Don't steer too far from the reality of the game
But when asked the most important training ground lesson learned so far, it is his early career at Crewe and a moment from one of the thousands of hours spent developing young players, that Holland recalls.
“I would sometimes watch the Crewe academy boys train and see lots of tricks and skills, then when I watched them play in a game on Sunday I saw nothing. There was no transfer of the training into the game.”
Although he has progressed a long way from his time with the U12s at Gresty Road, that crucial lesson has been underlined many times by the mentors he has worked with since.
“The key always with practice is the transfer into the game and all the coaches I have worked with have reiterated that point. It is important to try to maximise the possibility of a transfer by not steering too far from the reality of the game.”
Holland stresses that the content and methodology of daily practice at Chelsea’s Cobham training ground is very much guided by the manager, with his own role to support and assist.
Given he has assisted five managers in as many years it is unsurprising that he states that one of the most important skills for the modern elite first team coach is the ability to adapt.
“I’ve worked at Chelsea for five years now, for different coaches who have worked in different ways. As an assistant you always have to adapt to the needs of the manager. That is your job, to support the Head Coach.
“You need to be able to adapt to their requirements. Also at this level you are working with a very cosmopolitan mindset, not just English players. The ability to adapt to understand different cultures and communicate well is also important.”
With Chelsea’s foreign contingent boasting a number of new additions this summer, it is little surprise that Holland is currently taking three two hour Spanish Lessons a week, part of an unrelenting work schedule he describes as ‘the wheel’.
“At Chelsea you are playing more or less every three days all season long. There are a dozen European fixtures every season added to the additional fixtures that come with regularly visiting the business end of the domestic competitions.
“It’s a 60 plus game cycle that you are involved with. You finish one game and immediately you start your preparation for the next game two days later. It can be relentless, but also exciting.”
When asked to define his own personal approach to designing effective practice, Holland underlines the importance of having a clear understanding of the objectives.
"If you are training an elite team your objectives are different to developing younger players -sometimes you are trying to do both.
“In development you build your sessions to the requirements of improving the individuals. That’s the job: develop the best players, focus on playing to strengths and improve weaknesses.
“With an elite team it’s different, there are physical, tactical and technical objectives that you are trying to achieve. To transfer the physical objectives of intensity for example, the session has to flow with limited breaks.
"So you have to adapt the session accordingly with the messages incorporated in the practice, so you don’t stop the session as much. It’s more of a training session than a coaching session. In development it can be different, sometimes technical improvement is more important than physical intensity."
Holland speaks enthusiastically about letting lessons ‘run’ in order to achieve a flow to practice. Key coaching points are made before and after the practice ensuring interventions are minimal.
"Organisation is also part of letting it ‘run’. The more pitches and equipment you have available the more it can help the session to be dynamic. I believe the players enjoy this process."
Holland’s former Chelsea colleague and current Real Madrid first team coach, Paul Clement, recently described part of the approach to working with elite players as a “negotiation” calling for a “something for us and something for them” approach to designing practice.
Holland agrees, but also points to the reality of limited training pitch time during the season as an equally significant guiding factor to the content of his work.
"With any session the more the players are enjoying their work the more you will get out of them. It is important to try to find creative ways of delivering repetitive practice to stimulate the players interest, particularly when you have little time before games to prepare and need to get key tactical messages over to them during short duration sessions to prevent fatigue."
In August last year, Holland joined Gareth Southgate to work with the England U21 squad on a part-time basis. It has proved a fruitful relationship with the pair presiding over seven wins and a draw from eight qualification matches.
Holland has enjoyed his link with the national set up and refutes some of the criticism about England failing to produce forward-thinking modern coaches.
"I can think of several English coaches that have a certain level of experience and knowledge who are also creative and capable of being equally as good, if not superior, to their European counterparts. Many of them are now involved with the national set up in some capacity."
Holland who began coaching at 21 after injury brought his professional playing career to an end, would certainly fit his own description and recently shared his career pathway to aspiring coaches on the new FA Professional Coaches Award Course.
Creating more opportunities for expertise and knowledge to be shared is something he believes can only strengthen English coaching in the future.
"We have good coaches in this country, now we have to create opportunities to share ideas and experience. I remember 20 years ago watching Dave Sexton and Don Howe deliver sessions, it was inspirational. We should create those situations more often. It can only be a positive."
"I have been fortunate to have had access to some of the game’s best brains, it’s the best way to learn. Observe and adapt ideas to your own personal method and philosophy, whilst always keeping an open mind to adapt and change with time."
A meticulous student of the game with an appetite for continued learning, Holland stresses that qualifications alone will not help coaches forge their way to the top, instead pointing to the message that education sends to future employers.
"Qualifications alone won’t necessarily guarantee that you get jobs, but taking qualifications is an indication of your commitment to learn and being serious about developing yourself for a role.
"I passed my full coaching licence (UEFA A) aged 21 and have also completed the English Pro Licence and Applied Management Certificate at Warwick University. Part of that was to hold the relevant qualifications, but also it was a willingness to learn and explore what the courses could teach me.
"In the end you compile as much knowledge and experience as possible and then decide on your own way. The more knowledge you have the better equipped you should be to succeed, with hard work, of course."
Steve Holland is assistant manager for the England men's senior team.