The Hidden Power of Mentorship in Sales Leadership

Welcome to The Switchkey Show. This is your host, Priy Saka, and today I'm joined by Andrea Breen. Now, Andrea is a well-respected leader in the software industry. She is best known for building successful teams and coaching people to achieve their potential. She has had a terrific career with companies like Oracle, Pitney Bowes, and is currently the VP of Sales and Customer Success at Objective Corporation. Andrea, Welcome to this conversation.

Thanks so much. It's great to be here, Pri.

Fantastic. Now, Andrea, I know that you have a passion for coaching and mentoring, which is why I really wanted to have you on this conversation and really get into that. So to kick us off, tell me, what is the difference between coaching and mentoring?

I think one key difference that I see is there's no measuring of performance when you're mentoring. So, you're not there to measure performance. That's the role of the manager. And I expect that mentee to drive the relationship more. So, I expect them to really be the driver of making sure that there's regular catch-ups and meetings. And you can personalize a program, or you need to personalize a program for a mentoring sort of scenario. On the coaching side, I think the coach really is driving the relationship. And there's lots of measurement of performance along the way.

Mm-hmm.

So, there's check-ins along the way. And some of that coaching can be standardized. If you're running a whole sales team, there'll be certain elements, each of that, that team that is quite standard. So there is some quite different elements. But I think the key that links them both together is that the coach or mentor needs to be a really good listener.

Oh, that's really good. Yeah, that's very good. Thank you. So the coach needs to be a really good listener. In the case of mentoring, the mentee needs to drive the relationship, but there is no performance management. With Coaching, it's the coach who's driving the relationship typically. And there is a specific outcome and checks and measures along the way. Thank you. That is excellent. Thank you very much. Tell me, can a hiring manager be a good mentor as well as a coach?

I think they can be. If I look at the journey I've been on, I think that is possible. But I think in that scenario, the mentor needs to be quite senior. Because they need to be able to delineate between when they're in mentoring mode and when they're in coaching mode. And they do have to do both with that individual. So I certainly have had that situation where I've had an amazing leader who was coaching me as well as mentoring me. So I think it's possible, but they need to be senior.

Yeah. And I would also imagine that coaching is very likely to be specific to the role that you perform, whereas mentoring can be broadly about other things like personal development, relationships, whatever. The mentee is setting the guardrails of that relationship and conv— you know, I think the mentee defines the scope.

Absolutely. And defining the scope in that relationship is really important, I think, for the outcomes to be delivered that both parties need. So it's not all about the mentee. I, as a mentor, I get lots of satisfaction about performing that role. And I like to make sure I put the time in to make sure that we're both getting the outcomes that we need out of that relationship.

That's really good. And I think that I just wonder with remote working and hybrid working, and flexibility is a critical component of work-life balance. But I wonder if we are missing out the potential for unstructured conversations, relationships outside the straight lines, the dotted lines relationships, especially with people who are earlier in the workforce but find themselves at home. How do you end up finding good mentors in that process?

Look, I think that the organization you work for really does have a part to play in that and doing that matching. So, through that professional development cycle and check-ins and performance reviews and so forth, certainly the organization I'm at, Objective, we're really about trying to make those matches where possible. And I think for me, I've got a great relationship with other senior managers in the business. And often one of them will come to me and say, I've got someone in my team who I think would really benefit from you being a mentor. And so that's how we, we do that. In saying that, I've been in the business I'm in for almost 7 years. So I have a great network. I think it would be tougher in an organization that wasn't proactive where you were quite new. So it's something to think about there. Remote working does make it a bit tougher, I would have thought, to build those relationships.

Yeah, no, that's— and I really like what you just said about a manager actually identifying someone on their team that will benefit from a mentoring relationship, someone who's at their peer level, and initiating that. That's phenomenal. Because sometimes I think people early in their career don't know what they don't know, right?

Well, they don't know. And I think on that front, early in their career, and I certainly learned a little bit about along the way, when I was asked to mentor someone, is that it can be a little bit of a scary process for someone early in their career. So if they've been matched up with someone who's in a senior leadership role, I know when I first started mentoring, one of my first questions was, what's your goal here? Do you want to move forward in the business to higher roles and promoted roles, or do you just want to be the absolute best you can be in the role you have now? Now that actually really scared that person because it made them really think about what they needed to do.

Hmm.

So I've needed to soften the approach in the early stages, I think, and learning from that because That mentee decided not to move forward because I was too challenging in my approach.

Yeah, OK, I can see that. And I think that also, you've got to match the— based on the mentee's motivation and their readiness in their cycle, match them with somebody who's going to be able to be a great mentor.

Absolutely. It is all about the match, all about the match. Because I find if there's not a good match, the mentee will not be authentic and open up in the process. And that's what's really important.

I remember hearing this somewhere, I can't remember where, but it says that when the student is ready, the teacher will appear, right?

That is right. And I think in that earlier example, I think that was one where a manager had recognized somebody. And I just don't— I felt like they needed to do a little bit more soul searching and thinking about what they wanted to achieve and get out of it. I'd love to circle back now, but I think That ship might have sailed. Yeah.

On a side note, as a parent of teenagers who won't listen to me, I say the same thing. When the student is ready, the teacher will appear.

That's right. Geez, I'll have to remind myself of that for my children.

All right. Let's, in terms of on the mentoring side, I will come back to coaching for a moment. But on the mentoring side, I think that you've pointed out a couple of really good things in terms of organizations have either a reactive— because you get all sizes, small, medium, large, very large organizations. In some organizations, it's very structured, and there is an intent, whereas the others, that doesn't necessarily exist. And often with tech companies with offices in Asia-Pac, I can tell you, often that is not the case. It's very much a sales outfit. And the concept of mentoring may not exist. So what are some of the things that leaders can do to create an environment that is conducive for mentoring in their organization?

So I think the first thing is you need to be open to being a mentor. So I know that there's a line in a song that I always think of that says, don't forget where you get— when you get where you're going, don't forget to turn around and help the next one in line. And so for me, if I look at the journey I've been on in my career, there's been a number of people that have mentored me either formally or informally along the way. You don't get to where you are in senior leadership without other people helping you along the way.

Mm-hmm.

And I think that more of our leaders need to commit the time and their energy into really fostering the talent in our organizations because they are the key to the future. And without that, I think it's a problem. There's lots of senior leaders out there who do no mentoring, and I think it's a problem.

Well said. Well said. You know, I see people— one of the taglines of this show is Survival, Success, Significance. And it seems to be the cycle of one's career journey. You're either in survival mode, early-stage mode, or you have unexpected change thrust upon you. You then get to a place of success. But I know a lot of people who are successful and still feel like something is missing, because that significant component often is only achieved when you do something for someone else. It's not for yourself.

It is so true. And I think it's very easy in a senior role to say that you're busy, but it's about carving out the time. And like I said early in our discussion, I get as much out of mentoring as the mentee does, always. And so I don't see it as a burden. I see it as a two-way engagement where I can learn. I'm a lifelong learner and I think everyone needs to be. You never stop learning. And I often think in my team, I'm mentoring someone who's much earlier in their career at the moment. But he's very dynamic and very driven. And I've learned a lot from that person because they think differently to the generation that I'm in. And I think they, they want different things and they have a very different focus. So I use that when I've got different people in my team that have different dynamics.

Yeah, no, that's really good. To recap from a mentoring point of view, I think that companies need to create an environment where The managers are willing to share some of their time. And the mentees know that it is OK to actually reach out to someone and ask them to be a mentor.

Absolutely. Look, I know at Objective, our Head of People and Culture gets on that first meeting between the mentor and the mentee. There's a framework that's set out and taken through so that we can do some goal setting. And so they really do match you up and set you on the path for success moving forward.

Yeah, that's fantastic. All right. Let's move on to coaching. And from a coaching point of view, I'd love to get your thoughts on maybe how do you take— there are 2 scenarios that you typically get into. You've got people who— actually, let's take it one at a time. The first scenario is somebody who is in their first 3 months. And you want to set them up for success in that year, because that year will really define maybe the next few years, because depending on how they perform in that first year will depend whether they remain there or not. So from a coaching journey point of view, what, what does that typically look like? And do you have a framework that you use?

So I do have a framework. And I think there's a few components. So I've actually just had some new starters start with me in the last month. So it's very topical at the moment. I think the first 3 months is really critical. And it's not just about the onboarding of, this is how the systems work and these are the solutions and this is the team. It's about understanding from them where they're at, where, what they're bringing to the table. I always say to them in the first week, what's your observations? You've come in with fresh eyes. I'm learning as much about, from them as they are learning from me. I think regular check-ins with them. But I also don't like to spoon-feed. I like people to have the initiative. If I can give them the tools that they need, the resources, the people, I expect them to show the initiative to go out and get what they need. So, it's the 3— the first 3 months is very important, though.

I understand that. Tell me a little bit more about the framework. What does a good coaching framework look like, or what has worked for you?

So I think for me, obviously someone who's new, there's onboarding and so forth, but then you get into a regular cadence. I hear from some leaders, they don't necessarily meet their people once a week. So I've always run a structured one-on-one every week where I run a sales team and a customer success team. But I say to them, this is not a forecast call. Our one-on-one is not a forecast call. That's later in the week. This is about what blockages you have in the business. What's driving you, what the career aspirations are, and what the path looks like. Because it's a bit frightening, but I have come across people that have joined the company I'm at now that have never had a conversation about what their career looks like with their managers in the past. So, whilst I take it for granted because it's the formula I always use, it's not widely done out there, which is a little bit scary.

Hmm.

For me, I want to give them an opportunity to raise concerns. I always encourage, if something's going great for you and you're working amazing with someone, what's that too? Let's celebrate the small successes along the way as well. But it's a very structured— I take notes in that meeting every week. I follow up with them. And I can always sense— you can sense when someone is— there's something going on with someone generally, where I'll generally say, I can tell something's going on. I don't need to know because everyone has challenges outside of work. But if there's something going on, just let me know because then I can kind of sense where you're at. And 9 times out of 10, there's something going on.

Yeah. So that's— and you have to be intuitive and listening to be able to pick up on that, right?

Yes.

Tell me, in terms of staying on the one-on-one and the coaching topic, What are some of the mistakes in either thinking or mistakes and actions that hiring managers make, or you've made, or you've seen others make in a coaching relationship, which makes that from a neutral conversation to a stressful conversation?

Probably some of the mistakes are when you've got someone in the team that you are sensing is an underperformer or is underperforming. That you try and compensate for them. So I think earlier in my career, you can very easily, as a leader, get caught up in doing their job for them to cover them, which never ends well. They end up annoyed and the job is their job to do. It's not yours to do. I think that tends to be because then they feel like they're being micromanaged. They feel like they're not being given the tools and the space to do the role that they've got to do. That would be the first one that I've noticed. As far as that goes. And look, the other side probably is, I think you can be one of two ways in. You like to think when someone joins your team that they've got 100% of your support and that they will go and do the role that's required. But I think probably as I've got further in my career, I've realized they need to earn some of those gates along the way. So it's been a bit of a change as time's gone on.

Yeah, no, that's really good. One of the things that you mentioned around overcompensating for people or doing their jobs for them, I got into that trap when I was a sales manager, an early sales manager at the Fortune 100. And I had a team of 7 people at the time. And I remember, I would often do things which the person should be doing for them. And my, I was doing 12-hour days. And I came across, accidentally, this old but gold book called One Minute Manager Meets the Monkey by Ken Blanchard. And it really, it's a small little book like Who Moved My Cheese? But basically— It talks about how managers who take on from their team are really like monkeys. It's their problem, but it's sitting on your shoulder. And it's the rep who leaves, and the manager's still sitting in there, the busy— they're busy. And at the end of the day, the rep doesn't learn anything because you are basically doing their job. Whereas you actually help them solve the problem and action it themselves. And so that was really useful back, back in the day. So anyway, tell me in terms of from a From an— from a sales rep's point of view, what are some of the mistakes they make in a coaching environment with their manager? Let's say the second situation, you've missed quota for 1, maybe 2 quarters. Your activity may not be where it's supposed to be. Maybe you are chasing this big whale, which never eventuated. How many times have we heard that? What are some of the mistakes that they make in that 2— in that one-on-one scenario?

So I think the first one is that they come with the problem. That's amazing. Humans are really great at pointing out what the problem is. That's the easy part. So I always say, that's great, we've covered the problem. Now, what is the intended solution here? At its heart, sales is about problem solving. So I think for me, I struggle with the team when they don't come with the solution. I'll always say, state the problem, this is what— and what you're doing about it. The other thing, I think the second thing is they'll come and say, Andrea, how are we going to fix this? And then I always say, how are you going to fix this? Because you're trying to make your problem my problem. So they need to come with some initiative on solutions. And I'm okay if they come and I go, no, I don't think that's the right path. At least they've given it a go to work forward. And look, the third thing for me, and probably the biggest one, to be honest, is when they're not organized. I think that there's a misconception in our industry, in sales, in tech, that the people who are in sales, they're never great at admin and they're not very organized. And I just don't accept that. Tech is very well paid and people need to come to their one-on-ones and their forecast calls and be super prepared. So for me, I think sloppy in a manager's meeting or a forecast call, I always think, what are they like in front of the customers?

Yes. Yes. And look, you've just said a little while back that you take notes. So, it really means that you're placing so much value on everything that they are saying. You've got— there's also a responsibility on their part to be professional and organized and ready for that value, that time that they're getting with you.

Yes, I have. I'm a prolific note-taker. I have notes from every meeting I've had in the last 7 years I've been in IT.

Seriously?

Yes. Oh, wow.

That is amazing.

With every client and every one-on-one.

Wow. That is so amazing.

So, I think the beauty of taking notes is I run quite a large team is that I can get back a week later and I'll say, this is what we discussed and these were the actions. So, there's no hiding is the other thing. They don't say, oh, she's forgotten about that, because I never forget because it's written down.

Oh, that's good. That's very good. Tell me about situations when in a coaching conversation you believe Or you start feeling that you're not getting either the whole picture or you are being misled?

Yes, it's not uncommon. But I think you've got to have a very good radar as a sales leader, I call it, a very good radar. And I will keep probing and I won't let go. And then if I feel like we're still not getting anywhere in that call, I'll say, I'm happy to leave it here. I'm going to book 15 minutes with you tomorrow to cover this off. I find then the passage of time can allow a fresh approach and then to really think about things. But generally, there's always a need behind the need. I always got taught early in the piece of my career, and all is not what it seems sometimes in sales and the deals that are on the table.

Yeah. And that is so good because I think that at the end of the day, we are all depending on information that is passed on through someone else's filter, right? And you're making decisions based on that. I recently had a conversation with Chris Wood, who leads Quest in APJ, and he was talking about using medic, medpic, and really creating a culture of transparency, where transparency is critical. It doesn't matter if you don't know, say so, and go and find out. But transparency becomes, makes everything easier for all teams involved. So.

That is so very true. And, but it is, you made, you made a very good point there. It's OK not to not know. And I'll say to the team, who, who's going to sign off on this? I'm not sure yet. Okay. So that's one piece of information that you need to go and find. So I think that's important, but just treading water and covering and trying to make out all the answers, that becomes fairly transparent fairly quickly because I think the sales process, there are unknowns. If it was that straightforward that people would just get online and buy what they needed to buy and move on with a credit card. And that's not the enterprise software world.

Yeah, yeah, very good. So, changing gears now, I also know that you are a huge supporter of women in technology and the gender diversity, and I'm a huge fan. Tell me a little bit more about what you've seen in the industry. You've been in the industry for a long time.

Why is it important to you, and what are some of the things that you So, I think for me, I've had and continue to have an amazing career in this industry, and we're still very underrepresented, I would say. So, I think for me, first thing is, from a talent pool, the industry is missing out because there's a lot of amazing women out there that would be in tech who are not. So, that's the first thing. The second thing that I've probably noticed on the journey is there's some amazing organizations now that are really championing this cause. cause. One in particular that I'm involved in is Women in ICT, started in ACT. There's a lot of dedicated people in that. It has a great following. I've spoken— I've been a speaker at one of their breakfast events. And so for me, having someone like that who advocates for change in the industry, my advice to both men, women, otherwise out there is support those organizations. Be a member, go to their events and support them because they are championing your cause on your behalf. Would be the first thing. The other thing is, and I'm trying to get this happening, is to use inclusive language. I don't know how many calls I've been in, and I'm quite often me and 7 males in a meeting, which I'm very used to, but I'm very cognizant of people saying, thanks guys, how are you all guys? And so I've checked a few people in our organization and said, can we just try and use a bit more inclusive language? There's not much that offends me in life, just to be clear.

Right.

But I just think we need to make sure that we do that. Along the way, celebrate the success of women in your organization too. When your women do a great job, then support them, promote them, get them into leadership. Because a diverse organization is a better organization. I don't need to tell anyone that; the stats show it.

Yes, and I think that, that's absolutely, that's framework 3, right? A diverse organization is a great organization. I think that Increasingly, and I see what you say, that companies are becoming more and more aware that there is a gap on, in a number of different ways, and that the gap needs to be bridged. As an executive recruiter, I get asked, 7 or 8 out of 10 searches, I get asked diversity searches, right? We would really like more of women in the team. We are completely underrepresented. And I said, one of the things as a headhunter that I get told is to go and find people in the competitive space, right? And I say, you've got to be open to people who are outside the competitive space than your immediate ecosystem if you really want to improve the diversity. Because even at an 18% women to 82% men, you're again looking at an And anecdotally, as a— this is just, I'm going to say it, that men, 2 out of 3 men will say yes to an opportunity because it looks good. But for women, it needs to be a much higher match because they have other circumstances that they need to consider before making the jump. So when you put 2 and 2, far more considered in making moves, and as well as a smaller talent pool, you really need to be very inclusive right from the hiring criteria. You can't limit it to, well, they've got to have solved cybersecurity. to X and Y bank— not going to happen— to be able to really discover some amazing talent. So that's my 2 cents on it. But I think that we're in a much better place than we were 5 years back.

Moving— I don't feel like we're moving fast enough is the challenge. And I think, for such a dynamic industry that has such amazing career paths in it, I look back, and someone only asked me this a couple of days ago, The question was framed around, do you really need to be quite tough to be in this industry and a little bit hard? And I went, at times I've needed to be that way to get where I need to go. And maybe that's because we're out of balance.

Yeah.

So interestingly, one of my mentees, one of her goals, which frightened me a little, back to the mentoring side that loops in here, is that she said to me, I need to learn to control my emotions. all the time while I'm at work. And I said, why? I said, if you're happy, be happy and tell them why you're happy. And if you're sad, be sad. And I think that comes from a bit of gender bias coming in. And she was a bit shocked when I said that. And I said, the only reason that the rest of your team are a little bit confronted when you get a bit upset about something is because they're not used to it, because you're the only female in their team. So I said to her, be yourself. Be authentic, harness emotion for good, but be authentic. And so, I often think, are women not in tech because they see it as a, as that you've got to be quite hard and quite tough to get where you need to go? And I don't feel that's the case. But I think there is a perception in the industry that that is the case.

I really like what you said in the beginning about when you have, when you have gotten where you are going, you know, you need to turn back and take more people along with you. And I think that there's, there's a real need to have women leaders step up and actually speak more across organizations to allow that next generation and the generation after that to come up, right? I think that is critical. I see some organizations doing a great job with intake programs right at SDR levels.

Wow!

I think Salesforce has done really well. I've seen DocuSign and a couple of other companies do really well. But at the other, they're just some, a few large employers. It's not the case necessarily. But I think we need more leaders speaking out.

There's more happening out there. And it's not just gender diversity. We need diversity across a number of categories and to be a very inclusive workspace. I'm very fortunate at Objective that we have an absolutely dedicated program. We are committed to moving forward on that. So I feel fortunate that I'm part of the wave of change that's sweeping through now.

That's really good. Look, I cannot thank you enough, Andrea. This has been a fantastic conversation. It's— you've shot straight from the hip.

That'd be unlike me.

You know, I've learned so much, and I'm sure there are others who are going to learn so much from this conversation. So thank you. Thank you again.

Thanks so much, Pari. It's been great to speak with you.