Is it Strategic? A Free Downloadable Guide.

Are we really being strategic?

It’s a question our clients often ask. The hard truth of the matter is one of the most common pitfalls in strategic planning is not engaging your organization in consistent strategic conversations about where your organization is going and how you’re going to get there.

So much of strategy and planning is about creating your future state. The bottom line is that you need your team thinking and talking at the right level to create your organization’s future. You won’t find where you’re going by solving operational issues or in your day-to-day tactical meetings.

As practitioners and facilitators, we’ve seen our fair share of un-strategic conversations. But we’ve also seen some good ones. Some amazing ones. Some that have blown us away.

The bottom line is that we want your team to have the pivotal strategic conversations that create your future. To help you be a great facilitator and leader, we’ve pulled together a handy guide to help you understand what constitutes a great strategic conversation and we created a list of though-provoking questions that will help your team debate and discuss how to create the future of your organization.

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What’s the Difference? Diagnosing Business as Usual vs Strategic Conversations

The first step in helping your team have more strategic conversations is understanding a few fundamental and identifiable differences between operational and strategic conversations. Before you can change the behavior, it’s important to have a good understand of what each actually looks like.

Business as Usual: Improving the Current

Business as usual is exactly what it says. It’s the standard types of operational conversations your team has every day. They function as the means to operating your business and have an important place in making sure everything is running smoothly within your organization. Business as usual should cover about 80% of your standard job.

But “business as usual” conversations can easily seep into your strategic conversations, planning sessions, and strategy reviews. That’s when things go awry.

During your planning sessions or when you have high-level conversations about your future state, here are a few key conversation characteristics that are good indicators you’re having a “business as usual” discussion:

  1. Discussing operating model. If you’re talking about your operating model, standard business operations, or product/service delivery, these conversations aren’t grounded in your future state. They’re focused on your operations.
  2. Discussing how to improve “what is already in place.” Since strategic conversations are wholly focused on your future state, any discussion about improving what’s currently in place is not a strategic conversation – although these conversations are VERY IMPORTANT.
  3. Talking about topics within the “whirlwind” of your day. If a topic you’re covering in a strategic conversation can be covered in the whirlwind of your day, it doesn’t belong in a strategic conversation. Your whirlwind represents anything that can be covered in a standard business day — be that emails, calls, operational meetings (sales, marketing, development, etc.), or your daily tasks.
  4. The outcomes from your discussion topics can be measured in hard quantitative metrics. If the topic your discussing is measured in your plan with hard quantitative metrics, the focus is more operational than strategic. Outcomes like click through rates, conversion rates, and sales figures are good examples of this.

Strategic Conversations: Creating Your Future.

Strategic conversation help create your future. Period. Any successful organization needs to dedicate time, thought, and effort to dreaming up where you’ll go next. Without a strategy or vision, a “strategic” plan really just becomes an operational plan.

You should be spending about 20% of your time having these strategic conversations! As you host your conversations, here are the markers your team is thinking at the right level and helping create the lively debate and discussion that’s critical in the strategic planning and execution process:

  1. You’re discussing something not currently within your operating model. It’s easy to see when a discussion is outside of your current operations model. Your team is thinking about something new or creating something that will eventually become part of your operating model.
  2. It’s outside your “whirlwind.”  It’s something that operates outside of your day-to-day. It might cover something that keeps you up at night as a leader. Either way, the topic covers something outside of the 80% of the time you spend operating your business.
  3. The outcomes from your discussion topics can be measured in project-type metrics. Most often, strategic conversations result in initiatives or projects to implement any of the ideas your planning team might come up with. If the output from a conversation looks like a project-type metric, you’re heading in the right direction.

“Is it Strategic?” Checklist

Use these prompts in Leadership Team meetings to either evaluate if an idea is strategic OR initiate a strategic conversation. A word of caution: Not all conversations need to be strategic, but when they need to be, use these questions:


Are you talking about an idea that….

“Creates the future? Something that is new or could be?”

Think about moving the conversation from what is in play today to creating the future. Most of the time, conversations center around current operations or what is currently part of an organization’s operating model. Strategy creates the future. It requires a substantive or transformational shift from what you are doing today. Strategic thinking really makes teams “act from the future”.

Leverages mega trends in your industry or shifting customer needs?

Inspiring a strategic discussion is easy when you bring in future-looking trend data or customer data, the kind of data that initiates hard thinking about the future. We mean REALLY HARD thinking around trends we want to ignore because it is too hard — AI, AR, Robotics, you name it. What is it for your industry?  Mega trends will impact your organization whether you like it or not. Push your team to dive deep into the future so you can be proactive instead of reactive.

Doubles down on what makes your organization successful?

Business (and life) is not a zero-sum game. However, what your organization does that is unique and differentiating is critical to your long-term, sustained success. Any idea that centers around why you win or how you could win creates a sustainable competitive advantage – which is necessary for any organization to thrive.

Determines new frontiers for growth?

Strategy, at its core, is really about leveraging your organization’s competitive advantages to taking advantage of a market opportunities. Or, in plain English, where and how to grow. Leadership Teams are responsible for designing a path to continued, sustained and smart growth because growing organizations are thriving organizations. Period.

Gets your team moving where inaction is risky?

What is risky to one team is possibly not viewed as risky to another. An easy gauge is whether the issue will harm your long-term sustainability. If so, then it’s high risk because inaction will negatively impact the health of your organization (clients, staff, etc.). It is strategic and needs to be addressed.

Is ready to move forward?

Strategy is important, but implementation is where ideas turn into results. Once your team has decided to move forward on a strategic effort, use the following questions to pressure test if the idea is implementation-ready. If you can’t answer any of the below, keep talking until you can.

  1. Commitment – Do we have full organizational focus & commitment?
  2. Scalable – How will we scale the idea organization-wide?
  3. Sustainable – How will we sustain the effort and ensure it is fully operational and part of “business as usual”?

One Comment

  1. raghavan says:

    Your articles are easy to understand, they are step by step approach. a ladder to corporate growth

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