Annual Planning: How to Pick the Strategic Bets That Matter | SBI

Short answer: An annual plan with 15 priorities has no priorities. SBI’s planning approach has the CEO and CFO narrow a long list of growth ideas down to three to five strategic bets, scored on time to realization, level of effort and revenue impact. Each bet gets an owner, a budget and a measure. Anything that isn’t funded isn’t a priority, and the plan should say so.

By this point in annual planning, most leadership teams have plenty of ideas. Enter a new segment. Launch a partner program. Rebuild the sales process. Add a product-led motion. Raise prices. Invest in AI.

Each idea has a sponsor and a reasonable case. Together they’re more than the business can execute. That’s when planning stalls, or worse, approves everything.

What is a strategic bet?

A strategic bet is a specific, funded change the business commits to in order to close the gap between what the commercial system can produce today and what the target requires. In the language of Which Number Is the Real Number?, bets turn the math number into the bet number.

A bet isn’t a tactic. “Raise win rate from 19% to 22% in the mid-market segment” is a bet. “Roll out a new discovery framework” is a tactic that supports it. Keeping the two separate stops the plan from turning into a project list.

How do you build the list of possible bets?

SBI’s process splits this into two steps: inventory the bets, then place them.

Inventory the bets. Each executive works with their team on where they could contribute to growth, using the fact base as the starting point. The goal at this stage is breadth. Collect every credible option, from retention programs to pricing changes to new channels.

Place the bets. Leadership scores each option on three criteria:

The CEO and CFO then narrow the list to three to five bets. SBI’s Five Elements to Effective Annual Planning covers this step in more depth.

Why only three to five?

Because execution capacity is the real constraint. Every bet needs management time, enablement, budget and attention from the field. Sales teams can absorb a small number of changes in a year. Past that, nothing changes because everything changes.

Limiting the number also forces the most important conversation in planning: what you’re choosing not to do.

How do you know a bet is real?

Run every proposed bet through five tests before it goes into the plan:

1. It closes a named gap. It moves a specific condition in the plan, such as win rate, retention, pipeline or capacity.
2. It has one owner. A single executive is accountable, not a committee.
3. It’s funded. People and budget are allocated in the plan, not “absorbed.”
4. It has a leading indicator. You’ll know within one or two quarters whether it’s working.
5. It replaces something. The team knows what it will stop doing to make room.

A bet that fails any of these tests is a hope, not a bet.

How do top-down and bottom-up planning meet here?

This is where the two approaches reconcile. Top-down planning sets the target. Bottom-up planning shows what the business can produce today. The gap between them is what the bets must close.

If the three to five best bets don’t close the gap, there are only two honest options: fund more, or change the target. Adding unfunded priorities to make the numbers reconcile is how plans fail quietly.

What does a good bet list look like?

For a business that needs $30M of growth, a strong bet list alongside the core new logo plan might read:

Each line is specific, owned, measurable and tied to the number.

Where should you start?

List every initiative currently in the draft plan. Score each on time to realization, effort and impact. Circle the top five. Then ask the leadership team one question about everything below the line: are we willing to say no?