Working with leadership to plan for a successful new year

With knowledge of business context, an understanding of leadership’s priorities, and a strong roadmap, you can make the most of your annual planning process.

As engineering leaders, it feels comforting to know that we have so many parts of our jobs down to a science: daily standups, scripts for 1:1s, hiring rubrics, and more. However, annual planning – the process by which we define what we’re doing and how we’re going to staff it – can feel daunting.

It’s an ambiguous part of the year that can take on so many shapes, and often varies greatly across companies. Having the right tactics on hand will help you get the most out of annual planning, no matter what the process looks like.

What is annual planning?

Annual planning is largely a budget exercise that determines how much the company thinks they’re going to spend on things like headcount, technology, and marketing, alongside how much revenue they’re likely going to make. While team roadmaps are incredibly important, they are usually an input to the process, rather than a direct output. The roadmaps, along with technical complexity, product research, and the makeup of your staff will help senior leadership create a plan that is financially viable for the business to sustain and grow in the following years.

The amount of direct participation that you have in annual planning depends on your role within the organization. For senior leadership, this might be a full-time job. Conversely,  frontline managers might have an awareness that it’s going on, but are ultimately more focused on the day-to-day operations of their teams.

Either way, you have a part to play and you should take the time to understand what that is. This understanding gives you more agency to set your teams up for success in the coming year.

Understanding your levers

Instead of feeling like the process is happening to you, investigate what levers you have to pull on in order to make it work for you.

If your company has a well-established annual planning process, reading up on that along with having a deep understanding of core business metrics and goals is a great place to start. From there, talk to your manager and senior leadership regularly about planning in order to get more insight into the discussions they’re having and what their top priorities are. This is often a hectic time of year for managers of managers, so information asymmetry can increase; use 1:1s to close that gap, keeping an eye out for ways that you can bolster your team.

Here are some questions to ask:

• What’s the overall timeline of the process? 
• Are there any important milestones that can be shared? Who are the decision-makers at each stage?
• Will there be an opportunity to grow my team? What would you need from me to advocate for that growth?
• Do you expect my team’s goals to be similar to this past year? What’s your level of confidence in the work we’ve been doing?
• Are we considering migrating any parts of our stack? Is it a good time to investigate third-party tooling?
• How can I support you in this process? What do you need from me?

Doing this investigation should give you a framework that you can plug in to create the best outcome for your team. Usually, this boils down to staffing, scope of work, and technology.

Making planning work for you

This is the fun part. Armed with all the information you need, take the time to imagine what your team would ideally achieve in the next year. Now imagine what that would look like with one more engineer, or even ten. Think about whether achieving your team goals means taking on the same projects or shifting to something new. Will that require the same technologies? Perhaps there is also technical debt to pay down.

Work with your partners and your team to dream big. Doing a retro on the topic can be an illuminating way to get this information. Engineers tend to have a lot of forward-looking insights that they’ve been keeping to themselves.

Once you have that vision, the next step is to translate it into the planning framework that you identified before. Reconciling your vision within this framework will give leadership the input that they need to move forward. A good practice is to consolidate the vision in a document that also answers fundamental questions around planning.

• If you want more headcount, what data can you show to justify that your team’s impact would increase proportionally?
• Is your team’s scope of work still the right area of investment for your team? Does it still align with broader business goals? If you’re proposing a pivot, how big is the pool of opportunity for the business as a result?
• If you’re proposing big technology investments, could you model out the cost implications and when the team would see a return?
• What will happen if your team doesn’t get any additional support?

Delivering this information in a digestible way will make it much easier for leadership to evaluate your situation and partner with you. They will likely be doing this process with many teams, so contextualizing and justifying requests upfront will provide a better starting point for negotiations. 

Other considerations

Especially in the current tech climate, where a lack of company growth can be startling to employees, planning can also be a source of anxiety. Take care of your team by asking the right questions to leadership and passing on relevant information that will provide reassurance. 

You may go through this process and get exactly what you want, but you may get nothing at all. With hiring freezes becoming the norm in tech companies right now, it’s also imperative to plan as if you will have no increased budget or headcount. Preparing your team for multiple scenarios in advance builds trust, and signals best and worst cases to senior leadership.

On the positive side, planning is also an opportunity for employee growth and recentering on your customer’s core needs. It’s a great time to connect reports who are looking for ways to stretch themselves with new roles or tracks of work that arise.