I am an advocate for simple and collaborative methods for defining strategy for a team, department or company. Many strategy frameworks are too complex and while they may seem democratic (by embracing voting, for example), they usually lead to the middling harmony of sticking to the status quo. Instead, your collaborative process should encourage rigorous debate to overcome the mediocrity of consensus.

Any strategic planning process should aim to:

  1. Establish a thorough common understanding of the desired outcomes.
  2. Identify, acknowledge and debate perceived obstacles.
  3. Prioritise a small number of high-leverage opportunities to tackle.

Converging on desired outcomes

While high-level goals may be relatively clear (e.g., Our goal is to become the most loved Help Desk application for Retailers), individuals often aren't on the same page regarding what the ideal end-state actually looks like (e.g., are we targeting all retailers or retailers of a specific size? Online only or in-store?). For this reason, I think it's critical to start any planning session by defining a very specific view of the ideal end-state of the project/product/team/organisation.

To do this, I recommend a silent brainstorm. Essentially, each member of the team will independently describe their view of the ideal end-state. After this, they'll share their view and the team will discuss and debate the various descriptions in an attempt to converge on a common understanding of what we're trying to achieve.

Let's assume a company with industry-leading support wants to take better advantage of this by making their high-quality support an explicit selling point of the software. A description of the end state might be:

  • Customers are happy and love us.
  • Customers are happy to give us a testimonial or participate in a case study.
  • NPS of over 80.
  • First-response times are under four hours.

Each of these points can be debated and refined based on the diverse descriptions brought to the table by the team. In the example above, some may disagree with the importance of first-response times, instead believing that a quality response that actually solves the problem is better than a quick but relatively superficial response. By making explicit these differences of opinion regarding what the ideal state looks like, you can use debate to converge on a unified view.

Acknowledge perceived obstacles

When goals are set by management or even by a simple vote, it is common for individual contributors who are responsible for working towards these goals to have unspoken skepticism towards the achievability of these goals. Often, this skepticism is well-founded and based on obstacles that should be explored and tackled before undergoing the broader initiative. Alternatively, this skepticism can be based on perceived obstacles that are not valid and debating them can lead to stronger team confidence. Either way, acknowledging and discussing any perceived obstacles is usually very valuable.

If you have already got a description of your desired end state, this can be easy to do. Simply ask your team to identify some obstacles for achieving each aspect if the desired end state and discuss these obstacles. Try to converge on a set of legitimate obstacles that the team will need to consider along the way.

Prioritise a small number of key opportunities

Each aspect of your ideal state and obstacles will likely translate into one or more opportunities. For example, if one aspect of your nirvana is to improve customer response times, ask your team what they think they need to do to get there. Additionally, review each obstacle and try to find opportunities to eliminate these obstacles.

Again, the goal here is to achieve consensus through debate rather than a simple vote. Each opportunity should be scrutinised by the team and eventually prioritised with the goal to define an explicit, common understanding of what is the most important work to tackle first. These opportunities should be loosely defined initiatives that can later be further explored by the team.