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Rolling Out and Executing Your Strategic Plan

Rolling Out and Executing Your Strategic Plan

Sept 16 - Session 3: Rolling Out and Executing Your Strategic Plan

  • ​Understanding the differences between a strategic plan and annual planning
  • ​Communicating the plan to the organization
  • ​Aligning jobs/resources to strategy
  • ​Implementing and tracking KPI’s related to your plan


Brian Webb (CoS at Clubhouse/Shortcut)

Sydney Cummings (VP of Business Operations at Terminus)

Emad ElShawa (Chief of Staff at Fundbox)

Moderated by:

Abby Parker (COO at Elate)

Elate is the leading Strategic Planning software built to help high growth companies communicate their vision, create alignment, and track performance all in one place.

Question: What does your Strategic Planning Process look like? When does it start and who is typically involved?

Emad (Funbox): Before we start, we ask three questions: 1) where are we as a company? 2) what would we like to accomplish as a company? 3) how do we get to that point where we want to go and what do we need to execute on in order to achieve those goals

The timing is: 2-3 months before the end of each year.

Sydney (Terminus): we think about in multiple levels:

  1. Long-term vision (2-3 year out vision)
  2. Quarterly department goals 

Timeline: start in the summer before the following year. Start with high-level conversations to get the creative juices flowing. Then have follow-up meetings to narrow-in. Like to have this detailed out by November. 

We adopt OKR on a company level annually, and quarterly on a department and individual level.

Brian (Clubhouse): See annual planning as one component and strategy as a separate component (M&A, international, etc). 

  • This process kicks off in October and is in 4 phases:
  • Leadership / CEO shares concise vision
  • Create one key plan and dependencies and push back down to team for buy-ins
  • Do OKR’s on a quarterly basis.

Strategy is very difficult and it works well when a company has a decision calculus for how to think about strategy. They use these four prompts:

  • Can we be market leader?
  • Business model that’s hard to replicate?
  • Business growth that enables capturing customers at high velocity?
  • Do we have network effects?

Do you prep anything going into the meeting to make sure it’s successful?

Sydney (Terminus): High level conversations starting in the summer led by our CEO and CoS. This gives light prep on brainstorming for learnings and current state and gets more specific over-time. Focus on attacking blockers and creating goals.

How do you turn these big meetings into actionable items for people on day-to-day during planning sessions?

Brian (Shortcut):

  • Vision, mission, values are all important. Company needs to know how to connect the dots.
  • Use tools like Elate to scale this process. CEO or anyone In a department should be able to access. 
  • The questions of: "what is the company mission and what is the most important thing your function is working on?" is unfortunately usually not answered correctly by many people. 

What does the rollout look like for you at Fundbox?

Emad (fundbox):

  • CEO gets in front of company and selling the vision. Starts with All Hands - here’s where company is, here’s what we’ve accomplished in past months and here’s where we’re heading and what we hope to accomplish.
  • After that, it filters down to next level of exec team:
  • Led by CoS
  • Core business heads
  • Develop a list of core initiatives
  • Company offsite - brainstorm ideas of how they can execute on initiatives. Super important. Keep people together in a room.
  • Exec team decides which initiatives will have the greatest impact

How does rollout look in the remote world?

Emad (fundbox): whiteboarding has been harder remotely. For the first time since COVID, we recently had our first in-person planning session and it went well. 

Sydney (Terminus): COVID forced them to become efficient with their time. Frequently tweaking the formatwith prep sessions and smaller group meetings ahead of time, forecasting, etc, cadence during COVID

Brian (Shortcut): it’s a lot harder remotely. Echos a lot of what Sydney said. 

On Communicating Progress to the Company

Brian (Shortcut):

  • Use town hall to talk about business drivers. Are we above or below plan and why
  • Tough to make this process and information important to every employee

Emad (Fundbox):

  • How to have KPIs and key metrics resonate with the team: Track projects individually. Use the traffic light system: if yellow or red, what do they need from the team to keep them moving forward?
  • Key metrics meeting: tracks important metrics on weekly basis. Are we tracking to this goals, what’s lagging, where is intervention needed?
  • Weekly leadership meeting with exec team: Identified problems and Here’s what can be done to fix it

Sydney (Terminus): The Art of communication:

  • Critical at any stage
  • Sometimes more prescriptive directive. 
  • Get buy-in from the top. Have previously failed at OKR’s previously 
  • Start big with a brainstorm aligned to vision. Narrow down and get more specific as you go.
  • Keep a creative and strategic space vs. just getting into narrow tactical and execution mode.

Emad (Funbox):

  • CoS tend to have a super focus to accomplish the goal in front of them. Not hitting the goal shouldn’t always be deemed as a failure. Learning is really important.

What is the most important part of the OKR and Planning process for CoS?

Brian (Shortcut):

  • It can treacherous waters getting into OKR’s 
  • CoS needs to over index on pushing this forward and maintaining the process

How do you define success with respect to OKR adoption across the org?

Sydney (Terminus):

  • If everybody in the org can understand the shared company goals and knows them offhand - thats’ a major success
  • Are OKR’s being used in regular vernacular? If yes, that’s a success.
  • Have used Lattice to see how many people are using OKRs 

What is your final piece advice for us and the CoS?

Brian (Shortcut):

  • OKR + A(action): don’t gloss over what initiatives and actions you’re doing to get to that

Sydney (Terminus):

  • Don’t get wrapped up in the process. Turn back to why you’re doing this and why it will help you solve the biggest problems you have. Follow your gut on what works best for you. 

Emad (Fundbox):

  • We get accustomed and focused on always tackling the next problem that presents itself. Instead, leverage your personal time purposefully to the best you can.
  • Don’t let someone else’s urgency distract you from what your job is as a Chief of Staff. Make the most of your time first.
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