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Building High-Performance Teams Through DISC with Stephanie Windsor, CEO Cloud Benefits

• Amplified Group • Season 6 • Episode 12

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What happens when a promising startup faces challenges that threaten its very existence? For Stephanie Windsor, CEO of Cloud Benefits, the answer lay in understanding the diverse strengths of her leadership team through DISC profiling.

Founded in 2021 as businesses emerged from the pandemic, Cloud Benefits offers a digital employee benefits platform with unique features like free financial advice and animated benefit explanations. But by mid-2023, despite positive market feedback, communication breakdowns threatened their progress. The leadership team—who remarkably had never met in person—struggled to collaborate effectively as summer targets loomed.

In this revealing conversation, Stephanie shares how she personally funded DISC profiling sessions with Amplified Group when company finances were tight, convinced this investment would transform team dynamics. The results were extraordinary: team members gained profound insights into their communication styles, working preferences, and natural strengths. Rather than forcing everyone into predetermined roles, 

Stephanie's conviction paid off dramatically as the team exceeded their targets following the sessions. Now, as Cloud Benefits enters a new growth phase, they're scheduling follow-up workshops to maintain this momentum. 

This conversation might just change how you think about team performance forever.

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Sam:

Welcome to Get Amplified the podcast about teamwork in the tech industry. Well, it is a glorious, is it spring? Spring, probably spring day. Today the mist has burnt off. I'm hoping it's going to get up, maybe even into double digits today. Vicky, what's the weather looking like in deepest darkest?

Sam:

Vicky, what's the weather looking like in deepest, darkest Oxfordshire?

Sam:

VIC, the weather is beautiful. Thank you, fab. Not that we need today brightening, but we're going to have it brightened.

Vic:

So we've got a very special guest, and it's actually a client of ours, so we've got with us Stephanie Windsor. So Steph is the founding partner and CEO of Cloud Benefits. We worked with Steph back in May 23, and we're just about to kick off some more work, though, which is very exciting. You might be able to tell by my voice, I am in la la land, I'm afraid, more than usual, sam, before you say anything, so I'm gonna stick myself on mute for most of this, if you don't mind, and leave you two wonderful people to it for our listeners.

Sam:

That's not because uh vicky has ingested some sort of illicit substance. She, she's very ill with the lurgy.

Steph:

Thank you for inviting me along, you're very welcome.

Sam:

It's great to have you on board. Maybe, if you don't mind, you could start by giving us a potted history of your illustrious career to date. Bring our listeners up to speed.

Steph:

Of course. So I started my career over 30 years ago working for one of the largest employee benefit companies in the world, and I ran national sales for that company for a significant amount of time and worked with and led teams and found that I love to work with people and loved providing really great employee propositions. But all those years ago I thought, do you know what It'd be great to do it differently. And so, 30 years later, I started a business and we started it in 2021. So, just coming out of that COVID period and our proposition is a digital employee benefits proposition, we're the only employee benefit company that provide free financial advice and free mortgage advice and free tax advice to all of the employees of the employers we look after and their partners as well, and our goal is to use technology to link the benefits that a company provides to an individual's personal objectives and their personal policies. And we also explain benefits very differently. So instead of lots of text, heavy information, we provide short animated benefit explainers. So we have a really multi-disciplinary teams. You know, we have people who do amazing animations and we have people that do risk broking and we have people that do pension consultancy, but all very people focused yeah, okay, that's interesting it's like a you know, a fresh, modern approach to to employee benefits absolutely absolutely

Steph:

and about making things more relevant and how's the business going? Oh, it's going from strength to strength really. That's good to hear, but we reached out to vicky and her I was going to say you've had vicky and the team in helping you out, haven't you?

Sam:

yeah, absolutely yeah and you're a massive subscriber to this disc shenanigans that Vicky talked about a lot.

Steph:

Absolutely Now. I first heard. Disc a very long time ago, and what DISC does is help build amazingly high-performing teams. I think it's very easy, as an entrepreneur or somebody who builds teams, to want to surround yourself with people that share your vision and your excitement, and your energy yes, a lot, yeah, absolutely, but that's actually that.

Steph:

That will only take you so far, and it's really, really important. I think that a team has, you know, lots of different personalities and lots of different strengths. I always employ people for aptitude, so you know they have to share the vision and have to, I think, fit well within the culture and you can tell usually quite quickly that that's the case. But what we had in in 2023, when we reached out to Amplified, was we had a team of people that hadn't actually been in a senior leadership team, that hadn't actually been in a room together in person, so we'd work literally. We're a new business with a new proposition I've been on boards like that.

Sam:

It's mad, isn't it?

Steph:

oh, yes, yes, um. So it was very, very almost surreal that these people who had, you know, really taken the business quite a long way initially, hadn't actually met really and we had noticed that there were communication problems. We were in kind of May June time, staring at the summer holidays, thinking actually, are we going to meet our targets for this very new business over that summer period? And my business partner, who was keen to retire, was saying maybe we should just call it a day, um, but we could tell that the proposition was receiving, you know, lots of really good feed. We were getting such great feedback and so we started talking to Amplified about let's do some disk profiling and let's help people understand, you know, how their differences can actually become a strength and, you know, make our team stronger.

Steph:

So it was very, very interesting and what we found and I was really, really happy that we had a really, if you imagine that the disk profiling identifies whereabouts you are on a kind of a disk. It will tell you about how you like to communicate and what you love to do. Now I think personally that the way to build a successful team is to work with people's strengths. So me personally, I can put together a spreadsheet as well as anybody, and I can put together a report as well as anybody. But if you put me on reports and spreadsheets all day, I won't want to come back to work.

Sam:

Sure, sure, I won't want to come back to work I will lose my engagement and my excitement.

Steph:

But and that excitement and enthusiasm I get from other people in our proposition and our clients. But there are lots of people on my team who do amazing jobs with spreadsheets and reports and love to do that. So DISC allows us to identify which people like to do what. So when we're looking at roles and responsibilities, we can really start to shape that to fit the people that we have and maybe move some of that stuff that perhaps isn't something they're passionate about to somebody else who is passionate. So what you then get is an incredibly well-rounded team who are excited and engaged. And then what we do is we check in. So I can tell now because I know where people sit on that desk assessment. I know if Phil, for instance, is doing too much of the stuff that he doesn't like to do. I know straight away.

Sam:

But you can repoint him in the right direction, so he feels engaged yeah, absolutely, and I get people to.

Steph:

If people start to say they're feeling overwhelmed, it could be because there's too much of the stuff that they don't love to do in their everyday role. So what we do is we we kind of try and work to making sure people have at least 95 percent of the things that they love in their everyday role and does it does it help you identify gaps in your sort of collective brain, as it were?

Sam:

You know if you're you know, you realize that in your business you're lacking somebody who is is focused on process and spreadsheets and stuff, or yes?

Steph:

yes, without a doubt. So I would feel uncomfortable if I knew that we had those gaps and I would look to fill that with the right person. And also, we have to be careful, as you know, as a senior leadership team or an exec team, that we haven't got too many people in the same spot, because otherwise, you know, that will outweigh the overall kind of performance that we're looking for. And it's really important for that team because we are so different, we're going to communicate differently. We're going to communicate differently, we're going to react differently when we're under stress.

Steph:

So it's really good for that team to be mindful and understand where everybody sits and what's going to happen if I'm stressed or um, you know, yes, perhaps you know, perhaps some of those negative behaviors you know and we can perhaps be a little bit more understanding our, our core, um, you know, the core of of our team is kindness and understanding how people operate um and how, how to get the very best out of each other. Um, I think is, is, is part of that kind culture.

Vic:

I think is is part of that kind culture. Um, steph, it's just made me think, as you're mentioning kindness, um, I don't think Sam knows. So we met Steph through Tracy, so Tracy works works with you.

Steph:

Still, yes, she does, yes, so Tracy provides third-party HR. Uh, support for us and does amazing.

Vic:

That's the connection. There's the connection yeah, yeah exactly, yeah. So tracy did a podcast with us way back um called you can't automate kindness, so she she is our kindness queen, which is kindness guru yeah, she is, yeah, yeah yeah, I think it's a lovely ethos to have in the team.

Steph:

Um, I think that we're all working to capacity, I think most of the time, especially in a startup. You know it's growing, moving. There seems to be no time for consolidation, um, and, and I think that it's good for us all, isn't it, to take some time and just make sure that we're really treating the people around us, whether they're clients, whether they're the markets. You know that we serve, or serve us and our clients and the people around us with kindness, and I think DISC helps us do that.

Vic:

Yes, yes.

Steph:

At that point, when we reached out to Amplified, we had this yawning kind of gap where we thought we're not going to get any income in and, you know, my business partner was saying let's just do a day. And we got the team together, we did the disprofiling. There was a real aha kind of moment and I think it really helped. And what we did as well is we were able to get together with support, and I thought that third-party support was amazing because it allowed me to sit back as a team leader and let other people talk and let somebody else lead. And it was very well planned going into that session and what we did was we identified the things that were urgent, you know, and who was best placed, you know, in that team to deal with those things and how we would go forward. And we smashed our targets and so we're still doing it.

Steph:

And we're just going into another growth stage where we are increasing our technology and our digital proposition. And so, to take our team successfully into that next stage, we're going to hold another couple of days where we're just going to remind ourselves of where we all are on that disc and look at how we improve our communication and how we meet those next goals together.

Sam:

And have you added people to the team that have joined since you did the initial profiling exercise. So I guess it's not a bad thing to sort of plot out where they exist on your desk.

Steph:

Yes, absolutely, absolutely, and really interestingly as well. Recently we did somebody's disk profiling because their role had changed such a lot.

Sam:

And.

Steph:

I wanted to understand whether, because that person's role had changed quite dramatically from being very much a client relationship manager to more of a digital project manager, I wondered whether that changed how she, where she was on the disc and it was exactly the same oh, interesting.

Sam:

Yeah, I was wondering if people I was thinking about this the other day you know where I was, say, 10 years ago, when I was, you know, in the throes of working full-time really hard, young family, all that kind of stuff to where I do feel like my, my personality has changed, softened a little. Yeah, and I wonder if I if I mean, you know obviously you can't do it, but theoretically if I went back and did a disc profile of myself 10 years ago versus today, I feel like I would have, I would have shifted on that axis a little, a little yes, yeah, no, it is really really fascinating, um, but uh, it really does help us focus as a team.

Steph:

It helps me identify people's strengths so that we can work to those.

Steph:

We very rarely lose a team member and I think that's about DISC. I think that is because we are ensuring or supporting people to do the things they love and if you're doing something that you love, you don't get that sinking kind of oh it's Monday morning feeling, so much perhaps, and you're more engaged. Um, and I think flexibility in in how you know we support people in in working and you know to around their families and and their lives helps as well. But definitely having that understanding of who we are, um, we have somebody who is in that kind of very supportive area of the DIS chart and what I found out was that that person, in putting a team environment with that senior leadership team, is perhaps not going to always offer an opinion.

Sam:

Because of that, all of the team now are very aware of that and so they will ask her for her opinion yeah, and to actively bring her into the debate or or solicit an opinion from her privately, separately, outside of the hub of a main meeting.

Steph:

Yeah, that makes sense yeah, yeah, and also as well, where we even sit in a meeting as well. So we try to put the quieter people or the more detail oriented people project managing people, we try to mix them in with the kind of more entrepreneurial louder.

Sam:

Yeah, yeah, that makes sense.

Steph:

The noise doesn't drown out.

Sam:

Or, you know, sit them next to whoever's sort of chairing the meeting.

Steph:

Yes.

Sam:

Because you know if they're to the right or the left, they can almost physically be brought into the conversation.

Steph:

Yes, absolutely so, yeah, so for me, as a manager, it makes managing a team much easier.

Sam:

And I say this time and time again, but a lot of programs like this are about making explicit the things that we know intuitively and we probably sort of do, but it it brings it top of mind yes, you know, I guess I guess we would all naturally try and bring the quieter person into the debate yeah but it might get missed in the cut and thrust of a meeting.

Steph:

Yes.

Sam:

But it just makes sure that we kind of have it top of mind, right.

Steph:

Yeah, no, absolutely, and also as well for the rest of the team. I think that if you ask that team, they would all say that it's been really helpful, you know for them to understand.

Vic:

Um, you know each other a little bit more yeah, because it's not just about them talking to you, is it?

Steph:

it's about they work with each other yeah, absolutely, and and actually I try and be as hands-off um as possible from that team. Yeah, I think it's really important that they are. They're amazing and I think it's it's. You know, we employed amazing people because we think they can do amazing things. So I I try not to micromanage um this particular business. You know, um, I'm older, it's probably going to be my last business. She says um, and and and. So it's great to be able to, you know, stand back and watch people, you know, take what was my vision forward in very unique ways and add their own spin on that. So, you know, I couldn't be prouder.

Sam:

Brilliant, that's great. So one thing I thought might be interesting to explore, because I don't think we've done this on the podcast, but as an Amplified Group client what was the process? How did you go about it? Did people have sort of pre-workshop questionnaires to fill in, or was it just a round table? How did that look?

Steph:

Yeah, so everybody did a disk assessment, and then we did.

Sam:

How long did that take individually?

Steph:

yeah, is it a 10 minute thing or is it a, you know, an hour or so, I think it's about 25 minutes, okay, yeah, um so it's not a massive overhead but what you get is this very, very scarily accurate kind of assessment of who you are and what your strengths are and how you work best. And it's incredible because it's not just about where you are or what quadrant of that circle you land on, it's kind of where you are, are you closer to the center, are you closer to the edge, which will all define how you work and how you love to work, which is the most important thing. Um, so I've done lots of um. You know the assessment, uh, kind of quizzes, whether you know would you prefer to paddle a rowboat down a stream or climb a tree that you know build a tent in a field. You know those really kind of random questionnaires. But I would say that the DISC profiling not only is more unchangeable as you go through your career, but I think it's more accurate. So what you get as a leader and we asked the team if they were happy for the for all of the team to share those results with us you know, as a leader, and we asked the team if they were happy for the for all of the team to share those results with us you know, as part of this exercise, um, and everybody was very happy, but they also had a really good insight to how they worked, um, as well as us being able to have a bigger overall picture, um, which I think was really really quite exciting.

Steph:

I think that part of the part of the exercise. And then we did some behavioral questions. So you know, asking how does the person who was asking the answer in the questions, how do they think the team are performing together? It was their trust. Did people feel that they were working very effectively as a team? So lots of questions like that, and it was anonymous as well, so people felt that they could give that feedback. So that again was very, very helpful to bring all of those responses together and we could then tell, like a traffic light system actually, which areas we needed to work on. I felt quite proud that at the point that we did this last, trust was very high for us and we were a very new team at that point. So it'll be interesting to see. Our sessions are next week, so it'll be interesting to see how we progressed or not.

Sam:

Hopefully it hasn't gone down now that you're a longer established team, I'm sure I'm sure it won't.

Steph:

But you know what, the thing about culture and the thing about teams and and definitely in a startup, where you have very different pressures, I think because you're growing so quickly is that you have to keep checking in. You can't just assume that because this was great a year ago or six months ago, I think this is something you almost need to take a temperature check with, you know, weekly, daily, depending on what products that you have.

Vic:

It's fragile isn't it?

Steph:

It's so fragile, and it's not just stuff that's going on at work that will throw that balance out, it's whatever is happening in the different individuals, home life as well. You know we're so, we have such blended lives. You know our work and our home lives. As much as we all try to get as much balance as possible, it is has started to blend, and so what you do have is, I think, more than ever, you know, those complications or everyday concerns you know are with you when you're working, perhaps more than than we saw previously. So, yeah, no, absolutely. I think this is something that is so fragile and you should never, we never, you know, take that for granted that the culture that we have today will just merrily, you know, clip-clop along into the future.

Sam:

Yeah, I mean, you know, in my Softcat days, that was the thing that we concentrated on more than anything else was how do we, how do we maintain that culture? Yes, yeah, every director's meeting. Martin, you know, don't get complacent. You know we've absolutely got to focus on how can we make it even better, what can we do to improve it? Yes and you know you're absolutely, especially with a business that's growing and growing quite rapidly, the moment you take your eye off the ball.

Steph:

Yes.

Sam:

It's the moment that stuff goes to Helen's hand or her basket, whatever the expression is.

Steph:

Yeah, absolutely, and I think as well, it's really important to me definitely to be able to say to the team do you know what? We didn't get the resourcing quite right for that project or this is what we've learned from this, we could do this better. So, um, that constantly looking at how you're performing and what you could do better and that's the question we're constantly asking our clients. You know, how can we support you more? What could we do differently, could we be better? Because if we don't have that feedback, we can't grow, and we're not just looking to provide a static solution here. We're looking to have a solution that evolves as companies are evolving and there's so much more. We have planned for this, and to have that feedback, you know, can be quite difficult sometimes, but it's the only way a team, a company, a proposition will grow.

Sam:

That makes sense. That's brilliant. It's really good, I think, to get the view on disk and the process from somebody who's actually been through it with your team. So, Vicky, have you got anything to add?

Vic:

Only I think we touched on it a little bit earlier. Every workshop that we do, we start with nothing we're going to cover is rocket science, yes, and it's all in your subconscious, but what the most important thing to do is bring it to the conscious and have it as a language that you can all use yeah, have to use it daily. And actually we're we're just we haven't talked about this at all, sam, but we're we're just about to embark on some really exciting developments at amplified group, where we're we're creating tools that lead us when they've worked with us and actually we're doing this a lot with um, working with our clients about the feedback that they've wanted, about what can we give you? That are those constant little check-ins just to remind you has this meeting run how we should have done? And so do you know what? I've got that foggy ahead. At the minute, I can't remember what we're calling them, um, but but they are literally, literally just five minute check ins to see how you're doing, just to help you keep on track.

Steph:

Yeah, I think. I think it's really, really important that you do take the time with with a team to check in, and I think we all do the usual one to ones. You know we spend time with our team because we're there every day with them. But I think there's something very powerful about taking a group of people out of an office and say, right, we're going to concentrate on us, right? So this is, you know, our end goal is to make us perform more effectively. But what are the things that are driving you mad every day? And I think we can all be so busy that we don't make, don't take the time to do that.

Steph:

Really, interestingly, you know we're a startup, so we started with very small amounts of funds and you know, every penny was allotted to either paying somebody or paying a bill, or you know, and it felt never ending, like we'd never get to a cash positive position.

Steph:

And at that point, at that June, we didn't have the money to do the amplified session. We didn't have the money to do the amplified session and, uh, I paid for this personally and said to duncan I, I know this is gonna work. I've used this before, I'm really passionate about this and I think we're gonna get the best out of our team. So I'm gonna pay for this personally and if this pays off, then I'll expense it. But I won't expense it until this has paid off. And, of course, we smashed our goals. I was able to expense it Happy days but it really is a really strong tool. And to be able to take that back seat as a business leader and to be able to prep, you know, to have the information in front of you and make the softer stuff a little bit more scientific yes, I think that's that's what it is.

Vic:

I think, yeah, yeah, it's absolutely it. It's how you turn this stuff that's in our psyche into a process. Yes, so that you can actually do something that's actionable and it's not fluffy and it is real. Yes, definitely.

Steph:

And the ability to be able to feed into the team anonymously, I think is really, really important and hard. As a team leader, you want everybody to say that it's going well and things couldn't be better, but that's not how you grow um yeah, positive feedback.

Sam:

Obviously it's nice to have and you know you want to.

Steph:

You want to reinforce the good stuff that you're doing, but sometimes it's the negative feedback that's more useful than the positive stuff yes, absolutely, and what happens is when a business is growing very quickly, the processes, the software, the people sometimes which is very hard that you start with are not necessarily the processes, the software, the people you go forward with, and that's not a negative thing. Maybe the people that you had initially would be best suited in a slightly different role within the team going forward. But it is that process of constantly assessing and looking at resources, looking at future projects, looking at future aspirations and the proposition and constantly adjusting where that should be and to get a senior leadership team together I think is really helpful. Everyone feels part of a bigger process, whether that's communicating what's decided to their teams or whether it's just helping shape the processes and decide which software and which people do what going forward. I think it's so important you know and people get empowered and having that common parlance uh, common.

Sam:

You know we did a softcat, we did a management retreat. This is a million years ago, relatively early days of softcat. You know there were some things that came out of that that just stuck and we would use that terminology, you know, forever and ever. You know, even eventually with people who weren't even in that original management retreat.

Steph:

Yes, yeah, absolutely.

Sam:

It's all a sort of a bonding thing, isn't it?

Steph:

Yes, yeah, absolutely. It's all a sort of a bonding thing, isn't it? Yes, yeah, absolutely, yeah, yeah, so I think we're all very excited about you know how the business has grown so quickly, and you know what we still have to do and how we're going to achieve that. Yeah, so next week will be exciting.

Sam:

Fantastic, yeah, cool, very exciting, very exciting. Yeah, next week will be exciting, fantastic, yeah, cool, very exciting, very exciting. Um, so we're coming to the end of our our time with you. I'm afraid, steph, sorry, sorry to uh get to that point. It's been an absolute pleasure do you have any takeaways for our listeners, anything that that they should have top of mind?

Steph:

um, yes, I think that there's a very old-fashioned view in every sector that work is work and actually you perhaps shouldn't really enjoy it. And we go to work, we get paid and it's it's, you know it's. So it's there for a purpose, right? But um, I don't think it has to be like that and I think that I agree, you know you can have lots of people who are very, very excited.

Steph:

Uh, you know about what they're doing and I think if you have that, you retain the people around you, the people that you thought were going to be amazing in your business, you know, and you can see that they are then amazing in your business. Um, yeah, I think you know we should all be able to do more of what we love um yeah, I think that makes sense.

Sam:

I think that's a that's a fab takeaway. If more people enjoyed their work, it wouldn't feel so much like work, right that's exactly right yeah, that makes sense. And are you a reader? Have you got any books? Oh, oh, yes.

Steph:

Oh, my goodness, I'm a terrible. I'm addicted to self-help books. One of the books that I reread regularly is Start With why? Because I think one of the things that I do in my spare time not that I've got a lot is I help to mentor other people with startups, and I think it's really important to ask why you're doing this. And I don't think money making, money doing something cheap, I don't think any of those things work. I think if you're trying to solve a problem or you're building something that's going to make something better, you improve something. I think that's always going to work.

Sam:

And the money will just follow yeah.

Steph:

I'd agree with that. Whether you're starting a business or whether you're providing a proposition for a client, I think that you know. Start with what are we trying to solve here, what is the problem, and then it'll become so much easier. So yeah, start with why. It's a book by Simon Sinek I'm readily available on Amazon. You can download it.

Sam:

It's a really good, thought-provoking book yeah, vicky, I'm sure you've read that one certainly have and watched the video many times about.

Vic:

We share that video, yeah, of simon talking about it. Um, yeah, many, many times in fact. I was asked by a prospect who has become a client this week to give him an elevator pitch and I sent him something late on Monday night and then read it and went oh, mr Sinner could be very pleased with me there. I absolutely started with the why bit yes, absolutely yeah yeah, thank you, thank you.

Vic:

Yeah, and the word I was looking for earlier was reflections. We're creating these five minute reflections for teams to use on a weekly basis, just to help check in.

Sam:

Yeah, yeah, that's good, I like that yeah yeah absolutely brilliant. Well, fabulous, steph. Thank you so much for uh, for joining us. That was a yeah, that's good. I like that. Yeah, absolutely Brilliant. Well, fabulous, steph. Thank you so much for joining us. That was an absolute pleasure, I can see the sunshine in the windows behind you. So let's all take 10 minutes of reflection and get outside in the blooming sunshine and enjoy it.

Sam:

I'm going to take Zelda out for a little stomp down the lane now and get her some For our listeners. Zelda is a dog not a person. She will be delighted with that. So just a reminder to me to say thanks again to Steph for joining us today and thanks for listening to Get Amplified from the Amplified Group. Your comments and your subscriptions are always most gratefully received.