How do you decide what to hold back?

Lewis Cowles

I’ve been thinking a lot lately about the processes for my business. I just completed some basic research for a potential new client on-board and it made me want to ask a long-form question. Instead of posting that anonymously online, I’d like to tell you a bit about my process, and then ask some questions, which hopefully some will answer.

I have a process that is non-trivial in on-boarding new business clients in a (perhaps mistaken) view that it should help avoid mistakes of the past, lead to happier outcomes and more successful clients. Since 2014 it’s been helping.

Image courtesy of — user: Tero Vesalinen

Most of my new client accounts are not likely to bring in a large amount of margin for a while. It’s all quite long-tail, generally it’s nice if we can break even year 1. The clients that I want to work with are nice people struggling with technology, with goals I support.

In the case of the business that triggered this post. They want to source and provide ethically sourced products. I’m good with that deal. Helping with missions like that makes my cogs turn, it makes me want to help them and do my best.


Quite a lot of my initial contact is copy-pasta. You’re not going to send a 20-page document outlining the next 5 years of a business you barely know. That is a task in itself and smarter people than me have written about avoiding spec-work. — don’t believe me, check it out.


My purpose is to respond professionally and show potential clients, I want their business. It has to be done by a person in response to information provided. That is one of my early requirements, so I’ll generally ask them some things off-hand, but on-topic before responding to too many specific details.

Saving Time

I use templates to speed up this process. It’s not from a single template, and I’d be lying if I said I never write anything personalised, despite the goal being as little personalised as possible. I’m sure we all do this. It requires up-front effort & domain knowledge. It’s not something you could cobble together from a blog article.

This is not something I’ve worked out how to automate. I’d rather put in the effort than get it wrong automatically

Some of the initial contact resources referenced by potential new on-boards communicate vision and goals. Some people prefer to do that in a meeting, but for me that has always been a terrible way to waste time. You’ll turn up, they’ll talk, you’ll talk, but at this stage it’s premature. They need to have a reason to trust you, and to share with you without “flinging jelly” — Book


I do things like checkout highlighted competitor technologies, features, areas for improvement and where possible I use company numbers to get an idea of the size and maturity of competitors. It’s like painting a picture, you start with the big blocky parts and then fill in more details, refining as you go.

For one client I did this for today, there was a £4.3M competitor in the space they intend to enter, with a wide range of products, mature digital presence and lots of tooling. They had highlighted this competitor, which will obviously be hard to challenge or imitate without budget.

The good news is that it proves a market size and potential, which is part of my tick-list. I want to help people succeed and without evidence or some very strong emotions I find it hard to justify working with people. This research is as-much for me, as them. It’s also reusable

Image courtesy of — user: Pexels

Getting personal

I also checkout social-media, reviews, existing public assets (with the help of tooling). My tooling can serve a range of purposes and checking out a bigger picture might bring up more high value items than the initial brief. Because of this breadth, I use a range of resources, most of which depend on the type of contract because my business covers three main areas of technology expertise.

In the case of the business I’ve spoken about, it’s e-commerce web-focused work, so I used the following public tools:

Even if it’s a software product I’m building, this helps me to understand as much of a picture about a client business and market as is reasonably possible in an early-contact situation. I’m not locked to a vertical like some competitors, although a lot of people wanting e-commerce work from me do work in fashion or with fabrics.

Poor results thrive on poor decisions and lack of planning. The more planning you do alongside decision-making, that should increase the odds that you achieve success.


One of the concerns I have when responding is context. It’s hard to get context right. Pitch to a regional business about integrating their tools and it might solidify you as a go-to-person who has been here before and understands their challenges. A national or international business may have that tooling (and if you don’t, get in touch). Asking questions, like “Have you considered roadmaping some features for later?” Can help you understand the discipline of the contact you’re dealing with, as well as the priority of works.

Also what is and isn’t within the vision or budget of the people you’re trying to help is important. Don’t decide you know better, even if your initial research says {X} is an opportunity, it’s their business and they probably know, or feel they know the direction.

Image courtesy of — user: 825545 (perhaps a robot or Alexa skill?)

I try to ensure not just that I’m doing a good job, but that it’s not too much for the size of business.

When we hear about other companies in press-releases and wider news, so much context is missing.

To take an example from technology. Facebook invents some JavaScript to enforce standards in front-end projects. Google does the same thing (years earlier).

An amateur may conclude every business has to follow the leviathans. An Expert can look at these things and if they are not dealing with a huge multinational, or a business with the problems the tool fixes, then they’ll know when to stand up and take notice, investigate further, and when to simply shrug.

When tools become a swiss army knife, costs balloon. The truth is that more of us don’t work for a Facebook or a Google than do. Be careful what you focus on.

Setting expectations

Where a large competitor is highlighted, I’ll do my best to set expectations of that competitors budget from public figures, contacts, or admittedly sometimes guess work. “What it would cost for me to do that?” is a good fallback, and an honest way to communicate failing available information.

Once this is all done, I’ll send them an email, and if I’ve got a phone number, I’ll call or text before sending to discuss a meeting and let them know a mail is coming. It’s important to not be too far removed, and admittedly working for a lot of businesses abroad, this can be a challenge or pain point not being able to block out a short time window, or a series of them to go over and agree to work together.

Image courtesy of — user: rawpixel

What about you?

I’m getting to the end of my talk / rant on this now, so time for some questions. Hopefully it’s given an insight to my process, but perhaps it’s different to yours. I’d love to hear from you!

  • Do I make a rod for my own back?
  • Is there more I could or should do before an initial client meeting?
  • Should this level of detail lead to me excluding some new businesses?

I don’t know is the only answer I can give honestly.

I both enjoy my approach and can point to instances where it’s helped me.

I Still worry it may be an area of waste, where I might as well do other things. If I’m honest for a while I didn’t need or take on new customer accounts and internally there is a feeling that growing with clients is a situation I’d prefer. Perhaps a product role would simplify.

I try to tailor each on-boarding to the client rather than boxing them into some corporate one-size-fits none plan.

I guess I’ll finish on the most important question. I Hope you don’t mind the avoidance of easy answers.

How do you decide what to hold back?

Lewis Cowles

Written by

Digital Architect & Owner - UK-based I.T. Consultancy.I make things happen and could probably help you deliver software & experiences

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