I find it difficult to get that kind of “mastermind” group where I am right now.  So, I actually wanted to be part of this group so that I can learn from others, listen to others.

Everyone in the group can be very, very objective, as there’s no emotional connection or attachment to your company. So, we can say something, and it’s up to the other person to actually accept it, or not take it. But the point is, everybody respected the views within the group I might have said something controversial, but they were like, okay, I get where you’re coming from.

So that objectivity was something I found very impactful, at least for me, and while there were certain challenges within the group, everybody in that group was also very, very positive and supportive in helping you to constructively deal with them. Many times, you’ll be like thinking, oh, my, I have the weight of the world, you know on my shoulders, but it’s every single person in that group has that same weight. They’re taking on the same weight. And it’s interesting how they would approach it.

In terms of tangible changes in my company.

In the first few classes, we had a vision, mission refresh which is all standard. Doing those exercises allowed me in two months to change my website to a completely new website, more aligned to our direction and with really on point messaging.

I also realised that one of the business units we had will not be profitable anymore. And it was also it was a decision that I took to just cut that unit, and reallocate the resources. The group and the teaching content encouraged quick decision making rather than procrastinating. And the team was actually quite shocked I did that.  When I did that decision, some people were shocked, but I think some of the others were like, wow, that’s the way to take a decision. Don’t wait.

I personally was having profitability issues. I decided that I don’t want to be at a single digit % kind of profitability, I want a good double digit profitability, which is in excess of 30%. I started making business decisions (like cutting units, focusing on higher margin clients, focusing on high margin work) that aligned with this goal.

There was a session about how to communicate with others. And there was this technique of, hey, here’s what I observed, feeling, expectation. Those three steps in that framework, which now we have implemented into our appraisal system as well, had an immediate and profound impact on the team. I did that I had a little bit of an issue with some people which got addressed. And the team also understood where I was coming from better. And and the good thing for me was that they not only they accepted that feedback, but I saw some clear changes in behavior in the team.

I would definitely recommend the mastermind – in fact, I will be joining the next cohort too! If you’re giving repeat business, which I am, then you know that someone’s great.

I would recommend it to anyone who’s in top management, and upwards. In the C-Suite. Definitely, people who want to listen to others. It can be a big company, it can be a medium sized company, or even a small sized company. I think the lessons can be learned from everywhere. So if you’re a large company, you might be missing out on certain nimbleness.

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As an executive, it can be quite lonely at the top, and so having the opportunity to surround myself with a few other folks, especially of different walks of life as well, in different industries was appealing because I believe in the value  of diverse thought and experience and some of the opportunities for learning that that can present. So really, that was the main driver, kind of continuous ability to learn from Sara and learn from others and sharpen the pencil as an executive.

I’m just sad I didn’t get to benefit from it as much as I could have due to a health issue!

There’s a lot of shared experiences with respect to the challenges of being a leader, whether that’s from financing to dealing with other founders or other members of the leadership group that may be challenging to deal with, and the various headwinds that exist that are out there and seemingly never go away. I think there’s a lot of interesting thought and just like a good feedback loop from the group that the Mastermind created, which is cool. 

One of the big things that I realised is that just pulling people together because they’re talented isn’t the right move. There has to be emotional connectivity there that I think is hard to appreciate, but something you shouldn’t discount. Culture is everything.

After bringing SIS to its current point and successive years of 40% YoY revenue growth, and realising that there was a divergence of vision with the Board; I decided it was the right time to move on to my next adventure.

I realised that I like two aspects of business that I really find myself drawn to. Coming from a sports background, that is the team set up, which I think Draftkings, that I’m returning to, has in spades. They have a high performance culture and I was really drawn to that. That competitive dynamic that exists in the ecosystem where there’s always that group that you’re against. So that helps create that camaraderie and that sort of team dynamic because there’s a shared enemy. I believe in the competitive spirit of people in a business. And I think that’s a really big draw for me.

It’s amazing how my perspective has changed by virtue of leaving Draftkings, rolling the dice, taking on a CEO’ship at SIS. I think I have more shared experiences with the founder team now than I would have, had I not actually departed Draftkings. And so I think it set myself up sort of better going in and I have all this learning in my back pocket.

I would recommend the mastermind!  If you’re new to the role or if you’re experienced in the role. Either way, I think it’s super valuable. If you are in a leadership position and you don’t have a great support network of other people around you who are in similar dynamics. Like for myself, with a company solely remote, I don’t go into an office. So, I don’t get a lot of exposure to other founders, especially outside of my industry. 

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I wanted to surround myself as much as possible with people that I thought might be sharing similar experiences to me, or had experience that I could draw upon, because they are or have been in similar situations to me, in terms of growing a business, working with co-founders, and all of the trials and tribulations associated with that. So the idea behind it, behind me joining it was to surround myself, with like-minded people that I could learn from and share experiences with.

Just knowing that there are others that have faced the same challenges was quite reassuring to me. And I felt less alone, as a result.

I had spent a long time wishing that people and the world around me were a certain way. And as a result, was quite frustrated in various situations I found myself in. But actually, the change that I want to see in the world around me and in the people around me starts with me. And the responsibility to make that change falls on my shoulders, and I should change my, the way I communicate and my actions, rather than wishing the world was different. So that was one of the major things for me. And it did positively change the people and situations that I found frustrating. They changed naturally, in response to me.

And also the importance of coaching as part of communication. So how effective coaching can be and asking the right questions at the right time, versus trying to sort of tell people I want certain things in a certain way, actually helping them through questioning and coaching to come to the right conclusion themselves. Whereas previously, I was, I didn’t realise actually how effective coaching and questioning were in reaching common ground with people. 

I’ve also noticed my conversations with customers now are much more effective, and they lead to much better outcomes in general.

So what I mean by that to be specific is the way I communicate with customers now, we tend to find common ground a lot quicker than we did. And I get the impression that customers also feel like I understand them better. And I understand their issues better. Because now, the coaching and questioning is also as important with customers as it is internally in our organization. And by employing that kind of coaching mindset, and also better questioning with customers, we get to the heart of their issues and challenges faster. And I find that they open up quicker as well.

Prior to this, our sales calls would follow a broad framework of questions, but they never really got to the heart of the issue, which was, in our world, the visceral pain that our prospects feel. We never really got to that level. Now we do.

And this change I see internally within my team as well. We communicate much better.

I think having a peer network of other founders around you is absolutely key. As I mentioned earlier, it makes you feel less alone, but also it’s reassurance that the issues you are experiencing aren’t only reserved for you as an individual, but actually others as well. So I think founders, entrepreneurs, leaders, actually anybody in a team who wants an outside perspective on what they’re doing from someone who has either been in that situation or is going through that situation now, I think would really benefit from being part of this mastermind group.

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