Start Your 2027 Strategic Planning with These Two Questions [Two on Tuesdays]


Happy Tuesday, Reader!

Last week, I asked you to name the one thing you need to finish this year well. Now let’s talk about what comes next.

As this email lands in your inbox, I’m heading into 2027 strategic planning with one of our client teams. The first question I usually get from leaders new to intentional planning days is this:

What should we do before our planning retreat or offsite days to get the most out of that time?

I love this question because, the truth is, much of the magic of planning begins days or weeks before the session does. By answering two essential questions, teams get far more out of their time together.

The two critical questions to answer are:

  1. What needs to be set up or staged in advance for the whole team to feel safe enough to show up courageous and engaged for planning? ​
    ​
    Different teams and individuals will require different things. For some, it’s as easy as explicit permission to dress casually and to bring special snacks. For others, critical questions or areas of exploration need to be documented and shared in advance, so slower-paced thinkers have space to process their thoughts and ideas prior to planning.
    ​
    More than a few teams need communication ground rules, or to address strained relationships, before anyone walks into the room. Whatever your team needs, addressing it ahead of time protects the time in planning for doing the work of breaking down the year.
    ​
    ​
  2. What do I, as a leader, need to show up courageous and engaged for planning?
    ​
    ​
    Many of my clients who’ve never taken intentional planning space before show up for those first sessions overwhelmed, tired, and anxious after overcrowding their schedules the day before to create space to be “off-grid.” They find it takes most of the first day to come down and reground.
    ​
    Clients who’ve planned with us before know to take that space in advance. Some like to take the day before we begin as a personal clearing day. Others simply make sure to get a good night’s sleep. Whatever you need, it’s essential to give it to yourself because you set the tone for your team’s engagement.

Whether you’re working with Team Realign and me on your 2027 plans, or building in another way, answering these two questions as you begin will make the time you spend far more valuable.

Happy Planning,

Renia C. & Team Realign Consulting

P.S. - Fall Planning Retreats are already full, so we’ve opened up three spots in January for new clients. Book a quick info call to see if a January retreat is right for your team. ​

​
​


Renia Carsillo

Renia (pronounced REE-nah) Carsillo is the founder of Realign Consulting. She believes her superpowers are pattern recognition and activating change. Since 2008, she’s used them to help business founders and executive teams grow both their profit and people-focused impact with joy and ease at the center of the strategy. Renia has worked side by side with impact-driven companies, multinational franchises, and B2B brands in some of the most traditional industries, from industrial manufacturing to government contracting. She and her team have helped over 100 small and mid-sized companies build values-driven, people-first operating models, guided by two proprietary frameworks: Do Better Business™ and Values-Driven Marketing. Her work sits at the intersection of people, systems, and habits. For a business to grow sustainably, these three must constantly realign, because alignment is an ongoing practice.

Read more from Renia Carsillo

Happy Tuesday, Reader! I am writing you from the past. I pen every Two on Tuesdays email you receive from my heart, several weeks in advance of when you receive it. Which means I don't know exactly where things stand as you read this. But, writing from late September, the state of our world feels particularly perilous. So this week, I won’t be sharing any tips or strategies for building your business. Instead, I want to call each of you in. I am here today to ask you to do two very important...

Happy Tuesday, Reader! When times get hard and uncertain, our instinct is often to retreat. We stay online because it feels safer than showing up in person with all our messy humanity on display. We avoid the discomfort of real conversations about how we're actually doing. We keep our heads down and try to push through alone. But here's what I'm seeing after nearly 20 years of working with small businesses through multiple economic crises: The small businesses doing best in this moment of...

E65: Cordelia Proves a 3x James Beard-Nominated Restaurant Can Also Be a Container for Community. When Craig and I visited Cordelia in Cleveland, the last thing I wanted was to take the server up on their offer to talk to the owner. Restaurant owners have long been some of my least favorite people to talk to. But Andrew Watts was a delight, and our whole evening turned into one of the best lessons on the values, beliefs, and community I've had in years. In this episode, I walk through what...