A Pitching Guide for Geeks

I surprised myself recently. I was doing a last minute prep for a pitch to a health organization near Toronto, it was a joint pitch with another agency, and I remarked to my co-presenter that I was looking forward to the presentation. I believe I actually said, “I enjoy pitching?”

“Really?” was the somewhat surprised remark. I suspect that in many cases most people that start service businesses do so because they enjoy working on the craft that their business supplies - marketing, software development, digital marketing, etc. The craftsperson starts a new business venture and is suddenly put in a position where they have to sell their craft as well as do the work. The vast majority of us would likely rather do the work then be out pitching.

But here I was, actually looking forward to the pitch. I responded simply “Yes, it’s a great opportunity to talk about the great work my team does and how we can help an equally great organization achieve their goals.”

It sounds remarkably simple, doesn’t it?

When I started my career, I was a software developer turned salesperson because I was the most client-oriented person amongst our starting partners. When I started, I was definitely more of a software developer than pitch person, but I have evolved over 15 years of experience. As I’ve evolved into a more experienced pitch person, I have tracked being successful about 50% of the time that I get to the pitching process.

Sometimes the pitch is as strategic as a game of chess

Sometimes the pitch is as strategic as a game of chess


If you’re a “Geek” and enjoy your craft more than pitching, here are some tips for you to consider:

1) The pitch is an evaluation process - for both you and for them

I find a mistake that a lot of businesses (including my own) make is thinking that any work that pays the bills is good work when, in fact, you want to use the pitch and interview process to determine whether your skills and expertise will benefit the prospect and if you can help them.

The most critical part of any evaluation process is the question and answer period. Come prepared with your own questions and listen to what your prospect has to say. Focus on how you or your firm can help the prospect. Asking good questions and exhibiting active listening skills is important, as it shows that you are able to translate your knowledge to fit the unique challenges the prospect is facing. As a caveat, avoid asking leading questions like,“do you like the colour orange,” just so that you can pounce and say, “we do the colour orange the best of anyone,” if the prospect answers, “yes”.

2) Leave lots of times for questions

If a pitch is an hour, and the client gives you 45 minutes for a presentation and 15 minutes for questions, aim for your presentation to be 20-30 minutes max. The presentation can be used as a baseline expectation of your skillset and to assure the prospect that you have the skills to do the work; but the true connections happen during questions, answers and corresponding dialogue.

No matter how impressive your powerpoint, video or portfolio is, people do not buy from presentations; people buy from people. Be present for questions. If the prospect does not ask a lot of questions, use that time to ask them questions, per the point above.

3) Be authentic

Clients can pick up on overly salesy language or tactics. Unless you’re a very experienced sales person that can pull off some of the more advanced maneuvers, be yourself. Know your craft inside and out and be confident in you and your team.

Over the years I have attended hundreds of sales seminars, peer groups and presentations that talk about the ways to advance a prospect to a close. I find that many of these run counter to the value of craftspeople who just want to do good work and provide value for the client.

Speak clearly, articulate your value proposition and trust that you have a valuable skillset that your prospect needs. If you’re right, the bid will go your way.

4) Enjoy the process

You’re getting to meet a new group of people who need the type of product or service that you provide. You’ve got a great team behind you that you know can do the work. Your job is to present you and your team in the best possible light, and to create meaningful connections with other human beings.

Too frequently we go into the pitch process with a sense of desperation, that we need this sale to meet quota (or if you’re a startup to make payroll or your mortgage payment). However, if you go in with unreasonable expectations you will bring that into your presentation, tone and evaluation of the outcome.

5) Ask for feedback

Whether you win or lose, always ask for feedback on your presentation and proposal to find out what you can do better next time. It may be counter-intuitive to do this when you win the proposal, but I’ve found that the best feedback has come from the opportunities we’ve won versus those that we lost.

6) Accept the outcome

It is sometimes very hard to lose an opportunity, particularly one you’re passionate about, to another supplier. If you believe that your team is a great fit for the organization, and that the organization is a great fit for your team, it can be a great disappointment to not be able to connect the two teams.

However, losing is part of the process. If you’re starting out or new to pitching, it doesn’t necessarily get easier, but it becomes acceptable. Trust that the processes that bring you work and make new clients is working; and conversely those that do not bring you positive results also worked.

Being a craft person doing pitching can be a challenge, but it can be eventually something that you come around to enjoy. If I missed any tips feel free to add them below!

David Billson