So, you want to make a strategy and plan for your engineering organization for the next year. Having done this many times, I want to tell you that (1) I turned my experience into a free planning template for you that you can download below, and (2) we need to start with the most important part:

The goal

Your goal for doing this annual planning is not to create a plan that builds a scenario for any eventualities and that you execute from January 1 to December 31, or whichever time frame your company’s fiscal year covers, waterfall style (they say “don’t go chasing waterfalls” for a reason).

I found annual planning most useful when it’s used as a time to take a few steps back and look at your organization as a whole in the context of your company and with an outlook on the future. This means the goal is to:

1. Know where your company needs to go, i.e. your company’s vision, strategy, goals, and priorities

2. Know where your organization is at by reviewing metrics, staffing, and structure. The goal of this review is for you to develop a very clear idea of the status quo, which will serve as your foundation for >>>

3. Define what your organization needs to do in order to contribute to your company’s goals (that’s your strategy for the next year)

4. Be ready to hit the ground running in the new year; avoid that your annual planning is still ongoing once the year has started. This one is harder to avoid than it sounds. It means knowing very well what your highest priorities are for early in the year; even if other goals aren’t as clear yet, that’s okay, you can still define those later on, but don’t be late on high-priority tasks

5. Take your department along: Share this with your teams/organization and get others excited and motivated. – A note on this: Involve the managers/leaders reporting to you as early as you can. This isn’t just a great learning opportunity for them, but also helps you create alignment early on, incorporate their perspectives, and get buy-in. I have done each step outlined here together with leaders on my team, and highly recommend you do the same. This specific step is about communicating your plan to a larger audience.

6. Review and adjust your plan. Your plan will likely need to change based on internal or external factors. Make room to adjust.

1. Know your company’s goals and needs

• Review your company’s vision, strategy, roadmap, and other planning documents: What are the most important goals for the next year?

• What are your company’s primary needs from your organization? – Currently, that’s often “fast delivery”, “sticking to a smaller budget”. Define what you think these are, and validate with your boss.

2. Assess your organization

You should always have a good sense of the state of your organization, but I highly recommend taking annual planning as an opportunity to dig deeper.

• Delivery, productivity: How well is your organization achieving goals? How efficient are your teams?

• Technical view: How is your software meeting your business needs? Does the organizational structure that you have align with the software architecture that you want?

• Organizational view: How are the structure and systems in your organization serving your teams?

• Team-level view: How well are team structures and makeup working?

• People development and succession planning: Who can you invest in further to help them increase their impact? Are changes coming up that may increase attrition?

Tip: Use this step as a growth opportunity for the managers and technical leaders on your team. Tell them that you’re doing annual planning, and ask them to share with you an assessment of their respective teams/areas. This is a really good opportunity for them to learn about working at a higher level.

3. Define what your organization needs to do to contribute to your company’s goals

Your organizational investments should include the areas you reviewed earlier:

• Delivery, productivity

• Technology

• Organization

• Team-level

• People development and succession planning

Depending on your role and level, now may also be a good time to speak with your peers about their ideas, and see if you can join forces.

You’ll likely end up with a lot of ideas that you realistically won’t fully deliver. I recommend you prioritize everything that will be critical to complete. Keep the other ideas in a backlog. You may prioritize investments e.g. because they provide leverage and are high-value, or they unlock other critical work.

As a result of this work, I would expect you to have a rolling plan for the near-term that’s relatively concrete, and more directional and blurry for the rest of the time. What “near-term” means will depend on your organizational size and stage, but often is 3-6 months.

I recommend again validating this with your boss and other stakeholders such as Product leaders. At this point, you may also need to inform more people, such as an executive team.

4. Get ready to hit the ground running

• Which deliverables are critical early in the year?

• Which investments do you want to prioritize in the areas of delivery, tech, organization, teams, or people?

Plan these as early as possible; these deliverables should be ready for work by the time the year starts.

5. Take your department along

You won’t be able to do all this alone, so take your team(s) along:

5.1 Make your managers aware

This point is essential: Do not roll out plans to your entire organization that your managers aren’t aware of. Blindsiding your managers like this will make them feel unappreciated, and it makes them look like they have no idea what’s going on once their employees ask the inevitable questions that they can’t answer, because they, indeed, have no idea what’s going on. Don’t do this.

Ideally, your managers have already been involved in creating this plan, so it’s not news to them. In any case:

Run a meeting with your managers, or cascade it to all managers through your organization; ask your managers to share any feedback and questions with you – this will help you once you roll it out more broadly.

5.2 Share it with your department and other stakeholders

Use a department meeting to you walk through your plan, or by sharing it in writing (ideally both). Make sure that people who need to know about this plan are invited; in my case, I always extend an invite to customer success and support teams, as well as product partners or platform and infrastructure teams.

Some talking points that I usually use:

• Quick recap of the corporate strategy

• The engineering vision (what does our department look like by [insert appropriate date here])

• The engineering strategy (what are we doing, and why)

• Our goals and priorities, and why we will focus on those (this is where you’re connecting to your strategy again)

• Investments in delivery, tech, organization, teams, and people – you can keep this part high-level for now. Most critical is that people get a first sense of what’s to come and what’s important to you and the organization as a whole.

• Be ready that people will ask “what does this mean for me?”. If you can, speak to this part as much as possible. If your organization is quite large, it helps to give managers a heads-up (see 5.1) and tell employees to pass questions about their team to their manager.

5.3 Rinse and repeat

This, too, is really important: Managers never talk about strategy enough.

You and every manager in your department need to talk about strategy more often than you think. Employees don’t understand strategy as well as executives think, and often struggle with understanding what it means for their specific team.

Tip: Schedule a recurring reminder in your calendar to talk about strategy.The best time is every two weeks before your staff and department meetings.

6. Review and adjust your strategy

Once you go into the year, you should have a set of metrics that tell you how you’re doing in accomplishing your plan. Review your strategy at least quarterly, and adjust as needed. I usually have a reminder set for myself – 4 weeks before the start of the new quarter, I’ll run a review together with my teams, so we’re ready to tweak the plan as needed.

And remember: Keep talking about strategy.
If you’re tired of saying it, assume that 70% of people have heard it.