Strategic Planning That Actually Gets Used: A Simple, Human Approach for Busy Leaders

Simple tools for leaders

Strategic planning doesn’t have to be a lengthy, expensive process. It’s easier than you think and can be genuinely energizing: an opportunity to create more engagement, break down communication silos, and get everyone talking and working together. It will help you pinpoint where your challenges are and where things are blocked. Most importantly, it's an opportunity to wrangle those blockages and remove the obstacles to more fluid operation and growth. Whether you run a non-profit, a start-up, or have been in business for 40 years - use strategic planning to pause, reflect, and shift from reactive habits to more intentional, responsive action.

Why is strategic planning not the scary process you may have been led to believe?

It is absolutely essential to have a vision and road map of where your organization is headed, and most likely you already have one - or several, if you have been in business a long time. Strategy and direction come out of where you have already been and what you already know. What worked, and what did not? Who are your customers/clients? Has that changed? What do they get from you that they need and what are they not getting from you that you could provide? What is the unique manner in which you provide it or will provide it?

You know this stuff - you live it, as do the managers and staff you work with. Your customers know it, your suppliers know it, and often your competitors know it too.

A real strategic plan is a useful and used living document - one that holds an aspirational  story and also the real story. When you keep this document close to you and in mind by using it all the time, you will have a grip on the big picture in your organization.

A strategic plan is about knowing your marketplace, your industry, the waters you are swimming in. Or it should be about getting to know all those things again. What are the opportunities and what are the constraints? To entrepreneurs, and leaders of all kinds, these things are already in your head, all the time - because you are listening to your staff, your clients, and your competitors. So, when you do strategic planning, you start with what you know. As you undertake a strategic planning process, it's simple - you see the relationships between what you know and where you could go.

What is the role of everyone in your organization in strategic planning?

A vision and a plan are not enough on their own. Unless you’re a one-person operational whiz, you need the people in your organization to help you make that vision real.

Your employees are the ones on the ground carrying out the work every day. They see where things flow and where they get stuck. Do they share your sense of what’s working and what isn’t? Do you know their constraints, challenges, and ideas? They hold pieces of the puzzle you don’t have, and their participation is essential to building an accurate picture of operations and deciding how to move forward.

Effective leaders listen deeply, help people work collaboratively, and tap into the creativity and enthusiasm that emerge when people feel valued for the work they do. Strategic planning is a powerful opportunity to model this way of leading.

When you’re ready to bring people into the conversation and really listen, the next step is to guide them through a simple, structured process.

So how do you do strategic planning simply?

Strategic planning is just a series of questions and explorations. It is not rocket science - it is a simple process of creating a path forward for your organization that is realistic and attainable because you have asked all the right questions.

Below is a process and sets of questions that could be undertaken and adapted by most small and medium-sized organizations.

A note here to acknowledge that for larger organizations of course, strategic planning can be a much more involved process because more people need to contribute to it. But the objectives and the processes are essentially  the same.

1) Kick it off!

• Decide how much time you will put aside for this process, and over what period of time. Will you do it on-site? It doesn't need to take place at a weekend retreat or a fancy venue. What IS important is to assemble everyone, and ensure they are comfortable and able to relax and be present.

• Invite your staff and let them know you value their collaboration and their insights, and are looking forward to working with them on this important initiative. Let everyone know what the process will be, and how long it will take.

• Hire a facilitator who will foster fun and respectful conversations and organize the process of collecting and presenting data. It's important that you as a leader are free to participate in this process - so having others to facilitate is important.

• Order pizza! And make sure to provide lots of water, coffee, fruit, and chocolate.

2) Dive into doing a SWOT with your organization. What are the organization's Strengths - Vulnerabilities (rather than Weaknesses) - Opportunities - Threats? This is such a great exercise to do as a team. I find the discussions to be rich!

• What are our unique strengths? What are we doing well?

• What are our vulnerabilities, and what could we be doing better?

• What opportunities are out there for the organization?

• What threats and uncertainties do we face internally, in the marketplace, and beyond?

3) To build the plan itself, here are the most important questions that need to be answered:

• What is it we do, what is our offer, to whom, and why? What is it that we believe the world needs and we have the capacity to give? Is this the same as it was when we started, or has it changed, expanded, or shrunk?

• Is there alignment of this vision with everyone in the organization? If not - then this is the moment to work on articulating a unified vision and goals together.

• What is the plan? What do we want to accomplish this year, next year, and the year after?

• What are the steps we need to take in order to do these things?

• Who will do what to get these things done? And by when?

• How will we know that we are successful (KPIs - key performance indicators)?

• How will we keep the ball moving?

Done? Or just begun...

So, your organization has gone through the whole process, and you now have a mostly agreed-upon vision, a 3-year plan, a timeline, and some KPIs. The consultant has sent a gorgeously illustrated document with a clear road map to follow.

Presenting a beautiful plan to investors, bankers, and supporters is important. But the document you end up with is something you should not be afraid to mess up. Revisit it regularly, scribble notes and comments in the margins, and update it often. It should evolve as things change, because things rarely unfold exactly as you imagined. Understanding why is crucial if your organization is going to pivot and adapt.

The question now is: how will you keep this plan visible and accessible to the people who created it with you?

• How will they maintain their commitments to action?

• Is there a committee or working group to steward the plan?

• Are follow-up meetings scheduled?

• Will people see this as a living document, not a report that gets filed away?

• How often will you meet to review progress and adjust course?

  
  

Treating the plan as “just begun” rather than “done” is what turns a strategic planning exercise into real, sustained change.

Why are most strategic plans not acted upon?

Sad, but true - the time, money, effort, and pizza - is often wasted. Ah, we think, planning is done, that's over… You have all the best intentions in the world to follow it. But many of us just do not….

Why?

1. Because it is not grounded in what you know and what others in your organization know.

2. Because you haven't validated your plan with what you hear from customers, investors, and suppliers, and what you've seen in your market research, thus it is not realistic.

3. Because you have created a good plan that is not visible or usable for you and your organization,

4. and thus you don't revisit it and recalibrate - and so, it is not a living document.

5. Because you are not using your plan to get feedback and understand how and why you over-achieved or under-achieved what was forecast.

Here's an optional but very effective add-on to strategic planning:

The personal SWOT - start with yourself!

This is not usually considered to be part of strategic planning, but preparing leadership to go through this process will ensure its success - especially if there have been difficult dynamics within the organization or the leadership team. Strategic planning can expose and even widen the cracks within an organization. However, an aligned leadership team will be able to smoothly guide and accompany an organization through the planning process, and also through the fulfillment of the plan.

 The easiest way to start is for you to sit down with someone who can ask you the right questions. A coach is great for this process - especially one who understands the process of strategic planning. Prepare yourself for planning, and then bring the process and the questions to the people you need to calibrate and develop this plan with. And at the other end of the whole process, your coach can be the one to help you keep your personal commitment to goals and actions, and rethink with you what is working and not working.

As a leader, are you aware of your own challenges, vulnerabilities, and blind spots? Do a personal SWOT (Strengths - Vulnerabilities (rather than Weaknesses) - Opportunities - Threats), and then explore:

• What you want to accomplish this year, next year, and the year after to up your game as a leader?

• What are the steps you need to take to accomplish these things?

• How will you measure your success?

• How will you recalibrate and how will you know you need to recalibrate?

• What is the process (or the person) who will help you maintain your commitment to your goals?

Strategic planning doesn’t begin with a three-day retreat or a glossy 60-page deck. It begins when you, as a leader, decide to pause, ask better questions, and invite your people into the conversation. When strategy is grounded in what you already know, tested against real data and real voices, and captured in a living document, it becomes one of your most powerful leadership practices instead of another task on the calendar.

You don’t need perfection to start. You need curiosity, a willingness to listen, and a commitment to revisit the plan regularly. If you do that, strategic planning stops being something you “have to do” every few years and becomes a shared roadmap that energizes your team and guides everyday decisions. So pick a time, gather your people, order the pizza, and begin. The most strategic move you can make might simply be starting the conversation.

If you’d like support designing or facilitating a simple, human strategic planning process for your organization, I’d be glad to help. Get in touch.