How ‘Tigger’​ & ‘Eeyore’​ personality types combine in a startup team

Many startups are driven by co-creators, two entrepreneurs working in unison with joined-up thinking and ambition. They spark off each other, with complimentary skills and personalities, providing a balanced perspective on the venture – we all know about the ‘dynamic duos’ in the tech world, Hewlett & Packard, Brin & Page, Jobs & Wozniak. The individual characteristics, the chemistry and rapport behind these collaborations ensured that their talents fused to create something remarkable.

Having experienced a number of founder duos in the startups I’ve worked with, I’m intrigued as to how often one founder is full of beans, spontaneous and vocal, whilst the other is more cautious, more focused on risk, and more thoughtful – the extrovert-introvert combination is a common axis.

The terms introvert and extrovert are painted as two polarised pictures of the extremely shy and the extremely confident. The Myers-Briggs personality test marks you as an ‘E’ or ‘I’ to explain motivational and behavioural drivers. First categorised by Carl Jung in the 1920s, an introvert is commonly defined as someone who gets their energy from time spent alone rather than socialising. Unlike their extrovert counterparts (who get energy from other people), introverts are typically quieter and more observant. Almost everyone can be squeezed into one of two boxes, but it turns out that many of us are essentially ambiverts.

The contrast is often quite stark, and I now have a model – as seen in A.A. Milne’s Winning the Pooh – they are Tiggers and Eeyores. Now whilst this insight won’t get me onto the academic staff at Harvard, I think it highlights one aspect of entrepreneurial founder duos that delivers success – opposites that compliment decision making on the ‘go now, fast’ or ‘get ready first’ spectrum.

I remember when I first read A.A. Milne’s stories about Christopher Robin and his friends in 100-Acre Wood – Winnie the Pooh, Piglet, Tigger, Eeyore, Owl, Kanga, Rabbit and Roo – I couldn’t help but think how each character reminded me of someone I knew. Looking back, I think that was the beginning of my fascination with personality styles and how they orient in teams. Who would have thought that many years later I would write a personality-based blog around two of Milne’s beloved characters!

In 100-Acre Wood, they are the contrasting positive and negative thinking personalities, Tigger, that adorable tiger is seen as optimistic, full of energy – but just too much to deal with sometimes. Of course Eeyore, everyone’s favourite down in the dumps donkey with the pinned on tail, is pretty much Tigger’s complete opposite. but behind the high energy of Tigger and the gloominess of Eeyore, there are nuances we can take into a startup context.

Eeyore is the loveable, downbeat, gloomy donkey, his glass is always half-empty. He spots the dark cloud rather than the silver lining for sure. Eeyore doesn’t expect too much of himself or too many exciting things to happen, therefore remains quiet and subdued most of the time. That in no ways means he isn’t an intelligent animal, he is actually knowledgeable, but keeps himself to himself.

In your team, you can be absolutely certain that your Eeyores will find all the reasons why something won’t work. They are cautious and yet often intuitive, but they don’t speak up because they assume their contribution will be steam-rolled. You need to harness their counter-balance views in the right way, otherwise Eeyores can be very frustrating team members!

By stark contrast, Tigger – That’s T – I – Double Guh – Er! – is the alter-ego, a hyperactive, extrovert personality. He acts on impulse and will dash rather than walk, and whilst that can energise a startup, that impulsive leap and rush more often than not is jumping around without taking measure of his surroundings. This at times leads to mishaps and causes utter mayhem – not least to himself.

Tiggers are energisers, positive thinkers who love a constant challenge. They get bored easily and often half-complete stuff as their interest is distracted by a new idea. Sometimes their enthusiasm is over-powering and irritates Eeyores, so much so that they’ll probably hold more stubbornly to their opinions, and may become even more gloomy to counter-balance Tiggers’ overt positivity. Tigger is the quintessential exhuberant, positive person in the team –  but sometimes overconfident, such that he never learns from the past, and is blind to potential risks. Having said all that, Tigger is also resilient, fearless, optimistic and resourceful.

In your startup team, your biggest challenge is to keep Tiggers focussed, conscious of deadlines and mindful of the details of what they are working on. Tiggers perform well under pressure and are not easily deterred from a challenge so don’t be afraid to set them ambitious targets. Eeyores want to be more grounded and ‘realistic’, but Tiggers may find this over cautious approach negative, because they fear the downbeat emotions are catching and they dread being sucked into pessimism. Tiggers often act Tiggerish because they’re trying to keep that Tigger flame alive.

A Tigger doesn’t mind trying new things, and doesn’t fear failure. If it doesn’t work out, he will simply bounce onto the next new idea, undaunted. Balancing this, whilst Eeyore can be seen as negative, he’s actually cautious and not gullible – he won’t fall for a ‘too good to be true’ opportunity – so a good foil for a Tigger in a founder duo.

I admit when I think of them, they remind me of AI folks and bankers as the ideal partners in a Fintech venture, the co-founder duo opposites that need each other in a challenger Fintech.  Tiggers have the unbridled optimism of ‘there are no boundaries as to what we can do with data’, whilst the Eeyore banker, with the deep domain knowledge, is needed to balance and navigate a regulated industry with a reality check.

Imagine the dialogue stood next to the whiteboard in a brainstorming session. As a banker you need to step outside your comfort zone and not be too much of an Eeyore while evaluating an opportunity to deliver a new and innovative service Tigger has thrown out there. Maybe, just maybe you will stop and think…yes, maybe we can do this, we just need to step back and be more of a Tigger.

For Tigger, he needs to put the market pen down for once, stand still and listen, accepting there are boundaries to navigate and you can’t simply disrupt without thinking about a strategy, a plan and some details. Asking ‘Why not?’, challenging and listening to each other, creating a dialogue, should balance perspectives.

There is a place for Eeyores in startups, they are not just naysayers. Susan Cain changed opinions with her book Quiet: The Power of Introverts in a World That Can’t Stop Talking. Indeed introverts have emerged as leaders in every arena – one-quarter of all US Presidents – including Jefferson, Lincoln, and Barack Obama – were identified introverts of varying degree, whilst Bill Gates and Elon Musk are predominantly introverts.

A Harvard study found that, while extroverts excelled at leading passive teams (employees who simply follow commands), they were far less effective in leading ‘proactive’ teams, where everyone contributes ideas. Introverts are more effective than extroverts in leading proactive teams because they don’t feel threatened by collaborative input, are more receptive to suggestions, and listen more carefully.

The two contrasting personalities working collaboratively epitomise the old saying ‘two heads are better than one’ – so what are the principles we should look for in Eeyores and Tiggers and get the best from their two contrasting perspectives in a startup?

1.        Emotional intelligence, not emotional mastery

The better you’re able to communicate with others and form strong connections, the better you’ll navigate a startup. Successful entrepreneurs aren’t unusually cool-headed people who can contain their emotions and avoid reacting irrationally. Rather, they’ve built strong relationships with their staff and customers, and it’s those interpersonal networks that do the emotional heavy lifting when times get tough. The emotional intelligence that it takes to sustain these bonds can prove decisive, be it the energy and passion of an extrovert, or the quiet trust built by introverts.

2.        Self-reliance

If the idea of starting from scratch and having to rely on yourself frightens you, coping with the ups and downs of the startup experience might be difficult. No matter how their personalities differ, successful entrepreneurs know how to keep going despite the inevitable discomfort of going outside their comfort zones.

This doesn’t mean extroverts win through with their boundlessly self-confidence though. We tend to romanticise extroverted founders who show outsize confidence, but many in reality grapple with uncertainty internally all the time.

Successful entrepreneurs have a greater fear of being stuck in their comfort zones and not reaching their potential. It isn’t that facing ongoing uncertainty is a thrilling or threatening experience to every founder, or that every successful entrepreneur has unshakable confidence in spades. It’s that no matter what challenges come their way, they believe it’s in their own power to determine their future. That instinct for self-reliance is key, the quiet determination of Eeyores often goes unnoticed.

3.        Willingness to be wrong

This is hard for both personality types. All successful entrepreneurs are curious, constantly on the lookout for better, more efficient, productive ways of doing things. They have an underlying trait in the willingness to scrap their assumptions and test a totally different idea.

Some extroverted entrepreneurs may carry an air of certainty, but chances are they’re more willing to admit to being wrong than you might imagine. For an introvert, quiet, internal assessment and analysis enables them to come to their own conclusions, albeit from a different perspective.

4.        Trust in their intuition

Successful founders see and act on opportunities even when they don’t see the complete picture. To fill in the blanks and join the dots just enough in order to be able to act, they need to have a high level of trust in their own intuition.

It’s easy to misinterpret an introvert’s internal processing as disinterest. But in reality, most introverts are just methodical thinkers. For an extrovert, what appears to be a cavalier approach is just behaviour based on self-belief that they can get there

5.        Be radically open-minded

The biggest barriers to good decision-making are your blind spots and self doubt. Together, they make it difficult for you to objectively see what is true about you judgement and your circumstances. If you can recognise that you have blind spots and open-mindedly consider the possibility that others might see something better than you and might know the best possible path, you will deal better with ‘not knowing’.

This avoids either bluffing (the extrovert response) or doubting yourself and doing nothing – the introvert response. Triangulate your view with believable people who are willing to shape your opinions

So, if you’re startup stumbles, with panic on the streets of Carlisle, Dublin, Dundee, Humberside, don’t simply ignore the signals on the one hand and rush on like Tigger, or spiral down and convince yourself you’re doomed as Eeyore would have you believe. Don’t drink from a glass half-full of rash, unbridled optimism as feted by Tigger, or sit morosely like Eeyore with a hang-donkey expression, add a bit of balance.

Look for the opportunity in every difficulty like Tigger, instead of being paralysed at the thought of the difficulty in every opportunity, but at least make sure you ask Eeyore – fortune favours the brave and audacious, but not the foolhardy, leaping without looking. Nobody told Dick Fosbury the first time he leapt backwards, but he knew the height of the bar.

Balance is the key. AI Fintechs and bankers need each other and like Tigger and Eeyore should appreciate their differences. Also, step back and try to see things from the other’s perspective now and then. I am by nature a Tigger more than an Eeyore and yes, I do get ahead of myself at times and so I do appreciate a more level headed, grounded perspective. Eeyores help me balance the risk vs. return. Net, net, we all need a Tigger or an Eeyore to help us be our best selves.

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