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How to Answer with Confidence When Challenges Come Knocking


Man With Cup of Tea, Giving Thumbs Up

Have you ever notice that once you get into a groove at work, that’s when you get hit with some boring, difficult, and uninspiring project or task to manage? As soon as we start to develop momentum and hit a sweet spot, that’s always the time when change and challenges start to present themselves.

Back when I first learned about Entropy, I actively resisted the idea. I felt like with systems and processes we could conquer randomness and chaos. But, the world we all live in is random and chaotic. It takes more work to maintain systems than to revert to disorder.

So, what are we to do if we want to tackle our work in an organized, consistent manner and also prepare for unforeseen challenges that threaten to disturb our groove? Let’s figure it out.

Accept the Working Environment as It Is

Expectation management goes a long way when dealing with new challenges. We are not employed to be robots that execute programming. We are meant to tackle problems and develop sustainable solutions. So, let’s review the landscape of the working environment -


Challenges are Inevitable.

How does the saying go? The only thing certain is death and taxes. Therefore, everything else is subject to change. So, let’s tackle change for a moment. While a byproduct of change can be disruption and chaos, change also brings growth and progress. If nothing changes we couldn’t improve. So, let’s work on accepting change as a neutral part of the working environment.

Failure will Occur.

Failure cannot be avoided. While company cultures vary and some organizations are more resistant to failure than others, failure goes hand in hand with success. At best we can try to mitigate risk and quickly learn and recover whenever a failure occurs. Once we accept that failure is just another aspect of the working environment we push past the discomfort it presents.

Your Destination will be Unclear.

A lack of clarity can be one of the most frustrating aspects of getting work done. It creates anxiety and self-doubt. And, if we are not careful can even reflect poorly on the quality of our work. However, let’s take a step back. By its nature, new challenges will be unclear. It’s an opportunity to travel unprecedented waters and map what we find there. We need to seek clarity on what success looks like but not expect clarity on how to get there.

Make the Environment Bend to Your Will

A huge part of why challenges are so disruptive is also the lack of clarity in how it will fit into our already packed calendars and busy schedules. The resistance comes from the absence of a plan and often the lack of agency that comes from the disruption. So, what steps can we take to incorporate new challenges in our day to day work?


Create a Plan.

Obviously!!! But the truth is, whenever we get a mountain of a new challenge, the stress, and anxiety that it creates often results in decision paralysis. Or, we just start jumping from one random task to another to feel like we are doing “something”. However, our first step should be to map out a loose plan of attack to get a sense of the work necessary for success.


Determine the Success Criteria (before Execution).

So, now we have a plan. What next? Without alignment and concrete success criteria we are setting ourselves up to be ineffective and frustrated. Outside of our frustrations as well, we will struggle to allocate resources and collaborate if we don’t bring our colleagues on the journey we intend to go on. So, a clear success criterion, that has alignment, is crucial.

Schedule the Execution.

Again, obviously! But, decision paralysis often sets in with new challenges or we over-index on planning and avoid pulling the trigger on execution. A great way to ensure that execution isn’t delayed is to schedule your first step once you have alignment on the necessary success criteria. Try to be as clear as possible on the first action and being mindful of deadlines.

Align on Deadlines.

As far as new challenges are concerned, deadlines are crucial in dictating every aspect of execution. The plans we create, the success criteria that we align on, and the schedule we use for execution are all shaped by the amount of time we have to get the job done. Deadlines can often fall to the wayside when plans are being executed, but we need to ensure they are kept in front of mind to successfully tackle challenges.


Adjust Your Mindset to Maximize Your Outcomes

We are only human and when a large, amorphous project gets dropped into our lap, it’s easy for us to feel discouraged or even annoyed. However, if we adjust that mindset, we can leverage these challenges to drive our professional growth and even drive significant accomplishments for our organization. So, how do we approach changing our mindset to get the most out of new challenges?

Approach your Work as a Leader.

Like John C. Maxwell said, “Leadership is influence, nothing more, nothing less.” We can approach challenges in a transactional manner and simply executed what was asked of us or we can approach them as a leader and provide guidance, solutions, and clarity as a plan is executed. This is an opportunity where we can demonstrate how we show up as a leader to a broad audience.


Execute from a Position of Strength.

Often when we are faced with tasks that we aren’t particularly fond of, we may slip into complacency which will come across in our execution. However, when we demonstrate ownership and approach our work from a position of strength, this will also be observed and serves as a means to shape the perception we want to display.


Leverage Challenges for Your Professional Growth.

Hopefully, you’ve gotten feedback on your growth and development, and have clear areas to focus on. New challenges can be a fantastic way to demonstrate your improvement and mastery in these areas. You might not always get to choose what you work on but you do get to choose how you’ll get the work done.

If you have feedback that you have great organizational skills, this will be an opportunity to demonstrate that competency at a high level. If you have feedback that your communication has been unclear, now you have an opportunity to demonstrate that communication is not a limiting competency for you.


Don’t forget challenges will be all but certain. Will they disrupt your current workflow? Yes. Can those disruptions have negative impacts? Yes. But new challenges present opportunities for professional growth and advancing your organization forward. Lean into new challenges to maximize and conquer the experience!