Raw thoughts: annual planning

The part leaders don't talk about

November is here and with that comes 3 things I can always count on:

1. Overeating WAY too much food on Thanksgiving (but I never regret it)

2. A few big sprints to squeeze as much pipeline production as we can before holiday season begins

3. Annual planning for the upcoming year

I already shared some tips around point #2 (linked above). And as for Thanksgiving - my tip there is the exact opposite to that, pace yourself so you can enjoy as many calories as possible over the course of the day 😉

And that leaves me to #3 - annual planning.

I did a two-part series on this last year (part 1 and part 2) that were methodical and retroactive lookbacks after I’d done the work planning for 2025.

So for this year, I thought it’d be fun to show you the messy side of annual planning. Show my work as I’m going through the planning itself. The thoughts + ideas. The questioning of said thoughts + ideas. Trying to figure out what is/isn’t worth pursuing. Handling the inevitable attribution questions that come up internally during planning. Etc.

So without further ado, I give you the first, the messiest, and the most honest step of annual planning: getting started.

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Sponsor: HockeyStack

You just closed a $150k deal. The prospect had their badge scanned at an event, saw 94 ads, got 5 calls/emails from a BDR, and read 3 blog posts. Now the CEO asks: “Who gets credit for this deal?”

But what if I told you that isn’t the question we should be asking?

For years, this was the question I was trying to answer because for years I operated with the “additive” mindset. What happens if we hire 3 more BDRs? What happens if we add $15k more ad spend? And then I would simply map out the anticipated ROI of that effort through our funnel and add it to our current expected outcomes. Hence “additive.”

And then the lightbulb went off. We weren’t successful because of one of those specific channels. We were successful because of how we leveraged the interplay between them.

I’ve had multiple chats with Emir Atli at HockeyStack over the past year about this subject, and this is exactly what they’re helping marketers and GTM leaders solve for.

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Where the heck do I even begin?

If you asked me this question last year, I would’ve said to start by reviewing the previous year (actually, that’s exactly what I said). But that’s not really the first step.

The first step as I’m going through it right now doesn’t even involve data yet. It’s much more of an honest conversation with myself, asking questions like:

• “Do I feel like we’ve accomplished what I set out for our team to achieve this year?”

• “What have I done that’s surprised myself (in a good way) this year?”

• “What have I done that’s not lived up to my own expectations of myself this year?”

• “Am I really the right person to figure out + decide how to drive millions more in pipeline and revenue for our entire company next year?”

  • Note: imposter syndrome never goes away. It runs hand in hand with a growth mindset. Or as Aristotle once said, “The more you know, the more you realize you don’t know.” If you ever come across a leader that says they know exactly what to do or don’t need to learn more, be very wary.

What these 4 questions actually do:

The first question separates activity from achievement. You can be “busy” all year and still miss the mark. In instances like that, it’s time to reflect on where time is being spent that’s not making an impact.

The second question identifies our unfair advantages - the things that worked better than they should have, which usually means we’ve found something worth doubling down on.

The third question forces you to name disappointments + failures while they’re still fresh. What happened? Why did it happen? What can I do about this to make sure I learn from it so it doesn’t happen again?

The fourth question is the fun one - it’s the one that keeps us honest. This question should itch at us every year, but it’s a good thing. It should help us rise to the occasion (or have a real talk with ourselves + our manager).

Which leads me to this year’s raw thoughts

In no specific order, here are some of the various thoughts, ideas, tactics, philosophies, and more that have come up since I received our company’s overarching 2026 plan:

• More isn’t infinite. We have a great demand gen engine here, but I can’t keep throwing money into the engine and expect it to scale at the rate is has the past few years.

• Paid media. Owned media. Earned media. We have a solid grasp on the first, but the latter two are where I need to spend time thinking through as that’s where we’ll balance our efficiencies on the paid side.

• What’s old is new. TV. Print. Radio. Billboards. Webinars. Email. Direct mail. These are all channels that have been used for decades, but the rise of digital + performance marketing pulled us (and our budgets) away from many of these with the allure of cheap CPLs. Unfortunately, cheap is no longer the way to describe most digital channels any longer, and these former “old” mediums have now become much more affordable again as a result.

• Research, relevance, relationships, and recall. I’m betting on this being the formula to win in 2026 and beyond. It’s noisier than ever, so more isn’t the answer to getting more pipeline + revenue. It’s being highly relevant to the prospect. And that’s done by doing proper research on them beforehand. Lucky for us, this is where AI can significantly help creep on see what your prospects have talked about or care about. Use that to develop a relationship with your prospects with the goal of helping them do better in their roles and understanding that 95% of them aren’t in market today for your solution, but will be eventually, so being at the top of their list (aka recall) is what we’re seeking to do.

• Different is better than better. Whether you’re in a crowded category or creating a new one, unless you can statistically prove that the outcome a prospect will get with you is at least 10x better than their incumbent, it’s very hard to beat status quo by saying you’re better. But if you’re fundamentally different, that’s where the dynamics completely change and you get to own the narrative vs. trying to fit into an existing one.

• There are no darlings in marketing. I get bored easily. And that’s exactly why I love marketing. Evolving products. Shifting markets. New technologies. Nothing is ever constant, so there’s always a new dynamic in play. But what that also means is that what’s worked beautifully in the past for me probably won’t within the next year or two. Understand when to kill your darlings or be prepared to fall behind.

• Eisenhower matrix + the high impact/low urgency quadrant. This is one of the most neglected quadrants simply because there’s nothing forcing urgency on the items within it. BUT, those same items are what have the potential to make a HUGE impact to our pipeline/revenue. Make sure time is allocated to the team to work on these as just one of these can be the difference in hitting/missing a future revenue target.

• Know what needs to be worked on or someone else will dictate that for you. You were hired to do a specific job. And you probably have a very unique skillset + experiences that have you as the most qualified person to do that at your company. That means you should know what needs to be done in order to achieve what you’re tasked with (or that you will research, experiment, learn, and find out the best way to do that). Have a plan + allocate your time accordingly. 80% of your time should be dictated by your plan and what you know you need to do. If you aren’t proactive about that, your manager or other team members will happily oblige you and come up with a list of things for you to do, but they probably won’t always be the right thing for you to be doing.

• Attribution by its very definition is divisive. I have a great relationship with our VP of Sales. We know that in order to achieve our revenue target, it means our teams need to work hand in hand. But with annual planning, we need something to understand how + where to apply resources to our teams to drive those results. And this is exactly where the attribution problem loves to poke its little head out. Remember during every conversation that you’re on the same team as each other. You both want the same ultimate result. Don’t let egos or imperfect attribution systems get in the way.

• Shipping is good, but the iteration that comes from the feedback loop is better. Too often we ship something and move onto the next thing. That leaves a ton of untapped opportunity on the table. You don’t need big swing after big swing. Take the big swing, then dial it in and squeeze every last ounce out of it. Make sure this is incorporated into timelines.

• Default optimistic > default skeptical. Goals are set to stretch us and help get to the next level. A goal that’s too easily achieved isn’t really a goal and it’s not helping us grow. Most annual company goals are initially viewed as too hard to achieve, but at the end of the year, you often find yourself very close to it, either just short of it, right on target, or just past it. The one mindset I’ve noticed after working with countless teams relative to ambitious targets is their approach to these goals and if they view them as steep goals, but they’re optimistic about finding a way to achieve it, or if they’re skeptical toward it. As you can probably guess, those who stay optimistic towards it are often the ones who find themselves on the celebratory side of that goal.

• Keep the goal, adapt the plan. As I mentioned earlier, dynamics are constantly shifting in the business world. A plan is made based on the circumstances and variables at the time of planning. When things change enough, don’t be so rigid with your plan that you miss out on better opportunities. There’s always more than one way to reach a destination.

• If your goals + plan don’t scare you a little bit, it’s too conservative. Business is a giant game we’re all playing. It’s strategy. It’s execution. It’s bluffing. It’s going all in. It’s sprinting. It’s resting. It’s killing off a competitor. It’s finding new partners. Yes, it can be incredibly stressful, but at the end of the day, it’s a game we get to play as we seek to improve ourselves, our company, and those around us. 99.999% of us are in jobs that don’t have life or death impact. So take risks, have fun, and aim to surprise yourself.

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See you next Saturday,
Sam