December 14, 2016

A fieldguide for independent strategy consultants

Some collected thoughts

I’ve been enjoying writing posts recently that are more collections of half-formed thoughts than complete works and so I’m going to do it again with this post. What follows is an outline, or a collection of conversation starters, for digital strategy consulting.

A few close friends of mine are considering making the leap into becoming freelance consultants and so I wanted to provide some pointers.

Before I dive in though - I want to really reinforce the idea that if you don’t have a strong referral network, being freelance may not be the right path. I’ve seen people manufacture networks from scratch (through blogging, extreme participation in communities etc) but it’s hard! Most successful consultants have some kind of network pre-built.

If you do have a network, then the second most important thing is to build some trust totems - be it conference speaking, previous companies worked at, case studies, books published or whatever. Something that allows people to say “I want to work with that person and I believe they will do a good job”.

With those out of the way - here’s some collected notes:

Finding Clients

90% of your clients will come through your referral network (see above!)

Personally I prefer to work directly with clients but I know successful folks probably earning more than me who depend on leads from other sources (such as other freelancers and agencies) and give kickbacks.

The best marketing you can do is to a) stay top of mind for your referral network (be visible, blog etc) and b) help define for them what it is you do (and/or want to be doing).

Create a community around yourself. Seek out likeminded independents, seek out others in the industry, host roundtable discussions, host breakfast meetings, start an email list or a slack group. Starting is infinitely better than joining, but if you have to join at least make sure you contribute instead of just lurking.

Respond fast to all inbound leads but be prepared for leads to take 3+ months to close.

A well written email outlining what the core problems are and how you’d address them with two options for pricing will outperform a pitch deck most days of the week. (See how to write a short proposal from Alan Weiss and his collected examples)


Heading out on your own you’ll likely have ideas about what kind of work you want to be doing. But you probably won’t be able to get there straight away - it took me 12-18 months before I was starting to do the really interesting work I dreamed of when I quit my job.

For your first 6 months focus on paying the bills rather than worrying about the type of work you’re doing. Patience.

Don’t be afraid to meander through conversations with leads - I’ve often had wide ranging conversations before deciding on a specific project to work on with a client.

That said, once you have some clarity clear positioning is effective - even if it’s in your own head. Try outlining the kind of companies you’re best able to help and the best kind of work you want to do. (See my latest positioning in this post)

Start a company and a brand. Or don’t. Up to you - I know folks doing it both ways. I decided not to, but the decision is personal.


It’s ok to meander through client calls (as I mentioned above) but one thing you should have a clear idea about is pricing. It looks somewhat amateur to say “I’ll get back to with my day rate”. You should have that at your fingertips and state your price with confidence.

Don’t be ashamed of stating pricing. Invoice with confidence.

Everyone says you should charge project based fees. They’re probably right and I’ve included many project based prices in my proposals but ultimately almost all of my work is done on a retainer basis (ultimately tied to hours/days more or less closely). You can make a very healthy living on day-rate based work so don’t fret about all those people telling you you’re wrong. Patience.

Asking for money is weird. But you’ll get over it.

I’ve personally been very lucky with clients paying their bills on time but almost everyone I know struggles with this so always factor in getting paid late.

When a client isn’t paying their bills get a direct contact in accounts and raise hell. Don’t be nice.

My invoice template is a simple Google Doc and my accounting is a spreadsheet. Don’t overcomplicate the mechanics and admin of your business.

Doing the Work

You can’t solve problems from 10,000ft. Get close enough to smell the client - get onsite, get invited to their slack, get integrated into basecamp, start conversations, chit chat, look in analytics.

Never write a document for the sake of it - focus relentlessly on the output you’re aiming for and always ask yourself if you can skip the document and get to the end result.

Think about running workshops. They’re very effective tools (secret: a workshop is just a fancy name for a meeting but usually has better results).

Be comfortable switching between presentations, spreadsheets and docs (and of course slack, email and basecamp). You’ll have to straddle multiple modes and lower switching costs to be effective across multiple clients throughout a working week.

Learn how to make basic prototypes - whether that’s in code or design. Showing a sketch of a finished thing is far more powerful than talking about it in a presentation.

Communication solves all problems. Communicate liberally with your client.

If you’re charging a “high” day rate don’t be afraid to roll up your sleeves and do the work. The last thing someone wants is a consultant who’s all talk but won’t get stuck in.

Obsess about plugging gaps in your client’s organization. If there’s a report that they’re not looking at - don’t tell them about it, but make it (or an mvp anyway) and send it to them. There’s nothing leadership loves more than initiative. The classic failure mode of employees is thinking they don’t have permission or ownership to get something done. Your magic as a consultant is no permission, no ownership but a blank canvas.

Every organization has a “grain”. Realize you can’t work against the grain without exceptional circumstances - so understand why that grain exists in the first place.

Remember you know less about the client’s business than they do. Be humble. Ask a lot of questions.


Always be growing, don’t get complacent with clients, leads or revenue.

Many clients will likely want to hire you fulltime. Be prepared to resist or else face a rollercoaster of emotions every single project.

Focus. Don’t try and productize your work or start a startup before you’re comfortably paying the bills and settled into a groove.

Never settle into a groove.

Find a support network. There will be emotional rollercoasters.

When client work gets quiet - make the most of it. Go bike riding, play with your kids, read a book. When client work gets busy there’s no one to do the work but you so you’ll work evenings and weekends so take the time off when you can!


Start an LLC. It’s really not hard. Keep business spending and personal spending separate. When you start earning real money consider filing taxes as a C-corp (which you can still do as an LLC).

Get an accountant.

Keep costs low. 2016 for me right now is operating at 98% margin. Paying for things can feel nice but you should question if you absolutely need them - coworking space, accounting software, facebook ads, business cards - all not entirely necessary so ask yourself before you spend.

That said - spending on gifts for professional contacts, dinner with industry friends and so on is always worth the money. Do it liberally and often.

I’ll probably add to this list and expand some of the points into full blog posts over time. What did I miss? Drop questions or add your own ideas into the comments below!

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This post was written by Tom Critchlow - blogger and independent consultant. Subscribe to join my occassional newsletter: