Strategic Planning: From lost in the forest to set on the path

Guest post by Eric Rieger, Founder/President at WEBIT Services, Inc

This is a heavy subject I will admit. For years we struggled with strategic planning internally. As a technology solutions provider where things can change at a moment’s notice, a 5-year plan can feel like throwing darts at a board or predicting what the weather will be like 3 weeks from now.

But if you do not plan, your company can veer slightly off course a day, week, or month at a time, and suddenly you’ll look up and see that you’re hundreds of miles from your original destination.

If you want to stay the course, you need the right team in place –including both internal stakeholders and external partners – and you need to ask yourself the right questions.

Who should be involved in strategic planning?

First, assemble the right people. Every department in your organization has a role to play in your strategic planning and should have a seat at the table. Those seats can be filled by managers as well as key employees who you feel can contribute to the process. Your planning group should also include:

• People affected by the strategic plan (clients or users)
• Those responsible for managing the plan’s implementation
• Outside partners with experience and insights that can help you (industry colleagues, community organizations, tech advisors)

What questions should you ask during strategic planning?

Second, you need to ask the right questions. Good planning starts with information gathering. The main questions to ask your strategic planning group can be boiled down to:

• Where are we now?
• Where are we going?
• How will we get there?

Take the time to really reflect on these questions and be brutally honest in your answers.

A strategic advisor: the secret to success

Even with all the collective knowledge inside your company, you won’t know every answer or even every question you should ask. That’s where a strategic advisor comes in. But not just any strategic advisor. You want one who understands your technology – and I’m not just saying that because I founded an IT company.

Think about it. Technology is entwined with almost every aspect of your organization – from communication, to service delivery, to day-to-day operations. It’s also one of the biggest investments a company makes year in and year out. So it makes sense that IT and strategic planning should go hand-in-hand.

Eric Rieger, founder and president, webit

If you want to ensure your IT can enable your strategic goals while enjoying a great return on your technology investment, partner with an IT strategic advisor.

Managed IT providers that deliver partially or completely outsourced IT services are where you’ll find some of the best strategic advisors. Look for a managed IT company that puts an emphasis on strategy, planning, and education. They are the ones who’ll have a strong team of advisors to help you.

How an IT strategic advisor can help you

A good advisor will want to know about your whole business, not just the parts that involve technology. We have a saying in our company: “Accurate data makes better decisions.” The only way to get the most accurate data is to ask a lot of questions about your organization’s current situation as well as your future plans.

As part of our Technology Business Review process, we start by asking our clients questions about the way they make and spend money. We got this idea from a book called Business Model Generation. The concept of a Business Model Canvas is available online:

As you can see from the diagram, the Business Model Canvas looks at the entire business and its key elements, partnerships, cost structures, and revenue streams. For a lot of our clients, this is the first time they are being asked to look at their business under this kind of microscope.

It is important for IT to have a seat at the table when it comes to overall strategic planning. Anyone can come in and create an asset lifecycle document (i.e., replace these 10 machines in three years, etc.), but when you factor in the elements of the Business Model Canvas along with organizational goals and objectives, it changes the way the IT strategic advisor looks at the business and the recommendations that are made.

Strategic Planning Example

Let’s look at one example. Company A has 50 employees and 2 locations, both in the Midwest. Their infrastructure is due for a refresh, and they want to be advised on whether they should keep their servers in-house or move to the cloud. A typical IT company will look at the current data usage, how it has grown over the past few years and do a couple of calculations, and then provide a proposal for new hardware and for the same environment in the cloud. In this scenario, features and benefits of each model would be discussed, and the client would choose one of the two options to invest in based on those discussions.

Here’s where things can go off the rails quickly. If the IT strategic advisor does not have a clear picture of the company’s 1-,3-, and 5-year plans, there’s a better-than-average chance that regardless of which option the client chooses, it will not be sufficient for the full anticipated lifecycle of that product or service. Suppose Company A has expansion or acquisition plans 12-24 months down the road that would equate to an employee head count increase from 50 to almost 90.

Or suppose there are plans to open 3 more locations in geographically diverse areas around the globe. Or perhaps there are plans to create 6 new products or lines of revenue that would be heavily dependent on technology. What if there is an option to shift the company from a legacy piece of software to a SaaS (Software-as-a-Service) model that requires less or no infrastructure to support it?

How would all these data points impact the current IT recommendations?

Another question to ask is: has the entire current technology spend been reviewed as part of this process to see if there could be consolidation options or efficiency gains elsewhere?

As you can see, your IT has a lot more to do with your strategic planning than you might have realized. That’s why you need to involve a knowledgeable advisor. A true partner will ask tough questions and even press you to think about things in a way that you have not before. They will get to know your business and your industry so they can make thorough recommendations for the company’s decision-makers.

Eric Rieger, Founder/President at WebIT Services

What Next?

Strategic planning can be tough at times, but with the right people in your corner asking the right questions, you’ll come out of it stronger and ready to take on the future. If you’re struggling with your planning, the Webit Services team can help you get on track. Visit us at