Leadership and Psychological Safety with Ben Cutler

Get ready for an enlightening episode as we welcome Ben Cutler, the visionary leader behind Hushmail, to discuss the transformative power of leadership rooted in humility and transparency. Ben shares his unique approach, inspired by General Stanley McChrystal, where success takes precedence over always being right. Our conversation uncovers how radical transparency, and psychological safety can empower frontline decision-making and foster a thriving team culture. Ben’s refreshing vulnerability demonstrates how personal growth, triggered by learning from mistakes, can drive organizational success.

Here are some key takeaways from this episode on Courage Unmasked:

About the Guest

With over 20 years in senior management positions, Ben Cutler has been CEO of Hushmail since 2001 and has been with the company, in various capacities, since prior to the 1999 launch of our encrypted email service. Before joining Hushmail, Ben worked in the financial services industry. Born in the UK, he has lived in Anguilla in the Caribbean and Ireland and is now settled in Vancouver with his wife and family. Despite an educational background in finance and accounting, it was Ben’s passion for technology, privacy, and business development that inspired him to embrace the opportunity he saw with Hushmail. Ben is a generous and social person who is ultimately driven by a desire to build strong relationships with our customers and Hushmail team members.

‍‍Transcript

Carol Park: 0:03

Well, hi everyone, and welcome back to the Courage Unmasked podcast, where our guest today is Ben Cutler, and I'm so happy that y'all are going to get to meet Ben. I've known Ben for gosh since a lot of years I'm thinking maybe nine, 10 years, maybe 2013, 14, maybe 15. We met in the kind of entrepreneurial circuit of starting companies he with his and me with my cohort starting ours and have just had such a great time getting to know Ben. So I'm glad y'all are going to get to hear from him and know him. So, welcome, ben, and tell us a little bit just about your company, your entrepreneurial journey, kind of how you came to be the leader of your company.

‍Ben Cutler: 0:56

Hi, carol, and thanks for having me on Sure. So Hushmail. We provide secure, HIPAA compliant communication tools to small healthcare practitioners. A typical customer is a sole practitioner therapist, but we serve customers all across healthcare. The service is primarily a secure email service. We also have secure web forms that support electronic signatures, so our clients use the service to communicate with their clients and patients in a HIPAA compliant way. They also use the secure forms for things like intake and patients in a HIPAA compliant way. They also use the secure forms for things like intake forms, health history forms and for their practice, and the idea is for the communication platform to be easy to use and just generally help with the day-to-day running of small practices. I've been in the role for quite some time. I started off in a finance role. I started off sort of academically as becoming an accountant, but I think I found my calling in sort of the more of a CEO role.

Carol Park: 1:53

Yeah, and I obviously I will vouch for Hushmail because I use Hushmail and it has been fantastic in my own private practice. And again, we just kind of got to know each other along the way, going to conferences, having booths next to each other, across from each other, spending time with our other cohorts in the space to going to dinner. So, as I've known you through the years, I definitely observe you as a vulnerable and also very humble leader, like I just observe you even working with the people who work with you, alongside of you. So how do you think you came to be this way as a leader?

Ben Cutler: 2:41

That's a great question. I think part of it's just baked into who I am. Leader that's a great question. I think part of it's just baked into who I am. Another aspect of that will be from experience. I've been in leadership for most of my career, but obviously I didn't start there, so I do have both sides of the equation there. One thing I think that it's quite important is I try to focus on how to achieve a success as opposed to being right. Is I try to focus on how to achieve a success as opposed to being right, and so I think that's a different way of looking at things, and I think in that scenario, you have to be open to not always being right, and that's absolutely appropriate.

Ben Cutler: 3:13

In my role, I don't have all the answers. I want to get to the right answer. I think also my style has just evolved through the years. It's really a work in progress. I work with some really talented, insightful individuals. I learn from them, which is also really great.

Ben Cutler: 3:37

And then a few years back I came across an article by General Stanley McChrystal and it really resonated with me and he was over in the Middle East and he had some pretty significant responsibilities and I know military is an interesting comparison sort of kind of subject to this. But he changed how they did our operations quite significantly. And he had kind of three principles to really kind of resonate with me Radical transparency, so everybody knows what the mission is. I think that's applicable in all businesses. If you've got people who have siloed information, you're not going to get the same outcome as if everybody understands what the mission is. The other thing that he does, he believes in, is that the person closest to a decision should make the decision. And you know, in a typical organization you know that's kind of top down the CEO would make all the most of the decisions. But I think it makes a lot of sense. So you know, if you've got somebody on the front line, they can make a decision and it's more efficient for them to make a decision, it's more empowering for them to make that decision. They should know when that decision needs to be deferred. But I think that's a really powerful part of kind of the equation because it really makes people feel like they get to contribute as opposed to doing their job written from a script.

Ben Cutler: 4:59

And then the other kind of final point that he said he made, and this is really interesting because I think the uh the way he described it is daily. They would have a stand-up, a zoom meeting, like we're doing, but with a lot of people on it, and people would have to call into this, go into this, call and explain why something they had done hadn't worked out and he goes. You can't learn unless you make it comfortable to talk about the things that go wrong. Uh, and I, to me that's just sort of those three points that are really kind of lined up. A lot of what I sort of had sort of kind of come to in various different ways but in a very nice and succinct way. So that's sort of, I would say, a milestone on the evolution, but it's still.

Carol Park: 5:41

It's still sort of a work in progress sure, sure, we're all a work in progress, and I just think everything that you just described is how I perceive you as a leader, even though I've never worked under you or for you, with you, I've just observed you, and so what you described there, too, is all about psychological safety. You know that people need to know it's okay to fail and that sometimes in the failing, we actually grow, become more successful. So that psychological safety, that those elements that you touched on, I yeah, I couldn't agree more. It kind of has to start from the top down, but then the people at the bottom have to know, yeah, this is a safe place.

Ben Cutler: 7:03

I can say, oh, I messed up or how can I do better? How do you, how do you make that happen? You can't say it. You can't say it's a safe place once and expect people to accept that. You have to kind of create the conditions where people understand that it is a safe place.

Ben Cutler: 7:15

And I would say, one place where I uh do that a lot is where I have people that manage this report directly to me and we'll always talk about, um, kind of defining, kind of their authority, and I'm always encouraging them to, you know, to really push up against the boundaries of their authority in terms of their autonomy and agency, because I want them to really feel that they have that agency, that they have my support and they have my trust.

Ben Cutler: 7:41

And I always said well, if you overstep your boundaries a little bit, that's okay too, because we can learn from that, we can understand.

Ben Cutler: 7:46

Well, actually that was a decision that I probably should have made, and then we can. We've got some data there, we've got some understanding, because that kind of puts some definition around that. But I always encourage people to sort of to really really sort of lean in to kind of their role and the authority that they have, and I try when I communicate with with them, not to tell them, but to sort of have a discussion about the issues and then sort of encourage them to sort of formulate their response. Because I think if I make the decision for them or tell them what they need to do, I'm robbing them of the real value of decision making, which is the critical thinking around how do I solve this problem If I wasn't there? If I wasn't there, they would have to do this themselves, and in another set of circumstances they would probably do this by default. And so I think the organization, the way I look at it, we should be sort of creating the conditions where people can exercise that authority.

Carol Park: 8:50

But the same token we want.

Carol Park: 8:51

We want them to as well, and've talked at numerous times on the podcast with different guests about psychological safety and have touched on Google's Aristotle project, where they went in to see what creates success.

Carol Park: 9:09

They had predictions, hypotheses. We think if you hire the smartest people and put them in a room, you're going to be successful. And this was like a two-year study and really what they found at the end of the two-year study is the number one element of success that drove success was psychological safety and, as you said that, I was like, yeah, because what you said is when people feel safe to be able to make a decision, they can think more critically, they can think outside of the box, because they're not afraid that they might be shamed for their response or criticized if it doesn't work or whatever, and so it gives them the freedom to be more creative, to think outside of the box, to use what they can bring to the table, and I hear in your leadership how you really build that into people and into your employees so that they can think outside the box. So, yeah, you just put that so well.

Ben Cutler: 10:11

I think so yeah, you just put that so well, I think. Yeah, I think it's such an important part. You know, if I look back on my career, I've made, you know, many, many mistakes. Every one of them is a learning opportunity, and so it's okay to make a mistake because it's a learning. These are opportunities as opposed to mistake, and very often the mistakes are not material in the scheme of things. So they're not, you know, they're not going to end the business, they're not going to have dire consequences, but what you can do is you can take some time to kind of go what can we learn from this? What can we do better? Is there a process that needs to change? Or is there an area where, okay, we know that somebody needs to kind of focus on sort of honing their skills in? And I think, for me, when I look at, when I have these conversations, I look at it as like it's absolutely okay.

Ben Cutler: 11:04

Where it can sometimes step out of being okay is the same thing, the same issue recurs and recurs and recurs, because then you've got a pattern where there's no growth and I think that can tell you something else. But that doesn't typically happen. Typically, what happens is we sit down, we work out what we can do better and that issue solved. And you know, within a little bit of time another issue pops up and then we just address it that way. But I think it kind of creates a the issue is not the issue, it's kind of how do we solve the issue?

Carol Park: 11:40

Yeah, yeah, that's so well put and I know even as you talk about that. It's because you model this from the top down and a lot of times people think that you know vulnerability and humility are perceived as weaknesses, especially in leadership, where you're supposed to be strong and have all the answers and tell people, and so you're modeling this In your words. How would you describe that? Actually, vulnerability and humility and leadership is incredible strength, not weakness.

Ben Cutler: 12:51

Yeah, that's a really good question. I think my view is that you want people to support. If you want people to support you, they have to feel like they have some agency. They got you know, they have some control of the situation. Talented people they really want a mission, they want to know what the mission is, but they also want the flexibility to you know, do the mission. You know, at times I need some support and sometimes I need some understanding. So I think when you take that approach it takes away from that top-down model because you're sort of sharing that control with other people.

Carol Park: 13:29

Yeah, it's really building a team right, because they then feel like not okay, I'm tasked with this, I don't have agency, I don't have any freedom to try things or whatever. I just have to do the task and especially, as you said, for talented people, that they kind of feel like they're pigeonholed and probably won't stay very long would be my guess.

Ben Cutler: 13:55

You've met some of the people that I work with. These are phenomenally talented people at different stages in their career. We absolutely want to maximize the time that they stay with us, knowing that at some point they will move on to bigger and better things, and when those days happen, I'll be sad but be happy for them. I think it's really though it's really important. You've got to kind of create those sort of conditions and I think McChrystal's principles really apply here. When you talk about you know he uses the word radical transparency, but talk about transparency of the vision and everything else If everybody understands generally what you're trying to do, where you're trying to go, I always refer to it.

Ben Cutler: 14:34

Well, you know the tank is going to Europe and we're in Canada. Right, we're on the East Coast of Canada, we're going to Europe. There's a lot of things that can happen on that journey that are the control of other people, but we generally know where we're going. That's really important. So if everybody understands what we're doing, then mission is clearer.

Ben Cutler: 14:55

Along that journey you then work out well, how do you handle the decisions that need to be made? You make those decisions efficiently. You make those those decisions in ways that empower people and empower growth, creativity and everything else, because it's the creativity and all of the things that agency gives people that really help move the needle in success. And then you know, inevitably, if something goes wrong, you have to make it safe to have the conversation about what did we learn here and you look at those as opportunities, because I think you have to take the approach that if you've given people the responsibility, you trust them.

Ben Cutler: 15:32

You know they have the skills, the skills. Your job is to help maximize their success and that can be through mentoring them, providing some support. I play a variety of roles. I play a lot of support roles, people in the organization and I look at it as my, my obligation. If somebody is doing something and I have some domain expertise that can make their life a little easier or make what they're doing a little clearer or help expose the success a little with a bit of clarity, that bit more clarity.

Carol Park: 16:03

It's absolutely incumbent on me to do that, because that's my way of encouraging what they're doing yes, as, as you said, I have seen some of the people that you continue to grow and give opportunities for, and have seen you mentor, which is kind of how I started, like I've seen your leadership ability and your skills, which is why I think your company has found so, so much success, and the people who work really with you. I would say with you, not even for you, even though I know that you're the leader, it really feels more, even as you describe it, that it's a team and, yes, you are the leader and they know that, but it seems like it's so much of a power with, not power over.

Ben Cutler: 16:54

I think that's a really great way of describing it Like I'm privileged to work with such a talented team. There are people that have domain experience far in excess of anything I can come close to in some areas and in some areas I have a little bit of experience. In some areas I have a little bit of experience. We have a phenomenal team and we have to create the conditions that allows the team to succeed in the best way they can.

Carol Park: 17:21

Yeah, yeah, absolutely, absolutely. So, as a leader like you've been vulnerable. You've had times, I'm sure of things didn't go well, as we allude to. Are there any of those? You can think of that, how it maybe changed things or impacted the culture in your company, your, your own ability to be vulnerable and own own when things didn't go so well so off, put me on the spot there.

Ben Cutler: 17:57

So I'm off the top of my head, I don't I can't come up with any specific examples. But one thing, um, I think you know this I'm, I'm quite a dyslexic. I'm quite dyslexic, um, and you know, being a little mature at age, as a kid, that was perceived something quite differently than it is today. Um, through my career, I've learned to realize that my dyslexia is actually more of a superpower than a challenge. But it does create challenges. Sometimes when I, you know, read, read an email quickly or read a Slack message quickly, I might misinterpret it and give the wrong answer.

Ben Cutler: 18:33

And so you know, I think, for me, I'm very open about owning the fact that I'm dyslexic. I don't, I have no qualms about it. I have no, I'm more than happy to the fact that I'm dyslexic. I don't, I have no qualms about it. Um, I have no, uh, I'm more than happy to own the fact when my dyslexia makes itself known, um, and I think that's a really healthy thing. It's like it's. I'm okay, I'm very comfortable, um, with the limitations that I have, because I know they're balanced out by some other, uh, great strengths. But every so often it uh dyslexia shows itself and everybody's really understanding of it, which I appreciate. But I know that I'm not. I don't always get it right and, yeah, to me it just seems like kind of the other side of the equation. I think it's important for me to make it safe for everybody else and but that also applies to myself and everybody else in leadership roles actually I know you said that was like oh, off the top of your head.

Carol Park: 19:22

That's an incredible answer around how you being vulnerable, you know, because sometimes when we have our own personal struggles and we all have them for you it was and is dyslexia, and so oftentimes we think that we need to hide those things that somehow people will perceive us as that makes me weak, not strong, and you just own that. And so you know, once again, the modeling which trickles down to building that psychological safety within your culture. How do you think that the psychological safety that the employees that work with you, how do you think that contributes to greater success or outcomes, and to the culture as well, to the culture as well.

Ben Cutler: 20:19

So I think when you work with really smart and talented people, they want to have some agency, they want to be able to contribute, they want to know the mission, they want to know the goals and if you take that away from them, they're not going to be happy and that's going to impact your culture. Yeah for sure. If you have people that are happy, that's going to contribute to the culture. Yeah for sure. If you have people that are happy, that's going to contribute to the culture. Obviously, hiring people that are can do the role you know can do, the role of generally a good fit to the culture helps.

Ben Cutler: 20:49

But I think there's a symbiotic cycle there. If you have really talented people and they're creative and they're early on in their career and they take on more responsibility, they're keen to do all of that, but they're also keen to grow and they can grow in their professional lives and when they do, they're going to achieve more success. They're going to achieve more success with the company, they're going to achieve more success within the company and then, as a result, it's sort of this sort of feedback loop that is created. So the company wins, the employees, the employees of the team members win.

Carol Park: 21:22

Yeah, absolutely, absolutely so. Direction like for your company, as you're creating this psychological safety. How much do the employees like you talked about you have the meetings that y'all meet like in this sense of agency on this mission. How much do they get to contribute? Obviously, you have kind of a given but your missions I don't know that the overall mission changes, but maybe some of the directions, or sometimes when you have to pivot, how much input do your employees get to give with that?

Ben Cutler: 22:06

So I think, if you take kind of the overarching vision and strategy, that's that stuff that everybody gets to contribute to because we share lots and lots of information, but that's sort of at the very high level, the sort of the stuff that's kind of cast in stone but it gives a lot of remit for flexibility and creativity. So I think everybody gets to kind of contribute in various ways. You know we share hey, this is some feedback we've got or this is what we're thinking. What do you think? I know, sort of from a product side, sometimes there's a one-on-one or group conversations that are had and all sorts of different ways of sort of sharing that information. But I think the real opportunity comes is once we're all on side with the mission and we tend to get there really easily. Once we're clear on it is the exciting stuff then becomes sort of like how do we execute on that mission and sort of creating those spaces where people can be creative?

Ben Cutler: 23:02

You know, there's an example this month where we sort of changed one of our foundational tech stacks which allowed us to do something that we couldn't do before, and somebody who's not very senior in the organization started doing something.

Ben Cutler: 23:14

That's sort of snowballing into something that's going to be quite positive. And that was to me a really, really exciting thing to see, because it wasn't a top-down decision. It was quite the opposite. Somebody who had a problem they wanted to solve saw that this technology could solve this problem, had a little bit of success, and then all of a sudden we're saying, yeah, let's see if we can roll this out and make a fundamental change. That's really neat to see, because that person has the ability and is working in an environment where they can make that change. They don't have to run it up the ladder you know two or three levels and say well, ben, what do you think of this? It just happens. It happens in a non-consequential way. We learn from it and then we can. We can, we can say, hey, that's the way we can sort of use that knowledge in different ways for the greater good.

Carol Park: 24:00

Yeah, that's that personal agency that people actually believe that they have not. Just they're told that they have it, they know they have it, and so they just do it and then, and then it starts to unfold, and then the teamwork comes in because of this culture that you've you've built within the company. So, yeah, so any kind of parting words of wisdom, advice that you can leave us with today.

Ben Cutler: 24:30

So I think what I talked about is the stuff that I think works for me. For me, it's a journey. I will be fine tuning and learning until I'm not. It will definitely evolve over time. I got some great feedback about being more direct earlier this year or late last year, and that's something I've incorporated in into my style. I sometimes I find it hard to be to the point, indirect. I've worked on how I can do that, but in keeping with my the other principles, and so being open to change, uh, evolving over time is, uh, it's something that you can expect should happen. I don't think you need to be perfect. Um, you should expect to make mistakes. That's okay. You want to learn from them. It's just like you expect from your team. You expect them to learn, so you know. I don't think you need to get it right. 100 at the time it's sort of oh, that didn't go according to plan or as I expected. How could I handle that different? Or is there a? Is there a root cause? I keep encountering these things.

Ben Cutler: 25:30

I can modify that and I can solve this issue going forward I guess the last thing is there's lots of great resources available to help you develop your leadership style. A lot of them will tell you what you have to do. This, I think picking and choosing the things that really resonate with you, and so your style can kind of be the compilation of the good, instead of taking this really rigid. Well, this book says I need to do these 10 things. Five of them may be absolutely relevant and to to you, you to your role, and resonate really well, and the other five maybe feel like, oh, they feel like they might, but they don't, so just pick the ones that work.

Carol Park: 26:11

It's kind of where we started, where I was asking about how you came to be that way and you said part of it.

Carol Park: 26:18

It's just, it's kind of built in. It's just kind of who you are as a person which I believe that to be true as well and being able to be authentically you. Again, we're still all growing, learning along the way, but taking who you are and then the leadership tools that resonate, that you may read about, but I love that you're staying grounded in you. You know what you know, and then being open to growth. And then being open to oh yeah, I could do that better. And again then your employees say, oh, he's open to that, I can be too. This feels really safe here. And so, again, I know that your company has been really successful. It's continued to grow. You've grown the product, you've grown your employees. So I really just want to say thank you again for taking time out of your day to come on to the Courage Unmasked podcast and to share your wisdom and knowledge as a leader with us today, ben, I so appreciate it.

Ben Cutler: 27:26

Thank you, Carol. I really appreciate the opportunity. It's been a lot of fun.

Carol Park: 27:30

Okay, well, take care.

Ben Cutler: 27:32

You as well.