​​3 Conversations Every Leadership Team Should Have Before Their Next Strategic Planning Offsite

When we hear the word planning, we usually think of solutions, timelines, and next steps. You know, the fun stuff! But what about the pre-work? Reflection and assessment are critical steps before looking ahead to define strategic direction. If you want to build a foundation for real change (and who doesn't), I recommend having three important conversations at the leadership level before your full-team gathering (I’m including my favorite questions that you can use to guide your own conversations below!). 

This doesn’t mean spending endless time building a complete picture of all that’s happened leading up to now, but it does mean pausing and having a conversation to get grounded in reality. 

I’ve included a list of questions that I always cover with clients on the precipice of a strategic planning initiative. Having these conversations will encourage you and your peers to get candid and create alignment so you have a greater likelihood of successfully moving forward together.

3 Conversations and Questions to Prep for Your Next Strategic Session

Conversation 1: What’s motivating us to gather now? Typically a past or anticipated future event is the impetus for convening a group. Start there, and dig into the specifics. 

Past events might be: 

• We’ve had leadership changes, turnover, new hires 

• We’ve had some dysfunction 

• Change is slow, people aren’t aligned 

For past events, consider the following questions but don’t let the conversation devolve into venting or unproductive rehashing: 

• What did we learn? 

• Were there key insights or events that can help us?

• What do we wish had been different? 

Future anticipations might include: 

• We’ve got a launch deadline

• We’re planning for funding and leaders need to understand the potential of new initiatives or ideas

• We’re hoping to scale in a more meaningful way

• We’re anticipating the sale of this business 

For future events, be candid about why it matters: 

• What is important about the event?

• What do we need to have prepared?

• Who will be there and what will they care about or want to know?

• What do we want to say happened after the event? 

Conversation 2: What are you hoping to achieve and what’s your ideal future state? 

To make it tangible, get specific and ask questions like: 

• Ideally, what can we say is true 6 months after we’ve completed this work together?

• Best case scenario, what are we telling our boss, board, or investors after we’re done? 

• If we were wildly successful three years from now, what would be different?

• What do we want customers or partners to say about us?

Conversation 3: When it comes to the workshop, offsite, or retreat, what matters? 

• What do you want people to walk out of the room knowing or feeling?

• Are there tensions or disagreements that need to be addressed directly before the offsite?

• Are there leaders who need to buy in or support the future who aren’t currently included in this work? What’s the best way to engage them? 

• What level of candor and participation do we want in the room?

When I’m partnering with clients on this pre-work, I typically create a summary of key points, big events, or themes that stand out after these questions are answered. It helps me design the right program and agendas to take teams forward from current reality. 

You might do something similar, but even if you don’t go full facilitator-mode like I do, you should still have enough insight to support more honest dialogue, stronger alignment, and better decisions.

Great offsites start before you gather. And they’re shaped by the conversations you’re willing to have (remember, clear is kind, as Brene Brown says). 

When teams enter the room grounded in context, clarity, and candor, they can spend less time circling the drain on preventable issues and more time building momentum together.

If you want help with strategic alignment or navigating AI integration, let’s connect. I create collaborative environments where teams can identify friction points, test tools, prototype workflows, and build better ways of working—together.