Strategic Planning


I was recently asked to lay out a strategic planning process that I could potentially implement.  Oddly, I like doing this kind of thinking, so spent a few days mulling over what my ‘ideal’ structure would look like.  In my career, I have witnessed only a few such processes up-close, and recognize that the devil is very much in the details.  But below is my overall framing.

(Would love to hear from any of you how you conduct strategic planning at your company, what works well, any pitfalls, etc.)

Purpose of strategic planning 

To create alignment across functions, teams, and individuals on the goals and initiatives required to achieve the company’s vision.  The process should include and help inform:

  • Vision:  long-term outcome and purpose of the company (“We envision a world where ___, and our role in achieving this vision is ___.”)
  • Goals:  medium-term milestones to reach vision; near-term projects and goals
  • People need/gaps:  performance of leadership, functions, teams, and individuals
  • Measurement:  communication and tracking of progress (“We know we are on/off track because ___”)

Given the ambiguity and fast-paced changes of today’s business world, a strong planning process must be flexible and open to course-correction.  In addition, to ensure true alignment, a clear communications plan and cascade is required.

Here is a highly-simplified schematic of what’s included in a strategic planning process, with the x-axis measuring time:

Screen Shot 2017-06-02 at 8.19.23 AM

Proposed process

Step 1:  Frame the vision of the company.  

Make sure that it balances aspiration with achievability, and explains the company’s role in making that vision a reality.  Since this is meant to inspire current and future employees, it should be easy to communicate and ideally appeal to people across ‘purpose-profiles’ — addressing impact on society, the organization, and individuals.  (Note:  ‘purpose-profiles’ comes from Imperative!’s work on driving purpose at work.)

Step 2:  Break down the vision into 5-, 2-, and 1-year milestones.  

For each time horizon, answer the question, “What needs to be true in x years for us to get to this vision in y years?”  Another way to do this — which could be really fun (or not) — is to create a future press release that would be issued about the company in 1-2 years that explains what’s happened and why (I think Amazon does something like this?).

Step 3:  Starting with the 5-year milestones, work backwards to today in determining the initiatives and outcomes required.  

You can start somewhat at a high-level when thinking 5 years out, but as you get closer to today, become much more specific about expected outcomes and initiatives.  

Categorize the issues and outcomes along the following dimensions to be comprehensive:

  • Growth initiatives:  “What are the key growth initiatives we need to undergo to achieve this milestone?”  For example, could include:  international expansion; product adjacencies; new customer segment; expanded delivery channels; acquisitions; etc.  Growth initiatives tend to require cross-functional efforts.  
  • Maintenance initiatives:  “What do we need to do to ensure we can meet the needs of our existing stakeholders — customers and employees?”  Maintenance initiatives mostly include volume-driven activities that achieve a target SLA, cost-metric, etc.  For example, automating internal processes; offshoring customer support; etc.  These types of initiatives are often impacted by previous growth initiatives, with a time-lag.  Maintenance initiatives tend to be function-specific.  To avoid cyclical and frustrating conversations, should set standards/philosophy on service levels; employee centricity; tech debt levels; load time levels; cost per customer acquisition; etc.

To clarify the relationship between growth and maintenance initiatives, let’s use the analogy of building a house.  A growth initiative is like adding another floor.  If you are going to do that, you need to also consider the impact of that new floor on the existing structure, and make accommodations to handle the weight, changes to emergency exits and fire code stuff, etc.  These accommodations are what I mean by maintenance initiatives.  You need both types of initiatives to build a sound structure.


  • People impact:


      • Hiring:  “Given these initiatives, where are the skill and knowledge gaps that we should get ahead of?”
      • Organization:  “How can we best organize teams to ensure we can accomplish these initiatives?”
      • Goals:  “What must we do at the company / functional / individual level to achieve these initiatives?”
      • Performance:  “Do we have the right people and skills at the individual level to get us to our goals?”

It’s important to be continuously gauging whether you have the right people, expertise, and skills on the team to get you where you need to go.  Here is how I imagine the iterative ‘thought-process’ would look like, and who is responsible for making these decisions:

Screen Shot 2017-06-03 at 7.44.12 AM Step 4:  For the 1-year goals, engage the organization in discussing how each function and individual plays a role.  

To do this effectively, it’s important that the vision + medium-term and short-term milestones are clear and have been communicated well.  

  1. Executives, in collaboration with functional leaders, should determine the key growth initiatives the company should undertake and who will lead them.  These may require cross-team collaboration (perhaps through a dedicated SWAT team).  
  2. Leaders of these growth initiatives should set clear milestones/metrics/timing.  Should also assign a ‘confidence-level’ of achievement and why, to ensure they are thinking about the resources and risks.
  3. Next, knowing what the growth initiatives are, consider the impact on stakeholders, and determine what the maintenance initiatives will be.  This should be largely driven by the functional leaders.  Again:  clear milestones/metrics/timing/confidence-level.
  4. Then, managers should set team goals to support both the growth and maintenance initiatives.  Again:  milestones/metrics/timing/confidence-level.
  5. Finally, managers work with individuals to do the same thing.

Step 5:  Articulate all of the above in a shareable and easily-accessible file/site/tool.  

That way, everyone knows what everyone else is responsible for.  If you use an HRIS like Namely (not a recommendation) that offers a directory of employees that can be customized by individual, then that can act as your repository.

Step 6:  Track and revisit these goals/metrics at a regular cadence (3 months?) to check on progress and gaps. 

The growth and maintenance initiatives shouldn’t change significantly during a year, but how the work is being done may at the team and individual levels.  If there ARE big, unexpected changes to the company-level goals or initiatives, make sure to convene the company and explain what has changed and how that might impact different parts of the org.  

Other random considerations

I always wonder why companies tend to do these kinds of big, time-consuming exercises during busy times (like year-end or the beginning of the year).  Unless there is a practical reason for it, I might suggest undergoing this type of planning process during a ‘low season’, so that people can be dedicated to the effort.

Make sure to always explain the WHY of initiatives (as Simon Sinek also reinforces in his TED talk).  People need to understand or else they feel alienated from purpose.  This may be simplistic, but I always think about communicating the WHAT, WHY, WHEN, and then ask my teams to figure out the HOW (and sometimes the more realistic WHEN 😁).

Finally, it’s important for execs to repeat the same stuff, using the same language, multiple times.  Especially at a rapidly-growing company where you’ll likely have 30-40 new hires every 5-6 months.  I think there is some stat about people needing to hear things 7x before they internalize it.  So make sure to reiterate the vision and goals frequently.  

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