Scaling Your Product Org Part 2: Planning
In Part 1 of this series, we discussed hiring great product leaders and ICs and adding layers thoughtfully. As you scale up the team, complications arise: new employees won’t intuitively understand how features relate to your long-term vision, initiatives will increasingly compete with each other for resources and customers may become increasingly frustrated by constantly changing priorities. The solution is more explicit planning for the product organization.
To unpack planning, below, I’ll continue my conversation with world-class product leaders Amol Kulkarni, Chief Product and Engineering Officer at Crowdstrike*; Chris Child, Senior Director of Product at Snowflake; James Bayer, SVP R&D at HashiCorp*; Anneka Gupta, Chief Product Officer at Rubrik*; Hannu Valtonen, Co-founder and Chief Product Officer at Aiven*; and Biswaroop Palit, Head of Product at Monte Carlo*.
While annual planning and measuring success can feel inconsistent with the dynamism required to respond quickly to customer feedback, predictability is critical both internally and externally.
“You need a level of consistency and planning to build credibility with customers about what gets delivered or to explain clearly what it was swapped out for,” Amol told me. “Customers are doing their own financial planning because they are mature, so they need visibility into what bets they can take.”
Rather than rolling out rigid annual planning right away, the best practices below will help you calibrate your organizational planning based on the stage of your company.
Start by connecting the dots
“In the early days of Aiven, we were bringing incremental value in a rapid fashion and we had a really small team, but we still kept the North Star of where we wanted to be a few years down the road. Can you connect the dots between the future and now, and systematically drive towards that vision with believable increments of value in between?” – Hannu
During the formative phase of the business, you don’t need a lot of annual planning, especially with one product – you’re busy building what customers need. Focusing on a North Star metric early on is important, but most companies don’t have the data to do so accurately.
Instead, think of your North Star as a description of what your customer’s experience, and the corresponding architecture needed to support it, will be like 2-3 years from now. Work backwards to create chunks of meaningful work, which may span multiple quarters if not years, that drive value for your customers and clarify to the team what they are building and why that product matters. (I emphasize meaningful because people often conflate Sprints with those chunks. I prefer to think of Sprints as a way to determine your team’s productivity to help with planning.)
This North Star should be part of the onboarding experience for all employees and reinforced at all hands so that everyone understands how they fit into the bigger picture. As you design a new feature, confirm it is a step towards that goal. And be sure to test your vision each quarter: Based on what you’ve learned, does it still make sense?
As you start to think about new product lines or significant new features, you’ll need more clarity with the team. You could start more robust annual planning, but instead consider an intermediate step to make the transition easier.
Boulders can bridge the annual planning gap
“Identify the big boulders you want to accomplish next year and whether you are staffed appropriately for them.” – Anneka
Boulders are key product initiatives in the upcoming year that communicate:
Which items are the most impactful for the company
Make clear to each team what to prioritize, especially if there is a conflict
Allow you to align hiring plans with the key results you need for the business
Perhaps most importantly, inform what you will say no to
Unlike the north star, boulders are most effective when time-bound to the upcoming year.
This intermediate stage is a great time to start the bottoms-up identification of critical items affecting the business. They may not create the boulders, but you should still know what your PMs, sales reps and customer success people are hearing. Combine that knowledge with the existential risks that you as a founder or product executive see and write down in 1-2 pages the features and foundations that are most critical for the upcoming year.
Initial attempts to develop boulders often result in 10 or more areas that each seem critical. Don’t fall into this trap. Have the uncomfortable conversations with the rest of the leadership, and with your individual teams, to emphasize that not everything is equally important, and whittle that number down to roughly 5. You’ll find that everyone swimming in the same direction more than compensates for the tension of those conversations, and also weeds out solo artists from team players.
Also, it’s easy to keep these boulders at too high a level. Instead of “Security,” for example, get one level more specific and say, “UBAC for Document Sharing” or “Audit Logs.”
Once you’ve formalized and socialized these boulders, have your teams translate them into commitments one quarter at a time, which ensures you remain responsive to customer feedback and buys you time to iterate on them in advance of a more robust process. Doing so will also make the transition into concrete annual plans much smoother.
Plan From the Top Down
“Each product leader should maintain and communicate an annual plan and a 3- to 5-year vision. A month or two after communicating and explaining the annual plan, we’ll have individual teams conduct bottoms-up planning and then meet somewhere in between with a review and feedback.” – James
You’re now at the point where you have too many teams to count, and priorities are being dropped. Your launches have also gotten much more complex: Marketing needs to build the right content and campaigns, Sales will need enablement on how to sell new products and Finance needs to understand the implications for revenue and margins.
It’s time to start a proper annual planning process.
Annual plans have significantly more granularity than boulders. When done well, they contain commitments by quarter for all teams, launch dates and a schedule of dependencies to ensure the trains run on time.
Your initial instinct to ease this transition may be to start with bottoms-up, democratized brainstorming. While this ensures everyone’s voice is heard, it usually leads to jumbled priorities and a lack of clarity. Instead, do the inverse: Solicit opinions from the organization but decide as a leadership team what matters most.
For example, HashiCorp takes the approach of a “tops-down plan that starts first with R&D leadership,” says James.
Anneka agrees, noting, “Rubrik's annual planning is more tops-down with input from the leads based on historical data of what growth looked like, and what it could look like for this year. The bottoms-up aspect comes from roadmaps built by individual teams on how to accomplish those tops-down objectives.”
There’s no one-size-fits-all format for an effective annual plan. Some plans may be heavily metrics-focused, while others are more akin to boulders with more detail. What matters is that the items drive the business forward and provide extreme clarity to the organization.
But be aware of common mistakes companies make when rolling out formal annual plans:
Insufficient consultation with Sales, Marketing, Customer Success and Finance
Don’t plan in a vacuum; buy-in from other teams is critical to building sustained adoption and driving the business forward
Rolling out plans without corresponding measures of success (covered in our next post)
Leaving insufficient wiggle room
Features always take longer than anyone thinks, so plan to 80% of your available capacity and leave yourself the flexibility to change plans based on what you’ve learned
Becoming overly focused on the short-term
On this last point, it’s critical to include improvements across the core offering, newer initiatives and longer-term bets. And while there is no right way to strike a balance, each of the Product leaders I spoke with voiced similar sentiments:
Anneka focuses on evaluating whether there is “enough fuel in the product to continue expanding for the next 2-3 years” as well as the existential risks for the business over the next 5-10 years
Chris likes to use the Three Horizons framework
Hannu includes 1-2 bigger, long-term items “even when our resources are way less.”
Planning is indispensable
Many of you have heard the famous Eisenhower quote, “I have always found that plans are useless, but planning is indispensable.” He was talking about far more serious endeavors, but the insight also applies to organizations of all sizes: planning enables the team to handle any situation, whether the happy path or a worst-case scenario. It drives clarity, consistency and commitment.
And as you start planning, rather than being disappointed when plans aren’t followed to a T, focus on the impact of your team’s work and whether it drives success for the business.
In my next post, I’ll dive into the art and craft of measuring success.
Takeaways
Start by connecting the dots to your North Star, which is a description of your customer's ideal experience
Boulders can help bridge the gap between no planning and formal annual planning
When starting annual planning, start from the top down before layering in bottoms-up plans
Planning is about driving clarity, consistency and commitment