Why Thinking Ahead is Overrated

“Let me think about it” would have been my usual response. Instead, I found myself promising, “Sure we can start in 4 weeks”. 

This was back in 2018. I left the meeting with my newly signed client, fully aware that my fledgling business lacked the right leader for this project. The conservative approach would have dictated identifying the project lead first, but that came with the risk of losing out to a more nimble competitor. Somehow, with the impetus of  a ready project and revenue, I trusted myself to find the right person and make it happen.

Necessity is the mother of somehow-get-it-done

By the time the project kicked off in four weeks, my new hire – call him Naveen – had flown to the client’s location, ready to go. He and I met in person for the first time the evening before project kickoff. We were introduced in the preceding weeks by a common contact – one of several I had reached out to as I scrambled to meet my commitment – and got to know each other over a few Zoom conversations. 

These conversations were not interviews for either of us in the traditional sense (Naveen was assessing me too). Having understood each other’s backgrounds and a sketch of our life stories, we quickly got down to working together, as a mini test for what lay ahead. As we collaborated on project planning, we got a better understanding of each other’s capabilities and styles. This was assessment by real-world doing, not by hypothetical conversation.

By the time we met, I had gained some confidence in our upcoming collaboration. And what if it didn’t work out? I would cross that proverbial bridge at the appropriate time. There was little to be gained by thinking too far ahead, when the only way to truly find out was to get down to work.

The ‘interview’ continues…

The project itself served as another round of mutual assessment. I had not hired Naveen into a permanent role with any guarantees; nor had he committed to working exclusively with me. The opportunity cost of commitment was high for both. It made sense to keep collaborating and assessing as we went along.

The four-month project generated a large return-on-investment for the client. Not everything went smoothly, as we disagreed and faltered from time to time. But we learned from those situations about each other’s capabilities, resilience and adaptability. Others were brought into the project on a similar try-before-you-buy basis, with emerging and dynamic situations, rather than poorly predictive interviews, as the basis for assessment.

This method has become a template for how people start at Indiginus, in stark contrast to the traditional process in most companies . We lock in revenue before locking in all resources. Company and new-hire try each other out by working together, rather than going through an extensive interview process. We evaluate, learn, adapt and re-evaluate in the always evolving present, rather than trying to predict the future from a static vantage point.

Experimentation and career decisions

This way of hiring through experimentation – based on ‘lean startup’ principles –  got me thinking about how people make career decisions – particularly early in their careers when they are trying to discover that elusive passion, but also mid-career when the realisation hits for many that their work brings them little joy.

Having acquired some grey hair, and lost some altogether, I am approached from time to time by early to mid-career folks who find themselves at a crossroads, unsure of which path to take. 

“I need to think hard and long about my next steps” is the usual sentiment, as they struggle to create a thought-through mental map for the evolution of the next 10 to 15 years of their career. Everything feels at stake with their next move, often leading to months of paralysis. Instead, I advise them to think a little less, and try a few different things out.

This experimentation-based approach to self-discovery was taken by none other than Oprah early in her career, and is one that she advocates for others. Her approach can be summarised as: try something, see what works for you or doesn’t, and make the “next right move” through a process of learning from failure. Eventually you will land on something that feels right.

The problem with thinking ahead

With time, we gather experiences and relationships. We tackle unanticipated situations and in doing so, acquire new learnings and greater self-awareness. Not only are the situations we encounter new and unpredictable, we ourselves are not the same person that started the journey.

A theoretical exercise of thinking ahead stretches our imagination beyond its capabilities. It demands clairvoyance in a dynamic world influenced by countless variables – a key one being our own evolving self. Trying to map a definitive course for one’s life and life’s work is akin to solving a human problem by pretending it bears the characteristics of a deterministic mathematics equation.

Experimentation is practical simulation, not theoretical scenario planning. It encounters and overcomes real obstacles while, in contrast, thinking ahead discourages the first step by envisioning future problems that may never come to pass. Experimentation demands short-term ‘pilots’, with failure providing welcome data for the next chosen path. Thinking ahead demands longer-term commitment, with failure leaving diminished self-esteem and a lack of direction in its wake. In a real-world situation, we can be surprised by our love for something we had never envisioned, or our unexpected resourcefulness in difficult situations. Thinking ahead leaves no room for such surprises.

A new model for individuals and organisations

I am not advocating random experimentation. We must narrow down our choices – I call these reasoned hypotheses – based on what we know today about ourselves, the world around us and practical constraints. But from that point forward, acting, learning and adapting – particularly in a world that throws up surprises faster than ever – is the method that will propel us towards our calling.

This approach demands not only flexibility and risk-taking from individuals, but also from organisations and hiring managers. But in the end, if experimentation results in a suitable match, or confirms the opposite,  it should be welcomed by both sides. The alternative is unproductive misfits in unhappy situations – as is often the case today.

There are versions of this approach that have been advocated and tried – sometimes referred to as ‘hire slow, fire fast’, which I would further modify as ‘hire slow, fire or quit fast’.

The pejorative remark ‘she was at her last company for only 3 months’ may well be a compliment for someone keen to find purposeful and engaging work. Give her 3 months at your own organisation, by giving hiring-by-experimentation a try. If it doesn’t work out, do the right thing by helping her find, in Oprah’s words, “the next right move”. The world, and your organisation, can do with happier and more engaged people at work.

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