What if high performance was inevitable?
Commercial Leadership, High Performance & The Power of Environment
A Conversation with Rory Underwood MBE DL, businessman, England Rugby legend and Fast Jet pilot
There’s something deeply compelling about talking to someone who has lived high performance in three completely different worlds, in this case, international rugby, fast‑jet aviation and senior business leadership. Rory Underwood doesn’t need to claim credibility because it’s baked into his life’s story.
What I found most interesting from a learning perspective, in our conversation, wasn’t the achievements themselves, moreover it was the way he talks about them in context, team centred seemingly grounded in environment. You might reasonably expect ego to swamp the conversation given Rory is the England Rugby Team’s top Try Scorer, far from it.
And this, in essence, became the heartbeat of our discussion, high performance isn’t an individual act, it’s an environment. Commercial leadership, in Rory’s world, is simply the discipline of creating that environment.
Below is a more personal, conversational walk‑through of the insights he shared, and I have highlighted the ones that really stayed with me post conversation.
“I’ve had so many highlights…” - Career Built on Team Performance
When I asked Rory about his rugby highlights, he paused, because there were too many moments, too many stories, too many memories tied to people, places, games, pressure and context.
“I’ve had so many different highlights… first cap, second cap, first try, first hat trick, five tries against Fiji, Grand Slam 1, 2, 3, …. British Lions…”
He listed them almost reluctantly, as if reading someone else’s CV, but then he said something that revealed the real meaning behind those moments…
“My second Cap meant I wasn’t a one‑cap wonder… and I scored my first try for England.”
It wasn’t the try itself, it was more about the respect for the team around him. Every highlight he shared was wrapped in the collective of the situation, the preparation, the shared pressure and commitment to self and others.
That theme - individual excellence emerging from collective performance - is what I heard, running through everything Rory believes about leadership.
The RAF - Where Training, Debriefing and Discipline become Identity
If rugby shaped Rory’s competitive instincts, the RAF shaped his leadership DNA.
He described the military not as a fighting organisation, but as a training organisation;
“We train for war, and even when we go to war, we’re still training. When we come back, we’re debriefing to learn what we did well and did wrong, and then train again to get better.”
It’s a relentless cycle: Plan - Execute - Debrief - Improve - Repeat – Grow
Rory flew 3,000 hours in a Jet Fighter, that’s in the region of 2,000 sorties, and every single one had a debrief. Imagine, every one, that’s 2000 debriefs, not ‘feedback’ but a developmental process designed to improve performance.
“Zero (debriefs) doesn’t work… I don’t expect businesses to do it 2,000 times, but dear Lord, they need to do it more.”
This is one of the most powerful commercial lessons he teaches, that Feedback isn’t an event, for him it’s a system. And without that system, organisations simply cannot learn, adapt or become more commercial as efficiently of effectively as they could or should.
In aviation and top class sport, debriefing is non‑negotiable. In business, it seems far too optional or forgotten entirely.
I noticed also the enormous potential and value in that debriefing is often a ‘team’ activity, eg the Rugby team debriefs a game, the forwards or the backs debrief the game, where as feedback is often one to one, and the ‘team’ misses out on collective learning.
The Question that Stops Leaders in their tracks
Across rugby, aviation and business, Rory uses one question with every leader he works with.
“What are you doing to create the right environment where high performance is inevitable?”
It’s simple, its inspiring and perhaps devastating for some. Most leaders fall into one of two traps…
They think they’re creating the right environment but are unintentionally creating obstacles, or
They have no idea their behaviour is creating obstacles.
He told a story from an Gas division of a well known brand that perfectly illustrates this. A field asset manager - well‑intentioned, diligent, conscientious - asked detailed questions every Monday morning about the weekends activity. His team spent hours every weekend preparing forensic answers ‘just in case’ this manager pushed for detailed explanation.
“He (manager) was horrified… he didn’t want them to spend hours trying to solve world peace.”
The leader’s behaviour created unintentional drag and wasted time. The team’s perception amplified it, meaning the environment, not the people, was the problem.
Did he mean to cause drag? No. He thought he was providing learning
This is commercial leadership lesson here is the understanding of how behaviour shapes cost, time, focus and value and such like.
Why Organisations Struggle with Strategy (and why it matters commercially)
Rory sees a pattern in many businesses where leaders talk strategy, but very few understand it, and even fewer live it
He often asks senior teams to explain the difference between vision, mission and strategy. Fewer than 10% can do it confidently.
“Most companies’ vision and mission basically say the same thing… what’s the point?”
His explanation is refreshingly simple:
Vision = a vivid picture of success (e.g., holding the Open trophy at St Andrews).
Mission = what the organisation does.
Strategy = the plans, and plans of plans, to deliver the mission.
Without clarity, organisations default to siloed KPIs, personal successes, arse-covering, operational busyness and ‘doing what we did last year.’
This is where commerciality is likely to collapse.
If people don’t understand the North Star, they optimise for their own KPIs, not the business outcome. Rory calls this… ‘Staring at your own belly button.’
Commercial leadership requires alignment not activity.
The Squeezed Middle and the Peter Principle
Rory is blunt about why middle managers struggle….
“Every single level of management is working one level down from where they should be.”
It’s a brilliant observation, and I suspect painfully accurate in (too) businesses.
People get promoted because they’re good at the job they used to do. Not because they’re ready for the job they’re about to take on.
He contrasts this with the military model:
Officer first, specialist second. Rory trained to be a leader (officer) first before starting to fly. During is jet fighter training, he continued with officer training.
In business though its specialist first, then manager or leader training maybe… eventually… poorly…. or too late
The result? Leaders who can do the job the way they used to do it but cannot lead, align or translate strategy into action.
Commerciality requires leaders who understand context, not just tasks, and can lead (coach) others to be successful themselves.
Feedback, Debriefing and the Commercial Cost of Busyness
One of Rory’s biggest frustrations is how businesses confuse busyness with value.
“Being busy doesn’t necessarily mean contribution or added value.”
He sees the same trap in projects, teams – even boards – and businesses.
Everything becomes urgent.
Everyone has a thousand priorities.
No one has capacity
Therefore, no one stops to think, reflect or improve (debrief).
Commerciality is impossible without capacity, and capacity requires leaders to stop, debrief and learn.
This is where the RAF mindset becomes commercially priceless to businesses.
The LIFT Model - where Commercial and Culture meet
At the heart of Rory’s Wingman work is the LIFT model which is a simple but powerful yin‑yang (meaning all things in the universe exist as inseparable, opposite but complementary forces that interact to create balance), in this case meaning -
Commercial understanding
Cultural environment
You cannot have one without the other. His three pillars - Purpose, People, Process - create the conditions for commercial thinking;
Purpose , being a clear North Star that aligns decisions.
People , inc the right skills, behaviours and relationships.
Process Systems that reduce drag as organisations grow.
When these are aligned, commerciality becomes natural in the organisation. When they’re not, organisations become out of balance, reactive, siloed and inefficient, which lead to increased risk, missed opportunities, reputational damage and so forth.
To sum up - Commerciality is an Environment and not a skill
If there’s one message that I took, Rory wants leaders to hear, it’s this…. Commerciality is not about selling more. It’s about creating an environment where people understand the mission, work together and make decisions that strengthen the business.
Therefore, if I sum up his insights, commerciality is about:
Clarity
Alignment
Debriefing
Prioritisation
Trust
Shared purpose
Removing obstacles
Measuring what matters
And building teams that work with each other, not around each other.
As Rory put it….
“Otherwise people end up being too insular… staring at their own belly button rather than seeing what’s over the horizon.”
If you enjoyed this conversation about commercial leadership and high performance, you might to read the interview with Charlie Gordon on this website about commercial leadership and complexity
Photo with PJ Stevens and England Rugby Legend, top try scorer, Jet Fighter pilot and businessman, Rory Underwood MBA DL . How to build a business where high performance is inevitable.
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