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Writer's pictureMaya Grossman

How To Get Out Of The Weeds

You're a high achiever. You get things done. Your to-do list is your best friend. But here's the problem: being the go-to person for execution can trap you in the weeds. You're buried under tasks and projects, and guess what? It's costing you that promotion.


Why? You're missing out on the bigger picture because you're so focused on the minutiae.


This is the reason even though you are working your butt off; your manager promotes your colleague who gets a lot less done. You're seen as a doer, not a leader, which means opportunities for strategic impact go elsewhere.


Symptoms of Being in the Weeds:


Here are a few warning signs that indicate you are way too deep into the execution:


  • You oversee every detail of your team's work, needing final approval on everything.

  • You often do tasks yourself, thinking it's faster than delegating.

  • You're worried your team won't respect you if you're not involved in every detail.

  • You only feel valuable when you're hands-on, so you stay busy with tasks.

  • You have ideas but never find time to develop or pitch them.


If that sounds familiar, keep reading, my friend. I'll show you how to escape this vicious cycle and get out of the weeds.



Transitioning from Execution to Strategy


Real talk? Part of the reason you are stuck in the weeds is that it’s comfortable.


You know how to do it; it doesn’t scare or challenge you. You also keep earning praise for doing a good job. What’s not to like?


Well, the lack of progress and the frustration of being overlooked for bigger and more impactful roles (that usually come with a nice increase in your earnings).


So, how do you ditch the weeds and get noticed as a leader? It’s a journey, but here’s how you can start:


1. Balance Your Strategic Horizons


According to McKinsey's "The Alchemy of Growth," leaders should focus on three strategic horizons: optimizing current operations, expanding related businesses, and creating new ventures.


We’re going to call them Execution, Strategy, and Innovation. The higher up you go, the more you need to focus on the latter. But it’s not an either-or; it’s a balance. Initially, 100% of your time will be spent on execution. Then 80% and 50% and eventually almost no time at all.


It’s a natural progression—you are making room for your team to master their execution so that they can eventually grow into strategy.

Start by identifying where you are spending your time right now. Are you all in the weeds, or do you have room for strategic work? If you have no time for thinking, delegate, automate, or eliminate whatever is standing in your way.


Tip: Implement the 80/20 rule, which states that 80% of tasks should be delegated, leaving you with the 20% that require your unique expertise.


2. Delegate and Empower Others


There are usually two reasons why you don’t delegate:


  1. “You problem” - you have trouble letting go

  2. “Them problem” - your team can’t perform to meet expectations.

I lied. These are both "you" problems.


If you struggle to delegate because you don’t want to “dump” your work on your team, you need to reframe what delegating is.


Delegating isn’t a punishment. It’s a reward. Every time you delegate your work, you give your team an opportunity to grow to your level. Someone gave you that opportunity to help you become a manager; you should repay the favor.


If you genuinely can’t trust your team to figure things out with a little bit of your guidance, you may have hired the wrong people. Bummer, I know. But as long as you keep making excuses for them, you’re going to stay stuck in mid-management purgatory.


Who is your best performer? Imagine that person, and now ask yourself: What could we achieve if an EVEY team member were like my top performer?


Mind-blowing right?


Spend time teaching, training, and developing your team, but if those efforts don’t improve performance, let them go.


Tip: Create check-in and feedback structures. Instead of completely ignoring delegated tasks, set up regular check-ins. This ensures progress is on track and provides opportunities for coaching without micromanaging.


You are only as good as your team. If you can’t delegate and trust the work will get done well, you’ll never get out of the weeds.


3. Train Yourself to Think Outside of The Weeds


You probably know that you should spend less time doing and more time thinking and planning. But you keep pushing it off because you don’t actually know what that means.


Maybe you even tried it once. You put time on your calendar to be strategic, and then you spent 30 min looking at a blank page and gave up.


That’s okay. This transition requires a mindset shift that takes time. But you can help your brain get used to it by using a more structured process.


This is what I used to do when I scheduled strategic thinking time:


  1. Review your quarterly goals and how your team is tracking

  2. Identify what’s working and what isn’t and make changes

  3. Identify opportunities for growth and build a proposal

  4. Forecast headcount and budget needs to drive growth

  5. Identify key stakeholders and schedule time with them

You can use my process as a baseline and tweak it. To get a few more ideas, get feedback from your manager, senior leaders, or mentors on how they approach strategic thinking.



4. Take on High-Impact Projects


Lead or join projects that will require you to use your strategic muscle, not just your execution skills.


Once you commit, you’ll have to make the time—no excuses. This will push you to delegate, automate, or eliminate work that is less important than this project.


You’ll get two for the price of one: challenge yourself to think strategically, encourage yourself to delegate, and put yourself out of your comfort zone.


Breaking the cycle is the hardest part of transitioning out of the weeds. Creating constraints by taking on this kind of project will help you take the first step.



Your next steps


Getting out of the weeds is a process that takes time. More often than not, it’s a transition you need to make on your own with little to no guidance.


Use the above strategies to speed up the process and break the cycle of day-to-day operational focus, so you can move toward a more strategic, executive mindset.


I believe in you, and I’m rooting for you.

Maya ❤️

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