Let the good times roll

I once worked with a serial entrepreneur who I (openly) referred to as permanently dissatisfied. There was undoubtedly a gentle dig intended within that description, as the individual concerned could seem impossible to please, but the trait could also be a positive and powerful force for progress. Indeed, I've experienced or observed the same attitude in many disruptors, including other founders, VCs and innovative colleagues in well-established companies.

So what did I mean by 'permanently dissatisfied'? Well, at the simplest level it's how business mavericks tend to regard the world and existing ways of doing things. Whether it's an entire industry, a form of technology, a specific competitor or an existing product, being dissatisfied means having an almost unshakable belief that it can be done better. And as long as they have some good ideas and solutions up their sleeves, it's a solid launch pad for those seeking to 'shake things up'.

On a day-to-day level, however, it can show up as contempt (whether serious or lighthearted) for almost anything, from the quality of the beans being used at the local coffee shop to perceived flaws in the latest software update for an iPhone. The default setting is to question everything, sometimes including the achievements and efforts of their team. Which may sound harsh, but will be familiar to many who work, or have worked in a startup with an evangelical founder/founders.

These visionary types often demand their people question everything, think bigger, fail faster and try harder in the constant pursuit of growth and creativity. And this approach of pushing people to their limits - asking them to become the best they can be and shoot for stars - can lead to big leaps forward in short spaces of time. It can also risk 'burnout' but that's another story. In cultures where there's little fear of failure and being average at anything is unacceptable, young ventures can progress on a weekly if not daily basis - perhaps not always hitting the stars, but regularly peppering the moon.

At its best this agile, almost 'agitated' approach to business can indeed change the world - creating confidence, belief, momentum and excitement - but beware of exclusively focusing on what needs fixing, improving or beating. At its worst, this attitude can lead to a feeling that results, effort or people themselves never seem to be good enough. Never intended to be taken that way of course, but a continual feeling of 'not good enough' can be draining, demotivating and unfulfilling.

When everything can apparently be done better (which no doubt it usually can by the way), or the list of problems appears never-ending, it's too easy to forget how far you've come. The fact some things are going pretty damn well can get lost, and in more challenging times the hurdles can start to appear like they're blocking out the sun.

Particularly in larger, more complex organisations, or maturing fast-growth companies where the rate of change is slowing and the ramifications of mistakes are potentially more significant, it's still important to foster a culture of continuous improvement, also allowing people to fail and learn, but it's equally if not more important to celebrate success. Not to let everyone rest on their laurels and become complacent, but to bring some balance - to pause occasionally and remind people of the wins, progress and good news they might not have heard.

'Dissatisfaction' still has a place, but continually pointing to the multitude of problems, challenges or failures that businesses of all shapes and sizes naturally encounter can lead to a loss of confidence and morale. Once scalability and sustainability become the issue, or in the case of transformation, change or continuous improvement for bigger, well-established companies, it pays to tone down the self-criticism and point to achievements from time to time.

One of the best ways to do that is let your colleagues do the storytelling. It's easy to email out a request for good news, or comb weekly updates for the right data before reeling off a list of plus-points at the next huddle, town hall or webcast, but I'd suggest it's far more powerful to ask those delivering the goods to explain what they've done. Particularly in times of stress or change, I've seen and felt the mood of such a gathering, or rather the energy and attitude of the people within it, change dramatically after hearing about a few wins from those involved. Joining up the 'sunnier' dots can boost positivity, momentum and collaboration even in times of stormy skies.

Progress-based storytelling also helps recognise and - in a way, reward - the individuals or teams who've delivered of course, while helping their colleagues understand and appreciate what they are up to and reminding everyone in the room (real or virtual) they are on this mission together. Most importantly, it gets others thinking about what they could perhaps talk about next time, which can create a continual loop of good news and build a winning mentality. Think of it as sharing the good stuff, just as teams are often asked to share stretching goals and the pressure to reach them. If you get the balance right, everyone should feel more satisfied.