Annual Planning and Finding Your “Why”

It’s that magical time of year when big box stores jump straight from Halloween into the holiday season, signaling the rapidly approaching end of the year. For most people, this is the time to start planning for the holidays – whether it’s shopping, traveling, or hosting family. But for business leaders, it means something else: annual planning.

This is a critical time for you and your management team. Annual planning is when you review the previous year and plan for the next. It’s a time to step back, align your team, and set the rhythm for the next 12 months, and more importantly, discover or re-discover the “why” behind your planning.

The great coaches within the Gravitas community have helped business leaders all over the world successfully and their own “why,” develop their annual plans, and execute accordingly. So we asked Adam Siegel, Gravitas Impact premium coach and executive director of Visage Invest, to sit down with us to discuss the ins and outs of annual planning. Let’s explore what he had to say.

Gravitas: When talking about “finding the why,” we mean answering questions such as: “Why keep going? Why choose these goals? Why take this direction? Why focus on (x) strategy?” How critical is the “why” to successful annual planning? Why is the “why” so important?

Siegel: The “why” is so important because people and companies never really think about “why” they do what they do. Too often they focus on the “what.”The reason the “why” is so important to annual planning is that they must start with the company’s core purpose (the “why”).

The “why” needs to go beyond making a dollar. It often inspires change, and also ends up creating a lot of good in the world – or at least in a market. The“why” typically speaks to people’s hearts and provides drive and engagement –far greater than any “what” I have ever seen.

In my experience with running large businesses and advising growth-focused company leadership teams, it is amazing to watch the lights go on when a team discovers their “why.” I typically ensure this is one of the first leadership team exercises we do because it ends up informing all future decisions. Frequently, I or a member of a leadership team will challenge a suggestion or recommendation with “how does that support our core purpose?”

Gravitas: Should companies go into annual planning with a clear idea of their “why?”

Siegel: Going into an annual planning without a clear “why” actually creates a great opportunity. It provides a great stage to establish your “why” BEFORE you commence your New Year business plans. Even if a client already has a clear “why,” I typically review it with the leadership team (amongst other things) to ensure relevance. It’s also a great opportunity for team alignment!

Gravitas: How can a leader best discover the “why” behind their annual planning? What are some questions they can ask themselves? What are some activities/exercises they can us to help?

Siegel: I use a proven technique called the “5 Whys.” It means working as a group to first understand what the business does, and then asking why over and over. By the time you ask “why” multiple times, you start drilling down to the real purpose of why the business is in existence – it is a VERY powerful approach!

Gravitas: Who decides what the “why” is? Should this be something the leader or leadership team does on their own? Should it include other employees/perspectives?

Siegel: Definitely as a team. There are too many engagement and team learning opportunities to determine this by any individual.

Gravitas: What are some potential roadblocks to finding the “why”? What could possibly distort this discovery process?

Siegel: The challenge is enabling everyone to get into an open frame of mind. Many times, I have had a CEO or senior executive think they know the company’s core purpose before we commence. It may be in a previous strategic plan, written on the wall in the entry to the office, or in someone’s head. The key is to respectfully suggest that we set aside any previous core purposes or ideas, and just follow the process.

There also needs to be a strong level of team health, i.e. a trusting environment where people feel open to express their views and experiences; or an environment that has no fear of conflict – where people feel that their ideas or suggestions are respected and heard, and not challenged or judged.



1. The “why” is your company’s core purpose. It’s the central driving force that moves your company towards its goals. It validates your decisions and provides you with purpose.

2. Annual planning is actually a great time to discover your “why.” Even if you think you already know what it might be, it’s good to review it, challenge it, and/or set it aside completely until you’ve finished the planning process.

3. You can utilize Siegel’s “5 Whys” exercise to understand the core of what the business does by drilling down to get to the “Why.”

4. Always include your full team when it comes to determining the “why.” This provides you with perspectives you may not have yet considered, and opens the door for team building and learning opportunities.

5. Go into your annual planning with a fresh mindset. Set aside previous notions of your “why” and allow the process and teamwork to develop. Ensure that you allow for an open and honest environment so that everyone can speak up and share their opinions, thoughts, goals, and concerns without feeling judged or intimidated.

As a coach, is your experience similar to Siegel’s? How do you help your clients discover their why? What processes, exercises or theories do you put into practice? Share them with us!