How to Get Started with Strategic Planning (Without Wasting Everyone’s Time)

Strategic planning isn’t about making a pretty slide deck — it’s how you build a better business.

Without disciplined execution, even the best strategy dies in a binder (SPOTS: Strategic Plan On The Shelf).

You need a planning system, not just a planning session.

A business operating system (EOS, Scaling Up, or Momentum) turns strategy into action.

Bring in a business coach, not just a facilitator — execution lives in the weeks after the session.

90% of Strategic Plans Fail. Here’s Why.

You’ve seen it happen. Two days offsite. Lofty goals. Team building exercises. Everyone leaves pumped. 

Then Monday hits. The binder goes on a shelf. The team chases whatever’s loudest. Six months later, nothing’s changed. 

We call it SPOTS: Strategic Plan On The Shelf. 

The problem isn’t the idea of planning. It’s that most mid-market teams confuse motion with progress. They’re working hard, but not aligned. Busy, not effective. 

Real strategic planning fixes that. It creates clarity around what matters, focuses resources, and gives your team a way to win. 

You’re not doing this to “have a plan.” You’re doing it to build a better business. The plan is just the playbook. 

What Does a Good Strategic Plan Look Like 

You don’t need a 60-page document and motivational posters. You need a working model that connects strategy to execution. 

Start with the big picture — your vision, BHAG, and purpose. Then connect that North Star to what happens every quarter, every week, every day. 

At Incrementa, we use the Momentum Framework — which combines the simplicity of EOS with the strategic depth of Scaling Up: 

Healthy: Right people, strong culture, multiplying leadership 

Smart: Clear vision, winning strategy, strategic agility 

Disciplined: Execution excellence, predictable systems, strong cash flow 

Growing: Sustainable growth, team development, outstanding customer experience 

You anchor strategy to execution with 13-Week Rocks, weekly accountability meetings, and tight feedback loops. 

Strategic planning isn’t about inspiration. It’s about infrastructure. 

Who Should Be Involved in the Strategic Planning Process? 

Planning without your full leadership team is a non-starter. You’ll want to include a diverse group of people such as board members, managers, senior leadership, and even external stakeholders. This can help to ensure a more robust plan to align with your business goals.

The strategic planning process isn’t a think tank exercise. This is the team that owns results. If someone owns a function, they need to be at the table — especially your integrator or operator. You’re not just mapping strategy. You’re building the execution engine to deliver it. 

And unless you’ve got world-class internal facilitation, you need outside help.
 

How to Pick a Strategic Planning Coach vs. Facilitator 

You can’t facilitate and participate at the same time. If you’re trying to run the session and contribute as CEO, you’ll do both poorly. 

That’s where outside support comes in — but not all support is equal. 

Facilitators (like EOS Implementers) show up to run the agenda. They walk you through the tools, keep the group on time, get you to the finish line. That’s valuable for teams with strong internal discipline. 

But if you want to build strategic thinking and execution muscle — not just fill out worksheets — you need more. 

A facilitator shows up for spring training. They teach the plays, run the drills, then leave. See you next camp. 

A coach shows up for spring training AND practices AND games AND the locker room after losses. Rain or shine. With you.

At Incrementa, we are your business coach.  

We show up before the planning session to get deep into the business. We challenge your thinking during the session. We work with your team between quarters to make sure things actually get done. 

We’re not watching from the stands. We’re coaching from the sideline. 

A facilitator runs the session.
A coach builds the capability. 

Learn more: EOS Implementer vs Coach: Which is Right for Your Business? 

When Should You Be Planning and Re-Planning? 

Old-school strategic planning has you create a 1-year (or worse, 3-year) plan with no scheduled reviews. There’s a reason so many strategic plans fail. 

High-performing teams run a different rhythm: 

Annually: Big-picture recalibration (strategy, direction, org model) 

Quarterly: Rock planning and execution reset 

Monthly: Check-in and course correct 

Weekly: Scorecard and commitment review 

If you haven’t reviewed your strategy in 6+ months, you’re not leading — you’re reacting. 

How to Make Strategy Stick: Execution Discipline 

This is where most teams fall apart. 

They plan. They align. They communicate well. And then… execution drifts. 

You need cadence. You need accountability. You need to stop mistaking ideation for execution. 

That’s why execution discipline is baked into the Momentum Framework: 

13-week execution cycles (quarterly planning that works) 

Weekly leadership meetings that actually hold people accountable.

Monthly reviews to course correct.

Quarterly resets that connect strategy to real-world results.

The Rocks don’t live in isolation. They live inside your execution rhythm. 

That’s how strategy becomes culture. 

What Success Actually Looks Like 

Ben runs a fast-growing services company. For years, he wore all the hats: sales, marketing, operations, delivery. They were doubling revenue almost every year, but Ben was drowning. 

Then came the board meeting: “If you want to keep growing and hit $10M+, you need to become a real CEO.” 

That landed hard. What did that even mean? 

We worked together to build his roadmap. He read Made to Thrive, which outlines the real jobs of a CEO. We mapped his functional accountability chart and identified which roles needed to be hired or strengthened. 

First up: a sales leader. Ben realized his greatest strength wasn’t managing pipelines — it was amplifying the brand. He leaned into partnerships, webinars, speaking, and championing culture. 

He started pouring into his leaders — coaching them, challenging them, helping them grow. His calendar changed to reflect strategic work, not firefighting. 

The results? They kept doubling year after year. Employee engagement soared. Turnover dropped. The business got stronger, and Ben earned back his time. 

Today, he’s still growing, still loving it, and leading like a true CEO. 

That’s what happens when you get strategic planning right. 

A Story of SPOTS 

During COVID, I got a call from the Director of Strategy at a company that had decided not to work with us. They’d gone with a traditional planning firm instead — cheaper, faster, easier. 

They had a great offsite. Mission, vision, values. Axe throwing. Long lunches. Zero conflict. Everyone left feeling pumped. 

Six months later? Zero progress. The strategy was beautiful — but dead on the shelf. 

The session created momentum. The business had no way to carry it forward. 

That’s the difference between a feel-good session and a real operating system. One gives you a sugar high. The other builds muscle. 

Ready to Build a Strategic Plan That Actually Works? 

We don’t do planning retreats. We coach teams to execute. 

If you’re ready to stop making plans that die in binders, let’s talk.