E20: From Manager to Leader: Navigating the Journey with Jonathan Stern | VP Mulesoft, Salesforce

I'm not an impartial observer when it comes to coaching and mentoring because a coach or a mentor can hold up a mirror and sometimes we're so close to the action, we can't see things. So having someone who, who can actually hold up a mirror and show you what's happening and has another set of eyes to help you because that will help you focus on what you need to learn.

Welcome to the High Performance Sales Leader Podcast, where we bring you actionable insights for breakthrough results. Today, my guest is Jonathan Stern. Jonathan, thank you for joining us today.

You're welcome, Preeth.

Thank you. Let me introduce Jonathan. Jonathan is one of those rare people who has worked with every different size of technology company. He has worked at the large end with IBM leading the WebSphere team. He's been the managing director of Informatica and then joined MuleSoft when there were 8 people in region and worked with them through the IPO and then the acquisition by Salesforce. And that is just priceless experience. Moreover, he started his career in technical, on the technical side, moved through into sales, started managing people, and then started managing managers and eventually transitioned into coaching leaders. And so today, I'm so thrilled that Jonathan, you could join us.

Thank you. Good to be here.

Now, I know that you have woven your experience through different roles. And you're now spending a lot of time coaching leaders. I understand that you are involved in leadership coaching, go-to-market, deal clinics, forecasting, everything that I guess solves the revenue problem, which is a huge problem. And there are a lot of people trying to solve that problem. So tell me first, Jonathan, about your interest and passion to move from a corporate leadership role into coaching.

Yeah, thanks. You're right. It is absolutely a passion. I'd probably trace it back to 2007. So there was a particular event in 2007. I was working at IBM at the time. IBM sponsored my visa to come over to Australia from the UK. As you mentioned, I had a number of different roles, including the WebSphere job, running the WebSphere business at IBM. Now, in those days, IBM had a network of executive coaches, global executive coaches, and one of them came over to Australia, came over to Sydney, from the US, from Atlanta. And I got to meet him and he invited me to join his program. So, he had a program of leaders globally that he would coach on a regular basis. So, he went back to Atlanta. I said yes. He went back to Atlanta. I stayed in Sydney. Excuse me. And then we started the coaching on a monthly basis. Now, looking back on it, it changed everything. It changed the trajectory of my career. I wasn't too sure to begin with because I thought, this is going to be good, but it's another meeting for me. I've got enough to do already. But it was just amazing, the whole program. Mark is the name of the coach. I still have a relationship with him, a coaching relationship with him now. He did a number of things. One of the things, the first thing he did is he helped me define my goals, really define my goals. He was a sounding board. He would hold up a mirror for me. He would challenge me effectively on these monthly calls. He would challenge me when needed. If my thinking was fuzzy or I hadn't thought things through or I haven't followed through on something, he would absolutely push me and stretch me. He was a bit like a personal trainer. I can imagine a personal trainer sort of stretches you, pushes you, but has your interests, your best interests at heart. And that's what he did for me. He always had my best interests. And as a result, there's no doubt I stretched. As a result, he, I always felt he was in my corner and he was someone to help me. Now, Mark left IBM a couple of years after that. He set up his own coaching business and I maintained, even though he went private, I maintained the coaching relationship. So valuable was it for me. And I continued with that and we still continue today. We don't have telephone calls anymore. We have video calls. Over the 16 years, I probably met him about 3 or 4 times in person when we happened to be in the same city at the same time. So he inspired me and I felt this is something I could do and I could help other people. As I was thinking about stepping down from leadership, I wanted to pursue coaching because I felt I could be of service. I felt I could help. Other people. I had some experience and I wanted to help others in the way that Mark helped me. So that was one part. The other part, just quickly, is I really felt coaching was an extension of what I'd been doing previously anyway. You mentioned I was a technical person originally and it was, this is a very long time ago. I was encouraged by the MD of the company I was working for to move into sales because they felt they saw something in me in terms of the curiosity. the questioning. And that was natural for me. And I went on and learned more about how to manage meetings and control meetings through questioning, and then went on to management and leadership, which were also extensions of that, and into coaching, which is an extension, the curiosity, the absolute interest in the person that you're coaching. So that's a bit of an indication of where the passion comes from.

Fantastic. And I was just thinking about what you said earlier, that Mark had such an impact on you that it's something that you want to be able to do for others because you've experienced that firsthand. And not long back, we had another guest, Simon Horrocks, on the show who was talking about some really positive experiences he's had with past managers or people that you come along earlier on in your career who really make an impact and make you want to be better for the people that you encounter. And I see that theme playing out again. So tell me, you— I know that your employer became your first client. So tell me a little bit more about how did you make the switch from obviously as a leader to to actually coaching leaders? What was that like?

So, I had this in the back of my mind as I was going to step down from leadership. I felt that my future was going to be coaching. I really wanted that to be the case. And so, what I would do is I would take any opportunity to coach. I'd like to think I'd incorporated coaching, a coaching style into my leadership anyway. So, that was part of the day job. But I would take any opportunity to coach others internally or externally to try and improve my skills, master my skills in that. And anyone that you would talk to, if you were coaching someone with regard to their career development and they had a goal of moving, transitioning into another role, one of the suggestions would be maybe you start taking on some of the responsibilities of the new role and it becomes almost, it becomes so. And that's what I was doing. I started coaching internally and externally. Then I got my certification, my formal coaching certification from the International Coaching Federation. There was a catalyst. MuleSoft's acquisition by Salesforce was a bit of a catalyst. As we were acquired, I wanted to make sure the integration went well. And that was in 2018. And so I felt 2 or 3 years making sure the business was properly integrated into Salesforce. And I did that around about 2020. I thought this was the right time to step down. And I said to Salesforce that I'm obviously happy to help onboard my successor. And work with my successor. And then I wanted to pursue coaching. They pretty much knew that's what I wanted to do. That was my future. And they said to me, we need some internal coaches, some executive coaches. Would you stay on and be a coach? And I did. And then I was allowed to go and acquire customers outside Salesforce bit by bit. And now I've got a number of other customers. So you're absolutely right. I look back And maybe you make your own luck, but I feel I was quite fortunate in the way that it planned out. The way that it panned out. Yeah. My employer became my first client.

Fantastic. And look, often that's a dream for many corporate escapees, as I call them. I think sometimes they want to have, they're very restricted at a point of time in their life, in their job, and there's more that they want to Do experience, give. And again, congratulations on taking that leap. But I will say, you seem serenely happy every time I speak to you. So, it's obviously been a good move.

Yeah, it has.

All right. Now, in my day-to-day job recruiting for leaders and recruiting for account executives for SaaS companies, lots of SaaS companies. I often hear account executives say, I've been an AE for a while. I really want to move into management. So there is, there are a percentage of people who have come to a point where they want to move into management. I also know people who've been managers for a couple of years. And the big thing that though they might tick the box and move into a management role, what they may or may not realize at the time of making that transition that what will actually help them be really successful is building their leadership skills, right? So, can you tell me the difference between a manager and a leader?

Okay. Okay. You can find libraries of books on this particular subject, but I'm going to summarize it. I'm going to summarize it in one sentence. You manage things, But you lead people. So buy things, we're doing the buy things processes in a sales context processes. So it could be, I don't know, the commission scheme or the sales process or whatever it is. And so both of those elements are really important, the processes and the people, clearly they're both very important. I would see it as a hierarchy of needs. There's foundational elements where you put the processes in place and you have people, you have managers managing the process. And on top of that, you can build the leadership. Now we work with many organizations, smaller organizations that scale, and sometimes the processes don't exist to begin with. We've got these modular frameworks that can be slotted in depending on the order of priorities. And they're things I think you mentioned some of them earlier. They're sort of things like territory planning and the sales process with verifiable outcomes. There's things like forecast cadence, channel management, deal clinics, mutual success plans. So we plug those in depending on the needs. And then the managers manage those processes, very important foundational layer. And if that's all they do, they're still going to get a great deal of benefit. But in order to build something sustainable and longer-term, it's about leading the people to actually implement those processes and work within those processes and internalize them and utilize them for their own benefit. Because what we're talking about here, it's not just execution only, it's a set of skills that are needed. to do this effectively. And so the leaders really work with the people in order to utilize those processes to build something sustainable. So it's not just about this quarter's results, it's about future quarters so that you're able to scale. So a manager is transactional, a leader is transformational. A manager would look at immediate results, a leader would look at immediate results, but also Future results as well.

Fantastic. That, that there needs to be a poster with that, managers transactional and leaders transformational. I really like that. One of my favorite quotes that I've heard around leadership was from John Maxwell. I've read a lot of John Maxwell's writing. And he says that if, if you're a leader and you're going for a walk and you turn around and there's no one behind you, you're not leading. Basically, people, you must be able to inspire and engage people to follow the course of action that you have agreed to work towards the goals and do so happily and willingly, right?

Yeah.

So tell me, managers— go ahead.

I was gonna say managers have direct reports, leaders have followers.

Yes, understood. So, now, what are some of the personal transformation or mindset shifts that are crucial for a manager to making the transition to a leader?

There's a couple that come to mind. And the first thing is that the job of a leader is twofold. I've mentioned this a bit previously. It's delivering results, but developing the people. And it's getting the mind shift that the two aren't mutually exclusive. You develop the people, they're going to improve the results, and as a result, they're going to learn more and develop more, and the results are going to get better. And you start this multiplying effect. You get things moving as a result. You get a flywheel going and you start to get lots of these flywheels going. And that's what leadership It's about developing people. And when we work with smaller organizations, it's really noticeable. When they want to scale, it's not a case of them being able to just throw more people at growth, just throw more people. It is, they need to get an outsized contribution from people they have got. And that's the way you can do it by being this multiplier, by developing people.

Yeah.

So they develop better results on a sustainable basis. So that's the first bit. I'll tell you what, I think the second part is about, as a leader, or as a first-time manager, you don't have to have all of the answers. It's not a weakness to not have the answers. In fact, it's often beneficial to help people work things out for themselves. There's a really good guiding quote, I like to think of from Sir John Whitmore, who's the grandfather of coaching. And he would say, telling someone something saves them from having to think, but asking open questions causes them to think for themselves.

Very nice. Yeah, that's really good. In terms of this evolution, we're talking about a mindset shift, we're talking about evolution, are there specific skills or competencies that managers need to prioritize in terms of their own leadership development?

Yeah, look, there again, there are probably a couple of things come to mind. One is all around situational leadership. There's not just one style of leader. A leader is like having their number of different styles, and organizations have characterized this and categorized it. Actually, Koulenferri have done Very nice job with this. And it's a bit like a Swiss Army knife, and you've got a number of these different styles, and you use them according to the situation. So on one extreme, there's a particular style known as directive. It used to be called coercive. You probably can figure what that means. That is a style where instructions are given, and you expect immediate compliance. And there's situations where there are sometimes situations, I'll tell you what, there's an extreme example. You don't see in the heat of battle, you don't see commanding officers do a great deal of coaching. They would give orders and expect them, people to be compliant. And we don't have exactly that situation, but there are times when we need to be directive. It may be, I don't know, a few minutes before the end of quarter. It may be that the person we're coaching is new to the role and it's better that we tell them something or show them, even better, show them something. So they can learn it, and next time we expect them to do it. But that's on one extreme, and often that is overused. It's an overused style. Sometimes it's appropriate, but it's overused. On the other extreme is a coaching style. Whenever possible, leaders should be using a coaching style because research has shown this is far more effective where they can develop people. So the other extreme, and sure, there's situations where it's not appropriate, but many situations, Where it is appropriate. So that's one part. And then the second part, if you think about coaching, so how does a leader coach? There needs to be some sort of framework to do that, some sort of model. It's not just having a conversation. The model I most frequently go back to is the GROW model. I don't know if you're familiar with the GROW model. So maybe, okay.

It does.

We, Supriya, let's do a bit of coaching. You're in a sales situation. You have an opportunity and the G part is goals. So I would ask you, what are your goals? And maybe that's the goals for the session we have, but it's also goals for the particular opportunity. And you would say to me, I want to maximize the revenue. I want to have it in. I want to close it by a certain time. No problem. I get that. So we're clear on the goals. Number 1. R is reality. I'd ask you, where are we at the moment? Where do you see it? And by the way, my view of reality as a coach and yours as a coachee may be different, in which case we need to have a discussion about it. But you would tell me, and typically in sales, a good way of doing it, there are these criteria that they used to be target account selling TAS criteria, things like compelling reason to act, like the, do we understand the buying process? Do we understand who the business owner, those sorts of things? So we get a fix on where we are. Number one. So number two, that's reality rather. And then we've got to navigate from reality to the goal. And O is options. What are the options? And you and I would co-create the options, but I would ask you to identify what those options are, what the actions are. I might throw in a few, but I can't impose those. Those are going to come from you. And maybe for every 2 or 3 that you throw in, I might throw one in to keep things going, especially if you're stalled. But then we've got options. And then from those, you need to pick. We need to choose the action or the actions you're going to own and deliver on. And that's the W, it's will. So those are the actions. Once that's done, identified, it's a really good model. We can come back to it. We can assess progress. It's a benchmark against which we can assess progress. It ensures that expectations are managed effectively. It holds people accountable. Actually, it's a model for you to hold yourself accountable.

That sounds fantastic. I'm just thinking of you saying this, and I'm thinking from my very first sales job at the start of the year, taking a look at your territory and what your plan is, and what the reality of the accounts are. One of those biggest shocks you get into, here's what's expected from me. And here's actually what's available to me. And figuring the options out, especially with what the pipeline build needs to be. And do I have the will to actually go out and do that? I think that's fantastic. I love it. How would you say that a manager cultivates these leadership skills? Does he go to courses, read books, find mentors, find another manager? What's the best way to start sharpening that sword?

And that question The answer to that question is absolutely, it depends. It depends on the learning style of the individual. Now, I'm a person who would take it in from a number of different sources, and there's so many sources that you can take it in from. There's so many things, but I would certainly try a number of different ways and make sure, you're absolutely right, it's sharpening the sword. You keep it going, you keep it going, and then you utilize it. And you get feedback. And I'm not an impartial observer when it comes to coaching and mentoring because a coach or a mentor can hold up a mirror. And sometimes we're so close to the action, we can't see things. So having someone who can actually hold up a mirror and show you what's happening and has another set of eyes to help you because that will help you focus on what you need to learn.

Yeah. And I think that just like you mentioned, Mark, in the beginning, you need different people along the journey to help you to go from A to B to C, D to E. And some sources of learning can go into many seasons, and others are for specific hits. Because the way I see it, any investment into personal development, leadership development is a gift that keeps on giving. Yeah. Because you can only get better. You can't go— you're less likely to go backwards. And everything that you do, even whether you are in the work context, whether you're a sales leader or an account executive, or you're working with cross-functional teams with people who have different goals and different agendas, and you're trying to pull people along in a direction. So I think that it's just an invaluable Skill. So, we were talking about leadership development as a gift that keeps on giving. So, the question that I have next was, how does someone overcome some of the common challenges or pitfalls that you've observed in individuals trying to transition from individual roles to management roles, from the I'm responsible for myself to I'm responsible for a team? What are some of the challenges people might face?

Yeah, look, a couple of the challenges that I've seen, I've mentioned a couple previously about they need to get clear in their mind that they don't need to have all the answers is one thing. When we spoke about the GROW model, it shouldn't be that the leader is suggesting things all the time. It's got to be the understanding that the coachee just works it out. You create an environment where they can develop. Look, the other thing that I've seen is a bit of a stumbling block or a pitfall. There's this thing around humans tend to have a bit of a negativity bias, okay? They're attuned to threats. And that was absolutely, that's some of the psychology. And that was It's a good thing as well, because we wouldn't exist otherwise. Many generations ago, that was a good thing. That's why we survived. Now, in the current day, it manifests itself in different ways. And one of them that we see is managers and leaders have a disproportionate amount of time focusing on people's weaknesses, the things that people don't do as well. And it's a natural thing. Sometimes it— this is a natural thing. And I remember from my past, I remember having annual reviews where we would have 80% of the conversation was on the 20% I wasn't any good at. And that 20% was a weakness. It was something that I was never going to be fantastically good at. It was something I didn't enjoy. And the problem is this disproportionate amount of time focusing on people's weaknesses is counterproductive because it normally is something that people don't like, don't have an inherent talent around. And if you focus on it, the best they're ever going to be is mediocre in that area. And you don't want to build a team of mediocre all-rounders. You want to focus on people's strengths. And it's depleting, it depletes energy focusing on those things. It's much better, it's much more effective working on people's strengths, identifying strengths and working on strengths. And there's research that shows people who work on their strengths, organizations who focus on the strengths of their individuals, The people there are 6, the employees there are 6 times more engaged. And I see this also with smaller organizations, smaller companies, how it's just so important to work on these. And when they get it right, that the people in these particular roles do their best work. And when you've got a limited number of people, it's just even more important. They do their best work at work, the best representation of the companies they work for. And I've worked with some founders. It's very interesting. I've coached some founders and there's a couple in particular, incredible evangelists, brilliant futuristic visionaries. And this comes from the assessments that have been done of them and excellent communication. But there's a couple I know, not so good at execution following through, but that doesn't matter. Let's play them to the strengths. We can find strategies for dealing with that other part. Okay. And this is where they're most energetic. I do remember MuleSoft, you mentioned that we started with 8 people and we grew rapidly. And I always remember the hiring philosophy of MuleSoft was get the right people on the bus. And once you've got the right people on the bus, talented individuals with the right attitude and so on, we can do a little bit of molding for the types of roles so they can play to their strengths. And that's what I feel we were able to do. We grew rapidly. It was, you know, the numbers speak for themselves. I think it was 66% compound annual growth. Wow. Over a long period of time. And a lot of that was having people play to their strengths.

That's fantastic. Jonathan, thank you so much. We've whizzed past the little time that we've had together, but I've learned so much today and I'm sure that this episode is going to be really useful to so many people who are at different stages of their journey as leaders. Thank you again. And anyone who has listened to Jonathan, I encourage you to reach out to him on LinkedIn. And I'm sure you'll find yourself just going from strength to strength as you find a great coach. So thank you.

Thanks a lot, Pri. It's been a pleasure. Thank you.