Navigating the messy middle

Culture  Leadership
15 April, 2019

Endure valleys and optimise peaks during the turbulent middle phase of your bold new venture

I was recently discussing the progress on one of our acquisitions, that was going through an exciting though complex transformation. The team had initially been feeling charged up and enthusiastic. However, as the team began encountering roadblocks, the high energy began waning. While a lot of great work was being done, they were feeling discouraged by not seeing quick results.

This is quite common. Most initiatives start on a high note. However, many of us find it challenging to sustain the momentum and navigate the inevitable highs and lows. The Messy Middle by Scott Belsky, who is currently Chief Product Officer at Adobe, provides great insights on traversing the hardest part of any initiative.

Belsky, who has been in the entrepreneurial world since 2005, is frustrated by the obsession with beginnings and endings – while glossing over what happens in between.

Fresh starts are joyful and inspiring, while conclusions are deeply satisfying. But what about the middle? This is the most crucial part of any creation or turnaround journey, yet it hardly gets any talk-time – because it’s also the toughest and most frustrating.

People don’t like to dwell on their struggles, self-doubts and failures because it isn’t “sexy” and it hurts their egos. So, you get a drastically edited success story, explains Belsky, which leaves out “everything important”.

With the spotlight exclusively on starts and finishes, the insights of the middle remain hidden, creating a lot of misunderstanding around this stage. As Belsky notes:

No matter what it is you’re trying to create or transform, the myth of a successful journey is that it starts with an idea, followed by a ton of hardship, and then a gradual and linear rise to the finish line. But no extraordinary journey is linear. In reality, the middle is extraordinarily volatile — a continuous sequence of ups and downs, flush with uncertainty and struggle.

So, this week, my message focuses on some of Belsky’s key insights on the messy middle. How can we navigate this challenging period of any bold new project? How can we survive and thrive, once the initial excitement dies down and the end is nowhere in sight?

When a business is creating new value – which is what we’re trying to do – the middle is going to be turbulent. Without volatility, nothing new ever gets done. As Belsky explains, we need to endure the valleys and optimise the peaks. The aim is to achieve upward momentum within the volatility: every succeeding valley should be a little less low, and every subsequent peak should be a little bit higher.

Endure the valleys

The middle miles are going to be full of lows: uncertainty, crises and poor decisions. You need to create renewable energy and patience to deal with long haul. Plus, you must learn to look failure in the eye and learn from it.

Here are three key recommendations to build endurance:

1. Short circuit your reward system

Progress is one of the greatest sources of motivation – however, the middle doesn’t offer progress in the traditional sense. The journey is tough and long, and whatever gains you make are mostly unrecognised outside of your team. Conventional metrics aren’t helpful because you’re still in the early stages. How, then, do you keep yourself and your team motivated? Belsky advises leaders to manufacture milestones and, hence, motivation.

Short-term celebrations don’t just boost the feel-good factor; they also contribute to repeated success. In Why Our Brains Like Short-Term Goals, Monica Mehta explains the role of brain chemistry:

The more times you succeed at something, the longer your brain stores the information that allowed you to do so well in the first place. That’s because with each success, our brain releases a chemical called dopamine. When dopamine flows into the brain’s reward pathway (the part responsible for pleasure, learning and motivation), we not only feel greater concentration but are inspired to re-experience the activity that caused the chemical release in the first place.

In the messy middle, broaden your definition of a “win”. Don’t limit yourself to big goals; celebrate small successes with gusto as well – whether it’s getting a new customer, or finally nailing a niggling little problem. While the wins can be granular, make sure they genuinely reflect impact – otherwise they become misleading “false positives”.

2. Investigate hard truths

Motivation is crucial during the middle period, but so is truth-telling. So many ventures seem to be going just great, right up until the point that they fail – this is because their leaders prioritise false positives over hard truths.

As Belsky explains, positivity and encouragement shouldn’t come at the expense of objectivity. Analyse what’s going wrong so you can derive its lessons and work towards failing a little better next time. Belsky recommends structured time for focusing on hard truths:

In a journey that is so reliant on positive energy and hope, it is vitally important to make consistent time and space where people can focus on what isn’t working. Perhaps it is a regularly scheduled monthly meeting, or a period during an off-site meeting when the team is encouraged to share their doubts.

3. Nourish patience

Millions of people have great, potentially game-changing ideas. But only a handful have the patience to realise their vision. Humans (and companies!) are naturally impatient, looking for quick results and short-term metrics – even when they’re invested in long-term goals. When these don’t materialise, they lose their resolve and give up halfway.

 As leaders, we need to cultivate a culture of patience for the middle miles – this will allow our exciting new ventures to ultimately be successful. Google does this structurally, by separating innovative initiatives from their core business and freeing them from the constraints of delivering near-term results. Playing the long game means we need to rethink the way we assess progress. In Belsky’s words:

Designing the structure of a project or company to foster patience is ultimately an effort to limit our natural tendency to obsess over measuring progress with traditional near-term measures. Patience doesn’t mean tolerating inaction or slower progress: It means allowing alternative forms of measuring the impact of action.

Optimise the peaks

The middle also produces highs – from wins that make you want to pop champagne, to habits or choices that lead to surprisingly good results. In order to capitalise on these victories, you need to relentlessly improve your processes as well as your decision-making. You can also strengthen team culture to carry you through the turbulence.

Here are three key recommendations to enhance optimisation:

1. Build resourcefulness

As your plans progress, you’ll be tempted to hire more people. While this can be a good thing, it shouldn’t happen at the cost of resourcefulness – which is your key competitive advantage in a path-breaking initiative. Growing the team isn’t always the path to greater success; in fact, a sudden influx of resources can actually curtail innovation. Belsky highlights a great mantra from his Head of Operations at Behance:

“Refactor, refactor, then hire,” he’d say. Teams would come into meetings with a list of positions they wanted to hire for but leave the meeting with a list of process improvements they could make with their existing team.

Before you add fresh resources, optimise for efficiency. Look at the tools and processes you’re using: What’s working well? What isn’t? What can you do differently? Uncover inefficiencies, and experiment with creative solutions. Use the lessons you learn to improve continually. As Belsky notes:

Resources come and go, but resourcefulness is a muscle that kicks in throughout the life cycle of any business.

2. Lead with conviction

For ground-breaking ventures to succeed, decisiveness is crucial. The middle miles of your creation or transformation journey will be extremely uncertain and anxious. In these unique circumstances, consensus building is likely to result in watered-down decisions – which is exactly the opposite of what you need. The role of a leader is to make the best choices, based on the strength of their conviction.

Of course, this doesn’t mean you don’t get any input from your team. Tap their knowledge to expand your understanding. But once you’ve done that, don’t avoid making a decision or look for group support. Value conviction over consensus, and make your choice. Yes, this carries some risk – but without it, no new value can be created.

3. Foster storytelling

During this rollercoaster phase, telling stories might seem like a waste of valuable time. But nothing could be farther from the truth! Belsky describes the critical value of storytelling in building a culture that keeps the team going:

The stories a team recalls and shares about itself serve as a continual reminder for everyone of why they’re there and what makes the team special…. They orient new employees and provide institutional knowledge. Even amid long periods of ambiguity and uncertainty, a healthy culture built on stories provides the context and comfort everyone needs to stick together and keep moving forward.

So, take the time to tell and retell stories that capture the uniqueness of your venture. Go back to the early days: How did inspiration strike? What shaped your vision? What obstacles did you have to overcome? When story-making moments come along – a bet, a challenge, an adventure, a victory – don’t shut them down! Welcome them, and be present for them. Let your team members forge their own amazing stories for times to come.

I’m sure that many of you would have experiences to share from your own explorations of the “messy middle”.


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