Five Pitfalls that Prevent Leaders from Dealing with Complexity

“Do not look where you fell, but where you slipped” – Proverb


The leader who can successfully navigate through complexity is a valuable asset to any organisation. Despite having to deal with high levels of uncertainty, these leaders are good decision-makers and manage to avoid many of the pitfalls that others fall foul of. They are adept at recognising complex situations and applying a range of situation-specific resources to help them to make the best decisions possible.  A key factor that sets these leaders apart is that they anticipate pitfalls and take steps to avoid them.


I’ve taken five common pitfalls that have been well documented in research and which, based on my experience as a coach, I find most prevalent when working with senior leaders and their teams. If we increase our awareness of potential pitfalls, then we have taken the first step in improving the quality of our decision-making and our ability to deal with complexity.


So, let’s dive right in:


  1. We substitute simple problems in place of more complex ones.

When faced with a complex problem we can often, unwittingly, replace it with a problem that we feel we can solve. We are prone to employ “mental short-cuts”.

For example, if we are asked to estimate how likely we are to be killed in a plane crash, instead of looking at the probabilities, we are more likely to reflect on the question “how easy is it for me to recall news items about plane crashes”, thus overestimating the probability by many orders of magnitude.

Similarly, when dealing with very complex problems, we can be tempted to over-simplify them in order to make them more rational and to feed our own sense of control over events.

One example of a simple but effective way of avoiding this pitfall is to actually work backwards from the outcome. To do this we begin by describing the desired outcome in detail – what it would be like if the problem was resolved and then work back to identify how we actually reached this point.

This tends to surface the problem that is to be resolved without having a particular path in mind beforehand. It also allows for higher levels of innovation as multiple strands may open up when working back from the outcome.


  1. We confuse understanding with predictability.

Just because we can understand how we arrived at a particular situation does not necessarily mean that we can predict the future state. Hindsight does not guarantee foresight.

If there is a clear cause-and-effect, then it’s possible to predict outcomes. But in complex situations, there may be some correlations but no clear cause and effect.

Also, what seemed to work in one context may not work in another. We see something that worked somewhere else and decide to try it here, only to find that it fails miserably. We could understand it in the original context, but could not predict how it might work in a different one.

This is very relevant in the area of organisational change. Even within a single organisation, change efforts that are successful in one part of the organisation can fail in other areas – it’s never as simple as “plug-and-play”.

Instead of assuming a clear cause and effect, it can be far more useful to ask “what is likely to happen?” and “what early indicators will tell us whether this is beginning to work?”. Introducing this shift in language from definitive predictions to emerging progress helps to shift the mindset around change.


  1. We confuse good outcomes with good decision-making.

It’s likely that you have made some poor decisions during your career. Note that I said “poor decisions” not “poor outcomes”. Whilst poor decisions generally result in poor outcomes, even good decisions can have poor outcomes at times.

It’s quite possible to have very robust decision-making that eventually ends up with a poor outcome – there is always the possibility of unexpected external factors coming into play. However, the better our decision-making the fewer bad outcomes that we should encounter. If we are to become better decision-makers, then we need to regularly review our decision-making.

Unfortunately, if we assess our decision-making purely on outcomes, we are unlikely to improve. To improve, we need to keep records of our decision-making at the time we actually make the decisions. Recording information in a decision-journal – the outline of the problem, assumptions made, variables identified, alternatives that were considered and our expected outcomes – will help when we review our outcomes at a later stage and critically examine our original decision.

Only by reflecting on our decision-making processes in a structured manner can we hope to learn. Regular reviews of decision-making can be an incredibly useful exercise for both individuals and teams.


  1. We treat confidence as an “all or nothing” measure.

When we ask someone if they are confident about something, the person often feels that they are being asked if they are 100% confident. But in a world that is unpredictable, it’s unrealistic to seek 100% assurances. Nevertheless, we fall into the trap of seeking these assurances, and also giving them when asked.

In a complex world, it serves us better to seek degrees of assurance (other than 100%) and to give more realistic estimations. So, instead of saying “I’m confident”, it might be more accurate to say “I’m 60-70% confident” acknowledging that you might actually be wrong (and, let’s face it, you will be wrong sometimes). This encourages greater honesty and acknowledgement that failure is a necessary part of success.

Making this shift in language in your team is also the first step in promoting greater levels of psychological safety around innovation and how we view failure. It also brings the conversation around to what actions can be taken to increase the level of assurance rather than to seek the 100% solution. Led from the top, this can make a powerful shift in team problem-solving and decision-making.


  1. We fail to navigate polarities.

One of the most common pitfalls I come across is when a client is looking for a clear solution to a problem when in fact there isn’t one to be found. Faced with a paradox there is a temptation to go in search of a solution when, in fact, what is needed is a means of navigating the paradox on an ongoing basis.

Take, for example, a manager who is trying to balance “task-focus” versus “people-focus”. This isn’t an either-or situation. Focussing solely on one or the other will be detrimental to longer-term success. Similarly, oscillating constantly between both results in a highly inconsistent management leadership style and de-motivated staff.

Managing this type of polarity requires us to be aware of the early warning signs that we are drifting too far towards one or other side of the polarity and to use this information to adjust course. These act like the Rumble Strips that mark the hard shoulder on motorways and alert us if we inadvertently veer towards the edge of the road.

Once we increase our awareness of these early warning signs it is possible to constantly adjust to changing circumstances, reducing the negatives from each side of the polarity while gaining the benefits from both sides of the polarity.



Often decisions have to be made with incomplete information, high levels of uncertainty, tight time constraints and competing views on what needs to be done. Under these conditions, we are particularly susceptible to relying on mental shortcuts and encountering pitfalls that will derail us.  In such complex situations, we need to be aware of potential pitfalls that may befall us and take actions to avoid or overcome them. Whilst not a comprehensive list, the pitfalls in this article are relatively common and, armed with a certain amount of awareness, can be avoided. Be careful out there!


This blog is based upon the presentation that Billy Byrne of KinchLyons gave at the EMCC National Conference in Dublin in October 2019.


Further Reading:

  • Thinking Fast and Slow: Daniel Kahneman
  • Thinking in Bets: Annie Duke
  • Simple Habits for Complex Times: Jennifer Garvey Berger & Keith Johnson
  • Predictably Irrational: Dan Ariely
  • Strategic Management and Organisational Dynamics: Ralph D Stacey

Relevant Assessments: