Build the Team Before the Timeline
Strategic planning energizes a lot of leaders.
Vision, goals, outcomes—it feels good to name what’s possible.
The teams I work with genuinely enjoy planning. They care deeply about the mission.
They’re motivated, thoughtful, and driven to perform.
And for those who love structure?
Quarterly milestones and OKRs hit the sweet spot.
Strategic thinkers get to think big. Systems thinkers get to organize and execute.
The Conversation Most Teams Skip
But there’s one critical conversation that often gets left out—
and it’s the very thing that gives strategy staying power:
How will we work together to make this plan happen?
Most planning is forward and outward.
It’s focused on what we’ll do.
What often gets skipped?
The inward-facing dialogue:
What will we need from each other when things get hard?
What does accountability really look like on this team?
How will we recover after missteps—together?
Teaming Isn’t Automatic
Without this layer, execution gets shaky—even among smart, committed people.
And when things wobble, it’s not because the team isn’t trying.
It’s because they haven’t aligned on how to team.
When teaming isn’t intentional, people default to assumptions.
And assumptions don’t build strong teams. Conversations do.
One Simple Way to Start
If you’re planning for a big initiative, try this:
Before finalizing your execution plan, gather your leadership team—or a cross-functional group—and spend real time with the following questions.
These prompts are designed to surface clarity, strengthen trust, and give your team a framework for how to show up for each other.
Top 🔟Team Effectiveness Prompts
When we’re at our best as a team, we notice in each other...
To accomplish our goals, we commit to these teaming norms...
When a mistake or misstep happens, we will...
For us, accountability means...
The qualities of a trustworthy teammate are...
If someone is acting outside our team agreements, we will...
Three things I appreciate about this team are...
We’ll know our teaming practices are working when...
We’ll revisit these questions every ___ weeks.
The dialogue these prompts sparked has been...
Build the Infrastructure for Real Success
When you include conversations like these in your planning process, you’re not just setting goals.
You’re building alignment.
You’re investing in trust.
You’re creating the conditions for shared success.
✨ That’s what makes change possible.
Liv Olson is an executive coach and facilitator specializing in team effectiveness. She partners with financial services leaders and their teams to strengthen clarity, confidence, and collaboration.