other people in the weeds, and they are all getting in each other’s way. It’s all hands-on deck, and roles are becoming blurred. As a leader, if you are now diving into the weeds, it sends out a message, and it’s not a good one. It’s a message of panic and signals that the team isn’t performing. The initial “great, the boss is getting in the weeds” soon turns to “why is s/he here?”, “s/he doesn’t trust us to deliver,” and “we seem to be getting deeper into the weeds than being able to see any light at the end.”

What Can Leaders Do?

Trust the team. Don’t smother key players: give them clear direction, keep them focused, and manage the environment around them. There’s a fine line between being supportive and being smothering. When you support team members, they stay engaged, but when you smother them, you disempower them and ultimately lose them. They no longer feel accountable or able to take the initiative, and that’s a slippery slope. Accountability comes from trust and the absence of fear; the leader’s job is to provide that environment. Of course, you occasionally must make interventions when needed but then get right out because you’ve got your job to do.

Remain focused on the big picture. Strive to remain a transformational leader and avoid becoming a transactional manager. As leaders get mired in detail, creativity and inspiration drain away. Do bring a sprinkling of organization and supervision to the team. Still, your main aim should always be to enhance the motivation and engagement of your team by directing their behavior toward a shared vision.

What Can Team Members Do (and Leaders can learn from)?

Recognize the signs. Learn to recognize when your leader loses sight of the overarching objectives. These symptoms might manifest as an obsession with minor details, delays in decision-making or constant rescheduling, a sudden drop in team morale and productivity, etc. Understanding the early signs provides the insights needed to intervene at the right moment.

Open a dialogue. Once you’ve spotted the issue, the next 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 are reflective prompts, encouraging your leader to think critically about their current approach.

Offer to shoulder some burden. If your leader is overwhelmed with micromanagement, propose reallocating responsibilities. Identify tasks that other 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 team members while freeing the leader to engage in more high-order functions. Encourage your leader to entrust smaller, manageable tasks to other team members.

Advocate for strategic planning sessions. Recommending scheduled sessions can help your leader regain their focus. During these sessions, 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 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. Recognizing and tactfully addressing issues contributes 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.


Leaders and their team members who understand being lost in the weeds and work together to regain direction ensure everyone continues working together with mutual respect and understanding, leading to a successful outcome. If being lost in the weeds is something your organization is experiencing, Success Trek can help. Our unbiased perspective can identify root causes and work with you to create actionable steps that lead to success.

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