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Selling lessons from the saddle.

On the 8th September 2018 I sat on the start line for a totally awesome, yet challenging, adventure. Riding the length of the UK from Lands End in Cornwall to John O’Groats in Scotland. I was with another 700 people, ready to cover 980 miles, a lot of hills (like cycling up Everest twice), camping every night for 9 days.  

I was confident that I was ready. I had been preparing for this moment since the start of 2018 and I was in the zone. Mentally ready to go and eager for the starter to send us on our way.

I learnt a lot about myself in the 9 days that followed as we covered over 110 miles a day. On reflection there are some similarities too with B2B sales professionals.

In this article I want to bring some of the key selling lessons that I have taken from the saddle. Let’s get into this.

1.Focus on your goal

In january I started to visualise finishing the event and thinking about what it will take to reach this goal. I am sure the 700 starters each had their own personal goal and for me it was only to complete the 980 miles. It was not to do the distance quickly or in a specific time, reaching the line was enough. This meant that, despite being in the bottom 20% of riders each day, reaching John O’Groats was a total success for me. Had I lost focus on the goal and tried to do this faster there is a good chance I’d have ‘blown up’ and not made it to the end.

The key lesson for sales is this – have a clear objective for an account (to advance) or opportunity (to win, or lose early). Defining your sales objective will help you to focus on delivering this objective successfully and to do what is needed to deliver this successfully. Trying to run too fast or failing to keep up can cost you and result in failure.


2. Plan for success

Planning for the environment you face the following day was really important, considering the ride distance, temperature, rain chances, the ride profile for climbing and descents, pit stop distances and start times all played a part.

I had to select the right clothing so I would not be too hot or too cold on the following day’s ride. Once I set off it would have been too late to wish I had a waterproof with me. Knowing where the major climbs are in the ride meant I knew when to push hard and when to ease back to conserve some energy for the ride ahead.

In a long sales campaign the lesson here to have a plan. If you know the key deliverables along the way it is possible to adapt your sales approach for times when the velocity of the deal increases and slows. Your playbooks will help to define the right activities throughout the buying and sales process and offer you a plan to guide your actions. Allocate time to plan for the future and this will allow you to focus on doing the right things.


3. Sharpen the saw

I’ll be honest here, I didn’t do enough of the right training to make this challenge easier. My bike skills were good, but the strength in my legs was not where it should have been for such a challenging ride.

I could try to make excuses but the reality is that I have to take responsibility for this, more training would have helped. Had I been better prepared I would have performed better. I did enough to get to the end and this was success, but it was hard work and I could have made it easier to achieve my goal.

In sales there is debate about the value of training and coaching. My lesson from the saddle is this, always try to improve your selling capability. This means understanding the key dimensions of sales performance, and investing in your personal development to be better. Take responsibility for this and be aware that mastery takes effort. Whether you do formal training, coaching sessions or self learning. Invest in being better.


4. Use the right tools in the right way.

Cyclists spend fortunes on new bikes, clothing, shoes and accessories. Some of it will trim a few grams of weight and in theory improve performance. But having the right kit is not enough if it is not used in the right way -some people have “all the gear and no idea”.

I completed the last 40 miles of my ride into John O’Groats in a single gear as the battery powering my gear shifters ran out. Doh! This made things harder and added a lot of time to my ride on that day. My performance was affected by my inability to use the tools at my disposal in the right way.

Sales tools are sometimes touted as a silver bullet – ‘buy this software and you will improve’ some suppliers will say. The reality is that tools can be part of an answer but if they are not used correctly then performance is impacted. For example our account planning tools will provide a simple way to build an account strategy in Salesforce, but to build a great account strategy requires creative brain power too.

The selling lesson is to buy the right tools to address your performance gaps, and prepare people with the right behaviours and capability to use the tools in the right way.



5. Mental strength gets you through

There is no doubt about it, this was an endurance event. There are some really tough moments throughout the ride that are sent to try you. Starting out on a 2,000 foot climb after 50 miles on day 7 is tough on the legs for sure, but it is the mental toughness that will see you through. When you set off on day 8 at 630 am in the dark after waking at 5am with ice on the inside of your tent it is not the strength of your legs that get you going, but what is in your head.

At the top of some of the major climbs a Union Jack flag could be seen fluttering in the wind. It said “SHUT UP LEGS” and this highlights the mental approach necessary to keep your legs going when physically it would be easy to give up and walk.

Sales is tough too. There are some hard times in any sales campaign, when decisions go the wrong way or when an opportunity is lost. When a customer refuses to meet with you or a prospect won’t take your initial call or return an email. It is important to put these setbacks and challenges into the context of the long term goal. Having the mental toughness required to stick with things through tough times is what defines great sales people.


6. Individual AND team

Cycling the length of the UK is an individual challenge. It’s you and the bike against the route and ultimately it’s down to you if you succeed or fail.

That said this challenge reinforced the important role that others played in my success. There were times over the nearly 90 hours in the saddle when I was not not having a good moment. The friends I rode with encouraged me, supported me and helped me through those tough times. I would have found it much harder without their help. At the same time there were moments when I would be there for them.

Sales equally is [mostly] an individual activity where the salesperson carries the quota for a set of accounts or territory. The best sales people I have seen are able to corral resources to help them win. They use the expertise of others to help move things forward. They use a team to add capacity at times when more productivity is needed. They are there to help with moral support.

It is clear that a good individual can become great by identifying the resources that can help and leading this group in the right way to garner team spirit. As a result of working with others it is possible to deliver better results for all. Sacrificing individual performance for the good of the group is a valuable lesson.


7. You need courage

The organisers of the ride have a motto – ‘more is in you’. This fits so well with my experience and I had to push myself just that little bit further than I believed possible when I signed up.

If you cycle you know it is tough going to complete a “century” ride of 100 miles or more. But 9 century rides back to back, coupled with some iconic (this means big) climbs makes this tougher. Without the courage and the belief to think big, have a go, work hard to prepare myself and make sacrifices related to friends and family activities I doubt it would have been a success.

So what does this mean for sales, and specifically sales management. Well sometimes you have to have the courage to make choices. Choosing not to pursue an opportunity or bid requires the courage to walk away and say no thank you. Investing resources on a specific account often requires courage to divert resources from other accounts. But without choices and the courage to make the tough decisions you are not leading the team.


8. Your actions can contribute to a greater good.

I am proud that my ride is contributing to a cause bigger than my own personal challenge. I have raised thousands of pounds to help those suffering from the effects of Parkinson’s. It feels good to be part of their team and that the effort I put in is helping others. I am totally grateful for the support of my sponsors. 

In sales, how you behave can affect the reputation of your company and an ethical approach to your sales campaigns will enhance how you and your company are perceived in the market. Keep up the good work and always do the right thing, even if this requires personal suffering and extra effort.

We are a proud supporter of the Pledge 1% movement.


9. Sometimes you face the unexpected, deal with it.

However much you prepare you can’t plan for all eventualities. I was lucky that my ride was pretty uneventful in this regard but others suffered. One person made it two miles before falling off and breaking a wrist that put an end to his adventure. Others suffered severe saddle sores or injuries that affected their ability to perform each day.

Sales campaigns are not predictable. Why, because they involve people and emotions. Things don’t always go as you think and deals surprise you as the customer makes a decision different to how you expected it to go. It is important to be aware of your situation and showing the ability to adapt and flex to the changes.


I took 9 key selling lessons from my time in the saddle. Sales is a long term endurance activity in the same way as my 980 mile ride was. It requires focus, commitment, flexibility and a belief in yourself.

I hope this helps you in your sales career. Good selling.


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