What Could Possibly Go Wrong? If You Don’t Know, You Should.

Whether you realize it or not, there are always obstacles in some shape or form standing between you and what you want to achieve.

If obstacles didn’t exist, it would be a breeze to accomplish just about anything. Hiring (and retaining) great people, improving profitability, increasing sales, retaining customers, building the culture you want, raising capital, and creating partnerships would be easy!

Yet all of these are massively challenging to achieve. The obstacles are the challenge!

Looking through this lens, when you identify an objective to accomplish, you’re really stating that you intend to overcome the obstacles between where you sit today and where you’ll be when you’ve achieved the desired outcome.

But you and most leaders don’t typically think of it that way. You probably create a plan delineating the steps and actions needed to achieve the objective and hope these get you where you want to be, roughly on time.

“Obstacles are the challenge.”

In reality, obstacles you’ve never considered loom in front of you and your team, and you’ll need to deal with them before you can make it to the finish line. The discipline to identify and systematically solve them from the beginning is an underappreciated and little-discussed attribute of effective leaders. Incorporating potential obstacle identification into your goal planning process is one of the most important things you can do to set yourself up for success.

With that in mind, let’s consider the four most common types of potential obstacles you should be thinking about as you plan.

1. Mindset Obstacles

Whenever you’re aiming to accomplish something important, start your planning process by identifying potential obstacles of the mind: The thoughts preventing you and your people from attaining the objective. Let’s say you’re trying to reduce discounting behaviors in your sales organization. The belief system supporting discounting behaviors is a huge potential obstacle to achieving this and it’s not necessarily limited to your salespeople—everyone involved including you, sales managers, sales support staff, and your accounting team can influence the outcome. For success, everyone must believe the value of what you provide to your customers is greater than the standard asking price before you can make the change stick.

Mindset obstacles are stealthy and ubiquitous, so start with them first and be honest with yourself about which beliefs, biases, attitudes, and assumptions have the potential to delay or derail the desired outcome.

2. Structural Obstacles

Every organization has structures, processes, procedures, and systems—or lack of thereof—with potential to prevent leaders from growing their business. Your goal planning process must identify the potential structural obstacles that you’ll need to overcome to achieve the results you want. For example, one of my coaching clients has an objective to improve the profitability of their customer relationships while simultaneously maintaining an exceptional customer experience. Together, we identified a structural obstacle to achieving this: Accountability for project profitability wasn’t possible at the project manager level in the current organization structure. They’re working to solve this and several other obstacles, as they must, to achieve their goal.

Which structures, processes, procedures, or systems are potential obstacles to your objectives?

3. Knowledge & Skill Obstacles

I’ve never seen a business with a sustained growth rate that exceeds the personal growth rate of the people running it. This phenomenon sets the stage for another common potential obstacle to achievement: A lack of skills and knowledge. How many times have you tried to accomplish something you’ve never done before? Just that notion should be enough to trigger the potential obstacle warning sign! Yet I see leaders routinely and confidently charge into the unknown with a plan to build, fix, or enhance something they lack the skills and knowledge to accomplish only to be frustrated months or years down the road when they find themselves working to solve the same problem time and time again.

Sometimes you just don’t know what you don’t know, especially if you’re trying something no one on your team has accomplished before. Find the discipline to identify the skill and knowledge obstacles that could stand between you and your goals. To overcome these learning- or awareness-based obstacles, consider hiring an expert (in hindsight often the best investment my clients have ever made!), consulting with more seasoned colleagues, taking a course, or finding other credible sources of learning to close the skills and knowledge gap to accelerate your progress.

4. External Obstacles

Potential obstacles to achievement also lurk outside your organization. These external obstacles might relate to client expectations, limitations associated with suppliers (think turnaround time, pricing, or logistics), governmental regulation, acts of nature, or anything else you don’t directly control. Although not in your direct control, you likely have influence to move these potential impediments to lower downside risk. And even if you can’t exert influence—for example, preventing a hurricane from making landfall on the day your new product line ships to customers—you’ll certainly identify risks, enabling thoughtful mitigation or contingency plans.

Which external obstacles pose potential risks to your goals?

Don’t Become Blinded by the Bright Side

By now you might be tempted to think, “I’m an optimist and it seems awfully pessimistic to focus so much time and energy on obstacles. I don’t want to concentrate on what could go wrong. I’d rather power through to get things done—after all, it’s gotten me this far.”

Here’s the thing: As a leader, your job is to be neither an optimist nor a pessimist. It is to discern reality and then create the actions that yield predictable results. The pursuit of reality requires you to do the thoughtful, critical work of identifying potential obstacles before planning to achieve your goals because the only thing I can guarantee is a non-zero probability they’ll slow or derail your progress.


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Live Online Masterclass – Creating a Culture of Accountability

The best strategies and market opportunities in the world mean nothing if you’re not able to execute our plans and get things done. And yet, accountability remains a recurring, frustrating issue for business leaders around the world. Organizations with an accountable culture execute smoothly and without drama, retain high performers, and have an improved sense of collaboration, accomplishment, and fun at work.

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Expose the #1 mistake leaders make to destroy accountability and engagement

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