freelancer working micro biz mag

5 Questions to Ask for More Effective Client Prospecting

“Asking smarter questions can help you run a leaner sales funnel.” That’s the advice of freelance copywriter, Daniel Rosehill, who writes this piece for us on prospecting more effectively.

“Asking smarter questions can help you run a leaner sales funnel.” That’s the advice of freelance copywriter, Daniel Rosehill, who writes this piece for us on prospecting more effectively.

The current economic downturn has got many freelancers (including this one — hit me up!) thinking that it’s time to ramp up our outreach and look for more work. 

In fact, if you are a freelancer, I would argue that there is virtually no reason why you should not be looking for more business right now.

This is because of what I call Counterintuitive But Painfully True Freelance Axiom Number One which states as follows: Even during periods when one is at maximum capacity one should continue prospecting for work. (What happens if you are too successful at this? You might curse your diligence, buy yourself a large supply of coffee, and lock yourself in a room for a week or two. Just before you feel like you’re about to have a nerve breakdown you look into whether your contracts allow for outsourcing).

But why put yourself through such potential mental anguish, you might be wondering?

Because of something known as Murphy’s Law — The Freelancer’s Version which states that “even if your client base is well diversified (and that’s Freelancing Axiom Three) work tends to have a habit of dropping off — and surging back up — at the most inconvenient of times.”

Clients can tank concurrently just when you’ve bought a new car or well up, without forewarning, just as you’re about to head away for some well-deserved R&R (and in this case I advocate that you disconnect and take the time off.)

In other words, irrespective of whether you’re currently twiddling your thumbs and binging on Netflix or you have more work than you can handle you should probably go out there and start prospecting. Sorry to rain on your Netflix parade. 

But of course one should always strive to work smarter rather than harder.

So in that vein here are a few clever questions that might help to guide that initiative. 

1. Is This Prospect Likely To Have A Budget?

client prospecting budget

It’s hard to write this without sounding like a bit of a judgmental (expletive) — particularly during these straitened economic times.

However, hitting up large trenches of clients that have no reasonable prospect of paying your professional rates is a sure-fire recipe for frustration.

In “Know Your Freelance Client: Due Diligence for Freelancers” I provided a methodology that can let you do some serious sleuthing into whatever companies or individuals you might end up working for. 

Know Your Freelance Client (KYFC): Basic Due Diligence For Freelancers

If you started the new year on a quest to scale up your freelance business, then you’re probably on a business…

The premium version of my online intelligence-gathering package is pretty darn intense and would give an FBI background check a good run for its money (just kidding). But in virtually all cases — unless you’re looking at taking on a large project for a very long time, that is — there’s no need to go the full nine yards.

Rather, you can just bear the following axioms in mind:

  • Very early stage ventures, like seed-funded startups, are often jealously guarding the limited resources that they have. These are probably not mature enough to approach yet. (If you’re looking to command reasonable rates, that is). If you’re a creative, like me, then you probably already know that in a budget allocation battle with developers we usually lose out. 
  • Even more mature startups might not yet be investing heavily in sales and marketing. In fact, there’s a good chance that they’re not making very much money at all. And until they do, again, budgets tend to be either constrained or spent very inconsistently. 

Some of the basic information you’ll need to attempt to appraise how a company is likely to be doing financially is thankfully in the public domain. 

You can look at things like:

  • Press releases announcing funding rounds.
  • Private tax returns — if you can buy them.
  • Funding history.

⬆️ How you can leverage this:

  • Find companies that are turning a profit, or those that are well-funded enough to be taking what you do seriously. Target those in your outreach.

2. Who Does X’s Marketing?

It also makes a lot of sense to consider what services provider might already be tending to a lucrative account.

At the enterprise level of scale, there can be an entire ecosystem of agencies and independent providers all making various parts of the jigsaw fit together. 

A large company’s marketing team, for instance, may variously draw upon the input of strategic marketing consultants, freelance writers, SEO specialists, and various PR firms — sometimes with different firms even covering different media markets. 

Unfortunately the more long standing these relationships the more difficult they can be to dislodge. 

If you’re really interested in working with a prospective client then this information might also fall into the purview of things you will have to find through closed sources (ie, the information is not in the public domain). If you have a contact at the company it might be worth asking who’s doing X. If it’s handled in-house but the team is bursting at the seams of its capacity, then you might have a possible ‘in’.

How can you figure this stuff out besides taking people for coffee or working your Rolodex?

It’s usually in the service provider’s interest to brag about the fact that they provide services to Y — and not those of the company. Trying some reverse lookups using this technique may be fruitful. Some queries I would consider running if I were trying to get a feel for what kind of agencies Microsoft use, for instance, might be:

  • “our clients” + Microsoft
  • inurl:clients + Microsoft

If you like the look of the agency it might be worth dropping them a pitch and making note of the fact that you were impressed by the fact that their client list included Microsoft. Might they need some additional resources to help service the account?

⬆️ How you can leverage this: 

  • Look for the companies that seem to be lagging behind the pack in terms of their marketing efforts. Ramping up might already be on their agenda and your approach could be well-received. 
  • Alternatively try to slot in with a major provider’s agency. Down the line, you might be able to leverage this to your own benefit. Although the anti-compete clauses you might be required to sign might in practice limit how far that ‘line’ stretches.

3. What Does X Put Out?

The next step in your intelligence-gathering effort might be taking a careful look at the resources that a company you are interested in working in has put out. 

The above screenshot is of VMWare’s technical paper library at the time of writing. 

Quick psychological side-note here: if you’re thinking about approaching a company, then don’t worry about coming off as being creepy by seeming too ‘well informed’— this is a neurotic concern that plagued me for no good reason for years and still to a small extent does. This isn’t school (or online dating) and a basic amount of internet-plumbing is fair due diligence. In fact, the company would more likely be impressed by the lengths you have gone to in order to know what they are doing marketing-wise. 

There are a few insights you might glean from this process:

  • ???? The company may be rocking things in the marketing department. If a company looks to be very ‘well-covered’ then it’s naturally a little bit harder to make the case that they might need additional resources. If there’s a piece of writing that really resonated with you feel free to point it out. Of course, they’ll be more interested to know what you might be able to add. So if you have had some brainwaves, then feel free to drop those into the pitch.
  • ???? The company may be putting very little resources into the marketing department. This is sometimes — not always! — the result of a disdain for marketing (or your area of focus) from ‘on high’ or due to a poor budget allocation. Your approach here naturally needs to be somewhat more tactful. Pointing out to a company that their blog flat-out sucks, is littered with typos, is unlikely to win you any internal cheerleaders. However pointing out the potential value of what your contribution could bring, without explicitly mentioning the fact that they aren’t doing that, is likely to be a more successful conversation-warmer.

⬆️ How you can leverage this:

  • There’s always room for improvement: have some thoughts ready on what high-performing marketing teams could be doing better. 
  • Look for companies that aren’t quite thriving yet in your area of expertise — but those that are not in that bracket because of internal resistance, which can be almost impossible for an external provider to try to displace.

4. What Are Their Competitors Doing?

You can’t discern what trends are happening in an industry just by looking at one provider. 

As I mentioned above, it helps to come with suggestions ready to bring to the table. And — if you’re looking to make a positive contribution to a company that you are excited about the potential of working with — to understand what are the major trends shaping their industry at the moment. 

In general, companies pay close attention to what their competitors are up to. So it can be advantageous if you can demonstrate that you already understand what’s happening in the industry — and more advantageous still if you have some ideas to float about how your prospect can do things better than those they are in competition with. Most companies aspire to be the dominant player in their niche. And almost all companies — 

no matter what they tell you — have some form of competition. If they don’t, then their problem is likely to be convincing customers that there is a need for the product or service they sell. Assuming that you live in a free market economy, you will find that the more old and jaded you become the more you become convinced that most genuine needs are already being addressed by somebody — or multiple players.

⬆️ How you can leverage this:

  • Know both what a company’s consumers are writing about — if they are not — and what the major trends are in their industry. Propose that you could help the company also hone in on these debates. Of course, you’ll want to be also able to point out how you can help them do things better

5. Who Are They Failing To Reach? 

Most medium to large organizations have developed a series of well-developed buyer personas. And their go to market (GTM) strategy likely provides a high level of detail — usually backed up by empirical market research findings — as to who those likely to be interested in their product are. 

Of course, we can also all think of a few examples of major brands that have done a horrible, tone-deaf job of attempting to reach certain demographics= such as Generation X and millennials.

In other instances, a company might be preparing for a push into a geography you’re familiar with (or live in). Could you leverage your understanding of the local market in order to help the company build resonance and connect with the right influencers. 

These are all business opportunities which you might be able to leverage in your initial outreach. As always, make sure that the tone is appropriate and doesn’t put down any effort the company might currently be engaging in. But don’t be shy in highlighting the direct value that you could bring in helping them reach further milestones along the way. 

A Little Thinking Can Save a Lot of Grunt Work

For many freelancers, prospecting represents a massive and sometimes very time-consuming effort that detracts from allowing them to do whatever they truly excel at.

However — unless you’re in the position to afford a sales and marketing team — this is a duty that is going to fall squarely on your shoulders (along with balancing the cheques and keeping your computer well-updated). When touting for business, it’s important to couple smarts with hard work. 

Consider asking the above five questions in order to maximize the chance that your communications will fall into inboxes that are likely to be interested in your expression of interest — rather than annoyed by it. 

About the Author

Daniel Rosehill is a Jerusalem-based writer — specializing in long-form thought leadership writing for technology clients. He is also the author of ‘The Confused Freelancer’s Guide to Technology’. For more information, visit:


Share on facebook
Share on twitter
Share on linkedin

Write for Us

Share your experience of freelancing or running a micro business.

Grants List

We've curated a list of grants available around the UK for startups and small business

Most Popular

Something Similar

Related Posts

media enquiry journo request platforms

6 Media Enquiry Services (That are not HARO)

For anyone looking to get a client or their own brands in the press, media enquiry services can be game changing. HARO is probably the most well known, but by no means the only one. So here are some more UK centric alternatives.