E56: Building High-Performance Teams Through Direction, Alignment, Commitment | Shirley Riddick, General Manager, APAC, Insightsoftware

3 things that I learned about when I did my executive leadership course. It was the 3 most important things in growing a successful team are DAC. We often talk about the DAC. So it's direction, alignment, and commitment. And if you can just get those 3, if you have a team which knows where they're going, they're all aligned, and they're all committed, success will follow.

My guest today is Shirley Riddick, General Manager of APAC at Insight Software. For 20 years now, Shirley has been building and scaling high-performance teams across continents and operating at every stage of the growth curve. If you want to understand what disciplined, steady leadership really looks like when the pressure is real, this conversation is for you. Welcome, Shirley.

Thank you, Tia. It's lovely to be here with you today.

Shirley, something deeply personal that I do know about you is that you've been a 2-time breast cancer survivor. You know, Tell me a little bit about that and how that shaped your perspective on your career and personal life going forward.

Yeah, so Tia, the first time I was diagnosed, my daughter was 6 months old, and it was back in 2012. It was a big wake-up call for me. And then the next time I was diagnosed was in 2004. So it was pretty much 12 years later from my original diagnosis, but I had been cancer-free for 10 years. So the second time came as a real shock. I think the key learnings through both of those, you know, staring death in the face, and I've had some— neither of them were easy journeys. It was chemo, it was surgery both times, radiation, the works. It's taught me a lot of resilience. It's taught me not to sweat the small stuff and to really have an appreciation for every day that you have in this world. It's a gift. Every day is a gift. And if you can just wake up and embrace it and be grateful for what you have got, that's really how I embrace every day that, that comes my way. I'm just, I'm so grateful to be here. Oh my goodness. Yeah.

What a horrible experience. No, what a horrific experience to go through, not once, but twice. And, uh, and I hope all is well now, um, and that you're living your life to the full.

I am 100% healthy and happy and living life to the full for sure.

Wonderful. Thank you. Now you've seen almost every phase of a company's growth. You know, you were the first employee at Excel for Apps in South Africa, and you saw that through to an exit. And then you went through an acquisition integration with Insight Software here in Australia. Then COVID hit. And so you've seen it all. Tell me a little bit about your journey and how did you evolve as a leader through those stages?

Yeah, so it was a very exciting journey. I absolutely loved the scaling part. I think I'm very much a builder when it comes to business. I like to build teams. I like to build culture. I like to win and obviously build, you know, a profitable business and deliver revenue for shareholders. So I certainly loved that stage of my career, the first 12 years at Excel4Apps and all of the the building that we got, got to take place. I was fortunate to be part of the sort of being the first employee, I was part of the leadership team and was able to influence, you know, how we decided to grow in other regions, be it rolling out into the UK. I was able to support that rollout. Also the North American, you know, to help with onboarding and training and attending events globally to make sure that we were consistent across the, across the organization. So yeah, very exciting time.

Wow. Was there ever a quiet moment during one of those periods of growth and change where you genuinely questioned whether you were the right leader for that stage of growth?

Oh, yes, definitely. I think probably one of the most challenging times in my career was when I moved from South Africa to Sydney. So, XSOFT Apps had just exited Insight Software, or just been acquired by Insight Software. I was in a new country, I was in a new role, there was a new leadership team. I didn't even know which washing powder to buy in the shopping center, in the grocery store, let alone, you know, to feel 100% secure in what I was doing. You know, the old safety net of the leadership team that I knew was no longer with the business. So, it was certainly personal transition as well as professional transition. And then shortly after arriving in Australia, COVID hit. So it was complete global disruption all at once. And I certainly had a moment then where, yeah, exactly. And I just thought, wow, you know, am I the right, am I the right leader for this phase? And can I do this and can I get through it? Yeah.

I'm really curious because it seems like you, from first account exec and, you know, in the startup and then you grew to leading multiple continents really quickly and then you continued to do things that you hadn't done before. There must've been a lot of trust there. Right from the early onset there that, you know, you had this capability to grow with the business. And then again, at Insight.

Yes. Yes. Look, I'm very grateful for the trust that was placed in me. I often, um, tell the story that I was hired 3 times by my same boss. So straight out of university, he hired me at KPMG and that was sort of my very first, um, career, uh, or job that I took. And I then left and I went to go and work in the UK. I came back and I was rehired at KPMG again. And then he left and started Excel4Apps. And when I was ready to leave KPMG for the second time, when I was tired of consulting, I called him to be a reference and he said, no, come and have a chat to me. And that's what, what urged me to join Excel4Apps. So, I was hired 3 times. A lot of trust was placed in me and very grateful for that trust.

Yeah.

I think the reason it's there is because I delivered. I backed myself. It wasn't easy. It was hard. I was stretched, but we all know that the greatest growth comes out of being stretched. So I backed myself, had a great support team. I didn't do it on my own. It was certainly the team of people that were around me that helped get us there.

That's incredible. It's an inspiring career path and promotion that you've had. I really don't see that very often. But so, At Insight Software, you know, you were acquired by Insight Software during that first 90 days post-acquisition. Uncertainty is always high. Everyone's watching you really closely. So how did you navigate that so that the team stayed focused and steady? Oh yeah.

So those first 90 days were very fragile. Um, as it is with acquisitions, you know, often people are, um, transitioned on day one. So. You see some of the company leave, some of your teammates and employees leave, and it's unsettling for a lot of people. So initially there was some shock, there was hurt, and there's grief. And your job as a leader is to, you know, navigate through that change curve to make it not, not as deep for individuals and not as long for individuals.

Mm-hmm.

And to do that as a leader, you've first up got to establish trust and acknowledge what people are going through. Don't rush them through that loss, but Make it shallower, make it shorter, be consistent, show up every day, offer clear direction and strong alignment because with all of that, you're gonna get commitment from individuals. And hopefully most people, most people did come on the journey with us, those that stayed on in the business. Some people chose to leave. There's always, it's always better for the individual, um, post an acquisition. I feel like people always land in the best spot that they need to, either for them personally, it's something better or there's something better for them within the business.

Yeah.

Um, so I obviously moved on with Insight Software and stayed for, you know, it's now 8 years and counting.

Yeah, that's amazing. And I've often noticed that the teams that stay through the change, it's always, most always because of the, how the leader handled those first 90 days as well. And, you know, um, you know, the faith that they put in that leader. So credit to you.

Thank you.

Now, every leader faces this, um, you know, When you can see a quarter that's going off track, tell me, where do you focus first? Is it people, pipeline, or process? And why is that?

Well, Tia, the first thing I do is remind myself that it's, we're a team and we're in it together. So, it's probably the people where I will look to first. Obviously, I'll be feeling that pressure as much as everybody else in my team is feeling the pressure. So, I certainly don't try to insulate myself from it or pretend it's not there. We've gotta acknowledge that what the team is going through matters, and the pressure doesn't disappear when you ignore it. It only amplifies.

Yeah.

And from there, you know, I think I'm quite considered, and I like to pause before I respond to things. I like to make sure I'm not reacting emotionally or creating noise. My job as a leader is To provide clarity and not to add to the urgency. So, I would look at all 3 things, people, process, and pipeline collectively. People can tell you the story, what they're seeing, what they're hearing, why they're struggling with pipeline perhaps. But I certainly am a strong believer in the power of the team is greater than just a single individual. So, I address it collectively. It's never one of those things.

Yeah. Yeah.

On its own.

Yeah. No, that's good. You also shared with me that you have invested really heavily in your own growth and personal and professional development through earlier on in your career, executive coaching, you've explored psychometric profiling, and you've even read sales books with your, with your team. How has that investment fundamentally changed the way that you lead?

I think there's 2 things which are the, you know, have been the greatest learnings out of, um, out of, you know, my self-investment would be first up self-awareness, unlocking self-awareness, and probably the frameworks that I've learned. I believe that through learning the frameworks that I've, yeah, been able to kind of wrap my head around, that's where scale comes.

Mm-hmm.

So, I'm a big fan of Patrick Lencioni. His work's helped me understand team health, trust, productive conflict in a very practical way. Also being vulnerable in front of your team. I think one of his books is called Getting Naked.

Okay.

Really good read. The ideal—

Sounds good.

I think it's given me the frameworks with which I can lead and those repeatable processes that when you feel like you're in a situation which is uncomfortable, or you're being stretched, you can lean back on one of those frameworks that, you know, can get you through. Simon Sinek has definitely shaped how I think about purpose, belief, and leading from the inside out and being a selfless leader, which is something I do try and pride myself on.

I love that.

Yeah, there's others like Jim Collins, Liz Wiseman. I love her book Multipliers, is a, is a must-read if anybody wants something good to read, because we are all accidental diminishers, which You know, we do things like, I, for example, could be a pace setter whereby I work, I have a very high work rate. I operate at a high speed and that can create a lot of burnout if I'm not aware of it. And it's, it could make me an accidental diminisher of burning people out around me because I set the pace too high. Whereas you want to be a multiplier.

Yeah.

You want to be a multiplier who gets the best out of everybody. So you set a pace, but not a pace that's uncomfortable for others.

Yes. Interesting. So by default. You're a pacesetter.

I am a pacesetter. It is one of my, it's one of my traits.

One of your traits. With that, I wasn't going to ask you this, but I'm interested. So because you're aware of that, how do you avoid burnout? What do you put in place, you know, on a daily, weekly basis to make sure that, you know, you're maintaining the pace and not burning yourself out?

So simple things. First up is schedule email sends. So whilst I might work at 4 o'clock in the morning, or I might work at 10 o'clock at night, don't schedule it to arrive at anybody's inbox before their working hours, unless it's urgent and you need something.

Uh-huh.

And then just, um, very clear timelines on things. You know, if you're sending a request for information or data or a task out, have a very clear timeline onto when, when do you expect it back? by such and such a date, and then hold yourself accountable to those timelines and set them realistically. It's the, it's a fair thing to do to anyone.

There's some really good tips there. I actually, I agree with the email send. No one needs to know what time you choose to work if it's outside of hours, because that may simply suit you because you've taken out time to do other things. And that's the time that you're most productive or you get some quiet time as a leader.

Yeah, exactly. And choose your right communication method. You know, if it's something that's an IM, be it Teams or Slack or whatever you're using, just then that's a quick question. Ask that, send a one-liner to someone. Yeah. So I do actually believe that email is going to be a thing of the past one day very soon. We're not even going to be sending emails, but you can just have Teams messages.

Yeah. Yeah, absolutely. You've also mentioned that, um, you've been very intentional about team composition and using psychometric profiling.

Yes.

I want to talk about that because how have those insights influenced the way that you've built and balanced and even how you communicate with your team?

Oh yeah. So I really love the sort of psychometric testing that I've been able, been exposed to. And there's many different types. One of them is HPDI. The other is Discovery Insights. We talk about people in colors or you get certain profiles and certain shapes. They all actually, at the end of the day, say and mean the same stuff. So my, the easiest one that I work off is the colors. And if somebody is a different color to you, for example, having an awareness of what that color is and how those people might think or act differently, or just process information differently, makes for much more meaningful conversations. Because if I'm a, I am a red individual, which is—

Yes.

My tagline is, be brief, be bright, be gone. Whereas a blue individual— I know it's terrible— a blue individual is, give me the details.

Yes.

So I know when I'm talking to somebody who is very blue, I will actually arrive with additional information over what I would give to somebody who has a high red in their profile. Similarly, green is something I actually lack a lot. So I have individuals on my team that I will lean on to bolster my green. If I have an email communication or team meeting that I want to do and I want to run some comms by my team members who have higher green than I do, I will use them so that I can ensure that my communications and the way that I'm dealing with people is adequately touching each color in the room.

I love that. What is green process?

Green is show me you care. So if more of the feelings— yes.

Okay. Yeah, understood. So Are there, have you seen patterns over the years that you've been doing this that, that, you know, patterns that are coming up consistently in, in different areas of the business? Like, say for example, the profiles of a sales leader or an account executive versus someone that's working in a more technical capacity?

Yes. So, there definitely are patterns and executive leadership teams tend to have a lot of red on them, but having diversity And additional color is always a good thing, as with anything, you know, where you're forming a team, having different perspectives really helps and strengthens a team. So what we do is we map the team on a wheel and we'll look at everyone collectively. And you do tend to get sometimes people more like your solution engineers who are more detailed, tend to be more blue and green, and then your salespeople tend to be more red. It does not for one second ever mean that if you are a yellow profile, you're not going to be a successful salesperson. No, because yeah, I don't want anybody out there thinking that or thinking I won't, wouldn't get a job if I'm not a yellow profile and I want to be in sales. It's not like that at all. It's really just awareness. And once you've got awareness, you can dial your colors up as you need to.

Yeah, that's, um, so yeah, you've got your default, but it's also, as you know, if you're hiring, it's just insight how that person may think and act, but it doesn't mean that they can't push themselves out. Into the other colors. I love it.

Yes, exactly.

So good. Now, fun fact, I know that you worked with Richard Branson earlier on in your career.

Yes.

How was that?

Oh goodness. So I worked for Richard Branson as part of the Virgin Mobile launch team in South Africa. I'd actually just returned, um, from the UK when my boss rehired me to KPMG for the second time. So, I was conscious of how junior I was. I think I must have been about 26 years old at the time. What really stood out for me with Richard was his presence. He was consistently positive, friendly, and genuinely interested in the people around him. Like, he paid attention, and I mean real attention, because he had this remarkable ability to make everybody in the room feel important.

Mm-hmm.

I was a 26-year-old KPMG consultant sitting at a boardroom table, and he made me feel like I belonged there and like my contribution mattered. So that's something that I've carried forward with me, and every single person that's on my team, I want them to know that they belong and that they matter, that their input counts, that everything they're doing, I care about and I want to know about. So working for Richard was great fun. We had a wonderful launch party in South Africa as well.

Oh, I bet.

And he's fun to party with too.

Oh, yeah, I'm sure. So tell me, what is one, I think you shared with me a lesson as well that he said to you about don't be afraid to hire someone. Yeah.

What was that? He said to me, Shirley, always surround yourself with people smarter than you. So don't be scared to be, you know, to not be the smartest person at the table. And he attributed a lot of his success to that. And I certainly, that's lived with me. That's carried with me. I love having people that are better at doing their jobs than I am. Like, I do not believe that I could do the job of anyone on my team better than they can do it. They are the best people for their jobs.

Yeah. Yeah. Yeah. You've got to hire for the gaps in your knowledge and ability, haven't you?

Yeah, exactly.

That's good. So if you could sit down with your 20-year-old self earlier in her career, what career advice would you give her?

I think the first thing would be not to take myself too seriously.

Yeah.

You're allowed to make mistakes. It's okay. And if you're going to fail, fail fast, because when you fail, you grow. And it's success is in rising, is not in rising, it's in rising every time you fall. So I would kind of tell myself, don't be scared to make mistakes and don't take yourself too seriously. The second thing I would tell myself would put your hand up for everything. Like if there's ever a new project going or an opportunity to lead a team or to do a POC for something or prove out a theory in a business, put your hand up for it and do it. I have done a lot of that and I think that certainly, you know, is where a lot of my growth has come from. And then the third and last thing would be like to be very deliberate about your reputation. Because your name travels into rooms before you do show up and how you treat people, every single person in the business, right from the reception, the person at the reception desk to somebody who's serving your table. If you go out for lunch, whatever it is, how you treat people is really important. So I would, yeah, consider that.

Yeah, I love that. Actually, um, I was thinking about that too, and I was thinking, what would I say? And I'd say, you know, you don't have to have it all mapped out.

Yeah.

You know, where you start is not where you're going to end your career and you probably have multiple changes, but similar to what you were saying as well, you know, saying yes to taking on more responsibility even before you're ready for it and saying yes to challenging roles and, you know, be curious and to learn about the business and how they make money, how they drive revenue and what brings their customers back. But one of the most very important factors is to choose your manager wisely.

Yes.

Because, you know, if you choose a great manager, they're going to accelerate your career by 5 years and choose a bad one and they're going to set you back. And so anyone who has had the opportunity to work with you, Shirley, has been very fortunate in their career. And I'm sure you've been a great career accelerator.

Oh, thank you, Tia. I hope so. I think I have. So yeah, I certainly hope so.

Yeah. Now look, what's really stood out to me has been your consistency and your composure. I know you said to me before, you know, what you see is what you get with me. And you could really see that, you know, the standards that you hold yourself to and the clarity you bring, especially when there's uncertain times.

Yes.

And that's really not easy to do. It takes a very special type of leader. So, um, thank you. Thank you for being so open in sharing your journey. And there's a lot of value to be gained from the conversation, whether it's someone that's leading a team or someone that's looking to build their sales career.

Thank you, Tia. Yeah, I've really enjoyed chatting with you.