Things I’ve got wrong in sales and marketing (so you don’t have to)

Maybe you’re not sure about where to start with new business, sales and marketing, and are worried about getting it wrong.

Maybe you’ve tried a few things, but you don’t know if they’re working or not, so you’re not feeling very confident about the next steps.

Maybe you’ve jumped in and invested in activities that you know a bit about, but they’ve turned up nothing, or taken you nowhere, and you’re not keen to do that again.

Or maybe you’ve recently hired a big-hitting new business resource, but have a horrible feeling that they might be doing it wrong – but as you’re not sure what right would look like, it’s really hard to articulate how you feel.

If any of this sounds familiar, then this post might be of particular interest to you.

I realised only the other day that….

I feel most confident about the quality of my advice when I’m able to see very clearly where a client had taken a wrong turn, or where they’ve missed out a key step.

I was trying to work out why I feel so confident then – rather than at other times – and I realised it was because I recognised their mistakes from my own mistakes, earlier in my own business development career.

So, I thought, maybe other people would want to hear about my mistakes so they can avoid them in the future.

Hence to writing this.

My best, and worst, new business mistakes

And just to be clear, by mistakes I also mean….. wrong turns, catastrophes, inaccuracies, miscalculations, errors, oversights, failures, slip-ups, stuff-ups (I’m keeping this clean here), omissions, fiascos, flops and blunders.

Things that you get wrong, and things that go wrong – generally because of a decision that you (yes, you) have made.

You’ve got to become proud of your best mistakes.

I’m calling them by best mistakes, because (as I mentioned) if I hadn’t made them, I wouldn’t now be able to recognise when others are likely to make that mistake, or have already made it. So I wouldn’t be able to give such useful advice.

In no particular order..

1.   Buying data at all / buying the wrong data

When the right thing to do was grow it organically or buy a much, much more tightly defined chunk of data. This was in the days before LinkedIn and very early in my new business career, when I knew virtually nothing about sales.

Learn more about your options with customer data from someone or somewhere before you decide what to acquire and how to acquire it. It will save you a lot of wasted effort, money and hassle.

2.   Taking too long to plan a marketing campaign in order to get it ‘perfect’ instead of getting it out quickly

The learning curve that comes with most small businesses’ first marketing campaigns is huge. So often the best thing to do – for a better overall result – is to tuck in and get something reasonable out, measure it, learn from it, and do it properly the next time, or the time after that. Now that campaigns are so often digital (I was talking physical direct marketing), it’s even more of an iterative learning process with a lower entry cost.

A balance of thinking and action is reasonable – don’t just do shoddy marketing because it’s quick – but worrying about being perfect can really slow you down. Avoiding a committee-based approach to marketing can sometimes really help with this.

Take advice, use professionals where you can, or go with your gut and then get feedback to improve it.

3.   Letting myself be trained/mentored by someone who I didn’t think was right for me or the business, but not saying anything because….. well, what did I know? 

After being thrown into the deep end of new business following my first child, I was given a sales mentor who came into the firm regularly to advise both me and the board – strategically and tactically – about sales and new business.

The sentiment here was spot on, because we all needed help, especially me.

But the resource was (in glorious hindsight) the wrong one. A lovely guy, but someone who didn’t understand our industry and the problems we faced, someone who came from a more traditional sales background and was less familiar with the higher value consultative sell that we needed to know about.

And I took that advice and began running with it. My mistake.

If you’re getting advice about sales or marketing, and deep down inside it doesn’t feel right for either you or your business – or the advice feels too narrow, or too broad, or just a bit…. off – then listen to yourself, and spread the net wider and do a bit more digging to find the right advice for you.

4.   Letting the wrong people into the sales process at the wrong time, just because they’re more senior

This is a really tricky one, because it involves personalities. But the best person to do sales in your business is not necessarily the most senior one; or the boss (whatever they think); or a director (however experienced they are); or the one most experienced at sales (ironically). More on this here.

5.   Realising you’re not always the right person for that stage of the sale

The best person to do sales very often depends on the stage the client is at in the buying process, and the personality of that client. And it might not be you – at that particular moment.

Clearly this is most relevant when selling higher value B2B services where you have a longer buying cycle, and not so much if you’re selling Mars Bars.

  • When a client is first recognising they have a problem, they welcome helpful business insight and a wider-ranging look at problem solving.
  • When they start looking for solutions, they may want to be inspired and excited by a fellow business owner – to start trying on their wonderful ideas.
  • And when they come to finally choosing a supplier, they might want much more detailed and specific product or company information to assess your fit.

And because it’s often the fact that different people in your firm that can bring those different responses to the client – make sure that whoever is actually RESPONSIBLE for new business gets to choose who the client sees, when.

Because then they should try and make the best possible judgment with the information and knowledge that they have.

(Note – this only works as long as they’re a reasonably good judge of both client, colleague and themselves. And if they’re not, you’ve got to question whether they’re the right person to be doing new business for you in the first place.)

6.   Not measuring anything enough

I never even thought about how to measure my early marketing efforts, although I quickly became pretty good at measuring and analysing our sales pipeline.

Knowing where your sales come from – and why – is crucial to repeating successes and avoiding the failures.

And try your best at doing the same with your marketing – it is SO much easier now that a lot of it is online. It could even be as simple as asking every enquiry how they heard about you or using a promotional code in your printed advertising.

COP OUT: I’m not going into detail here because measurement is a whole subject in itself.

7.   Not having enough belief in my own writing

In a marketing agency, you use professional copywriters to write copy for your clients. So I believed only copywriters could do that writing thing.

It’s only recently I’ve learnt how to find my own voice, and been confident enough to use it. I now help some of my own clients – especially those in smaller start-ups where the voice of the founder directly reflects the sentiment of the brand – find the confidence to use their own voices where it’s right for them.

8.   Outsourcing telemarketing without understanding enough about it (having never done it myself)

This was an outright failure done before either I or my company realised how much there was to learn about new business.

Either try it yourself first (seriously), or learn a lot more abut it before you do anything. Or you will get lots of coffees and chats, you’ll get people who aren’t sure why you are there (or why they are), you’ll get meetings set for you where prospects don’t even show up…. the list goes on. 

9.   Outsourcing telemarketing soon afterwards without getting a whole load of ducks in a row beforehand (even when I knew more about it)

Repeating mistakes is really embarrassing, so I’ve made this one slightly different…

I assumed that a good telemarketing agency would be able to guide us through the process and advise on everything we needed to get done to be ready to use telemarketing as a successful channel.

Now, however, I realise that only a few will actually do that – and even those few that make good suggestions will rarely go so far as to point you in the direction of the wider new business advice you might desperately need before you start using their services.

Even when you know something about telemarketing (and unless you are the only person with water in the middle of the desert), please remember these 6 points:

  1. You need to be well positioned and able to differentiate yourself from your competitors.
  2. You need to really understand your audience.
  3. You need to have clear criteria around which companies would qualify as your prospects, and why.
  4. You need to be able to clearly identify buyers, decision makers and other people involved in the buying cycle.
  5. You need to be able to articulate the problems they have, that you can solve.
  6. You need to be very clear about why they should talk to you, instead of your competitor.
Then hopefully the meetings that are set for you will be valuable opportunities to build new relationships with potential buyers.

Not random chats with random people at companies you’d never in a million years be able to work with or would want to work with you. (True story).

10.   Not trying hard enough to persuade my boss about the utter importance and value of positioning

At the time, I didn’t have the authority and autonomy to do what I really wanted.

Which on one hand wasn’t a bad thing (at that stage I was very much learning), but on the other hand I’m a fast learner and couldn’t put into practice some of the truly valuable knowledge I was acquiring.

I’d found myself a new mentor and my perspective very quickly shifted.

He was a brilliant trainer, totally understood our sector and challenges and I’m very sure if we’d followed all his advice to the letter, success would have been ours on a plate.

But I didn’t have the powers of persuasion that I would have liked – and crucially didn’t yet have the confidence to really push to do what I thought was right. So I did what I could, where I could. But it felt a bit half-hearted sometimes, and I regret that I didn’t try harder to get my beliefs across, or even move on earlier.


Well, there’s a post that is all quite cringeworthy to write from my perspective. A bit of a day of reckoning looking back at all the things I’ve done wrong in the past…. Glad that’s over!

I’m sticking with the view that getting it wrong has helped me get it right, and it means I can help prevent others from making the same mistakes.

Looking for help with your sales and marketing?

If you are looking a freelance, flexible resource to help with your business development, you can hire me. I’m a director-level sales and marketing consultant, based in Hampshire, UK, and work with small and medium sized b2b businesses.

4 responses to “Things I’ve got wrong in sales and marketing (so you don’t have to)”

  1. As a test pilot, my job was to discover failures in complex systems. These may have been failures in the system’s specification, design, build, its operation, training needed, whatever. Failures happen when you’re making something new.
    Having found a failure, the next step was to recommend a range of solutions. For instance, compensate for difficult operation by training operators better, or through re-design, or, more simply, by not trying to do so much – reduce the specification.
    The last step was to record the failure, and the solutions (including those which failed!) so others could learn from your mistakes. Feedback.
    Businesses are complex systems. Creating new ones is all the more complex, because new businesses performance is difficult to measure. There’s no feedback loop in early days – except through detecting mistakes earlier, and finding the work-arounds.
    I like the idea of borrowing your mistakes instead of finding my own!

    • Kim Mason says:

      Thanks Jim, glad you liked the post. Although I think you are probably way ahead of me in terms of business experience with some trail-blazing successes! (From Dinghy Sailing in Greece to Neilson Sailing for one….)

  2. It takes a big person to admit they’ve made a mistake and an even bigger person to learn from it. Kim you’re a hero for sharing yours for the greater good. There’s some really deep insight in there, thanks very much!

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