Avoiding the painful pitfalls of annual planning.

10 DOs & DON’Ts for growth-stage social ventures

Portrait of Kevin Brown, Co-founder & CEO of Mighty Ally


Fear, doubt, or exhilaration. The words ‘annual planning’ conjure up different emotions for different people this time of year.

Those who fear this business ritual likely envision stale boardrooms, bad PowerPoints, rambling conversations, and no clear decisions. Many who doubt the yearly exercise might think of team-building retreats in the woods, trust falls, shallow promises, and consultant mumbo jumbo focused on feelings instead of action.

Then there are social entrepreneurs (myself included!) who perk up at the thought of annual planning — the most pivotal single moment of the year for leadership teams.

It’s a shame annual planning has fallen out of favor. Because decades ago, planning was widely known to be the number one task for executives. But the demise is understandable. The event is done poorly more often than not. And in today’s rapid change, some leaders view planning as pointless.

Yet, for those of us who have seen it done well (even once), the process becomes a regular cornerstone of the business. It’s a critical chance to drive alignment across the organization — the doing part of your strategic plan. The essential ingredient for building a brand from the inside out. And the opportunity to create a culture that’s more accountable and agile at the same time.

But before buying your sticky sheets and whiteboard markers for annual planning, look at our top 10 DOs and DON’Ts to avoid the painful pitfalls.

“In the face of relentless technological change, disruptive forces in industry after industry, global competition, and so on, planning seems like pointless wishful thinking. And yet, it is clearly essential for any company of any size. Planning twenty-first-century style should be reconceived as agile planning.”


Tip #1


Don’t relegate the planning process to a regularly scheduled meeting. Or make it a side activity for a leader or two. Also, stop now if you think you’re too busy doing the work to meet. That’s like a surgeon saying she has too many operations scheduled to consult with the patient. Meeting, problem solving, and directing are what leaders do. Get used to it.


Do leave the office with the entire leadership team and spend two days off-site without distractions. Yes, that means putting down calls and emails for 48 hours so you can think. Try to even have a little fun — healthy interpersonal dynamics are important as well. And if this feels too overwhelming to manage, consider a facilitator so everyone can focus on the discussion at hand.

Tip #2


Don’t just talk endlessly without a fixed agenda. And don’t try to fix the agenda on the spot. There’s a lot to cover and the time will go fast. Experts have studied effective meeting rhythms, so learn from their best practices.


Do follow a structured format and stick to it. Here’s our recommendation (in PDF form) inspired by the Entrepreneurial Operating System.

Tip #3


Don’t hold punches and let this valuable opportunity pass without being candid with your thoughts. Also, don’t expect you’re the only one with something pent up to say — it’s common for leaders to bottle up things that are bothering them. And don’t wait until the first day of planning to formulate your thoughts — the pre-planning process is paramount as well.


Do collect your individual ideas and input ahead of time. And prepare to practice healthy conflict. The ‘One Thing’ exercise on the agenda can be a great tool to foster radical candor. Trust and conflict form the basis of leadership team health. So talk as a group about this chance to be raw with each other. And if you disagree on something, aim for alignment over unanimity.

Tip #4


Don’t attempt to conduct annual planning without a clear theory of change. If you (and the full team!) don’t know why the organization exists, what exactly it does, and where it’s trying to go in the long run, it’s impossible to determine strategies and tactics for the short term.


Do spend time before planning to ensure you have a theory of change and positioning strategy on paper for all to rally around. Don’t forget to break down your big vision statement into a more tangible 10-year target and 3-year picture. All these elements are your thinking in the strategic plan — the annual plan is the doing.

Tip #5


Don’t try to detail out exact plans and activities for the entire year. Especially don’t try to build a ‘5-year plan’ — social ventures are notorious for complex long-term plans that don’t survive first contact. You’re a growth-stage organization, and one year for you is like 10 years for a large corporation. Things change too quickly to know what the end of next year (or beyond) will bring.


Do plan 3–7 big, single-sentence goals for the year ahead that align with your vision. Along with goals, decide key metrics. Then spend the most time detailing priorities for each quarter (called ‘rocks’) and assign one person to be accountable. People can only focus for 90 days at a time. So that’s as far as you’re planning. Then at the end of Q1, you’ll plan rocks for another 90 days. That’s it.

Tip #6


Don’t let a room full of westerners (often just white men!) make critical decisions for an organization that works in global development. No matter how much we outsiders prioritize proximity, we are not the target audience.


Do embrace diversity. Not just race, gender, age, nationalities, and life experiences. But make sure there’s a voice for your beneficiary at the heart of your brand, even though it’s rare for them to be in the meeting itself.

Tip #7


Don’t walk away from your planning time without clearly documented decisions, next steps, and owners. There’s nothing worse than wasting two good days of conversation by forgetting what you said you would do.


Do make your goals SMART and use a RACI matrix if needed to leave no doubt about who is doing what. Have one person take notes throughout the meeting. Then share with everyone immediately afterward for comments and ratification.

Tip #8


Don’t allow your annual plan to be incongruent with your internal operations and external messaging. Why spend all this time deciding the best path forward unless you’re willing to turn that strategy into action?


Do align your brand internally by creating and sharing a full strategic plan. And amplify your strategy externally by ensuring your marketing communications and messaging support your annual aims.

Tip #9


Don’t think it’s your job as a leadership team to go it alone. Sure, you’re responsible for driving the strategy and plan at the highest level, but the pressure isn’t on you alone to achieve it.


Do make sure departments and teams do their own quarterly planning that ladders up to your company/leadership priorities. Then tell funders, board members, and staff what you’ve decided for the year so they can help.

Tip #10


Don’t let annual planning be the last time you meet as a team. We see it all the time: co-founders and leadership teams will go weeks knee-deep in the programs or products without stopping to talk to each other. That’s a recipe for disaster.


Do ensure your meeting rhythms are consistent: quarterly, weekly, and daily. And use a weekly scorecard to see if you’re on track to reach your annual goals and quarterly rocks. These meetings are the heartbeat of your organization.

“We think that what is necessary today is a strategy that breaks free of static plans to be adaptive and directive, that emphasizes learning and control, and that reclaims the value of strategic thinking for the world that now surrounds us.”


There’s not much time before the calendar flips, so it’s time to get your two-day offsite on the books. But planning the right way in January is better than half-assing it before year-end. So don’t rush if you’re not ready. Just make the commitment today that next year will be different.

Let this next year remove all fear and doubt about annual planning. And maybe for the first time, feel the exhilaration that comes from your brand driving more accountability, agility, and impact at once.

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