Debbie Madden is the founder and CEO of Stride Consulting, a NYC-based agile software development consulting agency. Published in September of 2018, Debbie’s book, Hire Women, An Agile Framework for Hiring and Retaining Women in Tech, was written based on Debbie’s experience building five successful startups from the ground up.

When it comes to building strong, diverse, and agile teams, as well as the brainpower that women in tech add to the equation, Debbie Madden has not only written the book on diversion and inclusivity, she’s personified it in everything she’s done.

In our interview for Future of Work Talk, we talk about why tech teams routinely fail when it comes to hiring and retaining women, why people (and women) leave a job, and how the work environment that companies create is integral to their success when it comes to building diverse, talented teams.

Debbie has thoughts on how women can more rapidly advance their careers in tech, as well as how we can collectively work to get more women in leadership positions.

There’s a reason Debbie has been so successful in the past 20 years. She’s smart, she understands the tenets of great leadership, and she lives in a world where building strong, capable, agile teams and helping businesses leverage software in the most effective manner possible is paramount to success. There’s no one better to learn from about how to embrace inclusion and diversity and how to create environments that allow employees to flourish, grow, and want to stick around. Her book, Hire Women, is a quick read, but well worth the hour you’ll invest in it.

Debbie has contributed to The Wall Street Journal and you’ll also find her writing for Inc., Forbes, as well as her own company blog. You can find Debbie on LinkedIn or on Twitter.


Shelly Kramer: Hey everybody welcome to the Future of Work Talk this afternoon. I am so excited to welcome my guest today, Debbie Madden. Debbie’s the CEO of a company called Stride Consulting, and Stride is a software development consultancy, an agile software development consultancy located in New York City.

Debbie and I were just talking before we started the show on how I stumbled across her, and I think it was because a mutual friend shared some information about a book that Debbie has recently published, stumbling around a little bit today. Her book is called Hire Women: Agile Framework for Hiring and Retaining Women in Tech. I’m sure you don’t have to wonder why Debbie was interesting to me, and why I wanted her on the show today. So Debbie, welcome. It’s great to have you.

Debbie Madden: Yeah, thank you so much. I’m really excited for this conversation.

Shelly Kramer: I am really excited for this conversation as well. So Debbie, you have an interesting story. You’ve spent about 20 years in the tech industry, and really, your company is all about helping your customers’ businesses improve their operations through software.

One of the things I think that I noticed when I was looking at your site is one of the kind of keys to your software offering, is it also pairing your customers with an expert from your team that can lead them down the agile path, because not everybody has that capability in-house. Is that part of your value proposition in terms of what you offer your customers?

Debbie Madden: Yeah, so I appreciate you asking. So Stride Consulting is purely a services business, so we don’t sell any software. We sell people’s time. We essentially have honed an internal process for taking any team, whether it’s the biggest company in the world, to a team just getting started, to oftentimes an innovation branch inside an enterprise.

By literally sitting side by side with both the business and the tech teams helping individuals and teams really understand what best practice in software development looks like. Agile is a word. It is a toolbox. It’s not one size fits all. So we are technical mentors. Also we write code, so we are literally hands on keyboard writing code, so we teach through doing.

Also we’re educating how to have conversations between stake holders and product and technology, so it really is an ongoing process and it’s tailored to the needs of each team, what works for them right now.

Shelly Kramer: Awesome. Okay, well that’s very cool. I think that what I find, we also have many clients in the tech space, and when it comes to technology today, it’s so easy to get seduced by a product and to kind of get lost when it comes to implementation and that sort of thing, so I would assume a lot of the value that you add is the ability to consult on the front end about what the right technology solutions are and then guide through implementation and adoption processes and things like that. Is that the case?

Debbie Madden: Yeah, I can’t tell you how many times we tell people what not to build. You know, everything is strategy, is all about what you’re not doing versus what you are doing, right? That’s such a big part of it.

You can have your highest functioning, agile iterative process inside the code. If you’re building something that no one wants, it’s all kind of useless. We are truly consulting and in software engineering best practices. That includes what to build, in what order, make sure you’re targeting an actual buyer, and then listen, don’t reinvent the wheel. If all you need is video, just copy a YouTube. Don’t build it … you know what I’m saying, don’t try to build it, it’s not valuable to your business.

There’s a lot of talking to humans involved in software development.

Shelly Kramer: Yeah, go figure, right. So let’s talk about diverse teams, diverse and inclusive teams. I know that you are more than a little bit of an expert on that, so I think that we both realize, and we both agree that diverse teams are more effective. They get more done than homogeneous teams, but you know what, we’re not there. We’re not really even close.

So talk a little bit about, talk a little bit if you would about the importance of diverse and inclusive teams, and what you see out there in the market on a day to day basis in terms of how that exists, if that exists, and that sort of thing.

Debbie Madden: Yeah, I think that … that’s a really big question and I can go down a couple paths here. Let’s start with the realities. I do believe that one of the very positive things that I’ve seen come out of all the conversations around diversity, government, Hollywood, tech, I mean, name your industry, and I do believe both technology leaders and employees are … diversity and inclusion is at the forefront of people’s minds, and individuals and teams are trying things, both tried and true things, and innovative things to really increase diversity and increase inclusion.

There’s always gonna be gender bias, and largely it’s under the radar. People don’t even know they’re doing it. There is also blatant harassment stuff, but we’re assuming that we’re really focusing on the people that are good, the people that care, and there’s a lack of inclusion by accident.

The blatant stuff, the best advice I can give to anyone that feels unsafe or not included is to quit your job. I know there are realities and that is a lot easier said than done, but you can vote with your feet sort of thing, and not stand for it.

If you are in technology or in other fields, find yourself a mentor. Find yourself an ally. Do what you can to remove yourself from a situation that’s toxic and unfixable. That’s really the best advice, right?

Shelly Kramer: Right.

Debbie Madden: But for the rest of us, the people that are caring and really trying, I think that what I’ve seen is people are mis-ordering the steps that we need to take to improve the situation.

I don’t like to say fix the problem, because it’s not a yes or no, black or white, but it’s an ongoing evolution to increase diversity and inclusion. The thing that I’ve seen that was kind of light bulb moment for me was increasing diversity and inclusion on teams ends with hiring, it doesn’t start with hiring.

Because think about it, if the team I’m on, if the team you’re on is stinky in any way, whether it’s unfair, it’s unsafe, than what we’re really doing by starting with hiring is asking diverse people to come join a team that we are embarrassed about.

Shelly Kramer: It’s already messed up.

Debbie Madden: Why would we wanna do that?

Shelly Kramer: You’re right.

Debbie Madden: So that’s for me, what I’m seeing. People are trying to recruit women, to recruit minorities, but they’re not addressing the current problems inside their team, and that’s why I wrote the book, to really address some of the core issues.

Shelly Kramer: Well that makes perfect sense. So tell me a brief introduction of the book.

Debbie Madden: Yup. So Hire Women is meant to be a conversation starter. It is literally from start to finish a 40-minute read, and it gives actionable tactics to start to think about how to solve the problem in a way that is iterative.

So it’s not something that’s gonna take 10 hours and you’re gonna have to come back to it in order to get through it. You read the book and it’s, “Oh, I get it. I can do these four things, chip away at it over time to really think about the core team, really create a safe place, eliminate harassment in the workplace, really tackle equal pay in a meaningful way, focus on retention, and then look at the hidden bias inside my hiring and retention process to recruit more people to my team.”

Really, that’s it. It’s not 100-page book. I think it’s under 100 pages. It’s meant to be something the I can take and use in my workplace. It’s geared toward technology, but it’s really applicable.

Shelly Kramer: Applicable. Yeah, it sounds like it’s applibl … applicab … applicable. You ever had a word that just won’t come out? Oh, my God. Sounds like it’s applicable across the board, and something that I know a ton of people will be interested in.

So I love your background, and part of the story that I like may not be the story that you tell, but what were you doing before you decided to write this book? Tell us a little bit about that.

Debbie Madden: So that’s an interesting question because I actually wrote the book Friday mornings, two hours every Friday morning over the course of a year. So while I was writing the book, I am still running Stride Consulting, and continued to do so. That was a really interesting way to write a book, and I don’t advise writing a book this way because it was very hard to keep stopping and starting every single week.

But for me, the book was written from experience from things that I’ve done firsthand with Stride Consulting and with other teams that I’ve worked with. I run a consulting company, so for a living we see inside and underneath the hood of some of the coolest technology teams in the world, and so we get this glimpse that not many people see.

I’ve seen things work. I’ve seen things fall flat on their face. For me, this is a collection of best practices that I’ve experienced firsthand. It was kind of a case study. I was living it as I was writing. This is not an inspirational book. This is a learn-from-failure book.

Over the last 20 years I’ve been running technology teams, and risen through the ranks myself as a leader in tech in a male-dominated field. I’ve seen how I’ve been impacted. I’ve quit jobs over unequal pay, over a couple thousand dollars, just on principle because I felt unvalued. This is a lot of things that I’ve seen and kind of things as a … that I kind of made a promise to myself, any team that I influence over.

I kind of tried to compact it all into … it’s really the tip of the iceberg sort of, a step, right, because you don’t know what’s going on. I write the book and then I talk to women almost every single week, and I hear, “I desperately want to do this, but …”

For me, that’s been the really interesting part of … now that the book is out there, people are trying to apply it. There are realities of enterprise existences, red tape, politics, power struggles, all this stuff.

It’s been really interesting to walk women through one at a time, okay, here’s what I advise in this. Here’s what I need to understand. Here’s some questions for you, ’cause it’s not all do this and things will get … it’s not that.

Shelly Kramer: Right. Every situation kind of has its unique variables I think too. I think that part of your story that resonates with me, I’m a consultant as well, and I’m a brand strategist, so I get to climb inside people’s heads and understand their business, their business model, their target audience, sometimes help them think about things that never occurred to them, pick everything apart, sometimes put it back together. But I think what we consultants don’t do very often, if at all, is tell those stories and what we learn.

I think that’s the fascinating part of what you’ve done. You’ve made time to make this happen. One of the things that I love about your story that I knew as I began to stalk you on the internet a little bit, because of course that’s what you do when someone interests you these days, but you had cancer thrown your way a few years ago.

I really loved how you told the story about what you’ve learned about leadership and about how to be a better leader as a result of dealing with cancer. You wanna tell us about that?

Debbie Madden: I will happily tell you about that, and I appreciate you asking the question. Yeah, a year after starting Stride Consulting I was diagnosed with breast cancer and thankfully I’m cured now, and it was a really interesting year.

It’s fascinating how long the body takes to heal. Throughout this time, starting a [inaudible] startup, tech startup, raising two children, it’s been fascinating. When I entered the start of the journey, I was just worried about getting better, and then in the middle of it, I started to have these moments where wait a second, I didn’t show up to work for a week and this thing happened that was better than I would have done.

All I have is time to think because I can’t do anything else, so I started to really think about why. What did I do differently that was causing these better results by not being there, and then really truly learned how to let go and delegate and trust.

I thought I knew how to do those things before, but really, no. And in truth, I’m still working on that stuff. I still struggle with fully trusting, fully autonomous teams, fully dedicating, and I do believe that that’s something that all of us could always be getting better at, but it was really a very unique way of learning that stuff.

Shelly Kramer: That is a unique, really don’t have a choice way of learning it. That really resonated with me. I’ve owned an agency now for 24 years, so a long time. I am very, very good at building teams, and building teams filled with amazing and amazingly smart people.

I find myself … I don’t think you ever stop learning about how to be a great leader. I don’t think you ever stop learning about … it’s kind of like, I’m also a mom. I have two crops of children. I have daughters that are grown and in their 30s, and I have 12-year-old twin daughters.

One of the things that I’m so aware of, of course it’s easy to be aware of things when you’ve raised one crop of children, but you can’t solve their problems, and you can’t fix everything. I was reading an article about lawn mower parents who … not helicopter parents, but lawn mower parents, who mow down every obstacle that gets in their child’s way. I want my children to have obstacles, and I want them to fail, and I want them to have to get up, and I want them to learn because I’m not gonna be here forever. That’s my job is to teach them to be strong.

I think when you approach leadership in the same way that you approach raising children and you think of it that way, it takes more time. Sure, you could do everything yourself, so could I, but that’s not how you build strong companies, that’s not how you scale companies, that’s not how you grow strong leaders, that’s not how you grow strong teams. It’s not how you make more money.

I think that really resonated with me, that part of your story where you had to step back and through no choice of your own, you had to throw it out there and trust that they would pick it up, and I thought the other part of the story that was really great, was that they did pick up the ball and they never let you down, and they did an amazing job, and your company is stronger as a result. I thought that was really cool. I thought that was a really cool story.

Debbie Madden: Yeah, thanks. And you know, the part about the children is not to be underestimated, because I do think … I also was forced to delegate to my children as well, and they were eight and 10 at the time, and I was basically saying, “Get up. Eat breakfast. Get yourself out to school.” That was terrifying, and guess what?

Shelly Kramer: They did.

Debbie Madden: They did it perfectly.

Shelly Kramer: They did, they did.

Debbie Madden: It was … I don’t wish what I went through on anybody, but I do feel it’s really important to … necessity is the mother of all inventions sort of thing. This is exactly what happened to me. I was forced into a situation, and I’m confident that Stride would not be where it is today, ’cause now we have these amazing leaders that really had to fully own from start to finish and it was all mat for a full you when we were very young, and it’s just been amazing to watch the team grow like that.

Shelly Kramer: Well, and I think that when you empower people regardless of their sex, I know we’re talking about women in tech today, but when you empower people, and when they know that you trust them, and I think as a leader when you can tell yourself that they may get to it by way of a path that’s different than the path that you would have taken, that does not mean it’s a bad path or it’s the wrong path.

I’ve had conversations with people on my team before, even in the last few weeks when somebody would come to me with part of information about, “Well here’s what we did to promote this particular event.” Well, what did that cost? What does that mean that cost per impression that we did?

So you have to look at what is this software cost us on an annual basis and how do we break that up? When you tell people, I feel like I’m constantly telling people including my own children, it’s all about tell the whole story. Having all the information, tell the whole story, looking at the whole thing, but that’s part of leadership. It’s teaching and coaching and mentoring and trusting.

Debbie Madden: Absolutely.

Shelly Kramer: I think that goes a long way. And I think that women in particular, this is my opinion and I don’t know that it’s based on anything based in fact, but I feel like women in particular are very good about, when they know that you trust them, and you trust them to get it done, I think they take that very, very seriously. They are very passionate about wanting to deliver on that front.

I don’t know that men aren’t that way, I just know that the vast majority of my team is comprised of women, and I find that when I throw something out there to them and I am less involved rather than more involved, that they work really, really hard to deliver, and I think to make me happy. Make me proud of them.

Debbie Madden: Yeah, I definitely have seen that, and again I also don’t have any data on that, but I’ve definitely seen that anecdotally. I think if you look at the flip side of that, what I see all the time is … and there is data on, is women have a harder time than men when it comes to getting their idea heard to begin with.

So one of the things that I advised women on my team and outside of stride I often talk about is, there is truth and fact in that, but it does not mean that we victimize ourselves or give up. What it means is we have to create a creative kind of play around it, ’cause on the other side is what you’re talking about.

Once you gain that trust and that support, you can take it to the bank sort of thing, but how can we get more women to that place where they really feel, okay, I’ve been heard. I’m trusted. I can then go execute. For me, the biggest thing that I’ve seen work here is if you are a woman and you want to present an idea to a group, regardless if the group is made up of women or men or mixed gender, it is more likely to be heard and accepted if you share the idea one on one before the meeting.

That’s been a huge game changer I know for me, and for the women that I’ve advised to use this strategy because then you give people time to think about it, give you feedback one on one. You can also do things like, okay, you can appoint a colleague, a man or a woman who has the trust of a team and ask them to support you in the meeting if they agree with you.

I call it building allies outside the boardroom. I think … how can we form tactics along the way to get to that place of trust so that we can then excel in our careers and get those leadership roles.

For me, that’s been a key tactic.

Shelly Kramer: And I think actually, I know that I’ve heard that advice and that tactic before. I think that … it’s funny, it’s so smart, and it’s not something that most of us are accustomed to doing. Again, as you said, it’s being very strategic. Here’s what I’m gonna talk about, and this one and this one and this one are going to be in the meeting, making time in advance, present your idea, maybe even asking for feedback.

That feedback, and integrating that feedback into your presentation because then it’s … and sometimes it’s frustrating that you have to be so strategic as a female presenting a flipping idea, but the reality of it is is that we’re still sort of elbowing our way in no matter that it’s 2018, we’re still elbowing our way in.

We still have people who work for companies that we own who can’t just come out and say, “She’s my boss.”

Debbie Madden: Exactly. Exactly. This is not, to me, a solvable problem. The reality’s … people that are way smarter than me, psychologists have done studies where an aggressive woman at work is seen as a bitch versus aggressive man is seen as successful.

I am the founder and CEO of my company and I still use this strategy with my team, because these are just the realities and I think they are really gonna stay forever more. I think the way to combat them is to work around them. Right, okay, I have an idea, whether or not I’m coming into the meeting with a position of power or not, I still need the buy in of my team. I still need the buy in of those around me, my employees, my customers, the marketplace.

Making your idea a collective one is a really powerful strategy to get ahead, and to succeed with things big or small. It doesn’t have to be earth shattering. If we want to own and move forward, I think this works for it.

Shelly Kramer: No, I think it sounds awesome. I think it’s really smart. So, what haven’t we touched on that might be your final advice to anyone wanting to focus on more inclusion and diversity or more success as a result of those undertakings. Any thoughts … well first of all I’m gonna say anybody listening to this, you totally need to buy Debbie’s book because it’s awesome.

So what would your final thoughts be on what people listening can do?

Debbie Madden: My first piece of advice to everyone, if you care about diversity inclusion in any way, for yourself, for your team, for now, forever. Regardless of where your passions and interests lie, have a goal for yourself that’s within your control. I think a lot of people get discouraged because you try to do the thing that’s up here.

I wanna ensure my company has 50% women by the end of this year. Well, you may have control over that, but you may not. You may have control over a subset of that, and the best way that I’ve seen to enable you to get your objective through, the person who does have that control, does have that power, sit down with them and make it about you, and assure them that what they want is gonna be protected.

So hi Shelly, I have this idea I’m really passionate about, diversity, I would love to do an annual survey census to our employees. I would love to try to increase A by X% in this amount of time. It’s gonna take three hours a week of my time. It’s not gonna cost the company any money, and you have my word that our profit margins, our productivity will not be impacted at all. If it is I promised to reassess and I really would love to talk about that every month with you.

So kind of really frame what you want to achieve, small visible win inside the realm of what the person you’re reporting to, your stakeholder, your customer, feeders, will get impacted negatively. Then just kind of make it an ongoing dialogue.

That for me is the best way to start. And it really doesn’t take more than one or two people to start having these conversations, and then in order to get feedback, I really am available to have these conversations with people. I promise, email me, my email’s literally It couldn’t be easier. It might take three months to get on my calendar, but you know … these conversations, the realities of your life and your workplace are the things that are gonna get in your way. Not the passion, not the interest.

That’s my advice. Start small. Do things that are in your control, and be realistic about how much you can achieve, and then ask for help. I don’t have to be the person you come to. Ask someone that you trust for advice, for feedback. I think if we do this all slowly, slowly, then we’ll make progress.

Shelly Kramer: Well you have your proof of concept. Start small, doing something achievable, and the result will speak for themselves. And then we can bite off a little bit bigger chunk. I think that’s very much how I have to work towards success with our clients no matter what it is we’re doing.

I think sometimes we just get so passionate that we want everything to happen all at once, and it’s really, this is a difficult thing to make happen all at one time, but you can do it.

Well, Debbie, thank you so much for taking time today to chat with me. I really appreciate it. It’s been fun stalking you on the internet. It’s been fun getting to know you in person.

Debbie Madden: Absolutely. I feel the same. Thank you so much for having me. It’s been a real pleasure.

Shelly Kramer: Absolutely. Well, thank you again, and you have a great rest of the day.

Debbie Madden: You too. Thanks.

Shelly Kramer: All right. Bye bye.

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