Influential Women in CX: Aileen Allkins Shares Her Journey from Front-Line Agent to Microsoft Corporate VP of Customer Service and Support

We are thrilled to continue our Influential Women in CX series with a two-part feature on Aileen Allkins, who currently serves as Microsoft’s Corporate Vice President of Customer Service and Support.

In part one of our interview below, Aileen shares her journey to becoming CVP at a Fortune 100 company where she is responsible for an international team of 25,000 employees. Underscoring her high degree of empathy for others, she explains why people are her favorite aspect of her job and why angry customers don’t bother her.

(Please note that the following interview has been edited for length and clarity.)

How did you get started in customer service and support?

I wonder how many people leave school saying, “I know what I really want to do. I want to be in customer support.”

For me, the path to support was through training. My first roles in IT companies were before the days of Windows. There were no mice; nobody had used a word processor or a spreadsheet. But somehow I just completely clicked with using these applications.

I went from being a trainer to leading a small training department. And as the company grew, we started getting more and more customers phoning in for support. So the company asked if I would set up a support team as well.

The next company I worked for was looking for a support leader. So I decided that, as much as I loved training, I would stick with support. And ever since then, pretty much my entire career has been in support at software companies.

What is your educational background?

Eight or nine years ago, I was doing a keynote for connected women in technology in Rome and as part of my talk, I shared that my formal education had ended when I graduated from high school at the age of 16.

Everyone in the audience kind of gasped. But afterwards, I was surrounded by women who confided, “I didn’t go to college either. But I’ve never wanted to say that because I was worried that people would look down on me.”

My parents couldn’t afford for me to go to university. When I finished high school, I initially got a job working for the Ministry of Defense in the UK, which is where I’m from. Then through a bizarre coincidence, a family friend was working at one of these very early stage computer companies, and that’s where I got my first job as a trainer.

It wasn’t until I started being engaged with American companies that I became aware that what college or university you went to meant something. In the UK, it never really mattered. But when I began working with US companies, I became aware of the importance of where you went to school and became very self-conscious. And I would avoid that conversation for a long time.

So that moment on stage in Rome where I publicly shared that I hadn’t gone to university was massively liberating. Afterwards, I felt ashamed of myself for not being more transparent sooner because of the number of women who were inspired by it.

I learned that we should be much more open because, in the grand scheme of things, people don’t care about things as much as we think they will.

Turning now to your current role at Microsoft, what is a typical work week like for you?

Invariably there is some form of customer escalation over the course of any given day. In fact, just before this interview started, I had an email from a customer land in my inbox.

I can spend my time like I’ve done this week in meetings with finance. I manage a huge budget of over $2 billion. So I’m looking to see: are we spending that most effectively, are we going to have enough money for what we need to do, or are we going to have surplus money, which believe it or not does happen occasionally. Also, we begin planning about eight months ahead of the new financial year, so there’s always a lot to be discussed on the financial side.

I manage 25,000 people who all have access to customer data, so security and privacy are always top of mind from both a people and tooling point of view. A lot of that work is outsourced, so I spend time working with our outsource partners. Next week, for example, I’ll spend two days with those partners and their executives where we’ll go through our strategy, sharing our best practices and learning a lot from them as well.

Of course, we do the usual business reviews on all of our metrics and how we’re performing. And then I spend a lot of time in front of people.

Last week, for instance, I spent an hour with the HR organization that looks after our field teams. I’ve got 700 managers in my organization, so once a month I have some time with them on a call. Then we have a couple of hundred additional people that we call senior leaders that I speak with regularly. So I spend a lot of time communicating and listening.

That’s just to mention a few things; it’s completely varied from customers to business reviews, finance to legal, security and privacy, and then the part that is most enjoyable is actually when I’m with people.

You mentioned that the aspect of your job that you enjoy most is the people. Can you expand on that?

First of all, my own team. I love spending time with them because you learn so much, especially when you sit with those on the front lines.

Recently, I had all of my 700 managers in town for a whole week. We do that once a year, and I can tell you there were tears of joy. People were sharing stories about what they’re proud of doing and about the impact they’ve had with Microsoft, which is a company that’s very good at making a difference and giving. Seeing how proud my team is of what we’re achieving is personally so, so rewarding.

Spending time with customers is a very different scenario because typically those that I interact with are not happy. But what I do find very rewarding about those situations is being able to help resolve a problem and create a positive outcome.

For example, I recently dealt with a very, very angry customer who had emailed pretty much every executive that he could find with the subject line “The worst support ever.” Yesterday, that same customer sent another email saying, “OK, I take it back. Your team has been absolutely incredible.” To see my team convert a customer who was so unhappy to now saying, “I take it all back. The product is great.” is incredibly rewarding.

I also love spending time with my peers in the industry — just sharing stories and best practices and understanding what they’re doing. I think if I could find a job where I spent 90 percent of my time not in meetings and not on email but just with people, then I’d be extremely happy.

What do you find most challenging about your job? Is it those very, very angry customers?

Actually I don’t find angry customers challenging at all. Having been in support for over 30 years, one of the things I’ve become particularly good at is having empathy. I always think about the level of frustration the customer must be feeling to get that angry.

I never take it personally, and I always try and coach my team to think about what’s going on for that customer. To think about how it feels when something has gone wrong with the product, and they need support. And how frustrating it is when they can’t get a solution to their problem straightaway.

Instead what I find the hardest in the world of support is that we exist because things go wrong. After all, if the products were perfect, never had bugs, and were completely intuitive, then we wouldn’t need to be here.

Unfortunately, support departments often only get noticed when they get something wrong. So you can deal with 1000 cases in a day, and 999 of them go really well, and you get great survey feedback. But then on one of them, you screw up in a big way. Or you don’t screw up, but you just can’t resolve it for the customer and it gets escalated. Then everybody in your organization only hears about that one case, not the 999 that went well.

I think that’s the hardest — when I see the great work that people do and how hard the job is, and internally sometimes people can really jump on them in a negative way. There’s often a lack of empathy internally for what people on the front lines are trying to do. So I find that to be something I grapple with and find frustrating.

Then, on the reverse side of that, if you try to promote all the good stuff that you’re doing, you’ve got to be careful that you’re not coming across as being oblivious to the fact that you’ve always got more to do, and you can always do better than you are currently.

Given the typical focus on the negative that you described, what strategies do you use to celebrate successes and keep employee morale high?

At every company I’ve worked for where I’ve run support, the first thing I’ve always done is put a team in place to focus on people. It never exists when I’ve joined, and I create it for exactly this reason.

We get over 60 million support cases a year. We can’t read all of those customer surveys manually, so we use technology to scan them. What we’re looking for is customer sentiment, and we have the ability to identify sentiment linked to certain behaviors. We’re trying to focus our front-line agents on how they behave, such as showing empathy with customers, demonstrating listening skills, and creative solutioning.

Then we created what we call the “customer hero program.” If our machine learning model identifies one of these sorts of behaviors based on customer feedback, then the agent gets a corresponding customer hero badge for that behavior. We then publicize the program every week in an email newsletter featuring three people who received badges.

Those three people then get magnified massively because each person is on somebody’s team, so the team is proud to see their teammate acknowledged. And then the whole site — which might have 1,000 people — realizes that somebody from their site has been recognized and feels proud.

Do you have any additional examples of ways you empower your support employees?

We also created an ambassador program. Across my whole organization, I’ve got about 700 people who are self-nominated to be program ambassadors.

The purpose is to have representatives of our front-line agents and managers who tell us what we need to do, what the problems are, and what the potential solutions are. Then we will go as a corporate head office and make it happen. Instantly when we do that, people feel that their voices are heard. And they don’t just feel it, their voices are heard.

The ambassadors represent a community of support engineers either by product line or for a site. It is then their responsibility to share the updates on the initiatives back to the community they are representing. Because oftentimes we were finding that people would not know what we were working on their behalf.

The ambassador program has been going for about three years now, and it is really, really impactful.

You’ve talked about ways to empower your front-line agents. How about your managers?

We had all of our managers together for three days a couple of months ago. We spent the first morning on Making a Difference, which is very important to Microsoft and one of our cultural attributes.

We had nine different charities present, and our managers designed socks for these charities through a small Microsoft customer called John’s Crazy Socks in New Jersey. The whole morning gave people a feeling of purpose and just this massive motivation that comes from working for a great company.

Then we focused on coaching, with Michael Bungay Stanier, founder of Box of Crayons, a leadership coaching company. There was not one single slide for a three-hour session on coaching others and being coached yourself. And finally, we had another keynote speaker, Shawn Achor, NY Times bestselling author of The Happiness Advantage and Big Potential, who spent a couple of hours talking about happiness and again not one single slide.

The feedback we received from the managers was incredible. Just the fact that we took three days to invest in them as human beings — coaching, happiness, making a difference. Things people could take outside of the workplace.

It was all about making them think differently about caring for themselves with the belief that they will bring a better version of themselves to work. They will care more for others if they care more for themselves.

Stay Tuned for Part Two

You can learn more by following Aileen on LinkedIn. And please stay tuned for part two of our feature on her, as well as future interviews with CX superstars.