Annual Planning’s Hidden Traps: Why Most Strategic Sessions Fail (And How to Fix Them)

The fact is, one of the biggest things is to not set it up—not warm people’s thinking up effectively.

Your annual planning session reveals everything about your organization’s strategic maturity. Done well, it becomes a catalyst for breakthrough thinking and accelerated execution. Done poorly, it’s an expensive way to demotivate your best people.

The Neurology Trap

You don’t want people to just walk in cold- you don’t want to set the dates and say, “We’re going to be reviewing the strategy. Boom.” These are big questions. So you don’t want people walking in cold—this is not setting you up for success. The goal might be to review performance and recast the next 12-month plan- make sure you trigger the neurology of participants ahead of any team session. 

The PowerPoint Trap

I would say no PowerPoints. PowerPoints for pre-read, if that’s going to be helpful. But no PowerPoints during the session, with two exceptions: one is to show the financials, or the likes of culture results where you’re looking at results or numbers. There should be some sort of visual, but not one that is filled with a whole lot of words.

The benefit is that everyone is looking up and engaging, not being talked at through slides. Real conversation is enabled.

The Agenda Sequence Trap

The order of the agenda is critical. I’ve seen sessions run by very senior people from major consulting firms where they basically set the agenda based on availability at particular times. I am reminded of a particularly wasteful session- they had deep-dive specific topics initially, then went back to look at some completely tangential thing. After lunch, they looked at results. Then they went back into the external environment. It was all over the shop.

If you’re wanting to re-establish or think through what your strategic pillars are, you have to set the right agenda sequence:

1. What happened in our last performance period?
2. What’s going on in the external environment?
3. Confirm the competitive strategy, considering how it might be strengthened.
4. How does that all come together, and what opportunities are genuinely thrown up?
5. What are the performance goals for the next performance period?
6. Where do we want to now place our focus to achieve these? What might we need to modify or add?
7. What does that mean for the way we show up and the way we do things? Where do we need to do things differently?
   

The Facilitation Trap

Internal facilitation is problematic because there’s always a sense of bias. And if the leader does it, there’s a distortion. The leader needs to be a key voice—they need their voice strongly in the conversations because they’re presumably one of the most valuable and informed members of the team. If they are also facilitating, then that is not helpful- there views can dominate and others step back and let the leader have ‘the floor’ thus limiting contribution and new thinking.

You need the independence, the neutrality. And that person needs to have an understanding of strategy, not just be a facilitator. They need to understand what competitive strategy is, and they need to understand human dynamics, culture change, leadership, behavioral change. The mix is crucial in terms of stimulating the right conversations and best paths to the next round of success. For more on this, read our post, “The Dangerous Disconnect: Why Separating ‘People’ from ‘Strategy’ Is Killing Your Performance”.

The Follow-Up Trap

One of the biggest reasons sessions fail is the lack of follow-up. You want to be intentional about what you’re igniting in the room. You are igniting a continuation of shared understanding and ownership. You want to establish a level of speed or pace during that session so that the conversations and effort continue with strong momentum.

You have to start setting the follow up during the session so you hit the ground running the day after, and then the next day, that week, the next week. You have to keep your foot on the accelerator, otherwise you will absolutely go back to where you were before you went in for two or more days. Without the right disciplines to maintain the focus and momentum the session will inevitably be a one-hit wonder.

It’s usually takes about four months of really focused commitment to keep the rhythm of embedding and execution, and it usually involves a combination of an internal and external support unless there is a very skilled transformation or program execution office.

The Breakthrough Thinking Secret

You want to use these sessions as a means of role-modeling good ways to run meetings, good ways to have generative dialogue. Good ways to create what I call “the sediments of conversation” that actually support breakthrough thinking.

Breakthrough thinking is purely a result of having the right series of conversations with the right stimulation of people’s ‘brainpower’ and done without constraining forces. You just let things bubble up and out pops a new perspective because the dots, the stars, the patterns connect and align within the dynamic system of internal and external forces.

The Bottom Line

Annual planning should deepen shared understanding and ignite a level of ownership that accelerates execution all year long. When you get the setup, sequence, and follow-through right, you don’t just create a plan—you create momentum- a rhythm of powerful and aligned execution. If you need help with this, explore our offerings.

Is your planning process creating breakthrough thinking or just checking boxes?