A few weeks ago I was walking the dog together with our teenage son Boaz. At some point he mentioned that he was curious about what he would become. The conversation that followed surfaced insights that stayed with me. I will share some of them here because they are relevant for leadership and organizational development.   

Double anxious

Underneath his comment lingered an expectation of having to decide now – at age 15 – what he would ‘need to become’ later – what profession he would ‘end up’ with. Against so many unknowns, he felt anxious – in two ways. Anxious as in eager to fast-forward to a cool and rich professional future (ideally with minimal school). And he felt anxious in the sense of feeling the anxiety of having to make the right choice now.

This double anxiety in the face of uncertainty can also show up for leaders. Common responses include leaning towards rightness and control which, in turn, can produce audacious strategies, goals and consultant reports. The leader’s rush forward to bold decision-making in front of colleagues, clients, and stakeholders may nicely soothe the anxiety felt by all.  

Now, making conclusions beforehand about the best projects to be completed is not a bad idea when the challenge that is in front of you is actually fit for linear problem solving – where the past informs the future. I recently heard Dave Snowden label this approach ‘leading by conclusions’. It is a potentially risky move, however, when the challenge is complex and unpredictable – where cause and effect can only be known in hindsight. Here ‘leading by conclusions’ may well produce deliverables without results, groups feeling bogged down, gaming of reports, and numerous restarts of change initiatives when the context keeps changing.

Travel planning and Wayfinding

After the nature of my son’s curiosity became more clear, we spent a couple of minutes talking about how to be with that. Although I was not quite sure how it would land (dad doing his coaching moves), I offered the distinction between travel planning and wayfinding – one that we often use at Cultivating Leadership with our clients. It went something along these lines. 

Finding your profession with a Travel Planning approach would require you to know your ideal ‘destination-job’, then defining one or more routes, choosing one, and then staying on it for many years. We spoke about how that approach may work, or may have worked, for some people we know, but that many folks have, and will have, very different experiences. And about why the stories that people tell about their careers tend to be much more tight, compelling, and predictable than they actually are (retrospective coherence).

We then explored Wayfinding as an alternative where you set a direction instead of a destination (think picking a 100° angle out of a 360° circle). And that this becomes easier if you are clear on what you don’t want to do or cannot do (a step Boaz actually had already done). While the resulting ‘possibility space’ may still evolve over time, this insight helped us to see where he could already experiment. Where he can use the relationships that we and he have to – over time – see what resonates and what doesn’t, adjusting his course en route. 

Who knows what the future will hold for our young man. What I do know is that this brief exchange made us feel more connected and optimistic. It also helped us to requalify (not necessarily remove) the anxiousness. The walk and conversation enabled us to bend our curiosity to ‘what is trying to happen’ as opposed to making a right or wrong choice. 

The future is in the present

Creating conditions for good things to emerge when things are unpredictable is an important parenting role. One that I am learning on-the-job and that I often stumble with. I also think that, in essence, it is not too different from what leaders are called to do in times of increased uncertainty. In complexity, an approach that Snowden labels as ‘leading by options’ is more apt. Here, what projects get completed is decided in the process, not beforehand, much like wayfinding. 

One way to arrive at a good enough portfolio of projects to start with, is by paying more attention to the so-called ‘potentiality of the present’. Borrowing from a new practice called Estuarine Mapping that I recently have started to play with, this involves spending some focused time with stakeholders to create a map at the start of a big change initiative. It visualizes the ‘possible’ and the ‘what is’ as opposed to the ‘probable’ and the ‘what we should do’. Additional moves include direction setting, the creation of a portfolio of mini projects, and setting up a learning process. All these elements are aimed at de-risking the change initiative. It also is a complexity-friendly way to work with the ‘double anxiousness’ of the people involved, including my own.

What is trying to happen?

Many of society’s biggest challenges require cross boundary collaborations that are often inherently complex. We are committed to help increase the odds of success of initiatives that address these. This calls me to work more in the present, with leaders as well as the bigger systems that they are a part of. 

I have always loved using simple maps in my practice, helping clients create something intriguing and actionable about their present. The power of, for example, an Immunity to Change or Polarity map lies in the engaging process of mapping that is often both diagnostic and remedial at the same time. Amplifying this, I will continue experimenting with new practices like Estuarine Mapping in support of organizational development.  I also look forward to working more with ‘organizational ecology’ maps that quickly visualize the patterns of role-interrelatedness in human systems. 

More ease. More joy. Better relationships.