Leaders in Conversation with Anni Townend

Anni Townend in Conversation with Scott Sherwood, Vice President of Engineering

March 11, 2022 Anni Townend and Scott Sherwood
Leaders in Conversation with Anni Townend
Anni Townend in Conversation with Scott Sherwood, Vice President of Engineering
Show Notes Transcript

In this first episode in the second series of Leaders In Conversation, we are delighted to welcome back Scott Sherwood.

Back in 2021, Anni had the pleasure of being in conversation with Scott and his then 7-year-old daughter Sophie Harvey Sherwood who shared her experience running to celebrate inspirational women.

Scott participated in the Just Running It challenge, a 365 mega challenge in which he aimed to run 10km every single day for a year in aid of Glasgow Children’s Hospital Charity and was joined by Sophie too.

The parallels between running and leadership 

He talks with Anni about his inspirational experience with the Just Running It challenge, not only completing the challenge but running nearly 4200 kilometers and continuing to maintain running daily into 2022.

Throughout his career in software engineering, Scott has found many parallels between running and leadership.

Scott discusses how 'personal bests' in running are a great analogy for agile software development. Running is the ultimate agile approach to a problem where some days you get personal bests and other days take much longer.

Some weeks in projects can be amazing and moving forward and other weeks things will struggle. Scott suggests that we must accept the ‘ups and downs’ as innovation is much more uncertain. 

Dreaming Big

Scott shares his motto that “Great leaders are not born or made they are chosen by the people they inspire”.

He shares with Anni that his motto inspires everything he does in life even if its to encourage even one person to believe they can be more than what they thought. Whether that is the confidence to get running or as his role as a software engineering leader. 

He believes that many in the workplace constrain themselves by not dreaming big enough. His experience with the running challenge has shown others that you can achieve anything with sustained effort, self-belief and the support of others. 

Creating a resilient workplace culture

They discuss the importance of staying healthy, in order to run but also stay healthy in order to lead and create a healthy workplace culture in which people can be their best even though they may have days, bad days and good days. 

He said that “The thing that really appeals to me about running, particularly Ultra running is the way athletes talk about it. They very rarely see that as a physical challenge it is all a mental challenge. And I think in the corporate world, the vast majority of help navigating and leading is really mental strength and finding you have been resilient both for yourself and for your people” 

Think bigger than you ever thought possible 

Scott is passionate that we should all dream bigger and ‘higher than we ever thought possible’ and that even if we don’t get there to not beat ourselves up- just work hard and be consistent- whether it’s a running challenge or a workplace one.

Listen to the full episode to hear about:

  • Scott shares his personal leadership story and participation in the Just Running it challenge
  • The parallels between running and leadership 
  •  Importance of a healthy culture and encouraging others 
  •  Leading through ups and downs 
  •  Dreaming big to achieve your goals 

Discover more, donate and connect with Scott

You can follow their progress and discover more on justrunningit.com which has links to the pair’s YouTube channel  and their fundraising page.

You can also follow Scott on Instagram and Twitter @scottcsherwood


Anni Townend  00:00

Welcome to Leaders in Conversation, a series of podcasts in which leaders share their inspirational leadership stories, their insights and experiences to help build confidence and courage in our leadership. In this episode, the first in the second series of Leaders in Conversation, I'm delighted to welcome back Scott Sherwood. 

Scott, I first met you when I was working with a group of senior leaders in the company where you worked as Vice President of Engineering. It was here that you shared your personal leadership story and your challenge of Just Running It supported by your home team, your young daughter, Sophie, your wife, family, friends, and of course, your work colleagues. I invited you to be a guest and had the pleasure of being in conversation with you and your young daughter in the very first series of Leaders in Conversation. 

Thank you for being back on Leaders in Conversation. I'm going to be asking you Scott about where you have got to in your Just Running It challenge and the challenges and support that you've needed and the parallels between running and that of leading.

I'm going to be asking you about how you and your daughter's motto, ‘keep on going, we keep going’ has helped you to do just that, in particular, when you've had setbacks. I'll be asking you about the importance of celebrating small wins, of having the support of others as you go along. And the importance of having a healthy culture and how we can lead for that. 

Scott, let's begin with where have you got to in you're Just Running It challenge?

Scott Sherwood  01:51

It's a good question. So, the challenge itself was to run 365 10ks, one every day for the year of 2021. And we managed to achieve that. So, we successfully completed the challenge. But not only did we complete the challenge, we managed to run nearly 4200 kilometres. So, I did quite a few extra miles along the way. And except for two short days where I had to go in for some tests, in the hospital, I have managed to maintain the streak for 410 days thus far. So, it's still going and we'll see how far we can get over 2022 as well.


Anni Townend  02:39

That's incredible. Scott, well done. You began by saying we do you run with somebody else? Or do you run on your own.


Scott Sherwood  02:48

When I actually run I tend to run on my own. Occasionally, on weekends, my daughter comes with me. She was a big part of the challenge. But for me, it's been an incredible team effort. My wife has had to put up with making sure I'm well looked after throughout the week. My daughter has been a key part of the fundraising as has the extended family. Also, even people like my work colleagues, I’ve had incredible support across a wide range of people. So even though the majority of the running was done on my own, it's been a massive team effort.


Anni Townend  03:28

Which is great and huge parallels between that and leadership and working in a team. What are some of the things that you've learned about team working from just running it?


Scott Sherwood  03:42

I think there's a lot, a lot of things for me. I used to have this motto, which is great leaders are not born or made, they’re chosen by the people they inspire. And the thing that I always wanted to do with, with everything that I've done in my life is to try and just encourage even one person to believe that they can be more than they ever thought. And not only has my challenge inspired a lot of people into running, least of all my daughters whose now got into running, but she prefers cycling. I think in the workplace so many people constrain themselves. So their careers are curtailed just because they don't dream big enough. And it’s something that I've been able to, through running show people that the effort that you put in, as long as you have it over a sustained period of time you can achieve anything you want. It's much harder in my industry to see that. We're software engineers and for the vast majority of the world they don't really understand what we do. It's a little bit magic. But with running it's very visual.


Anni Townend  05:12

There are two things that are Scott that really chime with me, and one of which is the belief of others in you, which you began by talking about around leaders being chosen by the people who follow them or with whom they engage, and work with them. And there's something about the belief in you of others, but also our belief in others, that I believe is very, very encouraging. I often say that I wouldn't be doing what I do partner with leaders, if it hadn't been for others believing in me, and particularly believing in me when perhaps I didn't believe in myself. So that self-belief being so important. 


And the other thing which you mentioned around dreaming big, you know, I think, how wonderful that you had a big vision that kept you going, and a picture of what that looked like, and how sometimes that is difficult to create that purpose, that big vision, particularly when people don't perhaps understand what we do, like engineering, software engineering, but nevertheless, that big picture, the why is so important, I think, to, to our leadership and to leading together.


Scott Sherwood  06:39

Absolutely, it's given me a really good analogy for agile software development. It's a project management methodology, very popular in the software industry. And, so many people have used traditional project management methods and try to rebrand them. But with running as the ultimate agile approach to a problem. There are days where I took 10-15 minutes longer than my personal best. The analogy for me is, when you have a team working on a problem, some weeks, they will absolutely smash it, they'll be amazing. And you get things as a business leader that will move you forward. And there'll be other weeks where they really, really struggle. And I think a lot of people strive in business for a level of consistency, which is really, really important. But when you're innovating and you're building things that are new, there is huge uncertainty, you need to accept that there are those ups and downs. And for me that it was really crazy, I didn't expect it. But when I was running the synergy with software development, the challenges we have, the good days, the bad days. And ultimately, at the end, the achieving the goal. It was quite interesting to see how my work and my running life ended up getting merged together.


Anni Townend  08:12

I really get that. And it has me in mind of a lovely quote that one of my colleagues Emily Court, gave to me, which is ‘When you're not able to give certainty, give confidence’. And there's something about leading and leading through the ups and downs, the good weeks, the bad weeks, having the confidence to know that we’ll come through that. Even though there is a lot of uncertainty, all that we can give others is confidence when we're not able to give certainty. And what you've just said, really puts me in mind of how important that is. To, to keep on going despite the things that may come along our way and you've had a few things come along your way setbacks Scott in your running. Again, what have you learnt from that, that has helped you in your leading?


Scott Sherwood  09:16

I think regardless of whether it's in the commercial world, whether it's in running, whatever as you do in life. If you set your mind to something, just keep going. Keep your head down, you have bad days you have good days. But first and foremost, look after yourself, make sure you're healthy. And make sure you're both mentally and physically healthy. But then after that, just don't beat yourself up over things. Just keep going. When things get hard that's usually when, when I started to think about quitting. And it was only very early on, and eventually got to the point where it was no longer about getting a specific time, it didn't matter if it took me all day, or if I got a personal best. The goal was to complete that every one of those days and get that destination. And it can seem, it can seem insignificant. People thought this was crazy after 300 days of running. It can seem like an insignificant thing. And you can start to beat yourself up if you're not doing the same times that you did before. But reality is just getting to that point is almost unique. When you're in the workplace, you’ve got to realize that where you are today may not be as good as where you're at yesterday, but tomorrow is could potentially be even better. That was my biggest learning. And it gives me a lot of confidence as well. There's been tough times professionally and personally over the last year. It was really important for me to have running last year throughout a difficult period.


Anni Townend  11:44

It sounds like it's been a way in which you have taken care of yourself through keeping on going through running has helped you to look after yourself. And I think you mentioned about staying healthy, in order to be able to run, but also staying healthy in order to lead and to create a healthy culture in which people can be their best even though they may have days, bad days and good days. 

What are some of the ways in which you have looked after your mental health and emotional health and physical health during the past six months, which you mentioned have not been easy, professionally? We're all leading through a very particular time, of uncertainty, many of us working from home, not all of us, and now combining working from home with going back into working from the office.


Scott Sherwood  12:55

I think you make a good point. The first few months, a lot of people appreciated working from home. They appreciated the fact their work life balance. And from a commercial standpoint, as a business, we saw very, very little change in terms of productivity, which was fantastic. But I think over the last few years, the thing that’s really struck me is that that mental health piece. I think that we can underestimate how much isolation and has… how much has impacted vast swathes of our community. 

One of the toughest things from is - I am someone who, who likes to get around our team. So, I like to be involved. I like to be very visible with my engineers. And I like to spend time with everybody getting to know them getting to know their work. And there's only so many hours in the day when you've got to do that, through a call is much harder to pick things up. So, in some ways, we become slightly more, more siloed, our social groups in the workspace become much smaller. And for software engineers this is something that is a particularly challenging thing anyway. We're not always the most sociable, but we love people. And one of the hardest things as a software engineer is when you have a problem and you're on your own to solve. That’s why team working is so important in our industry. So, when you make that remote, it 90% of the time, it works really well. But that 10% of the time we're not able to come together has been massive. For me run running has actually tackled all of those challenges. For me, the mental side of getting out into nature, switching off, and after I got through the first few months, and it no longer hurts, and you get into a very meditative state, so mentally running a massive amount and physically - I lost a lot of weight. Not that I was overweight, but I stopped drinking, just because I thought it would help my running performance. And I've noticed huge physical benefits.


Anni Townend  15:49

It's a really good example, Scott, I think of how connected our physical, mental, emotional, and spirit energy is, and how when we take care of one aspect of who we are. Another aspect of our energy is also greatly improved, you've mentioned there the, impact of isolation and the importance of connection, and how in the absence of that, those casual encounters and opportunities to share problems in the moment that the running has helped you by way of meditating and of helping you move through something. I'm struck by some of the choices you've made, like not to drink, and what impact that has had on you. I'd love to hear a bit more about that.


Scott Sherwood  16:49

Initially, it was difficult, a lot of people thought I was crazy, particularly being from the west of Scotland, it's not the most common thing for people to do here. It was a little bit challenging initially, where friends and family got used to me going to football matches or parties and events. Over time it became quite easy. Getting up on a Saturday morning, spending a couple of hours running is far more appealing to me than then being hungover on a Saturday morning. I had one glass of wine at Christmas. And to be honest, I think I went off the taste of it. So it's something that I probably won't really go back to. It was a really strange experience. I never really intended to be two years. And it was initially just I started the year before running. And then the year of COVID, I decided that I was going to try and do it for a whole year just to see if it was possible. And after I'd done it for a year, and I had set my mind on doing a year’s running challenge it became two years. I like to do things that are that are hard and require effort over a long period of time. You mentioned the mental challenge. The thing that really appeals to me about running, particularly Ultra running is the way we the athletes talk about it, they very rarely see that as a physical challenge it’s all a mental challenge. And I think in the corporate world, the vast majority of navigating and leading is really mental strength and finding all you have been resilient both for yourself and for your people.


Anni Townend  19:22

I really get that. And I very much think of resilience, going along with confidence and that mental strength that you referred to, which also comes with vulnerability, the strength to ask for help when we most need it. And of course the strength to accept help when it's offered to us is so important. And I think that opportunity to grow our leadership through having a practice which you have in your running and running in nature. So, something else that occurred to me, Scott, while you were sharing, what running is for you, and how it's helped with your mental confidence and resilience is the importance of getting out into nature. And the nature of working from home is that many of us are sitting down for long periods of time. Whereas you're getting up early every morning and getting out there, running and running in nature has become part of your rhythm part of your every day. What is it about getting into nature, and what has nature given you?


Scott Sherwood  20:40

I think it gives you a new found sense of what is important and the world. I think we can get quite caught up in our modern world, which is really driven by consumer behaviour. And I think in the workplace, it's a great thing when you're super passionate about what you do. But it really doesn't leave much time for you to reflect and, and really create the vision path for yourself, for your people, for your organisation. To get out into nature really allows me to, to switch off a little bit and start to reflect on much simpler things, the things that I think people have taken for granted for such a long time. 


My niece, she just turned 18, she actually recommended a musical to my wife and I called Tech Tech Boom. And it was written by Jonathan Larson, the original author of Rent, and one of one of the songs in it, he has a line, “Cages or wings, which do you prefer, as the birds?” And, and for me, I listen to that song almost every run for maybe the last three or four months. And when you see birds flying around, they are free, they are together, they find a way of achieving amazing feats, migrations, and so on, so forth. And I realised that if we really just look at nature and look at the wonderful things that come through nature, we can learn a lot and I actually take a lot of that back to my leadership style. 

How do we empower people? How do we allow them to achieve great things by setting them free? Whereas I think, organizational methodologies are about creating cages. Words like ‘protect’, ‘holding people account’, these are caging words, in my opinion. But if you want people to take account, if you want to create environments where people can, can lift themselves up. I think maybe I've just got a little bit philosophical in old age. But that's what I see when I go out running now. And it really resonates again, back to the workplace for me.


Anni Townend  23:42

That's really great. Scott, I particularly like that you do have a philosophy about leadership, because one of the things I think about is, as a leader, it's about developing as others as leaders, so having a philosophy of leadership, which you do, which is to create the conditions by the sound of it, which helps set people free, to be creative, to be innovative, to, to take account to take responsibility, so you're giving them something which you're then enabling by the sound of it, enabling them to take and what you're doing as a leader is providing the conditions and enabling culture in which people can fly freely, but together.


I often use the analogy and Sophie, your daughter will be more familiar with this with her love of cycling, I think of how cyclists cycle in ‘V’ formation, but also how you see birds, flocks of birds, sometimes flying in ‘V’ formation. And what I understand and have read about this is that it's not always the same birds the same cyclists at the front of that V formation, that people take it in turn. So, we're flying together, or cycling together, we're looking out for each other we're bringing each other on. And when we get tired or weary, we're able to be helped along, and somebody else to take the lead. And I love that analogy, and you're talking about the birds makes me think of that. And the importance of looking up, one of the things that I've been thinking about, since the beginning of January, is the importance of for me, of being able to see the horizon wherever I am. So, you know, from working with me that I'm a big fan of encouraging leaders to have paired conversations outside in nature, if nature is there, but simply walking side by side, of being outside, whatever the weather, and I've realised that for me, there's something about being able from my shed, which is my office, to see the horizon. And how that reminds me to keep looking up. And that requirement for leaders to think strategically and to look up and to horizon scan, at the same time to look within that self awareness is really important. And being aware of what's happening around us the context is really important. And a really important part of that is the culture. And I'd love to hear you say more about how you help to lead a healthy culture, a culture, which does set people free, and which they are enabled to take account to take responsibility, and are supported in doing that.


Scott Sherwood  27:02

I guess from a leadership standpoint, I lean heavily on Dan Pink – Three Pillars: Autonomy, Mastery, and Purpose. I think it resonates really well in our industry. Software engineers, we've never really had too many challenges in the workplace in terms of mass redundancies or no work. It's a very high demand low supply industry and always has been. As a group of skilled workers, the one thing that software engineers really look for, above and beyond anything else is a sense of purpose. They need to feel that they are doing something significant with their life and ideally for some bigger cause than themselves. And I think, again, that speaks to maybe my running challenge, we raised a significant amount of money for charity as well. And you tend to find a lot of people in that industry, doing things so much of that also talks to their contribution to open source projects where they gave their time and effort for no money to benefit the wider community, like you said, cyclists or birds, And then the autonomy. 

Autonomy for me is really about creating an environment where people have clear decision-making rights, and ideally decision-making rights slightly beyond their experience level to help them grow. And if you can create those three things, people will flourish. And they will do things that you never expected of them. But the one thing that you have to do in an environment like that is: when they fall down, when they have a challenge, you have to take flak, it has to be on you, it can never be on them. It always has to be your call. And when they succeed, it has to be their call and you have to raise them up, push them to the front of the peloton and make sure that they get the visibility. And I think too many leaders want to be at the front of the peloton and are very happy to avoid taking accountability themselves when things are going wrong. But that's ultimately how you grow people and you grow teams. And it's the toughest part of leading. But for me that's the framework that I work with and if you get those things right, the culture in your organisation will start to become self-sustaining, and you'll find out all leaders do the same for the people all the way down the chain. It's been an incredibly powerful framework.


Anni Townend  30:14

It's a great framework, I think purpose mastery, and autonomy and dreaming big, which is something you spoke about at the beginning of our conversation today. Dreaming big, having a sense of purpose, creating a shared purpose that is, above and beyond, whilst linking with the everyday is so important back to the having that powerful, why I do what I do in the every day. And the difference that I want to make the contribution that I want to make as a leader. You mentioned, Scott about fundraising. And I know last year you were fundraising for a children's ward, at a hospital where your mum works in Glasgow, are you fundraising this year?


Scott Sherwood  31:07

I didn't have any plans to fundraise this year. But what I am doing is I'm supporting a couple of other people who reached out who have started their own 365 Day Challenge. So, there's a gentleman called Mike, he’s raising money for the ambulance service, and specifically for mental health provision for the ambulance service. Because they have got an incredibly tough job. And a lot of people really think about the trauma and challenges that they face. And so, I've been speaking with him and trying to help promote some of his work. And there's all those that are looking to help kind of almost boost their fundraising rather than start my own. And it's, again, your analogy is great. It's a little bit like being at the peloton. Last year, I got to raise it the front. This year is my time to support the other people.


Anni Townend  32:15

That's great. And you do other things to support giving of your time, I think as well, Scott, don't you by way of encouraging people into engineering.


Scott Sherwood  32:29

Yeah, so I've been I've been lucky enough to mentor numerous software development programmes. I also work very closely with a company called upfront. It's led by an incredible woman called Lauren Curry. And that's about trying to empower young women into senior business positions, building confidence, understanding business strategy, and just really feeling like, like they belong at the top table. Because I think for so long. That's the confidence aspect as what's held people in general back but that's certainly her mission and purpose to try and make sure young women can overcome some of those challenges. And with a young daughter that's quite close to my heart as well.


Anni Townend  33:21

And is that what she wants to do? Your young daughter Sophie? Does she know what she’s dreaming big about?


Scott Sherwood  33:29

At the moment, Sophie is still finding her way. She's experimenting with a lot of different things. She's inspired by people like Lauren and our business partner, or old business partner. They were both service designers, so she likes design, she gets to do design at school. She's been speaking about going into architecture. She likes teaching. She reads like, like nobody I've ever met adult or child. And so, she likes the idea of being an author and an illustrator. So, at the moment it’s a wide range of things she's looking at and very encouraging because, I think, the more she understands and looks at it, the more likely she is to find her true passion when she's older.


Anni Townend  34:25

And master it as well. It sounds like she'll have mastery in a number of different things Scott as well as autonomy and hopefully gets to lead in the way that your role modelling leadership. What when you were growing up what was your dream Scott? I don't think I've ever asked you what did you dream big about when you were a young lad Sophie's age of eight years old or there abouts?


Scott Sherwood  34:54

So, this is a strange one. My dream was to go to university and it was, nobody in my family had gone. My dad had made a comment when I was born to the nurse, and he always maintained that the day I was born, he said to the nurse, “My son's going to go to Glasgow University”. And that was almost, it became an ambition that became something that kind of grew me in it. It was really super important. And it was definitely driven by my family. And it was all about education that really speaks to that mastery piece. But I was very lucky not only to go to university and graduate. I went on to do a postgraduate and ended up teaching there as well. So, so from that point onwards, everything for… everything was up in the air. And I had to find a new dream back then. But that was my early dream as a kid,


Anni Townend  36:00

Which you achieved, and no doubt celebrated going, being the first in your family to go to university and the importance of education and your commitment to education to mentoring, coaching, leading others creating, as we've already talked about that environment in which others can learn and grow and be themselves - become more of themselves with that sense of purpose, mastery and autonomy. 


Scott, as we come to the end of our conversation, what three things do you think it's most important for people looking to grow their leadership, in particular, their confidence and their resilience, to take care of to pay attention to, from all the things that you've shared with us today?


Scott Sherwood  36:52

The biggest one for me is, is understand who you are and what you believe. And don't ever compromise on it. I think there's periods in your life where your belief system and what you stand for, you have to be adaptable, you have to fit in to be a successful member of a team. But don't ever stretch them so far that you no longer feel that you stand for, for what you believe in. That's number one. 


Number two is, is really think bigger than you ever think is possible. Because it can be quite surprising how possible things are, for me University was a pipe dream. The type of possession I hold today was just I don't think it would ever have been on the cards as I would have thought. And where potentially I will be in the future. Who knows? I think aim higher than you've ever thought possible because, and just except if you don't get there, except it, don't beat yourself up about it, you've got a whole lifetime to live. Just keep going, try your best, work hard, be consistent, and it speaks to my running as well. If you come up with crazy challenges, you'll get them done eventually, you might fail the first time, you might fail the second time but you will get them done. 


And the third one is don't ever forget where you came from, and treat everybody the way you want to be treated yourself, irrespective of their position. I think I think we can quite quickly forget the challenges and struggles we've gone through as individuals, and be overly critical of others who are going through their journey. And I think we really have to, we have to make sure we are always putting ourselves in other people's shoes. Empathy is super important. So, they would be my three things.


Anni Townend  39:11

They’re three great things Scott, thank you so much for sharing your wisdom, your insights and for encouraging us all to keep going and what to pay attention to. 


To find out more about Scott and his just running it challenge, do follow him on Instagram: @scottcsherwood 


To listen to other leaders in conversation do go to my website, annitownend.com 


If you would like to be a leader in conversation, please get in touch via my website. I look forward to hearing from you. Thank you for listening. And thank you Scott.