Questions for Scaling Your Business the Right Way

Annual planning for your business can be challenging most years, but 2020 takes it to a whole new level. It’s impossible to say what we’ll be facing next year, or when things will start to change (hopefully improve).

But that doesn’t mean the act of planning is a waste of time. In fact, those business owners who are taking the time to think through possibilities and attempting to steer are going to be MUCH better off than those who throw their hands up and just wait for the world to slap them around again. The biggest benefit from planning generally isn’t the plan itself – the biggest benefit is opening yourself up to possibilities and being ready to take advantage of situations.

But even if you accept that planning is important – where do you start?

One suggestion that we use with our clients is to start with questions. It’s a great way to get your mind moving, it stimulates curiosity and the right questions will help to steer you towards important ideas.

With that in mind, here’s a list of questions you can use for your own planning process. They won’t all apply to your situation but it’s likely these might stir up additional ideas instead. Some of these questions are tangible and pointed, some are more open-ended. I’ve broken them into categories focused on growth and scaling your business, so pick at least 2 or 3 categories that resonate with you and start from there.

*Note – if you would value additional perspective, experience and a sounding board for your planning… that’s a big part of what we do and we’d love to talk to you. Contact us and we’ll be glad to see if we can help.

Questions for Growth

The following topic areas are ones that we’ve consistently seen as key areas that need to be addressed by most businesses if they want to grow. There are lots of other topics and questions to pursue, but hopefully this is a good starting point.


One of the biggest keys to successfully scaling a business is creating repeatability in how things are done.

Are your jobs repeatable and predictable? Is every new day an adventure, or is there a pretty good chance that you know how next week is going to play out for most of your team? Hint – repeatable and predictable makes it much easier to grow.

How quickly can a new person come in and be productive in your environment? What would it take to make that easy?

Can your team mostly deliver quality outcomes with you (the owner) not being there? If not, what would it take for that to happen?

Are there documented processes and/or checklists for doing the work (that are actually used and updated)? A clever way to do this more easily is to use simple videos (from your employees phone) as a way to document what needs to be done.


One of the ‘secrets’ to having a great business is a culture of accountability across the entire team. Employees who are engaged and take ownership of outcomes – even without the owner around.

Who owns what? Are responsibilities clear to everyone? Are they written down anywhere? We strongly recommend creating and maintaining an Organizational Accountability Chart – Ask us about it and we can send you a detailed description.

Are you (as the owner) spending your time in the most productive way? There’s a big difference between busy and productive.

Are you mostly working ON the business or IN the business? Have you tracked your time?

When’s the last time you had a real vacation? (Meaning away from the office and your phone for at least a week)? What would it take to do that?


The health of your business is determined by profitability – not revenue, not growth. Finance can be a challenge for a lot of business owners, but it’s one that you need to get comfortable with.

Are you consistently making a good profit on everything you sell? Shoot for an overall profit of at least 10% – a great business will make 20% to 25%.

Are you clear on your costs and is there a good discipline for holding to budgets and estimates for the work you do? If not, what would it take to make that happen?

Are you consistently reviewing your Profit and Loss statement and looking for ways to increase your profits? When’s the last time?

Is there any possibility of creating (or improving) streams of recurring or repeatable revenue? Want a great business that’s much easier to run? Have a solid foundation of recurring revenue and life becomes MUCH easier.


Your business model is important, but your people are critical. If you get the right people almost any business can be successful. Get the wrong ones and any business can be painful (and headed towards failure).

Do you have the Right people on your team? The right people are the ones who share your values and beliefs, who want to be there and doing what they’re doing and are constantly adding value.

Does everyone on the team share your core values? Are they clear on what those are? Core values don’t have to be formal and stuffy, but they do have to be things you believe in strongly and you have to find a way to communicate them.

Knowing what you know now, would you hire everyone on your team again today? If this question makes you uncomfortable, then you probably have some opportunities to upgrade your team.

Would you describe everyone on your team as Humble, Hungry and Smart? This is a key idea from the book The Ideal Team Player by Patrick Lencioni.

Marketing and Sales

What does your pipeline look like right now? Are opportunities lined up and it’s just a matter of scheduling them, or do you need to consistently go out and find them? How could you change that?

What’s your success rate on proposals (or closing a sale)? Why? It’s easy to become complacent but improving a close rate can make a huge impact on your ability to grow.

Who is your best client (or kind of client)? What do you do to specifically go after them? It’s critical to narrow your focus (niches lead to riches).

Do you get as many referrals as you’d like? Why or why not?


It’s easy to get stuck when you think about planning – try these questions as a way to help you get moving.

What were the top 3 or 4 positive things that happened this year? Top 3 or 4 negative things? What did I learn from those things? See if you can identify any trends or strengths you can build on.

What makes next year different than last year? A stronger variation on this would be ‘How could I do 10X the profits next year?‘ It’s not always about money, but sometimes it does help to think big and break out of a pattern.

What are the top 3 to 5 things we need to do next year? Not the day to day operations or goals, but actual significant projects or changes.

Is there a clear plan and accountability for getting those 3 to 5 things done? Who? When? How? If not, you’re just kidding yourself.

How will you keep those plans on track? This is another area that we help our clients with – stuff will happen and you will get pulled away from the important work to deal with the urgent work. What will you do about it?

What questions would you ask?

Did any of these questions resonate with you? Did we miss some obvious ones? We’d love to hear from you – and you might spark ideas for others. Leave a comment below and let us know what you think.

Shawn Kinkade Kansas City Business Coach