Substantive review of prior quarter performance, discussion of leading indicators of next quarter performance and plan changes for initiatives. At this meeting we complete a mid-quarter to review the current OKRs, discuss success, pain points and ultimately create the strategic goals for the following quarter.

The main goal of this meeting is to have Sales, Marketing & Product aligned and have all other teams aligned to their plan in a supporting role. During the meeting, your head of sales should present their strategic plan and major asks from the team, particularly from Marketing & Product.

This meeting is held on the last month of the current quarter. We typically include the last “monthly meeting” of the quarter in the agenda for this meeting for ease of scheduling.

Quarterly Planning Agenda

Around the mid-point of the second month of a quarter the ELT will meet offsite to review prior and current quarter progress and plan for the coming period.

Discussions and activities at the quarterly offsite reviews are considered confidential. The default level of confidentiality is Nothing, Nobody, Never. The means you say nothing about the discussion, to no one and that confidentiality endures forever. The intent of this is to create a

safe and candid space for discussions of material import to the company.

At the completion of the offsite we’ll create specific messaging points for people to share with their team. The key is simply to provide that communication in a deliberate fashion.

We’ll provide a current set of initiatives and related key results to enable Department level OKRs.

Pre-Meeting Work – ELT members will provide the meeting organizer with three discussion topics they would like addressed during the meeting

Meeting Rules of Engagement

Confidentiality
- What is said here stays here
- Ideal is Nothing, Nobody, Never
- Nothing – You repeat nothing that was said here
- Nobody – You repeat it to Nobody.
- Never means forever.
- Obviously, things here are going to be rolled out to the company – that’s not the focus
- The focus is sharing and if someone shares something here don’t share it with someone else unless you get permission
Practice caring concern as we go
- Care about the person, care about the company
- Concern about how the approach we discuss here impacts
- A specific person on this team
- This team as a whole
- The lives of our employees
- The world
This session is not about being right, it’s about getting aligned and getting us on the same page
Be present
- Take your cell phone out now
- Turn off the ringer
- Place it face down on the table
- Don’t check it while we are in session
- You can use technology to take notes – you cannot use it to check e-mail
- We’ll take breaks at a few points where you can check e-mails – so get your fix then
Be committed
- And then commit to being here
If you’re comfortable, share. If you’re not comfortable that’s useful as well, talk through it!

Day One – Context

What’s the context in which we’re operating in now and how should that inform our focus for next yeat and beyond?
Updates (All)
- ELT members provides updates on what’s happening in their business and personal life. Format for the updates:
- One Word Open – One word describing where you are at today
- Bests – What is the best thing that happened to you in the past 90 days and why was it the best?
- Worsts – What has caused you the greatest pain, disappointment, or concern in the past 30 days?
- Looking Forward – What are you looking forward to the most over the next 90 days and why?
- Concern or Dread – What will be your greatest challenge in the next 90 days and how do you feel about it?
- Update Notes
  - Updates are untimed but you’ll generally want to keep them to between five and ten minutes
  - While the person is providing the update: No discussion. No interruptions.
  - What updates should be
    - About the significant things in your life or our business
    - Focused on key challenges and opportunities occupying your thoughts
    - Focused on your feelings about things
  - What updates should not be
    - Facebook Updates – This is not the list of status changes since our last forum or a chronological statement of events in your life. This is about important things that have impacted you.
    - Travelog – This is not the list of the places that you have been and the things that you have seen. those things had on you and why they were emotionally resonant
Retrospective (Organizer)
- For the prior quarter (Q2, Q3, Q4) or prior year (Q1) provide an exercise to reflect on:
  - What worked?
  - What didn’t work?
  - Operational issues
  - OKRs we failed at
    - What do we want to change because of that?
- Do we have the right set of OKRs for the next quarter? Do we need to move, add, remove or otherwise change them?
- Are there any emergent risks to achieving our goals in future quarters that we need to act on nowAre there any backlog initiatives we need to pull forward and take action on?
- Are there parts of our core strategy (Mission, Vision, Values, Key Value Drivers, Market Requirements, Customer Profiles) we need to change?
  - Once a quarter the contents of the long term strategy are open to review.
  - Typically, this review is focused on specific initiatives we are tracking and definition of those.
  - Broader questions or updates that are needed to shape long term strategy, however, are fair game.
Macroeconomic Environments (CEO)
- Liquidity Timing – Where are we tracking in terms of timing for our next liquidity event? Investor Sentiment – What are our investors concerned about?
- Market Environment – What is the market for technology companies doing? Do we need to make given our current and target scale?
  - What are the options there?
  - Where would they coach the team to focus?
  - How should that inform our approach?
Competitive Environment (Head of Marketing)
- Competitor – Updates on each of the key competitors from the person that tracks that competitor
- Win / Loss Analysis -Summary of the win / loss data from the prior quarter
- Product Perspective (Head of Product)
  - What areas is product concerned about or focused on from a competition perspective?
  - What pressures do we want to address? What are we studiously ignoring?
  - Discussion
Frontline Feedback (Sales Reps, CS Reps)
- Forum for direct feedback from reps on what’s working and what’s not working in the sales and CS process.
  - New and AE feedback – what are we hearing in the New
  - Current Accounts and AM feedback (Ryan)
Market Updates (Head of Sales)
- An overview of structural changes and updates in our market.
  - Leadership team on what’s working and what’s not.
Pipeline Generation Review (Head of Sales and Marketing) – For each of Marketing, AE, AM, SDR and Partner generated pipeline
- What worked?
- What didn’t?
- What do we want to do about it?
Operations Review (CFO)
- Last Quarter – How’d we do last quarter across KPIs?
- Current – How are we tracking in the current quarter on KPIs?
- Future – What areas of concern do we have for the rest of the year on hitting specific KPIs?
- Where is there risk?
- This should all be informed by the most recent forecasting exercise + FP&A’s view of the world and the areas of risk that need attention
Talent Review (CPO)
- Status of the team and overall engagement
- Progress on talent initiatives
Budget Review (CFO)
- Budget overview for next quarter or year as appropriate
  - Overview of full year proposed budget (Q1)
  - Overview of variance to budget, material execution themes, areas of concern (Q2, Q3,Q4)
- Three Year Plan Updates
  - Review of key aspects of three year plan inclusive of actuals and current quarter forecast
  - Notes on areas of risk or over performance and potential operational impact
Product Review (Andrew)
- What we built last quarter
- What we’re building now
- What we’re building next quarter
- What are the core things we want to talk through and get aligned on?
- If you hav a product council this is not a replay of that – this is a moment to have more substantive discussion on points of alignment that are
Customer Review (Head of CS)
- What’s working?
- What’s not?
- What are we planning to do about it?

Day Two – Priorities

Quarterly Initiatives
- Definition of and alignment on key, company-wide priorities for next quarter or year.
- These take into account the context and the financial plan for the
Discussion Topics
- Various discussion topics that were raised as areas of concern or needing alignment
Initiatives Exercise
- Write down the top initiatives for the business for the coming time period – quarterly (Q1, Q2, Q3); annual (Q4)
- Quarterly initiatives can either inherent from the current corporate wide initiatives or not
- You can propose a new corporate wide-objective to replace one of the current ones if you feel it’s strongly needed
- initiatives would cover
  - Changes to the business or initiatives needed to hit our operating targets
  - Acceleration and upside – things we need to do that are above and beyond the scope of what we have to do day-to-day
  - Can be anything – product features, new services, updated services, changes in our employee engagement approach – key is their critical across the company
  - Existential risks to the company
  - Big upside opportunities for us
- We’ll put the answers up on the board and consolidate commonalities
- Priorities are pitted against each other until we narrow the list to a candidate set of OKRs for the next quarter

Day Three – Execution

Detailing out of the tasks, interdependencies and product and solution roadmap implications based on the 2024 priorities.
Initiatives Definition
- Review and document the initiatives defined during the prior day
- One slide per
- Specific owner for each
- Breakouts of the key results and measure for each
- Lots of notes on scope, what’s in, and what’s out for each

Day Four – Wrap-up

Messaging – Creating the follow-up messaging points for distribution to the team about the results of the offsite

Meeting Follow-up

Documentation of new OKRs from meeting and distribution to relevant team owners
Documentation of any non-OKR follow-up items
Monday with Managers session to cover (i) results of the meeting and (ii) communication plan for the results from the meeting

Notes

Quarterly it’s about tweaking and execution – Q1, Q2, Q4 meetings
Annually it’s about bigger picture recaps associated with that – Q3 meeting
Both quarterly and annually we’d compare what our plan was going into the period versus what we actually did
We like the idea of doing small group working sessions as part of the overall activity and rolling up the results of those
We like the idea of a meal together
We want to have some drinks together – just not too many
We like to travel every other meeting so we’re really offsite so having a compelling place to go (think warm in the winter, cool in the summer) is great