The Expectation of Winning

Everybody likes to win. And while you undoubtedly learn much about your skills, attributes and character from losses, there’s nothing quite like that sense of satisfaction when your team secures a hard earned victory.

I’ve been fortunate, both as an individual contributor and as part of a team to have racked up some important wins (jobs, promotions, new business and awards), but in truth, there’s only been three periods where I’ve been part of teams where there’s been an expectation of winning.

Expectation of Winning

Teams that expect to win are unlike anything else. By definition, winning organisations are the rarest of beasts (there can only ever be one winner), but in addition to their talent, successful teams possess an exceptional work ethic, the highest standards, unshakable confidence, and a determination that literally sets them apart from the competition.

Winning teams breathe rarefied air and there’s something special about them - magical almost. Those doing the work are obviously talented, but it’s often the management which are responsible for creating the environment for people to thrive. The best organisations have leaders with an uncanny habit of getting the best out of their team, but also the ability to attract, develop and retain talent. Seemingly, once you manage to crack the winning formula, you then create a level of momentum, which garners attention and builds a reputation – all of which combines to keep that winning sequence going. It’s not for nothing people say, “success breeds success”.

In my experience successful teams also have an uncommon bias for action, hold each other accountable and are remarkably consistent in their work. Indeed, winning teams recognise the importance of consistently high performance - and that you’re only as good as your last match, deal, or quarter, and that you must show up, time and time again. This grittiness and the ability grind out results, often in the face of adversity is one of the hallmarks of a winning team.

I’m fascinated by winning teams and the values, structure and organisation which bind them. It’s rare for a winning organisation to be thrown together – when you look, and I mean, really look under the surface there’s often a leader with a clear vision, a strong culture and set of shared values within the team. Successful leaders are very deliberate about these components and when you combine that with talented individuals, you have the building blocks of a successful team. But that’s only the start.

Winning teams I’ve been part of
How winning teams are constructed is timely, as in my role leading sales enablement at Automation Anywhere, shortly we’ll be growing the team, and I want to be thoughtful about the work we do, the candidates we hire and the culture we foster on what we hope and expect to be a winning team.

As previously mentioned, I’ve been privileged to have played a small part in some winning organisations – these experiences have taught me a lot, and undoubtedly shape my leadership style. The next few paragraphs hone in on these experiences – you’ll have to both excuse and indulge me a little, but they provide an important frame of reference for how I perceive “winning”.

The first truly successful team that I was part, happened during my teenage years, when I played for an all-conquering football (soccer) team. In fact, during an eight week period one summer, I won more trophies than in my previous eight years, such were the team’s numerous skills and talents.

And then as a graduate, I was part of a tremendously successful team at Edelman, the world’s largest public relations (PR) agency - and now first billion dollar agency. There was a 12 month period where our Edelman team won every pitch and candidly, it felt like they swept all before them. There was a strong desire and expectation to win. And more recently, I worked at HubSpot during a period of hypergrowth, where we won the battle to conquer the marketing software space, as well as launched new and exciting sales, CRM and services products. During this period we broke all sorts of records, created HubSpot history and won market share.

While it may seem fanciful (I did say you’ll have to indulge me) to talk about a junior sports team in the same breath as billion dollar companies, I’m a firm believer that parallels can be drawn between different areas and lessons learnt. For instance, at my football team, Edelaman and HubSpot there was the expectation that we would work hard, leverage our talents to the full and perhaps most importantly, continually seek to improve performance. These teams set out to win their respective leagues and markets, and were successful in achieving that.

I’ve also worked in other businesses that would consider themselves successful, even though they didn’t win their respective markets. Chill Insurance is a challenger brand that innovated, disrupted and ultimately, took market share off slower moving incumbents. While, another former employer became the world’s de facto job search engine and stole the lunch of many job boards along the way. However, is still some way off displacing LinkedIn – and the recruitment space is only going to get more competitive and exciting now Google has entered the fray.

The characteristic of winning teams
When I draw upon my own experiences of winning teams, it’s clear they all share some key characteristics. They are:

1. Talent
This may seem obvious, but it still needs to be said. All the high performing and successful teams I’ve been part of, have been packed full of talented people. While there may have been star players on each team, even the weakest players were strong. This meant that the average ability was always high - and thanks to the effective recruitment strategies that these organisations employed, there was always a conveyor belt of talent available.

2. Growth mindset
The most successful people I’ve worked with or played alongside never rest on their laurels. They want to be the best in their respective role, stay in that coveted top position and actively take ownership of their growth. These people have the potential and will to improve, and are proactive about it. They are purposeful when it comes to self-improvement and carve out and protect time dedicated to it. The lesson here is to recruit people not only for the job they’ll do today, but for tomorrow and beyond.

3. Discipline
One of the most undervalued attributes of high performing teams is discipline - top teams are extremely disciplined and keep high standards in how they approach their work. It could be arriving early to a training session, having a keen eye for the smallest of details or hitting monthly goals. Disciplined teams work hard for each other to “get shit done” and they execute on the basics consistently, and to the highest standards. They also share a level of pride in the work and are disciplined about maintaining high standards.

4. Consistency
A natural outcome of discipline is consistency. If you have the discipline to put the hours in (and of course, the required talent) it stands to reason that you’ll see improved and consistent results. The best teams, whether they be sporting or within the software as a service (SaaS) industry have high standards and consistently meet them. They’re on top form most of the time and winning is their default setting.

Top teams recognise that to win and perform at the top level they need to put in the “reps and sets”. To be absolutely clear, doing the same activity over and over again is often tough, boring, unsexy or a combination of all three – and that’s why discipline is so crucial.

5. Fight
There’s nothing quite like it when you have a team all pulling in the same direction and fighting for, rather than with each other (I’ve experienced both scenarios). Losing upsets winning teams, offends them even, and they want to go about setting it right. Immediately. In my experience the most successful teams have a squad of people who all have each other’s back – they are willing to go the extra mile to help each other out. Be warned though - it’s rare to work in that kind of environment, but when you do, cherish it – you’re onto something special.

How winning teams are led
When I think back to the winning teams I’ve been on, there was always an effective leader behind the scenes, who created an environment for us to grow and thrive. There were many similarities in how these teams were led and structured, and I’ve listed the most important below:

1. Freedom
The best leaders give their teams the freedom to express themselves and come up with the goods. They do this by giving clear instruction and direction (strategy) on what the expected outcome should be - and then let the person figure out how to achieve it (tactics) or provide coaching when it’s needed. By giving freedom, leaders avoid micromanagement, show a high level of trust and give people the opportunity to let their creative sparks fly.

2. Accountability
High performing teams are made up of people who hold themselves and their colleagues accountable. This means speaking up when something is not right or when standards slip, as well as providing constructive, but candid feedback - and expecting the same from others. Creating a truly accountable organisation is easy to talk about, but in practise, it’s hard to implement.

It’s often overlooked, but if you truly value freedom and want autonomy in your role, then you need to display accountability and take responsibility. Freedom comes as a result of accountability - you can’t have one without the other.  It took me a while to learn and appreciate this lesson.

3. Vision
The most effective leaders craft and share a vision for their team that is easily understood. They articulate this vision, work to gain buy-in and repeat the vision frequently, so people are left in no doubt what direction the team is heading in. For the most part, leaders of winning teams are skilled communicators and have the ability to paint a picture of the organisation’s future state, which people both believe in and want to be part of.

4. Culture
The importance of culture and culture-fit cannot be overlooked. While you obviously want to avoid Groupthink or creating a monoculture, you do want to be deliberate in establishing principles and norms for how you’ll work and what your organisation’s values will be. The key takeaway here is to aim for diversity in all its various forms - background, thought, personality and more, but gain alignment and understanding on how work will be done.

I would go as far to say that a strong culture is essential for high performing teams and can be a competitive advantage, which is hard to replicate. While my football team and Edelman had high hiring bars, HubSpot went a step further and codified what it looked for in its employees (HubSpot hires for HEART - people that are humble, empathetic, adaptable, remarkable and transparent). It was a bold move, but it has paid HubSpot back in spades.

5. Humility
Top teams have a healthy respect for the competition. From not disparaging the competition in a sales pitch to shaking hands after a match to being gracious in defeat, it’s important to retain a high level of humility at all times. Some of the best advice I ever received on this topic was to, “watch, but don’t fear the competition”. Instead, you should understand the strengths and merits of the competition, and use this as motivation to get and stay ahead of the them.

Winning teams possess what I consider to be a healthy paranoia and appreciate that what they have today, could be gone tomorrow – that sense of fear is what (partly) feeds their discipline.

There you have it. I’ve been thinking for some time about the winning teams I’ve been part of and just what made them so successful, and I’m pleased to have finally organised and synthesised my thoughts. By digging into the teams’ characteristics and distilling them in this way, I hope it makes them more applicable, replicable and valuable.

But here’s the thing - writing about winning is the easy part, the real challenge is doing it, and doing it consistently. That takes all the characteristics I’ve written about and some more. However, if I were to pick one attribute of a winning team it would be the ability to execute on strategy – the best teams have a narrow gap between strategy and tactics. Talk (or should that be typing) is cheap – action, delivery and results is what matters most.