7 Questions to Ask for Strategic Planning 

Why are strategic planning sessions questions so important? Why should business leaders take the time to do strategic planning?

Knowing the direction you want to take with your business isn’t always easy. As a business owner, you’re always looking to increase your bottom line and create a more profitable enterprise. And most of the time you’ve crunched the numbers so you know the goal. Yet, year after year you either miss that goal or aren’t quite clear about how you reached it. That’s because you don’t have a strategic goal. If you don’t have a strategic plan that is realistic and practiced, you will have a harder time reaching your goals.

Of course, you want to set yourself up for a successful future, but knowing how best to achieve that long-term goal is difficult. 

As a business owner or leader, you need a roadmap for the future: a foundation to work from and an understanding of your next steps. 

And one of the best ways to make such a plan is to work with a strategic planner like Key Performance Integrators, who guides planning sessions for business leadership teams.

Here are our 7 favorite strategic questions to ask leaders.

Questions to ask for strategic planning sessions

#1 Where are you today?

Strategizing for the future of a business can be complicated, but history is a great predictor of what’s to come. You don’t have to reinvent the wheel.

For you to successfully set the foundation for your strategic planning, it’s essential to take a deep and introspective look at your company and consider several important factors. Some factors may be company initiatives, team members, processes, and technology.

Then, analyze any trends or changes you saw in your industry over the last year. 

Why? Because they will indicate trends to look for in the next few years. 

Also, to get a feel for where you are, assess any successes and areas that could be improved over the next year. 

What goals did you achieve and why? What were the opportunities, and why? 

#2 Where do you want to be 3–5 years from now?

The next question to ask yourself is, where do you want to be in three-to-five years?

Five years ahead may seem big and daunting, with its endless possibilities.

But it is actually much easier to start big and go back. You may feel like the bigger the goals; the more successful the outcome will be. What you may find is when breaking it down into smaller pieces and setting realistic expectations, a huge goal is just wishful thinking. 

Which is why it’s essential to focus on the top priority for your business — what are the most important aspects that will push you closer to success? 

It may be hard to decide, but take a step back and consider what an ideal future looks like. And keep in mind, less is more.

For example: growing by 75% in revenue or increasing your customer base by 50%. 

The most important part is to ensure that each target is achievable within five years so that you can create a focused plan tailored for achieving them. Then, once these individual shifts are implemented, you can become laser-focused on achieving your goals through your leadership team. 

#3 What is changing from this past year that makes your goal attainable?

Once you’ve established your 3–5 year goal, you will want to break that down into your yearly goals. Learn more about setting your one-year goals in my LinkedIn article. 

After you’ve identified your realistic year goal, it’s important to consider the resources you have to accomplish it. 

It could be that a single individual on your team has the knowledge, skills, and time required to make this happen — or it could be that multiple personnel are needed. Or maybe you need to hire.

When answering this question, it’s essential to recognize that most people have regular responsibilities within their roles. Determine if it is reasonable to add initiatives to their plate. They may have to give up others to make these fit. 

Beyond having the right people, think about your process, technology stack, tools, etc. 

Clarifying what resources you’ll need is crucial for setting realistic expectations for yourself and your leadership team. 

Ultimately, you want to be rock solid on what’s needed to accomplish your goal before moving forward. 

#4 What are the most important things at a company level?

Setting ambitious goals is key to getting your business off the ground. (Yes, goals can be ambitious AND realistic) The key is to identify the most important goals at the company level and keep them there.

Yet, we all know that life can be unpredictable and often throws curveballs your way. So, when should you move the goalposts? 

In reality, you don’t want to make business plans too flexible, as it’s essential to remain consistent and focused on those core objectives. 

That said, some occasions may call for a change in strategy. 

When unexpected events like turnovers or acquisitions occur, it is necessary to reassess; however, take care not to do this too often. 

Having your goals shifted constantly can be incredibly demotivating and ultimately counterproductive; instead, aim to make a shift in strategy every year.

A good plan should be enough to withstand the tests of time.

#5 How are you measuring success?

Success can be hard to measure — it’s different for everybody, and what works for one person may not work for someone else. 

That’s why having a metric to measure success is so critical; without it, it’s too easy to become confused by the goal, overwhelmed by the process, or discouraged when things don’t go as planned. 

Luckily, a tried-and-true method is designed specifically to address this issue: SMART goals. Setting specific, measurable, achievable, realistic, and timely goals makes it easy to track your progress and make small adjustments toward greater success. 

Best of all? Even small wins are still wins.

So if you’re wondering, “How exactly am I measuring success?” take a second to adjust your approach with well-defined SMART goals, and you’ll soon have your answer!

#6 Who is responsible for each goal and strategy — who will be the owners/stakeholders of these initiatives?

When it comes to achieving goals, knowing who’s responsible is essential — it’s how everyone on the team knows their roles and who to turn to for questions and feedback. 

That’s why one of the most important steps in creating a strategic plan is clarifying who will be the stakeholders or ‘owners’ of each goal.  

It should be done with thoughtfulness and intention — once these owners are chosen, they can play an integral role in every piece of the puzzle, from framing objectives, developing strategies, implementing tactics, and evaluating progress.  

Having clear ownership also helps keep everyone accountable so that efforts stay focused on results rather than spinning wheels — ultimately leading you toward success! With the right strategy in place and clear responsibility for each piece of the plan, companies can move forward with confidence!

#7 What does “done” look like?

So you’re setting out to evaluate past performance and wondering, “what does ‘done’ look like?” 

Again, using SMART goals is a great way to set benchmarks. 

Ultimately, the challenge is to define key measures that assess whether your company has determined the right goals and if you have met them.

And that’s it!

  1. Where is your business today
  2. Where do you want your business to be in 3–5 years?
  3. What is changing in your business that makes your goal attainable
  4. What are the most important things at the company level?
  5. How are you measuring success?
  6. Who is responsible for each goal?
  7. What does “done” look like?

By answering these seven questions for strategic planning, you’re well on your way to achieving your business goals.

Need help focusing on your goals?

Connect with Key Performance Integrators to learn more about how we can uniquely help your growing business achieve ​​outstanding success at scale.

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