The Ultimate Annual Planning Guide for Startups

How to run your OKR Process

Module philosophy & overview

OKRs or Objectives & Key Results are unique to every company. This framework is meant to be adapted to best fit your company’s culture and business practices. With a bit of preparation, you can align your executive team to iterate quarter by quarter, establishing an effective process specifically optimized for your business.

This module is intended to help you implement the best practices for building every component of the OKR operating system: Annual Objectives, Key Results, and Initiatives. An annualized roadmap will guide your use of these three components in your planning.

We’ve designed the following slides as a guide to build your system, and M13 is here to help along the way.

​

How do I use this guide?

​

This guide will take you through the four-part process of creating OKRs, and help you establish a cadence to run the process throughout the year.

• Read through the presentation, and note the follow-along instructions on slides.
• Reach out to your primary contact at M13 for a project kick-off.

+

Create a copy�of this presentation, and change the title to your company name.

+

Create a copy�of the OKR framework worksheet, �and change the title to your company name.

OKR module framework

Phase One

Phase Two

Phase Three

1

OKR �framework

Annual Objectives, Initiatives & Key Results

identify OKR process ownership and

best practices.

3

Annualized Roadmap

​

Establish roadmap of all key Initiatives and projects by quarter.

Exhaustive list that can iterate throughout the year.

​

5

Rinse & repeat cadence

​

Quarterly process going forward, including:

Monthly status check-ins

(red/yellow/green).

Quarterly planning for ongoing quarters

​

4

Quarterly planning

​

Develop your quarterly planning process and inputs needed.

Repeatable framework and touchpoints

​

2

Annual �Objectives

North Stars set by the executive team.

Objectives that are company and time specific

basis of OKR framework.

​

OKR framework & Annual Objectives

In this section, we will discuss the key components of the OKR framework and best practices for annual planning. Establishing your company’s Annual Objectives is the foundation of the OKR framework, and is essential for a successful OKR operating system.

​

​

*For recommended OKR tools/platforms, see addendum

+

• Your copy of the OKR Framework Worksheet
• Tab 1: Case Study: Annual Objectives
• Tab 2: YOUR TURN: Annual Objectives

​

Materials + Information needed:

Your Company’s

• Annual Objectives

​

What is the OKR framework?

6

We have found that the optimal way to set up your company’s OKRs is to use the following framework:

• Annual Objectives: Macro-level goals that cover all key aspects of the business and strategic priorities for the year
• Annualized Roadmap: An outline of all of the key milestones & projects for the full year
• Quarterly Key Results: Quantitative measures of success with clear outcome expectations
• Quarterly Initiatives: Priority tasks and projects that touch each area of the business and help you achieve your Key Results

OKR framework introduction

Who owns and runs the OKR process?

7

Establishing a point person to own the the OKR process from start to finish is key to its success:

• Identify an owner for the OKR Process on your team
• This person should interact closely with the Leadership team and have a broad understanding of the business
• Possible examples include Operations Program Managers or Chiefs �of Staff
• They will be responsible for keeping the OKR planning process on track and monitoring the OKRs on a monthly, quarterly and annual basis

OKR Process ownership

​

​

What are Annual Objectives?

Annual Objectives are macro-level goals that cover all key aspects of the business and strategic priorities for the year. These will not change throughout the year and should indicate your KPIs to your team.

Annual Objectives introduction

​

​

Best Practices:

• We recommend orienting your business around 4-5 Annual Objectives for�each year
• Set Objectives that are both company and time specific
• Make sure your Annual Objectives have strategic direction and are not too generic or broad
• Annual Objectives should tell a clear story of what your company’s key priorities are for the year

​

Example of a great Annual Objective: Drive Operational Excellence and Employee Retention

​

Watch Outs:

• Avoid Objectives that simply state the work plan of a function of the business. That approach hinders collaboration and can cause team members to lose focus on the ultimate strategy, instead drawing attention to operational tasks
• Be careful to not make your Objectives simply a statement of KPI objectives or key metrics (e.g. Increase revenue by X%)

​

​

Example of a poor Annual Objective: Build a Best in Class Product Solution

​

What do you build Annual Objectives around?

Annual Objectives introduction

​

​

Demand �Demand in the market is growing

Launch two new products to meet market demand

Engagement �Users are highly �engaged.

Increase DAU by 50% YOY

Business economics The business economics are…

Diversify and grow revenue streams

Operational Excellence�The business is operating well.

Scale Systems and headcount to accommodate our growth

Service Quality �The service quality is…

​

Establish our Brand as the Best Value For Cost in the Market

Product x Market Fit�You’ve reached product x market fit

Achieve and Maintain an NPS score of 80 or above

example

Use the Case Study: Annual Objectives tab in the follow-along worksheet.

Then, on the YOUR TURN: Annual Objectives tab, work with your team to set 4-5 Annual Objectives.

Your Annual Objectives guide

• Your copy of the OKR framework worksheet
• Tab 1: Case Study: Annual Objectives
• Tab 2:. YOUR TURN: Annual Objectives

​

Your Company’s:

• Annual Objectives

​

Materials + �Information needed:

Final Deliverable

​

Once you have set your Annual Objectives in the OKR framework worksheet, you will have a final deliverable as shown here.

Final Deliverable example

Annualized Roadmap

​

​

With your Annual Objectives in place, the next step in the OKR framework is to create an annualized roadmap. Here, you can plot out the key projects and initiatives for the upcoming year. In this section, we will share best practices for creating quarterly Key Results and Initiatives which are essential for quarterly planning.

+

• Your copy of the OKR framework worksheet
• Tab 3: Case Study: Annualized Roadmap
• Tab 4: YOUR TURN: Annualized Roadmap

​

Materials + Information needed:

Your Company’s

• Annual Objectives
• Annualized Roadmap

​

What is an Annualized Roadmap?

13

The annualized roadmap is where you and your team turn each Annual Objective into a set of Initiatives and Key Results for the year. This structure is a helpful tool during quarterly planning.

Annualized Roadmap introduction

​

​

Best Practices:

• With your team, compile an exhaustive list of initiatives and key results for the coming year
• We recommend a google sheet to maximize visibility & collaboration
• Include all key projects and goals that are necessary to complete your Annual Objectives
• Once listed, the owners should estimate the timing of all Key Results and Initiatives listed

​

Watch outs:

• Normal day-to-day tasks should not be included in the annualized roadmap or any part of the OKR process. Ask yourself: will this move the needle? Is this essential to achieving our Annual Objectives?
• Being too focused on exact timing is not helpful for this exercise– there will be room to iterate during quarterly planning.

The SMART goal framework is an effective way to create clear and measurable Key Results & Initiatives

14

Annualized Roadmap Initiatives

​

​

• S - Specific (simple, sensible, significant)
• M - Measurable (meaningful, motivating)
• A - Achievable (agreed, attainable)
• R - Relevant (reasonable, realistic and resourced, results-based)
• T - Time bound (time-based, time-sensitive)

​

What are Key Results?

15

Key Results are high impact outcomes that show how you are tracking towards achieving your Annual Objectives. Key Results should be stretch goals for each area of the organization.

Annualized Roadmap Key Results

​

​

Best Practices:

• Key Results are quantifiable, measurable outcomes that indicate what success will look like in your business
• Make them stretch goals! If they’re easy to achieve, they aren’t true Key Results
• Key Results should have a clearly defined scope. It should be easy to see if they are achieved or not

​

​

Watch Outs:

• Broad or vague Key Results will lead to a lack of clarity on whether the target has been reached. This can cause misalignment across the team.
• Make sure to include Key Results that are not just about the bottom line or financials of the organization. It is just as important to set measurable goals for company culture, talent, NPS, customer satisfaction, etc.

​

Examples of effective Key Results:

​

16

Annualized Roadmap Key Results

​

​

• Achieve 80% market coverage
• Increase sales MOM by 10%
• Reach top 10 in Fortune 100 best places to work
• Recruit and Hire 5 key roles
• Raise Series A round of $50MM
• Receive NPS score of 75 or above
• Reduce CAC by 5% quarter over quarter
• Onboard 10 new customer accounts
• Launch website 2.0

​

What are Quarterly Initiatives?

17

Initiatives are the projects and tasks that need to be done in order to achieve your Key Results. If the Key Result is a destination, what do you need to do to get there?

​

Annualized Roadmap Initiatives

​

​

Best Practices:

• Focus on specific projects and tasks that will actively move the needle forward towards the ultimate goals of the business
• Initiatives should have clearly designed scope and a single owner within leadership that maintains responsibility for driving execution
• The Initiatives should clearly show what steps are needed to achieve the Key Results for each quarter

​

​

​

Watch outs

• Avoid simply listing day to day activities or BAU (business as usual) for any business function
• Initiatives are not the quantitative KPIs of the business - What steps are needed to reach those goals? Who needs to do what to achieve them?
• Ask yourself: Will it be clear when this Initiative is complete? The answer should be yes!

​

Examples of great Initiatives:

18

• Establish company operating system
• Launch Series A fundraising cycle
• Finalize annual budget with key stakeholders
• Migrate to Hubspot for CRM
• Design and execute strategy for next product launch
• Launch Bi-annual Performance Review cycle
• Publish 3 blog pieces on new product launches
• Host 3 in-person events this quarter

​

Annualized Roadmap Initiatives

​

​

example

Use the Case Study: Annualized Roadmap tab in the follow-along worksheet.

Then, on the YOUR TURN: Annualized Roadmap tab, create an exhaustive list of initiatives for each objective. We recommend having an internal with your team to explain the process.

Your Annualized Roadmap guide

• Your copy of the OKR framework worksheet
• Tab 3: Case Study: Annualized Roadmap
• Tab 4: YOUR TURN: Annualized Roadmap

​

Your Company’s:

• Annual Objectives
• Annualized Roadmap

​

​

Materials + �Information needed:

Quarterly Planning

Having completed the roadmap of Initiatives and Key Results for the year, it is time to focus on the specific quarter ahead. This quarterly planning process is repeatable, and will make it so that you can iterate on what your company’s priorities are from quarter to quarter. You will use your Annualized Roadmap as a guide to setting each quarter’s goals.

​

​

+

• Your copy of the OKR Framework Worksheet
• Tab 5: Case Study: �Q1 Planning
• Tab 6: YOUR TURN: �Q1 Planning

​

​

Materials + Information needed:

Your Company’s

• Annual Objectives
• Annualized Roadmap
• Q1 Plan

​

How to Facilitate the Quarterly Planning Process:

21

The point person that you designated to own the OKR process at your company (e.g. Chief of Staff, Operations Manager, etc.) will facilitate the quarterly planning process each quarter. Below are the steps needed for a successful implementation. For the purposes of this exercise, we will use Q1 as an example:

Quarterly Planning introduction

​

​

Best Practices:

• Once you have decided on the best platform for your company’s OKR process, the point person will share a template for team leaders to input their Initiatives and Key Results for each Annual Objective for the quarter
• We recommend using a Google worksheet for this first step to maximize ease of use for team collaboration and quick edits
• Once first inputs have been made, the point person will do any necessary clean-up/revising and review the proposed Initiatives and Key Results with the Executive team
• When alignment has been reached, the point person can then transcribe the finalized quarterly OKRs into the platform of your choice (e.g. Notion, Perdoo, etc.)
• The Executive team should present the final OKRs to the wider team and send out via email/Slack so Team leaders can review with their teams. This ensures everyone’s priorities are visible across the company

​

​

​

​

Quarterly planning best practices

22

• Prioritize, Prioritize, Prioritize- Less is more for quarterly OKRs!
• Try to orient around 5-7 Initiatives and Key Results for each Annual Objective
• It is better to do less better than overcommit
• Quarterly OKRs should encourage cross-functional collaboration and have multiple stakeholders across the team. We encourage cross team brainstorms when coming up with quarterly Initiatives and Key Results to make sure everyone is aligned on the work for the quarter.
• Initiatives and Key Results should always have a member of leadership as the owner. You can specify a “point person” if needed who is not on the leadership team.
• Our suggested timing for quarterly planning is later in this section!

​

Quarterly Planning introduction

​

​

example

Use the Case Study: Q1 Planning tab in the follow-along worksheet.

Then, on the YOUR TURN: Q1 Planning tab, create your own list.

• Your copy of the OKR framework worksheet
• Tab 3: Case Study: �Q1 Planning
• Tab 4: YOUR TURN: �Q1 Planning

​

Your Company’s:

• Annual Objectives
• Annualized Roadmap
• Q1 Plan

​

​

Materials + �Information needed:

Your Quarterly Planning guide

​

​

Rinse & repeat cadence

During this session, we share the rinse and repeat cadence for your organization’s OKR framework. Maintaining consistent timing for all prep work and deliverables is key to a successful OKR process. We will introduce best practices for how to facilitate monthly OKR reviews and our recommended timeline for quarterly planning throughout the year.

​

​

+

• Your copy of the OKR framework worksheet
• Tab 7: Case Study: Rinse & Repeat Cadence
• Tab 8: YOUR TURN: �Rinse & Repeat Cadence

​

​

Materials + Information needed:

Your Company’s

• Annual Objectives
• Annualized Roadmap
• Q1 Plan
• Rinse & Repeat Cadence

​

What are monthly OKR reviews?

25

During the first week of each month, leadership will meet to review the prior month’s progress on all Initiatives and Key Results.

Monthly OKR Review introduction

​

​

Meeting Prep:

• Monthly OKR reviews should be scheduled during the first week of each month (60 minutes recommended.
• A week prior, the OKR process owner should circulate a link to the quarterly OKRs for team leaders to update the monthly status with red/yellow/green
• Red: Experiencing roadblocks/likely will not be done by EOQ
• Yellow: In process but may not be complete by EOQ
• Green: On track to be complete by EOQ
• The status updates and any relevant should be updated prior to the meeting so that the majority of the time can be spent reviewing the items with a yellow and red status to see what can help push towards green

​

​

​

​

Watch Outs:

• Review all OKRs that have a yellow or red status for the month
• What steps need to happen for them to become a green by the end of the quarter?
• How can the leadership team help?

​

Quarterly planning calendar

26

Quarterly Planning timing

​

​

example

Review the recommended schedule and timeframes on the Case Study: Rinse & Repeat Cadence tab. Schedule as much in advance as possible the upcoming calls and record them on YOUR TURN: Rinse & Repeat Cadence tab.

• Your copy of the OKR Framework Worksheet
• Tab 7: Case Study: Rinse & Repeat Cadence
• Tab 8: YOUR TURN: �Rinse & Repeat Cadence

​

Your Company’s:

• Annual Objectives
• Annualized Roadmap
• Q1 Plan
• Rinse & Repeat Cadence

​

​

Materials + �Information needed:

Rinse & Repeat Cadence guide

​

​

Conclusion

At the same time, remember to celebrate your victories by recognizing the teams that orchestrated them. Use your win as an opportunity to foster connections between team members and strengthen your culture of collaboration. Make note of your successes, as they often provide insights into how your company works and what your people are capable of.

You now have everything you need to use OKR processes in your own company. We have found this framework extremely effective for fostering effective collaboration, unifying various teams, and keeping your company focused on the big picture.

​

​

As you move forward into the coming year, you’re bound to experience your share of exciting wins and disappointing losses. Both are vitally important to your OKR process. Remember, quarterly OKRs are meant to be stretch goals; if your list was covered in green at the end of each quarter, you are likely not pushing hard enough. If (and when) you come up short of your goals, take it as a chance to identify which steps along the way could be improved. Learn from your failures, and use them to improve your operations and inform your future OKRs. Our EOQ reds can teach us just as much, if not more, than our greens.

Appendix

What is the best tech stack for your OKR Process?

30

There are a number of tools you can leverage to run your OKR process. Here are a few worth exploring:

OKR tools

​

​