Why Underpromising and Overdelivering is Only Half Right

You’ve probably heard that one of the keys to success is to “underpromise and overdeliver.” But I think that only the second half of that statement is actually good advice.

Underpromising will never win you clients or get you a job or a promotion. You should be aware of what you are capable of doing and convince others that you can deliver. Once you’ve been given an opportunity, you have to make good on your promises — and then some. Overdelivering once you get that initial opportunity is the way to retain clients, expand your scope of work, and build a reputation that will serve you well for years to come.

This is especially important if you have someone helping open doors for you. In life, as in business, relationships matter. So often, opportunities are realized not just through our own efforts, but through the support or recommendation of others. As someone who has been helped by people who believed in me enough to bet their own name and political capital on my success, and as someone who is often asked to do the same for others, I know how important it is to not only live up to those expectations, but also to surpass them. In short, my advice to you is: overdeliver.

This is a lesson that applies to individual and business relationships alike. In business, you often hear about the importance of seeking out mentors to guide you through challenges, but there’s a distinction between a mentor and a sponsor. Mentors are important, but sponsors are vital. A sponsor is someone who believes in you enough to promote you and your career using their own resources, including their political capital. A sponsor is someone who has achieved much more than you and is placing their own reputation at stake to help you accomplish something that you might not be able to achieve without them. In many such cases, you may only get one shot at the opportunity.

How do you repay someone like that?

One word: Overdelivering.

When someone sticks their neck out for you or your business, you need to go above and beyond everyone’s expectations to make your sponsor look good. Never give them a reason to regret having put their stamp of approval on you or your business.

An oft-cited illustration of this point involves the difficult times Pinnacle Group went through after 9/11. This was an incredibly difficult time for the country and a huge tragedy for so many people. It also impacted many companies, including Pinnacle. We almost went out of business, but we knew we could pull through if we buckled down and got creative about our approach to business in this new environment. Working through the challenges of turning our business around was not easy, and success was not imminent. We responded to over 40 RFPs and only won two in that time period. When we finally got the chance to impress a new partner, what did we do? We overdelivered. We did our work at such a high level and with such dedication that the client couldn’t help but continue working with us (and they still do almost 20 years later).

I use the phrase “crazy good” to describe my philosophy in both business and life. What it means is: whatever you do, be crazy good at it. The idea of being crazy good directly ties in with the concept of overdelivering. When someone chooses your business, or when they offer you an opportunity, they are saying that they believe you are truly exceptional. They think you are crazy good at what you do. Now, imagine if you rewarded their faith in you by doing your work in a disinterested manner or only doing the bare minimum. It would be an absolute waste of your time, as well as the efforts of your sponsor and a squandered opportunity with a potential client.

Instead, be “crazy good.” For example, if you’re given an opportunity by a sponsor and you are asked to write an essay or cover letter for that project, don’t just write a generic letter or haphazardly put together a few paragraphs. Take the time to write the very best essay or cover letter you’ve ever written. Even if you don’t get chosen for this opportunity, you will have rewarded yourself and your sponsor by putting your absolute best effort into the project. And when another opportunity comes along, you’ll have a higher likelihood of your sponsor supporting you again.

Every time someone has given Pinnacle Group an opportunity, we have overdelivered on what we have been asked to do. In doing so, we are making our sponsors (and advocates) look good to their own companies. And, of course, it pays off for us as a business as it also allows us to establish long-held and valuable business relationships.

Finally, another way to overdeliver is through volunteer work in your community and philanthropy in areas that you are passionate about. But beware, no one appreciates superficial attempts to give back done solely to make you or your company look good. People can see through these cynical and lazy attempts, and more often than not, they don’t reflect well on you. If you’re going to get involved in something, get really involved. Be passionate. Be crazy good at it. This is how real change is affected in communities.

And in the case of philanthropy, you aren’t overdelivering for the benefit of yourself or your career, you are overdelivering for the benefit of others. The rewards will be in the betterment of your community, and, frankly, there’s no greater reward than that.

You will never regret overdelivering in any situation, but you may live to regret times where you could have done more. In other words, do everything you can to be crazy good at everything you do!