How to Run an Annual Planning Process That Doesn’t Fall Apart by March

  • Startup

TL;DR:

  • Don’t just set goals. Build a system.
  • Anchor your annual plan in your mission.
  • Prioritize like you mean it.
  • Set clear goals, fund them responsibly, and review them often.
  • Keep it simple. Communicate constantly.

A plan is only as good as your discipline to stick with it—and adapt when needed.

Annual Planning That Actually Works

Let’s be honest: Most “annual planning” processes are just… wishlists.

Every team throws in what they want. Finance builds a budget no one reads. And three months later, people are chasing things that weren’t even on the original plan.

If that sounds familiar, you’re not alone. But there’s a better way.

Real annual planning should be structured, strategic, and actually useful. It should tell everyone:

  • Why we exist
  • What we’re trying to achieve
  • What matters most right now
  • And how we’re going to measure success

That’s a lot. But it’s not magic. It just takes a clear sequence.

Start With the Mission, Not the Metrics

Before anyone throws out OKRs or stretch goals, start with the big stuff:

  • Why do we exist?
  • What are we building toward?
  • What do we believe?

Your founding documents (mission, values, long-term vision, team charters) should anchor everything else. If you don’t have these written down, start there. If you do, reread them. They’re your compass.

Make Strategy Real by Saying “No”

Annual planning isn’t about doing everything. It’s about choosing what matters. That means prioritizing—ruthlessly.

A good strategy should hurt a little. If nothing’s being left behind, you haven’t made a real choice.

Translate those priorities into tangible outcomes:

  • What do we need to accomplish this year?
  • What’s worth investing time, money, and people into?

Set Clear, Measurable Goals (and Keep the List Short)

Think:

  • “Launch X by Q2”
  • “Grow revenue by 20%”

Not:

  • “Enhance customer happiness through innovative excellence”

Pick 3–5 company-level goals max. Tie each to metrics. Then cascade goals to teams and individuals using a framework like OKRs or SMART goals.

If someone can’t explain how their work connects to a company goal, the plan isn’t working.

Allocate Resources Like You Mean It

Don’t let planning stop at the goals. Tie it to budgets and headcount.

  • What are we funding?
  • Where are we hiring?
  • Where are we holding the line?

Resource planning should be objective, not political. Use ratios and benchmarks (like revenue per head) to guide decisions. And build in flexibility. Plans shift—your model should too.

Set the Cadence Before the Clock Starts

Planning isn’t a one-time event. Build an operating rhythm:

  • Annual kickoff
  • Quarterly reviews
  • Monthly check-ins
  • Weekly team syncs

Decide now how often you’ll review goals, share progress, and make adjustments. Otherwise, goals will collect dust.

Communicate the Hell Out of It

People can’t execute on a plan they don’t understand. Spell it out—in plain English:

  • What’s the mission?
  • What are this year’s top priorities?
  • How do you contribute?

Share it at all-hands. Put it in onboarding. Tie it to performance reviews. If it’s important, it should be visible.

Review, Refine, Repeat

Things change. Plans should too.

Build in review moments—quarterly, mid-year, end-of-year. Use them to recalibrate, reallocate, or refocus.

Be transparent about why goals change. People will respect you more for it.