How I Turned Two Rejections By Microsoft Into A Successful Career There

Before retiring as a managing partner at Microsoft, George Santino heard “no” more than most.

How I Turned Two Rejections By Microsoft Into A Successful Career There
[Photo: Flickr user Frédéric BISSON]

The first time I sent my résumé to Microsoft, I got the standard, “Thanks, but no thanks,” form letter within just a few days. So I gave them a call.


I just wanted to know why I’d been rejected. When I spoke to the human resources contact at Microsoft whom I’d sent my application to, I was told I didn’t meet the job’s qualifications: I didn’t have a college degree. Neither did Bill Gates, I replied, and nor did the founders of a handful of other leading tech companies cropping up at the time.

And just like that, I’d turned a “no” into an interview.

How To Hear “No”—Repeatedly

That interview didn’t guarantee I’d get the job, of course. In fact, I ended up getting the same form letter telling me again, “Thanks, but no thanks.” So I picked up the phone again.

Persistence is sometimes the fastest way to irritate people, but in this case it paid off. It occurred to me that the position I’d just interviewed for officially required five years of Windows testing experience. I had two.

But I’d done my homework: I knew when Windows was first released, and until Windows 3.0 came out, there weren’t a lot of companies building software for it. Ashton-Tate, the software company where I was working at the time, was one of just a few that were developing a product for Windows. We’d only been working on it for two years, not the five Microsoft was looking for. But I was able to point out to the hiring manager that the product she was working on was first developed for Windows 3.0; before that, it had been a Mac product, so she and her team didn’t really have five years of Windows testing experience, either.

That discussion got me an invitation for a second interview, and to make a long story short, I wound up landing the job at Microsoft, and retiring after a long and successful career as a managing partner.


When Rejection Is An Opportunity (And When It Isn’t)

In some situations (dating, for instance), getting rejected really is a hard “no.” But that’s seldom the case in many business scenarios that hinge on human interaction–like negotiations, sales, or even interviews. Sometimes “no” means “tell me more,” even if the person who’s just told you “no” genuinely thinks they’ve heard all they need. At any rate, that’s the mind-set it takes in order to close the deal, make the sale, or get the job–or at least land another interview.

I should know: Before getting into software development, I was an insurance salesman. I heard “no” a lot. Whether it was during a cold call on the phone or after a sales call in someone’s house, I heard that monosyllable all the time–so much, in fact, that I started to dread making the call or going to the appointment. But over time, I realized that I was actually getting more sales from the people who’d rejected me outright than from those who’s said nothing at all: the ones who thanked me for my time and sent me on my way were the real rejections, but the others weren’t.

By asking “why” after hearing “no,” I learned that the reason for the initial rejection was sometimes easy to overcome. Even in the cases when it wasn’t, I typically gained some sort of insight based on that feedback. That could change my next sales pitch or alter my approach so I had a better shot at a “yes” from the next person I spoke to.

How To Ask “Why”

Interviewing for a job is really just another negotiation or sales meeting. You send in a résumé, and you either get an interview or a “no, thanks.” They key is not to walk away defeated from that rejection, but to find a way to ask why. Here are a few steps to take in order to do that.

1. Get to the “why” as quickly as you can. You have to know the basis of the rejection before you can overcome it, and for that there’s no time like the present. Sometimes the hiring manager who’s rejected you hasn’t planned to explain their rationale and can be taken aback, but you’re more likely to learn something useful if you frame your request as constructive feedback.

Call or email your contact and simply say you’d like to understand the reason they didn’t feel you were a great fit. Say you’d like to learn from it so you can take it into account as you continue your job search. If you’re turned down in a face-to-face situation (less common, but it happens), politely ask why, right then and there.


2. Find out what’s missing. Ask what experiences or skills they believe you lack. This can not only give you a helpful sense of how your own expertise is perceived, but also how the hiring manager is envisioning the ideal candidate. There may be some other way for you to fill in the gap that your prospective employer hasn’t accounted for.

3. Answer those questions in a way that’s fitted to the objection. You can’t always change someone’s mind, but you can always offer more information. Here are some examples:

As a matter of fact, I do have that experience, just not from my current position. But previously, I ____________.

You’re right, I don’t have that exact experience, but I think what I’ve done in ____________ is relevant because ____________.

That’s a good point, but I believe this similar skill of mine would still be applicable because ____________, and it would make a great foundation for me to pick up the skill you’re looking for very quickly.

It’s frankly easier to accept “no” and walk away. Standing your ground, asking to learn why, and advocating for yourself is pretty uncomfortable. You may feel out of line, unprofessional, or arrogant. But as long as you frame your requests in terms of a genuine desire to learn more–about what you can do differently, and your prospective employer’s needs–you stand a better shot at turning that rejection around.

Some people won’t tell you more, but nobody will if you don’t ask them to.

George A. Santino is the author of the forthcoming Get Back Up: From the Streets to Microsoft Suites. Follow him on Twitter at @georgeasantino.