It was about a year ago when I was sat in Newbury town centre having coffee with an old boss when he said to me:

“There are always 3 things on a CEO’s mind – time, team and money.”

At the time I thought, “Surely there’s more?”. But when you investigate the pains a business feels, it always points back to one of these 3 core challenges.

Money, in particular, is an interesting one. Some people are in business to make a fortune, while others see it as an enabler for other things. But whichever side of the fence you sit on, the fact remains that a business needs to grow – either adding more clients to scale the business, or replacing those you’ve lost through organic churn.

58% of business leaders say that lead generation is the key challenge they face[1] – in fact, only about a fifth (22%) of businesses are happy with their conversion rate[2].

So why is it so hard to build a pipeline? And more importantly, how do we overcome those challenges?

1. No process

Straight in at #1 is perhaps the simplest problem to address – 68% of companies have not identified or attempted to measure a sales funnel[3].

By better managing your sales pipeline, you can instantly give your sales revenues a 15% boost[4]. And it doesn’t have to be anything super fancy – I manage mine in Trello with columns for:

  • Qualified out
  • Leads
  • Marketing qualified leads
  • Sales qualified leads
  • Quoted
  • Clients
  • Not now

If you don’t already have a ‘formal’ process in place, sit down and spend some time writing down how you do sales today – and be honest…

Then look at that process and think about how it could be improved.

For example, in my own business I wrote a list of ‘red flags’ to help me qualify out quickly the opportunities that weren’t quite right. I also wrote a list of questions that I ask people in that initial discussion, so rather than write them from scratch every time I can just tweak them.

It’s not about scary huge changes, it’s about getting something down to then tweak, test and refine over time.

2. Lack of alignment between sales and marketing

Surely it’s a problem as old as time?! The two business functions that should sit hand in hand and yet so often they’re sworn enemies.

A quarter of sales leaders admit to never meeting with marketing, while over half (58%) will only meet to discuss pipeline on a quarterly basis[5].

I genuinely don’t understand this. Marketing is responsible for lead generation, so how can sales keep them at arm’s length?

In a previous article I discussed why this lack of alignment is a massive business issue and how with one simple act you can bring the 2 functions together:

Ask your sales team to write a list of content they would find useful to help them do their job.

Offered as an olive branch, this simple question is enough to get the 2 functions talking and realising that they can (and should!) be supporting each other for the good of the business.

3. Too old-school

Over 40% of business leaders describe their current sales and marketing efforts as ‘outdated’, with a third relying on cold calling[1].

This literally makes me shudder. As anyone who has worked with me knows, I am anti-cold calling and will fight passionately to not follow it as a strategy for business growth (not that I’ve always won those battles).

Thankfully in the age of GDPR, it’s becoming much harder to employ such horrible lead generation practices, but I have seen agencies still offering GDPR-compliant cold calling – although I’m unsure as to how that’s legal.

For anyone thinking about picking up the phone and calling someone who doesn’t know you, I beg you, take a second to put yourself in that person’s shoes:

How will you feel when you get that unexpected call?

Are you really going to buy? Or even listen to what they have to say?

Is it going to leave you with all the warm fuzzies? Or is it going to niggle and irritate you once you put the phone down.

Surely your time is better spent elsewhere?

If you’re in need of some ‘quick wins’, why not go back through your LinkedIn network and re-establish contact with some old connections? Send them a message, write them a letter, invite them for a coffee and a catch-up…

And then get to work on establishing the mechanisms that ensure a steady drip feed of leads into your sales funnel.

4. Inexperienced and under qualified

We all start our careers at the bottom. But in small businesses, where you perhaps can’t afford to hire a skilled CMO, the tendency is to hire graduates or junior people and train them up.

And I’m not knocking this approach. It’s how I started my career, and many other marketers I know.

But the problem comes when you award that person the ‘manager’ title and promote them ahead of the skills they possess. When this happens, it can be dangerous because you’re awarding responsibility for your business growth to someone who really doesn’t know what they’re doing. And either that person is too scared, too arrogant, or doesn’t know to ask for help.

42% of marketing departments struggle to discover the best strategy, channel or offer to entice their target audience[6] – something they need to get a handle on quickly when buyer expectations are constantly changing.

Of the leads that are generated, 50% are bad matches for the business[6]. As every good marketer knows, lead generation is as much about qualifying out as it is qualifying in – saying ‘no’ is a really healthy thing for your business because otherwise you’re get caught up servicing the wrong opportunities that sap your time, effort and money.

And then a third can’t measure the success of their lead generation efforts[6]. Marketing has a bad enough reputation as it is, and not being capable of proving your worth only exasperates the problem.

Hiring internal marketing resource is a good thing and I would always advise investing in the most experienced candidate that you can afford. But also surround yourself with a network of freelancers who you can call upon if/when you need them.

These are highly skilled professionals, usually specialising in one thing, which means you’re getting agency-grade work at more affordable prices – and without the HR headache.

5. Limited resources

38% of companies claim they don’t have sufficient time, money or staff to generate leads[7].

As I’d say to my boys, “That’s nonsense and bojangles”.

We’ve just highlighted that freelancers provide you with the best talent for a limited budget – and if you don’t know any, ask me, I’m more than happy to make introductions to some fabulous freelancers…

We’ve also talked about revisiting past connections to warm them up, and establishing mechanisms to create a steady drip feed of leads – this ‘inbound’ marketing cost 62% less per lead than ‘outbound’ marketing, like cold calling[8].

And then there’s a really clever thing you can do to boost your pipeline – know your customers.

I’ve heard the phrase “our target audience is anyone and everyone” too many times throughout my career, and it’s a key reason you’ll struggle – in trying to appeal to everyone, you appeal to no-one. Just because your product/service COULD be used by anyone, doesn’t mean you SHOULD target them all.

Next steps…

I’ve created ‘The Content Framework’, which shows you how to map your content to your sales pipeline, along with expected conversion rates, and how to effectively plan a quarter’s worth of content to help you secure a steady drip feed of leads.

To get your hands on a copy, you just need to put your name on the list…

The added bonus of doing this?

Every month I’m going to introduce you to another fabulous freelancer and share insightful content with hints, tips, tricks, advice, love and support to help you scale your business.

You in?

[1] Source:

[2] Source:

[3] Source:

[4] Source:

[5] Source:

[6] Source:

[7] Source:

[8] Source:

[9] Source: