Your 2025 plan should border on delusion

You’ve been taught to under-promise and over-deliver – that’s a mistake.

👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

Greg often tells me I need to be more ambitious. It’s hard to take because I feel like my plans are ambitious (or even risky) but now that I manage other department heads, I’m frustrated when I see lack of ambition in their plans.

We’re taught to under-promise and over-deliver. But when you’re presenting to your leaders, executives, and boards, they want more. They want to see ambitious plans that make you uncomfortable but stop just short of delusion.

So going into 2025, here’s our guide for creating plans that have enough ambition to excite an exec, but don’t cross the border into fantasy.

– Taylor

Beating a conservative plan won’t get you promoted

Executives don’t get excited about plans that promise 10% growth or slightly accelerated timelines. They’re likely being pushed to grow the business and create enterprise value faster, so they’re not interested in sure bets that maintain the status quo.

A conservative plan is a buzz kill – execs won’t see you as strategic and they’ll stop listening. But a totally delusional plan also isn’t good – execs (and your team) won’t trust you or have faith in your plans.

You need to find the balance between these two extremes. The best plans, the ones executives get excited about and approve, toe the line of delusion and take one measured step back.

Start by building bottom-up

There are two ways to build a plan – bottom-up and top-down. V1 of your plan should be built bottom-up.

Start by benchmarking how the business is performing today. Identify the levers that drive your plan (leads, conversion rate, ACV, engineering time, NPS, team productivity, etc.) and assume reasonable improvements in these levers in your new plan.

For example, if you’re building the product roadmap, look at how much work your engineers accomplish each week, assume some slight optimizations, and create your roadmap.

This is your base case – it’s a plan you won’t lose sleep over, but it’s not going to get you promoted.

Now, challenge yourself to be more ambitious.

Take your base case and choose 1-3 levers that, if doubled or tripled, would have the highest impact. To do this, build a simple model and play around with each of your inputs, testing what happens if you increase each 2-3X. Push beyond the outcome you know is possible, and imagine an outcome that would unlock substantial growth (or whatever metric matters to you).

You don’t need to know HOW you’ll double or triple those metrics yet. The plan is you committing to figuring that out.

In V1 of our plan at Section, we assumed modest ACV (average contract value) growth from $15K to $25K. But then we explored how the plan would change if we grew different levers by 2-3X, and it’s clear that if we can significantly increase ACV to $50K or $100K, this would transform our business.

It’s the only way we can unlock substantial growth and profitability, so this is the ambitious plan. It demands that we figure out how to grow ACV to $50K next year – it’s not delusional (we don’t assume $100K) but it makes me and Greg uncomfortable. That’s a good thing.

Gut check by building top-down

The other way to get to the most ambitious version of your plan is to work top-down: If you were starting today with no constraints (i.e., if you were a disruptor or new exec leading the team or project), what would you do?

For us at Section, if we were starting today with a team of 5-8 people and $1 million of capital to invest, we’d build an AI workforce transformation business that demanded $50-100K enterprise contracts. We wouldn’t build a company focused solely on AI courses – there’s too much competition and limited differentiation.

It’s harder to imagine this when we’re weighed down by our existing constraints – aka, we have an upskilling business, including non-AI classes, and we’ve traditionally sold to learning and HR leaders.

But thinking like a disruptor with our team and assets would help us shed some of these constraints in our plan.

Here are some questions you can ask yourself to build your top-down plan:

• “If you were starting fresh today with your current knowledge but no legacy commitments, what would you build to create the maximum possible impact for your organization within 3 years?”

• “What adjacent customer problems do you deeply understand that larger competitors are too slow or constrained to solve effectively?”

• “If you could only serve customers willing to pay 10x your current prices, how would you transform your offering to justify that value?”

You can also ask AI to help – ask it to critique your plan (“be my delusional boss”) or assess the plan for the 1-2 levers that would be more transformative.

Your goal should be a plan that’s credible and ambitious. You should feel uncomfortable presenting it … because that’s what it feels like to do anything that hasn’t been proven yet.

Our advice

When you’re more junior, under-promise / over-deliver always works. But as you get more senior, you’ll be rewarded more for occasionally missing an ambitious plan versus always over delivering on a conservative plan.

In 2025, suspend your disbelief. Look at your key levers and see if you can 2 or 3X one of them in the next 12 months. Or think like a startup looking at the same problem for the first time.

And even if you really feel like you need to stay with a more conservative plan, you can at least defend why it’s not more ambitious. Then when your boss starts throwing around crazy ideas – like Greg does (“double ACV”) – you can actually engage in the conversation vs saying “let me go back and think about that.”

If your 2025 plan isn’t making you at least a little uncomfortable, then pause, run this playbook and amp up your ambition.

Have a great week,

Greg & Taylor