Flipping Dilemmas into Opportunities

Overcoming impediments and maintaining forward momentum

Have you ever been in the process of implementing a plan and then encountered a barrier that stops you in your tracks?  These impediments delay or even sink strategy if not thoughtfully managed.  Moving forward may be as straightforward as incorporating countermeasures into your plan or there may not be an intrinsic solution.

Many times, I have seen teams walk away from great ideas because of these impasses.  But what if you could reframe the barrier in a way that offers a path forward?  That is the power of dilemma flipping, one of the more challenging skills I continue to strive to master and also one of the most rewarding.


My interpretation of what Johansen seeks to teach us is that the concept of dilemma flipping involves taking the time to understand the situation to distinguish between a problem and a dilemma, making sense of the circumstances creating the dilemma, and then reframing in an attempt to unlock possibilities for moving forward.


At the very least, it puts you and your team through the paces to make sure that you are clear on what must be true to move forward before choosing whether to throw in the towel.  I have found that individuals and teams who practice dilemma flipping also gain a secondary benefit of being much better problem solvers in the longer term.


1. Learn to differentiate between a problem and a dilemma

If a dilemma is mistaken for a problem, it can be easy to squander time, money, and resources in pursuit of trying to solve the unsolvable.  Investing energy in something that will not truly help you overcome the barriers you are facing creates distraction and ultimately leads to ineffective strategy implementation.  Asking probative questions and the “5 Whys” (see Tip #2 below) to enhance your understanding of the circumstances and variables creating the impediment is an important step in distinguishing between a problem and dilemma, the latter which has no apparent “fix”. 

2. Identify the root cause(s)

Iteratively asking “why” something is an impediment (the general rule of thumb being at least five times) will often help you get to the core, fundamental issues that are resulting in the dilemma you face.  After each answer, ask why that is the case until you can no longer answer the “why” question – this is when you have most likely arrived at the root cause upon which to focus your energy.  Sometimes you have to dig deep to get to the root cause of what is standing in your way even when it may be easier to stop short or just walk away from the dilemma.

3. Shift to a “what would have to be true” mentality

Asking the simple question of what would have to be true to move forward is a quick and highly effective way to reframe your thinking about a dilemma.  Once you understand the root cause(s) of your dilemma, you can begin to explore, with higher yield focus, which conditions, resources, and other forces need to be in play to get unstuck.  With that said, not every dilemma can be flipped into a viable opportunity in the desired time frame but the ability to set aside an idea eyes wide open and with an understanding of what would be required to move forward can be just as valuable.


Being sensitized to the difference between a problem versus a dilemma is an important first step to developing this skill.  By practicing the tips outlined in this article, you will likely begin to develop your own “hacks” for reframing dilemmas into opportunities.

For questions or to find out how EverSparq can help, contact info@eversparq.com.


Christopher Kodama

About Christopher Kodama

Dr. Kodama’s 25+ years of executive and clinical leadership encompasses guiding strategy design and implementations for start-ups and new programs, managing IT implementations, and leading cost structure improvement initiatives and turnarounds…