12 biggest sales challenges in the digital world and & how you can overcome these

The following list might be of interest to the leader of a business, or a senior member of a team with sales and marketing responsibility, who is seeking to make sense of how the digital world is affecting their ability to sell.

Whether or not you think these 12 points apply to your business, the fact is that these points reflect more than 30 organisations that I have had the pleasure of coming across, in some capacity of other, over the past 12 months.  These organisations span £100m to £50k turnover and include not for profit. And the humbling truth is that we can all find reasons why stuff wont work. We can find lots of real examples where a suggestion is not working, but that is missing the point. Perhaps just 5% of businesses can be deemed to be successful at any one time, and these successful businesss are, of course, not successful all the time.  So do you want to be a follower of 95% unsuccessful businesses, or a leader, cutting your own successful furrow?

So, the 12 challenges, and their soluitions, are:

1. Fail to plan, plan to fail. What sales numbers are you trying to hit? As I am sure you will appreciate, the solutions for selling 10,000 pairs of shoes to the public at £30 each are very different to selling one £300,000 contract to supply stationery to a business for a year. Start your planning with the end in mind.

2. People (and website designers are generally happy to be part of this crowd) think that a website will bring the leads in. It will, only if part of a wider website marketing plan that mirrors the journey of a potential client, ie:

a) Be present where your potential market hangs out (eg on social media, at an event)
b) Give them reason to visit your website (eg download some free information that they value). Ask them to opt-in to giving you their email address.
c) Keep communicating with them as they go through their decision-making process (eg email marketing, phone calls).
d) Give them low cost options so that you can get started and can earn their trust (easy in, easy out). Design sprats to catch mackerel.
e) Find a way to solve more of their pain (client account management: sell them more, invest in them to maximise their lifetime value to you).
f) Find ways for them to be advocates of you and to spread the word. (Word of mouth is perhaps more important than ever before.  It can cut through the noise).

3. Create a content generation machine. Ask your current clients what content they would find interesting. Keep an endless supply coming in by asking the team to contribute. Give someone the responsibility for chasing it up.

4. Just do it: don’t strive for perfection; launch the product at a time when it is adequate for client needs, not when it’s perfect. Admittedly adequacy hurdles are higher in some industries than in others (eg Airbus launching a new model of airplane!) but the important point is that the best design comes from real feedback from real clients putting your product into real practice.

5. In B2B selling (and high value B2C items): keep the faith. Keep going and measure each gate in your pipeline: it can take 6 months, or more, for clients to make big purchase decisions.  If you don’t think so, I bet you have entered the race too late.

6. Get stuck into the social media debate. Don’t let the cynics stop you. It will be affecting your business/marketplace somehow and best that you know how. 10% of businesses use social media correctly. Social media is networking done online: people will flock to you if you think of them first, give them something without a moment’s thought about yourself. Don’t be the bore in the ‘room’. Be engaging. Be colourful.

7. Sooner or later (depending on your ambition) you will be limited by how quickly you can generate leads. Key tools for ‘volume’ lead generation are social media, search engine optimisation and online advertising.

8. New sales opportunities are really tough to acquire: think process (the days of ‘secure the sale and clear off’ are long gone) and think life time value (keep reselling to your existing clients).

9. The power is in the niche. Google has driven this (when you search, you search using a specific word or phrase; only the search match that best meets your needs is of interest to you). You can not profitably service everyone. Invest in developing a position of thought leadership, one that your niche can recognise. Then you will be able to command your price.

10. People new to selling tend to give up too early. Research shows that it takes 5-8 ‘asks’ before a piece of business is awarded. Keep going and add value to every interaction.

11. Measure. Be forensic. Is it really a ‘closing the deal’ problem that you have. It may be symptomatic of another problem, such as insufficent leads (if you are closing ‘only’ 30% – depending on the point from which you are measuring – you might be doing very well). It could be that your leads are of the ‘wrong type’.

12. Some people think digital does not affect their market or that digital is their only market. So why has Waterstones the bookshop had such a torrid time yet Amazon has announced their first bricks & mortar store?  Its all about the integration of online & offline activities for the new digital consumer.

I hope that this article is of (provocative) use to you. Do let me know your thoughts.


Having been in the game for 30 years I consider myself a mere marketing and sales amateur: there is so much more to discover. However, I hope that my headstart can be used by a select number of ambitious leaders of £1m+ revenue businesses who are based in Oxfordshire, or nearby, and who sell products or services to other businesses. My mission is to help them sell faster, at least cost and avoid the many mistakes that I have made along the way, whether during service in established big brand outfits, successful challenger brand companies or my own former 80 employee business. I am very grateful too to those who ask me to talk, run training sessions, mentor or judge on the Oxfordshire entrepreneur circuit.

Posted in How to sell more, Marketing and sales tips
26 comments on “12 biggest sales challenges in the digital world and & how you can overcome these
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