Leadership Lessons from Route 66 (Pt. 1)

September 27th, 2013 by Martin Smith Leave a reply »

Leadership Lessons

This blog entry is based around some leadership lessons that I drew from a trip across America via Route 66 earlier this year. We travelled the whole Route from Chicago, Illinois to Los Angeles, California. It had been an ambition for a while and we wanted to do it the proper way, on a Harley Davidson motorcycle. We made the trip as part of a group in an organised tour run by Eaglerider in the USA.


This is a two part blog with 5 Leadership lessons in each one. The second one can be found here.



Our fellow travellers were an international bunch from the UK, Australia, Italy, Spain, Germany and Switzerland. Accompanying us on the trip were our 2 guides, ‘Preacher’ (Mike) and his Wife ‘Lala’ (Laura) and our support vehicles (to transport our luggage and a spare bikes) were driven by Matt, Geoff, and Tim.


As we were such a large group (there were over 40 of us doing the tour, a total of 27 bikes), we were organised into two riding groups who would ride together each day – each group with a guide and support vehicle. As well as transporting our luggage each day, the support vehicles would travel behind each group throughout the day, ensuring that no-one got lost or left behind. It was extremely well organised and operated. We saw and experienced many things on our journey, not only the weather, but some truly amazing sights, sounds, smells (dead Armadillo’s smell awful bad!!) and met some wonderful people along our journey.


So how did I draw Leadership Lessons out of this experience you may well ask? Well, being a management trainer and coach I try to look for learning in everything that I do and everywhere that I go. Our Route 66 experience was literally ‘littered’ with them, from the people that have helped the Route to survive and prosper, and the people who fought and in some cases continue to fight to have their town, city or attraction listed as a Route 66 Historic monument. However it is our guides and support teams on our journey that I want to focus on today for they were truly inspirational….. 


Here are the first Five leadership lessons that I experienced during our trip;


1. Start with the end in mind! – Or know your objective Leadership Lessons


In our case, without knowing where we were heading we could simply have continued aimlessly riding round America. Not a bad thing you might say, but in my view it’s much better if you have a final destination or goal. With a goal to focus on you have a direction in which to travel.

It’s the same in business, knowing what you want to achieve (specifically) enables you to set a direction and a path to start to follow, to lay out plans to enable you to meet your objectives or goals.


How clear are your goals? Are they specific enough? Do they inspire you to achieve them?

2. Make sure the team know the goal and buy-in to it! Management & Leadership Development in Sussex


Not only did we have an overall objective of covering the 2500 miles of Route 66, this big picture was broken down into a series of daily objectives.


Using this as a metaphor for business is easy. Once you have identified (Visualised) your goal(s), you can then start to plot the specific steps that will enable you to achieve it, i.e. a plan. The important thing about having goals and plans, especially when working with a team, is that everyone knows and buy’s into then, understands them and believes in them.


How well do you and your team know your plan? Do you have a plan? Do you discuss it regularly and review your progress against it?


3. Know what tools and equipment you have available Management & Leadership Development in Sussex

(skills, knowledge and experience in business terms)


The metaphor here was riding an unfamiliar bike. I don’t ride a Harley at home so I needed to listen to the briefing from the hire shop to make sure that I understood how to ride it and what it was capable of. I also needed to get used to riding it once we were on the road as well.  


It’s so important to understand what tools or equipment you have available to you and how to use them. For me I was riding an unfamiliar bike and so I paid attention during my briefing.

From a business point of view, you and your team are your most valuable tools, how well do you know them? What motivates them or inspires them? What skills, knowledge or experience do they have that will help you towards your objectives and goals? When you have a new team member or piece of equipment you need to know what they/it can do and most importantly how to get the best out of them.

If you haven’t done so already explore the skills, knowledge and experience you or your team possess, you may well be surprised that there’s more than you knew!


4. Brief your team regularly Management & Leadership Development in Sussex


I have always been an advocate of regular team meetings. When they are done well they help to keep the team on track and keep you up-to-date with how they are and what problems might occur. They don’t need to take long or be particularly formal. They do however need to happen and they need to be two-way, so that you gain feedback from your team about how you’re doing as a leader or ‘guide’.

In our case we had daily morning briefings to let us know our destination for the day and what we might see/encounter along the way. This included weather or traffic areas that might cause us a problem or that we should look out for. These meetings were supplemented at each stop with a quick check on how we were doing and where we were going next.


Keeping your team informed is crucial as it helps to ensure that you’re all going in the same/right direction. It also gives you a valuable opportunity to gather feedback on the team, on what they need from you as a leader and any problems that might be coming up. In my experience it really is a case that clear communication pays dividends both in life and business.




Management & Leadership Development in Sussex5. Celebrate each milestone or step towards your goal as a team


In addition to the daily morning briefings we took the time to have a catch-up at the end of each day to celebrate reaching our goal that day, an opportunity for a cold beer or beverage and a pat on the back for another part of our goals completed.  It became a little ritual – get to the hotel, unload the bags off the van and have a cool beer or soft drink and congratulate each other at the end of a good ride.

Now whilst you might not want to do this every day in business (although there’s no reason why you shouldn’t), how often do you ‘celebrate’ or recognise milestones in your business or team? Recognition acknowledges progress. Recognition promotes pride and learning, a time to reflect on what’s been achieved before moving on to the next task or step. Otherwise it’s “just another day at the grindstone”. Make sure you recognise achievements, either for yourself or within your team. Support your team in their efforts to celebrate success.



We travelled over 2800 miles on our journey together, yes we got lost occasionally (Preacher!) but we always met our objectives at the end of each day. We all celebrated each day together, shared our experiences and by the end of it we had turned into a pretty good riding team, working together and supporting each other to get through the madness of traffic that is Los Angeles as a group. On our journey to hand the bikes back, not once did we get split up, despite working our way through 6 lanes of wall to wall traffic and helping each other to achieve every turn-off and junction. We had a fabulous time, experienced and saw so much and I’d like to think that we saw a real cross-section of an enormous country. We certainly had a good celebration when we rode onto Santa Monica Pier to mark the end of our journey on Route 66.


So how well do you lead your business or team? Do you have regular checks against your plan? How do you celebrate your milestones and success?


What adventures have you had that you’ve learnt leadership lessons from? What do you do with your team that works for you?


I’d love to hear your thoughts on this blog and the lessons that I’ve drawn from my adventure, why not leave a comment and share your thoughts with others?.


Part 2 of this blog with more lessons on leadership from Route 66 can be found here 


Martin Smith Learning and Development Ltd is a professional training and coaching consultancy working with business leaders at all levels to provide improved business results, increased profits, greater staff performance and retention. We help you to GROW your business by developing your people.


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