Strategic Planning for Company You

Imagine yourself as the CEO of Company You. More than that, you are the entire executive team. You define the vision. You determine the strategy. You set the goals. You manage finances and talents. You allocate resources. You oversee operations. You market and communicate.

In companies, the people with ultimate accountability for those core activities will get together from time to time for a retreat. They work together to take inventory of what has gone well and what hasn’t. They collaborate to envision and plan the future. When done well, it’s a powerful mechanism for creating forward momentum.

In Company You, all of those people are the same person, yourself. You can take the time for an executive retreat as well. It may seem strange to think of yourself as a collective instead of as a single individual, but don’t we always wear many hats, switch from role to role over the course of a year, a quarter — and many times, more like several times a week or day?

Here’s how you can bring all those executive decision-makers together into one room at one time.

First, set aside the time. Don’t put this off as something you will do “maybe someday.” Choose a time when you will go offline with minimal interruptions allowed. It works best if you take this as a dedicated day, blocked out on your calendar, with explicit expectations that you won’t be available for the day-to-day. Don’t try to fit this in on a weekend, holiday, or vacation day. It should be a day uniquely dedicated to this purpose.

Second, just as you would for a high-stakes collaborative meeting among peers, set a timed agenda for yourself specifying what you will do in each hour of your retreat. As you think about the agenda items, approach them as if you were assigning slots to specific people. For example, your CEO kicks things off with a 30-minute visioning exercise. Your COO rounds up activities and resources for 60 minutes. Your CHRO speaks about talent and skills for 30 minutes. Your CMO leads a branding exercise for 45 minutes. You have a 30-minute lunch break. Schedule everything.

Third, go back through your agenda and develop two to three hard-hitting questions or topics for each. I’ve shared a few sample questions below to get started. You know it’s a good question when you don’t immediately have the answer and when asking it makes you feel a bit uncomfortable. It puts you somewhat out on a limb, makes you feel a bit off-balance, maybe even exposed (but still safe, of course — your audience is you).

Fourth, the day before your scheduled day, make sure you can commit to the agenda in full. No, you’re not going to multitask your way through your own executive retreat. No, you can’t just respond to a few emails. No, you won’t be available on Slack. No, people can’t call or text you unless it’s a genuinely critical emergency.

Fifth, for the day of your retreat, decide how you will go through your agenda. You have a few options. Since I’m a writer by nature, I prefer just sitting down to a blank page or blank screen and jotting down my thoughts about the question. Sometimes, I’ll just type down unstructured notes and ideas, but more often, I get better outcomes as if I am answering a serious question from someone I respect — which of course, I am! — and taking the time to think through and compose my answers in a structured manner.

Another option that works for me sometimes is the “walk and talk.” I put on my headset and speak my thoughts into my phone’s voice recording app, either pacing around indoors or taking it outside for a peaceful, quiet walk in the fresh air. Then I put those files through a transcription app so that I have detailed, easily accessible notes.

Finally, give yourself specific, actionable next steps and follow-up tasks. Document them. If you have research or fact-finding to do, break it into discrete tasks and fold them into your plans for the days and weeks ahead. Block out time on your calendar now for a quarterly review where you can reflect on progress, obstacles, and any needed course corrections.

Company You will thrive better with a strategy than in constant reactivity to circumstances. Things will come up, including massively unexpected situations (if 2020 taught us anything), but your strategy sets the contours for action, for change, and for why and how you respond to what happens. Just as with companies and other organizations, Company You needs a reliable mechanism for creating that strategy. This executive retreat approach accomplishes just that.

Sample Questions:

  • What do I want to look back on December 31, 2021? What about December 31, 2024?
  • What are my fundamental beliefs about the world?
  • What changes do I want to bring about in the world around me?
  • What is the unique value that only I can deliver?
  • What do I know and believe that is worth sharing with others?
  • What are the three key messages that communicate who I am to others?
  • What obstacles to my goals do I create?
  • What could I start doing tomorrow to improve how I manage my time and energy?
  • Which skills am I missing?
  • What are my biggest weaknesses, and how can I turn them into strategic advantages?
  • Who are my strategic partners, and how can I make those partnerships more effective?
  • How and when do I dilute my own value?
  • What is the ultimate “why” that drives my desire to succeed and thrive?

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