Trouble Getting Out of the Weeds? Ask Madeleine

Dear Madeleine,

I was recently promoted to a VP role in my company. It was a bit of a surprise as I thought my boss would never leave—but he did, quite suddenly. I have been in the role now for about five months.

My new boss keeps telling me I need to “get out of the weeds” and be more strategic. I have no idea what that means. I am still doing my old job while now also supervising the work of all my peers. I am at my wits’ end with the workload. The meetings alone are killing me.

My biggest issue is that I am most comfortable simply getting things done—making my list of tasks and systematically checking them off. I suspect that isn’t particularly strategic.

Any thoughts on this would be appreciated.

How to Get Out of the Weeds


Dear How to Get Out of the Weeds,

I can appreciate your overwhelm and confusion. The transition you are going through is one of the hardest, in my opinion, because everything you have done in the past that has made you successful is now getting in your way.

It is very common among people who are great at execution to be at sea with how abstract and unproductive “strategic” activity can feel. It is a shift in mindset that very few people recognize and even fewer are able explain or help with. It sounds like your boss might be one of those folks who expects you to just figure things out on your own.

I recommend a couple of do-nows—things you can do right now that will set you up for success in the near future.

  • Identify someone in the organization that you respect and ask them to mentor you. Tell them you specifically need help to figure out how to be more strategic.
  • Ask your boss what five things they need to see from you that will give them confidence that you can be more strategic and that you can do the job the way they want it done.
  • Replace yourself: find someone who can do the job you were doing before. Either promote from within or request to hire from outside the organization. Nobody can be successful doing two full-time jobs.

Once you have done all of the above, or have them in process, you can turn your attention to what it means to be strategic.

This issue has come up so much with my coaching clients that I have developed a list of things a strategic leader does, gleaned from my experience and from reading books and articles. There are a million books on this topic and even more opinions, so remember this is just my take on it. Maybe use this list with your boss to see what they agree with and what they think might be missing or not quite right. That will at least get you two on the same page.

What does it mean to be a strategic leader?

See the big picture:

  • Anticipate what is coming. Note and develop plans to navigate the unknown.
  • Get the big ideas right.
  • Stay aligned with reality while entertaining innovative ideas.
  • Use big ideas to set direction while considering potential contingency plans.
  • Craft the short-term and long-term objectives that will move people in the right direction.
  • Communicate about objectives and direction clearly and repeatedly. Use storytelling and share inspiring wins widely.

Translate the abstract into the concrete:

  • Help design tactics to achieve objectives, especially those that require cross-functional cooperation.
  • Oversee implementation and execution of tactics—create dashboards of the most relevant data to create transparency, visibility, and accountability.
  • Track analytics—interpret data to formulate meaning found in analysis.
  • Refine big ideas, direction and objectives, and tactical approaches as activity surfaces new information.

See all, know all, intervene judiciously:

  • Re-direct to maintain focus.
  • Measure and evaluate performance.
  • Track successes and breakdowns—help tackle hiccups in processes and systems.
  • Support solving of complex entrenched problems.
  • Make sure people feel noticed, seen, and heard.
  • Keep your ear to the ground to get advance notice of potential problems and to surface time-wasters—policies that aren’t producing intended results. Anticipate.

Focus on the future:

  • Create multiple paths for generating and testing ideas.
  • Create an environment of learning and innovation.
  • Develop opportunities for high potential performers.

Master political agility:

  • Cultivate relationships incessantly.
  • Challenge the status quo without provoking outrage.
  • Be masterful at shuttle diplomacy—conducting negotiations, especially between parties at odds with each other, but also parties who can’t see how their goals can be aligned.

As you can see, a lot of these activities involve thinking or relationship building, which can feel like anything but work. And to be fair, it isn’t work as you have known it. But it is work—it is strategic work and someone needs to do it. You can expect this transition to take some time and a lot of getting used to. Don’t be too hard on yourself. Give yourself some grace. As long as your boss is getting what they need from you, you will be okay.

Good luck.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

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