Strategic planning tips from an expert
Finding the time for everything that needs to get done as a small business owner can feel impossible. But annual strategic planning is a powerful tool that can actually help you get time back.
If you’re new to strategic planning though, it can be hard to know where to start. That’s why we hosted an office hour with Fearless’ COO John Foster. During this virtual event, he answered attendees’ burning questions and shared how Fearless uses strategic planning to reach their goals.
The free office hour we offer on a semi-regular basis is a great opportunity for attendees to get tips, ask questions, and learn from someone who has been successfully utilizing strategic planning for his company for many years.
What does strategic planning look like at Fearless?
When implementing a new framework like strategic planning, it can be useful to understand how other companies have successfully utilized it.
John says Fearless takes a slightly different approach to strategic planning compared to other companies. Fearless’ strategic planning includes a trimester and end-of-year planning tempo. And both of these sessions include brainstorming around what worked in the past year, what they need in the coming year, and creating outlined ideas and goals from there.
1. Tempo
Planning starts with tempo, and for the Fearless team that comes in the form of trimester planning as opposed to quarterly planning. The executive team sees this as “an intentional speed bump” that forces them to “understand what’s working and what’s not working.”
They also have an end-of-year planning session in the fall. During this the executive team discusses what they’re going to focus on in the course of the following year. However, even before this end-of-year meeting, they’ve already taken the time to outline and write down what their five year goals are.
2. Brainstorming sessions
During these trimester and end-of-year planning sessions, the Fearless team brainstorms around the questions:
- What went well in the past year?
- What do they need to do in the coming year?
These questions are purposefully high-level and allow them to focus on ideation. And no idea is wrong, so long as they move Fearless towards their five-year goals.
3. Outlining ideas and creating goals
Finally, company leadership decides, of those generated ideas, what success looks like. They also decide how they’ll measure that success. From there, they work with departments and team members to understand, operationally, how to achieve those goals over the next trimester or year.
Outlining your strategic plan
When you’re outlining your strategic plan, John says the biggest lessons he’s learned are to name the authority, ensure goals are cross-cutting, and keep it simple.
1. Name the authority
John emphasizes it’s important in strategic planning sessions to make it explicit and clear who has the final authority to make a decision.
“When you’re not clear about who has the authority to make decisions in that space, you’ll come out of the planning session with no actionable goals,” he says.
2. Make sure goals are cross-cutting
Remember that, when you talk about your goals at the highest level for the year, those initiatives need to be cross-cutting to the organization.
For example, if your goal is to improve recruiting, don’t just delegate this work to your recruiters while everyone else continues with their work as normal. By doing this, you put too much pressure on a single department or individual to move the ball.
Instead, “you have to get people to think and operate collaboratively,” says John.
3. Keep it simple
Finally, remember to keep it simple.
To do this, Fearless creates a spreadsheet and on day one of strategic planning for an upcoming year, the executive team adds as many things that didn’t go well and need to be corrected in the coming year as they can think of. From that, they’re able to see patterns very quickly and can “get to the affinity around where people feel like they need to go, strategically.”
Strategic planning tips for success
John didn’t only focus on how Fearless leverages strategic planning and how you can outline your plan. He also shared useful tips you can use to create a successful strategic plan.
Have a “dreaming session”
The first step in your strategic planning journey should be sitting down and having a “dreaming session.” And during this session, ask yourself “what will the world look like in three years or five years?”
From there, you want to take the time to name what that change looks like and to name what your goal around it looks like.
When you name your goal, make sure you’re intentional about how you measure its success. Doing this will allow you to see whether the goal makes sense or not.
And remember that not every goal and measurement needs to be quantitative, it can be qualitative. So long as you’re measuring, that’s what matters.
For more information on the power of measurable goals, John recommends the book “Measure What Matters” by John Doerr. “It’s a must for anyone who’s trying to grow and scale a company,” he says.
Begin with the end in mind
How you think about strategic planning and the constructs around it will be the same, whether you’re a one or two person company, or even if you have several hundred employees. It’s all about focusing on what you want to accomplish in the next three to five years.
And the best way to do that is to “begin with the end in mind,” as John’s college mentor used to remind him. This means that you should act as if you’re already a company with several hundred employees. This will allow you to instill habits within yourself and your company early on. And this will pay dividends down the road.
Keep it simple
If you’re just starting your business, there are probably some basic functions that you need to stand up early on. These are likely going to be strategic objectives that need to be established, understood, and measured. John’s suggestion is to include those in your strategic plan in order to help you scale and grow. And this shouldn’t just be for the sake of standing it up, but for understanding what that objective means to you over the next five years.
Lean in, even if you’re feeling uncomfortable
If you’re new to strategic planning, John’s biggest piece of advice is to “lean in, even if you’re feeling uncomfortable, or even if you feel like you lack insight or trust about what your next three to five year goals should look like.”
Because, ultimately, you’ll have to drive the alignment not just with yourself or your executive team, but with anybody else that works with you. And that includes employees, customers, and partners.
Don’t plan around the “right now”
To make sure that Fearless’ strategic plan isn’t rooted in the “right now,” John says he and the executive team “make sure that any projects and activities they do can map back into their measure of success and into the actual high-level goal that they’ve set.”
By ensuring their projects and activities are grounded in their measures of success and high-level goal, Fearless is able to plan around the future. Rather than only focusing on what’s impacting the company right now.
Fearless also only “has three priorities for the year,” says John. “And then they have a series of projects broken down for the current trimester that map towards those priorities.”
From there, the Fearless executive team:
- Names the activity,
- Names the measure of success for that activity,
- Ensures the activity maps back into the larger goal that they’re trying to accomplish.
By spending the time on these steps, you’ll see very quickly if you’ve created a strategic plan that’s rooted in the right now, or if it has successfully accounted for the future of your company.
Ask questions
It’s easy to get “analysis paralysis,” as John says, when you “can see the things that need to happen, but can’t align all the pieces fast enough to get where you need to go.”
But what do you do when that happens? John suggests you ask a lot of questions.
Whether it’s to your executive team, management, or employees at any level of the company. Asking questions of many different people helps you build the case for context.
It’s also important to remember to “lean into the idea of being uncomfortable.” Sometimes you won’t know the answer, but you’ll still have to make a decision and live with the consequences. So, “be okay with knowing that you’ll potentially do something that people may not agree with.”
But when that happens, so long as you can measure your progress and outline what your leading and lagging indicators are, you’ll be able to see if you’re doing the right thing.
Start strategic planning early
As a founder and entrepreneur, you likely have many time constraints and real operational fires that need to be put out. And with so many other things taking up your time and energy, it can be easy to put off strategic planning. But Hutch Program Manager Stephanie Chin warns against this.
“It’s often easier to start building up these behaviors when your company is small,” she says. “Getting folks aligned on a strategic plan when you’re a handful of people, is much easier than trying to get 150 employees aligned to the priorities that you set.”
This means that you should start planning early. Even if you don’t think you have the time. In the end, you’ll be glad that you did so.
Solve patterns, not problems
“It’s the responsibility of you, as the owner of your company, to solve patterns, not problems,” says John. And strategic planning gives you the space to think about the patterns you’re seeing in your organization and helps you strategically solve them.
This work is hard, as it requires you to say “even if I see a fire, it’s okay for it to burn for a little bit because I need to solve another recurring problem in the organization.” But, while it might take you several years to change the pattern that you’ve identified, ultimately, solving that pattern will get you to your goals.
Identify weaknesses
When making a strategic plan, knowing the areas you want to improve is important. These will help you create priorities and goals during your planning sessions.
The first thing John does when he wants to identify weaknesses is “talk to a lot of people inside the company.” At Fearless, this looks like company-wide meetings held every other month, barnyard chats and Q&A sessions open to everyone at Fearless, and informal 1-1 meetings.
By taking the time to talk to many different people inside your organization, you’ll get the opportunity to understand how well your people are able to communicate and internalize the direction you’re moving in. And it’s also “a mechanism for employees to be able to push back.”
Plus, being able to hear from team members in candid, direct, and open ways gives you “greater context that can be layered on top of what you’re trying to do strategically.”
The second thing he does is tell the story of Fearless to a stranger. This creates an opportunity for dialogue, and it will allow you to see what you’re doing that makes sense and what resonates. In the end, this will either be a validation that you’re doing something right, or it will flag that you’ve majorly missed something.
Strategic planning is a framework, not a roadmap
Remember, strategic planning is a framework. This means that it’s meant to help guide you, but you’ll still need to put in the work to achieve your goals.
But, even inside this framework there’s still room for creativity. In fact, “you need to be creative and you need to take risks,” says John. You shouldn’t feel like this is “a mechanism to lock down your creativity.”
“Knowing who you are, what you want to accomplish, and being open to trying new things” will allow you to approach strategic planning in the way that works best for you.
Watch part of John’s office hour to hear his strategic planning tips.
