EPISODE 348: Oracle Public Sector Sales Leader Tamara Greenspan Gives Advice on How to Enroll the Perfect Mentor

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[EDITOR’S NOTE: This is a replay of the Women in Sales Webinar sponsored by the Institute for Excellence in Sales on March 31, 2021. It featured Tamara Greenspan, Group Vice President & General Manager, Federal & Canadian Public Sector, North America Applications at Oracle.]

Register for the May 7 IES Women in Sales Leadership Forum here.

Find Tamara on LinkedIn here.

TAMARA’S TIP FOR EMERGING SALES LEADERS: “Don’t be afraid to ask someone to mentor or sponsor you. Don’t be afraid to put yourself out there, don’t be afraid to let people know that you need help. A lot of times people are just afraid to ask so just be organized, document and think about what you need and then ask. Have a specific reason you are looking for them to help because you might be going to the wrong person or they might not have the perfect skill set that you’re looking for. You could also consider multiple people.”

Gina Stracuzzi: Tamara Greenspan is going to be talking to us about the very important topic of mentors and sponsors. It’s always a pleasure to talk to you and this is one of the things that you hit on in the forum, is the subject of how important having mentors and sponsors is to really elevating your career to the highest level possible. Why don’t you talk to us a little bit about what mentors and sponsors are and what the difference is?

Tamara Greenspan: Sometimes people think they’re the same thing or they don’t really understand the difference, but there’s definitely a difference and a value to both. Before I talk about the differences, not everybody has both, some people have one, some people have none. When we talk to the other women in the forum, you find that there’s all different variations of people either having some or looking for some. So very important that we work to define the differences so you can actually set your goals and try to get where you need to be with that.

The main difference, to summarize, is sponsors actually pull you along in your career. When you’re in your company – and we’ll talk a little bit about where to find mentors and sponsors outside your company – those are the individuals that have actually seen your work quality, have maybe worked with you on projects.

They aren’t necessarily in your direct reporting line, but they are usually people in higher level positions that you’ve engaged with. So they understand your abilities and see that you’ve got potential. Those individuals will pull you along, they’ll pull you up, they’ll recommend you for positions, they’ll recommend you if they leave the company, pull you there as well.

Mentorship is different, mentorship are any type of a person that you can ask a question, whether it’s a work situation, whether it’s a career situation. It could be situational for that specific engagement you’re on or it can be more general about how you’re approaching your teammates. That’s a different role and they’re both very valuable roles.

When I look at my career – I’ve been in Oracle for 31 years, I’m going to be working on my 32nd year in October – it evolves and it changes. Mentors really do change, you might have some similar mentors and you might keep them throughout your career but they change and I actually recommend that you evolve and you add mentors.

I’m not saying that you should leave a mentor, but as your career progresses, you’ll need some different advice and different situational experience from somebody so those mentors should evolve along your career. A sponsor, they’re probably going to stay with you even if they’re in your company or out because they really understand your abilities and they will pull you to your next career aspirations.

Gina Stracuzzi: When I first started listening to you talk about these, I didn’t appreciate the difference myself because as I mentioned, there weren’t these options for women coming up when I was at the heart of my career growth. It’s fascinating to me especially with the mentors, the varying roles that they can play like sounding board and basic advice on how to get really strong at something helping you to see maybe where you might have a blind spot or some shortcomings.

Can you talk to us a little bit about the kinds of conversations you’ve had with your mentors? Do’s and don’ts maybe a little bit.

Tamara Greenspan: I don’t think there’s any do’s or don’ts because a mentor is there for you and is there to support you. If you have any situation, again, it can be anything from how to approach a situation, even a sales situation. You have a complex sales engagement with different parties, maybe some customer issues, maybe some internal issues, you have to rally a whole group together and you might have a mentor that has experience in that.

You might engage in that situation or you could engage your mentor if you’re having a problem getting along with your manager, you’re in a new management situation or one of your coworkers. Or you also could engage them if you’re in a type of a team environment and this person maybe has experience in getting the best value out of a team to meet a common goal.

It can be anything and it also can be personal. A lot of folks have mentors, and they might throw in some personal, like with women it could be some personal balance, family time, how do you do it? How did you have a baby? How did you keep your career moving? It can be all types of questions.

I personally don’t feel that there’s a do and a do-not because I think that person is there to help you with anything you want. That’s why I encourage people to get different mentors along your career path, because as you change, you might be looking for somebody with a little bit of different experiences or they might have chosen a different path.

No path in any of our careers is right or wrong because it’s a personal decision. Whether we decide when the best time is to take on more responsibility or maybe we want to take a lateral within our company or move out our company. There’s no right or wrong decisions, you just have to determine what’s the best decision for you at the time both personally and professionally.

I do think you really need to constantly add and there’s a lot of places to get these mentors. I’m going to talk about that because it’s really important to both look for mentors inside your company and outside your company. Because sometimes you just have a situation that would not be appropriate to run by someone within your company, you’ll feel more comfortable outside.

We all have the friend group and we all probably got friends in our same industries but it still might not be appropriate to run by a friend, it might be better to run by an independent person who maybe is not as connected to you. I really encourage people to join associations in their industry.  Associations are great places to both meet customers – especially for us in sales – but also to meet other individuals who have common experiences and frustrations and successes that we share. Some of those folks can be very important mentors in your life.

Also, they actually could end up being sponsors as well. When you work in some of these associations, I know it’s volunteer but you’re actually doing very important customer-facing type situations. So those counterparts get to know you and get to see that you’re committed, you can deliver, maybe you have contacts, maybe you know the subject matter expert.

Those individuals are also at management positions in other companies, they actually can see your capabilities and they can end up being a sponsor for you. I do think it’s very important to look at your entire life because, to be honest, I’ve found some valuable mentors on my kid’s soccer field. Their parents could be in our industry too and you could actually find that they are in a same customer base or the same overall industry. All these connections can really help when you need help.

Gina Stracuzzi: We have a question. Anita would like to know, one, if there’s still a lot of mentoring going on in this virtual world and two, how you can look in groups in the virtual environment. I’m assuming what she means is if you’re not part of a group right now, are they still doing a lot of things that you can join in a virtual way? I can imagine it might be a little awkward trying to find a mentor in a virtual environment that you’ve never been in before, you’re just going in as a new memberof a group or whatever. Do you have any advice along those lines?

Tamara Greenspan: Yes. There’s a lot of mentoring programs right now. There’s formal mentoring programs and there’s informal mentoring programs. If you happen to be with a company that has a formal mentoring program, like we have one at my company where I register to be a mentor and then I put some of my role, some of my history. Then mentees can actually come in and say they want a mentor and we can be matched. That is a formal program.

There’s a lot of formal programs occurring now at companies because companies are working very hard to try to connect their employees in this virtual environment. There’s also informal where you will find somebody that maybe you feel could be beneficial or they might be in an area that you want to investigate where you ask them, “Can we have virtual coffee? Can we just get on a Zoom?”

I can tell you, almost every single person who’s asked me to do that – because I do both formal and informal, I will always meet with people – people will almost always meet with you if you actually ask. You can definitely do that as well, it’s just I think sometimes people feel that everybody’s busy. And yes, everybody is busy but there’s a lot of people that want to pay it forward.

People like myself, I’ve had a lot of wonderful mentors and actually two that I would consider sponsors in my career. I still am connected and feel like I can always go to them and they don’t all work at my company. For the group question, yes, because everybody’s figuring out how to work in the virtual world and all these associations and different groups are still engaging, it’s just different.

When you say you’ll sign a group that might be of interest to you, I do recommend a group or an association that does evolve your career area because you’ll have all that in common with people. When you get involved and tell them you want to get involved, then you’ll break into subgroups or smaller groups and then you can engage with people and get to know them that way. I’m assuming we’re going to get back to both a combination eventually of virtual.

Gina Stracuzzi: This might be a really fabulous time for us to say that one of the things that the brand new Women in Sales advisory board is going to be doing is putting together a formal mentoring program just for women in sales. That’ll be forthcoming in very short order and I’m super excited about that. There’ll be opportunities for people to be mentored and opportunities for you to be a mentee as well.

That brings me to some questions that are popping up now. Beth would like to know how she can be a great mentee.

Tamara Greenspan: That’s a great question. I think to be a great mentee you have to be honest, especially if you’re just creating this relationship because if you’re creating a brand new mentor to mentee relationship, the mentor wants to know what’s the goal, how you need help and how’s the best way that you want to engage.

A lot of times mentees say I’d like to have a coffee or virtual Zoom once a month some are every quarter, some are just as situations happen. I think as a good mentee you need to think about that and approach the mentor because the mentor, you don’t know how many mentees that mentor has, you don’t understand the time commitment. You want to get a mentor that will meet your needs so come forward with that information so you can set the expectations properly.

Gina Stracuzzi: That raises a good point, that if you’re asking to be mentored you should know what it is you’re trying to achieve is what I’m hearing from you. Just to say, “I want to make sure my career’s really good.” Would you recommend outlining particular goals that you’re trying to achieve?

Tamara Greenspan: Yes, definitely. Again, I would focus on if you’re a mentee, what’s your goal and the purpose of having a mentor? Is it situational? Is it situations at work? Is it maybe having issues figuring out the best way to approach something or is it purely career-related? Or it can be a combination of both, because then you have to make sure you’re getting the right person who can help you with that, because that’s why you might need more than one.

One person might not be the best for all of those areas and I encourage a mentee, after you get engaged with a mentor, it might make more sense. You’ll see that maybe you need somebody that’s more focused on your career and it could be a one, three and five-year plan, it could be a three to five-year plan. But you need to outline what you’re looking for and then that mentor basically can give you advice.

It might be the perfect person for maybe the one-year plan but maybe you need to look for a different type of mentor with a different career path for the three to five year. It will evolve, but to get started you really have to know what you’re asking for to make sure it’s a good match.

Gina Stracuzzi: Frederique would like to know what your thoughts are about socializing with mentors. Should you keep it all business?

Tamara Greenspan: If you work with colleagues and you get to know people well, I think it’s a balance. I think you have a friendship and you have a business relationship and I think it’s okay as long as you’re getting what you need. You’re getting honest feedback and not feedback that maybe is the feedback you want to hear.

That’s maybe where the blurred line between a friend and a business colleague cannot result in the help you actually need. I think it’s fine, but I think you have to have the right mentor to make sure that they’re not, “I don’t want to say this because I don’t want to hurt their feelings” or, “I don’t want to say maybe they’re being too aggressive in this situation because they’re my friend.”

I think you need to evaluate that to make sure your mentor is comfortable with being honest, because if you’re not getting honest feedback, it’s no value.

Gina Stracuzzi: To your point earlier that mentors, it doesn’t work if they’re your friends because as you say, they’re not always going to be honest with you. But also, their responses are colored by their desire to protect Tamara, “Yeah, that’s an awful thing that’s happening to you at work and this is what you need to do.” I’m that kind of person that I want to go in and fight that fight for them.

That’s not helpful and that’s what happens because you are going to have mentors and mentees that you just click and you have a lot of things in common. And the line starts to get blurred which is okay, as you say, but then you have to weigh the advice you’re getting from that point forward.

Tamara Greenspan: Right, and if you think about it, especially if you’re having mentor for career advice, that mentor needs to understand your family dynamic, what your goals are, what the timing is. All of that for working women are huge factors and decisions on career moves, they just are.

Gina Stracuzzi: Would you recommend then that you give a deep dive to potential mentors once you’ve decided to work with them? Let them know all the things that are potentially impacting your career like family life and kids who are struggling, whatever the case is?

Tamara Greenspan: I do, I think that’s very important to put it all on the table because if you look at the mentor’s position, it’s hard to give good advice if you don’t have all the information. You have to have the whole picture.

I will tell you, I love to be a mentor and to help people as well. All my mentors and sponsors were men so I didn’t have a single woman either so I’m not even saying you have to have women, it’s individual. I just think that women were lucky today, in the focus of women helping women, you actually could get a woman who maybe had those struggles as a working mom.

I know you always laugh at me, I just say I’m a working mom of three who sells software for her career. You want to find somebody that maybe has a path that you’re interested and understand some of the decisions that you have to make.

Gina Stracuzzi: Men might not quite understand the internal battle that happens for women when it comes to family and stuff. They still have lots of great advice especially if you’re in a male-dominated industry. If you believe they are really somebody that has your back and could be a good mentor, you should really go after them. Having a mix gives you a good picture of things.

Frederique has another question, she wants to know if you’ve ever been in mastermind groups or peer growth groups and how that can help and what your experience was.

Tamara Greenspan: I personally have not been in that. My first involvement in all this was when I went through a women’s leadership academy program for a year to really understand the value, to understand the differences. I also run the Oracle Women’s Leadership with a colleague of mine in Oracle for the Reston, DC area. We bring in programs and we bring in coaches as well, this is just an internal program. I’ve actually learned a lot from that.

I probably started a little late in my life, but when we first brought up this mentor/sponsor, I think we had a session about eight or nine years ago, I had these people but I wasn’t calling them that. I think a lot of people might have some a mentor and/or sponsor but they might not be referring to them as that because they didn’t really identify that that is the person that’s looking through these things.

Gina Stracuzzi: Sometimes they’re considered champions or just coaches, people refer to them in different ways but the goal is the same, it’s to support you and your career growth. Let’s talk a little bit about the importance of mentoring other women. A lot of times women might not think of themselves as a mentor or they don’t really know how they can help, so let’s talk a little bit about that. Let’s say you want to support other women, what would you say a woman in that situation could do to help others?

Tamara Greenspan: As a mentor, I think you should look within your company and I think you should look to see if they have established a mentor program because a lot of companies, if they don’t, they’re doing it. Especially in this virtual world, it’s a great way to connect people when we’re not in a connected type environment. Or you should reach out even if you went to your leadership to say you would like to do this because you’ll ask to find the folks.

Right now in a virtual world it’s hard to find some new people, people aren’t really connecting, there’s not the office environment, there’s not these big team meetings going on. I would one, ask your companies and two, like you just said for Women in Sales. In all these associations, a lot of them have mentor programs.

I also am very involved in AFCEA, in AFCEA NOVA we have a mentor/mentee program. You can also get it from outside organizations like Women in Sales, like some of these other associations in your area. That’s where I would recommend going. They are there, ask people. Sometimes our biggest most valuable resource is just asking the people around us.

Gina Stracuzzi: Let’s take this to the level of sponsorship. Frederique had one more question which is a good one, what if you ask somebody to be your mentor and they’re not really responding or they’re vague about their interest? Do you keep asking, do you move on?

Tamara Greenspan: Move on. Listen, not everybody is going to want to take the time, I just think it’s very valuable, especially someone who’s used those resources for my career but move on. There are plenty of women and men who are willing to help but again, you have to also not generically ask them to be your mentor. You have to have a plan, make sure you ask them with some type of goal. That can evolve and it’s okay if it changes, but you want to ask them with some type of reason because they also want to make sure that they feel like they can help you. A mentor doesn’t just want to be a mentor for nothing, they want to make sure that they can help.

Gina Stracuzzi: Let’s talk a little bit about getting a sponsor which is a lot loftier. The hope is that somebody really high-level will come to you and say, “Tamara, you are amazing and I’m going to be your sponsor, I’m going to make sure you get all the visibility and notoriety that you need” but that may not be the case for most of us. How does one go about securing or getting on the radar of somebody that could be a sponsor? And how do you know if someone is going to be a good sponsor?

Tamara Greenspan: That’s a great question. Definitely, sponsors are different because you don’t just ask, you’re not going to go up to somebody and say, “Will you be my sponsor?” That’s not how it happens, it evolves and it’s mostly going to evolve with someone that you work closely with and you’ve been successful because they’re looking for successful people that they want to pull them along their career and also pull them with them maybe as they move up the company or they leave a company.

The best advice is to actually just work on whatever your career is and do a darn good job, but also make sure that you’re taking risks sometimes. What I mean by taking risks is maybe there’s a project that could give you exposure to different leadership members across your company. Raise your hand because you also will need to be a known entity because sponsors are looking for people.

A sponsor is always looking for the next person to either replace them or to replace their management team but you have to have executed and been successful. Mostly those folks are going to be people you work with for a while or people you kept in touch with when they leave. So I highly recommend if you have a great relationship with a leader within your company and you work with them closely and they know your abilities, keep in touch with them. They could pull you to another great opportunity someplace else. It’s a small industry really, in technology sales everyone knows each other.

Gina Stracuzzi: I’ve learned that very much so through the forum when people are like, “Yeah, I used to work there and I know you.” Amy would like to know, “Do mentors ever turn into sponsors?” Would you recommend that?

Tamara Greenspan: Yes, they definitely can. I would recommend anything that works for the goals that you’re trying to achieve. Your mentor is in a leadership role and they are also somebody that you’ve proven yourself to and you feel that they can pull you along in your career, that they would back you.

When I say pull you along, it’s also recommend you to somebody else. They will be the one that will put themselves out there to say, “Yes, Amy’s the person for the job, I highly recommend her, X, Y and Z, this is the experience I had.” That’s a sponsorship too, it’s not just pulling you along with them, it’s also sponsoring you for other jobs. They’ll be your advocate for that position, so that can definitely happen.

Gina Stracuzzi: If you don’t necessarily see anyone within your company that you really feel could be a good sponsor or seems open to it, some of these organizations that you’ve mentioned, go in and take a leadership role. Make sure you’re volunteering for things so people can see how you work with others and the leadership role you’re willing to take. Then they might remember you industry-wide.

I know with different organizations I’m part of, they’ll come to the group first and say, “Does anybody know somebody that would be good for this role?” before they throw it out to the world. You can really get far in that situation.

Tamara Greenspan: 100%. A lot of people, when they’re looking for somebody to join their team or one of their management colleagues, they’re looking for people who are successful. People trust other people so you never know, your sponsor, who all their relationships are. They could have relationships with a lot of people that you just aren’t aware but that’s going to be the person that really – I keep saying that, but that’s what they do – they put themselves out there for you and that’s what a true sponsor is.

That relationship is probably not going to happen overnight, it develops. As you work with somebody, as you create a stronger relationship, that’s going to get stronger so it’s an evolving situation but I feel that’s very important for your job, it’s very important for me.

Gina Stracuzzi: I want to ask this one last question and then I’d like to ask you for one piece of actionable advice that the women and men on this call can think about in terms of getting after a mentor for themselves right away.

Thinking about advocating for yourself and for others, that is something that sometimes doesn’t come very easy for people, especially women. We tend to not toot our own horns very well so what kind of advice can you give to women for advocating for others as well as an aspect of leadership and mentorship?

Tamara Greenspan: I agree with you, it’s hard for women to say, “I’m great at X, Y, Z.” It’s hard but I do think when you’re a mentor, I find it’s easier to advocate for other women who are rock stars and can be very honest, open and give examples. I think it’s easier for me personally as a woman than to talk about myself, it’s not so easy. But it’s much easier to talk about other successful men and women, because we should all be mentoring whoever asks us to mentor if it’s a good fit.

Gina Stracuzzi: That’s why I chuckle when you say, “I’m just a working mother of three selling software.” It’s a rather modest encapsulation of your career but I do applaud it and respect it, but it’s just very modest.

I can’t thank you enough, we’ve had a couple of comments in here, “What an outstanding presentation” and they really appreciate your time, as I do always. What piece of parting advice can you give people? An immediate action step they can take if they’re looking for mentors or want to become one.

Tamara Greenspan: Don’t be afraid to ask, don’t be afraid to put yourself out there, don’t be afraid to let people know that you need help. A lot of times people are just afraid to ask so just be organized, document, think about what you need and then ask because people are afraid, “That person’s too busy, they’ve got too much.” People want to help other people generally so just ask. But again, make sure you have a plan and you ask for something specific because asking generically, you might be going to the wrong person, they might not have the perfect skill set that you’re looking for. The mentors usually have done it before and they know whether they can help or not help and they will be honest about that. It’s time for both parties and you want to make it beneficial.

Gina Stracuzzi: That’s great advice and I really like what you said, get clear. That could be the first step, take out a piece of paper and write down, maybe you’ve got three different columns, difficult situations, career goals, I don’t know what the other one might be. What help do you need in each one of those areas? Because maybe once you write it out, the person you should be asking will become clear.

Tamara Greenspan: Or multiple people, Gina, because it could be different people. It could be somebody within your company for one thing, someone out of your company for other things and it could be a third if you wanted to confide in maybe somebody that you’re close with to just get some advice. It doesn’t have to be just one person either. That’s where the formal and informal can be valuable, because you can have both types. Formal is a little more structured but informal is not as structured, it’s a little more fluid.

Transcribed by Mariana Badillo

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