Top leaders share their proven strategies for building predictable plans in unstable markets.
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There’s the regular holiday season… and then there’s annual planning season. Not quite the same, right? 


But maybe this year’s annual planning can be a little less spooky and a little more jolly, thanks to strategies from the experts, a brand-new live strategy course, and some pretty cool features in Databox that let you pull it all together. 


Let’s get into it!

In this edition:

  • Annual Planning? Get the Strategies Top Leaders Use
  • New Report! The State of Annual Planning & Modeling
  • Predictable Scale Methodology & Online Training
  • ICYMI: OKRs and Forecast Modeling Launched!
  • This Week’s Silo-Smashing GTM Reads

🎥  Annual Planning? Get the Strategies Top Leaders Use to Build Predictable Plans in Unstable Markets

When it comes to annual planning, most companies try to do too much – and end up achieving far too little. One in three businesses are running more than 21 major initiatives at once. According to the panelists of our recent webinar, that’s not strategy – that’s chaos.

 

In the Annual Planning & Forecast Modeling Secrets webinar, Dr. V. Boykin led a candid, practical conversation with four powerhouse operators:

  • Pete Caputa, CEO at Databox
  • Jen Spencer, Chief Growth Officer at Booth
  • Doug Davidoff, CEO at Lift Enablement
  • Jeetu Mahtani, CRO at ShipBob

Focus Wins. Complexity Kills.

 

Pete Caputa didn’t pull punches: “Most scaled operators will tell you that companies should only be running 3-5 major cross-functional initiatives. Yet our survey showed many teams are juggling 20+ at once. “You can’t do everything. The essence of strategy is deciding what you’re not going to do.”

 

Jen Spencer added, “We all know better. But we keep piling more on. It’s like Coco Chanel said – except instead of removing one accessory, we add three more priorities.”

 

Plan Like a Forecaster, Not a Dreamer

 

Board pressure is real. But caving to aggressive top-down goals without cost modeling is where so many plans go wrong. Jen put it bluntly: “Yes, we can hit that number. But what are we going to stop doing to get there?”


Pete echoed the need for modeling: “Companies often stack risky bets and assume they’ll all work. But they don’t model what happens if just one fails – and that’s where the plan falls apart.”


Pete added, “You must use data to model your future performance. What happens if you increase spend or improve efficiency by 20%? Model that. Ground your planning in reality.”

 

Trust, Transparency, and Strategy Go Hand-in-Hand

 

Jeetu outlined the need for shared assumptions before the plan is built: “Each function often operates on its own logic. You need to align everyone early, then identify what matters most – three to five key initiatives.”

 

Doug shared a simple but powerful suggestion: ask your team to describe your strategy in 300 words or less. “You’ll be shocked at the misalignment,” he said. “Good strategy creates clarity. Great strategy creates clarity for everyone.”

 

Jen drove home the importance of involving frontline teams earlier and having consistent language and definitions. “One team must own the data dictionary. Otherwise, you’re debating semantics instead of solving problems.”

 

Stop Annual Planning from Being a One-Time Event

 

Doug pointed out a core flaw in most companies’ approach: “We plan by event, not by process. Planning should be ongoing, not a once-a-year offsite. And we need to present not just the plan, but the hypothesis behind it.

 

“If your plan is just numbers, it’s not a plan. You need to ask: What are our opportunities? Risks? What do we do if we’re wrong?”

 

Your Plan Should Work Like a GPS

 

The group aligned on a practical approach to execution:

  • Start with 3–5 objectives
  • Use OKRs and shared dashboards to align teams
  • Review and adjust quarterly using real-time data

Jen described Booth’s approach: “We treat our annual plan like a GPS. It keeps us moving forward, but we can reroute as needed. It forces prioritization.”

 

Pete reinforced the need for rhythm: “If you want to grow, you must innovate. We don’t just need dashboards. We need feedback loops.”

 

Don’t Just Hit Targets: Build a Smarter System

 

The final takeaway? Hitting your number is not the same as building a high-performing system.

 

“You can squeeze harder and get more juice – but is the juice worth the squeeze?” — Doug Davidoff

 

 “True scale is growing revenue and margin at the same time.” — Pete Caputa

 

 “Your North Star might be growth. But you can’t get there by burning people out.” — Jen Spencer

 

Whether you're rethinking this year’s plan or already forecasting for next, this discussion offered a refreshing perspective: slow down to model, align, and clarify – then execute with confidence.

 

🎧 Get the webinar recording

📊 New Report! The State of Annual Planning & Modeling

New Research Report (1)

We unveiled the key findings in last week’s webinar, but now the full report is available for everyone!  


The good news? 85% of leaders say they hit or exceeded revenue targets last year.

 

But as '26 planning kicks off, the data tells a more complicated story:

  • 25% cite poor data hygiene as a top challenge
  • Nearly 1/3 are running 20+ major initiatives all at once (while “doing too many things” emerged as a top challenge in executing the plan)
  • Less than 1/2 share their full financial models across the org
  • Leadership misalignment is an extremely common challenge

The TL;DR? Plans look strong on paper, but often crack under real-life pressure.

 

Get the full report to learn the biggest mistakes – and opportunities in annual planning and forecast modeling.

Get the report

📝 “Predictable Scale” Methodology & Online Training

What separates predictable growth from lucky wins? 

 

Building a predictable plan that starts with strategy and builds from there. 

 

The SPEARS framework (for Strategize, Plan, Execute, Adjust, Repeat, Scale) walks executives and other leaders involved in planning through exactly how to build a solid strategy and carry through to execution. 

 

Authored by Databox CEO and former HubSpot exec Pete Caputa, the course is now live and entirely free online. 

 

If you’re involved in annual planning, now’s the perfect time to watch the course (and share with your team!). 

 

📊 Start the Free Course

 

We’ve also built an assessment to help leaders and agencies determine their maturity against the SPEARS predictable scale framework.

 

Want the free assessment? Just reply to this email.

🚀 ICYMI: OKRs and Forecast Modeling Launched!

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We don’t usually promote the Databox product too hard in this newsletter… but this latest launch is too good to not share. 

 

We just launched OKRs and Forecast Modeling in Databox – now you can truly develop your strategy, define clear objectives, connect those objectives to goals, and track your results: all in one place. 

 

→ Try it now (or learn more here)

🤝 This week’s silo-smashing GTM reads

Share with a colleague and tear down those walls!

  • Strategic and Annual Planning in Volatile Times: What Every CEO Should Know (BCG)
  • Mastering Leadership Team Alignment: A Core Challenge for Leaders (Bright Arrow)
  • OKRs: The ultimate guide (Atlassian)

🤝 How’d we do?


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